CN106588710B - A kind of method of applied microwave synthesis N- acyl-N-methyl taurates - Google Patents
A kind of method of applied microwave synthesis N- acyl-N-methyl taurates Download PDFInfo
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- CN106588710B CN106588710B CN201611139830.8A CN201611139830A CN106588710B CN 106588710 B CN106588710 B CN 106588710B CN 201611139830 A CN201611139830 A CN 201611139830A CN 106588710 B CN106588710 B CN 106588710B
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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Abstract
The present invention relates to the methods of the field of chemical synthesis more particularly to a kind of applied microwave synthesis N acyl group N methyl taurides.This method under solvent-free conditions, utilizes microwave heating using the aliphatic acid of C8 18, N methyl taurides as raw material; N acyl group N methyl taurides are directly synthesized, cooling is beaten with 90 100% ethyl alcohol; filtering, then washed with 90 100% ethyl alcohol, it is dried in vacuo to obtain sterling.This method raw material is easy to get, reaction condition is mild, it is environmentally protective, be simple and efficient, suitable for industrialized production.
Description
Technical field
The present invention relates to the field of chemical synthesis, and N- acyl-N-methyl taurines are synthesized more particularly, to a kind of applied microwave
The method of salt.
Background technology
N- acyl-N-methyl taurate classes belong to anion surfactant, have excellent washing, wetting, emulsification
With soft ability, foaming abundancy, exquisiteness, stabilization.With good detergency and emulsifiability, resistance to hard water, resistance to acid and alkali, with the moon
The conformability of ion, nonionic and amphoteric surfactant is good.Such surfactant is green safe and easily biological-degradable, property
Mildly, structure containing hydrophilic amino acid is very small to skin irritation.
The synthesis N- acyl-N-methyls taurate reported at present is mostly that aliphatic acid is made acyl chlorides, then in alkali
It is reacted under the conditions of property, it is post-treated to obtain product.This kind of method, can generate a large amount of acidity during fat acyl chloride is prepared
Waste water, fat acyl chloride also easily hydrolysis, alkaline condition reaction during using and storing can generate during post processing
A large amount of brine wastes, it is also necessary to use a large amount of organic solvents, these are all polluted the environment, and the reaction time is also long, are received
Rate is not also high.
CN105175290A is reported using lauric acid, N methyl taurine sodium as raw material, utilizes magnesia, boric acid, acetic acid
Although the method for catalyzing and synthesizing lauroyl N-methyltaurine sodium, this method are avoided using acyl chlorides, product without desalination at
Reason, but operation other auxiliary materials comparatively laborious, used are also relatively more, also there is certain pollution to environment.In addition, using this
The method reaction time at least needs 5-8 hours.
It is therefore desirable to find a reaction condition is mild, the environmentally protective, new method that is simple and efficient synthesis N- acyl groups-
N methyl taurine salt.
Invention content
The purpose is to provide, a raw material is easy to get the present invention, reaction condition is mild, environmentally protective, the synthesis N- that is simple and efficient
The new method of acyl-N-methyl taurate is asked with solving big, high expensive of environmental pollution present in existing production method etc.
Topic.
Technical solution of the present invention：
A kind of method of applied microwave synthesis N- acyl-N-methyl taurates, the method synthesis path are：
Wherein, M=sodium, potassium, ammonium；
Include the following steps：
1) it using aliphatic acid, N methyl taurine salt as raw material, under solvent-free conditions, using microwave heating, directly synthesizes
N- acyl-N-methyl taurates；
2) after reaction, to be cooled to 0-20 DEG C, the ethyl alcohol mashing of 90-100%, filtering are added in, then use 90-100%
Ethyl alcohol washing, be dried in vacuo to obtain sterling.
Preferably, the amount ratio of the step 1) aliphatic acid and the substance of N methyl taurine salt is 1.05-1.50.
It is further preferred that the step 1) aliphatic acid is the aliphatic acid of C8-18.
It is further preferred that the step 1) aliphatic acid is lauric acid, myristic acid, palmitic acid or coconut oil.
Preferably, the power of the step 1) microwave is 100-1000W, and the frequency of microwave is 2450MHz.
It is further preferred that the power of the step 1) microwave is 300-600W, the frequency of microwave is 2450MHz.
Preferably, the step 1) reaction temperature is 100-200 DEG C, reaction time 10-60min.
It is further preferred that the step 1) reaction temperature is 120-180 DEG C, reaction time 10-50min.
It is further preferred that the step 1) reaction temperature is 150-180 DEG C, reaction time 10-35min.
Advantageous effect of the present invention：
1st, microwave technology reaction speed will be accelerated tens of or even thousands of times, and can synthesize conventional method and be difficult to what is generated
Substance.
2nd, the present invention it is solvent-free, without existing for catalyst and condensing agent under the conditions of, directly with aliphatic acid, N- methyl ox sulphurs
Hydrochlorate is Material synthesis N- acyl-N-methyl taurates, and the reaction time is short, selectivity is good, high income, environmentally protective, simple
Efficiently.
3rd, the present invention optimizes the condition of microwave reaction, filters out suitable microwave reaction condition, the reaction time drop
As low as 10-60min, the production cycle is greatly shortened, and product must reach more than 90%.
4th, the present invention accelerates reaction process, and without the generation of by-product, product purity reaches by microwave radiation
More than 99%, properties of product are softer, small to skin injury.
Specific embodiment
It is further illustrated the present invention with reference to embodiment, but the scope of protection of present invention is not limited to implement
The range of example statement.
Embodiment 1
The lauric acid of 2.1g (10.5mmol) is weighed, the N methyl taurine sodium of 1.61g (10mmol) adds in microwave tube,
It is put into the micro-wave oven of 600W, 100 DEG C of reaction 60min after the completion of reaction, are cooled to 20 DEG C, add in 95% ethyl alcohol 5mL and beat
Slurry is filtered, then is washed with 95% ethyl alcohol of 3x3mL, dry, obtains N- lauroyls-N methyl taurine sodium 3.46g, is received
Rate 95.8%, product purity 99.1%.
Embodiment 2
The myristic acid of 3.43g (15mmol) is weighed, the N methyl taurine potassium of 1.78g (10mmol) adds in microwave tube, puts
In the micro-wave oven for entering 600W, 200 DEG C of reaction 20min after the completion of reaction, are cooled to 10 DEG C, add in 95% ethyl alcohol 10mL mashing,
It filters, then is washed with 95% ethyl alcohol of 3x5mL, it is dry, obtain N- cardamoms acyl group-N methyl taurine potassium 3.81g, yield
94%, product purity 99%.
Embodiment 3
The palmitic acid of 3.08g (12mmol) is weighed, the N methyl taurine ammonium of 1.56g (10mmol) adds in microwave tube, puts
In the micro-wave oven for entering 600W, 150 DEG C of reaction 35min after the completion of reaction, are cooled to 0 DEG C, add in 90% ethyl alcohol 10mL mashing,
It filters, then is washed with 90% ethyl alcohol of 3x5mL, it is dry, obtain N- palmityls-N methyl taurine potassium 3.96g, yield
96%, product purity 99.2%.
Embodiment 4
The coconut oil of 2.3g (11.5mmol) is weighed, the N methyl taurine sodium of 1.61g (10mmol) adds in microwave tube,
It being put into the micro-wave oven of 600W, 130 DEG C of reaction 45min after the completion of reaction, are cooled to 15 DEG C, add in absolute ethyl alcohol 10mL mashing,
It filters, then is washed with the absolute ethyl alcohol of 3x5mL, it is dry, obtain N- cocoyls-N methyl taurine potassium 3.36g, yield
93%, product purity 99.1%.
Embodiment 5
The N methyl taurine potassium of 17.73g (100mmol) is weighed, it is finely ground in agate mortar, then weigh 26g
The coconut oil of (130mmol) adds in microwave tube, is put into the micro-wave oven of 600W, and 180 DEG C are reacted 10min, cold after the completion of reaction
But to 5 DEG C, 95% ethyl alcohol 20mL mashing is added in, is filtered, then washed with 95% ethyl alcohol of 3x10mL, it is dry, obtain N- cocounut oil acyls
Base-N methyl taurine potassium 36.97g, yield 98%, product purity 99.6%.
The above embodiments are only the preferred technical solution of the present invention, and are not construed as the limitation for the present invention, this Shen
Please in embodiment and embodiment in feature in the absence of conflict, mutually can arbitrarily combine.The protection model of the present invention
The technical solution that should be recorded with claim is enclosed, the equivalent replacement side of technical characteristic in the technical solution recorded including claim
Case is protection domain.Equivalent replacement i.e. within this range is improved, also within protection scope of the present invention.
Claims (7)
- A kind of 1. method of applied microwave synthesis N- acyl-N-methyl taurates, it is characterised in that：The method synthesis path For：Wherein, M=sodium, potassium, ammonium；Include the following steps：1) using aliphatic acid, N methyl taurine salt as raw material, under solvent-free conditions, using microwave heating, N- acyls are directly synthesized Base-N methyl taurine salt；2) after reaction, to be cooled to 0-20 DEG C, the ethyl alcohol mashing of 90-100%, filtering, then the second with 90-100% are added in Alcohol washs, and is dried in vacuo to obtain sterling；The power of the step 1) microwave is 100-1000W, and the frequency of microwave is 2450MHz；Step 1) the reaction temperature is 100-200 DEG C, reaction time 10-60min.
- 2. according to the method described in claim 1, it is characterized in that：The object of the step 1) aliphatic acid and N methyl taurine salt The amount ratio of matter is 1.05-1.50.
- 3. according to the method described in claim 2, it is characterized in that：Step 1) the aliphatic acid is the aliphatic acid of C8-18.
- 4. according to the method described in claim 3, it is characterized in that：Step 1) the aliphatic acid is lauric acid, myristic acid, palm Acid or coconut oil.
- 5. according to the method described in claim 1, it is characterized in that：The power of the step 1) microwave be 300-600W, microwave Frequency be 2450MHz.
- 6. according to the method described in claim 1, it is characterized in that：Step 1) the reaction temperature is 120-180 DEG C, during reaction Between be 10-50min.
- 7. according to the method described in claim 6, it is characterized in that：Step 1) the reaction temperature is 150-180 DEG C, during reaction Between be 10-35min.
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Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP3692016A1 (en) | 2017-10-03 | 2020-08-12 | Unilever PLC | Method of enhanced conversion of taurine salts to alkyl taurate amides |
| WO2019206607A1 (en) | 2018-04-24 | 2019-10-31 | Unilever Plc | Enhanced conversion of taurine to alkyl taurate amide using phosphoric acid catalysts |
| CN110252395B (en) * | 2019-07-01 | 2020-10-16 | 湖北远大生命科学与技术有限责任公司 | Catalyst for preparing high-purity taurine and application thereof |
| JP2021038146A (en) * | 2019-08-30 | 2021-03-11 | マイクロ波化学株式会社 | Method for producing n-acylamine |
| KR102255540B1 (en) * | 2019-10-25 | 2021-05-25 | 한국화학연구원 | A Preparation method of Taurine surfactant derived from natural oil |
| CN111072524A (en) * | 2019-12-23 | 2020-04-28 | 张家港格瑞特化学有限公司 | Method for preparing fatty acyl amino acid surfactant by adopting high-temperature crystallization |
| CN114133344B (en) * | 2021-11-29 | 2024-03-22 | 江苏奥洁生物科技有限公司 | Method for preparing N-fatty acyl amino acid surfactant by high-temperature melting direct condensation |
| 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 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5496959A (en) * | 1994-05-23 | 1996-03-05 | Hoechst Celanese Corporation | Preparation of N-acyl taurates |
| CN1680305A (en) * | 2005-01-25 | 2005-10-12 | 上海奥利实业有限公司 | Synthesis of high-purity N-acyl-N-methyl sodium sulfate |
| US20120090983A1 (en) * | 2009-06-30 | 2012-04-19 | Clariant Finance (Bvi) Limited | Continuous Method For Acylating Amino Group-Carrying Organic Acids |
| CN102875422A (en) * | 2012-10-22 | 2013-01-16 | 湖北远大富驰医药化工股份有限公司 | New synthesis method of N-acyl-N-methyltaurine |
| US20150141682A1 (en) * | 2012-08-23 | 2015-05-21 | Galaxy Surfactants Ltd. | Method to Produce N-Acyl Amino Acid Surfactants Using N-Acyl Amino Acid Surfactants or the Corresponding Anhydrides as Catalysts |
| CN105175291A (en) * | 2015-09-09 | 2015-12-23 | 湖州新天字味精有限公司 | Synthesis method for lauroyl-sodium methyl taurate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009263508A (en) * | 2008-04-25 | 2009-11-12 | Sanyo Chem Ind Ltd | Detergent for electronic material and cleaning method |
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5496959A (en) * | 1994-05-23 | 1996-03-05 | Hoechst Celanese Corporation | Preparation of N-acyl taurates |
| CN1680305A (en) * | 2005-01-25 | 2005-10-12 | 上海奥利实业有限公司 | Synthesis of high-purity N-acyl-N-methyl sodium sulfate |
| US20120090983A1 (en) * | 2009-06-30 | 2012-04-19 | Clariant Finance (Bvi) Limited | Continuous Method For Acylating Amino Group-Carrying Organic Acids |
| US20150141682A1 (en) * | 2012-08-23 | 2015-05-21 | Galaxy Surfactants Ltd. | Method to Produce N-Acyl Amino Acid Surfactants Using N-Acyl Amino Acid Surfactants or the Corresponding Anhydrides as Catalysts |
| CN102875422A (en) * | 2012-10-22 | 2013-01-16 | 湖北远大富驰医药化工股份有限公司 | New synthesis method of N-acyl-N-methyltaurine |
| CN105175291A (en) * | 2015-09-09 | 2015-12-23 | 湖州新天字味精有限公司 | Synthesis method for lauroyl-sodium methyl taurate |
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