CN101434567A - Preparation of lignocaine ethanethiol - Google Patents
Preparation of lignocaine ethanethiol Download PDFInfo
- Publication number
- CN101434567A CN101434567A CNA2008100801979A CN200810080197A CN101434567A CN 101434567 A CN101434567 A CN 101434567A CN A2008100801979 A CNA2008100801979 A CN A2008100801979A CN 200810080197 A CN200810080197 A CN 200810080197A CN 101434567 A CN101434567 A CN 101434567A
- Authority
- CN
- China
- Prior art keywords
- thiirane
- ethanethiol
- diethylamine
- preparation
- generate
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 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 16
- 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 23
- 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
- 229910003202 NH4 Inorganic materials 0.000 claims description 4
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 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
- 238000005516 engineering process Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000010189 synthetic method 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
- 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
- 229960004885 tiamulin Drugs 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
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000463 material Substances 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
- 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
- 239000002699 waste material Substances 0.000 description 1
Abstract
The invention particularly relates to a preparation method of lignocaine ethanethiol in the field of medical technology. The method includes steps as follows: ethylene carbonate reacts with anhydrous thiocyanate to generate an intermediate product of thiirane, a side product of cyanate and gas of carbon dioxide, and then diethylamine and the intermediate product of thiirane go through an addition reaction to generate lignocaine ethanethiol. In the method, a synthetic route that the thiirane and the diethylamine are adopted for carrying out the addition reaction to generate the lignocaine ethanethiol is characterized by short technological process, simple working operation, high yield, high purity, small power consumption, less pollution and low cost, thus being a synthetic method applicable to enterprise manufacturing.
Description
Technical field
The present invention is specifically related to the preparation method of a kind of diethylamino ethanethiol of medical technical field.
Background technology:
Tiamulin (Tiamulin) is a kind of two terpenes animal specific microbiotic, is mainly used in control domestic animals and fowls respiratory system disease and promoting animal growth, is one of ten big microbiotic for animals in the world.In recent years, Tiamulin was particularly used in chicken aquaculture and the pig aquaculture in a large number widely in aquaculture.And as the key intermediate of producing Tiamulin, diethylamino ethanethiol has very big demand in the pharmacy corporation of producing Tiamulin.
Summary of the invention
Technical problem to be solved by this invention provides a kind of reactive behavior height, and directional property is good, the product purity height, and the yield height, operation technological process is short, seldom causes the preparation method of the diethylamino ethanethiol of environmental pollution.
The present invention adopts following technical scheme:
The method of the invention comprises: generate intermediate thiirane and by product cyanate and atmospheric carbon dioxide by NSC 11801 and anhydrous rhodanide reaction earlier, carry out addition reaction with diethylamine and intermediate thiirane again and generate diethylamino ethanethiol, described method comprises following concrete steps:
A, be 1:1～1.5 with NSC 11801 and anhydrous rhodanide reaction mol ratio, in 80 ℃～100 ℃ reactions of temperature, be incubated 4～5 hours, generate thiirane and by product cyanate, atmospheric carbon dioxide can directly discharge:
ASCN+C
2H
4O
2CO→AOCN+C
2H
4S+CO
2
A is a metal-salt;
B, thiirane and diethylamine are carried out addition reaction, mol ratio is 1:1～1.5, between 60 ℃～75 ℃ of temperature, slowly is warmed up to 60-120 ℃ of ℃ air distillation after back flow reaction 3-4 hour and goes out excessive diethylamine, and residuum is a diethylamino ethanethiol:
C
2H
4S+R
2NH→R
2NCH
2CH
2SH
R：CH3CH2—。
Thiocyanate-of the present invention comprises potassium sulfocyanate, Sodium Thiocyanate 99 and ammonium thiocyanate:
ASCN+C
2H
4O
2CO→AOCN+C
2H
4S+CO
2
A:Na or K or NH4.
The present invention makes content after the flushing of by product cyanate water can reach the cyanate that the industrial goods done more than 98% sell.
The present invention is because the thiirane boiling point is lower, and toxicity is bigger, reveals for preventing thiirane, and whole process flow is carried out in whole closed system.
Positively effect of the present invention is as follows:
It is short that the synthetic route that the present invention adopts thiirane and diethylamine addition reaction to generate diethylamino ethanethiol has technical process, and the characteristics that operation is simple, yield is high, purity is high, energy consumption is little, pollution is little, cost is low are suitable for the synthetic method that enterprise produces.
Embodiment
Synthetic route synthetic route of the present invention is short, and technical process is short, less investment, and operation is few, and cost is low, and the diethylamino ethanethiol purity height that obtains can use with import reagent rank diethylamino ethanethiol equal parts, is suitable for enterprise's suitability for industrialized production.
Reaction mechanism and equation that the present invention adopts are as follows:
(1) prepares thiirane and cyanate by NSC 11801 and anhydrous rhodanide reaction.
ASCN+C
2H
4O
2CO→AOCN+C
2H
4S+CO
2
A:Na or K or NH4
(2) by thiirane and diethylamine prepared in reaction diethylamino ethanethiol.
C
2H
4S+R
2NH→R
2NCH
2CH
2SH
R：CH3CH2—
In order to realize the foregoing invention purpose, the present invention takes following technology synthetic schemes:
A kind of preparation method of diethylamino ethanethiol is characterized in that described method comprises: generate intermediate thiirane and by product cyanate and carbonic acid gas by NSC 11801 and anhydrous rhodanide reaction earlier.Carry out addition reaction with diethylamine and intermediate thiirane again and generate diethylamino ethanethiol.
Particularly, described method comprises following concrete steps:
A, with NSC 11801 and anhydrous rhodanide reaction, in 80 ℃～100 ℃ reactions of temperature, be incubated 4～5 hours, generate thiirane and by product cyanate, atmospheric carbon dioxide can directly discharge.
ASCN+C
2H
4O
2CO→AOCN+C
2H
4S+CO
2
A:Na or K or NH4
B, thiirane and diethylamine are carried out addition reaction, between 60 ℃～75 ℃ of temperature, slowly be warmed up to 120 ℃ of air distillations after back flow reaction 3-4 hour and go out excessive diethylamine, residuum is a diethylamino ethanethiol;
C
2H
4S+R
2NH→R
2NCH
2CH
2SH
R：CH3CH2—
C, by product cyanate water flushing back content can reach more than 98%, can do industrial goods and sell.
D, because the thiirane boiling point is lower, and toxicity is bigger, and technical process is preferably made whole enclosed system, prevent that thiirane from revealing.
Described thiocyanate-comprises potassium sulfocyanate, Sodium Thiocyanate 99 and ammonium thiocyanate.
Compared with prior art, beneficial effect of the present invention is that the preparation method of this diethylamino ethanethiol is simple directly, technical process is short, and cost is low, the yield height, three-waste free pollution, simultaneously, this preparation method's reactive behavior height, directional property is good, easy and simple to handle, yield is up to more than 98%, application promise in clinical practice in pharmaceutical industries.
Embodiment 1
Get 645g potassium sulfocyanate and 450g NSC 11801 and join in the 1500mL four-hole round-bottomed flask, be warmed up to 80 ℃, be incubated 5 hours, collect the thiirane 300g that distills out around here and in susceptor, seal the cooling storage.
300g thiirane and 365g diethylamine that the last step was obtained join in the 1000mL four-hole boiling flask simultaneously, in temperature is back flow reaction 4 hours between 75 ℃, between 60 ℃, carry out the air distillation operation then, steam excessive diethylamine, remaining material is the about 600g of diethylamino ethanethiol finished product in the flask.
Embodiment 2
Get 538g Sodium Thiocyanate 99 and 450g NSC 11801 and join in the 1500mL four-hole round-bottomed flask, be warmed up to 100 ℃, be incubated 4 hours, collect the thiirane 300g that distills out around here and in susceptor, seal the cooling storage.
300g thiirane and 365g diethylamine that the last step was obtained join in the 1000mL four-hole boiling flask simultaneously, in temperature is back flow reaction 4 hours between 60 ℃, between 120 ℃, carry out the air distillation operation then, steam excessive diethylamine, remaining material is the about 600g of diethylamino ethanethiol finished product in the flask.
Embodiment 3
Get 505g ammonium thiocyanate and 450g NSC 11801 and join in the 1500mL four-hole round-bottomed flask, be warmed up to 90 ℃, be incubated 4.5 hours, collect the thiirane 300g that distills out around here and in susceptor, seal the cooling storage.
300g thiirane and 365g diethylamine that the last step was obtained join in the 1000mL four-hole boiling flask simultaneously, in temperature is back flow reaction 4 hours between 70 ℃, between 90 ℃, carry out the air distillation operation then, steam excessive diethylamine, remaining material is the about 600g of diethylamino ethanethiol finished product in the flask.
Claims (4)
1, a kind of preparation method of diethylamino ethanethiol, it is characterized in that described method comprises: generate intermediate thiirane and by product cyanate and atmospheric carbon dioxide by NSC 11801 and anhydrous rhodanide reaction earlier, carry out addition reaction with diethylamine and intermediate thiirane again and generate diethylamino ethanethiol, described method comprises following concrete steps:
A, be 1:1～1.5 with NSC 11801 and anhydrous rhodanide reaction mol ratio, in 80 ℃～100 ℃ reactions of temperature, be incubated 4～5 hours, generate thiirane and by product cyanate, atmospheric carbon dioxide can directly discharge:
ASCN+C
2H
4O
2CO→AOCN+C
2H
4S+CO
2
A is a metal-salt;
B, thiirane and diethylamine are carried out addition reaction, mol ratio is 1:1～1.5, between 60 ℃～75 ℃ of temperature, slowly is warmed up to 60-120 ℃ of ℃ air distillation after back flow reaction 3-4 hour and goes out excessive diethylamine, and residuum is a diethylamino ethanethiol:
C
2H
4S+R
2NH→R
2NCH
2CH
2SH
R：CH3CH2—。
2, the preparation method of a kind of diethylamino ethanethiol according to claim 1 is characterized in that described thiocyanate-comprises potassium sulfocyanate, Sodium Thiocyanate 99 and ammonium thiocyanate:
ASCN+C
2H
4O
2CO→AOCN+C
2H
4S+CO
2
A:Na or K or NH4.
3, the preparation method of a kind of diethylamino ethanethiol according to claim 1 is characterized in that making content after the flushing of by product cyanate water can reach the cyanate that the industrial goods done more than 98% sell.
4, the preparation method of a kind of diethylamino ethanethiol according to claim 1 it is characterized in that because the thiirane boiling point is lower, and toxicity is bigger, reveals for preventing thiirane, and whole process flow is carried out in whole closed system.
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)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810080197A CN101434567B (en) | 2008-12-19 | 2008-12-19 | Preparation method of lignocaine ethanethiol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101434567A true CN101434567A (en) | 2009-05-20 |
| CN101434567B CN101434567B (en) | 2012-10-24 |
Family
ID=40709222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200810080197A Active CN101434567B (en) | 2008-12-19 | 2008-12-19 | Preparation method of lignocaine ethanethiol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101434567B (en) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102153494A (en) * | 2011-03-04 | 2011-08-17 | 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 |
| CN104672206A (en) * | 2015-02-16 | 2015-06-03 | 张丽学 | Preparation process of ethylene sulfide |
| CN104774164A (en) * | 2015-02-16 | 2015-07-15 | 张丽学 | Preparation process for 2-diethylaminoethanethiol |
| CN105152990A (en) * | 2015-07-30 | 2015-12-16 | 宁夏泰瑞制药股份有限公司 | Preparation method for diethylaminoethanethiol |
| CN104447449B (en) * | 2014-12-30 | 2016-06-15 | 陕西师范大学 | The method of one pot process taimulin |
| 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 |
| CN107011221A (en) * | 2017-03-03 | 2017-08-04 | 河北科技大学 | A kind of preparation method of diethylamino ethanethiol |
| CN109134322A (en) * | 2017-06-27 | 2019-01-04 | 保定加合精细化工有限公司 | A method of preparing diethylamino ethanethiol |
| CN109134425A (en) * | 2017-06-27 | 2019-01-04 | 保定加合精细化工有限公司 | A method of preparing high-purity thiirane |
| CN109608365A (en) * | 2018-12-10 | 2019-04-12 | 万华化学集团股份有限公司 | A kind of 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 |
| 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 |
| 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 |
| 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 |
| CN113735819A (en) * | 2020-05-29 | 2021-12-03 | 新疆上昵生物科技有限公司 | Preparation process of ethylene sulfide |
| 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 |
| CN115028559A (en) * | 2021-07-12 | 2022-09-09 | 新疆上昵生物科技有限公司 | Preparation method of diethylaminoethanethiol |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE789629A (en) * | 1971-10-05 | 1973-04-03 | Sandoz Sa | NEW DERIVATIVES OF PLEUROMUTILINE, THEIR PREPARATION AND THERAPEUTIC APPLICATION |
| EP0289262A3 (en) * | 1987-04-27 | 1989-05-31 | Syntex Pharmaceuticals International Limited | Omega-quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal antiinflammatory drugs |
| CN100436409C (en) * | 2005-05-16 | 2008-11-26 | 北京大学 | Derivative of substitutional taurine and preparation method |
| CN101250145B (en) * | 2008-04-02 | 2010-08-18 | 苏州科技学院 | Method for preparing diethylamino ethanethiol |
-
2008
- 2008-12-19 CN CN200810080197A patent/CN101434567B/en active Active
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102153494A (en) * | 2011-03-04 | 2011-08-17 | 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 |
| CN104672206A (en) * | 2015-02-16 | 2015-06-03 | 张丽学 | Preparation process of ethylene sulfide |
| CN104774164A (en) * | 2015-02-16 | 2015-07-15 | 张丽学 | Preparation process for 2-diethylaminoethanethiol |
| CN105152990A (en) * | 2015-07-30 | 2015-12-16 | 宁夏泰瑞制药股份有限公司 | Preparation method for 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 |
| CN107011221A (en) * | 2017-03-03 | 2017-08-04 | 河北科技大学 | A kind of preparation method of diethylamino ethanethiol |
| CN109134425A (en) * | 2017-06-27 | 2019-01-04 | 保定加合精细化工有限公司 | A method of preparing high-purity thiirane |
| CN109134322A (en) * | 2017-06-27 | 2019-01-04 | 保定加合精细化工有限公司 | A method of preparing 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 |
| CN109608365A (en) * | 2018-12-10 | 2019-04-12 | 万华化学集团股份有限公司 | A kind of 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 |
| 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 |
| 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 |
| CN113735819A (en) * | 2020-05-29 | 2021-12-03 | 新疆上昵生物科技有限公司 | Preparation process of ethylene sulfide |
| 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 |
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| Publication number | Publication date |
|---|---|
| CN101434567B (en) | 2012-10-24 |
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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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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. |