DE1237563B - Verfahren zur Herstellung von beta-Mercaptopropionsaeure - Google Patents
Verfahren zur Herstellung von beta-MercaptopropionsaeureInfo
- Publication number
- DE1237563B DE1237563B DEST25566A DEST025566A DE1237563B DE 1237563 B DE1237563 B DE 1237563B DE ST25566 A DEST25566 A DE ST25566A DE ST025566 A DEST025566 A DE ST025566A DE 1237563 B DE1237563 B DE 1237563B
- Authority
- DE
- Germany
- Prior art keywords
- mol
- acid
- hydrogen sulfide
- acrylic acid
- yield
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 title description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 11
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 11
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 4
- 235000019260 propionic acid Nutrition 0.000 claims 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 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YCLSOMLVSHPPFV-UHFFFAOYSA-N 3-(2-carboxyethyldisulfanyl)propanoic acid Chemical compound OC(=O)CCSSCCC(O)=O YCLSOMLVSHPPFV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6508594A NL6508594A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-07-03 | 1965-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1237563B true DE1237563B (de) | 1967-03-30 |
Family
ID=19793562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEST25566A Pending DE1237563B (de) | 1965-07-03 | 1966-06-22 | Verfahren zur Herstellung von beta-Mercaptopropionsaeure |
Country Status (6)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0097791A1 (de) * | 1982-06-26 | 1984-01-11 | Degussa Aktiengesellschaft | Verfahren zur Herstellung von beta-Mercaptopropionsäurederivaten |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2203810B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-10-21 | 1977-03-11 | Akzo Nv | |
| DE2354098B2 (de) * | 1973-10-29 | 1976-05-13 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur herstellung von mercaptocarbonsaeuren |
| JPS6030666B2 (ja) * | 1980-08-20 | 1985-07-17 | 鐘淵化学工業株式会社 | 光学活性メルカプトカルボン酸の製造法 |
| US5057622A (en) * | 1989-08-16 | 1991-10-15 | Witco Corporation | 3-alkylthiopropionic acids and derivatives |
| US5055606A (en) * | 1989-08-16 | 1991-10-08 | Witco Corporation | Alkylthiopropionic pentaerythritol esters and solvent refining thereof |
| FR2742146B1 (fr) | 1995-12-11 | 1998-01-02 | Atochem Elf Sa | Procede de fabrication d'acides mercaptocarboxyliques a partir d'acides carboxyliques insatures |
-
1965
- 1965-07-03 NL NL6508594A patent/NL6508594A/xx unknown
-
1966
- 1966-06-20 US US558578A patent/US3517058A/en not_active Expired - Lifetime
- 1966-06-22 GB GB27998/66A patent/GB1150720A/en not_active Expired
- 1966-06-22 DE DEST25566A patent/DE1237563B/de active Pending
- 1966-06-23 CH CH910866A patent/CH471096A/de not_active IP Right Cessation
- 1966-07-01 BE BE683577D patent/BE683577A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0097791A1 (de) * | 1982-06-26 | 1984-01-11 | Degussa Aktiengesellschaft | Verfahren zur Herstellung von beta-Mercaptopropionsäurederivaten |
| US4490307A (en) * | 1982-06-26 | 1984-12-25 | Degussa Aktiengesellschaft | Process for the production of β-mercaptopropionic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1150720A (en) | 1969-04-30 |
| BE683577A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-01-03 |
| US3517058A (en) | 1970-06-23 |
| CH471096A (de) | 1969-04-15 |
| NL6508594A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-01-04 |
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