CA2239100C - Procede de fabrication d'acides mercaptocarboxyliques a partir d'acides carboxyliques insatures - Google Patents

Procede de fabrication d'acides mercaptocarboxyliques a partir d'acides carboxyliques insatures Download PDF

Info

Publication number: CA2239100C
Authority: CA; Canada
Prior art keywords: acid; medium; reaction; formula; process according
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

CA002239100A

Other languages

English (en)

French (fr)

Other versions

CA2239100A1 (fr

Inventor

Yves Labat

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.)

Arkema France SA

Original Assignee

Elf Atochem SA

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

2006-08-01

1996-12-10 Application filed by Elf Atochem SA filed Critical Elf Atochem SA

1997-06-19 Publication of CA2239100A1 publication Critical patent/CA2239100A1/fr

2006-08-01 Application granted granted Critical

2006-08-01 Publication of CA2239100C publication Critical patent/CA2239100C/fr

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 class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 title claims abstract description 8
238000000034 method Methods 0.000 title claims description 31
150000001735 carboxylic acids Chemical class 0.000 title description 6
239000002253 acid Substances 0.000 claims abstract description 50
238000006243 chemical reaction Methods 0.000 claims abstract description 29
-1 alkali metal cation Chemical class 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 6
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
150000001768 cations Chemical class 0.000 claims abstract description 5
239000012429 reaction media Substances 0.000 claims abstract description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 4
238000006386 neutralization reaction Methods 0.000 claims abstract description 4
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 3
229930195733 hydrocarbon Natural products 0.000 claims abstract description 3
238000011065 in-situ storage Methods 0.000 claims abstract 2
239000002609 medium Substances 0.000 claims description 16
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 11
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
230000001476 alcoholic effect Effects 0.000 claims description 7
235000019260 propionic acid Nutrition 0.000 claims description 7
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 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
150000007524 organic acids Chemical class 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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
229910052500 inorganic mineral Chemical class 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000011707 mineral Chemical class 0.000 claims description 4
235000005985 organic acids Nutrition 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
239000012736 aqueous medium Substances 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 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
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
239000001530 fumaric acid Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
239000011976 maleic acid Substances 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
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 31
229910000037 hydrogen sulfide Inorganic materials 0.000 description 29
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
238000005755 formation reaction Methods 0.000 description 6
229910014033 C-OH Inorganic materials 0.000 description 5
229910014570 C—OH Inorganic materials 0.000 description 5
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
235000010755 mineral Nutrition 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000002994 raw material Substances 0.000 description 3
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
WRYBVNBPNIZGQQ-UHFFFAOYSA-N 2-sulfanylpropanenitrile Chemical compound CC(S)C#N WRYBVNBPNIZGQQ-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910021529 ammonia Inorganic materials 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
150000003839 salts Chemical class 0.000 description 2
150000004763 sulfides Chemical class 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 2
NDVLTZFQVDXFAN-UHFFFAOYSA-N 3-(2-cyanoethylsulfanyl)propanenitrile Chemical compound N#CCCSCCC#N NDVLTZFQVDXFAN-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
IYAVYMAGJPJCNJ-UHFFFAOYSA-N S=[SH2] Chemical compound S=[SH2] IYAVYMAGJPJCNJ-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
150000001412 amines Chemical class 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 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
239000003822 epoxy resin Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000009434 installation Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000000686 lactone group 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
239000003607 modifier Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 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
239000004848 polyfunctional curative Substances 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
229940072033 potash Drugs 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
229960000380 propiolactone Drugs 0.000 description 1
239000006077 pvc stabilizer Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000009466 transformation 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)

CA002239100A 1995-12-11 1996-12-10 Procede de fabrication d'acides mercaptocarboxyliques a partir d'acides carboxyliques insatures Expired - Fee Related CA2239100C (fr)

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 (2)

Publication Number	Publication Date
CA2239100A1 CA2239100A1 (fr)	1997-06-19
CA2239100C true CA2239100C (fr)	2006-08-01

Family

ID=9485358

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002239100A Expired - Fee Related CA2239100C (fr)	1995-12-11	1996-12-10	Procede de fabrication d'acides mercaptocarboxyliques a partir d'acides carboxyliques insatures

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
JP4046353B2 (ja)	2008-02-13
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
EP0876339B1 (fr)	2000-09-13
FR2742146B1 (fr)	1998-01-02
EP0876339A1 (fr)	1998-11-11

Legal Events

Date	Code	Title	Description
2001-11-16	EEER	Examination request
2011-12-12	MKLA	Lapsed

Publication	Publication Date	Title
CA2239100C (fr)	2006-08-01	Procede de fabrication d'acides mercaptocarboxyliques a partir d'acides carboxyliques insatures
CA1185263A (fr)	1985-04-09	Procede de production de dithioacides organiques et leur application
JPH0625223A (ja)	1994-02-01	２，５−ビス（メルカプトメチル）−１，４−ジチアンの製造法
JP3836518B2 (ja)	2006-10-25	３−メルカプトプロピオニトリルおよび３−メルカプトプロピオン酸の製造方法
CA2243667A1 (fr)	1999-02-27	Synthese d'acides carboxyalkylthiosucciniques
CH642614A5 (fr)	1984-04-30	Procede de preparation d'acides trichlorophenoxyalcanoiques et de leurs derives exempts de dibenzo-p-dioxines chlorees.
JP2001187778A (ja)	2001-07-10	β−メルカプトプロピオン酸の製造方法
JPH06145138A (ja)	1994-05-24	β−メルカプトプロピオン酸の製造方法
JPS6340424B2 (2)	1988-08-11
EP0382617B1 (fr)	1992-08-12	Synthèse d'alcanedithiols vicinaux
CA2124536C (fr)	1998-12-01	Procede de preparation d'acides alcanesulfoniques
JPH01149762A (ja)	1989-06-12	４−（アルキルスルホニル）−２−アミノフェノールの製造方法
EP1439166A1 (fr)	2004-07-21	Procédé de préparation d'esters oméga-benzyliques d'amino-diacides et d'alcanesulfonates de ces esters ainsi que ces alcanesulfonates
EP0697401A1 (fr)	1996-02-21	Synthèse d'esters d'acides mercaptocarboxyliques
EP0337838B1 (fr)	1991-12-11	Synthèse du benzylmercaptan
FR2574792A1 (fr)	1986-06-20	Procede pour la preparation de derives de pyrrolidine
WO2001009085A1 (fr)	2001-02-08	Procede de fabrication de la cyanhydrine de la methyl ethyl cetone
CA2241234A1 (fr)	1997-07-10	Procede de preparation d'acides perfluoroalcanecarboxyliques et perfluoroalcanesulfoniques
JPH11209341A (ja)	1999-08-03	メルカプトカルボン酸類の製造方法
FR2479220A1 (fr)	1981-10-02	Procede de preparation de derives chlores de la benzoxazolone
KR100697249B1 (ko)	2007-03-21	티오펜올 유도체의 제조방법
FR2634481A1 (fr)	1990-01-26	Procede de purification de l'acide d-hydroxyphenoxypropionique
CH414666A (fr)	1966-06-15	Procédé de préparation de l'acide homocystéique
BE631288A (2)
FR2481700A1 (fr)	1981-11-06	Procede de purification d'ether sulfonates