JPS6030302B2 - ニトリルからエステルの製造法 - Google Patents

ニトリルからエステルの製造法

Info

Publication number: JPS6030302B2
Authority: JP; Japan
Prior art keywords: nitrile; hydroxyl compound; carried out; carboxylic acid; acid ester
Prior art date: 1977-04-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP53047151A

Other languages

English (en)

Japanese (ja)

Other versions

JPS53135947A (en

Inventor

アンソニ−・ジエイ・フアネリ

アブラハム・ピ−・ゲルベイン

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Lummus Technology LLC

Original Assignee

Lummus Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-04-29

Filing date

1978-04-20

Publication date

1985-07-16

1978-04-20 Application filed by Lummus Co filed Critical Lummus Co

1978-11-28 Publication of JPS53135947A publication Critical patent/JPS53135947A/ja

1985-07-16 Publication of JPS6030302B2 publication Critical patent/JPS6030302B2/ja

Status Expired legal-status Critical Current

Links

150000002825 nitriles Chemical class 0.000 title claims description 19
238000004519 manufacturing process Methods 0.000 title claims description 4
150000002148 esters Chemical class 0.000 title description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
-1 hydroxyl compound Chemical class 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 16
239000003054 catalyst Substances 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
238000000034 method Methods 0.000 claims description 13
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 claims description 9
239000012808 vapor phase Substances 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 7
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
DTNSDCJFTHMDAK-UHFFFAOYSA-N 2-cyanobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C#N DTNSDCJFTHMDAK-UHFFFAOYSA-N 0.000 claims description 4
FUKWTMJZHKZKFA-UHFFFAOYSA-N 4-cyanobenzamide Chemical compound NC(=O)C1=CC=C(C#N)C=C1 FUKWTMJZHKZKFA-UHFFFAOYSA-N 0.000 claims description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
YJMNOKOLADGBKA-UHFFFAOYSA-N naphthalene-1-carbonitrile Chemical compound C1=CC=C2C(C#N)=CC=CC2=C1 YJMNOKOLADGBKA-UHFFFAOYSA-N 0.000 claims description 4
STQPCKPKAIRSEL-UHFFFAOYSA-N 2-cyanobenzamide Chemical compound NC(=O)C1=CC=CC=C1C#N STQPCKPKAIRSEL-UHFFFAOYSA-N 0.000 claims description 3
ADCUEPOHPCPMCE-UHFFFAOYSA-N 4-cyanobenzoic acid Chemical compound OC(=O)C1=CC=C(C#N)C=C1 ADCUEPOHPCPMCE-UHFFFAOYSA-N 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 claims description 3
XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 claims description 3
229920006391 phthalonitrile polymer Polymers 0.000 claims description 3
150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
PAQVSWFCADWSLB-UHFFFAOYSA-N 3-cyanobenzamide Chemical compound NC(=O)C1=CC=CC(C#N)=C1 PAQVSWFCADWSLB-UHFFFAOYSA-N 0.000 claims description 2
GYLKKXHEIIFTJH-UHFFFAOYSA-N 3-cyanobenzoic acid Chemical compound OC(=O)C1=CC=CC(C#N)=C1 GYLKKXHEIIFTJH-UHFFFAOYSA-N 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims description 2
235000021317 phosphate Nutrition 0.000 claims description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
239000000741 silica gel Substances 0.000 claims description 2
229910002027 silica gel Inorganic materials 0.000 claims description 2
229910000314 transition metal oxide Inorganic materials 0.000 claims description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 2
239000004327 boric acid Substances 0.000 claims 2
125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
150000002739 metals Chemical class 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 8
239000007858 starting material Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 5
125000004093 cyano group Chemical group *C#N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000000047 product Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
239000007806 chemical reaction intermediate Substances 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
RSGBXCFAYHOKQZ-UHFFFAOYSA-N 4-(cyanomethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CC#N)C=C1 RSGBXCFAYHOKQZ-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001408 amides Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000001733 carboxylic acid esters Chemical class 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000004811 liquid chromatography Methods 0.000 description 2
239000012071 phase Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
JMHSCWJIDIKGNZ-UHFFFAOYSA-N 4-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=C(C(O)=O)C=C1 JMHSCWJIDIKGNZ-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical class NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
229910052733 gallium Inorganic materials 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
229910001463 metal phosphate Inorganic materials 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
150000003504 terephthalic acids Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/18—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group
- C07C67/22—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group from nitriles
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pyridine Compounds (AREA)

JP53047151A 1977-04-29 1978-04-20 ニトリルからエステルの製造法 Expired JPS6030302B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US79214677A	1977-04-29	1977-04-29
US792146		1985-10-28

Publications (2)

Publication Number	Publication Date
JPS53135947A JPS53135947A (en)	1978-11-28
JPS6030302B2 true JPS6030302B2 (ja)	1985-07-16

Family

ID=25155940

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP53047151A Expired JPS6030302B2 (ja)	1977-04-29	1978-04-20	ニトリルからエステルの製造法

Country Status (6)

Country	Link
JP (1)	JPS6030302B2 (it)
DE (1)	DE2817508A1 (it)
FR (1)	FR2388787A1 (it)
GB (1)	GB1575260A (it)
IT (1)	IT7848982A0 (it)
NL (1)	NL7804412A (it)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2898356B1 (fr) *	2006-03-07	2008-12-05	Rhodia Recherches & Tech	Diesters d'acides carboxylique ramifies
FR2903983B1 (fr) *	2006-07-18	2010-07-30	Rhodia Recherches & Tech	Procede de fabrication de diesters.
CN103483199B (zh) *	2013-09-02	2015-06-17	浙江海昇化学有限公司	一种四氟对苯二甲酸酯的制备方法

1978
- 1978-04-19 IT IT7848982A patent/IT7848982A0/it unknown
- 1978-04-20 JP JP53047151A patent/JPS6030302B2/ja not_active Expired
- 1978-04-20 GB GB15753/78A patent/GB1575260A/en not_active Expired
- 1978-04-21 DE DE19782817508 patent/DE2817508A1/de not_active Ceased
- 1978-04-25 NL NL7804412A patent/NL7804412A/xx not_active Application Discontinuation
- 1978-04-27 FR FR7812472A patent/FR2388787A1/fr active Granted

Also Published As

Publication number	Publication date
DE2817508A1 (de)	1978-11-02
FR2388787B3 (it)	1980-11-28
NL7804412A (nl)	1978-10-31
GB1575260A (en)	1980-09-17
JPS53135947A (en)	1978-11-28
FR2388787A1 (fr)	1978-11-24
IT7848982A0 (it)	1978-04-19

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US3313840A (en)	1967-04-11	Process for the production of the dinitriles of fumaric acid and maleic acid
US3466320A (en)	1969-09-09	Method for the preparation of esters of unsaturated acids from the corresponding nitriles
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US3029245A (en)	1962-04-10	Preparation of aromatic nitriles
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US4634789A (en)	1987-01-06	Conversion of acetonitrile to glycolonitrile and/or glycolamide
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