JP4046353B2 - 不飽和カルボン酸からのメルカプトカルボン酸の製造方法 - Google Patents

不飽和カルボン酸からのメルカプトカルボン酸の製造方法 Download PDF

Info

Publication number: JP4046353B2
Authority: JP; Japan
Prior art keywords: acid; medium; reaction; process according; formula
Prior art date: 1995-12-11
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 - Fee Related

Application number

JP52179697A

Other languages

English (en)

Japanese (ja)

Other versions

JP2000501723A5 (2

JP2000501723A (ja

Inventor

ラバ，イブ

Original Assignee

エルフアトケムエス．アー．

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.)

1995-12-11

Filing date

1996-12-10

Publication date

2008-02-13

1996-12-10 Application filed by エルフアトケムエス．アー． filed Critical エルフアトケムエス．アー．

2000-02-15 Publication of JP2000501723A publication Critical patent/JP2000501723A/ja

2004-10-21 Publication of JP2000501723A5 publication Critical patent/JP2000501723A5/ja

2008-02-13 Application granted granted Critical

2008-02-13 Publication of JP4046353B2 publication Critical patent/JP4046353B2/ja

2016-12-10 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 title claims description 10
238000004519 manufacturing process Methods 0.000 title claims description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 title claims description 6
238000006243 chemical reaction Methods 0.000 claims description 26
238000000034 method Methods 0.000 claims description 26
239000002609 medium Substances 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 18
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 10
-1 alkali metal cation Chemical class 0.000 claims description 10
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
230000001476 alcoholic effect Effects 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 claims description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 6
229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
239000012429 reaction media Substances 0.000 claims description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
239000011976 maleic acid Substances 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
238000011065 in-situ storage Methods 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
239000012736 aqueous medium Substances 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
239000001530 fumaric acid Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000002430 hydrocarbons Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000000203 mixture Substances 0.000 claims description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
238000011112 process operation Methods 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 6
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 5
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
WRYBVNBPNIZGQQ-UHFFFAOYSA-N 2-sulfanylpropanenitrile Chemical compound CC(S)C#N WRYBVNBPNIZGQQ-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000002994 raw material Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
150000004763 sulfides Chemical class 0.000 description 3
NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 3
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229960000380 propiolactone Drugs 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
SASYRHXVHLPMQD-UHFFFAOYSA-N 2-(1,2-dicarboxyethylsulfanyl)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)SC(C(O)=O)CC(O)=O SASYRHXVHLPMQD-UHFFFAOYSA-N 0.000 description 1
NDVLTZFQVDXFAN-UHFFFAOYSA-N 3-(2-cyanoethylsulfanyl)propanenitrile Chemical compound N#CCCSCCC#N NDVLTZFQVDXFAN-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000003513 alkali Chemical group 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
150000002596 lactones Chemical group 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
LDTLDBDUBGAEDT-UHFFFAOYSA-N methyl 3-sulfanylpropanoate Chemical compound COC(=O)CCS LDTLDBDUBGAEDT-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000005304 optical glass Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000003973 paint Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000006077 pvc stabilizer Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/04—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by addition of hydrogen sulfide or its salts to unsaturated compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP52179697A 1995-12-11 1996-12-10 不飽和カルボン酸からのメルカプトカルボン酸の製造方法 Expired - Fee Related JP4046353B2 (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR95/14638		1995-12-11
FR9514638A FR2742146B1 (fr)	1995-12-11	1995-12-11	Procede de fabrication d'acides mercaptocarboxyliques a partir d'acides carboxyliques insatures
PCT/FR1996/001970 WO1997021672A1 (fr)	1995-12-11	1996-12-10	Procede de fabrication d'acides mercaptocarboxyliques a partir d'acides carboxyliques insatures

Publications (3)

Publication Number	Publication Date
JP2000501723A JP2000501723A (ja)	2000-02-15
JP2000501723A5 JP2000501723A5 (2)	2004-10-21
JP4046353B2 true JP4046353B2 (ja)	2008-02-13

Family

ID=9485358

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP52179697A Expired - Fee Related JP4046353B2 (ja)	1995-12-11	1996-12-10	不飽和カルボン酸からのメルカプトカルボン酸の製造方法

Country Status (7)

Country	Link
US (1)	US6689907B1 (2)
EP (1)	EP0876339B1 (2)
JP (1)	JP4046353B2 (2)
CA (1)	CA2239100C (2)
DE (1)	DE69610335T2 (2)
FR (1)	FR2742146B1 (2)
WO (1)	WO1997021672A1 (2)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP5424672B2 (ja) *	2008-03-12	2014-02-26	昭和電工株式会社	β−メルカプトカルボン酸類の製造方法
WO2010095745A1 (ja) *	2009-02-23	2010-08-26	昭和電工株式会社	３－メルカプトカルボン酸の製造方法
CN102030692A (zh) *	2010-12-10	2011-04-27	中国科学院烟台海岸带研究所	一种2-巯基丁二酸的合成方法
CN103946210B (zh) *	2011-11-21	2016-05-11	三井化学株式会社	β-巯基羧酸的制造方法
EP2784063B1 (en) *	2011-11-21	2018-09-19	Mitsui Chemicals, Inc.	Method for producing beta-mercaptocarboxylic acid
US9126909B2 (en) *	2012-12-06	2015-09-08	The United States Of America, As Represented By The Secretary Of Agriculture	Heavy metal remediation via sulfur-modified bio-oils
CN108569988A (zh) *	2018-07-26	2018-09-25	三门峡恒生科技研发有限公司	一种分离提纯硫代苹果酸的方法
CN112409227B (zh) *	2020-11-30	2023-01-20	益丰新材料股份有限公司	一种高效合成3-巯基丙酸的方法
FR3121931A1 (fr) *	2021-04-19	2022-10-21	Arkema France	Procedes de preparation de mercapto-acides

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB639679A (en)	1945-10-05	1950-07-05	Goodrich Co B F	Improvements in or relating to beta-thio-carboxylic acid compounds and method of preparing the same
GB670702A (en) *	1947-11-21	1952-04-23	Ralph Liggett Evans	Improvements in or relating to the preparation of mercapto-carboxylic acids and salts and amides thereof
FR1485206A (fr)	1964-01-24	1967-06-16	Appleton Coated Paper Company	Plaques pour impression planographique à support en papier
FR1485266A (fr) *	1965-07-03	1967-06-16	Stamicarbon	Préparation d'acide bêta-mercaptopropionique
NL6508594A (2)	1965-07-03	1967-01-04
US3840586A (en) *	1972-09-11	1974-10-08	Sankyo Organic Chem Co Ltd	Process for producing beta-mercapto-propionic ester
GB1358019A (en) *	1972-09-11	1974-06-26	Sankyo Organic Chemicals Co	Process for producing beta-mercapto propionic acid and esters thereof
DE2354098B2 (de)	1973-10-29	1976-05-13	Akzo Gmbh, 5600 Wuppertal	Verfahren zur herstellung von mercaptocarbonsaeuren
DE3223973A1 (de) *	1982-06-26	1983-12-29	Degussa Ag, 6000 Frankfurt	Verfahren zur herstellung von ss-mercaptopropionsaeurederivaten
US5008432A (en) *	1985-07-11	1991-04-16	Phillips Petroleum Company	Production of mercapto compounds
US5157147A (en) *	1990-11-05	1992-10-20	Witco Corporation	Method for preparing mercaptopropionic acid esters
JPH07228568A (ja) *	1993-12-22	1995-08-29	Nippon Shokubai Co Ltd	硫黄化合物の製造方法
US5391820A (en) *	1994-04-13	1995-02-21	Hampshire Chemical Corp.	Preparation of 3-mercaptopropionitrile and 3-mercaptopropionic acid

1995
- 1995-12-11 FR FR9514638A patent/FR2742146B1/fr not_active Expired - Fee Related
1996
- 1996-12-10 EP EP96941731A patent/EP0876339B1/fr not_active Expired - Lifetime
- 1996-12-10 WO PCT/FR1996/001970 patent/WO1997021672A1/fr not_active Ceased
- 1996-12-10 JP JP52179697A patent/JP4046353B2/ja not_active Expired - Fee Related
- 1996-12-10 CA CA002239100A patent/CA2239100C/fr not_active Expired - Fee Related
- 1996-12-10 DE DE69610335T patent/DE69610335T2/de not_active Expired - Lifetime
2000
- 2000-11-16 US US09/713,189 patent/US6689907B1/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
FR2742146A1 (fr)	1997-06-13
WO1997021672A1 (fr)	1997-06-19
DE69610335T2 (de)	2001-03-29
JP2000501723A (ja)	2000-02-15
US6689907B1 (en)	2004-02-10
DE69610335D1 (de)	2000-10-19
CA2239100A1 (fr)	1997-06-19
CA2239100C (fr)	2006-08-01
EP0876339B1 (fr)	2000-09-13
FR2742146B1 (fr)	1998-01-02
EP0876339A1 (fr)	1998-11-11

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2007-02-15	A521	Request for written amendment filed	Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070124
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2007-09-12	A911	Transfer to examiner for re-examination before appeal (zenchi)	Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20070913
2007-10-16	TRDD	Decision of grant or rejection written
2007-10-24	A01	Written decision to grant a patent or to grant a registration (utility model)	Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20071023
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Publication	Publication Date	Title
JP4046353B2 (ja)	2008-02-13	不飽和カルボン酸からのメルカプトカルボン酸の製造方法
US4390723A (en)	1983-06-28	Process for producing hydroxyphenyl aliphatic acid derivatives
US5391820A (en)	1995-02-21	Preparation of 3-mercaptopropionitrile and 3-mercaptopropionic acid
US4460780A (en)	1984-07-17	Process for preparation of optically active thiol compounds
JPH06145138A (ja)	1994-05-24	β−メルカプトプロピオン酸の製造方法
US5399763A (en)	1995-03-21	Process for preparing optically active 2-aminopropanal
KR20010040542A (ko)	2001-05-15	혼합 고순도 (메트)아크릴산 무수물의 향상된 제조 방법
JP7402174B2 (ja)	2023-12-20	メチオニンとそのヒドロキシアナログのメチルエステルの脱メチル化
JPH0859605A (ja)	1996-03-05	メルカプトカルボン酸エステルの合成
JPH02240055A (ja)	1990-09-25	ビシナルアルカンジチオール類の合成
JPH11209341A (ja)	1999-08-03	メルカプトカルボン酸類の製造方法
KR100697249B1 (ko)	2007-03-21	티오펜올 유도체의 제조방법
KR100335852B1 (ko)	2003-02-11	페닐아세톡시아세트산유도체의제조방법
US6175024B1 (en)	2001-01-16	Synthesis of functionalized esters
SK282089B6 (sk)	2001-10-08	Spôsob výroby kyseliny tioglykolovej
RU2047601C1 (ru)	1995-11-10	Способ получения солей тиогликолевой кислоты в виде водных растворов
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