13

HYDROGENATION OF ALDEHYDES （ｱﾙﾃﾞﾋﾄﾞの水素化）

O OH

n-Butanal n-ﾌﾞﾀﾅｰﾙ

（n-ﾌﾞﾁﾙｱﾙﾃﾞﾋﾄﾞ）

n-Butanol n-ﾌﾞﾀﾉｰﾙ 用途：塗料溶剤等

O

OH

2-Ethylpent-2-enal 2-ｴﾁﾙﾍﾟﾝﾄ-2-ｴﾅｰﾙ

2-Ethylpentanol 2-ｴﾁﾙﾍﾟﾝﾀﾉｰﾙ

OO

OH

OHHO

OH

2-Hydroxypentanedial 2-ﾋﾄﾞﾛｷｼﾍﾟﾝﾀﾝｼﾞｱﾙ

Pentane-1,2,5-triol ﾍﾟﾝﾀﾝ-1,2,5-ﾄﾘｵﾙ

（1,2,5-ﾄﾘﾋﾄﾞﾛｷｼﾍﾟﾝﾀﾝ）

O

OH

Benzaldehyde ﾍﾞﾝｽﾞｱﾙﾃﾞﾋﾄﾞ

4-Hydroxy-benzaldehyde 4-ﾋﾄﾞﾛｷｼ-ﾍﾞﾝｽﾞｱﾙﾃﾞﾋﾄﾞ

Anisaldehyde ｱﾆｽｱﾙﾃﾞﾋﾄﾞ

（4-ﾒﾄｷｼ-ﾍﾞﾝｽﾞｱﾙﾃﾞﾋﾄﾞ）

Benzylic alcohol ﾍﾞﾝｼﾞﾙ ｱﾙｺｰﾙ 用途：ｸﾘｰﾑ香料等

4-Hydroxy-benzylic alcohol 4-ﾋﾄﾞﾛｷｼ-ﾍﾞﾝｼﾞﾙ ｱﾙｺｰﾙ

Anisalcohol ｱﾆｽｱﾙｺｰﾙ

（4-ﾒﾄｷｼ-ﾍﾞﾝｽﾞｱﾙｺｰﾙ）

O

OH

Cinnamic aldehyde

ｼﾝﾅﾐｯｸ ｱﾙﾃﾞﾋﾄﾞ Cinnamic alcohol

ｼﾝﾅﾐｯｸ ｱﾙｺｰﾙ （ﾌｪﾆﾙｱﾘﾙｱﾙｺｰﾙ、ｼﾝﾅﾐﾙｱﾙｺｰﾙ、用途：香付け）

H2

H2

H2

H2

H2

H2

H2

14

OHO

OHHO

Hydroxypivaldehyde

ﾋﾄﾞﾛｷｼﾄﾘﾒﾁﾙｱｾﾄｱﾙﾃﾞﾋﾄ （2,2-ｼﾞﾒﾁﾙ-3-ﾋﾄﾞﾛｷｼﾌﾟﾛﾊﾞﾅｰﾙ）

Neopentyl glycol ﾈｵﾍﾟﾝﾁﾙ ｸﾞﾘｺｰﾙ

（2,2-ｼﾞﾒﾁﾙ-3-ﾌﾟﾛﾊﾟﾉｰﾙ 用途：ｱﾙｷｯﾄﾞ樹脂塗料等）

O

OH

Cinnamic aldehyde

ｼﾝﾅﾐｯｸ ｱﾙﾃﾞﾋﾄﾞ

α-Methyl cinnnamic aldehyde α-ﾒﾁﾙ ｼﾝﾅﾐｯｸ ｱﾙﾃﾞﾋﾄﾞ

3-Phenyl-propanol 3-ﾌｪﾆﾙ-ﾌﾟﾛﾊﾟﾉｰﾙ 用途：香り付け

2-Methyl-3-phenyl-propanol 2-ﾒﾁﾙ-3-ﾌｪﾆﾙ-ﾌﾟﾛﾊﾟﾉｰﾙ

用途：食品用香り付け

H2

H2

H2

15

HYDROGENATION OF ALDEHYDES （ｱﾙﾃﾞﾋﾄﾞの水素化）

OH

OO

OH

O Ethyl Vanilin ｴﾁﾙ ﾊﾞﾆﾘﾝ

（3-ｴﾄｷｼ-4-ｵｷｼﾍﾞﾝｼﾞﾙｱﾙﾃﾞﾋﾄﾞ）

2-Ethoxy-4-methylphenol 2-ｴﾄｷｼ-4-ﾒﾁﾙﾌｪﾉｰﾙﾞ 用途：香料

O

OH

Dehydrobrahmanal

ﾃﾞﾋﾄﾞﾛﾌﾞﾗﾏﾅｰﾙ Dehydrobrahmanol

ﾃﾞﾋﾄﾞﾛﾌﾞﾗﾏﾉｰﾙ

OO

O

OH

Furfural ﾌﾙﾌﾗｰﾙ

（ﾌﾙﾌﾘﾙ ｱﾙﾃﾞﾋﾄﾞ）（2-ﾌﾗﾝｱﾙﾃﾞﾋﾄﾞ）

Furfurylic alcohol ﾌﾙﾌﾘﾙ ｱﾙｺｰﾙ （2-ﾌﾗﾝﾒﾀﾉｰﾙ、

用途：ﾌﾗﾝ樹脂原料）

OH OH OH

OHOH O

OH OH OH

OHOH OH

D-Glucose

D-ｸﾞﾙｺｰｽ（ﾌﾞﾄﾞｳ糖） D-Sorbitol

D-ｿﾙﾋﾞﾄｰﾙ （糖ｱﾙｺｰﾙ、用途：食品等）

OH OH O

OHOH

OH OH OH

OHOH

D-Xylose

D-ｷｼﾛｰｽ （ｳｯﾄﾞｼｭｶﾞｰ） Xylitol

ｷｼﾘﾄｰﾙ 用途：医薬品等

O

OH OH

HO

OH O O OH

OHOH

HO

O

OH OH

HO

OH O

OHOH

HO

OH

OH

Lactose

ラクトーゼ Lactitol

ﾗｸﾁﾄｰﾙ

H2

H2

H2

H2

H2

H2

16

OHO

OHO

O

（2 糖ｱﾙｺｰﾙ 用途：医薬品等）

HYDROGENATION OF ALDEHYDES （ｱﾙﾃﾞﾋﾄﾞの水素化）

Palatinose ﾊﾟﾗﾁﾉｰｾﾞ

Palatinitol ﾊﾟﾗﾁﾆﾄｰﾙ、用途：甘味料等

(-)-Menthone ﾒﾝﾄｰﾈ

(-)-Menthol ﾒﾝﾄｰﾙ 用途：医薬品等

3-Hydroxypropionaldehyde 3-ﾋﾄﾞﾛｷｼﾌﾟﾛﾋﾟｵﾝｱﾙﾃﾞﾋﾄﾞ

Propane-1,3-diol ﾌﾟﾛﾊﾟﾝ-1,3-ｼﾞｵｰﾙ 用途：医薬・農薬中間体

Methyl-3-Hydroxypropionate ﾒﾁﾙ-3-ﾋﾄﾞﾛｷｼﾌﾟﾛﾋﾟｵﾈｰﾄ

Propane-1,3-diol ﾌﾟﾛﾊﾟﾝ-1,3-ｼﾞｵｰﾙ 用途：医薬・農薬中間体

OHHO

OHHO

O OHH2

H2

H2

H2

17

HYDROGENATION OF ALIPHATIC NITRO-COMPOUNDS（脂肪族ﾆﾄﾛ化合物の水素化）

OHHO

NO2

OHHO

NH2

2-Nitropopane-1,3-diol 2-ﾆﾄﾛﾌﾟﾛﾊﾟﾝ-1,3-ｼﾞｵｰﾙ

2-Aminopropane-1,3-diol 2-ｱﾐﾉﾌﾟﾛﾊﾟﾝ-1,3-ｼﾞｵｰﾙ

OH

NO2

OH

NH2

2-Nitrobutanol 2-ﾆﾄﾛﾌﾞﾀﾉｰﾙ

2-Aminobutanol 2-ｱﾐﾉﾌﾞﾀﾉｰﾙ

OH

NO2

HO

OH

NH2

HO

2-Nitro-2-methylpropane-1,3-diol

2-ﾆﾄﾛ-2-ﾒﾁﾙﾌﾟﾛﾊﾟﾝ-1,3-ｼﾞｵｰﾙ 2-Amino-2-methylpropane-1,3-diol

2-ｱﾐﾉ-2-ﾒﾁﾙﾌﾟﾛﾊﾟﾝ-1,3-ｼﾞｵｰﾙ

OH

NO2

OH

NH2

2-Nitro-2-methylpropanol

2-ﾆﾄﾛ-2-ﾒﾁﾙﾌﾟﾛﾊﾟﾉｰﾙ

2-Amino-2-methylpropanol 2-ｱﾐﾉ-2-ﾒﾁﾙﾌﾟﾛﾊﾟﾉｰﾙ

N-Ethyl-2-(nitromethylene)-pyrrolidine N-ｴﾁﾙ-2-(ﾆﾄﾛﾒﾁﾚﾝ)-ﾋﾟﾛﾘﾃﾞｨﾝ

1-(1- Ethyl pyrrolidine2-ylidene)methanamin 1-(1- ｴﾁﾙﾋﾟﾛﾘﾃﾞｨﾝ-2-ｲﾘﾃﾞﾝ)ﾒｻﾅﾐﾝ

NO2

HO

OH

HO

NH2

HO

OH

HO Tris-(hydroxymethyl)-nitromethane

ﾄﾘｽ-(ﾋﾄﾞﾛｷｼﾒﾁﾙ)-ﾆﾄﾛﾒﾀﾝ Tromethamine

ﾄﾛﾒｻﾐﾝ （ﾄﾘｽ-(ﾋﾄﾞﾛｷｼﾒﾁﾙ)-ｱﾐﾉﾒﾀﾝ）

H2

H2

H2

H2

H2

H2

18

1,3-Dimethyl-4-amino-5- nitrosouracil 1,3-ｼﾞﾒﾁﾙ-4-ｱﾐﾉ-5- ﾆﾄﾛｿｳﾗｼﾙ

1,3-Dimethyl-4,5- diaminouracil 1,3-ｼﾞﾒﾁﾙ-4,5- ｼﾞｱﾐﾉｳﾗｼﾙ

MeO

NO2

OH

MeO

NH2

OH

1-(p-Methoxyphenyl)-2-nitroethanol

1-(p-ﾒﾄｷｼﾌｪﾆﾙ)-2-ﾆﾄﾛｴﾀﾉｰﾙ 1-(p-Methoxyphenyl)-2-aminoethanol

1-(p-ﾒﾄｷｼﾌｪﾆﾙ)-2-ｱﾐﾉｴﾀﾉｰﾙ 用途：医薬品等

N-Benzyl-6-Nitro[3,1,0]-3-Azabicyclohexan N-ﾍﾞﾝｼﾞﾙ-6-ﾆﾄﾛ[3,1,0]-3-ｱｽﾞﾊﾞｲｼｸﾛﾍｷｻﾝ

N-Benzyl-6-Amino-[3,1,0]-3-Azabicyclohexan

N-ﾍﾞﾝｼﾞﾙ-6-ｱﾐﾉ[3,1,0]-3-ｱｽﾞﾊﾞｲｼｸﾛﾍｷｻﾝ

H2

H2

H2

19

HYDROGENATION OF AROMATIC NITRO-COMPOUNDS（芳香族ﾆﾄﾛ化合物の水素化）

NO2

NH2

1-Methyl-2-nitrobenzene 1-ﾒﾁﾙ-2-ﾆﾄﾛﾍﾞﾝｾﾞﾝ

o-Toluidine ｵﾙﾄ-ﾄﾙｲﾃﾞｨﾝ

NO2

NH2

1-Methyl-3-nitrobenzene m-Toluidine 1-ﾒﾁﾙ-3-ﾆﾄﾛﾍﾞﾝｾﾞﾝ

ﾒﾀ-ﾄﾙｲﾃﾞｨﾝ

NO2

NO2

NH2

NH2

2,4-Dinitrotoluene 2,4-ｼﾞﾆﾄﾛﾄﾙｴﾝ

（1-ﾒﾁﾙ-2,4-ｼﾞﾆﾄﾛﾍﾞﾝｾﾞﾝ）

2,4-Diaminotoluene 2,4-ｼﾞｱﾐﾉﾄﾙｴﾝ

（1-ﾒﾁﾙ-2,4-ｼﾞｱﾐﾉﾍﾞﾝｾﾞﾝ） 用途：ﾎﾟﾘｳﾚﾀﾝ樹脂原料等

O2N

H2N

1-Methyl-4-nitrobenzene p-Toluidine 1-ﾒﾁﾙ-4-ﾆﾄﾛﾍﾞﾝｾﾞﾝ

ﾊﾟﾗ-ﾄﾙｲﾃﾞｨﾝ

NO2

OEt

NH2

OEt

1-Ethoxy-2-nitrobenzene 2-Ethoxyaniline 1-ｴﾁﾙ-2-ﾆﾄﾛﾍﾞﾝｾﾞﾝ 2-ｴﾄｷｼｱﾆﾘﾞﾝ

NO2

EtO

NH2

EtO

4-Ethoxynitrobenzene 4-Ethoxyaniline 4-ﾒﾄｷｼﾆﾄﾛﾍﾞﾝｾﾞﾝ 4-ｴﾄｷｼｱﾆﾘﾞﾝ

H2

H2

H2

H2

H2

H2

20

NO2

OMe

NH2

OMe

1-Methoxy-2-nitrobenzene o-Anisidine 1-ﾒﾄｷｼ-2-ﾆﾄﾛﾍﾞﾝｾﾞﾝ ｵﾙﾄ-ｱﾆｼﾃﾞｨﾝ

OCH3

O2N

OCH3

H2N

1-Methoxy-4-nitrobenzene 1-ﾒﾄｷｼ-4-ﾆﾄﾛﾍﾞﾝｾﾞﾝ

p-Anisidine ﾊﾟﾗ-ｱﾆｼﾃﾞｨﾝ

H2

H2

21

HYDROGENATION OF AROMATIC NITRO-COMPOUNDS （芳香族ﾆﾄﾛ化合物の水素

化）

NO2

HO

NH2

HO

4-Nitrophenol 4-ﾆﾄﾛﾌｪﾉｰﾙ

4-Aminophenol 4-ｱﾐﾉﾌｪﾉｰﾙ

NO2

OH

NH2

ONa

2-Nitrophenol 2-ﾆﾄﾛﾌｪﾉｰﾙ

2-Aminophenolat Na-salt 2-ｱﾐﾉﾌｪﾉﾗｰﾄ ﾅﾄﾘｳﾑ

NO2

NO2

O2N

NH2

NH2

H2N

2,4,6-Trinitrotoluene 2,4,6-ﾄﾘﾆﾄﾛﾄﾙｴﾝ

2,4,6-Triaminotoluene 2,4,6-ﾄﾘｱﾐﾉﾄﾙｴﾝ 用途：ﾎﾟﾘｳﾚﾀﾝ樹脂原料

NO2

H2N

NH2

H2N

4-Nitroaniline 4-ﾆﾄﾛｱﾆﾘﾝ

p-Phenylenediamine ﾊﾟﾗ-ﾌｪﾆﾚﾝｼﾞｱﾐﾝ

NO2

NH2

NH2

NH2

2-Nitroaniline 2-ﾆﾄﾛｱﾆﾘﾝ

o-Phenylendiamine ｵﾙﾄ-ﾌｪﾆﾚﾝｼﾞｱﾐﾝ

O2N

H2N

1-Isopropyl-4-Nitrobenzene 1-ｲｿﾌﾟﾛﾋﾟﾙ-4-ﾆﾄﾛﾍﾞﾝｾﾞﾝ

4-Isopropylaniline 4-ｲｿﾌﾟﾛﾋﾟﾙｱﾆﾘﾝ

H2

H2

H2

H2

H2

H2

22

NO2

NH2

Nitrobenzene ﾆﾄﾛﾍﾞﾝｾﾞﾝ

Aniline ｱﾆﾘﾝ

NO2O2N

NH2H2N

1,3-Dinitrobenzene 1,3-ｼﾞﾆﾄﾛﾍﾞﾝｾﾞﾝ

m-Phenylendiamine m-ﾌｪﾆﾚﾝｼﾞｱﾐﾝ (ｼﾞｱﾐﾉﾍﾞﾝｾﾞﾝ)

用途：染料

H2

H2

23

HYDROGENATION OF AROMATIC NITRO-COMPOUNDS （芳香族ﾆﾄﾛ化合物の水素

化）

NO2

NH2

HO

Nitrobenzene ﾆﾄﾛﾍﾞﾝｾﾞﾝ

4-Aminophenol 4-ｱﾐﾉﾌｪﾉｰﾙ 用途：医薬品中間体等

1-(2-Methoxyethyl)-4-nitorobenzene 1-(2-ﾒﾄｷｼｴﾁﾙ)-4-ﾆﾄﾛﾍﾞﾝｾﾞﾝ

4-(2- Methoxyethyl)aniline 4-(2-ﾒﾄｷｼｴﾁﾙ)ｱﾆﾘﾝ

NO2O2N

NH2H2N

1,3,5-Triisopropyl-2,4-dinitrobenzene 1,3,5-ﾄﾘｲｿﾌﾟﾛﾋﾟﾙ-2,4-ｼﾞﾆﾄﾛﾍﾞﾝｾﾞﾝ

2,4,6-Triiisopropylbenzene-1,3-diamine 1,3,5-ﾄﾘｲｿﾌﾟﾛﾋﾟﾙﾍﾞﾝｾﾞﾝ-2,4-ｼﾞｱﾐﾝ

NO2NaSO3

NH2NaSO3

3-Nitrobenzene-sulfonic acid Na-salt 3-ﾆﾄﾛﾍﾞﾝｾﾞﾝ-ｽﾙﾎﾝ酸ﾅﾄﾘｳﾑ

3-Aminobenzene-sulfonic acid Na-salt 3-ｱﾐﾉﾍﾞﾝｾﾞﾝ-ｽﾙﾎﾝ酸ﾅﾄﾘｳﾑ 用途：農薬中間体

HO3S NO2

HO3S NH2

3-Nitrobenzene-sulfonic acid 3-ﾆﾄﾛﾍﾞﾝｾﾞﾝ-ｽﾙﾎﾝ酸

3-Aminobenzene-sulfonic acid 3-ｱﾐﾉﾍﾞﾝｾﾞﾝ-ｽﾙﾎﾝ酸

NO2O2N

SO3H

NH2H2N

SO3H

Dinitromesitylene-4-sulphonic acid ｼﾞﾆﾄﾛﾒｽﾁﾚﾝ-4-ｽﾙﾎﾝ酸

（2,6-ｼﾞﾆﾄﾛ-1,3,5-ﾄﾘﾒﾁﾙ-4-ｽﾙﾎﾝ酸）

Diaminomesitylene-4-sulphonic acid ｼﾞｱﾐﾉﾒｽﾁﾚﾝ-4-ｽﾙﾎﾝ酸

（2,6-ｼﾞｱﾐﾉ-1,3,5-ﾄﾘﾒﾁﾙ-4-ｽﾙﾎﾝ酸 用途：染料中間体）

NO2NO2

NH2NH2

H2

H2

H2

H2

H2

H2

H2

24

1,8-Dinitronaphtalene 1,8-ｼﾞﾆﾄﾛﾅﾌﾀﾚﾝ

1,8-Diaminonaphtalene 1,8-ｼﾞｱﾐﾉﾅﾌﾀﾚﾝ 用途：試薬

NO2

NH

NH2

NH

N-(4-Nitrophenyl)-N-phenylamine N-(4-ﾆﾄﾛﾌｪﾆﾙ-N-ﾌｪﾆﾙｱﾐﾝ

N-Phenylbenzene-1,4-diamine N-ﾌｪﾆﾙﾍﾞﾝｾﾞﾝ-1,4-ｼﾞｱﾐﾝ 用途：染料等

H2

25

HYDROGENATION OF AROMATIC NITRO-COMPOUNDS （芳香族ﾆﾄﾛ化合物の水素

化）

NH NO2

OOCH3

NH NH2

OOCH3

o-Nitro-p-acetanisidine ｵﾙﾄ-ﾆﾄﾛ-ﾊﾟﾗ-ｱｾﾀｱﾆｼﾃﾞｨﾝ

（ｵﾙﾄ-ﾆﾄﾛ-ﾊﾟﾗ-ﾒﾄｷｼｱｾﾄｱﾐﾝ）

o-Amino-p-acetanisidine ｵﾙﾄ-ｱﾐﾉ-ﾊﾟﾗ-ｱｾﾀｱﾆｼﾃﾞｨﾝ

（ｵﾙﾄ-ｱﾐﾉ-ﾊﾟﾗ-ﾒﾄｷｼｱｾﾄｱﾐﾝ 用途：染料中間物）

NO2

COOH

NH2

COOH

3-Nitrobenzoic acid 3-ﾆﾄﾛ安息香酸

3-Aminobenzoic acid 3-ｱﾐﾉ安息香酸

COOH

O2N

COOH

H2N

4-Nitrobenzoic acid 4-ﾆﾄﾛ安息香酸

4-Aminobenzoic acid 4-ｱﾐﾉ安息香酸

O2N

OMe

O

H2N

OMe

O

4-Nitrobenzoic acid methylester 4-ﾆﾄﾛ安息香酸ﾒﾁﾙｴｽﾃﾙ

（4-ﾆﾄﾛﾍﾞﾝｾﾞﾝ ｶﾙﾎﾞﾝ酸ﾒﾁﾙ）

4-Aminobenzoic acid methylester 4-ｱﾐﾉ安息香酸ﾒﾁﾙｴｽﾃﾙ

（4-ｱﾐﾉﾆﾄﾛﾍﾞﾝｾﾞﾝ ｶﾙﾎﾞﾝ酸ﾒﾁﾙ 用途：染料等）

O2N

OEt

O

H2N

OEt

O

4-Nitrobenzoic acid ethylester 4-ﾆﾄﾛ安息香酸ｴﾁﾙｴｽﾃﾙ

4-Aminobenzoic acid ethylester 4-ｱﾐﾉ安息香酸ｴﾁﾙｴｽﾃﾙ 用途：染料等

NO2

NH2

H2

H2

H2

H2

H2

H2

26

1,2-Dimethyl-3-nitrobenzene 1,2-ｼﾞﾒﾁﾙ-3-ﾆﾄﾛﾍﾞﾝｾﾞﾝ

2,3-Dimethylaniline 1,2-ｼﾞﾒﾁﾙ-3-ｱﾆﾘﾝ 用途：染料等

NO2

NH2

2,6-Dimethyl-3-nitrobenzene 2,6-ｼﾞﾒﾁﾙ-3-ﾆﾄﾛﾍﾞﾝｾﾞﾝ

2,6-Dimethylaniline 2,6-ｼﾞﾒﾁﾙｱﾆﾘﾝ

（2,6-ｷｼﾘｼﾞﾝ 用途：染料等）

NO2

NH2

1,2-Dimethyl-4-nitrobenzene 1,2-ｼﾞﾒﾁﾙ-4-ﾆﾄﾛﾍﾞﾝｾﾞﾝ

3,4-Dimethylaniline 3,4-ｼﾞﾒﾁﾙｱﾆﾘﾝ

（3,4-ｷｼﾘｼﾞﾝ 用途：ﾋﾞﾀﾐﾝ B2 原料）

H2

H2

27

HYDROGENATION OF AROMATIC NITRO-COMPOUNDS （芳香族ﾆﾄﾛ化合物の水素

化）

NO2

H25C12

NH2

H25C12

1-Dodecyl-4-nitrobenzene 1-ﾄﾞﾃﾞｼﾙ-4-ﾆﾄﾛﾍﾞﾝｾﾞﾝ

4-Dodecylaniline 4-ﾄﾞﾃﾞｼﾙｱﾆﾘﾝ

（4-ﾄﾞﾃﾞｼﾙﾍﾞﾝｼﾞﾙｱﾐﾝ）

O2N NO2

COOH

H2N NH2

COOH

3,5-Dinitrobenzoic acid 3,5-ｼﾞﾆﾄﾛ安息香酸

3,5-Diaminobenzoic acid 3,5-ｼﾞｱﾐﾉ安息香酸 用途：医薬等

NO2

COOHHOOC

NH2

COOHHOOC

5-Nitroisophtalic acid 5-ﾆﾄﾛｲｿﾌﾀﾙ酸

5-Aminoisophtalic acid 5-ｱﾐﾉｲｿﾌﾀﾙ酸

（5-ｱﾐﾉ-1,3-ﾍﾞﾝｾﾞﾝｼﾞｶﾙﾎﾞﾝ酸）

NO2

NO2

NH2

NH2

Dinitrobenzylene ｼﾞﾆﾄﾛﾍﾞﾝｼﾞﾚﾝ

Diaminobenzylene ｼﾞｱﾐﾉﾍﾞﾝｼﾞﾚﾝ （ｴﾁﾚﾝｼﾞｱﾐﾝ）

N-(2-Methyl-4-nitrophenyl)-pyrrolidine N-(2-ﾒﾁﾙ-4-ﾆﾄﾛﾌｪﾆﾙ)-ﾋﾟﾛﾘﾃﾞｨﾝ

3-Methyl-4-pyrrolidine-1-aniline 3-ﾒﾁﾙ-4-ﾋﾟﾛﾘﾃﾞｨﾝ-1-ｱﾆﾘﾝ

NO2

NH2

O

NH2

NH2

O

4-Amino-3-nitrobenzophenone 4-ｱﾐﾉ-3-ﾆﾄﾛﾍﾞﾝｿﾞﾌｪﾉﾝ

3,4-Diamino-benzophenone 3,4-ｼﾞｱﾐﾉ-ﾍﾞﾝｿﾞﾌｪﾉﾝ

H2

H2

H2

H2

H2

H2

28

（4-ｱﾐﾉ-3-ﾆﾄﾛｼﾞﾌｪﾆﾙｹﾄﾝ）

（3,4-ｼﾞｱﾐﾉｼﾞﾌｪﾆﾙｹﾄﾝ）

O

O

NO2

O

O

NH2

1-Nitroanthraquinone 1-ﾆﾄﾛｱﾝﾄﾗｷﾉﾝ

1-Aminoanthraquinone 1-ｱﾐﾉｱﾝﾄﾗｷﾉﾝ

2,4-Diamino-6-hydroxy-5-nitrosopyrimidine 2,4-ｼﾞｱﾐﾉ-6-ﾋﾄﾞﾛｷｼ-5-ﾆﾄﾛｿﾋﾟﾘﾐﾃﾞｨﾝ

2,4,6-Triamino-6-hydroxypyrimidine 2,4,6-ﾄﾘﾞｱﾐﾉ-6-ﾋﾄﾞﾛｷｼ ﾋﾟﾘﾐﾃﾞｨﾝ

H2

H2

29

HYDROGENATION OF AROMATIC NITRO-COMPOUNDS （芳香族ﾆﾄﾛ化合物の水素

化）

NO2

O

NH2

O

3-Nitroacetophenone 3-ﾆﾄﾛｱｾﾄﾌｪﾉﾝ

（3-ﾆﾄﾛﾌｪﾆﾙｴﾀﾉﾝ）

3-Aminoacetophenone 3-ｱﾐﾉｱｾﾄﾌｪﾉﾝ（3-ｱﾐﾉﾌｪﾆﾙｴﾀﾉﾝ）

用途：ﾋﾞﾀﾐﾝ B1

N N ONa

N NH2

Na-nitrosodiphenylamine Na-ﾆﾄﾛｿｼﾞﾌｪﾆﾙｱﾐﾝ

4-Aminodiphenylamine 4-ｱﾐﾉｼﾞﾌｪﾆﾙｱﾐﾝ 用途：染料中間体

3-Nitrobennzenesulphonicanilide 3-ﾆﾄﾛﾍﾞﾝｾﾞﾝｽﾙﾌｫﾝｱﾆﾘﾄﾞ

3-Aminobennzenesulphonicanilide 3-ｱﾐﾉﾍﾞﾝｾﾞﾝｽﾙﾌｫﾝｱﾆﾘﾄﾞ

9-Ethyl-3-nitro-9H-carbazole 9-ｴﾁﾙ-3-ﾆﾄﾛ-9H-ｶﾙﾊﾞｿﾞｰﾙ

9-Ethyl-3-amino-9H-carbazole 3-ｴﾁﾙ-3-ｱﾐﾉ-9H-ｶﾙﾊﾞｿﾞｰﾙ

2-Nitro-N-acetyliminodibennzyl 2-ﾆﾄﾛ-N-ｱｾﾁﾙｲﾐﾉｼﾞﾍﾞﾝｼﾞﾙ

N-(2-methoxyphenyl)-3-(3-nitrophenyl)-3- Oxopropanamide

N-(2-ﾒﾄｷｼﾌｪﾆﾙ)-3-(3-ﾆﾄﾛﾌｪﾆﾙ)-3- ｵｷｿﾌﾟﾛﾊﾟﾝｱﾐﾄﾞ

5-Acetyl-3-amino-10,11-dihydro-5H-dibenzo[b,f]azepine

5-ｱｾﾁﾙ-3-ｱﾐﾉ-10,11-ｼﾞﾋﾄﾞﾛ-5H- ｼﾞﾍﾞﾝｿﾞ[b,f]ｱｾﾞﾋﾟﾝ

（2-ｱﾐﾉ-N-ｱｾﾁﾙｲﾐﾉｼﾞﾍﾞﾝｼﾞﾙ）

3-(3-Aminophenyl)-N-(2-methoxyphenyl)-3- oxopropanamide

3-(3-ｱﾐﾉﾌｪﾆﾙ)-N-(2-ﾒﾄｷｼﾌｪﾆﾙ)-3- ｵｷｿﾌﾟﾛﾊﾟﾝｱﾐﾄﾞ

NO2

NHNH

Nitrobenzene 1,2-Diphenylhydrazine

H2

H2

H2

H2

H2

H2

H2

30

ﾆﾄﾛﾍﾞﾝｾﾞﾝ 1,2-ｼﾞﾌｪﾆﾙﾋﾄﾞﾗｼﾞﾝ （N,N’-ﾋﾞｽｱﾆﾘﾝ）

SO3HHO3S

NO2SO3H

SO3HHO3S

NH2SO3H

Nitro-T-acid ﾆﾄﾛ-T 酸

（8-ﾆﾄﾛﾅﾌﾀﾚﾝ-1,3,6-ﾄﾘｽﾙﾎﾝ酸）

Amino-T-acid ｱﾐﾉ-T-酸

（8-ｱﾐﾉﾅﾌﾀﾚﾝ-1,3,6-ﾄﾘｽﾙﾎﾝ酸） 用途：染料

4,4’-Dinitrostilbene-2,2’-disuｌphonic acid sisodium salt

4,4’-ｼﾞﾆﾄﾛｽﾁﾙﾍﾞﾝ-2,2’-ｼﾞｽﾙﾎﾝ酸 ｼﾞﾅﾄﾘｳ塩

4,4’-Diaminostilbene-2,2’-disuｌphonic acid sisodium salt

4,4’-ｼﾞｱﾐﾉｽﾁﾙﾍﾞﾝ-2,2’-ｼﾞｽﾙﾎﾝ酸 ｼﾞﾅﾄﾘｳ塩

Tris-(4-nitrophyl)-thiophoshatel ﾄﾘｽ-(4-ﾆﾄﾛﾌｪﾆﾙ)ﾁｵﾘﾝ酸塩

Tris-(4-aminophyl)-thiophoshatel ﾄﾘｽ-(4-ｱﾐﾉﾌｪﾆﾙ)ﾁｵﾘﾝ酸塩

N,N’-Bis(2,3-dihydroxypropyl)-5-ntoro-isophthalamide

N,N’-ﾋﾞｽ(2,3-ｼﾞﾋﾄﾞﾛｷｼﾌﾟﾛﾋﾟﾙ)-5’- ﾆﾄﾛｲｿﾌﾀﾙｱﾐﾄﾞ

N,N’-Bis(2,3-dihydroxypropyl)-5-amino-isophthalamide

N,N’-ﾋﾞｽ(2,3-ｼﾞﾋﾄﾞﾛｷｼﾌﾟﾛﾋﾟﾙ)-5’- ｱﾐﾉｲｿﾌﾀﾙｱﾐﾄﾞ

O

NO2O2N

O

NH2H2N

4,4’-Dinitrodiphenylether 4,4’-ｼﾞﾆﾄﾛｼﾞﾌｪﾆﾙｴｰﾃﾙ

4,4’-Diaminodiphenylether 4,4’-ｼﾞｱﾐﾉｼﾞﾌｪﾆﾙｴｰﾃﾙ

用途：ﾎﾟﾘｱﾐﾄﾞ、ﾎﾟﾘｱﾐﾄﾞの原料等

1-Methoxy-2-Nitrobenzene 1-ﾒﾄｷｼ-2-ﾆﾄﾛﾍﾞﾝｾﾞﾝ

o-Anisidine ｵﾙﾄ-ｱﾆｼﾃﾞｨﾝ

NO2

O

NH2

O

H2

H2

H2

H2

H2

H2

31

(3S)-Tetrahydro-3-furyl-N-[(1S,2R)-1-benzyl-2-hydroxy-3-(N-isobutyl-4-

nitrobenzenesurufonamido)propyl]carbamate

(3S)-ﾃﾄﾗﾋﾄﾞﾛ-3-ﾌﾘﾙ-N-[(1S,2R)-1-ﾍﾞﾝｼﾞﾙ-2-ﾋﾄﾞﾛｷｼ-3-(N-ｲｿﾌﾞﾁﾙ-4-ﾆﾄﾛﾍﾞﾝｾﾞﾝｽﾙﾎﾝｱﾐﾄﾞ）-

ﾌﾟﾛﾋﾟﾙ]ｶﾙﾊﾞﾒｰﾄ

(3S)-Tetrahydro-3-furyl-N-[(1S,2R)-3-4-

amin-o-N-isobutyl-benzenesurufonamido)-1-benzyl-2-hydroxypropyl]carbamate

(3S)-ﾃﾄﾗﾋﾄﾞﾛ-3-ﾌﾘﾙ-N-[(1S,2R)-3-(4-ｱﾐﾉ-N-ｲｿﾌﾞﾁﾙ-ﾍﾞﾝｾﾞﾝｽﾙﾎﾝｱﾐﾄﾞ）-1-ﾍﾞﾝｼﾞﾙ-2-ﾋﾄﾞﾛｷｼ

ﾌﾟﾛﾋﾟﾙ]ｶﾙﾊﾞﾒｰﾄ

3,4-Methylendioxynitrosenzene-5 Nitro-1,3-benzodioxole

3,4-ﾒﾁﾚﾝｼﾞｵｷｼﾆﾄﾛﾍﾞﾝｾﾞﾝ-5 （5-ﾆﾄﾛ-1,3-ﾍﾞﾝｿﾞｼﾞｵｸｿｰﾙ）

3,4-Methylendioxyaniline 1,3-benzodioxole-5-amine

3,4-ﾒﾁﾚﾝｼﾞｵｷｼｱﾆﾘﾝ （1,3-ﾍﾞﾝｿﾞｼﾞｵｷｿｰﾙ-5-ｱﾐﾝ）

2-Nitro-2-Phenylpropane-1,3-diol 2-ﾆﾄﾛ-2-ﾌｪﾆﾙﾌﾟﾛﾊﾟﾝ-1,3-ｼﾞｵｰﾙ

2-Phenylpropane-1,3-diol 2-ﾌｪﾆﾙﾌﾟﾛﾊﾟﾝ-1,3-ｼﾞｵｰﾙ

H2

H2

H2

32

HYDROGENATION OF DOUBLE AND TRIPLE BONDS （二重結合、三重結合の塩素化）

Methylstyrene Cumene ﾒﾁﾙｽﾁﾚﾝ ｸﾒﾝ

O

O

O

R

O

O

O

R

R= H, Tetrahydrophtalic anhydride R= Me, 3-Methyl-4-cyclohexene-1,2-

dicarboxylic anhydride

R= H, Hexahydrophtalic anhydride R= Me, 3-Methyl-4-cyclohexane-1,2-

dicaboxylic anhydride 3-ｱﾙｷﾙｼｸﾛﾍｷｾﾝ-1,2-ｼﾞｶﾙﾎﾞﾝ酸無水物 3-ｱﾙｷﾙｼｸﾛﾍｸｻﾝ-1,2-ｼﾞｶﾙﾎﾞﾝ酸無水物

COOH

CH3

COOH

CH3

Abietic acid Tetrahydroabietic acid ｱﾋﾞｴﾁﾝ酸 ﾃﾄﾗﾋﾄﾞﾛｱﾋﾞｴﾁﾝ酸

O

OH

Methylcinnamaldehyde 2-Methyl-3-phenylpropanol ﾒﾁﾙｼﾅﾑｱﾙﾃﾞﾋﾄﾞ 2-ﾒﾁﾙ-3 ﾌｪﾆﾙﾌﾟﾛﾊﾟﾉｰﾙ

O

OH

2-Ethylhept-2-enal 2-Ethylheptanol 2-ｴﾁﾙ-2-ﾍﾌﾟﾃﾅｰﾙ 2-ｴﾁﾙﾍﾌﾟﾀﾉｰﾙ

p-Isopropyl- methylcinnamaldehyde p-Isopropyl-methyldihydrocinnamaldehyde

O O

33

p-ｲｿﾌﾟﾛﾋﾟﾙ- ﾒﾁﾙｼﾞﾋﾄﾞﾛ p-ｲｿﾌﾟﾛﾋﾟﾙ- ﾒﾁﾙｼﾞﾋﾄﾞﾛｼﾝﾅﾑｱﾙﾃﾞﾋﾄﾞ

34

HYDROGENATION OF DOUBLE AND TRIPLE BONDS （二重結合、三重結合の塩素化）

RR

RR

Decene Oligomers Decane Oligomers ﾃﾞｾﾝｵﾘｺﾞﾏｰ ﾃﾞｶﾝｵﾘｺﾞﾏｰ

4-Methyl-6-phenyl-dihydropyrance

3-Methyl-5-phenyl-pentane-1-ol Rosyrane Mefrosol

4-ﾒﾁﾙ-6-ﾌｪﾆﾙ-ｼﾞﾋﾄﾞﾛﾋﾟﾗﾝ 3-ﾒﾁﾙ-5-ﾌｪﾆﾙ-1-ｵﾙ (ﾛｼﾗﾝ) (ﾒﾌﾛｿｰﾙ)

-Pinene Pinane -ﾋﾟﾈﾝ -ﾋﾟﾅﾝ

R2

HH

R1

MW ~ 500

R2

HH

R1

Poly- -olefin Hydrocarbon ﾎﾟﾘ- -ｵﾚﾌｨﾝ ﾊｲﾄﾞﾛｶｰﾎﾞﾝ

O

OH

Cinnamaldehyde 3-Phenylpropanol ｼﾅﾑｱﾙﾃﾞﾋﾄﾞ 3-ﾌｪﾆﾙﾌﾟﾛﾊﾟﾉｰﾙ

6,10,14-Trimethyl-4,5-pentadecdiene-2-one

Hexahydrofamesylacetone

6,10,14-ﾄﾘﾒﾁﾙ-4,5-ﾍﾟﾝﾀﾃﾞｸｼﾞｴﾝ-2-ｵﾝ ﾍｷｻﾋﾄﾞﾛﾌｧﾙﾈｼﾙ

2,5-Dimethylhex-3-ene-2.5-diol 2,5-Dimethylhexane-2.5-diol 2,5-ｼﾞﾒﾁﾙ-3-ﾍｷｾﾝ-2.5-ｼﾞｵｰﾙ 2,5-ｼﾞﾒﾁﾙﾍｷｻﾝ-2.5-ｼﾞｵｰﾙ

(2,5-ｼﾞﾒﾁﾙ-2.5-ﾍｷｻﾝｼﾞｵｰﾙ)

CH2OHHOH2C

OHOH

But-2-yne-1,4-diol But-2-ene-1,4-diol 2-ﾌﾞﾁﾝ-1,4-ｼﾞｵｰﾙ 2-ﾌﾞﾃﾝ-1,4-ｼﾞｵｰﾙ

35

3,3-Dimethylbut-1-yne 3,3-Dimethylbut-1-ene 3,3-ｼﾞﾒﾁﾙ-1-ﾌﾞﾁﾝ 3,3-ｼﾞﾒﾁﾙ-1-ﾌﾃﾝ

HO

HO

3,7-Dimethyloct-6-en-1-yn-3-ol 3,7-Dimethyloct-6-en-3-ol Dehydrolinalool Dihydrolinalool

3,7-ｼﾞﾒﾁﾙｵﾀﾀ-6-ｴﾝ-1-ｲﾝ-3-ｵﾙ 3,7-ｼﾞﾒﾁﾙ-6-ｵｸﾃﾝ-3-ｵﾙ

OH

OH

2,6-Dimethyl-2,6-octadien-8-ol 2,6-Dimethyl-2-octen-8-ol Geraniol Citronellol

2,6-ｼﾞﾒﾁﾙ-2,6-ｵｸﾀｼﾞｴﾝ-8-ｵﾙ 2,6-ｼﾞﾒﾁﾙ-2-ｵｸﾃﾝ-8-ｵﾙ

O

O

Pseudoionone Hexahydropseudoionone ﾌﾟｿｲﾄﾞｲｵﾉﾝ ﾍｷｻﾋﾄﾞﾛﾌﾟｿﾄﾞｲｵﾉﾝ

(2,6-ｼﾞﾒﾁﾙｳﾝﾃﾞｶ-2,6,8-ﾄﾘｴﾝ-10-ｵﾝ) (2,6-ｼﾞﾒﾁﾙ-10-ｳﾝﾃﾞｶﾉﾝ)

NCOOH

COMe

NCOOH

COMe

N-Acetylindole-2-carboxylic acid N-Acetylindoline-2-carboxylic acid N-ｱｾﾁﾙｲﾝﾄﾞｰﾙ-2-ｶﾙﾎﾞﾝ酸 N-ｱｾﾁﾙｲﾝﾄﾞﾘﾝ-2-ｶﾙﾎﾞﾝ酸

5-Acetylindole-2-allyloxy-4-ethyhlamino-

acetophenone

2,4-Diacetyl-5-hydroxy-6-propyl-N-ethylaniline

5-ｱｾﾁﾙ-2-ｱﾘﾛｷﾝ-4-ｴﾁﾙｱﾐﾉ-ｱｾﾄﾌｪﾉﾝ 2,4-ｱｾﾁﾙ l-5-ﾋﾄﾞﾛｷｼ-6-ﾌﾟﾛﾋﾟﾙ-N-ｴﾁﾙｱﾆﾘﾝ

2-(2-Carboxyvinyl acid)thiophene Na-salt

Thienyl acid Na-salt 2-(2-ｶﾙﾎﾞｷｼﾋﾞﾆﾙ酸)ﾁｵﾌｪﾝﾅﾄﾘｳﾑ塩 ﾁｴﾆﾙ酸ﾁｵﾌｪﾝﾅﾄﾘｳﾑ塩

Dehydropregnenolone acetate

Pregnenolone acetate ﾃﾞﾋﾄﾞﾛﾌﾟﾚﾈﾉﾛﾝｱｾﾃｰﾄ ﾌﾟﾚｸﾞﾈﾉﾛﾝｱｾﾃｰﾄ

O

O

Methylcinnamaldehyde Methyldihydrocinnamaldehyde ﾒﾁﾙｼﾅﾑｱﾙﾃﾞﾋﾄﾞ ﾒﾁﾙｼﾞｱﾋﾄﾞﾛｼﾅﾑｱﾙﾃﾞﾋﾄﾞ

36

O

O

4-Phenylbut-3-en-2-one 4-Phenylbutan-2-one 4-ﾌｪﾆﾙﾌﾞﾀ-3-ｴﾝ-2-ｵﾝ 4-ﾌｪﾆﾙ-2-ﾌﾞﾀﾉﾝ

1-Benzyl-4-[5,6-dimethoxy-1-indanone-

R,S-1-benzyl-4-[(5,6)-dimethoxy-1-in-anone- 2-tras-ylidene]methylpiperidine 2-yl]methylpiperidine

1-ﾍﾞﾝｼﾞﾙ-4-[5,6-ｼﾞﾒﾄｷｼ-1-ｲﾝﾀﾞﾉﾝ- R,S-1-ﾍﾞﾝｼﾞﾙ-4-[5,6-ｼﾞﾒﾄｷｼ-1-ｲﾝﾀﾞﾉﾝ- 2-ﾄﾗﾝｽ-ｲﾙﾃﾞﾝ]ﾒﾁﾙﾋﾟﾍﾟﾘｼﾞﾝ 2-ｲﾙ]ﾒﾁﾙﾋﾟﾍﾟﾘｼﾞﾝ

R2R1 n = 100n

R2R1 n = 100n

Partial unsaturated resin Partial hydrogenated resin 部分不飽和ﾚｼﾞﾝ 部分水素化ﾚｼﾞﾝ

O

O

O

O

O

O

Maleic anhydride Succinic anhydride 無水ﾏﾚｲﾝ酸 無水こはく酸

O

O

O

O

O

O

Tetrahydrophthalic anhydride Hexahydrophthalic anhydride ﾃﾄﾗﾋﾄﾞﾛﾌﾀﾙ酸無水物 ﾍｷｻﾋﾄﾞﾛﾌﾀﾙ酸無水物

4-Methyltetrahydrophthalic anhydride

4-Methylhexahydrophthalic anhydride 4-ﾒﾁﾙﾃﾄﾗﾋﾄﾞﾛﾌﾀﾙ酸無水物 4-ﾒﾁﾙﾍｷｻﾋﾄﾞﾛﾌﾀﾙ酸無水物

Epoxycyclododecadiene

Epoxycyclododecane ｴﾎﾟｷｼｼｸﾛﾄﾞﾃﾞｶｼﾞｴﾝ ｴﾎﾟｷｼｼｸﾛﾄﾞﾃﾞｶﾝ

37

HYDROGENATION OF AROMATIC HALO-NITRO-COMPOUND （芳香族ハロゲンニトロ化合物の水素化）

NO2

Cl

NH2

Cl

1-Chloro-2-nitrobenzene 2-Chloroaniline 1-ｸﾛﾛ-2-ﾆﾄﾛﾍﾞﾝｾﾞﾝ 1-ｸﾛﾛｱﾆﾘﾝ(2-ﾆﾄﾛﾍﾞﾝｾﾞﾝｱﾐﾝ)

Cl NO2

Cl NH2

1-Chloro-3-nitrobenzene 3-Chloroaniline 1-ｸﾛﾛ-3-ﾆﾄﾛﾍﾞﾝｾﾞﾝ 3-ｸﾛﾛｱﾆﾘﾝ(3-ﾆﾄﾛﾍﾞﾝｾﾞﾝｱﾐﾝ)

Cl

NO2

Cl

NH2

1-Chloro-4-nitrobenzene 4-Chloroaniline 1-ｸﾛﾛ-4-ﾆﾄﾛﾍﾞﾝｾﾞﾝ 4-ｸﾛﾛｱﾆﾘﾝ

Cl

Cl

NO2

Cl

Cl

NH2

1,4-Dichloro-3-nitrobenzene 2,5-Dichloroaniline 1,4-ｼﾞｸﾛﾛ-3-ﾆﾄﾛﾍﾞﾝｾﾞﾝ 2,5-ｼﾞｸﾛﾛｱﾆﾘﾝ

Cl

NO2Cl

Cl

NH2Cl

1,2-Dichloro-4-nitrobenzene 3,4-Dichloroaniline 1,2-ｼﾞｸﾛﾛ-4-ﾆﾄﾛﾍﾞﾝｾﾞﾝ 3,4-ｼﾞｸﾛﾛｱﾆﾘﾝ

NO2Cl

NH2Cl

2-Chloro-4-nitrotoluene 3-Chloro-4-methylaniline 2-ｸﾛﾛ-4-ﾆﾄﾛﾄﾙｴﾝ 3-ｸﾛﾛ-4-ﾒﾁﾙｱﾆﾘﾝ

Cl NO2

Cl NH2

4-Chloro-2-nitrotoluene 4-Chloro-2-aminotoluene 4-ｸﾛﾛ-2-ﾆﾄﾛﾄﾙｴﾝ 4-ｸﾛﾛ-2-ｱﾐﾉﾄﾙｴﾝ

38

NO2

F

Cl

NH2

F

Cl

2-Chloro-1-fluoro-4-nitrobenzene 3-Chloro-4-fluoroaniline 2-ｸﾛﾛ-1-ﾌﾙｵﾛ-4-ﾆﾄﾛﾍﾞﾝｾﾞﾝ 3-ｸﾛﾛ-4-ﾌﾙｵﾛｱﾆﾘﾝ

39

HYDROGENATION OF AROMATIC HALO-NITRO-COMPOUNDS

（芳香族ハロゲンニトロ化合物の水素化）

NO2

O

Cl

NH2

O

Cl

2-Chloro-1-methoxy-4-nitrobenzene 3-Chloro-4-methoxyaniline 2-ｸﾛﾛ-1-ﾒﾄｷｼ-4-ﾆﾄﾛﾍﾞﾝｾﾞﾝ 3-ｸﾛﾛ-4-ﾒﾄｷｼｱﾆﾘﾝ

NO2

H2N

Cl

NH2

H2N

Cl

2-Chloro-4-nitroaniline 2-Chlorobenzene-1,4-diamine 2-ｸﾛﾛ-4-ﾆﾄﾛｱﾆﾘﾝ 2-ｸﾛﾛﾍﾞﾝｾﾞﾝ-1,4-ｼﾞｱﾐﾝ

NH2Cl

O2N

NH2Cl

H2N

5-Chloro-2-methyl-4-nitroaniline 2-Chloro-5-methylbenzene-1,4-diamine 5-ｸﾛﾛ-2-ﾒﾁﾙ-4-ﾆﾄﾛｱﾆﾘﾝ 2-ｸﾛﾛ-5-ﾒﾁﾙﾍﾞﾝｾﾞﾝ-1,4-ｼﾞｱﾐﾝ

NO2

F

NH2

F

1-Fluoro-4-nitrobenzene 4-Fluoroaniline 1-ﾌﾙｵﾛ-4-ﾆﾄﾛﾍﾞﾝｾﾞﾝ 4-ﾌﾙｵﾛｱﾆﾘﾝ

NO2

F3C

NH2

F3C

1-Nitro-4-(trifluoromethyl)benzene 4-(Trifluoromethyl)aniline 1-ﾆﾄﾛ-4-(ﾄﾘﾌﾙｵﾛﾒﾁﾙ)ﾍﾞﾝｾﾞﾝ 4-(ﾄﾘﾌﾙｵﾛﾒﾁﾙ)ｱﾆﾘﾝ

F3C NO2

F3C NH2

1-Nitro-3-(trifluoromethyl)benzene 3-(Trifluoromethyl)aniline 1-ﾆﾄﾛ-3-(ﾄﾘﾌﾙｵﾛﾒﾁﾙ)ﾍﾞﾝｾﾞﾝ 3-(ﾄﾘﾌﾙｵﾛﾒﾁﾙ)ｱﾆﾘﾝ

O

NO2Cl

O

NH2Cl

4-Nitro-4’-chlorodiphenylether 4-Amino-4’-chlorodiphenylether 4-ﾆﾄﾛ-4’-ｸﾛﾛｼﾞﾌｪﾆﾙｴｰﾃﾙ 4-ｱﾐﾉ-4’-ｸﾛﾛｼﾞﾌｪﾆﾙｴｰﾃﾙ

2,4,4’-Trichloro-2’-nitrodiphenylether 2,4,4’-Trichloro-2’-aminodiphenylether

2,4,4’-ﾄﾘｸﾛﾛ-2’-ﾆﾄﾛｼﾞﾌｪﾆﾙｴｰﾃﾙ 2,4,4’-ﾄﾘｸﾛﾛ-2’-ｱﾐﾉｼﾞﾌｪﾆﾙｴｰﾃﾙ

40

4-Chloro-3-nitro-benzophenonecarboxylic acid 4-Chloro-3-Amino-benzophenonecarboxylic acid 4-ｸﾛﾛ-3-ﾆﾄﾛﾍﾞﾝｿﾞﾌｪﾉﾝｶﾙﾎﾞﾝ酸 4-ｸﾛﾛ-3-ｱﾐﾉﾍﾞﾝｿﾞﾌｪﾉﾝｶﾙﾎﾞﾝ酸

N-Acetyl-2-nitro-6-chloro-diphenylamine N-Acetyl-2-amino-6-chloro-diphenylamine

N-ｱｾﾁﾙ-2-ﾆﾄﾛ-6-ｸﾛﾛ-ｼﾞﾌｪﾆﾙｱﾐﾝ N-ｱｾﾁﾙ-2-ｱﾐﾉ-6-ｸﾛﾛ-ｼﾞﾌｪﾆﾙｱﾐﾝ

Ethyl-4-[(4chloro-2-nitro-phenyl)amino]-1-piperidine-carboxylat

Ethyl-4-[(4chloro-2-amino-phenyl)amino]-1-piperidine-carboxylat

ｴﾁﾙ-4-[(4 ｸﾛﾛ-2-ﾆﾄﾛ-ﾌｪﾆﾙ)ｱﾐﾉ]-1- ﾋﾟﾍﾟﾘｼﾞﾝ-ｶﾙﾎﾞｷｼﾚｰﾄ

ｴﾁﾙ-4-[(4 ｸﾛﾛ-2-ﾆﾄﾛ-ﾌｪﾆﾙ)ｱﾐﾉ]-1- ﾋﾟﾍﾟﾘｼﾞﾝ-ｶﾙﾎﾞｷｼﾚｰﾄ

5'-Nitro-2’-chloro-2-pivaloylacetanilide 5'-Amino-2’-chloro-2-pivaloylacetanilide

5'-ﾆﾄﾛ-2’-ｸﾛﾛ-2-ﾋﾟﾊﾞﾛｲﾙｱｾﾄｱﾆﾘﾄﾞ 5'-ｱﾐﾉ-2’-ｸﾛﾛ-2-ﾋﾟﾊﾞﾛｲﾙｱｾﾄｱﾆﾘﾄﾞ

4-Chloro-2-nitro-3’-3’-carboxylic acid diphenylamine K-salt

4-Chloro-2-amino-3’-carboxylic acid diphenylamine K-salt

4-ｸﾛﾛ-2-ﾆﾄﾛ-3’-ｶﾙﾎﾞﾝ酸 ｼﾞﾌｪﾆﾙｱﾐﾝ ｶﾘｳﾑ塩

4-ｸﾛﾛ-2-ｱﾐﾉ-3’-ｶﾙﾎﾞﾝ酸 ｼﾞﾌｪﾆﾙｱﾐﾝ ｶﾘｳﾑ塩

41

HYDROGENATION OF KETONES （ケトンの水素化）

O OH

OH OH

4-Hydroxy-4-methylpentan-2-one 2-Methylpentane-2,4-diol 4-ﾋﾄﾞﾛｷｼ-4-ﾒﾁﾙﾍﾟﾝﾀﾝ-2-ｵﾝ 2-ﾒﾁﾙﾍﾟﾝﾀﾝ-2,4-ｼﾞｵｰﾙ (4-ﾋﾄﾞﾛｷｼ-4-ﾒﾁﾙ-2-ﾍﾟﾝﾀﾉﾝ (2-ﾒﾁﾙ-2,4-ﾍﾟﾝﾀﾝｼﾞｵｰﾙ)

O

OH

Acetophenone 1-Phenylethanol ｱｾﾄﾌｪﾉﾝ 1-ﾌｪﾆﾙｴﾀﾉｰﾙ

O

OH

1-(4-Isobutylphenyl)ethanone 1-(4-Isobutylphenyl)ethanol 1-(4-ｲｿﾌﾞﾁﾙﾌｪﾆﾙ)ｴﾀﾉﾝ 1-(4-ｲｿﾌﾞﾁﾙﾌｪﾆﾙ)ｴﾀﾉｰﾙ

Hydroxyketoisophorone ﾋﾄﾞﾛｷｼｹﾄｲｿﾎﾛﾝ

Diacethylresorcinol ｼﾞｱｾﾁﾙﾘｿﾙｼﾉｰﾙ

3- Hydroxymethyl-4-hydroxy-tert.-

Butylamine-acetophenone 3-ﾋﾄﾞﾛｷｼﾒﾁﾙ-4-ﾋﾄﾞﾛｷｼ-ﾀｰﾄ-

ﾌﾞﾁﾙｱﾐﾝ-ｱｾﾄﾌｪﾉﾝ

3,4-Isodiol 3,4-ｲｿｼﾞｵｰﾙ

Diethylresorcinol ｼﾞｴﾁﾙﾘｿﾙｼﾉｰﾙ

1-(3-Hydroxymethyl-4-hydroxyphenyl)-

2-tert.-butyl-ethanol 1-(3-ﾋﾄﾞﾛｷｼﾒﾁﾙ-4-ﾋﾄﾞﾛｷｼﾌｪﾆﾙ)-

2-ﾀｰﾄ-ﾌﾞﾁﾙ-ｴﾀﾉｰﾙ

O

O

O

O

O

Pthalic acid anhydride Pthalide 無水ﾌﾀﾙ酸 ﾌﾀﾘﾄﾞ

O

O

O

O

O

Maleic acid anhydride -Butyrolacton 無水ﾏﾚｲﾝ酸

-ﾌﾞﾁﾛﾗｸﾄﾝ

42

Benzyl-tert.-butylaminoacetophenone ﾍﾞﾝｼﾞﾙ-ﾀｰﾄ-ﾌﾞﾁﾙｱﾐﾉｱｾﾄﾌｪﾉﾝ

3,7 DKLCA ｼﾞｹﾄﾝｺﾗﾝ酸

3,5-dihydroxy-N-isobutylbenzamide

Terbutalin 3,5-ｼﾞﾋﾄﾞﾛｷｼ-N-ｲｿﾌﾞﾁﾙﾍﾞﾝｽﾞｱﾐﾄﾞ

ﾃﾙﾌﾞﾀﾘﾝ

3,7 DHLCA ｼﾞﾋﾄﾞﾛｷｼｺﾗﾝ酸（胆汁酸）

3-Methyl-5-(2,2,3-Trimethyl-3-cyclopenten-1-yl)- 3-penten-2-one

5-(2,2,3-Trimethyl-3-cyclopentenyl)- 3-methylpentan-2-ol

3-ﾒﾁﾙ-5-(2,2,3-ﾄﾘﾒﾁﾙ-3-ｼｸﾛﾍﾟﾝﾀﾝ-1-ｲﾙ)- 3-ﾍﾟﾝﾃﾝ-2-ｵﾝ

5-(2,2,3-ﾄﾘﾒﾁﾙ-3-ｼｸﾛﾍﾟﾝﾁﾆﾙ)- 3-ﾒﾁﾙﾍﾟﾝﾀﾝ-2-ｵﾙ

Trimethylquinone ﾄﾘﾒﾁﾙｷﾉﾝ

Trimethylhydroquinone ﾄﾘﾒﾁﾙﾋﾄﾞﾛｷﾉﾝ

O

O

CH3

OH

OH

CH3

2-Ethylanthraquinone 2-ｴﾁﾙｱﾝﾄﾗｷﾉﾝ

Tetrahydro-2-ethylanthraquinone ﾃﾄﾗﾋﾄﾞﾛ-2-ｴﾁﾙｱﾝﾄﾗｷﾉﾝ

O OH

43

HYDROGENATION OF NITRILES （ニトリルの水素化）

CN

NH

Propionitrile Dipropylamine ﾌﾟﾛﾋﾟｵﾆﾄﾘﾙ (ｼｱﾝ化ｴﾁﾙ) ｼﾞﾌﾟﾛﾋﾟﾙｱﾐﾝ (N-ﾌﾟﾛﾋﾟﾙﾌﾟﾛﾊﾟﾝｱﾐﾝ)

NCN

N NH2

3-(Dimethylamino)propionitril N,N-dimethylpropane-1,3-diamine 3-(ｼﾞﾒﾁﾙｱﾐﾉ)ﾌﾟﾛﾋﾟｵﾆﾄﾘﾙ N,N-ｼﾞﾒﾁﾙﾌﾟﾛﾊﾟﾝ-1,3-ｼﾞｱﾐﾝ

(ｼｱﾝ化ｴﾁﾙ)

NCCN

NC NH2

Succinonitrile Aminobutyronitrile ｽｸｼﾉﾆﾄﾘﾙ (ｴﾁﾚﾝｼﾞｱﾆﾄﾞ) ｱﾐﾉﾌﾞﾁﾛﾆﾄﾘﾙ ｱﾐﾉﾌﾞﾀﾝﾆﾄﾘﾙ

NCCN

H2NNH2

Suberonitrile Ooctane-1,8-diamine ｽﾍﾞﾛﾆﾄﾘﾙ ｵｸﾀﾝ-1,8-ｼﾞｱﾐﾝ

(1,6-ﾍｷｻﾝｼﾞｶﾙﾎﾞﾆﾄﾘﾙ) (1,8-ｼﾞｱﾐﾉｵｸﾀﾝ) H2N CN

H2N

NH2

-Aminocapronitrile Hexane-1,6-diamine -ｱﾐﾉｶﾌﾟﾛﾆﾄﾙ ﾍｷｻﾝ-1,6-ｼﾞｱﾐﾝ

(6-ｱﾐﾉ-ﾍｷｻﾝﾆﾄﾘﾙ) (1,6-ｼﾞｱﾐﾉﾍｷｻﾝ) CN

NC

H2NNH2

Sebaconitrile Decane-1,10-diamine ｾﾊﾞｺﾆﾄﾘﾙ ﾃﾞｶﾝ-1,10-ｼﾞｱﾐﾝ

(1,10-ｼﾞｱﾐﾉﾃﾞｶﾝ)

NCN

CN

NH2N NH2

Bis-[2-cyanoethyl]methylamine N-(3-Aminopropyl)-N-methylpropane-1,3-diamine

ﾋﾞｽ-[2-ｼｱﾉｴﾁﾙ]ﾒﾁﾙｱﾐﾝ N-(3-ｱﾐﾉﾌﾟﾛﾋﾟﾙ)-N-ﾒﾁﾙﾌﾟﾛﾊﾟﾝ-1,3-ｼﾞｱﾐﾝ

N

CN

NNH2

(Diethylamino)acetonitrile N,N-Diethylethane-1,2-diamine (ｼﾞｴﾁﾙｱﾐﾉ)ｱｾﾄﾆﾄﾘﾙ N,N-ｼﾞｴﾁﾙｴﾀﾝ-1,2-ｼﾞｱﾐﾝ

Bis-[2-cyanoethyl]butanediol ﾋﾞｽ-[2-ｼｱﾉｴﾁﾙ]ﾌﾞﾀﾝｼﾞｵｰﾙ

α,ω-Dicyanoethylpolyethylendiamine α,ω-ｼﾞｼｱﾉｴﾁﾙﾎﾟﾘｴﾁﾚﾝｼﾞｱﾐﾝ

3-[4-(3-Aminopropoxy)butoxy]propylamine 3-[4-(3-ｱﾐﾉﾌﾟﾛﾎﾟｷｼ)ﾌﾞﾄｷｼ]ﾌﾟﾛﾋﾟﾙｱﾐﾄﾞ

α,ω-Diaminopropylpolyethylendiamine α,ω-ｼﾞｱﾐﾉﾌﾟﾛﾋﾟﾙﾎﾟﾘｴﾁﾚﾝｼﾞｱﾐﾝ

44

(2-Cyanocyclohexyl)acetic acid (2-ｼｱﾉｼｸﾛﾍｷｼﾙ)酢酸

3-(3-Methylphenyl)pentanenitrile 3-(3-ﾒﾁﾙﾌｪﾆﾙ)ﾍﾟﾝﾀﾝﾆﾄﾘﾙ

(3,4-Dimethoxyphenyl)acetonitrile (3,4-ｼﾞﾒﾄｷｼﾌｪﾆﾙ)ｱｾﾄﾆﾄﾘﾙ

(Dicyanoethylpropylamine)-ethylenediamine (ｼﾞｼｱノｴﾁﾙ-ﾌﾟﾛﾋﾟﾙｱﾐﾝ)-ｴﾁﾚﾝｼﾞｱﾐﾝ

Isophoronnitrileazine ｲｿﾎﾛﾝﾆﾄﾘﾙｱｼﾞﾝ

[2-(Aminomethyl)cyclohexyl]acetic acid 2-(ｱﾐﾉﾒﾁﾙ)ｼｸﾛﾍｷｼﾙ 酢酸

3-(3-Methylphenyl)pentan-1-amine 3-(3-ﾒﾁﾙﾌｪﾆﾙ)ﾍﾟﾝﾀﾝ-1-ｱﾐﾝ

2-(3,4-Dimethoxyphenyl)ethanamine 2-(3,4-ｼﾞﾒﾄｷｼﾌｪﾆﾙ)ｴﾁﾙｱﾐﾝ

Bis-(Diaminopropyl)-ethylenediamine ﾋﾞｽ-(ｼﾞｱﾐﾉﾌﾟﾛﾋﾟﾙ)-ｴﾁﾚﾝｼﾞｱﾐﾝ

Isophorondiamine ｲｿﾎﾛﾝｼﾞｱﾐﾝ

R CN

R

NH2

Fatty acid nitrile Primary fatty acid amine 脂肪酸ﾆﾄﾘﾙ 脂肪酸第 1級ｱﾐﾝ

R CN

R

NH2

Fatty acid nitrile Primary fatty acid amine 脂肪酸ﾆﾄﾘﾙ 脂肪酸第 1級ｱﾐﾝ

RNH2 CN

+

R

NHCN

Fatty acid nitrile or amine Secondary fatty acid amines 脂肪酸ﾆﾄﾘﾙ若しくはｱﾐﾝ 脂肪酸第 2級ｱﾐﾝ

RNH

CN

R

NH NH2

Secondary fatty acid amines 脂肪酸第 2級ｱﾐﾝ 脂肪酸第 2級ｱﾐﾝ

R CN

R

NHR

Secondary fatty acid amines 脂肪酸ﾆﾄﾘﾙ 脂肪酸第 2級ｱﾐﾝ

RNH

R

CH2O

RN

R

Secondary fatty amines Tertiary fatty acid amines 脂肪酸第 2級ｱﾐﾝ 脂肪酸第 3級ｱﾐﾝ

H2N C N + CH3 COOH

H2N C

NH2

H

-OOC CH3

+

Cyanamide ｼｱﾅﾐﾄﾞ

Fromamidine acetate ﾎﾙﾑｱﾐｼﾞﾝｱｾﾀｰﾄ (ﾎﾙﾑｱﾐｼﾞﾝ酢酸塩)

45

HYDROGENATION OF RESINS（樹脂の水素化）

n

n

Polystyrene Polycyclohexane ﾎﾟﾘｽﾁﾚﾝ ﾎﾟﾘｼｸﾛﾍｷｻﾝ

n

n

未確認 未確認

n

n

C9-Resin C9-Resin C9-樹脂 C9-樹脂

RR

n

R = Styrene

R

R

R = Styrene

Kraton D ｸﾚｲﾄﾝ D R=ｽﾁﾚﾝ R=ｽﾁﾚﾝ

RR

nR = Styrene

R

R

nR = Styrene

SV 50 R=ｽﾁﾚﾝ R=ｽﾁﾚﾝ

R

R

n

R

R

n

C9 Polymer resin Hydrogenated C9 Polymer resin C9 ポリマー樹脂 水素化された C9 ポリマー樹脂

H2

H2

H2

H2

H2

H2

46

CHR2

CHR2

Polymer mixture ポリマー混合物

Hydrogenated polymer mixture 水素化されたポリマー混合物

H2

47

RING HYDROGENATION（環状化合物の水素化）

a) Cyclic Compounds（環式化合物）

OH

O

Phenol Cyclohexanone ﾌｪﾉｰﾙ ｼｸﾛﾍｷｻﾉﾝ

OH

OH

4-tert-Butylphenol 4-tert-Butylcyclohexanol 4-ﾀｰｼｬﾘｰ-ﾌﾞﾁﾙﾌｪﾉｰﾙ 4-ﾀｰｼｬﾘｰ-ﾌﾞﾁﾙｼｸﾛﾍｷｻﾉｰﾙ

OH

O

4-tert-Butylphenol 4-tert-Butylcyclohexanone 4-ﾀｰｼｬﾘｰ-ﾌﾞﾁﾙﾌｪﾉｰﾙ 4-ﾀｰｼｬﾘｰ-ﾌﾞﾁﾙｼｸﾛﾍｷｻﾉﾝ

n-Dodecylbenzene n-Dodecylcyclohexane n-ﾄﾞﾃﾞｼﾙﾍﾞﾝｾﾞﾝ n-ﾄﾞﾃﾞｼﾙｼｸﾛﾍｷｻﾝ

OH

OH

Naphtol 5,6,7,8-Tetrahydro- Naphtol ﾅﾌﾄｰﾙ 5,6,7,8-ﾃﾄﾗﾋﾄﾞﾛ- ﾅﾌﾄｰﾙ

NH2

NH2

Aniline Cyclohexylamine ｱﾆﾘﾝ ｼｸﾛﾍｷｼﾙｱﾐﾝ

OH

R

MeO

OH

R

+ CH3OH

Alkylguaiacol m-Alkylcyclohexanol ｱﾙｷﾙｸﾞｱｲｱｺｰﾙ m-ｱﾙｷﾙｼｸﾛﾍｷｻﾉｰﾙ

H2

H2

H2

H2

H2

H2

H2

48

NH

HOO

NH

HOO

Paracetamol ﾊﾟﾗｾﾀﾓｰﾙ(ｱｾﾄｱﾐﾉﾌｪﾝ)

N-(4-Hydroxycyclohexyl)acetamide N-(4-ﾋﾄﾞﾛｷｼｼｸﾛﾍｷｼﾙ)ｱｾﾄｱﾐﾄﾞ

H2

49

RING HYDROGENATION （環状化合物水素化）

COOMe

MeOOC

COOMe

MeOOC

Terephtalic acid methyl ester ﾃﾚﾌﾀﾙ 酸ﾒﾁﾙｴｽﾃﾙ

1,4-Cyclohexanedicarboxylic acid dimethylester 1,4-ｼｸﾛﾍｷｻﾝｼﾞｶﾙﾎﾞﾝ酸ｼﾞﾒﾁﾙｴｽﾃﾙ

NH2H2N

NH2H2N

4,4’-Diaminodiphenylmethane 4,4’-Diaminodicylohexylmethane 4,4’-ｼﾞｱﾐﾉｼﾞﾌｪﾆﾙﾒﾀﾝ 4,4’-ｼﾞｱﾐﾉｼﾞｼｸﾛﾍｷｼﾙﾒﾀﾝ

OHHO

OHHO

2,2-Bis-(4-hydroxyphenyl)-propane 2,2-Bis-(4-hydroxycyclohexyl)-propane 2,2-ﾋﾞｽ-(4-ﾋﾄﾞﾛｷｼﾌｪﾆﾙ)-ﾌﾟﾛﾊﾟﾝ 2,2-ﾋﾞｽ-(4-ﾋﾄﾞﾛｷｼ ｼｸﾛﾍｷｼﾙ)-ﾌﾟﾛﾊﾟﾝ

O

O

OH

OH

3-Ethylanthraquinone 3-Ethyl-tetrahydro anthrahydroquinone 3-ｴﾁﾙｱﾝﾄﾗｷﾉﾝ 3-ｴﾁﾙ-ﾃﾄﾗﾋﾄﾞﾛ ｱﾝﾄﾗﾋﾄﾞﾛｷﾉﾝ

O

O

OH

OH

3-Amylanthraquinone 3-Amyl-tetrahydro anthrahydroquinone 3-ｱﾐﾙｱﾝﾄﾗｷﾉﾝ 3-ｱﾐﾙ-ﾃﾄﾗﾋﾄﾞﾛ ｱﾝﾄﾗﾋﾄﾞﾛｷﾉﾝ

OMe

O

OMe

O

Cinnamic acid methylester Cyclohexylpropionic acid methylester ｼﾅﾐｯｸ酸ﾒﾁﾙｴｽﾃﾙ ｼｸﾛﾍｷｼﾙﾌﾟﾛﾋﾟｵﾝ酸 ﾒﾁﾙｴｽﾃﾙ

Phenylmethyldimethoxysilane ﾌｪﾆﾙﾒﾁﾙｼﾞﾒﾄｷｼｼﾗﾝ

Cyclohexylmethyldimethoxysilane ｼｸﾛﾍｷｼﾙﾒﾁﾙｼﾞﾒﾄｷｼｼﾗﾝ

H2

H2

H2

H2

H2

H2

H2

50

(S)-N-t-By-1,2,3,4-Tetrahydroisoquinoline-3-carboxamide

(S)-N-ﾀｰｼｬﾘｰ-ﾌﾞﾁﾙ-1,2,3,4-ﾃﾄﾗﾋﾄﾞﾛｲｿｷﾉﾘﾝ-3-

(S)-N-t-Butyl-decahydroisoquinoline-3-carboxamide

(S)-N-ﾀｰｼｬﾘｰ-ﾌﾞﾁﾙ-ﾃﾞｶﾋﾄﾞﾛｲｿｷﾉﾘﾝ-3- ｶﾙﾎﾞｷｼｱﾐﾄﾞ ｶﾙﾎﾞｷｼｱﾐﾄﾞ

H2

51

RING HYDROGENATION （環状化合物水素化）

b) Heterocyclic Compounds （ヘテロ環(複素環)の水素化）

N

N

Pyridine Piperidine ﾋﾟﾘｼﾞﾝ ﾋﾟﾍﾟﾘｼﾞﾝ

N

N

2-Picoline 2-Methylpiperidine 2-ﾋﾟｺﾘﾝ 2-ﾒﾁﾙﾋﾟﾍﾟﾘｼﾞﾝ

NOH

NOH

2-Ethanolpyridine 2-Ethanolpiperidine 2-ｴﾀﾉｰﾙﾋﾟﾘｼﾞﾝ 2-ｴﾀﾉｰﾙﾋﾟﾍﾟﾘｼﾞﾝ

N

COOH

N

COOH

Isonicotinic acid Isopecotin acid ｲｿﾆｺﾁﾝ酸 ｲｿﾍﾟｺﾁﾝ酸

Diphenyl-4-pyridyl-carbinol ｼﾞﾌｪﾆﾙ-4-ﾋﾟﾘｼﾞﾙ-ｶﾙﾋﾞﾉｰﾙ

Diphenyl-4-piperidyl-carbinol ｼﾞﾌｪﾆﾙ-4-ﾋﾟﾍﾟﾘｼﾞﾙ-ｶﾙﾋﾞﾉｰﾙ

Encainide 3 ｴﾝｶｲﾆﾄﾞ 3

Encainide 4 ｴﾝｶｲﾆﾄﾞ 4

H2

H2

H2

H2

H2

H2