CN113307751A - Process for producing aliphatic mercaptan - Google Patents
Process for producing aliphatic mercaptan Download PDFInfo
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- CN113307751A CN113307751A CN202110554277.9A CN202110554277A CN113307751A CN 113307751 A CN113307751 A CN 113307751A CN 202110554277 A CN202110554277 A CN 202110554277A CN 113307751 A CN113307751 A CN 113307751A
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
- C07D331/02—Three-membered rings
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Abstract
The present invention provides a novel preparation of (CH)3CH2)2NCH2CH2The SH method is that the reaction is carried out at a lower temperature, and the reaction is controllable by adopting a dropwise feeding mode, thereby realizing safe production.
Description
Technical Field
The invention relates to the field of chemical industry, in particular to (CH)3CH2)2NCH2CH2A method for preparing SH.
Background
(CH3CH2)2NCH2CH2SH is an important intermediate for synthesizing veterinary drugs and is reported in the literature (CH)3CH2)2NCH2CH2Many SH synthesis methods, such as a hydrosulfide route, a thiocyanate route, a benzylmercaptan route and a thiourea route, all of which use diethylaminoethanol as a starting material, basically have the problems of long reaction route, low yield, many byproducts, difficult purification of products and the like; as another example, the ethyl chloroformate route is not only long, but also uses the highly toxic substance hydroxy ethanethiol. The compounds currently widely used in industry are those composed of thiacyclopropane and (CH)3CH2)2Reaction of NH to (CH)3CH2)2NCH2CH2And (5) SH. The existing method generally has violent reaction and certain potential safety hazard. It is therefore necessary to carry out the existing preparation (CH)3CH2)2NCH2CH2The method of SH is optimized.
Disclosure of Invention
The present invention provides a novel preparation of (CH)3CH2)2NCH2CH2The SH method is that the reaction is carried out at a lower temperature, and the reaction is controllable by adopting a dropwise feeding mode, thereby realizing safe production.
The reaction scheme in the process of the invention is as follows:
wherein A ═ Na+Or K+
According to one aspect of the present invention, there is provided a (CH)3CH2)2NCH2CH2The preparation method of SH comprises the following steps: heating (CH)3CH2)2NH to reflux, then dripping thiirane, controlling the temperature at about 50-58 ℃ and the pressure at about 0-0.7MPa after dripping to reflux and react for about 6-8 hours, and then distilling and recovering (CH)3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2And (5) SH. Preferably, the temperature is controlled to be about 50 to 58 ℃ and the pressure is controlled to be about 0 to 0.7MPa during the dropping of the thietane. Preferably, the dropping time is 1.5 to 2 hours.
According to the invention, thiacyclopropane and (CH)3CH2)2The molar ratio of NH is 1:1.5-2.5, preferably 1: 1.8-2.2.
It will be understood by those skilled in the art that the pressure is a pressure of a pressure gauge, and when the reaction pressure is 0Mpa, the reaction pressure is the same as the atmospheric pressure. The pressure is greater than 0 by passing an inert gas such as nitrogen. Preferably, the pressure during the dropping and/or during the reflux reaction is 0.1 to 0.5 MPa.
Preferably, the method further comprises the following steps: (CH) to be recovered3CH2)2Dropping NH into inorganic acid solution, and controlling the temperature below 30 deg.C to obtain (CH)3CH2)2A salt of NH.
According to the present invention, an inorganic acid solution such as a hydrochloric acid solution, a phosphoric acid solution, a sulfuric acid solution, a nitric acid solution, or the like.
According to the invention, (CH)3CH2)2The molar ratio of NH to acid contained in the acid solution is 1:10-10: 1.
Preferably, the inorganic acid solution is a hydrochloric acid solution, (CH)3CH2)2The molar ratio of NH to hydrochloric acid contained in the hydrochloric acid solution was 1:1.
Preferably, in the present invention, a currently used thietane is used. The thienylcyclopropane can be prepared by the following method: anhydrous thiocyanate salt is taken, molten ethylene carbonate is added with stirring, the reaction is carried out at about 70-75 ℃ until no thietane is distilled off, and the distilled thietane is collected by condensation.
According to the invention, the molar ratio of thiocyanate to ethylene carbonate is 1: 0.8-1.4.
According to the invention, the thiocyanate is sodium thiocyanate, potassium thiocyanate.
The invention has the advantages that the reaction is carried out at a lower temperature, and the reaction is controllable by adopting a dropwise feeding mode, thereby realizing safe production.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Furthermore, it should be understood that various changes or modifications can be made by those skilled in the art after reading the description of the present invention, and such equivalents also fall within the scope of the invention.
In the present application, the following method is used to detect (CH)3CH2)2NH and (CH)3CH2)2Hydrochloride salt of NH:
(CH3CH2)2the NH detection method comprises the following steps:
detection by gas Chromatography (CH)3CH2)2NH purity, chromatographic conditions:
a detector: column temperature of hydrogen flame ionization detector: 80 deg.C
A detector: sample introduction at 200 ℃: 0.2. mu.L
Hydrogen gas: 40. + -.2 mL/min air: 400 plus or minus 5mL/min
Nitrogen gas: 30mL/min
And injecting the sample after the equipment is stable and the baseline is stable. And (3) sucking 0.2 mu L of sample by a sample injection needle, injecting the sample into a chromatograph, collecting for at least 10min, and obtaining the gas phase purity by using a normalization method. The average value of the two needles is the detection result, and the deviation of the two needles is not more than 0.3%.
(CH3CH2)2Detection method of hydrochloride of NH:
accurately weighing 0.2g (accurate to 0.0001g) of a sample to be detected, placing the sample in a conical flask, adding 50mL of distilled water, adding 5mL of 2% dextrin after dissolving, adding a fluorescent indicator, titrating the sample with a silver nitrate standard solution until the yellow green color is changed into reddish, recording the reading, and calculating the result.
Example 1
(1) 461kg of anhydrous sodium thiocyanate was charged into a reaction kettle, 651kg of molten ethylene carbonate was added under stirring, heated to about 70 ℃ to react until no thietane was distilled off, and 300kg of distilled thietane was collected by condensation, with a yield of 87.9%.
(2) Adding (CH) into a reaction kettle3CH2)2NH 401.5kg, slowly heating to reflux, then dropwise adding 150kg of the thiirane in the step (1), wherein the dropwise adding time is 1.5 hours, the temperature is controlled to be 50-58 ℃ in the dropwise adding process, the pressure is normal pressure, namely the gauge pressure is 0MPa, and the temperature is controlled to be 50-58 ℃ after the dropwise adding is finishedReflux reaction at normal pressure, i.e. gauge pressure of 0MPa for 8 hours, and then distillation recovery of (CH)3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2SH 306kg, the yield is 92.03%.
Comparative example 1
Adding (CH) into a reaction kettle3CH2)2NH 401.5kg, slowly heating to reflux, then dropwise adding 150kg of thiirane obtained in the step (1) in the example 1, wherein the dropwise adding time is 1.5 hours, the temperature is controlled to be 50-58 ℃ and the pressure is controlled to be normal pressure, namely the gauge pressure is 0MPa, after the dropwise adding is finished, the temperature is controlled to be 80-85 ℃ and the pressure is controlled to be normal pressure, namely the gauge pressure is 0MPa, carrying out reflux reaction for 4 hours, and then distilling and recovering (CH)3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2SH 280kg, yield 84.2%.
Example 2
(1) 467.2kg of anhydrous potassium thiocyanate was charged into a reaction vessel, 339kg of molten ethylene carbonate was added under stirring, the reaction was heated to about 75 ℃ until no thietane was distilled off, and 200kg of distilled thietane was collected by condensation, with a yield of 86.5%.
(2) Adding (CH) into a reaction kettle3CH2)2NH 365kg, slowly heating to reflux, then dropwise adding 200kg of the thiirane in the step (1), wherein the dropwise adding time is 2 hours, the temperature is controlled to be 50-58 ℃ in the dropwise adding process, nitrogen is introduced to ensure that the pressure is 0.5-0.7MP under gauge pressure, after the dropwise adding is finished, the temperature is controlled to be 50-58 ℃ and nitrogen is introduced to ensure that the pressure is 0.5-0.7MP under gauge pressure to reflux and react for 6 hours, and then distilling and recovering (CH)3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2SH 421kg, the yield is 95.0%.
(3) Recovering (CH) from step (2)3CH2)2Adding NH 142kg (purity about 92%) into 217kg of 30% hydrochloric acid solution, controlling the temperature below about 30 deg.C, and centrifuging to obtain (CH)3CH2)2Hydrochloride salt of NH, yield 85.2%, purity 99.5%.
Example 3
(1) 465kg of anhydrous sodium thiocyanate was added into a reaction kettle, 555.7kg of molten ethylene carbonate was added under stirring, the mixture was heated to about 72 ℃ to react until no thietane was distilled off, 303.3kg of distilled thietane was collected by condensation, and the yield was 88.1%.
(2) Adding (CH) into a reaction kettle3CH2)2NH 553.5kg, slowly heating to reflux, then dropwise adding 303.3kg of the thietane propane in the step (1), wherein the dropwise adding time is 1.5 hours, the temperature is controlled to be 50-58 ℃ in the dropwise adding process, nitrogen is introduced to ensure that the pressure is 0.2-0.3MP under gauge pressure, after the dropwise adding is finished, the temperature is controlled to be 50-58 ℃ and nitrogen is introduced to ensure that the pressure is 0.2-0.3MP under gauge pressure to reflux for 7 hours, and then distilling and recovering (CH)3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2SH 634.5kg, the yield is 94.4%.
Example 4
(1) 922.0g of anhydrous sodium thiocyanate was charged into a reaction vessel, 1302.0g of molten ethylene carbonate was added with stirring, the reaction was heated to about 70 ℃ until no thietane was distilled off, and 600.0g of distilled thietane was collected by condensation, with a yield of 87.9%.
(2) Adding (CH) into a reaction kettle3CH2)2NH 803.0g, slowly heating to reflux, then dropwise adding 300.0g of the thiirane in the step (1), wherein the dropwise adding time is 1.5 hours, the temperature is controlled to be 50-58 ℃ and the pressure is 0MPa under normal pressure, namely gauge pressure, in the dropwise adding process, the temperature is controlled to be 50-58 ℃ and the pressure is 0MPa under normal pressure after dropwise adding, reflux reaction is carried out for 8 hours, and then distillation recovery (CH) is carried out3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2SH 612.0g, yield 92.03%.
Comparative example 4-1
Adding (CH) into a reaction kettle3CH2)2NH 803g was slowly heated to reflux, and 300.0g of thietane (1) of example 4 was added dropwise over a period of 1.5 hoursControlling the temperature at 50-58 deg.C and the pressure at normal pressure, i.e. gauge pressure of 0MPa, controlling the temperature at 80-85 deg.C and the pressure at normal pressure, i.e. gauge pressure of 0MPa, reflux-reacting for 4 hours after the dripping is finished, and then distilling and recovering (CH)3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2SH 560.0g, yield 84.2%.
In comparison with the comparative example 4-1, the reaction is controlled to be carried out at a lower temperature, so that the reaction can be controlled, the safe production can be realized, and the reaction yield can be improved.
Comparative example 4 to 2
The procedure in example 4 (1) was repeated to obtain thietane. Adding (CH) into a reaction kettle3CH2)2NH 803.0g, slowly heating to reflux, adding 300.0g of heterocyclic sulfur propane, controlling the temperature at 80-85 ℃, refluxing and reacting for 4 hours under the pressure of normal pressure, namely gauge pressure of 0MPa, and then distilling and recovering (CH)3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2SH 540.0g, yield 81.2%.
In comparison with the comparative example 4-2, the dropwise addition method is adopted, so that the reaction is controllable, the safe production is realized, and the reaction yield can be improved.
Example 5
(1) 934.4g of anhydrous potassium thiocyanate was added to the reaction kettle, 678.0g of molten ethylene carbonate was added with stirring, the mixture was heated to about 75 ℃ to react until no thietane was distilled off, and 400.0g of distilled thietane was collected by condensation, with a yield of 86.4%.
(2) Adding (CH) into a reaction kettle3CH2)2NH 790.0g, slowly heating to reflux, dropwise adding 400.0g of the thiirane in the step (1), dropwise adding for 2 hours, controlling the temperature to be 50-58 ℃ in the dropwise adding process, introducing nitrogen to ensure that the pressure is 0.5-0.7MP under gauge pressure, controlling the temperature to be 50-58 ℃ after dropwise adding is finished, introducing nitrogen to ensure that the pressure is 0.5-0.7MP under gauge pressure to reflux for 6 hours, and then distilling and recovering (CH)3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2SH 842.0g, yield 94.9%.
(3) Recovering (CH) from step (2)3CH2)2Adding NH 284.0g (purity about 92%) dropwise into 434.0g 30% hydrochloric acid solution, controlling temperature below about 30 deg.C, centrifuging, and throwing to obtain (CH)3CH2)2NH hydrochloride 340.0g, yield 86.8%, content 99.5%.
Example 6
(1) 930.0g of anhydrous sodium thiocyanate was charged into a reaction kettle, 1111.4g of molten ethylene carbonate was added with stirring, the mixture was heated to about 72 ℃ to react until no thietane was distilled off, 606.6g of distilled thietane was collected by condensation, and the yield was 87.9%.
(2) Adding (CH) into a reaction kettle3CH2)2NH 1107g is slowly heated to reflux, then 606.6g of the thietane in the step (1) is dripped for 1.5 hours, the temperature is controlled to be 50-58 ℃ in the dripping process, nitrogen is introduced to ensure that the pressure is 0.2-0.3MP under gauge pressure, the temperature is controlled to be 50-58 ℃ after the dripping is finished, nitrogen is introduced to ensure that the pressure is 0.2-0.3MP under gauge pressure to carry out reflux reaction for 7 hours, and then (CH) is distilled and recovered3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2SH 1269g, yield 94.4%.
Example 7
(1) 930.0g of anhydrous sodium thiocyanate was charged into a reaction kettle, 1111.4g of molten ethylene carbonate was added with stirring, the mixture was heated to about 72 ℃ to react until no thietane was distilled off, 606.2g of distilled thietane was collected by condensation, and the yield was 87.9%.
(2) Adding (CH) into a reaction kettle3CH2)2NH 1107g is slowly heated to reflux, then 606.2g of the thietane in the step (1) is dripped, the dripping time is 1.8 hours, the temperature is controlled to be 50-58 ℃ in the dripping process, the pressure is normal pressure, namely the gauge pressure is 0MPa, the reflux reaction is carried out for 7.5 hours after the dripping is finished, the temperature is controlled to be 50-58 ℃ and the pressure is normal pressure, namely the gauge pressure is 0MPa, and then the distillation recovery (CH) is carried out3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2SH 1266.0g, yield 94.2%.
Example 8
(1) 920.0g of anhydrous potassium thiocyanate was added to a reaction kettle, 700.0g of molten ethylene carbonate was added with stirring, the mixture was heated to about 72 ℃ to react until no thietane was distilled off, and 410.0g of distilled thietane was collected by condensation, with a yield of 85.7%.
(2) Adding (CH) into a reaction kettle3CH2)2NH 790.0g, slowly heating to reflux, then dropwise adding 410.0g of the thiirane obtained in the step (1), wherein the dropwise adding time is 1.8 hours, the temperature is controlled to be 50-58 ℃ in the dropwise adding process, the pressure is normal pressure, namely the gauge pressure is 0MPa, after the dropwise adding is finished, the temperature is controlled to be 50-58 ℃, nitrogen is introduced to ensure that the reflux reaction is carried out for 6.5 hours under the gauge pressure of 0.3-0.5MPa, and then the distillation recovery (CH)3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2SH 856.0g, yield 94.1%.
Example 9
(1) 300.0kg of anhydrous sodium thiocyanate was charged into a large reactor, 475.0kg of molten ethylene carbonate was added with stirring, the reaction was heated to about 70 ℃ until no thietane distilled off, 195.2kg of distilled thietane was collected by condensation, and the yield was 87.7%.
(2) Adding (CH) into a large-scale reaction kettle3CH2)2NH 300.0kg, slowly heating to reflux, then dripping 195.2kg of the thietane in the step (1) for 1.5 hours, controlling the temperature at 50-58 ℃ and the pressure at normal pressure, namely gauge pressure, 0MPa in the dripping process, controlling the temperature at 50-58 ℃ and the pressure at normal pressure, namely gauge pressure, to reflux and react for 8 hours after the dripping is finished, and then distilling and recovering (CH)3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2SH 410kg, the yield is 94.7%.
Example 10
(1) 350.0kg of anhydrous potassium thiocyanate was charged into a large reaction vessel, 475.0kg of molten ethylene carbonate was added under stirring, the reaction was heated to about 75 ℃ until no thietane distilled off, and 188.7kg of the distilled thietane was collected by condensation with a yield of 87.1%.
(2) Adding (CH) into a reaction kettle3CH2)2NH 350.0kg, slowly heating to reflux, then dropwise adding 188.7kg of the thiirane obtained in the step (1), wherein the dropwise adding time is 2 hours, the temperature is controlled to be 50-58 ℃ in the dropwise adding process, nitrogen is introduced to ensure that the pressure is 0.5-0.7MP under gauge pressure, after the dropwise adding is finished, the temperature is controlled to be 50-58 ℃ and nitrogen is introduced to ensure that the pressure is 0.5-0.7MP under gauge pressure to reflux and react for 6 hours, and then distilling and recovering (CH)3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2SH 395.0kg, the yield is 94.4%.
The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiment. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. (CH)3CH2)2NCH2CH2The preparation method of SH is characterized by comprising the following steps: heating (CH)3CH2)2NH to reflux, then dripping thiirane, controlling the temperature at about 50-58 ℃ and the pressure at about 0-0.7MPa after dripping to reflux and react for about 6-8 hours, and then distilling and recovering (CH)3CH2)2NH, and then (CH) is distilled off3CH2)2NCH2CH2SH, preferably, the temperature is controlled to be about 50 to 58 ℃ and the pressure is controlled to be about 0 to 0.7MPa during the dropping of the thietane.
2. The production method according to claim 1, wherein the dropping time is 1.5 to 2 hours.
3. The process according to claim 1, wherein the thiirane is a thiirane(CH3CH2)2The molar ratio of NH is 1:1.5-2.5, preferably 1: 1.8-2.2.
4. The process of claim 1, wherein the pressure is from 0.1 to 0.5MPa gauge.
5. The method of claim 1, further comprising the steps of: (CH) to be recovered3CH2)2Dropping NH into inorganic acid solution, and controlling the temperature below 30 deg.C to obtain (CH)3CH2)2A salt of NH.
6. The method according to claim 5, wherein the inorganic acid solution is a hydrochloric acid solution, a phosphoric acid solution, a sulfuric acid solution, or the like.
7. The method of claim 6, wherein (CH)3CH2)2The molar ratio of NH to acid contained in the acid solution is 1:10-10: 1.
Preferably, the inorganic acid solution is a hydrochloric acid solution, (CH)3CH2)2The molar ratio of NH to hydrochloric acid contained in the hydrochloric acid solution was 1:1.
8. The process according to claim 1, wherein the thietane is prepared by: anhydrous thiocyanate salt is taken, molten ethylene carbonate is added with stirring, the reaction is carried out at about 70-75 ℃ until no thietane is distilled off, and the distilled thietane is collected by condensation.
9. The process according to claim 8, wherein the molar ratio of thiocyanate to ethylene carbonate is from 1:0.8 to 1.4.
10. The method according to claim 8, wherein the thiocyanate is sodium thiocyanate or potassium thiocyanate.
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| CN2020116434542 | 2020-12-31 | ||
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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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| 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 |
| 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 |
| 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 |
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| CN101434567A (en) * | 2008-12-19 | 2009-05-20 | 段新峰 | Preparation of lignocaine ethanethiol |
| 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 |
| 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 |
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| 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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