CN105175291A - Synthesis method for lauroyl-sodium methyl taurate - Google Patents
Synthesis method for lauroyl-sodium methyl taurate Download PDFInfo
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- CN105175291A CN105175291A CN201510568940.5A CN201510568940A CN105175291A CN 105175291 A CN105175291 A CN 105175291A CN 201510568940 A CN201510568940 A CN 201510568940A CN 105175291 A CN105175291 A CN 105175291A
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- lauric acid
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Abstract
The invention discloses a high-conversion rate synthesis method for lauroyl-sodium methyl taurate. The high-conversion rate synthesis method comprises the following steps: mixing lauric acid with MgO, acetic acid and liquid paraffin; introducing nitrogen to replace air, heating to 100 DEG C to 110 DEG C and mixing for 5min; after heating, slowly dropwise adding N-sodium methyl taurate aqueous solution of which the mass fraction is 42 percent to 45 percent, controlling dropping speed so as to avoid the phenomenon that a large number of foams are generated from a reaction system and overflow, and continue to heat to 220 to 226 DEG C after the N-sodium methyl taurate aqueous solution is dropwise added and reacting for 4 to 5h; stop heating after the reaction is ended, and recovering. The high-conversion rate synthesis method disclosed by the invention is simple in process and easy in operation; the reaction time can be shortened, and the conversion rate (higher than 98 percent) of N-sodium methyl taurate is improved; after a crude product is recrystallized and dried, the purity of the crude product can reach more than 99 percent.
Description
Technical field
The present invention relates to a kind of synthetic method of lauroyl N-methyltaurine sodium, belong to chemical production field.
Background technology
Lauroyl N-methyltaurine sodium is the one in N-acyl amino acid type tensio-active agent; containing the sulfonic group be combined with amide group in its molecule; good compatibleness is had with negatively charged ion, nonionic, zwitterionics; be the higher anion surfactant of a kind of security, there is excellent water-soluble, stability in hard water, alkali resistance and acid resistance.Current industrial main Xiao Dun-Bao Man condensation method prepares lauroyl N-methyltaurine sodium ［ 4-5 ］, and N methyl taurine sodium transformation efficiency is generally about 90%, and product purity is about 95%.This technique easily causes environmental pollution in the process preparing lauroyl chloride, and simultaneously a large amount of sodium salt is difficult to recycle, and can cause product loss in repeatedly recrystallization purification process.And direct method preparation does not need acyl chloride reaction, product is without the need to desalting treatment simultaneously, and process cycle is short, green safety, and loss of material is few, has very large research application potential.
Prior art has to carry out linguistic term to direct preparation method; once equality (" with chemical industry "; 42nd volume the 1st phase; in February, 2012; " direct synthesis lauroyl N-methyltaurine sodium with lauric acid and N methyl taurine sodium for raw material ") synthesize lauroyl N-methyltaurine sodium through direct method condensation reaction, MgO has higher catalytic activity to this condensation reaction.The better synthetic technological condition obtained through optimum experimental is: the molar ratio of lauric acid and N methyl taurine sodium is 1.3:1, MgO consumption is 2% of lauric acid quality, and whiteruss consumption is 40% of lauric acid quality, at 215 DEG C, react 6h.Under optimal conditions, the transformation efficiency of N methyl taurine sodium can reach more than 95%, and thick product purity after recrystallization and drying treatment can reach more than 98%.
The present invention aims to provide a kind of synthetic method of new lauroyl N-methyltaurine sodium, and the reaction times is shorter, and N methyl taurine sodium transformation efficiency can reach more than 98%, and thick product purity after recrystallization and drying treatment can reach more than 99%.
Summary of the invention
Based on the technical problem that background technology exists; the present invention is directed to background technology Problems existing, provide a kind of synthetic method of new lauroyl N-methyltaurine sodium, the reaction times is shorter; transformation efficiency can reach more than 98%, and thick product purity after recrystallization and drying treatment can reach more than 99%.
Object of the present invention is achieved through the following technical solutions:
A kind of synthetic method of lauroyl N-methyltaurine sodium:
(1) mix lauric acid, MgO, acetate solution paraffin body, passing into nitrogen replacement air, being uniformly mixed 5min through being warming up to 100 DEG C-110 DEG C;
(2) after heating up, slowly drip the N methyl taurine sodium water solution of 42%-45% massfraction, control rate of addition in order to avoid reactive system produces a large amount of foam and overflows, drip off N methyl taurine sodium water solution follow-up continuous be warming up to 220-226 DEG C at react 4-5h;
(3) reacted rear stopping heating, material temperature injects water and hexanaphthene dissolving feed liquid successively after 150 DEG C, is filtered by lower aqueous solution recrystallization after stratification, and filter cake obtains product so that ethyl alcohol recrystallization filtration final vacuum is dry again; After upper strata oil reservoir steams hexanaphthene, paraffin layer cycling and reutilization;
The molar ratio of described lauric acid and N methyl taurine sodium is 1.3-1.5: 1, MgO consumption is 1% of lauric acid quality, and acetic acid consumption is the 0.6-0.8% of lauric acid quality, and whiteruss consumption is the 35-38% of lauric acid quality.
The present invention finds acetic acid and magnesium oxide acting in conjunction; the collaborative reaction conditions that other are optimized; significantly can reduce the reaction times, and improve the transformation efficiency (more than 98%) of N methyl taurine sodium, thick product purity after recrystallization and drying treatment can reach more than 99%.
Usefulness of the present invention is:
The simply good operation of present invention process, significantly can reduce the reaction times, and improves the transformation efficiency (more than 98%) of N methyl taurine sodium, and thick product purity after recrystallization and drying treatment can reach more than 99%.
Embodiment
embodiment 1:
A kind of synthetic method of lauroyl N-methyltaurine sodium:
Mixing lauric acid, MgO, acetate solution paraffin body, passing into nitrogen replacement air, being uniformly mixed 5min through being warming up to 100 DEG C;
After intensification, slowly drip the N methyl taurine sodium water solution of 45% massfraction, control rate of addition in order to avoid reactive system produces a large amount of foam and overflows, drip off N methyl taurine sodium water solution follow-up continuous be warming up to 220 DEG C at react 4h;
Reacted rear stopping heating, material temperature injects water and hexanaphthene dissolving feed liquid successively after 150 DEG C, is filtered by lower aqueous solution recrystallization after stratification, and filter cake obtains product so that ethyl alcohol recrystallization filtration final vacuum is dry again; After upper strata oil reservoir steams hexanaphthene, paraffin layer cycling and reutilization;
In reaction system, the molar ratio of lauric acid and N methyl taurine sodium is 1.3: 1, MgO consumption is 1% of lauric acid quality, and acetic acid consumption is 0.8% of lauric acid quality, and whiteruss consumption is 35% of lauric acid quality.
Conventionally ordinary method detects, and the transformation efficiency of N methyl taurine sodium can reach 99.2%, and thick product purity after recrystallization and drying treatment can reach 99%.
embodiment 2:
A kind of synthetic method of lauroyl N-methyltaurine sodium:
Mixing lauric acid, MgO, acetate solution paraffin body, passing into nitrogen replacement air, being uniformly mixed 5min through being warming up to 110 DEG C;
After intensification, slowly drip the N methyl taurine sodium water solution of 42% massfraction, control rate of addition in order to avoid reactive system produces a large amount of foam and overflows, drip off N methyl taurine sodium water solution follow-up continuous be warming up to 226 DEG C at react 4.5h;
Reacted rear stopping heating, material temperature injects water and hexanaphthene dissolving feed liquid successively after 150 DEG C, is filtered by lower aqueous solution recrystallization after stratification, and filter cake obtains product so that ethyl alcohol recrystallization filtration final vacuum is dry again; After upper strata oil reservoir steams hexanaphthene, paraffin layer cycling and reutilization;
In reaction system, the molar ratio of lauric acid and N methyl taurine sodium is 1.5: 1, MgO consumption is 1% of lauric acid quality, and acetic acid consumption is 0.6% of lauric acid quality, and whiteruss consumption is 38% of lauric acid quality.
Conventionally ordinary method detects, and the transformation efficiency of N methyl taurine sodium can reach 98%, and thick product purity after recrystallization and drying treatment can reach 98.0%.
embodiment 3:
A kind of synthetic method of lauroyl N-methyltaurine sodium:
Mixing lauric acid, MgO, acetate solution paraffin body, passing into nitrogen replacement air, being uniformly mixed 5min through being warming up to 105 DEG C;
After intensification, slowly drip the N methyl taurine sodium water solution of 44% massfraction, control rate of addition in order to avoid reactive system produces a large amount of foam and overflows, drip off N methyl taurine sodium water solution follow-up continuous be warming up to 221 DEG C at react 4h;
Reacted rear stopping heating, material temperature injects water and hexanaphthene dissolving feed liquid successively after 150 DEG C, is filtered by lower aqueous solution recrystallization after stratification, and filter cake obtains product so that ethyl alcohol recrystallization filtration final vacuum is dry again; After upper strata oil reservoir steams hexanaphthene, paraffin layer cycling and reutilization;
In reaction system, the molar ratio of lauric acid and N methyl taurine sodium is 1.4: 1, MgO consumption is 1% of lauric acid quality, and acetic acid consumption is 0.7% of lauric acid quality, and whiteruss consumption is 37% of lauric acid quality.
Conventionally ordinary method detects, and the transformation efficiency of N methyl taurine sodium can reach 99%, and thick product purity after recrystallization and drying treatment can reach 98.2%.
embodiment 4:
A kind of synthetic method of lauroyl N-methyltaurine sodium:
Mixing lauric acid, MgO, acetate solution paraffin body, passing into nitrogen replacement air, being uniformly mixed 5min through being warming up to 103 DEG C;
After intensification, slowly drip the N methyl taurine sodium water solution of 43% massfraction, control rate of addition in order to avoid reactive system produces a large amount of foam and overflows, drip off N methyl taurine sodium water solution follow-up continuous be warming up to 225 DEG C at react 5h;
Reacted rear stopping heating, material temperature injects water and hexanaphthene dissolving feed liquid successively after 150 DEG C, is filtered by lower aqueous solution recrystallization after stratification, and filter cake obtains product so that ethyl alcohol recrystallization filtration final vacuum is dry again; After upper strata oil reservoir steams hexanaphthene, paraffin layer cycling and reutilization;
In reaction system, the molar ratio of lauric acid and N methyl taurine sodium is 1.2: 1, MgO consumption is 1% of lauric acid quality, and acetic acid consumption is 0.6% of lauric acid quality, and whiteruss consumption is 36% of lauric acid quality.
Conventionally ordinary method detects, and the transformation efficiency of N methyl taurine sodium can reach 98.3%, and thick product purity after recrystallization and drying treatment can reach 98.1%.
embodiment 5:
A kind of synthetic method of lauroyl N-methyltaurine sodium:
Mixing lauric acid, MgO, acetate solution paraffin body, passing into nitrogen replacement air, being uniformly mixed 5min through being warming up to 109 DEG C;
After intensification, slowly drip the N methyl taurine sodium water solution of 45% massfraction, control rate of addition in order to avoid reactive system produces a large amount of foam and overflows, drip off N methyl taurine sodium water solution follow-up continuous be warming up to 222 DEG C at react 4.5h;
Reacted rear stopping heating, material temperature injects water and hexanaphthene dissolving feed liquid successively after 150 DEG C, is filtered by lower aqueous solution recrystallization after stratification, and filter cake obtains product so that ethyl alcohol recrystallization filtration final vacuum is dry again; After upper strata oil reservoir steams hexanaphthene, paraffin layer cycling and reutilization;
In reaction system, the molar ratio of lauric acid and N methyl taurine sodium is 1.3: 1, MgO consumption is 1% of lauric acid quality, and acetic acid consumption is 0.8% of lauric acid quality, and whiteruss consumption is 35% of lauric acid quality.
Conventionally ordinary method detects, and the transformation efficiency of N methyl taurine sodium can reach 98.9%, and thick product purity after recrystallization and drying treatment can reach 98.5%.
embodiment 6:
A kind of synthetic method of lauroyl N-methyltaurine sodium:
Mixing lauric acid, MgO, acetate solution paraffin body, passing into nitrogen replacement air, being uniformly mixed 5min through being warming up to 106 DEG C;
After intensification, slowly drip the N methyl taurine sodium water solution of 44% massfraction, control rate of addition in order to avoid reactive system produces a large amount of foam and overflows, drip off N methyl taurine sodium water solution follow-up continuous be warming up to 224 DEG C at react 5h;
Reacted rear stopping heating, material temperature injects water and hexanaphthene dissolving feed liquid successively after 150 DEG C, is filtered by lower aqueous solution recrystallization after stratification, and filter cake obtains product so that ethyl alcohol recrystallization filtration final vacuum is dry again; After upper strata oil reservoir steams hexanaphthene, paraffin layer cycling and reutilization;
In reaction system, the molar ratio of lauric acid and N methyl taurine sodium is 1.5: 1, MgO consumption is 1% of lauric acid quality, and acetic acid consumption is 0.7% of lauric acid quality, and whiteruss consumption is 38% of lauric acid quality.
Conventionally ordinary method detects, and the transformation efficiency of N methyl taurine sodium can reach 98.1%, and thick product purity after recrystallization and drying treatment can reach 98.3%.
As can be seen here, the simply good operation of present invention process, significantly can reduce the reaction times, and improves the transformation efficiency (more than 98%) of N methyl taurine sodium, and thick product purity after recrystallization and drying treatment can reach more than 99%.
The above; be only the present invention's preferably embodiment; but protection scope of the present invention is not limited thereto; anyly be familiar with those skilled in the art in the technical scope that the present invention discloses; be equal to according to technical scheme of the present invention and inventive concept thereof and replace or change, all should be encompassed within protection scope of the present invention.
Claims (5)
1. the synthetic method of a lauroyl N-methyltaurine sodium:
(1) mix lauric acid, MgO, acetate solution paraffin body, passing into nitrogen replacement air, being uniformly mixed 5min through being warming up to 100 DEG C-110 DEG C;
(2) after heating up, slowly drip the N methyl taurine sodium water solution of 42%-45% massfraction, control rate of addition in order to avoid reactive system produces a large amount of foam and overflows, drip off N methyl taurine sodium water solution follow-up continuous be warming up to 220-226 DEG C at react 3-4h;
(3) reacted rear stopping heating, material temperature injects water and hexanaphthene dissolving feed liquid successively after 150 DEG C, is filtered by lower aqueous solution recrystallization after stratification, and filter cake obtains product so that ethyl alcohol recrystallization filtration final vacuum is dry again; After upper strata oil reservoir steams hexanaphthene, paraffin layer cycling and reutilization.
2. the synthetic method of lauroyl N-methyltaurine sodium according to claim 1, is characterized in that:
The molar ratio of described lauric acid and N methyl taurine sodium is 1.3-1.5: 1, MgO consumption is 1% of lauric acid quality, and acetic acid consumption is the 0.6-0.8% of lauric acid quality, and whiteruss consumption is the 35-38% of lauric acid quality.
3. the synthetic method of lauroyl N-methyltaurine sodium according to claim 2, is characterized in that:
As preferably, after intensification, slowly drip the N methyl taurine sodium water solution of 45% massfraction, control rate of addition in order to avoid reactive system produces a large amount of foam and overflows, drip off N methyl taurine sodium water solution follow-up continuous be warming up to 220 DEG C at react 4h.
4. the synthetic method of lauroyl N-methyltaurine sodium according to claim 3, is characterized in that:
In reaction system, the molar ratio of lauric acid and N methyl taurine sodium is 1.3: 1, MgO consumption is 1% of lauric acid quality, and acetic acid consumption is 0.8% of lauric acid quality, and whiteruss consumption is 35% of lauric acid quality.
5. the synthetic method of lauroyl N-methyltaurine sodium according to claim 4, is characterized in that:
The transformation efficiency of N methyl taurine sodium can reach 99.2%, and thick product purity after recrystallization and drying treatment can reach 99%.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106588710A (en) * | 2016-12-12 | 2017-04-26 | 黄冈市富驰制药有限责任公司 | Method for synthesizing N-acyl-N-methyl taurine salt through microwave |
| CN111902395A (en) * | 2017-10-03 | 2020-11-06 | 荷兰联合利华有限公司 | Method for enhanced conversion of taurates to alkyltaurins |
| CN114031516A (en) * | 2021-11-23 | 2022-02-11 | 长沙普济生物科技股份有限公司 | Method for catalytically synthesizing N-acyl amino acid surfactant based on zirconium catalyst |
| CN114181119A (en) * | 2021-12-18 | 2022-03-15 | 黄冈永安日用化工有限公司 | Preparation method of methyl lauroyl sodium taurate |
| CN115160189A (en) * | 2022-08-11 | 2022-10-11 | 广州天赐高新材料股份有限公司 | Continuous preparation method of N-acyl methyl sodium taurate with high active matter content |
| CN115626884A (en) * | 2022-12-20 | 2023-01-20 | 江苏奥洁生物科技有限公司 | Method for synthesizing N-acyl amino acid surfactant |
| CN116199604A (en) * | 2021-12-27 | 2023-06-02 | 马鞍山科思化学有限公司 | Preparation method of high-quality cocoyl-N-methyl sodium taurate |
| US11999680B2 (en) | 2018-04-24 | 2024-06-04 | Conopco, Inc. | Enhanced conversion of taurine to alkyl taurate amide using phosphoric acid catalysts |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106588710B (en) * | 2016-12-12 | 2018-07-10 | 湖北远大生命科学与技术有限责任公司 | A kind of method of applied microwave synthesis N- acyl-N-methyl taurates |
| CN106588710A (en) * | 2016-12-12 | 2017-04-26 | 黄冈市富驰制药有限责任公司 | Method for synthesizing N-acyl-N-methyl taurine salt through microwave |
| CN111902395B (en) * | 2017-10-03 | 2022-12-09 | 联合利华知识产权控股有限公司 | Method for enhanced conversion of taurates to alkyltaurinamides |
| CN111902395A (en) * | 2017-10-03 | 2020-11-06 | 荷兰联合利华有限公司 | Method for enhanced conversion of taurates to alkyltaurins |
| US11999680B2 (en) | 2018-04-24 | 2024-06-04 | Conopco, Inc. | Enhanced conversion of taurine to alkyl taurate amide using phosphoric acid catalysts |
| CN114031516A (en) * | 2021-11-23 | 2022-02-11 | 长沙普济生物科技股份有限公司 | Method for catalytically synthesizing N-acyl amino acid surfactant based on zirconium catalyst |
| CN114031516B (en) * | 2021-11-23 | 2023-09-01 | 长沙普济生物科技股份有限公司 | Method for synthesizing N-acyl amino acid surfactant based on zirconium catalyst catalysis |
| CN114181119A (en) * | 2021-12-18 | 2022-03-15 | 黄冈永安日用化工有限公司 | Preparation method of methyl lauroyl sodium taurate |
| CN116199604A (en) * | 2021-12-27 | 2023-06-02 | 马鞍山科思化学有限公司 | Preparation method of high-quality cocoyl-N-methyl sodium taurate |
| CN116199604B (en) * | 2021-12-27 | 2023-12-19 | 马鞍山科思化学有限公司 | Preparation method of high-quality cocoyl-N-methyl sodium taurate |
| CN115160189A (en) * | 2022-08-11 | 2022-10-11 | 广州天赐高新材料股份有限公司 | Continuous preparation method of N-acyl methyl sodium taurate with high active matter content |
| CN115626884A (en) * | 2022-12-20 | 2023-01-20 | 江苏奥洁生物科技有限公司 | Method for synthesizing N-acyl amino acid surfactant |
| WO2024130837A1 (en) * | 2022-12-20 | 2024-06-27 | 江苏奥洁生物科技有限公司 | Method for synthesizing n-acyl amino acid surfactant |
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