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 PDFInfo
- Publication number
- JP4046353B2 JP4046353B2 JP52179697A JP52179697A JP4046353B2 JP 4046353 B2 JP4046353 B2 JP 4046353B2 JP 52179697 A JP52179697 A JP 52179697A JP 52179697 A JP52179697 A JP 52179697A JP 4046353 B2 JP4046353 B2 JP 4046353B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- medium
- reaction
- process according
- formula
- Prior art date
- 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
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)
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)
| 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)
| 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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