application of acidic ionic liquid on the catalyic green process...

Application of Acidic Ionic Liquid on the Catalyic Green Process

()

[]2011.11.17

Contents I. What is ionic liquid(IL)? II. Properties of ionic liquids III. Application of acidic IL Lewis acid IL Bronsted acid IL IV. Conclusion

1. : H2SO4 , AlCl3 , HF CF3SO3H, PTSA 2. : Zeolite, H3PO4/SiO2 SO42-/ZrO2, SbF5/TiO2 3. : Amberlyst, Nafion 4. : H3PW12O40(TPA), TPA/S 5.: Lewis /Bronsted Acid IL

Application Method of Conventional Strong Acid Catalyst(A) Lewis Acid Ionic Liquid

(Water-sensitive, Biphasic System)(B) Bronsted Acid Ionic Liquid

(Water-tolerable, Biphasic System)(C) Bronsted Acid Ionic Liquid/ Solid

(Water-tolerable, Biphasic System)[PPS][PPS] [PHC]

What is ionic liquid (IL)?ILs are salts composed entirely of ions, typically large organic cations and small anions, they are liquids at low temperature(

COLORFUL FUTURE Ionic liquids have a promising future in chemicals synthesis.

Typical Structure of Low Temperature ILAnions: BF4-,PF6-,SbF6-,NO3-,CF3SO3-,(CF3SO3)2N-, ArSO3-,CF3CO2-,CH3CO2-,Al2Cl7-,HSO4- Cations:

Properties of Ionic LiquidsLow Vapor Pressure

Thermal Stability (up to 300~400)

Immiscible with Some Organic Solvents

Polarity and Hydrophilicity/Lipophilicity (Adjustable)

Superacidity of Chloroaluminate (H0= -18) (Adjustable)

Characteristics of Ionic Liquids(A)Melting PointsMelting Points with Different Cations

Melting Points with Different Anions

Asymmetry explains the low melting point

(B) Solubility

(C) Thermal Stability

(D)Acidity and Coordination Ability AlCl3 AlCl3 Cl - AlCl4- Al2Cl7-

basic/strongly neutral/weakly acid/non-coordinating coordinating coordinating

Cl- AlCl4- Al2Cl7- Ac- CuCl2- Al3Cl10- NO3- SbF6- SO42- BF4- Cu2Cl3- PF6- Cu3Cl4-basic/strongly neutral/weakly acid/non-coordinating coordinating coordinating

Acid Strength of IL

CH3CNCH3CN-IL FT-IRL acidB acid

PC1pyridine FT-IR(X=0.50, 0.65)

NR3 Step I + RX[RR3N]+X- Step IIb+Metal salt M+A- -MX(precipitation) +Bronsted acid H+A- -HX(evaporation)Ion exchange resin[RR3N]+[MXy+1]- [RR3N]+[A]- Step IIa

+Lewis acid MXySynthesis of Ionic Liquid

Application of Ionic Liquids

Catalytic Research on Ionic LiquidsIonic Liquid Acid Catalysis(B & L acid)Isomerization(Cycloalkane/n-Alkane)Alkylation(Aromatic/Isobutane with C4 Olefin)Polymerization(C4 Olefin)Esterification(FAME)/ TransesterificationIonic Liquid Organometallic CatalysisDimerization(C4 Olefin)/OligomerizationHydrogenation/Oxidation/HydroformylationHeck/Suzuki/Acylation/EsterificationIonic Liquid Nanometal CatalysisSelective HydrogenationPDMA/ Butadiene/ Isoprene/Cyclopentadiene

Acidic Ionic Liquid Catalysis

Acidic Ionic Liquid Catalysis(A)Lewis Acid Ionic Liquid

Polymerization of ButeneAlkylation of Olefin(C4 Olefin/i-C4)Alkylation of Aromatics(Olefin/Aromatic)Isomerization of Cycloalkane(JP-10 & Adamantane) (B)Bronsted Acid Ionic LiquidEsterification of Bio-diesel SynthesisEsterification of Polyol(Glycol & Glycerol)

(A)Lewis Acid Ionic Liquid Polymerization of Butene Adavantage of acidic ionic liquid process:(i) Ease of separation of the product polymer from the catalytic component, further undesirable reaction could be avoided.(ii) The product formed need not to be water-washed, because of low level of the catalytic IL in the product.(iii) The catalyst can be recycled and thereby reduces operation cost.(iv) The higher molecular weight of polymer could be obtained with high yield, even at higher temperature.

(A)Lewis Acid Ionic Liquid Alkylation of Olefin(i-C4/C4=) C4= + i-C4 i-C8(Alkylate fuel ) Conventional process: HF :(UOP &Phillips) /Toxic H2SO4:(Stratco &Kellogg) /Corrosion & waste acid treatment Acidic Ionic Liquid process( Biphasic process): [BMIM]Cl-AlCl3 (Chauvin , 1994)

Alkylation of C4 Olefin with i-C4IonikylationProcess

BMIC/AlCl3/CuCl

(A)Lewis Acid Ionic Liquid Alkylation of Aromatics C6H6 + C2H4= C6H5-C2H5 C6H5-C2H4 ( Styrene ) (AlCl3 or ZSM-5) C6H6 + C3H6= C6H5-iC3H7 C6H5-OH ( Phenol ) (AlCl3 or ZSM-5) C6H6 + C12H24= C6H5-C12H25 ( LAB ) ( Detergent ) [BMIM]Cl-AlCl3

Isomerization of Cycloalkane

Synthesis of JP-10 Synthesis of Adamantane Supported Ionic Liquid Pseudo-fixed-bed Ionic Liquid

(A)Lewis Acid Ionic Liquid

Isomerization of Cycloalkane ( Synthesis of JP-10 ) THDCPDTetrahydrodicyclopentadiene

Representative Properties of Jet & Missile Fuels

JP-4W-5RJ-4RJ-4IRJ-5JP-9JP-10Ave. formulaC9.5H18.9C10H19C12H20C12H20C14H18C10.6H16.2C10H16Ave. mol. wt.133139164164186143136CH ratio0.50.530.60.60.780.650.62Sp. Gr.0.770.830.940.941.080.940.94Freeze pt.

JP-101.(H2SO4) 2.(AlCl3) 3. Zeolites and Heteropoly Acids (185-195)

Experimental

JP-10 X=0.6 , IL/endo-THDCPD=1/12.8(mole ratio) , 50 CSynthesis of JP-10

AlCl3JP-10 [IMC-1]AlCl3 , IL/feed=1/12.8 , 50 C

Anionic Species in Chloroaluminate IL with Different AlCl3 Mole Fraction

AlCl3CH3CN FT-IR(PC-1)

(JP-10) [IMC-1]AlCl3 , X=0.6 , IL/feed=1/12.8 , 50 C

Synthesis of Adamantane

(C10H16), , 2680C,1.07.

, , , .

,, , , , , , .

, .

(Adamantane)

X=0.65 , IL/exo-THDCPD=1/1.28 , 70 C

PHC/AlCl3AlCl3 [PHC]AlCl3 , IL/feed=1/1.28 , 70 C

JP-10Adamantane(I) 1., endo-THDCPD exo-THDCPD(JP-10),(adamantane).

2.ILAlCl3X, 0.60~0.65(JP-10)0.65~0.70 (adamantane), 50~60C(JP-10)60~75C (adamantane).

3.ILX,,, .

JP-10Adamantane(II) 4.,adamantane , .

5. , . 6., , decalin(C10H18), 78/22~68/32, , decalin.

JP-10Adamantane [ US Pat 7488860 (2009) ] [ CNS Pat I 314141 (2009) ] [ Fuel, (2011), in press]

[ US Pat 7488859 (2009) ] [ CNS Pat I 321128 (2010) ][Catal. Communi., 10(13), 1747(2009) ]

JP-10(Pseudo fixed-bed IL reactor)(A)Lewis Acid Ionic Liquid

(A)(B)Temp. controllerProductsFeed pumpFeed

Supported Acidic Ionic Liquid

(A)Lewis Acid Ionic Liquid

Structure of Supported IL (Impregnation & Grafting)

Supported ionic liquids ionic liquid ionic liquid(in CH2Cl2), CH2Cl2 ionic liquid(in CH2Cl2), CH2Cl2AlCl3 (in CH2Cl2), washed by CH2Cl2AlCl3 PHC(in CH2Cl2), wash by CH2Cl2Me3SiCl(in cyclohexae), reflux and washed by CH2Cl2

Support : silica gel (80-120 mesh) Ionic Liquid : PHC/AlCl3 (X=0.65) (SiO2)

Chart1

000000

0.26158777980.3246801130.8074906330.16279881850.87217245460.2478163683

0.31407804680.44121733210.95756942910.45593403230.96859353220.3747583587

0.62452745370.65137205440.98604429470.86448669580.98479327320.7006954169

0.83527950480.81319269040.99023191460.96198073350.98726472690.8677823037

0.96555677430.91601986530.99084937620.98785697490.98772445710.9543058299

0.98685938280.97401072550.99004603270.99057741220.98727012780.9763544091

0.99027094290.98857744190.99140920290.9824237966

0.99151687720.99111204030.99227839090.9890734809

0+0

0.6+0

0.9+0

1.2+0

1.5+0

1.8+0

reaction time(min)

conversion of endo-THDCPD

Effect of silica gel

Sheet3

mpbp

(CH3)3SiCl-4057

Sheet1

0.35/0.65PHC 0.5293g 10wt% 0.65mole AlCl3 1.1338g

1/12.8

reaction temp.50C 600rpm

951101051030601202403601440

SG+CH2Cl2exo-THDCPD111110.99293624510.9920.9910.983

blank1adamantane000000.00440638320.0050.0060.008

0+0alkylTHDCPD000000.00265737170.0030.0040.008

diTHDCPD00000000.0000.000

conversion of endo-THDCPD00.26158777980.31407804680.62452745370.83527950480.96555677430.9870.9900.992

951116051030601202403601440

SG+CH2Cl2exo-THDCPD11111110.99420732960.9866369694

blank2adamantane00000000.00579267040.0082395161

0+0alkylTHDCPD000000000.0051235144

diTHDCPD000000000


951120051030601202403601440

SG+CH2Cl2exo-THDCPD111111111

adamantane000000000

0+5alkylTHDCPD000000000

diTHDCPD000000000


951211051030601202403601440

SG+CH2Cl2exo-THDCPD1111110.99706237750.99422195460.9913608341

0.6adamantane0000000.00293762250.00352553960.0051792203

0.6+0alkylTHDCPD00000000.00225250590.0034599457

diTHDCPD000000000


951031051030601202403601440


0.6adamantane0000000.0030.0040.006

0.6+3alkylTHDCPD0000000.0030.0030.005

diTHDCPD00000000.0000.000


951123051030601202403601440


0.6adamantane000000000

0.6+5alkylTHDCPD000000000

diTHDCPD000000000


951130051030601202403601440

SG+CH2Cl2exo-THDCPD10.9769496670.98863224780.99250057750.9965154521110.99750677060.9973480172

0.6adamantane000000000.0026519828

0.6+5(V)alkylTHDCPD000000000

diTHDCPD000000000


951119051030601202403601440


adamantane000000000


diTHDCPD000000000


951109051030601202403601440

SG+CH2Cl2exo-THDCPD11110.99747549590.99710751020.99682759430.99670138660.9960500829

1.2(no CH2Cl2)adamantane00000.00252450410.00289248980.00317240570.00329861340.0039499171


diTHDCPD000000000

SGPHCAlCl3conversion of endo-THDCPD00.47807121540.74928053360.92502619030.96990550660.98641196770.99084570960.99142924440.9913096935

951128051030601202403601440

SG+CH2Cl2exo-THDCPD11110.9970.9970.9960.9960.991


1.2+0alkylTHDCPD000000000.003

diTHDCPD000000000.0

IL+SGconversion of endo-THDCPD00.1630.4560.8640.9620.9880.9910.9910.992

951115051030601202403601440


adamantane000000000


diTHDCPD000000000

SGPHC+ AlCl3+CH2Cl2conversion of endo-THDCPD00.31762135690.57945715260.85533415240.93980122480.97654062810.98879152950.98983963130.9914589993

951121051030601202403601440


adamantane000000000


diTHDCPD000000000

IL+SGconversion of endo-THDCPD00.32942223810.54451024350.78989745760.90514151140.96798335810.98723401860.98972349540.9911010384

951129051030601202403601440

SG+CH2Cl2exo-THDCPD1111110.99611

adamantane000000000


diTHDCPD000000000


951114051030601202403601440


1.2+5(N2)adamantane000000000

alkylTHDCPD000000000

diTHDCPD000000000

solventconversion of endo-THDCPD00.20880175970.3777901040.77941263640.94061606480.9801938410.98976426870.99100268290.9915301626

951122051030601202403601440


1.2+5(V)adamantane000000000


diTHDCPD000000000

SGPHC+ AlCl3+CH2Cl2,N2,vaccumconversion of endo-THDCPD00.23239568770.36980960780.73552231340.9054272350.96822136380.98787136920.99104279220.9920478798

951206051030601202403601440


1.2+5(V)adamantane00000000.00223135750.0031401451


diTHDCPD000000000

PHC+AlCl3+CH2Cl2SG,vaccumconversion of endo-THDCPD00.14070216710.22409279770.48279746620.63220880040.80735644540.95117821660.97186475440.9905601121

951207051030601202403601440


1.2+10(V)adamantane00000000.0020.002


diTHDCPD000000000


951127051030601202403601440




diTHDCPD000000000


951205051030601202403601440




diTHDCPD000000000


951204051030601202403601440


1.8+0adamantane0000000.00238492780.0030.003


diTHDCPD000000000


Sheet1

00000000000000

00000000000000

00000000000000

00000000000000

00000000000000

00000000000000

00000000000000

00000000000000

00000000000000

0+0

0+0

0+5

0.6+3

0.6+5

0.6+10

1.2+0

1.2+5

1.2+5

1.2+10

1.2+5(N2)

0.6+5(V)

1.2+5(V)

1.8+5(V)

reaction time(min)


Effect of silica gel and CH2Cl2

table9511

0000

0000

0000

0000

0000

0000

0000

0000

0000

0+0

1.2+0

1.2+5(V)

1.2+10(V)

reaction time(min)


Effect of CH2Cl2

table9511 (2)

000000

000000

000000

000000

000000

000000

000000

000000

000000

0.6+3

0.6+5

0.6+10

1.2+0

1.2+5

1.2+10

reaction time(min)


Effect of CH2Cl2

table9511 (3)

0000

0000

0000

0000

0000

0000

0000

0000

0000

0+0

0.6+5(V)

1.2+5(V)

1.8+5(V)

reaction time(min)



table9511 (4)

000

000

000

000

000

000

000

000

000

0+0

1.2+0

1.8+0

reaction time(min)



table9511 (5)

11/8/06

reactantendo-THDCPDPHC+SG+AlCl3+CH2Cl2

silica gel 80-120A

MW136.24115.56133.34

density

10wt%

11/12.820.65mole fraction

0.5293g+1.1338 g + 5ml1.2g +5ml

Stirr(rpm)600rpm

temperature50C

Timetemp.(soln)THDCPD/ADM

test1

11/8/06

reactantendo-THDCPDPHC+

MW136.24115.56133.34

density

10wt%

11/12.82

0.5293g+1.1338 g + 5mlg+ g/ g+20ml

Stirr(rpm)600rpm

temperature50C

Timetemp.(soln)

951024

1/25/07

reactantendo-THDCPDPHC+

silica gel 80-120A

MW136.24115.56133.34

density

10wt%

11/12.820.65mole fractionreflux 4hr

0.5293g+1.1338 g + 5ml1.2g +0.6g +10ml

Stirr(rpm)600rpm

temperature50C


951025

2/27/07

reactantendo-THDCPDHDMIC+

MW136.24343133.34

density

10wt%


1.57g+0.916 g + 5ml1.2g +1.2g +5ml

Stirr(rpm)600rpm

temperature50C


SiO-Al(100)

11/8/06

reactantendo-THDCPDPHC+SG

silica gel 80-120A

MW136.24115.56133.34

density

10wt%


0.5293g+0.916 g1.2g

Stirr(rpm)600rpm

temperatureC


951026

950818PHC(1/25.6 to feed)+AlCl3(0.6)+CH2Cl2+MMTno reaction

950821PHC(1/25.6 to feed)+AlCl3(0.75)+CH2Cl2+MMTno reaction

950822PHC(1/25.6 to feed)+AlCl3(0.6)+CH2Cl2+silica gelno reaction

951030

951024

silica gel 1g+ AlCl3 1g+ CH2Cl2 3ml


12.8/1.0

reaction temperature50C 600rpm

0306012024036014401440

C6-11.879557.719377.995317.9487.621967.515916.630054.38379

cyclohexane46.8553539.4091838.7514938.1125837.0274636.4721632.5245141.53168

C6-200000000

transDHN0001.251092.304463.176067.384510

exoTHDCPD13.5910849.4943450.2024747.5151644.4566141.3418428.233350

adamantane00.821841.555082.99845.378037.0442514.466880

endoTHDCPD37.674022.063070.623620.37676000.1674954.08453

cisDHN00000000

AlkylTHDCPD00.49220.872031.797992.887853.752948.074990

00000.323640.543332.165080

total10010010099.99998100.0000199.8464999.64686100

total of C648.734947.1285546.746846.0605844.6494243.9880739.1545645.91547

total of C1051.265152.3792552.3811752.1414152.139151.5621550.2522354.08453

selectivity

0306012024036014401440

exo-THDCPD10.97413733720.95388315850.88709518430.80318222440.74011832060.46802219520

adamantane00.01617528450.02954764220.05597931690.09716301130.12610900920.23981642050

alkylTHDCPD00.00968737830.01656919930.03356798690.05217378890.0671866480.13385852350

00000.00584709210.00972691310.03589037410

endo-THDCPD0.73488630670.03902049220.011710470.0069848756000.00276878211

conversion of endo-THDCPD00.94690268170.98406492290.9904952976110.9962323667-24.6275598986

selectivity of C7

030601202403601440

C7-isomer10.03856681760.16379392110.1710343810.17255536080.17070680870.17086246340.1693302134

n-heptane0.96143318240.83620607890.8289656190.82744463920.82929319130.82913753660.8306697866

C7isomer20000000

951031

951025

silica gel 5.745g


12.8/1.0


030601202403601440

C6-103.123315.615776.594167.352417.590217.21542

cyclohexane48.4515244.0987140.8383739.5895138.3802337.8223234.81441

C6-20000000

transDHN0000000

exoTHDCPD1.9980328.6159748.4164251.814652.2023752.2749452.66987

adamantane000.376150.557450.832051.030862.59942

endoTHDCPD49.5504524.008174.521940.985510.570470.47020.43706

cisDHN0000000

AlkylTHDCPD00.153840.231350.458760.662470.811472.26382

0000000

total10010010099.99999100100100

total of C648.4515247.2220246.4541446.1836745.7326445.4125342.02983

total of C1051.5484852.6241453.3145153.3575653.6048953.77655.70635

selectivity

030601202403601440

exo-THDCPD10.9946527280.98760809010.98076482260.97216747560.96595670850.9154705873

adamantane000.0076727850.0105516080.01549531080.01904863270.0451812878

alkylTHDCPD00.0053472720.00471912490.00868356930.01233721360.01499465880.0393481249

0000000

endo-THDCPD0.96123978830.45488989920.08444985290.01831247470.01051221210.00861369830.0075393948

conversion of endo-THDCPD00.52676750930.91214486340.98094910870.98906390240.99103897020.9921565931

selectivity of C7

030601202403601440

C7-isomer100.06614096560.12088847190.14278120380.16076941980.16713911340.171673785

n-heptane10.93385903440.87911152810.85721879620.83923058020.83286088660.828326215

C7isomer20000000

SiO-Al(10)


1/12.8


951030051030601202403601440

SG+AlCl3exo-THDCPD110.9967700270.98828300980.98100993990.97432749530.96536974870.95241963170.8778594965

adamantane0000.00776883430.01063735110.01439676740.01956483110.02551870430.0665099762

0alkylTHDCPD000.0032299730.0039481560.0083527090.01127573740.01506542020.0220616640.052999319

diTHDCPD000000000.0026312083


951026051030601202403601440

SG+AlCl3exo-THDCPD110.99676224840.98804637420.97949969150.97155018060.95241012430.94271064540.7958224931

adamantane0000.00761558210.01118634830.01567202170.0252058110.03057088920.0855472865

1alkylTHDCPD000.00323775160.00433804370.00931396010.01277779760.02238406470.02671846540.0668945995

diTHDCPD000000000.0031733025


951025030601202403601440

exo-THDCPD10.9946527280.98760809010.98076482260.97216747560.96595670850.9154705873

adamantane000.0076727850.0105516080.01549531080.01904863270.0451812878

5alkylTHDCPD00.0053472720.00471912490.00868356930.01233721360.01499465880.0393481249

diTHDCPD0000000

conversion of endo-THDCPD00.52676750930.91214486340.98094910870.98906390240.99103897020.9921565931

951101

951026

silica gel 1g


12.8/1.0


051030601202403601440

C6-11.487113.674144.53576.310197.248167.47027.607867.372387.12261

cyclohexane46.7200644.1335442.8670240.7869539.2220938.8678239.0821738.355734.86367

C6-2000000000.13876

transDHN000000002.79486

exoTHDCPD17.6928937.5205944.47651.0371651.852551.7124150.4026250.7960445.8012

adamantane0000.393380.592180.834171.333921.647254.92342

endoTHDCPD34.0999414.671747.976811.248240.592020.435280.388840.388960.32293

cisDHN000000000

AlkylTHDCPD000.144470.224080.493060.680121.184591.439673.84992

000000000.18263

total100100.00001100100100.00001100100100100

total of C648.2071747.8076847.4027247.0971446.4702546.3380246.6900345.7280842.12504

total of C1051.7928352.1923352.4528152.6787853.036752.9818652.1253852.8322553.84241

selectivity

051030601202403601440

exo-THDCPD110.99676224840.98804637420.97949969150.97155018060.95241012430.94271064540.7958224931

adamantane0000.00761558210.01118634830.01567202170.0252058110.03057088920.0855472865

alkylTHDCPD000.00323775160.00433804370.00931396010.01277779760.02238406470.02671846540.0668945995

000000000.0031733025

endo-THDCPD0.65839113250.28110912080.15165822260.02359494360.01105964230.00811151580.00729394520.00716687380.0055797879


selectivity of C7

051030601202403601440

C7-isomer10.03084831570.07685250570.09568438270.13398244560.15597419850.16121103150.16294399470.16122216370.1690825694

n-heptane0.96915168430.92314749430.90431561730.86601755440.84402580150.83878896850.83705600530.83877783630.8276234278

C7isomer2000000000.0032940028

951102

951030

silica gel 0g


12.8/1.0


051030601202403601440

C6-10.23484.517545.051266.428477.290717.584467.670697.719397.09443

cyclohexane48.3965143.4113742.652340.5118839.3053938.6325638.3389637.9137934.07553

C6-2000000000

transDHN000000000

exoTHDCPD2.6160439.9493344.1884551.399751.9179451.9906951.7184151.3810251.29283

adamantane0000.404050.562960.768221.048161.376683.88614

endoTHDCPD48.7526512.121767.964811.050560.480960.422390.416670.418950.40062

cisDHN000000000

AlkylTHDCPD000.143190.205340.442050.601680.807111.190183.09672

000000000.15374

total100100100.00001100100.00001100100100.00001100.00001

total of C648.6313147.9289147.7035646.9403546.596146.2170246.0096545.6331841.16996

total of C1051.3686952.0710952.1532652.8543152.9618653.181353.1832453.1766555.57959

selectivity

051030601202403601440

exo-THDCPD110.9967700270.98828300980.98100993990.97432749530.96536974870.95241963170.8778594965

adamantane0000.00776883430.01063735110.01439676740.01956483110.02551870430.0665099762

alkylTHDCPD000.0032299730.0039481560.0083527090.01127573740.01506542020.0220616640.052999319

000000000.0026312083

endo-THDCPD0.94907325840.2327925150.152301160.01979960290.00900608210.00785359980.00771749030.00770598540.0068097851


selectivity of C7

051030601202403601440

C7-isomer10.00482816520.09425501230.10588853330.13694976710.15646609910.16410534470.16671915570.1691617810.1723205463

n-heptane0.99517183480.90574498770.89411146670.86305023290.84353390090.83589465530.83328084430.8308382190.8276794537

C7isomer2000000000

951106

951031

silica gel 0.6g CH2Cl2 3ml


12.8/1.0


051030601202403601440

C6-12.489042.891963.291664.341385.155745.989136.4826.885217.35636

cyclohexane47.5589546.660845.8703544.3093943.4932442.0155241.2677641.0878437.41908

C6-2000000000

transDHN000000000

exoTHDCPD1.929637.9848616.1496932.2094741.2202149.2267651.2435151.2709154.22193

adamantane0000000.178290.202480.31782

endoTHDCPD48.0223842.4623834.688319.1397710.13082.76860.690310.399930.43132

cisDHN000000000

AlkylTHDCPD0000000.138140.153630.25349

000000000

total100100100100.0000199.99999100.00001100.00001100100

total of C650.0479949.5527649.1620148.6507748.6489848.0046547.7497647.9730544.77544

total of C1049.9520150.4472450.8379951.3492451.3510151.9953652.1121151.8733254.97107

selectivity

051030601202403601440

exo-THDCPD1111110.99386287110.99310225540.9895733488

adamantane0000000.00345791710.00392197730.0058003506

alkylTHDCPD0000000.00267921180.00297576730.0046263006

000000000

endo-THDCPD0.96137032320.84171859550.6823302810.37273716220.19728531140.0532470590.01321161140.00768697760.0078102931


selectivity of C7

051030601202403601440

C7-isomer10.04973306620.05836122950.06695535840.08923558660.10597837820.12476145540.13574937340.14352245690.1642945329

n-heptane0.95026693380.94163877050.93304464160.91076441340.89402162180.87523854460.86425062660.85647754310.8357054671

C7isomer2000000000

951107


1/1.28


951101051030601202403601440

SG+AlCl3exo-THDCPD111110.99293624510.9920.9910.983

adamantane000000.00440638320.0050.0060.008

0alkylTHDCPD000000.00265737170.0030.0040.008

diTHDCPD00000000.0000.000


951102051030601202403601440

SG+AlCl3exo-THDCPD1110.99275284560.98801730380.9830167920.9680.9600.983

0.6+0.3adamantane0000.00416184560.00755880940.01104353130.0180.0230.008

alkylTHDCPD0000.00308530880.00442388690.00593967670.0130.0170.008

diTHDCPD00000000.0000.000


951031051030601202403601440

SG+AlCl3exo-THDCPD1111110.9940.9930.990

0.6+0adamantane0000000.0030.0040.006

0.6+0alkylTHDCPD0000000.0030.0030.005

diTHDCPD00000000.0000.000


951107051030601202403601440

SG+AlCl3exo-THDCPD111110.99775837310.9910.9970.994

0.6+0.3(air)adamantane000000.00224162690.0050.0030.004

alkylTHDCPD0000000.0030.0000.002

diTHDCPD00000000.0000.000


SiO-Al(11)

951101

silica gel 0g CH2Cl2 0ml


12.8/1.0


051030601202403601440

C6-10.223631.128411.275932.346523.215044.188584.785845.255826.29156

cyclohexane47.9057246.8115446.8279745.0673244.1694643.310642.0582241.4565737.93045

C6-20.190570.174180000000

transDHN000000000

exoTHDCPD3.2385515.9736218.530134.078844.4917650.4469652.0614152.3001754.3938

adamantane000000.223870.276940.315660.47033

endoTHDCPD48.4415335.9122633.3659918.507358.123741.694980.654730.485950.44352

cisDHN000000000

AlkylTHDCPD000000.135010.162860.185820.47033

000000000

total100100.0000199.9999999.9999910010010099.9999999.99999

total of C648.3199248.1141348.103947.4138447.384547.4991846.8440646.7123944.22201

total of C1051.6800851.8858851.8960952.5861552.615552.3658152.9930853.1017855.30765

selectivity

051030601202403601440

exo-THDCPD111110.99293624510.99162305020.99050256950.9830004666

adamantane000000.00440638320.0052749260.00597822230.0084997667

alkylTHDCPD000000.00265737170.00310202370.00351920820.0084997667

000000000

endo-THDCPD0.93733465580.69213936430.64293841790.351943430.15439822870.03228482910.01231715590.00911938240.007951525


selectivity of C7

051030601202403601440

C7-isomer10.0046281120.02345277780.02652446060.0494901910.06785003530.08818215390.10216535460.11251447420.14227214

n-heptane0.99142796590.97292707980.97347553940.9505098090.93214996470.91181784610.89783464540.88748552580.85772786

C7isomer20.00394392210.00362014240000000

CH2Cl2effect

951102

silica gel 0.6g AlCl3 0.3g CH2Cl2 3ml


12.8/1.0


051030601202403601440

C6-13.025233.809444.760497.082048.656389.300689.456019.447216.29156

cyclohexane46.8491945.58943.930241.4488639.6273338.7535337.7280437.0781837.93045

C6-2000000000

transDHN000000000

exoTHDCPD5.1202221.3829434.9245848.5708450.5366850.6314350.7586350.9651354.3938

adamantane0000.203620.386630.568810.948931.224940.47033

endoTHDCPD45.0053729.2186316.384732.543680.566690.439620.404920.406820.44352

cisDHN000000000

AlkylTHDCPD0000.150950.226280.305930.703470.877730.47033

000000000

total100.00001100.0000110099.9999999.99999100100100.0000199.99999

total of C649.8744249.3984448.6906948.530948.2837148.0542147.1840546.5253944.22201

total of C1050.1255950.6015751.3093151.3181451.4951.6398652.1124852.5968955.30765

selectivity

051030601202403601440

exo-THDCPD1110.99275284560.98801730380.9830167920.96847228530.96037766780.9830004666

adamantane0000.00416184560.00755880940.01104353130.018105540.02308254720.0084997667

alkylTHDCPD0000.00308530880.00442388690.00593967670.01342217470.0165397850.0084997667

000000000

endo-THDCPD0.89785217490.57742536450.31933249540.04942150720.01095767140.00846305350.00766662340.00760772120.007951525


selectivity of C7

051030601202403601440

C7-isomer10.0606569460.07711660530.09777002540.14592847030.17928158380.19354558110.20040691720.20305493410.14227214

n-heptane0.9393430540.92288339470.90222997460.85407152970.82071841620.80645441890.79959308280.79694506590.85772786

C7isomer2000000000

951108

951106



12.8/1.0


051030601202403601440

C6-12.924923.456974.021886.264238.346069.03449.359519.228328.77414

cyclohexane46.9667346.2435345.1196142.0475739.9054638.4114637.6676536.764533.60186

C6-2000000000

transDHN000000000

exoTHDCPD4.4607112.8805924.3224444.207350.0199351.0539450.9588751.5204649.90787

adamantane00000.395830.583550.904711.196894.06532

endoTHDCPD45.6476337.4189126.536067.338131.104840.609530.441580.438720.39875

cisDHN000000000

AlkylTHDCPD0000.142770.227870.307120.667680.851122.93628

000000000.31577

total99.9999910099.9999910099.99999100100100.0000199.99999

total of C649.8916549.700549.1414948.311848.2515247.4458647.0271645.9928242.376

total of C1050.1083450.299550.858551.5454351.520652.2470252.3051653.1560754.37194

selectivity

051030601202403601440

exo-THDCPD1110.99678083940.98768453210.98285346640.97006753690.96176836860.8721303746

adamantane00000.00781598790.01123408180.01722231680.02234318060.0710406807

alkylTHDCPD0000.00321916060.004499480.00591245170.01271014630.01588845080.051310925

000000000.0055180197

endo-THDCPD0.91097869140.74392210660.52176253720.14196915350.02135019640.01159813480.00833596990.00812336280.006919861


selectivity of C7

051030601202403601440

C7-isomer10.05862544130.06955604070.08184285820.12966252550.17296988780.19041492770.19902350050.20064697050.2070544648

n-heptane0.94137455870.93044395930.91815714180.87033747450.82703011220.80958507230.80097649950.79935302950.7929455352

C7isomer2000000000

951109

951107



12.8/1.0


051030601202403601440

C6-100.414841.189442.006042.733033.070694.474413.839344.56357

cyclohexane48.8342248.0244347.0638645.6609144.5543743.3881539.7075543.1412841.43323

C6-2000000000

transDHN000000000

exoTHDCPD0.500876.8312822.1483138.4745149.1806252.4377754.6442152.3916253.25274

adamantane000000.117810.295380.150270.19484

endoTHDCPD50.6649144.7294429.5983913.858543.531980.985580.701960.477490.42891

cisDHN000000000

AlkylTHDCPD0000000.176500.12671

000000000

total10099.99999100100100100100.00001100100

total of C648.8342248.4392748.253347.6669547.287446.4588444.1819646.9806245.9968

total of C1051.1657851.5607251.746752.3330552.712653.5411655.6415553.0193853.87649

selectivity

051030601202403601440

exo-THDCPD111110.99775837310.99143843480.99713999630.9939980539

adamantane000000.00224162690.00535923360.00286000370.0036368191

alkylTHDCPD0000000.003202331700.002365127

000000000

endo-THDCPD0.99021084010.8675099960.57198603970.26481430.06700447330.0184078940.01257586030.00900595220.0079423071


selectivity of C7

051030601202403601440

C7-isomer100.00856412580.02464992030.04208450510.05779615710.06609484870.10127232920.08172178230.0992149454

n-heptane10.99143587420.97535007970.95791549490.94220384290.93390515130.89872767080.91827821770.9007850546

C7isomer2000000000

951114


1/1.28


951101051030601202403601440


adamantane000000.00440638320.0050.0060.008

0+0alkylTHDCPD000000.00265737170.0030.0040.008

diTHDCPD00000000.0000.000


951031051030601202403601440


0.6adamantane0000000.0030.0040.006

0.6alkylTHDCPD0000000.0030.0030.005

diTHDCPD00000000.0000.000


951109051030601202403601440

SG+AlCl3exo-THDCPD11110.99747549590.99710751020.99682759430.99670138660.9960500829


1.2alkylTHDCPD000000000

diTHDCPD000000000


951114051030601202403601440

SG+AlCl3exo-THDCPD111111111

1.2+CH2Cl2(N2)adamantane000000000


diTHDCPD000000000


951115


1/1.28


951101051030601202403601440


adamantane000000.00440638320.0050.0060.008

blank1alkylTHDCPD000000.00265737170.0030.0040.008

diTHDCPD00000000.0000.000


951116051030601202403601440


adamantane00000000.00579267040.0082395161

blank2alkylTHDCPD000000000.0051235144

diTHDCPD000000000


951120051030601202403601440


adamantane000000000

5mlCH2Cl2alkylTHDCPD000000000

diTHDCPD000000000


951116

951108



12.8/1.0


051030601202403601440

C6-1000.263560.686241.161451.868252.938953.319745.05887

cyclohexane48.3700347.8122547.4149646.6067645.7762545.3062243.5187743.6132839.90625

C6-2000000000

transDHN000000000

exoTHDCPD0.726061.372963.06558.801915.3990524.604937.8573341.4551453.12098

adamantane000000000.37377

endoTHDCPD50.9039150.8147949.2559843.905137.6632528.1019315.546711.467941.31905

cisDHN000000000

AlkylTHDCPD000000.11870.138250.14390.22109

000000000

total100100100100100100100100100.00001

total of C648.3700347.8122547.6785247.29346.937747.1744746.4577246.9330244.96512

total of C1051.6299752.1877552.3214852.70753.062352.7068353.4040352.9230854.8138

selectivity

051030601202403601440

exo-THDCPD111110.99519891930.99636141890.99654078560.9889257992

adamantane000000000.0069582827

alkylTHDCPD000000.00480108070.00363858110.00345921440.0041159181

000000000

endo-THDCPD0.98593723760.97369191050.94141029650.83300320640.70979301690.53197630010.29036305510.2161031210.0239675231


selectivity of C7

051030601202403601440

C7-isomer1000.00552785610.01451039270.02474450180.03960298870.06326074550.07073356880.1125065384

n-heptane110.99447214390.98548960730.97525549820.96039701130.93673925450.92926643120.8874934616

C7isomer2000000000

951119

951109

silica gel 1.2g AlCl3 0g CH2Cl2 0ml


12.8/1.0


051030601202403601440

C6-101.607192.489943.198123.494093.636213.799053.914444.11453

cyclohexane48.4946746.1654945.1239144.3951743.6625742.7647542.4457442.3037939.4014

C6-2000000000

transDHN000000000

exoTHDCPD3.225926.6756740.0745548.7236751.2230252.7632953.1248753.1737155.80267

adamantane00000.129640.153060.169070.175980.22129

endoTHDCPD48.2794325.5516512.31163.683041.490690.682690.461270.432080.46012

cisDHN000000000

AlkylTHDCPD000000000

000000000

total100100100100100.00001100100100100.00001

total of C648.4946747.7726847.6138547.5932947.1566646.4009646.2447946.2182343.51593

total of C1051.5053352.2273252.3861552.4067152.8433553.5990453.7552153.7817756.48408

selectivity

051030601202403601440

exo-THDCPD11110.99747549590.99710751020.99682759430.99670138660.9960500829

adamantane00000.00252450410.00289248980.00317240570.00329861340.0039499171


000000000

endo-THDCPD0.93736764720.48923915680.23501631630.07027802360.02820960440.01273698190.00858093570.00803394910.0081460121


selectivity of C7

051030601202403601440

C7-isomer100.033642450.05229444790.06719686750.07409536640.07836497350.08215087580.08469471890.0945522709

n-heptane10.966357550.94770555210.93280313250.92590463360.92163502650.91784912420.91530528110.9054477291

C7isomer2000000000

951120

951114


12.8/1.0


051030601202403601440

C6-10.654431.279521.607582.580963.255783.508173.626483.686293.8507

cyclohexane48.0533847.4671346.9423846.1826945.392444.944844.1613743.5073940.21956

C6-20.603080.530470.68735000000

transDHN000000000

exoTHDCPD4.3278314.0174821.8743740.8992348.5627250.6132451.7233552.3717855.49647

adamantane000000000

endoTHDCPD46.3612736.705428.8883210.337122.789110.933780.48880.434550.43327

cisDHN000000000


000000000

total99.99999100100100100.0000199.99999100100.00001100

total of C649.3108949.2771249.2373148.7636548.6481848.4529747.7878547.1936844.07026

total of C1050.689150.7228850.7626951.2363551.3518351.5470252.2121552.8063355.92974

selectivity

051030601202403601440

exo-THDCPD111111111

adamantane000000000


000000000

endo-THDCPD0.91462010570.72364581820.56908568080.20175363780.05431374110.01811511120.00936180560.00822912710.0077466836


selectivity of C7

051030601202403601440

C7-isomer10.01327151060.02596580320.03264963090.05292794940.06692501140.07240361120.07588707170.07810982320.0873763849

n-heptane0.97449833090.96326916020.95339042690.94707205060.93307498860.92759638880.92411292830.92189017680.9126236151

C7isomer20.01223015850.01076503660.0139599422000000

951121

951115


12.8/1.0


051030601202403601440

C6-14.845965.382655.752116.521756.79617.022987.0616.94516.68212

cyclohexane47.0885245.9879145.4833944.5201343.9433243.9750243.4783942.8311442.00142

C6-2000000000

transDHN000000000

exoTHDCPD7.9763720.9525131.6601343.0508846.7872548.0432248.9982349.7981450.9509

adamantane000000000

endoTHDCPD40.0891627.6769317.104385.907232.473320.958790.462380.425610.36556

cisDHN000000000


000000000

total100.00001100100.0000199.9999999.99999100.0000110099.99999100

total of C651.9344851.3705651.235551.0418850.7394250.99850.5393949.7762448.68354

total of C1048.0655348.6294448.7645148.9581149.2605749.0020149.4606150.2237551.31646

selectivity

051030601202403601440

exo-THDCPD111111111

adamantane000000000


000000000

endo-THDCPD0.83405217830.56913939370.35075467790.12065886530.05020891960.01956634020.00934844920.00847427760.0071236403


selectivity of C7

051030601202403601440

C7-isomer10.09330910790.10478083170.11226805630.12777252720.13394122360.13771089060.13971280620.13952640860.1372562472

n-heptane0.90669089210.89521916830.88773194370.87222747280.86605877640.86228910940.86028719380.86047359140.8627437528

C7isomer2000000000

951123

951116

silica gel 0g AlCl3 0g CH2Cl2 0ml repeat 95/11/1


12.8/1.0


051030601202403601440

C6-100.749811.317982.574533.270273.976914.822725.067496.31328

cyclohexane49.3515748.4411447.4845246.0984244.7477243.6773342.978641.6460738.96543

C6-20.4249900000000

transDHN000000000

exoTHDCPD1.937889.3510318.6800335.0906843.6146749.5088451.5103652.490253.55574

adamantane00000000.305830.44725

endoTHDCPD48.2855541.4580232.5174816.236368.367342.836920.688320.490410.44019

cisDHN000000000

AlkylTHDCPD000000000.27811

000000000

total99.99999100100.0000199.99999100100100100100

total of C649.7765649.1909548.802548.6729548.0179947.6542447.8013246.7135645.27871

total of C1050.2234350.8090551.1975151.3270451.9820152.3457652.1986853.2864454.44318

selectivity

051030601202403601440

exo-THDCPD11111110.99420732960.9866369694

adamantane00000000.00579267040.0082395161

alkylTHDCPD000000000.0051235144

000000000

endo-THDCPD0.96141482170.81595739340.63513791980.31633150870.16096607270.05419579350.01318654030.00920327950.0080442183


selectivity of C7

051030601202403601440

C7-isomer100.01524284450.02700640340.05289447220.06810509980.08345343460.10089093770.10848006450.1394315342

n-heptane0.99146204560.98475715550.97299359660.94710552780.93189490020.91654656540.89910906230.89151993550.8605684658

C7isomer20.008537954400000000

951127

951119



12.8/1.0


051030601202403601440

C6-19.130959.03328.698619.05799.504829.453769.27579.226188.45549

cyclohexane44.6333244.2162943.6763743.0925743.0659141.9410642.3331841.5836241.89585

C6-200.953180.837640.850230.888220.9381600.587230.57564

transDHN000000000

exoTHDCPD4.8144813.0357120.119524.6439234.3093638.8830242.2446843.8580846.84442

adamantane000000000

endoTHDCPD41.4212432.7616126.6678722.3553712.231698.783996.146444.744882.22861

cisDHN000000000


000000000

total99.9999999.9999999.9999999.9999910099.9999910099.99999100.00001

total of C653.7642754.2026753.2126253.000753.4589552.3329851.6088851.3970350.92698

total of C1046.2357245.7973246.7873746.9992946.5410547.6670148.3911248.6029649.07303

selectivity

051030601202403601440

exo-THDCPD111111111

adamantane000000000


000000000

endo-THDCPD0.89587098460.71536085520.56998010360.47565335560.26281508470.18427818320.12701586570.09762532980.0454141511


selectivity of C7

051030601202403601440

C7-isomer10.16983305080.16665599680.1634689290.17090151640.17779660840.18064631520.17973069750.17950803770.1660316398

n-heptane0.83016694920.81575852260.82078969240.813056620.80558840010.80142693960.82026930250.80906659390.8226651178

C7isomer200.01758548060.01574137860.01604186360.01661499150.017926745200.01142536840.0113032424

951128

951120



12.8/1.0


051030601202403601440

C6-14.345325.769165.947396.111426.693056.824787.053977.162487.96721

cyclohexane46.9045544.8744344.0231343.249242.4172941.8973941.6456740.9499440.74823

C6-20.677320.651720.725510.861760.936760.786340.591270.499840.47924

transDHN000000000

exoTHDCPD1.5950726.7512733.9012640.6939948.0491549.7217250.2454950.9970650.43883

adamantane000000000

endoTHDCPD46.4777421.9534215.402719.053621.903760.769770.463610.390670.36649

cisDHN000000000


000000000

total10010010099.96999100.00001100100.0000199.99999100

total of C651.9271951.2953150.6960350.2223850.047149.5085149.2909148.6122649.19468

total of C1048.0728148.7046949.3039749.7476149.9529150.4914950.709151.3877350.80532

selectivity

051030601202403601440

exo-THDCPD111111111

adamantane000000000


000000000

endo-THDCPD0.96681970540.45074550320.31240303770.18199105440.0381110930.01524553940.00914254050.00760239850.0072136146


selectivity of C7

051030601202403601440

C7-isomer10.08368101570.11246954160.11731470890.12168718410.13373502160.13785064430.14310894240.14733896350.1619526746

n-heptane0.90327533610.87482520330.86837430860.86115393180.84754741030.84626642980.84489553960.84237885670.8283056217

C7isomer20.01304364820.01270525510.01431098250.01715888410.01871756810.0158829260.0119955180.01028217980.0097417038

951129

951121



12.8/1.0


051030601202403601440

C6-14.601485.355635.68475.406196.853457.258957.22557.357587.06091

cyclohexane46.5874545.5502844.5930642.2730843.1988142.6598641.816441.5007838.5314

C6-20.501610.72460.9259400.860260.884720.865440.890760.63178

transDHN000000000

exoTHDCPD6.3345720.1870929.484542.7694345.0416947.8278949.5370349.8021853.36011

adamantane000000000

endoTHDCPD41.9748928.1824119.311819.55134.04581.368570.555630.448690.4158

cisDHN000000000


000000000

total100100.00001100.00001100100.0000199.9999910099.99999100

total of C651.6905451.6305151.203747.6792750.9125250.8035349.9073449.7491246.22409

total of C1048.3094648.369548.7963152.3207349.0874949.1964650.0926650.2508753.77591

selectivity

051030601202403601440

exo-THDCPD111111111

adamantane000000000


000000000

endo-THDCPD0.86887516440.58264836310.39576373710.1825528810.08242018490.0278184650.01109204420.00892899960.0077320867


selectivity of C7

051030601202403601440

C7-isomer10.08901977030.10372994570.11102127390.11338659340.13461227220.14288278790.14477830320.14789367130.1527538995

n-heptane0.90127613290.88223571680.87089526730.88661340660.84849090160.83970267420.83788076060.83420128840.8335783355

C7isomer20.00970409670.01403433740.018083458800.01689682620.01741453790.01734093620.01790504030.013667765

951130

951123



12.8/1.0


051030601202403601440

C6-14.886784.878955.775146.322147.13977.693168.363328.396268.34664

cyclohexane46.5851446.3263545.6513844.2115543.4967542.2892441.81540.8630138.08166

C6-2000000000

transDHN000000000

exoTHDCPD2.716216.510414.7491427.0580836.6057744.5751348.6459750.0832953.11105

adamantane000000000

endoTHDCPD45.8118742.284333.8243422.4082312.757785.442471.175720.657440.46065

cisDHN000000000


000000000

total100100100100100100100.00001100100

total of C651.4719251.205351.4265250.5336950.6364549.982450.1783249.2592746.4283

total of C1048.5280848.794748.5734849.4663149.3635550.017649.8216950.7407353.5717

selectivity

051030601202403601440

exo-THDCPD111111111

adamantane000000000


000000000

endo-THDCPD0.94402807610.86657567320.69635405990.45299982960.25844535090.10881109850.02359855720.01295684950.0085987564


selectivity of C7

051030601202403601440

C7-isomer10.09494069780.0952821290.11229886840.12510742830.14099922090.15391737890.1666719810.17045035380.1797748356

n-heptane0.90505930220.9047178710.88770113160.87489257170.85900077910.84608262110.8333280190.82954964620.8202251644

C7isomer2000000000

951204

951127


12.8/1.0


051030601202403601440

C6-1000000.509410.658420.775391.00383

cyclohexane49.1797748.6623748.6438248.3620148.0342447.6107146.3763646.9276943.5528

C6-2000000000

transDHN000000000

exoTHDCPD2.10783.603435.424428.3025710.990413.4509617.0601119.1677327.19731

adamantane000000000

endoTHDCPD48.7124347.734245.9317643.3354240.9753638.4289235.9051133.1291928.24606

cisDHN000000000


000000000

total100100100100100100100100100

total of C649.1797748.6623748.6438248.3620148.0342448.1201247.0347847.7030844.55663

total of C1050.8202351.3376351.3561851.6379951.9657651.8798852.9652252.2969255.44337

selectivity

051030601202403601440

exo-THDCPD111111111

adamantane000000000


000000000

endo-THDCPD0.95852439080.92980918680.89437648980.83921585640.78850689380.74072877580.67789976140.63348262190.5094578486


selectivity of C7

051030601202403601440

C7-isomer1000000.01058621630.01399857720.0162545060.0225293071

n-heptane111110.98941378370.98600142280.9837454940.9774706929

C7isomer2000000000

951122

951128

silica gel 1.2g


12.8/1.0


051030601202403601440

C6-100.616441.4862.904813.334643.688463.944744.292674.91949

cyclohexane48.8867647.6969646.6398744.7205543.875543.1709342.3415841.7977739.13511

C6-2000000000

transDHN000000000

exoTHDCPD1.801859.9399524.646145.5273850.7207452.3500753.0315453.2424655.04865

adamantane00000.132850.1680.193860.220310.29411

endoTHDCPD49.3113941.7466527.228036.847261.936280.622540.488280.44680.41676

cisDHN000000000


000000000

total100100100100100.00001100100100.00001100

total of C648.8867648.313448.1258747.6253647.2101446.8593946.2863246.0904444.0546

total of C1051.1132451.686651.8741352.3746452.7898753.1406153.7136853.9095755.75952

selectivity

051030601202403601440

exo-THDCPD11110.9970.9970.9960.9960.991

adamantane00000.0030.0030.0040.0040.005

alkylTHDCPD000000000.003

000000000.0

endo-THDCPD0.9650.8080.5250.1310.0370.0120.0090.0080.007

conversion of endo-THDCPD0.0000.1630.4560.8640.9620.9880.9910.9910.992

selectivity of C7

051030601202403601440

C7-isomer100.01275919310.03087736390.06099292480.07063397820.07871335930.08522474890.09313580.111668021

n-heptane10.98724080690.96912263610.93900707520.92936602180.92128664070.91477525110.90686420.888331979

C7isomer2000000000

951205

951129



12.8/1.0


051030601202403601440

C6-19.335999.602139.66849.99510.176999.9941610.188279.236119.06484

cyclohexane44.111543.5047142.8311142.8538142.7063942.2647742.3153541.6360140.9434

C6-2000000000

transDHN0000000.1901300

exoTHDCPD12.2982525.4620335.0074940.1738642.1245744.0256944.7508446.9539349.19818

adamantane000000000

endoTHDCPD34.2542621.4311312.493016.977334.992053.715382.55542.173950.79358

cisDHN000000000


000000000

total100100100.0000110010010099.99999100100

total of C653.4474953.1068452.4995152.8488152.8833852.2589352.5036250.8721250.00824

total of C1046.5525146.8931647.500547.1511947.1166247.7410747.4963749.1278849.99176

selectivity

051030601202403601440

exo-THDCPD1111110.99611

adamantane000000000


000000000

endo-THDCPD0.73581983010.45702038420.26300796830.14797781350.10595093620.07782355950.05380200630.04425084090.0158742161

conversion of endo-THDCPD0.0000.3790.6430.7990.8560.8940.9270.9400.978

selectivity of C7

051030601202403601440

C7-isomer10.17467592960.1808077830.18416171880.18912440980.19244212450.19124310430.19404890560.18155543740.1812669272

n-heptane0.82532407040.8191922170.81583828120.81087559020.80755787550.80875689570.80595109440.81844456260.8187330728

C7isomer2000000000

951206

951130


12.8/1.0


051030601202403601440

C6-100.327340.713181.218171.661252.006522.52372.796482.90228

cyclohexane49.0623348.1608847.404746.4543245.5460445.0212643.8852143.9687339.65924

C6-2000000000

transDHN00.151570.168230.199650.12711000.129170

exoTHDCPD1.020636.4240414.6306526.422436.3510842.4541849.8061551.6791456.69727

adamantane000000000.15076

endoTHDCPD49.9170444.9361737.0832425.7054616.3145310.518043.784941.426470.59045

cisDHN000000000


000000000

total100100100100100.0000110010099.99999100

total of C649.0623348.4882248.1178847.6724947.2072947.0277846.4089146.7652142.56152

total of C1050.9376751.5117851.8821252.3275152.7927252.9722253.5910953.2347857.43848

selectivity

051030601202403601440

exo-THDCPD10.9769496670.98863224780.99250057750.9965154521110.99750677060.9973480172

adamantane000000000.0026519828


000000000

endo-THDCPD0.97996315890.87234745140.71475953570.49124179610.30902991930.19855765910.07062629250.02679582780.010279694


selectivity of C7

051030601202403601440

C7-isomer100.00675091810.01482151750.02555289220.03519053940.04266669620.05437964390.05979829880.0681902338

n-heptane10.99324908190.98517848250.97444710780.96480946060.95733330380.94562035610.94020170120.9318097662

C7isomer2000000000

951207

951204



12.8/1.0


051030601202403601440

C6-100.859581.197151.978782.654853.119533.315853.138583.10366

cyclohexane48.9543947.5257546.923145.6396444.3254443.7311542.2858241.6649939.5466

C6-2000000000

transDHN000000000

exoTHDCPD2.3568814.5835320.9400735.9285346.3332350.8328453.0446154.1349556.59709

adamantane0000000.126810.136120.15494

endoTHDCPD48.6887337.0311430.9396816.453056.686472.316481.226890.925350.5977

cisDHN000000000


000000000

total10010010010099.9999910099.9999899.9999999.99999

total of C648.9543948.3853348.1202547.6184246.9802946.8506845.6016744.8035742.65026

total of C1051.0456151.6146751.8797552.3815853.019753.1493254.3983155.1964257.34973

selectivity

051030601202403601440

exo-THDCPD1111110.99761507220.99749184970.9972698774

adamantane0000000.00238492780.00250815030.0027301226


000000000

endo-THDCPD0.9538279590.71745377820.59637295860.31409991830.12611293540.0435843770.02255382570.01676467420.0104220194


selectivity of C7

051030601202403601440

C7-isomer100.0177653020.02487829970.04155492770.05650986830.06658451920.07271334580.0700520070.0727700136

n-heptane10.9822346980.97512170030.95844507230.94349013170.93341548080.92728665420.9299479930.9272299864

C7isomer2000000000

951211 (2)

951122


12.8/1.0


051030601202403601440

C6-100.708461.029932.038772.742243.073473.506463.67454.55839

cyclohexane48.9637347.9265747.5021746.1190345.1917544.0857443.3317442.8894840.99688

C6-2000000000

transDHN000000000

exoTHDCPD2.6547813.9879420.7204938.8443247.3981151.2489352.5505652.9822854.0343

adamantane000000000

endoTHDCPD48.3814937.3770230.7474112.997894.667891.591860.611240.453740.41043

cisDHN000000000


000000000

total10099.99999100100.0000199.99999100100100100

total of C648.9637348.6350348.532148.157847.9339947.1592146.838246.5639845.55527

total of C1051.0362751.3649651.467951.8422152.06652.8407953.161853.4360254.44473

selectivity

051030601202403601440

exo-THDCPD111111111

adamantane000000000


000000000

endo-THDCPD0.94798248380.72767544260.59740945330.25072021430.08965332460.03012559050.01149772960.00849127610.0075384707


selectivity of C7

051030601202403601440

C7-isomer100.01456686670.02122162450.0423351980.05720867380.06517221130.07486325260.0789129280.1000628467

n-heptane10.98543313330.97877837550.9576648020.94279132620.93482778870.92513674740.9210870720.8999371533

C7isomer2000000000

951212

951205



12.8/1.0


051030601202403601440

C6-1000.316410.516750.735650.996011.459071.710672.35811

cyclohexane48.8170448.4709648.1618947.247246.6800746.3507845.4506444.9531140.98467

C6-2000000000

transDHN000000000

exoTHDCPD5.400139.9167514.7896619.8741524.3269128.8749436.5324140.6457753.15006

adamantane000000000

endoTHDCPD45.7818341.612336.7320432.3619128.2573723.7782716.5578912.690453.50716

cisDHN000000000


000000000

total99.999100.00001100100.00001100100100.00001100100

total of C648.8170448.4709648.478347.7639547.4157247.3467946.9097146.6637843.34278

total of C1051.1819651.5290551.521752.2360652.5842852.6532153.090353.3362256.65722

selectivity

051030601202403601440

exo-THDCPD111111111

adamantane000000000


000000000

endo-THDCPD0.89449153570.80755030410.712943090.61953198610.53737295630.45160152630.31188164320.23793305940.0619013781


selectivity of C7

051030601202403601440

C7-isomer1000.00652683780.01081882880.01551489670.02103648420.03110379490.03665948190.0544060626

n-heptane110.99347316220.98918117120.98448510330.97896351580.96889620510.96334051810.9455939374

C7isomer2000000000

951213

951206



12.8/1.0


051030601202403601440

C6-100.321070.499491.174241.617382.263963.022843.097653.61193

cyclohexane48.3789447.8325147.7753346.4442245.8203244.4962243.9031442.67740.39744

C6-2000000000

transDHN000000000

exoTHDCPD3.7626310.5422414.5165827.2643834.6394543.7310850.6717352.6930655.32634

adamantane00000000.117840.17428

endoTHDCPD47.8584441.3041937.208625.1171517.922869.508732.40231.414440.49002

cisDHN000000000


000000000

total100.00001100.0000110099.99999100.0000199.99999100.0000199.99999100.00001

total of C648.3789448.1535848.2748247.6184647.437746.7601846.9259845.7746544.00937

total of C1051.6210751.8464351.7251852.3815352.5623153.2398153.0740354.2253455.99064

selectivity

051030601202403601440

exo-THDCPD11111110.99776864250.9968598549

adamantane00000000.00223135750.0031401451


000000000

endo-THDCPD0.92711057710.79666410980.71935177410.47950393970.34098311130.17860187710.04526319180.02608448370.0087518199


selectivity of C7

051030601202403601440

C7-isomer100.00666762470.01034680190.02465934430.03409482330.0484164090.06441719490.06767173530.0820718406

n-heptane10.99333237530.98965319810.97534065570.96590517670.9515835910.93558280510.93232826470.9179281594

C7isomer2000000000

951214

951207



12.8/1.0


051030601202403601440

C6-100.260050.423050.924751.374272.087872.439172.552622.47798

cyclohexane48.5438347.7929847.4562246.1128245.6615843.8992842.7706142.5678538.47846

C6-2000000000

transDHN000000000

exoTHDCPD3.022738.6696412.3963522.2317930.3813245.3780451.7498353.0405658.16051

adamantane00000000.107490.13713

endoTHDCPD48.4334443.2773339.7243930.7306422.582838.634813.040391.731470.74592

cisDHN000000000


000000000

total100100100.0000110010010010099.99999100

total of C648.5438348.0530347.8792747.0375747.0358545.9871545.2097845.1204740.95644

total of C1051.4561751.9469752.1207452.9624352.9641554.0128554.7902254.8795259.04356

selectivity

051030601202403601440

exo-THDCPD11111110.99797753630.9976477607

adamantane00000000.00202246370.0023522393


000000000

endo-THDCPD0.94125621860.8331059540.76216089790.5802347060.42637954160.15986584670.05549147270.03155038530.0126333846


selectivity of C7

051030601202403601440

C7-isomer100.00541172950.00883576550.01965981660.02921750110.0454011610.05395226430.05657343550.0605028171

n-heptane10.99458827050.99116423450.98034018340.97078249890.9545988390.94604773570.94342656450.9394971829

C7isomer2000000000

951219

951211



12.8/1.0


051030601202403601440

C6-101.022141.387191.963982.560053.144443.73374.135794.95654

cyclohexane48.8569447.0562246.1667845.5989544.2297843.3858242.3726141.7183238.94598

C6-2000000000

transDHN000000000

exoTHDCPD1.8055318.095825.1865934.8014243.6210449.1378852.3881453.2398455.136

adamantane0000000.154350.188790.28805

endoTHDCPD49.3375333.8258527.2594417.635649.589134.331871.351210.596650.48099

cisDHN000000000

AlkylTHDCPD00000000.120620.19243

000000000

total100100.0000110099.99999100100.00001100.00001100.0000199.99999

total of C648.8569448.0783647.5539747.5629346.7898346.5302646.1063145.8541143.90252

total of C1051.1430651.9216552.4460352.4370653.2101753.4697553.893754.0252855.90504

selectivity

051030601202403601440

exo-THDCPD1111110.99706237750.99422195460.9913608341

adamantane0000000.00293762250.00352553960.0051792203

alkylTHDCPD00000000.00225250590.0034599457

000000000

endo-THDCPD0.96469648080.65147871840.51976174360.33632015220.18021235410.08101534040.02507176160.01101930160.0085741835


selectivity of C7

051030601202403601440

C7-isomer100.02125987660.02917085580.04129224170.05471381280.06757838880.08098023890.09019453220.1128987584

n-heptane10.97874012340.97082914420.95870775830.94528618720.93242161120.91901976110.90980546780.8871012416

C7isomer2000000000

951221

951212



12.8/1.0


051030601202403601440

C6-100.894541.437561.975082.583782.9783.721184.029845.15824

cyclohexane48.7368847.0757346.2029745.6946344.6349943.9184242.0142141.2484338.19846

C6-2000000000

transDHN000000000

exoTHDCPD2.3132815.1184624.5521332.9244941.4898446.2016652.0846553.5377555.53121

adamantane0000000.192290.233260.40941

endoTHDCPD48.9498436.9112627.8073419.405811.29146.901931.867430.814520.47449

cisDHN000000000

AlkylTHDCPD0000000.120250.136190.22819

000000000

total10099.99999100100100.00001100.00001100.0000199.99999100

total of C648.7368847.9702747.6405347.6697147.2187746.8964245.7353945.2782743.3567

total of C1051.2631252.0297252.3594752.3302952.7812453.1035954.1443754.5855356.41511

selectivity

051030601202403601440

exo-THDCPD1111110.9940.9930.989

adamantane0000000.0040.0040.007

alkylTHDCPD0000000.0020.0030.004

000000000

endo-THDCPD0.95487438140.70942645860.53108520770.370833030.21392828210.12997106220.03441339860.0148847660.0083768071


selectivity of C7

051030601202403601440

C7-isomer100.01864780.03017514710.04143259940.05471934150.0635016490.08136325060.08900163370.1189721542

n-heptane10.98135220.96982485290.95856740060.94528065850.9364983510.91863674940.91099836630.8810278458

C7isomer2000000000

951226

951213



12.8/1.0


051030601202403601440

C6-101.618252.842984.108654.959695.556336.512416.828816.42158

cyclohexane48.6883946.5451645.1852343.3793642.0009341.0661139.3841239.1825134.15184

C6-2000000000

transDHN000000000

exoTHDCPD1.3095223.2094839.2421249.9221652.1316852.4091452.9683352.7634557.05954

adamantane0000.185870.26090.316050.497510.575881.17277

endoTHDCPD50.0020928.6271112.729682.403960.646810.513880.426880.408430.45538

cisDHN000000000

AlkylTHDCPD000000.138480.210750.240930.7389

000000000

total100100100.00001100100.0000199.99999100100.00001100.00001

total of C648.6883948.1634148.0282147.4880146.9606246.6224445.8965346.0113240.57342

total of C1051.3116151.8365951.971852.5119953.0393953.2390753.8927253.7477658.68769

selectivity

051030601202403601440

exo-THDCPD1110.9960.9950.9910.9870.9850.968

adamantane0000.0040.0050.0060.0090.0110.020

alkylTHDCPD0000.0000.0000.0030.0040.0040.013

000000000

endo-THDCPD0.97447907010.55225681320.24493436830.04577925920.01219489890.00962726840.00789006690.0075651030.0076628997


selectivity of C7

051030601202403601440

C7-isomer100.03359915750.05919396120.08651973410.105613810.11917716020.14189329780.14841586810.1582706116

n-heptane10.96640084250.94080603880.91348026590.894386190.88082283980.85810670220.85158413190.8417293884

C7isomer2000000000

951226

10000

10000.4332799645

10000.7486509708

0.99629061450.0037093855000.9530218138

0.99502028720.0049797128000.9874857251

0.99140184550.0059785860.002619568400.9901206001

0.98680504850.00926865880.003926292600.9919032977

0.98475539310.01074798820.004496618700.9922367722

0.96758299520.01988716190.01252984300.9921364143

exo-THDCPD

adamantane

alkylTHDCPD

diTHDCPD


951227

951214

MMT 1.2g AlCl3 0.6g CH2Cl2 10ml


12.8/1.0


051030601202403601440

C6-1000000.465710.587670.703351.09332

cyclohexane47.1920547.1379447.0926946.5219845.8139344.8312544.7265943.9694441.23956

C6-2000000000

transDHN000000000

exoTHDCPD0.317460.476280.609050.875512.165465.180167.090529.2831717.18496

adamantane000000000

endoTHDCPD52.490552.3857852.2982652.6025152.0206149.5228847.5952246.0440340.37041

cisDHN000000000


000000000

total100.0000110010010010010010099.9999999.99999

total of C647.1920547.1379447.0926946.5219845.8139345.2969645.3142644.6727942.33288

total of C1052.8079652.8620652.9073153.4780254.1860754.7030454.6857455.327257.55537

selectivity

051030601202403601440

exo-THDCPD111111110.9935398082

adamantane000000000

alkylTHDCPD000000000.0064601918

000000000

endo-THDCPD0.99398840630.99099013550.98848835820.98362860110.96003659240.90530398310.87034060430.83221326940.7000595313


selectivity of C7

051030601202403601440

C7-isomer1000000.01028126390.01296876520.01574448340.0258267333

n-heptane111110.98971873610.98703123480.98425551660.9741732667

C7isomer2000000000

951227

10000

10000.4332799645

10000.7486509708

0.99629061450.0037093855000.9530218138

0.99502028720.0049797128000.9874857251

0.99140184550.0059785860.002619568400.9901206001

0.98680504850.00926865880.003926292600.9919032977

0.98475539310.01074798820.004496618700.9922367722

0.96758299520.01988716190.01252984300.9921364143

exo-THDCPD

adamantane

alkylTHDCPD

diTHDCPD


951228

10000

10000.0030164042

10000.0055333121

10000.0104224608

10000.0341571528

10000.0892207823

10000.1243956179

10000.1627535451

0.993539808200.006460191800.2957065425

exo-THDCPD

adamantane

alkylTHDCPD

diTHDCPD


960102

951219

SiO2 1.2g AlCl3 0.6g CH2Cl2 5ml


12.8/1.0


051030601202403601440

C6-1000000000.23916

cyclohexane48.6373247.8704847.511747.2143346.6777245.963145.4766844.86938.94375

C6-200.341820.399060.417670.42870.42830.304050.282330.24145

transDHN000000000

exoTHDCPD0.248220.239920.237610.24570.263220.286750.335040.386450.58596

adamantane000000000

endoTHDCPD51.1144651.5477851.8516352.122352.6303653.3218553.8842354.4622259.78268

cisDHN000000000


000000000

total100100100100100100100100100

total of C648.6373248.212347.9107647.63247.1064246.391445.7807345.1513339.42436

total of C1051.3626851.787752.0892452.36852.8935853.608654.2192754.8486760.36864

selectivity

051030601202403601440

exo-THDCPD111111110.7389527845

adamantane000000000

alkylTHDCPD000000000.2610472155

000000000

endo-THDCPD0.99516730820.99536723970.99543840530.99530820350.99502359270.99465104480.99382064720.99295425030.9869095894

conversion of endo-THDCPD0-0.0002009024-0.0002724136-0.00014157940.00014441350.00051877050.00135320070.00222380490.0082978197

selectivity of C7

051030601202403601440

C7-isomer1000000000.0060663001

n-heptane10.9929101080.99167076460.99123131510.99089932960.99076768540.99335855940.9937470280.9878093138

C7isomer200.0070898920.00832923540.00876868490.00910067040.00923231460.00664144060.0062529720.006124386

960102

10000

10000.4332799645

10000.7486509708

0.99629061450.0037093855000.9530218138

0.99502028720.0049797128000.9874857251

0.99140184550.0059785860.002619568400.9901206001

0.98680504850.00926865880.003926292600.9919032977

0.98475539310.01074798820.004496618700.9922367722

0.96758299520.01988716190.01252984300.9921364143

exo-THDCPD

adamantane

alkylTHDCPD

diTHDCPD


960102 (2)

10000

1000-0.0002009024

1000-0.0002724136

1000-0.0001415794

10000.0001444135

10000.0005187705

10000.0013532007

10000.0022238049

0.738952784500.261047215500.0082978197

exo-THDCPD

adamantane

alkylTHDCPD

diTHDCPD


960102 (3)

951221



12.8/1.0


051030601202403601440

C6-100.536070.817331.177151.768092.194143.374814.184396.01219

cyclohexane48.7058247.7318647.2713746.8024145.7906444.6863442.4893941.0441536.29005

C6-2000000000

transDHN000000000

exoTHDCPD1.501829.3319414.8523521.4431231.2228437.4737648.8129752.8409655.40049

adamantane00000000.312740.97513

endoTHDCPD49.7923642.4001337.0589530.5773221.2184315.645775.210951.456540.63508

cisDHN0000000.111880.161230.68706


000000000

total100100100100100100.00001100100.00001100

total of C648.7058248.2679348.088747.9795647.5587346.8804845.864245.2285442.30224

total of C1051.2941851.7320751.911352.0204452.4412753.1195354.0239254.6102457.0107

selectivity

051030601202403601440

exo-THDCPD1111110.99771322750.99110999490.9708708038

adamantane00000000.00586589910.0170887522


000000000

endo-THDCPD0.97072143470.81961015670.71388984670.58779433620.40461319870.29453893890.09625700550.0265930420.0110070131


selectivity of C7

051030601202403601440

C7-isomer100.0111061320.01699630060.02453440590.0371769810.04680284840.07358266360.09251658360.1421246251

n-heptane10.9888938680.98300369940.97546559410.9628230190.95319715160.92641733640.90748341640.8578753749

C7isomer2000000000

960102 (3)

10000

10000.4332799645

10000.7486509708

0.99629061450.0037093855000.9530218138

0.99502028720.0049797128000.9874857251

0.99140184550.0059785860.002619568400.9901206001

0.98680504850.00926865880.003926292600.9919032977

0.98475539310.01074798820.004496618700.9922367722

0.96758299520.01988716190.01252984300.9921364143

exo-THDCPD

adamantane

alkylTHDCPD

diTHDCPD


960104

10000

10000.1556690442

10000.2645780538

10000.3944768136

10000.5831829974

10000.6965772792

0.99771322750000.9008397238

0.99110999490.0058658991000.9726048679

0.97087080380.0170887522000.9886609972

exo-THDCPD

adamantane

alkylTHDCPD

diTHDCPD


960108

951226



12.8/1.0


051030601202403601440

C6-10.130050.776491.422522.424413.319524.447315.633526.035164.90074

cyclohexane50.5936547.208446.3147344.6553842.9158241.583739.7062538.8962639.64469

C6-2000000000

transDHN000000000

exoTHDCPD2.8137711.9502922.1505135.9454646.2057351.65853.3561153.8403254.07029

adamantane000000.239730.406530.516570.73508

endoTHDCPD46.4625340.0648230.1122416.974767.558932.071270.718160.492050.31608

cisDHN0000000.179440.219640.33312


000000000

total100100100100.00001100100.00001100.00001100100

total of C650.723747.9848947.7372547.0797946.2353446.0310145.3397744.9314244.54543

total of C1049.276352.0151152.2627552.9202253.7646653.96954.480854.8489455.12145

selectivity

051030601202403601440

exo-THDCPD111110.99538072280.98913705220.98651050190.9806269631

adamantane000000.00461927720.00753641680.00946505760.0133315221


000000000

endo-THDCPD0.94289810720.77025348980.57617021680.32076132710.14059290990.03837888420.01313861780.00893522220.0056998008


selectivity of C7

051030601202403601440

C7-isomer10.00256389030.01618196890.02979895160.05149576920.07179616280.09661552070.12425118170.13431936940.1100166729

n-heptane0.99743610970.98381803110.97020104840.94850423080.92820383720.90338447930.87574881830.86568063060.8899833271

C7isomer2000000000

960108

10000

10000.4332799645

10000.7486509708

0.99629061450.0037093855000.9530218138

0.99502028720.0049797128000.9874857251

0.99140184550.0059785860.002619568400.9901206001

0.98680504850.00926865880.003926292600.9919032977

0.98475539310.01074798820.004496618700.9922367722

0.96758299520.01988716190.01252984300.9921364143

exo-THDCPD

adamantane

alkylTHDCPD

diTHDCPD


960109

10000

10000.1830999724

10000.388936925

10000.6598133725

10000.8508927859

0.99538072280.0046192772000.9592968913

0.98913705220.0075364168000.9860657078

0.98651050190.0094650576000.9905236609

0.98062696310.0133315221000.9939550194

exo-THDCPD

adamantane

alkylTHDCPD

diTHDCPD


960109 (2)

951227



12.8/1.0


051030601202403601440

C6-101.485822.600353.904554.958555.81176.52086.909266.64772

cyclohexane48.2385546.6111745.2168543.133541.9077240.774739.5818538.007935.35148

C6-2000000000

transDHN000000000

exoTHDCPD2.6304823.4666537.4084348.5214151.7396952.3313952.6696653.5122254.20602

adamantane00000.241060.356910.550020.811162.04924

endoTHDCPD49.1309728.4363614.774374.440531.152980.567450.450350.439840.40877

cisDHN000000.157840.227320.319621.33677


000000000

total10010010099.9999910099.99999100100100

total of C648.2385548.0969947.817247.0380546.8662746.586446.1026544.9171641.9992

total of C1051.7614551.9030152.182852.9619453.1337353.2557553.6700354.7632256.66403

selectivity

051030601202403601440

exo-THDCPD11110.9953625140.99025945890.98545587220.9793060410.9412069691

adamantane00000.0046374860.00675375720.01029094240.01484471940.0355820067


000000000

endo-THDCPD0.94918071270.54787496910.2831271990.08384379420.02169958710.01062370080.00835569840.0079850640.0070476614


selectivity of C7

051030601202403601440

C7-isomer100.03089216190.05438105950.08300833050.10580210460.12475100030.14144089330.15382228080.1582820625

n-heptane10.96910783810.94561894050.91699166950.89419789540.87524899970.85855910670.84617771920.8417179375

C7isomer2000000000

960109 (2)

10000

10000.4332799645

10000.7486509708

0.99629061450.0037093855000.9530218138

0.99502028720.0049797128000.9874857251

0.99140184550.0059785860.002619568400.9901206001

0.98680504850.00926865880.003926292600.9919032977

0.98475539310.01074798820.004496618700.9922367722

0.96758299520.01988716190.01252984300.9921364143

exo-THDCPD

adamantane

alkylTHDCPD

diTHDCPD


960110

10000

10000.4227917173

10000.7017141254

10000.9116671956

0.9953625140.004637486000.9771386136

0.99025945890.0067537572000.9888075045

0.98545587220.0102909424000.9911969362

0.9793060410.0148447194000.9915874144

0.94120696910.0355820067000.9925750057

exo-THDCPD

adamantane

alkylTHDCPD

diTHDCPD


960111

951228



12.8/1.0


051030601202403601440

C6-100.2964500.185010.210560.221740.240550.588570.75675

cyclohexane49.0389547.3479448.1852848.1833947.5931347.9235447.1947146.7049546.02782

C6-2000000000

transDHN000000000

exoTHDCPD0.252154.610481.08851.421321.612762.201633.791125.8447712.38337

adamantane000000000

endoTHDCPD50.7088947.7451350.7262250.2102850.5835549.6530948.7736246.5974440.12376

cisDHN000000000


00000000.264270.7083

total99.99999100100100100100100100100

total of C649.0389547.6443948.1852848.368447.8036948.1452847.4352647.2935246.78457

total of C1050.9610452.3556151.8147251.631652.1963151.8547252.5647452.4422152.50713

selectivity

051030601202403601440

exo-THDCPD11111110.95674115740.9458968947

adamantane000000000


00000000.04325884260.0541031053

endo-THDCPD0.99505210250.91193914080.97899245620.97247189710.96910203040.95754234140.92787712830.88409318930.7539873304


selectivity of C7

051030601202403601440

C7-isomer100.006222138600.0038250180.00440468090.00460564360.00507112220.01244504530.0161752048

n-heptane10.993777861410.9961749820.99559531910.995394356

application of acidic ionic liquid on the catalyic green process...

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