CN101585791A - Method for preparing N, N-diethylamino ethanethiol - Google Patents
Method for preparing N, N-diethylamino ethanethiol Download PDFInfo
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- CN101585791A CN101585791A CNA2009103039604A CN200910303960A CN101585791A CN 101585791 A CN101585791 A CN 101585791A CN A2009103039604 A CNA2009103039604 A CN A2009103039604A CN 200910303960 A CN200910303960 A CN 200910303960A CN 101585791 A CN101585791 A CN 101585791A
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- diethylamino ethanethiol
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- thiirane
- thiocyanate
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Abstract
The present invention relates to a method for preparing N, N-diethylamino ethanethiol, belonging to a chemical technical field. The method includes steps of a. heating rhodanides and ethylene carbonate to react under ordinary pressure, distilling to obtain Thiirane after the reaction, the general formula of the rhodanides is M-SCN, wherein M is alkali metal of Na or K; b. mixing and stirring the Thiirane and diethylamine in a toluene dissolvant, heating under an ordinary pressure to implement a backflow reaction and distilling to obtain the N, N-diethylamino ethanethiol after the backflow reaction. The method has a short synthesis technical process, the kind of the raw materials is few and source is wide, the used toluene dissolvant may be recovered, and there will generate little waste water, waste gas and waste which may reduce environmental pollution.
Description
Technical field
The present invention relates to a kind of preparation method of medicine intermediate, relate in particular to a kind of N, the preparation method of N-diethylamino ethanethiol belongs to technical field of chemistry.
Background technology
N, N-diethylamino ethanethiol are important medicine intermediate raw materials, and the effect in agricultural chemicals, medicine are produced is increasing, and along with the widespread use of this product, the demand to this product increases year by year in the world.
The operational path of producing this product is many, and diethylamine commonly used at present and reacting ethylene oxide obtain diethylaminoethanol, obtains diethyllaminoethyl chlorine with the thionyl chloride reaction again.Diethyllaminoethyl chlorine and sulfhydryl compound generation replacement(metathesis)reaction obtain product N, the N-diethylamino ethanethiol, but exist the synthesis technique long flow path, the three wastes are many, raw material type is many and originate difficulty.
Summary of the invention
The present invention is directed to existing N, preparation method's above shortcomings of N-diethylamino ethanethiol provide a kind of N, the preparation method of N-diethylamino ethanethiol.
The technical scheme that the present invention solves the problems of the technologies described above is as follows: a kind of N of the present invention, and the preparation method of N-diethylamino ethanethiol, this method may further comprise the steps:
Step a: the reacting by heating under normal pressure with thiocyanate-and NSC 11801, distillation obtained thiirane after reaction finished,
Wherein, the general formula of described thiocyanate-is M-SCN,
In the formula, M is Alkali-Metal Na, K,
Step b: described thiirane is mixed stirring with diethylamine in toluene solvant, carry out back flow reaction after the heating under normal pressure, distillation obtained N, N-diethylamino ethanethiol after reaction finished.
The invention has the beneficial effects as follows: N of the present invention, the synthesis technique flow process of N-diethylamino ethanethiol is short, the few and wide material sources of raw materials used kind, and the toluene solvant of use is also recyclable to be utilized again, and the waste water, waste gas and the refuse that produce are few, can reduce the pollution to environment.
On the basis of technique scheme, the present invention can also do following improvement.
Further, the temperature of reacting by heating is 100 ℃～150 ℃ among the described step a.
Further, the time of reacting by heating is 5 hours～10 hours among the described step a.
Further, the mol ratio of thiocyanate-and NSC 11801 is 1: 1～1: 5 among the described step a.
Further, thiocyanate-is Sodium Thiocyanate 99 or potassium sulfocyanate among the described step a.
Further, described thiocyanate-is a Sodium Thiocyanate 99.
Further, the temperature of reacting by heating is 50 ℃～80 ℃ among the described step b.
Further, the time of back flow reaction is 15 hours～25 hours among the described step b.
Further, the mol ratio of thiirane and diethylamine is 1: 1～1: 3 among the described step b.
Further, when thiirane was 1 mole among the described step b, described diethylamine was 1 mole～3 moles, and corresponding described toluene solvant is 200 milliliters.
Embodiment
Below in conjunction with principle of the present invention and feature are described, institute gives an actual example and only is used to explain the present invention, is not to be used to limit scope of the present invention.
Below with four embodiment to N of the present invention, the preparation method of N-diethylamino ethanethiol is described in further detail.
Wherein embodiment 1,2 and 3 generates thiirane with potassium sulfocyanate and NSC 11801 reaction, and reaction generates N with diethylamine again, the N-diethylamino ethanethiol, and the equation of described reaction is:
Wherein embodiment 4,5 and 6 generates thiirane with Sodium Thiocyanate 99 and NSC 11801 reaction, and reaction generates N with diethylamine again, the N-diethylamino ethanethiol, and the equation of described reaction is:
Embodiment 1:
Step a: the NSC 11801 of 1 mole potassium sulfocyanate and 1 mole is added in the reaction flask, heat temperature raising to 100 ℃ under normal pressure, be incubated 7 hours, it is that 54 ℃～56 ℃ cut is thiirane 49g that reaction distills out boiling point after finishing, content through the gas chromatographic analysis product is 99.7%, and yield is 81.4%.
Step b: 1 mole thiirane, 1 mole diethylamine and 200ml toluene are added in the reaction flask, heat temperature raising to 50 ℃ carries out back flow reaction under normal pressure, keep refluxing 15 hours, it is that 160 ℃～162 ℃ cut is product N that reaction distills out boiling point after finishing, N-diethylamino ethanethiol 127.6g, content through the gas chromatographic analysis product is 99.5%, and yield is 95.5%.
Embodiment 2:
Step a: the NSC 11801 of 1 mole potassium sulfocyanate and 5 moles is added in the reaction flask, heat temperature raising to 130 ℃ under normal pressure, be incubated 10 hours, it is that 54 ℃～56 ℃ cut is thiirane 48.5g that reaction distills out boiling point after finishing, content through the gas chromatographic analysis product is 99.6%, and yield is 80.5%.
Step b: 1 mole thiirane, 1.8 moles diethylamine and 200ml toluene are added in the reaction flask, heat temperature raising to 60 ℃ carries out back flow reaction under normal pressure, keep refluxing 21 hours, it is that 160 ℃～162 ℃ cut is product N that reaction distills out boiling point after finishing, N-diethylamino ethanethiol 127.9g, content through the gas chromatographic analysis product is 99.6%, and yield is 95.8%.
Embodiment 3:
Step a: the NSC 11801 of 1 mole potassium sulfocyanate and 3 moles is added in the reaction flask, heat temperature raising to 150 ℃ under normal pressure, be incubated 5 hours, it is that 54 ℃～56 ℃ cut is thiirane 49g that reaction distills out boiling point after finishing, content through the gas chromatographic analysis product is 99.7%, and yield is 81.4%.
Step b: 1 mole thiirane, 3 moles diethylamine and 200ml toluene are added in the reaction flask, heat temperature raising to 80 ℃ carries out back flow reaction under normal pressure, keep refluxing 25 hours, it is that 160 ℃～162 ℃ cut is product N that reaction distills out boiling point after finishing, N-diethylamino ethanethiol 127.6g, content through the gas chromatographic analysis product is 99.5%, and yield is 95.5%.
Embodiment 4:
Step a: the NSC 11801 of 1 mole Sodium Thiocyanate 99 and 1 mole is added in the reaction flask, heat temperature raising to 100 ℃ under normal pressure, be incubated 7 hours, it is that 54 ℃～56 ℃ cut is thiirane 49.5g that reaction distills out boiling point after finishing, content through the gas chromatographic analysis product is 99.5%, and yield is 82.0%.
Step b: 1 mole thiirane, 1 mole diethylamine and 200ml toluene are added in the reaction flask, heat temperature raising to 50 ℃ carries out back flow reaction under normal pressure, keep refluxing 15 hours, it is that 160 ℃～162 ℃ cut is product N that reaction distills out boiling point after finishing, N-diethylamino ethanethiol 127.8g, content through the gas chromatographic analysis product is 99.6%, and yield is 95.7%.
Embodiment 5:
Step a: the NSC 11801 of 1 mole Sodium Thiocyanate 99 and 5 moles is added in the reaction flask, heat temperature raising to 130 ℃ under normal pressure, be incubated 10 hours, it is that 54 ℃～56 ℃ cut is thiirane 49g that reaction distills out boiling point after finishing, content through the gas chromatographic analysis product is 99.7%, and yield is 81.4%.
Step b: 1 mole thiirane, 1.8 moles diethylamine and 200ml toluene are added in the reaction flask, heat temperature raising to 60 ℃ carries out back flow reaction under normal pressure, keep refluxing 21 hours, it is that 160 ℃～162 ℃ cut is product N that reaction distills out boiling point after finishing, N-diethylamino ethanethiol 127.6g, content through the gas chromatographic analysis product is 99.6%, and yield is 95.6%.
Embodiment 6:
Step a: the NSC 11801 of 1 mole Sodium Thiocyanate 99 and 3 moles is added in the reaction flask, heat temperature raising to 150 ℃ under normal pressure, be incubated 5 hours, it is that 54 ℃～56 ℃ cut is thiirane 49.5g that reaction distills out boiling point after finishing, content through the gas chromatographic analysis product is 99.5%, and yield is 82.1%.
Step b: 1 mole thiirane, 3 moles diethylamine and 200ml toluene are added in the reaction flask, heat temperature raising to 80 ℃ carries out back flow reaction under normal pressure, keep refluxing 25 hours, it is that 160 ℃～162 ℃ cut is product N that reaction distills out boiling point after finishing, N-diethylamino ethanethiol 127.8g, through the content 99.6% of gas chromatographic analysis product, yield is 95.7%.
The above only is preferred embodiment of the present invention, and is in order to restriction the present invention, within the spirit and principles in the present invention not all, any modification of being done, is equal to replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (10)
1. N, the preparation method of N-diethylamino ethanethiol, this method may further comprise the steps:
Step a: the reacting by heating under normal pressure with thiocyanate-and NSC 11801, distillation obtained thiirane after reaction finished,
Wherein, the general formula of described thiocyanate-is M-SCN,
In the formula, M is Alkali-Metal Na, K,
Step b: described thiirane is mixed stirring with diethylamine in toluene solvant, carry out back flow reaction after the heating under normal pressure, distillation obtained N, N-diethylamino ethanethiol after reaction finished.
2. N according to claim 1, the method for the preparation of N-diethylamino ethanethiol is characterized in that: the temperature of reacting by heating is 100 ℃～150 ℃ among the described step a.
3. N according to claim 1, the preparation method of N-diethylamino ethanethiol is characterized in that: the time of reacting by heating is 5 hours～10 hours among the described step a.
4. N according to claim 1, the preparation method of N-diethylamino ethanethiol is characterized in that: the mol ratio of thiocyanate-and NSC 11801 is 1: 1～1: 5 among the described step a.
5. N according to claim 1, the preparation method of N-diethylamino ethanethiol is characterized in that: thiocyanate-is Sodium Thiocyanate 99 or potassium sulfocyanate among the described step a.
6. N according to claim 5, the preparation method of N-diethylamino ethanethiol is characterized in that: described thiocyanate-is a Sodium Thiocyanate 99.
7. N according to claim 1, the preparation method of N-diethylamino ethanethiol is characterized in that: the temperature of reacting by heating is 50 ℃～80 ℃ among the described step b.
8. N according to claim 1, the preparation method of N-diethylamino ethanethiol is characterized in that: the time of back flow reaction is 15 hours～25 hours among the described step b.
9. N according to claim 1, the preparation method of N-diethylamino ethanethiol is characterized in that: the mol ratio of thiirane and diethylamine is 1: 1～1: 3 among the described step b.
10. N according to claim 1, the preparation method of N-diethylamino ethanethiol is characterized in that: when thiirane was 1 mole among the described step b, described diethylamine was 1 mole～3 moles, and corresponding described toluene solvant is 200 milliliters.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CNA2009103039604A CN101585791A (en) | 2008-09-23 | 2009-07-02 | Method for preparing N, N-diethylamino ethanethiol |
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| CN200810211710.3 | 2008-09-23 | ||
| CNA2008102117103A CN101407483A (en) | 2008-09-23 | 2008-09-23 | Method for preparing amino mercapto compound |
| CNA2009103039604A CN101585791A (en) | 2008-09-23 | 2009-07-02 | Method for preparing N, N-diethylamino ethanethiol |
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| CNA2008102117103A Pending CN101407483A (en) | 2008-09-23 | 2008-09-23 | Method for preparing amino mercapto compound |
| CNA2009103039604A Pending CN101585791A (en) | 2008-09-23 | 2009-07-02 | Method for preparing N, N-diethylamino ethanethiol |
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Cited By (11)
| 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 |
| 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 |
| 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 |
| CN113372248A (en) * | 2021-06-11 | 2021-09-10 | 保定北瑞甾体生物有限公司 | Process for preparing thiols |
| 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 |
| CN113387857A (en) * | 2020-03-11 | 2021-09-14 | 新疆上昵生物科技有限公司 | Synthesis process of diethylaminoethanethiol |
| CN113735747A (en) * | 2020-05-29 | 2021-12-03 | 新疆上昵生物科技有限公司 | Method for producing tiamulin by using diethylaminoethanethiol synthetic solution |
| CN113943236A (en) * | 2020-07-17 | 2022-01-18 | 新疆上昵生物科技有限公司 | Method for continuously preparing diethylaminoethanethiol |
| CN115028559A (en) * | 2021-07-12 | 2022-09-09 | 新疆上昵生物科技有限公司 | Preparation method of diethylaminoethanethiol |
| CN116265437A (en) * | 2021-12-16 | 2023-06-20 | 保定加合精细化工有限公司 | Method for stabilizing thiol compositions |
-
2008
- 2008-09-23 CN CNA2008102117103A patent/CN101407483A/en active Pending
-
2009
- 2009-07-02 CN CNA2009103039604A patent/CN101585791A/en active Pending
Cited By (14)
| 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 |
| 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 |
| 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 |
| 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 |
| CN113387857A (en) * | 2020-03-11 | 2021-09-14 | 新疆上昵生物科技有限公司 | Synthesis process of diethylaminoethanethiol |
| CN113735747A (en) * | 2020-05-29 | 2021-12-03 | 新疆上昵生物科技有限公司 | Method for producing tiamulin by using diethylaminoethanethiol synthetic solution |
| CN113735747B (en) * | 2020-05-29 | 2024-07-02 | 新疆上昵生物科技有限公司 | Method for producing tiamulin by diethylaminoethanethiol synthetic solution |
| CN113943236A (en) * | 2020-07-17 | 2022-01-18 | 新疆上昵生物科技有限公司 | Method for continuously preparing diethylaminoethanethiol |
| CN113943236B (en) * | 2020-07-17 | 2024-05-03 | 新疆上昵生物科技有限公司 | Continuous preparation method of diethylaminoethanethiol |
| 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 |
| CN116265437A (en) * | 2021-12-16 | 2023-06-20 | 保定加合精细化工有限公司 | Method for stabilizing thiol compositions |
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| CN101407483A (en) | 2009-04-15 |
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