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Chinese Journal of Chemical Engineering , 16(3) 394400 (2008)

Alternative Processing Technology for Converting Vegetable Oils and

Animal Fats to Clean Fuels and Light Olefins*

TIAN Hua (), LI Chunyi ()**, YANG Chaohe () and SHAN Honghong ()State Key Laboratory of Heavy Oil Processing, College of Chemistry & Chemical Engineering, China University ofPetroleum, Dongying 257061, China

Abstract Since the production cost of biodiesel is now the main hurdle limiting their applicability in some areas,catalytic cracking reactions represent an alternative route to utilization of vegetable oils and animal fats. Hence,catalytic transformation of oils and fats was carried out in a laboratory-scale two-stage riser fluid catalytic cracking(TSRFCC) unit in this work. The results show that oils and fats can be used as FCC feed singly or co-feeding withvacuum gas oil (VGO), which can give high yield (by mass)of liquefied petroleum gas (LPG), C 2C4 olefins, forexample 45% LPG, 47% C2C4 olefins, and 77.6% total liquid yield produced with palm oil cracking. Co-feedingwith VGO gives a high yield of LPG (39.1%) and propylene (18.1%). And oxygen element content is very low(about 0.5%) in liquid products, hence, oxygen is removed in the form of H 2O, CO and CO2. At the same time, highconcentration of aromatics (C7C9 aromatics predominantly) in the gasoline fraction is obtained after TSRFCC re-action of palm oil, as a result of large amount of hydrogen-transfer, cyclization and aromatization reactions. Addi-tionally, most of properties of produced gasoline and diesel oil fuel meet the requirements of national standards,containing little sulfur. So TSRFCC technology is thought to be an alternative processing technology leading to production of clean fuels and light olefins.Keywords vegetable oil, animal fat, renewable resource, biodiesel, two-stage riser fluid catalytic cracking technology

1 INTRODUCTION

Currently, many researchers are concentrating ondeveloping alternative and renewable sources of liquidfuels, which are new energy resources to replacecommercial petroleum products in the future. Becauseof suitable properties of vegetable oils and animal fats(triglycerides primarily, and negligible sulfur, nitrogenand heavy metal content), oils and fats have been

suggested as important sources for the production ofsynthetic fuels and useful chemicals [1]. At present,there are two promising processing technology of oilsand fats, i.e., liquid-phase catalyzed transesterification process for producing biodiesel at low temperature [2]and solid catalyzed catalytic cracking process for producing gasoline-like, diesel-like and light olefins athigh temperature [3].

Biodiesel is biodegradable and environmentally beneficial [2, 4]. The major obstacle to widespread useof biodiesel is the high cost relative to fossil feedstock[5, 6]. And biodiesel exhibits poor cold flow properties,which can be problematic for engine performance, andincreased NO x emission. The presence of oxygen low-ers the heat content as shown by the heating values of biodiesel, which are 9%13% lower than those of con-ventional diesel fuels on a mass basis and can alsocauses stability problems [7, 8].

Removal of oxygen, e. g . via pyrolysis or cata-lytic cracking, represents an alternative route for pro-duction of gasoline, diesel and light olefins, which haslower limit to feed source, higher yield of light oil andalkenes, and suitable product properties (negligiblesulfur, nitrogen, and metal content). So, vegetable oilsand animal fats may partially replace commercial pe-troleum products for the future.

The shape-selective pentasil HZSM-5 catalyst

was first used by Weisz et al . [9] to convert vegetableoils to hydrocarbons from 1970s. They achieved complete conversion of jojoba oil at 400°C over HZSM-5,whereas both castor and corn oils required a tempera-ture of 500°C for complete conversion. And then manytypes of catalysts such as HZSM-5, hydrogen-zeolite Y,silica-alumina, H-mordenite, and silica-alumina- pil-lared clay, were used at a temperature range of300500°C [3]. Over 95% (by mass) of the vegetable

oils were converted to liquid hydrocarbons in the gaso-line boiling range, light gases, and water [3, 10]. Theinfluence of properties of catalyst (mainly acidity and pore structure) on the conversion of animal fat andyields of products in a fixed-bed micro-reactor wasinvestigated by Tian et al . [11].

Generally speaking, besides fractionating pyrolysisreactor [1], fluidized bed reactor [12], laboratory-scaleonce-through microriser reactor [13] and transport riserreactor [14], the previous researches were principallyon cracking in fixed-bed micro-reactors. Higher yieldof liquid can be obtained in the products withfixed-bed reactor, but the olefinic content of gas product is much lower. Two-stage riser fluid catalyticcracking (TSRFCC) technology has the advantage ofcatalyst relay, staged reaction, optimum residence timeand great catalyst to oil ratio [1518]. In addition, thetechnologies are characterized by excellent flexibility,and various production goals can be achieved by ad- justing the operation scheme and reaction conditions.At the same time, catalytic cracking of vegetable oilsand animal fats has been investigated in experimentaland industrial TSRFCC unit by using Shenghua vac-uum gas oil (VGO) as main feedstock [19]. Hence,catalytic transformation of vegetable oils and animalfats solely or blending vacuum gas oil (VGO) werecarried out in the TSRFCC unit to produce clean fuels,

Received 2007-09-20, accepted 2008-03-25.* Supported by the Major Research Plan of PetroChina Company Limited (07-03D-01-01-02-02).

** To whom correspondence should be addressed. E-mail: [email protected]



Chin. J. Chem. Eng., Vol. 16, No. 3, June 2008 395

liquefied petroleum gas (LPG) and propylene in thiswork. The product distribution, oxygen distributionand main product quality (such as gasoline fuel, dieseloil fuel) was discussed.

2 EXPERIMENTAL

2.1 Materials

The feedstock includes vegetable oils (palm oiland soybean oil), animal fats (chicken fat), and VGO.Their properties are shown in Tables 13.

Table 1 Element composition anddensity of feeds and products

Element composition/% (by mass)Feed

H C O N S 20/kgm3

VGO 12.83 86.20 0.28 0.18 0.51 905.6chicken fat 11.78 75.80 12.42 0 0 920.0

palm oil 12.00 76.06 11.94 0 0 911.9

soybean oil 11.55 77.39 11.06 0 0 923.0

By difference.

Table 2 Distillation range of several feeds

Distillation temperature/°CFeed

IBP 10% 30% 50% 70% 90% FBP

VGO 340 400 437 460 495 540 548

chicken fat 353 495 539 556 571 585 589 palm oil 423 501 537 555 570 583 590

Tables 13 show that vegetable oils and animalfats are mainly composed of C, H and O, but none of

S and N. The saturated fatty acid content of palm oil ishigher than that of chicken fat, and much higher thanthat of soybean oil.

Because of certain oxygen content in feeds, theconversion of feed is defined as the sum of dry gas,LPG, gasoline, diesel oil, coke, CO, CO2, and H2Oyields in this article. The total liquid includes LPG,gasoline and diesel oil.

2.2 Experimental setup

In this work, most of the experiments were con-ducted in a laboratory-scale XTL-5 TSRFCC unit(Fig. 1). In TSRFCC, fresh feedstock is injected intothe 1st stage riser, and recycling oil (including gaso-line and heavy oil) from the fractionator is injectedinto the 2nd stage one [18]. The two risers share thecommon disengager and regenerator. Thus, the freshfeedstock and the recycling oil, having different ad-sorption and reaction properties, all contact the regen-

erated catalyst with high activity and can react respec-tively under the most favorable conditions. Further-more, the lengths of the two risers are different andmuch shorter than that of the conventional FCC riser[18]. The feed capacity is about 12 kg, and other de-tails are the same as Ref. [22].

Figure 1 Schematic representation of the two-stage riser fluid catalytic cracking unit

Table 3 Fatty acid composition of several feeds

Fatty acid/% (by mass)Feed [20,21]

Palmitic Palmitoleic Stearic Oleic Linoleic Linolenic

chicken fat 20 6.2 5.3 39.6 24.7 1.3

palm oil 35 6 44 15

soybean oil 14 4 24 52 6



Chin. J. Chem. Eng., Vol. 16, No. 3, June 2008396

2.3 Materials

The catalysts were the mixture of CORH andLTB-2 catalyst. CORH catalyst for reducing olefincatalyst is produced by Catalyst Plant of ChanglingPetrochemical Company, and the active component ismainly Ultra-Y (USY) zeolite. LTB-2 catalyst formaximizing propylene is developed based upon thespecial features of TSRFCC, and the active compo-

nent contains Zeolite Socony Mobile-Five (ZSM-5)zeolite primarily [23]. And their main physical proper-ties are listed in Table 4. The particles of catalysts areabout 88180 m.

2.4 Analysis

Varian 3800 C gas chromatography (Varian,America) were used to determine hydrocarbon composition and H2, N2, CO and CO2 content of crackinggas products and flue gas produced from burning theready-to-regeneration catalyst in high-temperature air.Group composition of gasoline was analyzed by HP5890 gas chromatography (HP Co., USA). The frac-tions of liquid product analysis were performed onAgilent Technologies 6890 N gas chromatographyapparatus (Agilent Technologies, USA). Thermo Nicolet Nexue FT-IR spectrum apparatus (ThermoElectron Co., USA) was employed to determine func-tional group of organic liquid product.

3 RESULTS AND DISCUSSION

3.1 Conversion and product distribution

At present, generalization and application of theTSRFCC technology has been successfully in many

oil refinery enterprises. The fact that TSRFCC canimprove liquid yield and reduce dry gas has been evi-denced by more than 10 commercial units [18, 24, 25].Firstly, catalytic cracking of pure vegetable oils (palmoil and soybean oil), animal fats (chicken fat), or blending VGO was carried out in TSRFCC equipmentoperated at atmospheric pressure, the 1st stage riserreaction temperature of 500°C, mass ratio of cata-lysts/feed of 6 and residence time of about 1.4 s; the

2nd stage riser reaction temperature of 520°C, massratio of catalysts/feed of 8 and residence time of about1.7 s. The catalysts were the mixture of CORH andLTB-2 catalyst. The conversion of feed and productdistribution is presented in Table 5.

As expected, vegetable oils and animal fats can be easily transformed, the conversion is exceptionallyhigh and can reach over 95% (mass fractionas-received), agreed with the previous conclusions [3,10, 26, 27], and the cracking products consist of dry gas,LPG, gasoline, diesel oil, heavy oil, and so on. Thefinding that only less than 5% heavy oil is left after asingle pass cracking reaction demonstrates the secon-dary cracking reaction of gasoline is dominant in the

2nd stage riser.In the laboratory, vegetable oils and animal fatscan be used as FCC feed solely, which gives highyield of LPG and light olefins, and high yield of gaso-line fraction. It can be observed that, palm oil crackingcan even give a LPG yield of 45%, especially high propylene (23%) and butylenes (17.8%), and totalliquid of 77.6%. Although the yield of dry gas is highfor palm oil, the concentration of ethylene in dry gasis very high (87.1%), i.e., the recovery of ethylene isrelatively important. At the same time, C2C4 olefinsyield (47%) is much higher than 25.8% reported byKatikaneni when catalytic conversion of canola oil

was investigated in a fixed-bed micro-reactor [27]. Thereason is that the secondary cracking reactions are

Table 4 Main physical properties of several FCC equilibrium catalysts

Granularity/% (by volume)Catalyst

Al2O3 content/%(by mass)

Pore volume/cm3·g1

BET surface area/m2·g1 Attrition index

Apparent density/kg·m3

040 m 0149 m

CORH 49.8 0.40 251 1.5 720 19.6 94.5

LTB-2 48.6 0.26 211 2.1 740 4.2 95.3

Table 5 Overall product distribution of TSRFCC (%, by mass)

Product distribution Yields of C2C4 olefinsFeed Style Conversion Light oil Total liquid

Dry gas LPG Gasoline Diesel oil Heavy oil Coke Ethylene Propylene Butylenes

chicken fat 1st riser 97.05 44.15 78.49 4.48 34.34 32.75 11.40 2.95 2.31 3.68 16.35 15.18

1st riser 98.03 37.04 78.60 6.35 41.56 28.14 8.90 1.97 2.20 5.53 21.00 16.60 palm oil

total 98.33 32.54 77.57 7.19 45.03 21.03 11.51 1.67 2.66 6.22 22.99 17.77

1st riser 95.50 47.65 76.89 4.59 29.24 32.37 15.28 4.50 3.98 3.53 14.71 12.39soybean oil

total 96.25 37.91 74.71 6.22 36.79 22.93 14.98 3.75 5.22 4.78 18.82 15.25

1st riser 91.21 43.82 78.68 5.16 34.86 29.04 14.78 8.79 2.80 4.16 16.25 13.9150% palmoil+50% VGO total 93.92 40.16 79.22 6.08 39.06 20.91 19.25 6.08 3.99 4.87 18.13 15.73

T 1500°C, R16, t 11.4 s; T 2520°C, R28, t 21.7 s.




terminated in time by TSRFCC technology, so theyield of light oil reaches a high level [18]. On the otherhand, ZSM-5 zeolite catalyst is good for the produc-tion of light olefins, agreed with the previous conclu-sions [28], and similar to petroleum-based feeds [29, 30].

Moreover, LPG and light olefin yields of palm oilare the highest among three feeds. The fatty acidcompositions are different, such as more palmitic andstearic acid in palm oil. Dupain et al . [13] performedcatalytic cracking experiments in a laboratory-scaleonce-through microriser reactor on rapeseed oil in thetemperature range of 485585°C. The authors statedthat the relatively high number of double bonds in themolecule enhanced the formation of aromatics. In thiswork, the content of saturated fatty acids increasesfrom soybean oil to chicken fat and palm oil, i.e., thenumber of double bonds in the molecule decreases(the content of unsaturated fatty acid decreasing), theformed olefins are reserved to some extent, so high

light olefins and LPG yield can be obtained.On the other hand, vegetable oil co-feeding withVGO (the ratio is 11) gives LPG yield of 39.1%,ethylene 4.9%, propylene 18.1%, butylenes 15.7%,and total liquid yield of 79.2%. That is to say, vegetable oils and animal fats can also co-feed with VGO forthe production of gasoline, LPG and light olefins.

3.2 Oxygen distribution

Different from conventional catalytic cracking of petroleum-based feeds, cracking of vegetable oils andanimal fats containing about 12% oxygen would pro-duce some H2O, CO and little CO2, oxygen distribu-tion in the product is listed in Table 6. As shown, H2Ois primary in deoxygenated products whatever thetype of vegetable oils and animal fats is. It is worthyof noting that the oxygen atoms from the rapeseed oiland canola oil are expelled mostly as H2O and partlyas oxides of carbon [13, 28]. On the other hand, H2O,CO and CO2 are hardly existed in the 2nd stage riserof TSRFCC with vegetable oils and animal fatscracking solely. Hence, cleavages of carbonyl groupand ester group have been completely in the 1st stageriser, and reactions of the 2nd stage riser have littlerelation with oxygen.

This is further confirmed from the elementanalysis of liquid products from palm oil presented inTable 7. It is shown that oxygen content of liquid products are relatively low (0.32%0.58%) after asingle pass cracking reaction of TSRFCC, i.e., oxygenelement of products is present predominantly in the

form of H2O, CO and CO2, and the oxygen contents inH2O, CO, CO2 account for 70.6%75.6% of the totaloxygen content (feeds).

3.3 Product quality

Research on pyrolysis of vegetable oils and ani-mal fats is very comprehensive; however, research onthe properties of products is not as common [8].

Group composition of gasoline is shown in Table 8.As seen, the concentration of aromatics, olefins andi-alkanes in the first-gasoline (after reaction in the 1ststage riser of TSRFCC) is predominant in despite ofthe type of feeds. However, the concentration of aro-matics in the second-gasoline (after reaction in the 2ndstage riser of TSRFCC) increases remarkably, but theconcentration of olefins decreases markedly, and theconcentration of n-alkanes, i-alkanes reduces a little.

On the other hand, the concentrations of varioushydrocarbons differ from different feedstock. For ex-ample, for palm oil and chicken fat, the sum of theconcentrations of aromatics and olefins in the

first-gasoline are 83.2%, 84%, respectively, in whichC5, C6 olefins and C7, C8, C9 aromatics limited by poreare dominant [3]. Idem et al . stated that cyclic specieswere formed through Diels-Alder reactions and upondehydrogenation formed mainly C7-C9 aromatics [3].Additionally, the concentration of aromatics in the

Table 6 Oxygen distribution of TSRFCC (%, by mass)

Feed Style CO CO2 H2O

chicken fat 1st riser 2.93 0.85 7.99

1st riser 3.49 0.79 6.60 palm oil

total 3.51 0.80 6.601st riser 1.77 0.64 7.63soybean oil

total 1.83 0.65 7.63

T 1500°C, R16, t 11.4 s; T 2520°C, R28, t 21.7 s.

Table 7 Element composition and density of feeds andproducts

(%, by mass)

Product H C O N S

gasoline 10.64 89.04 0.32 0 0

diesel oil 9.26 90.16 0.58 0 0

heavy oil 7.38 92.04 0.42 0 0.16 T 1500°C, R16, t 11.4 s; By difference.

Table 8 Group composition of gasoline produced by different feeds

Feed Style Aromatic C7 C8 C9 Olefin C5 C6 n-Alkane i-Alkane Naphthene

chicken fat 1st riser 41.94 11.32 15.63 8.52 42.02 23.00 9.70 2.58 8.98 4.17

palm oil 1st riser 48.05 12.45 17.20 7.37 35.19 21.42 7.45 2.46 9.80 4.23

2nd riser 82.71 24.88 32.85 13.65 6.25 2.36 2.11 1.33 5.19 4.34

1st riser 39.74 8.67 12.72 8.71 35.64 20.09 7.53 3.89 13.67 6.5050% palm oil+50% VGO 2nd riser 67.94 16.49 25.32 14.89 10.39 4.09 1.86 3.20 10.48 7.72

T 1500°C, R16, t 11.4 s; T 2520°C, R28, t 21.7 s.




second-gasoline can reach 82.7% for palm oil, and theconcentration of olefins is only 6.3% left. In otherwords, secondary cracking of the resulting C5C8 ole-fins produced by reaction in the 1st stage riser intoaromatics appears to be primary for the reaction in the2nd stage riser of TSRFCC. The produced aromaticscan be used to yield toluene and xylenes by extraction,separation and purification, and residual gasoline can be mixed straight-run gasoline. After blending VGO,aromatics are also predominant in the second-gasoline.

Two possible reasons exist for high concentrationof aromatics in the gasoline for vegetable oils andanimal fats. It may contain aryl groups in the structureof vegetable oils and animal fats which remain after breaking. On the other hand, aromatics are produced by hydrogen-transfer, cyclization and aromatizationreactions. Take the reaction of palm oil for examples,FT-IR spectra of feed and first-gasoline product are presented in Fig. 2.

FT-IR spectra show that there are no aryl groupsin feed (palm oil), and they contain mainly stretchingvibration peak of ester group, situated 1748 cm1

(C O) because of the electrophilic effect of oxygenelement [31] and 1165 cm1 (C O), respectively.

Namely, high concentration of aromatics in the gaso-line is as a result of large amount of hydrogen-transfer,cyclization and aromatization reactions. After the 1ststage riser of TSRFCC, the peaks of C O and C O bond disappear largely. However, aromatics and ole-fins are dominant, in which stretching vibration peaksare at 1604 cm1, 1517 cm1 and 1500 cm1. At thesame time, the peak of 1026 cm1 shows that a littlealcohol may exist in the gasoline product.

The properties of gasoline fuel and diesel oil fuel produced from catalytic cracking of vegetable oils andanimal fats have also been studied in this work. Tables 9and 10 list the main properties of gasoline and dieseloil after reaction of chicken fat in the 1st stage riser,respectively.

As shown, the produced gasoline possesses ac-ceptable amounts of gum, sulfur, aromatics, benzene,oxygen, and gives acceptable distillation range. The

Figure 2 FT-IR spectra of palm oil and first-gasoline after the 1st stage riser of TSRFCC

(T 1500°C, R16, t 11.4 s)

Table 9 The properties of gasoline after reaction in the 1ststage riser of chicken fat

Property Value GB17930-2006

RON/min 95.6 93

10% recovered 61 70distillationtemperature/°C 50% recovered 105 120

90% recovered 165 190

final boiling point 190 205

gum/mg·(100ml)1 3 5

induction period/min 132 480sulfur/% (by mass) 0 0.05

copper strip corrosion (50°C, 3 h) 1 1

benzene/% (by volume) 1.75 2.5

aromatics/% (by volume) 28.19 40

olefins/% (by volume) 41.24 35

oxygen/% (by volume) 2.11 2.7

T 1500°C, R16, t 11.4 s.

Table 10 The properties of diesel oil after reaction ofchicken fat in the 1st stage riser

Property Value GB252-2000

color 2.5 3.5

oxidation stability/mg·(100 ml) 1 2.1 2.5

sulfur/% (by mass) 0 0.2

acidity/mg KOH·(100 ml)1 1.9 7

carbon residue/% (by mass) 0.44 0.3

ash/% (by mass) 0.002 0.01

copper strip corrosion (50°C, 3 h) 1 1

kinematic viscosity/mm2·s1 3.91 3.07.0

solidifying point/°C 30 No.20 diesel

closed flash point/°C 72 45

cetane index/min 31.5 45

distillation 50% recovered 260 300temperature/°C 90% recovered 320 355

95% recovered 332 365

T 1500°C, R16, t 11.4 s.




research octane number (RON) can be 95.6, and meetsthe standard of No. 93 gasoline. However, it has un-acceptable copper strip corrosion values and induction period (GB17930-2006), due to the effect of residualoxygen in the gasoline. At the same time, the concen-tration of olefins would be reduced if more propor-tional catalytic pyrolysis catalysts were used by pro-moting more cyclization and aromatization reactions.Weisz et al . [9] also find that the RON of gasoline is9096 after catalytic pyrolysis of several vegetable oils.

On the other hand, the produced diesel oil pos-sesses acceptable amounts of sulfur, ash, and givesacceptable color, oxidation stability, acidity, copperstrip corrosion values, kinematic viscosity, and distil-lation range. The solidifying point is lower than 30,and meets the standard of No. 20 diesel oil. But ithas unacceptable carbon residue and cetane index (CI)(GB 252-2000). The cetane number is also determinedfor the pyrolysis products of soybean oil, palm oil, and

castor oil by Lima et al . The castor oil is the only oilwhose thermal cracking products exhibited a lowercetane value than the specified ASTM value of 40 [21].The reason is that there are no aromatics in the products.

That is to say, most of properties of producedgasoline fuel and diesel oil fuel meet the requirementsof national standards, containing little sulfur aftercatalytic cracking of vegetable oils and animal fats.

4 CONCLUSIONS

TSRFCC technology is an alternative processingtechnology leading to production of clean fuels andlight olefins. So vegetable oils (palm oil and soybeanoil) and animal fats (chicken fat) were used as FCCfeed solely or blending VGO in the laboratory-scaleTSRFCC unit.

For palm oil cracking solely, the conversion offeed can reach over 97%, at the same time, 45% LPG,23% propylene, and 77.6% total liquid are produced.And the LPG and light olefins yields of palm oil arethe highest in the three feeds. Oxygen content of liq-uid products is very low (about 0.5%), so the oxygenatoms are expelled mostly as H2O and partly as oxidesof carbon. After blending VGO in palm oil, the LPGyield can reach 39.1%, propylene yield is 18.1%, and

total liquid yield is 79.2%.Additionally, the sum of aromatics and olefinsconcentrations in the first-gasoline are about 83.6%for vegetable oil and animal fat, which C5, C6 olefinsand C7, C8, C9 aromatics are predominant. However,the concentration of aromatics in the second-gasolinecan be 82.7% for palm oil, and olefins concentration isonly 6.3% left after TSRFCC reactions. FT-IR spectrashow that there are no aryl groups in feed, so higharomatics concentration is as a result of large amountof hydrogen-transfer, cyclization and aromatizationreactions. At the same time, most of properties of produced gasoline and diesel oil fuel meet the re-quirements of national standards, containing little sul-fur after catalytic cracking of vegetable oils and ani-mal fats. It is suggested that vegetable oils and animalfats may become renewable resources producing cleanfuels and light olefins to partially replace commercial

petroleum products in the future.

NOMENCLATURE

R1 mass ratio of catalysts/feed of 1st stage riser

R2 mass ratio of catalysts/feed of 2nd stage riserT 1 reaction temperature of 1st stage riser, °CT 2 reaction temperature of 2nd stage riser, °Ct 1 residence time of 1st stage riser, st 2 residence time of 2nd stage riser, s 20 standard density at 20°C, kgm3

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