CN105175291B - A kind of synthetic method of lauroyl N-methyltaurine sodium - Google Patents
A kind of synthetic method of lauroyl N-methyltaurine sodium Download PDFInfo
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- CN105175291B CN105175291B CN201510568940.5A CN201510568940A CN105175291B CN 105175291 B CN105175291 B CN 105175291B CN 201510568940 A CN201510568940 A CN 201510568940A CN 105175291 B CN105175291 B CN 105175291B
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- laurate
- methyltaurine sodium
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- sodium
- lauroyl
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Abstract
The invention discloses a kind of high conversion synthetic method of lauroyl N-methyltaurine sodium：Laurate, MgO, acetic acid atoleine are mixed, nitrogen displacement air is passed through, 5min is stirred through being warming up to 100 DEG C 110 DEG C；After heating, the N N-methyltaurine sodium water solutions of 42% 45% mass fractions are slowly added dropwise, control rate of addition is continuously heating to react 4 5h at 220 226 DEG C in order to avoid reaction system produces a large amount of foams and overflowed after dripping off N N-methyltaurine sodium water solutions；Stop heating, recovery after the completion of reaction.Present invention process simply operates well, can shorten the reaction time, and improves the conversion ratio of N N-methyltaurine sodium（More than 98%）, crude product after recrystallization and drying process purity up to more than 99%.
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 one kind in N- acyl amino acid type surfactants, contain in its molecule with
The sulfonic group that amide groups combines, has good compatibility with anion, nonionic, zwitterionic surfactant, is a kind of peace
The higher anion surfactant of full property, has excellent water solubility, stability in hard water, alkali resistance and acid resistance.Industry at present
On mainly prepare lauroyl N-methyltaurine sodium ［ 4-5 ］, N-N-methyltaurine sodium conversion ratio one with Xiao Dun-Bao Man condensation methods
As 90% or so, product purity is 95% or so.The technique easily causes environmental pollution during lauroyl chloride is prepared,
A large amount of sodium salts are difficult to recycle simultaneously, product can be caused to lose in repeated recrystallize purification process.And direct method is prepared not
Acyl chloride reaction is needed, while product, without desalting processing, process cycle is short, green safe, and loss of material is few, has very big grind
Study carefully application potential.
Prior art is improved research to direct preparation method, once equality（《Use chemical industry》, volume 42
1st phase, 2 months 2012, " direct synthesis lauroyl N-methyltaurine sodium was with laurate and N-N-methyltaurine sodium
For raw material "）Lauroyl N-methyltaurine sodium is synthesized through direct method condensation reaction, MgO has higher to the condensation reaction
Catalytic activity.The preferable synthetic technological condition obtained through optimum experimental is:Laurate feeds intake with N-N-methyltaurine sodium
Mol ratio is 1. 3：1, MgO dosage is the 2% of laurate quality, and atoleine dosage is the 40% of laurate quality, at 215 DEG C
6 h of lower reaction.The conversion ratio of N-N-methyltaurine sodium is up to more than 95% under optimal conditions, and crude product is through recrystallizing and drying
Purity is up to more than 98% after processing.
The present invention is intended to provide a kind of synthetic method of new lauroyl N-methyltaurine sodium, the reaction time is shorter, N-
N-methyltaurine sodium conversion ratio up to more than 98%, crude product after recrystallization and drying process purity up to more than 99%.
The content of the invention
Based on technical problem existing for background technology, the problem of present invention exists for background technology, there is provided a kind of new
The synthetic method of lauroyl N-methyltaurine sodium, the reaction time is shorter, and conversion ratio is up to more than 98%, and crude product is through recrystallization
And after drying process purity up to more than 99%.
The purpose of the present invention is achieved through the following technical solutions：
A kind of synthetic method of lauroyl N-methyltaurine sodium：
（1）Laurate, MgO, acetic acid atoleine are mixed, nitrogen displacement air is passed through, is stirred through being warming up to 100 DEG C -110 DEG C
Mix mixing 5min；
（2）After heating, the N methyl taurine sodium water solution of 42%-45% mass fractions is slowly added dropwise, controls rate of addition
In order to avoid reaction system produces a large amount of foams and overflowed, 220-226 DEG C is continuously heating to after dripping off N methyl taurine sodium water solution
Lower reaction 4-5h；
（3）Stop heating after the completion of reaction, material temperature is implanted sequentially water and hexamethylene dissolving feed liquid, stood after being less than 150 DEG C
Lower aqueous solution is recrystallized after layering and filtered, filter cake is dried in vacuo to obtain product after being filtered again with ethyl alcohol recrystallization;Upper strata oil reservoir
After steaming hexamethylene, paraffin layer cycling and reutilization；
The molar ratio of the laurate and N methyl taurine sodium is that 1.3-1.5: 1, MgO dosages are laurate matter
The 1% of amount, acetic acid dosage are the 0.6-0.8% of laurate quality, and atoleine dosage is the 35-38% of laurate quality.
Present invention discover that by acetic acid and magnesia collective effect, the reaction condition for cooperateing with other to optimize, can significantly drop
The low reaction time, and improve the conversion ratio of N-N-methyltaurine sodium（More than 98%）, crude product is through recrystallization and drying process
Purity is up to more than 99% afterwards.
The present invention is advantageous in that：
Present invention process simply operates well, and the reaction time can be greatly lowered, and improves N-N-methyltaurine sodium
Conversion ratio（More than 98%）, crude product after recrystallization and drying process purity up to more than 99%.
Embodiment
Embodiment 1：
A kind of synthetic method of lauroyl N-methyltaurine sodium：
Laurate, MgO, acetic acid atoleine are mixed, nitrogen displacement air is passed through, is stirred through being warming up to 100 DEG C
5min；
After heating, the N methyl taurine sodium water solution of 45% mass fraction is slowly added dropwise, controls rate of addition in order to avoid reacting
System produces a large amount of foams and overflowed, and is continuously heating to react 4h at 220 DEG C after dripping off N methyl taurine sodium water solution；
Stop heating after the completion of reaction, material temperature is implanted sequentially water and hexamethylene dissolving feed liquid, standing point after being less than 150 DEG C
Lower aqueous solution is recrystallized after layer and filtered, filter cake is dried in vacuo to obtain product after being filtered again with ethyl alcohol recrystallization;Upper strata oil reservoir steams
After going out hexamethylene, paraffin layer cycling and reutilization；
The molar ratio of laurate and N methyl taurine sodium is that 1.3: 1, MgO dosages are laurate in reaction system
The 1% of quality, acetic acid dosage are the 0.8% of laurate quality, and atoleine dosage is the 35% of laurate quality.
Detected according to prior art conventional method, the conversion ratio of N-N-methyltaurine sodium is up to 99.2%, crude product
Purity is up to 99% after recrystallization and drying process.
Embodiment 2：
A kind of synthetic method of lauroyl N-methyltaurine sodium：
Laurate, MgO, acetic acid atoleine are mixed, nitrogen displacement air is passed through, is stirred through being warming up to 110 DEG C
5min；
After heating, the N methyl taurine sodium water solution of 42% mass fraction is slowly added dropwise, controls rate of addition in order to avoid reacting
System produces a large amount of foams and overflowed, and is continuously heating to react 4.5h at 226 DEG C after dripping off N methyl taurine sodium water solution；
Stop heating after the completion of reaction, material temperature is implanted sequentially water and hexamethylene dissolving feed liquid, standing point after being less than 150 DEG C
Lower aqueous solution is recrystallized after layer and filtered, filter cake is dried in vacuo to obtain product after being filtered again with ethyl alcohol recrystallization;Upper strata oil reservoir steams
After going out hexamethylene, paraffin layer cycling and reutilization；
The molar ratio of laurate and N methyl taurine sodium is that 1.5: 1, MgO dosages are laurate in reaction system
The 1% of quality, acetic acid dosage are the 0.6% of laurate quality, and atoleine dosage is the 38% of laurate quality.
Detected according to prior art conventional method, up to 98%, crude product passes through the conversion ratio of N-N-methyltaurine sodium
Purity is up to 98.0% after recrystallization and drying process.
Embodiment 3：
A kind of synthetic method of lauroyl N-methyltaurine sodium：
Laurate, MgO, acetic acid atoleine are mixed, nitrogen displacement air is passed through, is stirred through being warming up to 105 DEG C
5min；
After heating, the N methyl taurine sodium water solution of 44% mass fraction is slowly added dropwise, controls rate of addition in order to avoid reacting
System produces a large amount of foams and overflowed, and is continuously heating to react 4h at 221 DEG C after dripping off N methyl taurine sodium water solution；
Stop heating after the completion of reaction, material temperature is implanted sequentially water and hexamethylene dissolving feed liquid, standing point after being less than 150 DEG C
Lower aqueous solution is recrystallized after layer and filtered, filter cake is dried in vacuo to obtain product after being filtered again with ethyl alcohol recrystallization;Upper strata oil reservoir steams
After going out hexamethylene, paraffin layer cycling and reutilization；
The molar ratio of laurate and N methyl taurine sodium is that 1.4: 1, MgO dosages are laurate in reaction system
The 1% of quality, acetic acid dosage are the 0.7% of laurate quality, and atoleine dosage is the 37% of laurate quality.
Detected according to prior art conventional method, up to 99%, crude product passes through the conversion ratio of N-N-methyltaurine sodium
Purity is up to 98.2% after recrystallization and drying process.
Embodiment 4：
A kind of synthetic method of lauroyl N-methyltaurine sodium：
Laurate, MgO, acetic acid atoleine are mixed, nitrogen displacement air is passed through, is stirred through being warming up to 103 DEG C
5min；
After heating, the N methyl taurine sodium water solution of 43% mass fraction is slowly added dropwise, controls rate of addition in order to avoid reacting
System produces a large amount of foams and overflowed, and is continuously heating to react 5h at 225 DEG C after dripping off N methyl taurine sodium water solution；
Stop heating after the completion of reaction, material temperature is implanted sequentially water and hexamethylene dissolving feed liquid, standing point after being less than 150 DEG C
Lower aqueous solution is recrystallized after layer and filtered, filter cake is dried in vacuo to obtain product after being filtered again with ethyl alcohol recrystallization;Upper strata oil reservoir steams
After going out hexamethylene, paraffin layer cycling and reutilization；
The molar ratio of laurate and N methyl taurine sodium is that 1.2: 1, MgO dosages are laurate in reaction system
The 1% of quality, acetic acid dosage are the 0.6% of laurate quality, and atoleine dosage is the 36% of laurate quality.
Detected according to prior art conventional method, the conversion ratio of N-N-methyltaurine sodium is up to 98.3%, crude product
Purity is up to 98.1% after recrystallization and drying process.
Embodiment 5：
A kind of synthetic method of lauroyl N-methyltaurine sodium：
Laurate, MgO, acetic acid atoleine are mixed, nitrogen displacement air is passed through, is stirred through being warming up to 109 DEG C
5min；
After heating, the N methyl taurine sodium water solution of 45% mass fraction is slowly added dropwise, controls rate of addition in order to avoid reacting
System produces a large amount of foams and overflowed, and is continuously heating to react 4.5h at 222 DEG C after dripping off N methyl taurine sodium water solution；
Stop heating after the completion of reaction, material temperature is implanted sequentially water and hexamethylene dissolving feed liquid, standing point after being less than 150 DEG C
Lower aqueous solution is recrystallized after layer and filtered, filter cake is dried in vacuo to obtain product after being filtered again with ethyl alcohol recrystallization;Upper strata oil reservoir steams
After going out hexamethylene, paraffin layer cycling and reutilization；
The molar ratio of laurate and N methyl taurine sodium is that 1.3: 1, MgO dosages are laurate in reaction system
The 1% of quality, acetic acid dosage are the 0.8% of laurate quality, and atoleine dosage is the 35% of laurate quality.
Detected according to prior art conventional method, the conversion ratio of N-N-methyltaurine sodium is up to 98.9%, crude product
Purity is up to 98.5% after recrystallization and drying process.
Embodiment 6：
A kind of synthetic method of lauroyl N-methyltaurine sodium：
Laurate, MgO, acetic acid atoleine are mixed, nitrogen displacement air is passed through, is stirred through being warming up to 106 DEG C
5min；
After heating, the N methyl taurine sodium water solution of 44% mass fraction is slowly added dropwise, controls rate of addition in order to avoid reacting
System produces a large amount of foams and overflowed, and is continuously heating to react 5h at 224 DEG C after dripping off N methyl taurine sodium water solution；
Stop heating after the completion of reaction, material temperature is implanted sequentially water and hexamethylene dissolving feed liquid, standing point after being less than 150 DEG C
Lower aqueous solution is recrystallized after layer and filtered, filter cake is dried in vacuo to obtain product after being filtered again with ethyl alcohol recrystallization;Upper strata oil reservoir steams
After going out hexamethylene, paraffin layer cycling and reutilization；
The molar ratio of laurate and N methyl taurine sodium is that 1.5: 1, MgO dosages are laurate in reaction system
The 1% of quality, acetic acid dosage are the 0.7% of laurate quality, and atoleine dosage is the 38% of laurate quality.
Detected according to prior art conventional method, the conversion ratio of N-N-methyltaurine sodium is up to 98.1%, crude product
Purity is up to 98.3% after recrystallization and drying process.
As can be seen here, present invention process simply operates well, and the reaction time can be greatly lowered, and improves N-methyl
The conversion ratio of sodium taurocholate（More than 98%）, crude product after recrystallization and drying process purity up to more than 99%.
The foregoing is only a preferred embodiment of the present invention, but protection scope of the present invention be not limited thereto,
Any one skilled in the art the invention discloses technical scope in, technique according to the invention scheme and its
Inventive concept is subject to equivalent substitution or change, should all be included within the scope of the present invention.
Claims (1)
1. a kind of synthetic method of lauroyl N-methyltaurine sodium, it is characterised in that step is as follows：
Laurate, MgO, acetic acid, atoleine are mixed, nitrogen displacement air is passed through, 5min is stirred through being warming up to 100 DEG C；
After heating, the N methyl taurine sodium water solution of 45% mass fraction is slowly added dropwise, control rate of addition is in order to avoid reaction system
Produce a large amount of foams and overflow, be continuously heating to react 4h at 220 DEG C after dripping off N methyl taurine sodium water solution；
Stop heating after the completion of reaction, material temperature is implanted sequentially water and hexamethylene dissolving feed liquid after being less than 150 DEG C, after stratification
Lower aqueous solution is recrystallized and filtered, filter cake is dried in vacuo to obtain product after being filtered again with ethyl alcohol recrystallization;Upper strata oil reservoir steams ring
After hexane, paraffin layer cycling and reutilization；
The molar ratio of laurate and N methyl taurine sodium is that 1.3: 1, MgO dosages are laurate quality in reaction system
1%, acetic acid dosage be laurate quality 0.8%, atoleine dosage be laurate quality 35%；
Detected according to prior art conventional method, the conversion ratio of N-N-methyltaurine sodium is up to 99.2%, and crude product is through weight
Purity is up to 99% after crystallization and drying process.
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| 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 |
| EP3692016A1 (en) * | 2017-10-03 | 2020-08-12 | Unilever PLC | Method of enhanced conversion of taurine salts to alkyl taurate amides |
| 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 |
| CN114181119B (en) * | 2021-12-18 | 2023-04-18 | 湖北天安日用化工有限公司 | Preparation method of methyl lauroyl 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 |
| CN115160189B (en) * | 2022-08-11 | 2023-06-16 | 广州天赐高新材料股份有限公司 | Continuous preparation method of N-acyl methyl sodium taurate |
| CN115626884B (en) * | 2022-12-20 | 2023-04-07 | 江苏奥洁生物科技有限公司 | Method for synthesizing N-acyl amino acid surfactant |
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| US3420858A (en) * | 1964-12-11 | 1969-01-07 | Lever Brothers Ltd | Process for the production of fatty acid esters of hydroxy sulfonates |
| US5496959A (en) * | 1994-05-23 | 1996-03-05 | Hoechst Celanese Corporation | Preparation of N-acyl taurates |
| JP2002234868A (en) * | 2001-02-08 | 2002-08-23 | Rekkutekku Laboratories Kk | Method for producing acyltaurine salt |
| CN1323069C (en) * | 2005-01-25 | 2007-06-27 | 上海奥利实业有限公司 | Synthesis of high-purity N-acyl-N-methyl sodium sulfate |
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