CN114031511A - Synthesis method of benzethonium chloride - Google Patents
Synthesis method of benzethonium chloride Download PDFInfo
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- CN114031511A CN114031511A CN202111387808.6A CN202111387808A CN114031511A CN 114031511 A CN114031511 A CN 114031511A CN 202111387808 A CN202111387808 A CN 202111387808A CN 114031511 A CN114031511 A CN 114031511A
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- benzethonium chloride
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
Abstract
The invention belongs to the technical field of chemistry, and particularly relates to a method for synthesizing benzethonium chloride. The invention takes dichloroethyl ether, octylphenol and the like as raw materials, and the synthesis is carried out by two steps, meanwhile, in the synthesis process, compared with the prior art, the temperature is kept lower, in addition, in the synthesis process, high pressure is not used, the yield in the synthesis process is higher, and the purity is better.
Description
Technical Field
The invention belongs to the technical field of chemistry, and particularly relates to a method for synthesizing benzethonium chloride.
Background
Benzethonium chloride is a novel cationic surfactant, is easy to dissolve in water to form a foamy soap water sample solution, and is widely used as a daily chemical additive. Benzethonium chloride also has good sterilizing and antiseptic effects, and is widely applied to the field of medicine as a new generation of detergent, bactericide and antiseptic.
Currently, benzethonium chloride is mainly produced by using p-tert-octylphenol, dichlorodiethyl ether, dimethylamine and benzyl chloride as raw materials to synthesize benzethonium chloride. The process approach needs ammonolysis reaction which can be carried out under the conditions of high temperature and high pressure, and has larger potential safety hazard.
Disclosure of Invention
Aiming at the problems: in view of the above problems, the present invention provides a method for synthesizing benzethonium chloride.
A method for synthesizing benzethonium chloride comprises the following steps:
(1) putting 52 mass percent of sodium hydroxide solution, dichloroethyl ether, a phase transfer catalyst and octylphenol into a reactor, stirring, heating, and carrying out heat preservation reaction to obtain a compound A;
(2) uniformly stirring the compound A, benzyl dimethylamine and water, carrying out nitrogen protection, heating, reacting and cooling to obtain benzethonium chloride;
preferably, the phase transfer catalyst in the step (1) is benzyltriethylammonium chloride.
Preferably, the mass ratio of the sodium hydroxide solution with the mass fraction of 52% in the step (1), the dichloroethyl ether, the phase transfer catalyst and the octylphenol is 90:80: 0.6-0.8: 30.
Preferably, the mass ratio of the compound A, the benzyldimethylamine and the water in the step (2) is 45:20: 30-35.
Has the advantages that:
the invention takes dichloroethyl ether, octylphenol and the like as raw materials, and the synthesis is carried out by two steps, meanwhile, in the synthesis process, compared with the prior art, the temperature is kept lower, in addition, in the synthesis process, high pressure is not used, the yield in the synthesis process is higher, and the purity is better.
Detailed Description
A method for synthesizing benzethonium chloride comprises the following steps:
(1) taking materials according to the mass ratio of 52% sodium hydroxide solution, dichloroethyl ether, phase transfer catalyst and octylphenol of 90:80: 0.6-0.8: 30, putting 52% sodium hydroxide solution, dichloroethyl ether, phase transfer catalyst and octylphenol into a reactor, stirring, heating, and carrying out heat preservation reaction to obtain a compound A; the phase transfer catalyst is benzyltriethylammonium chloride;
(2) taking materials according to the mass ratio of the compound A, the benzyl dimethylamine and the water of 45:20: 30-35, uniformly stirring the compound A, the benzyl dimethylamine and the water, carrying out nitrogen protection, heating, reacting and cooling to obtain the benzethonium chloride.
Example 1
A method for synthesizing benzethonium chloride comprises the following steps:
(1) putting 900kg of sodium hydroxide solution with the mass fraction of 52% into a reaction kettle, adding 800kg of dichloroethyl ether, 6kg of phase transfer catalyst and 300kg of octylphenol, starting stirring, slowly heating up, heating up to reflux, keeping the temperature for 3 hours, tracking and detecting the reaction process by TLC (thin layer chromatography), adding water into the reaction kettle, washing and layering, separating an organic layer, washing for 1 time by using water, recovering the solvent by using the organic phase under reduced pressure, and distilling under reduced pressure to obtain 513kg of a compound A with the purity of 97.8%;
(2) putting 450kg of compound A, 200kg of benzyldimethylamine and 300kg of water into a reaction kettle, starting stirring, replacing with nitrogen, protecting with nitrogen, heating to 115 ℃, continuing to react for 7 hours, cooling, discharging, transferring to a dehydration kettle, then adding 400kg of toluene, heating for refluxing, dehydrating, freezing and crystallizing, filtering, drying, recrystallizing with 1000kg of acetone again, cooling, crystallizing, filtering, and drying to obtain 731kg of benzethonium chloride with the purity of 98.9%.
1H NMR（CDCl3）:7.66(m, 2H), 7.43(m, 1H), 7.35(m, 2H), 7.24(m, 2H), 6.76(m, 2H), 5.03(s, 2H), 4.09(m, 2H), 4.06(m, 2H), 3.91(m, 2H), 3.85(m, 2H), 3.32(s, 6H), 1.68(s, 2H), 1.32(s, 6H), 0.69(s, 9H)。
Example 2
A method for synthesizing benzethonium chloride comprises the following steps:
(1) putting 900kg of sodium hydroxide solution with the mass fraction of 52% into a reaction kettle, adding 800kg of dichloroethyl ether, 7kg of phase transfer catalyst and 300kg of octylphenol, starting stirring, slowly heating up, heating up to reflux, keeping the temperature for 3 hours, tracking and detecting the reaction process by TLC (thin layer chromatography), adding water into the reaction kettle, washing and layering, separating an organic layer, washing for 1 time by using water, recovering the solvent by using the organic phase under reduced pressure, and distilling under reduced pressure to obtain 546kg of a compound A with the purity of 98.8%;
(2) putting 450kg of compound A, 200kg of benzyldimethylamine and 330kg of water into a reaction kettle, starting stirring, replacing with nitrogen, protecting with nitrogen, heating to 115 ℃, continuing to react for 7 hours, cooling, discharging, transferring to a dehydration kettle, then adding 400kg of toluene, heating for refluxing, dehydrating, freezing and crystallizing, filtering, drying, recrystallizing with 1000kg of acetone again, cooling, crystallizing, filtering, and drying to obtain 731kg of benzethonium chloride with the purity of 99.3%.
1H NMR（CDCl3）:7.66(m, 2H), 7.43(m, 1H), 7.35(m, 2H), 7.24(m, 2H), 6.76(m, 2H), 5.03(s, 2H), 4.09(m, 2H), 4.06(m, 2H), 3.91(m, 2H), 3.85(m, 2H), 3.32(s, 6H), 1.68(s, 2H), 1.32(s, 6H), 0.69(s, 9H)。
Example 3
A method for synthesizing benzethonium chloride comprises the following steps:
(1) putting 900kg of sodium hydroxide solution with the mass fraction of 52% into a reaction kettle, adding 800kg of dichloroethyl ether, 0.8kg of phase transfer catalyst and 300kg of octylphenol, starting stirring, slowly heating up, heating to reflux, keeping the temperature for 3 hours, tracking and detecting the reaction process by TLC (thin layer chromatography), adding water into the reaction kettle, washing and layering, separating out an organic layer, washing for 1 time by using water, recovering the solvent by using the organic phase under reduced pressure, and distilling under reduced pressure to obtain 518kg of a compound A with the purity of 98.3%;
(2) putting 450kg of compound A, 200kg of benzyldimethylamine and 350kg of water into a reaction kettle, starting stirring, replacing with nitrogen, protecting with nitrogen, heating to 115 ℃, continuing to react for 7 hours, cooling, discharging, transferring to a dehydration kettle, then adding 400kg of toluene, heating for refluxing, dehydrating, freezing, crystallizing, filtering, drying, recrystallizing with 1000kg of acetone again, cooling, crystallizing, filtering, and drying to obtain 722kg of benzethonium chloride with the purity of 98.4%.
1H NMR（CDCl3）:7.66(m, 2H), 7.43(m, 1H), 7.35(m, 2H), 7.24(m, 2H), 6.76(m, 2H), 5.03(s, 2H), 4.09(m, 2H), 4.06(m, 2H), 3.91(m, 2H), 3.85(m, 2H), 3.32(s, 6H), 1.68(s, 2H), 1.32(s, 6H), 0.69(s, 9H)。
Claims (4)
1. The method for synthesizing benzethonium chloride is characterized by comprising the following steps:
(1) putting 52 mass percent of sodium hydroxide solution, dichloroethyl ether, a phase transfer catalyst and octylphenol into a reactor, stirring, heating, and carrying out heat preservation reaction to obtain a compound A;
(2) uniformly stirring the compound A, benzyl dimethylamine and water, carrying out nitrogen protection, heating, reacting and cooling to obtain benzethonium chloride;
2. the method for synthesizing benzethonium chloride as claimed in claim 1, wherein the phase transfer catalyst in step (1) is benzyltriethylammonium chloride.
3. The method for synthesizing benzethonium chloride as claimed in claim 1, wherein the mass ratio of 52% sodium hydroxide solution, dichloroethyl ether, phase transfer catalyst and octylphenol in step (1) is 90:80: 0.6-0.8: 30.
4. The method for synthesizing benzethonium chloride as claimed in claim 1, wherein the mass ratio of compound A, benzyldimethylamine and water in step (2) is 45:20: 30-35.
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| CN202111387808.6A CN114031511A (en) | 2021-11-23 | 2021-11-23 | Synthesis method of benzethonium chloride |
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| CN202111387808.6A CN114031511A (en) | 2021-11-23 | 2021-11-23 | Synthesis method of benzethonium chloride |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116924922A (en) * | 2023-09-18 | 2023-10-24 | 内蒙古圣氏化学股份有限公司 | Method for continuously producing benzethonium chloride |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN183696B (en) * | 1997-10-03 | 2000-03-18 | Vivimed Labs Ltd | |
| CN102993031A (en) * | 2011-09-19 | 2013-03-27 | 北京桑普生物化学技术有限公司 | Preparation process of aromatic polyoxyalkyl quaternary ammonium compound |
| CN109651177A (en) * | 2018-12-20 | 2019-04-19 | 江西省隆南药化有限公司 | A kind of preparation method of benzethonium chloride |
| CN113372227A (en) * | 2021-06-29 | 2021-09-10 | 扬州虹光生物科技有限公司 | Synthesis process of high-purity benzethonium chloride |
-
2021
- 2021-11-23 CN CN202111387808.6A patent/CN114031511A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN183696B (en) * | 1997-10-03 | 2000-03-18 | Vivimed Labs Ltd | |
| CN102993031A (en) * | 2011-09-19 | 2013-03-27 | 北京桑普生物化学技术有限公司 | Preparation process of aromatic polyoxyalkyl quaternary ammonium compound |
| CN109651177A (en) * | 2018-12-20 | 2019-04-19 | 江西省隆南药化有限公司 | A kind of preparation method of benzethonium chloride |
| CN113372227A (en) * | 2021-06-29 | 2021-09-10 | 扬州虹光生物科技有限公司 | Synthesis process of high-purity benzethonium chloride |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116924922A (en) * | 2023-09-18 | 2023-10-24 | 内蒙古圣氏化学股份有限公司 | Method for continuously producing benzethonium chloride |
| CN116924922B (en) * | 2023-09-18 | 2023-11-21 | 内蒙古圣氏化学股份有限公司 | Method for continuously producing benzethonium chloride |
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Effective date of registration: 20221011 Address after: 225652 Tianshan Industrial Concentration Zone, Songqiao Town, Gaoyou City, Yangzhou City, Jiangsu Province Applicant after: Yangzhou Avision Biotechnology Co.,Ltd. Address before: 751908 south of Anqing Avenue, Taiyangshan immigration Development Zone, Wuzhong City, Ningxia Hui Autonomous Region Applicant before: Ningxia Changsheng Pharmaceutical Co.,Ltd. |