CN101434567B - Preparation method of lignocaine ethanethiol - Google Patents
Preparation method of lignocaine ethanethiol Download PDFInfo
- Publication number
- CN101434567B CN101434567B CN200810080197A CN200810080197A CN101434567B CN 101434567 B CN101434567 B CN 101434567B CN 200810080197 A CN200810080197 A CN 200810080197A CN 200810080197 A CN200810080197 A CN 200810080197A CN 101434567 B CN101434567 B CN 101434567B
- Authority
- CN
- China
- Prior art keywords
- thiirane
- diethylamine
- generate
- ethanethiol
- preparation
- 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.)
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 title abstract 8
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 title abstract 4
- 229960004194 lidocaine Drugs 0.000 title abstract 4
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 claims abstract description 30
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 19
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 13
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims abstract description 13
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000006227 byproduct Substances 0.000 claims abstract description 10
- 238000007259 addition reaction Methods 0.000 claims abstract description 9
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims abstract description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 6
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 6
- YBDSNEVSFQMCTL-UHFFFAOYSA-N 2-(diethylamino)ethanethiol Chemical compound CCN(CC)CCS YBDSNEVSFQMCTL-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000009835 boiling Methods 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 238000011010 flushing procedure Methods 0.000 claims description 3
- 230000001988 toxicity Effects 0.000 claims description 3
- 231100000419 toxicity Toxicity 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- IBMWUXPLZIKUFY-UHFFFAOYSA-N C(C)N[S] Chemical compound C(C)N[S] IBMWUXPLZIKUFY-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- 238000010189 synthetic method Methods 0.000 abstract 1
- UURAUHCOJAIIRQ-QGLSALSOSA-N tiamulin Chemical compound CCN(CC)CCSCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 UURAUHCOJAIIRQ-QGLSALSOSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000009360 aquaculture Methods 0.000 description 3
- 244000144974 aquaculture Species 0.000 description 3
- MYKZLATVIJZNTH-UHFFFAOYSA-N azane;cyano thiocyanate Chemical compound N.N#CSC#N MYKZLATVIJZNTH-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 241000272496 Galliformes Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229960004885 tiamulin Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200810080197A CN101434567B (en) | 2008-12-19 | 2008-12-19 | Preparation method of lignocaine ethanethiol |
Applications Claiming Priority (1)
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---|---|---|---|
CN200810080197A CN101434567B (en) | 2008-12-19 | 2008-12-19 | Preparation method of lignocaine ethanethiol |
Publications (2)
Publication Number | Publication Date |
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CN101434567A CN101434567A (en) | 2009-05-20 |
CN101434567B true CN101434567B (en) | 2012-10-24 |
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Family Applications (1)
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---|---|---|---|
CN200810080197A Active CN101434567B (en) | 2008-12-19 | 2008-12-19 | Preparation method of lignocaine ethanethiol |
Country Status (1)
Country | Link |
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CN (1) | CN101434567B (en) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102153494B (en) * | 2011-03-04 | 2014-04-30 | 赵云现 | Synthesis technology for N,N-diethylamino group ethanethiol |
CN103819374A (en) * | 2012-11-16 | 2014-05-28 | 张丽学 | Process for synthesizing diethylaminoethyl mercaptide |
CN104447449B (en) * | 2014-12-30 | 2016-06-15 | 陕西师范大学 | The method of one pot process taimulin |
CN104672206B (en) * | 2015-02-16 | 2016-09-07 | 张丽学 | A kind of preparation technology of thiirane |
CN104774164A (en) * | 2015-02-16 | 2015-07-15 | 张丽学 | Preparation process for 2-diethylaminoethanethiol |
CN105152990B (en) * | 2015-07-30 | 2017-03-22 | 宁夏泰瑞制药股份有限公司 | Preparation method for diethylaminoethanethiol |
CN105999996A (en) * | 2016-06-20 | 2016-10-12 | 保定加合精细化工有限公司 | Method for recycling thiirane from waste gas |
CN107011221B (en) * | 2017-03-03 | 2018-12-28 | 河北科技大学 | A kind of preparation method of diethylamino ethanethiol |
CN109134425B (en) * | 2017-06-27 | 2021-04-16 | 保定加合精细化工有限公司 | Method for preparing high-purity ethylene sulfide |
CN109134322B (en) * | 2017-06-27 | 2020-08-28 | 保定加合精细化工有限公司 | Method for preparing diethylaminoethanethiol |
CN109608365B (en) * | 2018-12-10 | 2021-04-20 | 万华化学集团股份有限公司 | Preparation method of taurine |
CN111302989A (en) * | 2020-03-11 | 2020-06-19 | 新疆浙大阳光生物科技有限公司 | Production device for preparing organic intermediate |
CN113387854A (en) * | 2020-03-11 | 2021-09-14 | 新疆上昵生物科技有限公司 | Complete method for preparing diethylaminoethanethiol |
CN113387922A (en) * | 2020-03-11 | 2021-09-14 | 新疆上昵生物科技有限公司 | Preparation process for synthesizing ethylene sulfide by using sodium thiocyanate and ethylene carbonate |
CN113735819B (en) * | 2020-05-29 | 2024-01-12 | 新疆上昵生物科技有限公司 | Preparation process of ethylene sulfide |
CN113307751A (en) * | 2020-12-31 | 2021-08-27 | 保定北瑞甾体生物有限公司 | Process for producing aliphatic mercaptan |
CN113372248A (en) * | 2021-06-11 | 2021-09-10 | 保定北瑞甾体生物有限公司 | Process for preparing thiols |
CN115028559A (en) * | 2021-07-12 | 2022-09-09 | 新疆上昵生物科技有限公司 | Preparation method of diethylaminoethanethiol |
CN114315665A (en) * | 2021-12-16 | 2022-04-12 | 保定加合精细化工有限公司 | Preparation method of 2-diethylaminoethanethiol and application of impurities thereof |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4278674A (en) * | 1971-10-05 | 1981-07-14 | Sandoz Ltd. | Substituted 14-desoxy-mutilin compositions |
EP0289262A2 (en) * | 1987-04-27 | 1988-11-02 | Syntex Pharmaceuticals International Limited | Omega-quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal antiinflammatory drugs |
CN1696109A (en) * | 2005-05-16 | 2005-11-16 | 北京大学 | Derivative of substitutional taurine and preparation method |
CN101250145A (en) * | 2008-04-02 | 2008-08-27 | 苏州科技学院 | Method for preparing diethylamino ethanethiol |
-
2008
- 2008-12-19 CN CN200810080197A patent/CN101434567B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4278674A (en) * | 1971-10-05 | 1981-07-14 | Sandoz Ltd. | Substituted 14-desoxy-mutilin compositions |
EP0289262A2 (en) * | 1987-04-27 | 1988-11-02 | Syntex Pharmaceuticals International Limited | Omega-quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal antiinflammatory drugs |
CN1696109A (en) * | 2005-05-16 | 2005-11-16 | 北京大学 | Derivative of substitutional taurine and preparation method |
CN101250145A (en) * | 2008-04-02 | 2008-08-27 | 苏州科技学院 | Method for preparing diethylamino ethanethiol |
Non-Patent Citations (2)
Title |
---|
H. R. Snyder et al..The Synthesis of Amino Mercaptans from Olefin Sulfides.《J. Am. Chem. Soc.》.1947,第69卷(第11期),第2672-2674页. * |
Robert J. Wineman et al..Thiolethylation of Amines with Ethylene Sulfide.《J. Org. Chem.》.1962,第27卷(第12期),第4222-4226页. * |
Also Published As
Publication number | Publication date |
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CN101434567A (en) | 2009-05-20 |
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Owner name: LI YANG Free format text: FORMER OWNER: DUAN XINFENG Effective date: 20100916 |
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Inventor after: Li Yang Inventor before: Duan Xinfeng Inventor before: Sun Meiju |
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Free format text: CORRECT: ADDRESS; FROM: 050021 NO.602, UNIT 4, BUILDING 4, NO.12, HUIHUA ROAD, QIAODONG DISTRICT, SHIJIAZHUANG CITY, HEBEI PROVINCE TO: 068350 NO.83, FUQIAN STREET, BAITA VILLAGE, DAGE TOWN, FENGNING MANCHU AUTONOMOUS COUNTY, HEBEI PROVINCE Free format text: CORRECT: INVENTOR; FROM: DUAN XINFENG SUN MEIJU TO: LI YANG |
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Effective date of registration: 20100916 Address after: 068350, Hebei province Fengning Manchu Autonomous County big court town Baita village Front Street No. 83 Applicant after: Li Yang Address before: Qiaodong District of Shijiazhuang City, 050021 Department of Hebei province No. 12 Hua Road No. 602 building 4 unit 4 Applicant before: Duan Xinfeng |
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Application publication date: 20090520 Assignee: Baoding Jiahe Fine Chemical Co., Ltd. Assignor: Li Yang Contract record no.: 2012130000199 Denomination of invention: Preparation of lignocaine ethanethiol Granted publication date: 20121024 License type: Exclusive License Record date: 20121212 |
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Assignee: Baoding Jiahe Fine Chemical Co., Ltd. Assignor: Li Yang Contract record no.: 2012130000199 Date of cancellation: 20150909 |
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Effective date of registration: 20151103 Address after: 072154, Mancheng County, Mancheng County, Hebei City, Baoding Province Patentee after: BAODING JIUFU BIOCHEMICAL CO., LTD. Address before: 068350, Hebei province Fengning Manchu Autonomous County big court town Baita village Front Street No. 83 Patentee before: Li Yang |
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CP01 | Change in the name or title of a patent holder | ||
CP01 | Change in the name or title of a patent holder |
Address after: 072154 Pang village, Yujiazhuang Township, Mancheng County, Baoding City, Hebei Province Patentee after: Hebei Yuanda Jiufu Biotechnology Co.,Ltd. Address before: 072154 Pang village, Yujiazhuang Township, Mancheng County, Baoding City, Hebei Province Patentee before: BAODING JIUFU BIOCHEMICAL Co.,Ltd. |