CN101538215A - Method for preparing gamma-butyrobetaine ester - Google Patents
Method for preparing gamma-butyrobetaine ester Download PDFInfo
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- CN101538215A CN101538215A CN200910014910A CN200910014910A CN101538215A CN 101538215 A CN101538215 A CN 101538215A CN 200910014910 A CN200910014910 A CN 200910014910A CN 200910014910 A CN200910014910 A CN 200910014910A CN 101538215 A CN101538215 A CN 101538215A
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- ester
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- butyrobetaine
- alcohol
- trimethylamine
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Abstract
The invention discloses a method for preparing gamma-butyrobetaine ester, which uses gamma-chloro butyric ester and trimethylamine as raw materials and alcohol as a solvent. The raw materials and the solvent are heated to react in a high-pressure autoclave, and products of the gamma-butyrobetaine ester are obtained by concentrating processing and fine purification. The gamma-butyrobetaine ester is methyl ester or ethyl ester. The feeding mol ratio of the gamma- chloro butyric ester to the trimethylamine is 1:1.2-3.0, wherein the degree of purity of the gamma-chloro butyric ester is not less than 97 percent, and the degree of purity of the trimethylamine is more than 98 percent. The alcohol as the solvent is one of methanol, absolute ethyl alcohol, propanol, or isopropanol, and the use level of the alcohol is 1-5 times higher than that of the gamma-chloro butyric ester. The reaction is carried out at the temperature of 50-120 DEG C and the high pressure for 5-24h in an airtight mode. Because the technical scheme is adopted, the preparing cost is decreased, the domestic blank for preparing the gamma-butyrobetaine ester is replenished, and the mol yield of the products is enhanced and can reach more than 90 percent.
Description
Technical field
The present invention relates to a kind of production method of butyrobetaine derivative, relate in particular to a kind of production method of butyrobetaine ester.
Background technology
The gamma-butyrobetaine ester belongs to the derivative of butyrobetaine, at medicine and fields such as health, detergents and cosmetic many purposes is arranged.External synthetic gamma-butyrobetaine ester method approximately needs 3h for γ-bromo ethyl butyrate is fed pure product Trimethylamine 99 gas in acetone solvent, the consumption of Trimethylamine 99 is 2 times of γ-bromo butyric ester mole number, airtight reaction overnight under room temperature again, the yield of product is about 85%.
Synthetic needs as γ-bromo ethyl butyrate are used bromine as raw material, so price is higher, have increased the synthetic cost of gamma-butyrobetaine ester virtually.
Summary of the invention
Technical problem to be solved by this invention provides a kind of method of comparatively cheap, that yield is high production gamma-butyrobetaine ester.
For solving the problems of the technologies described above, technical scheme of the present invention is: present method is to be raw material, to be solvent with alcohol that with γ-chloro butyric ester and Trimethylamine 99 the mode of reacting by heating is produced the gamma-butyrobetaine ester in reactor.
Described gamma-butyrobetaine ester is methyl esters or ethyl ester; The molar ratio of γ-chloro butyric ester and Trimethylamine 99 is 1: 1.2～3.0, γ-chloro butyric ester purity 〉=97% wherein, Trimethylamine 99 purity＞98%; Solvent alcohol is a kind of in methyl alcohol, dehydrated alcohol, propyl alcohol or the Virahol, and consumption is 1～5 times of γ-chloro butyric ester quality.
Described reaction is under 50～120 ℃ of temperature, preferred 70～100 ℃ of confined reaction 5～24h, preferred 8～12h.
Reacted after concentrate and the concentration method by the organic solvent recrystallization obtains gamma-butyrobetaine ester product, or made with extra care after the reconcentration and obtain gamma-butyrobetaine ester elaboration.
Described recrystallization solvent is alcohols, ketone or ester class, as methyl alcohol, ethanol, Virahol, acetone or ethyl acetate, and preferred acetone or ethyl acetate; It is described that refining to select solvent for use be methyl alcohol, ethanol, Virahol, acetone or ethyl acetate.
Owing to adopted technique scheme, reduced production cost, filled up the blank of domestic production gamma-butyrobetaine ester, the molar yield that has improved product can reach more than 90%.
Embodiment
Below in conjunction with embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in and limit the scope of the invention.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Embodiment 1: add 136.6g γ-chloro methyl-butyrate (1.0mol, 99%), 89g Trimethylamine 99 (1.5mol), 180g methyl alcohol in the 1L autoclave, airtight back is stirred and is heated up 85 ℃ insulation reaction 10h.Reaction finishes and reduces to room temperature, discharging.Steam and remove excessive Trimethylamine 99, cool to 0～5 ℃ and separate out, filter and obtain white crystals, wash with small amount of acetone.Product is in 60 ℃ of following vacuum-drying 5h, finished product 166g, HPLC content 99.2%, yield 85%.
Embodiment 2: add 150.6g γ-chloro ethyl butyrate (1.0mol, 99%), 89g Trimethylamine 99 (1.5mol), 180g dehydrated alcohol in the 1L autoclave, airtight back is stirred and is heated up 85 ℃ insulation reaction 10h.Reaction finishes and reduces to room temperature, discharging.Steam and remove excessive Trimethylamine 99, cool to 0～5 ℃ and separate out, filter and obtain white crystals, wash with small amount of acetone.Product is in 70 ℃ of following vacuum-drying 5h, finished product 191g, HPLC content 99.5%, yield 91%.
Embodiment 3: add 136.6g γ-chloro methyl-butyrate (1.0mol, 99%), 118g Trimethylamine 99 (2.0mol, 99%), 180g methyl alcohol in the 1L autoclave, airtight back is stirred and is heated up 85 ℃ insulation reaction 10h.Reaction finishes and reduces to room temperature, discharging.Steam and remove excessive Trimethylamine 99, cool to 0～5 ℃ and separate out, filter and obtain white crystals, wash with small amount of acetone.Product obtains finished product 170g in 60 ℃ of following vacuum-drying 5h, HPLC content 99.3%, yield 87%.
Embodiment 4: add 136.6g γ-chloro methyl-butyrate (1.0mol, 99%), 71g Trimethylamine 99 (1.2mol, 99%), 180g methyl alcohol in the 1L autoclave, the 80 ℃ of insulation reaction 24h that heat up are stirred in airtight back.Reaction finishes and reduces to room temperature, discharging.Steam and remove excessive Trimethylamine 99, cool to 0～5 ℃ and separate out, filter and obtain white crystals, wash with small amount of acetone.Product obtains finished product 163g in 60 ℃ of following vacuum-drying 5h, HPLC content 99.5%, yield 83.3%.
Embodiment 5: add 150.6g γ-chloro ethyl butyrate (1.0mol, 99%), 71g Trimethylamine 99 (1.2mol, 99%), 180g dehydrated alcohol in the 1L autoclave, airtight back is stirred and is heated up 85 ℃ insulation reaction 10h.Reaction finishes and reduces to room temperature, discharging.Steam and remove excessive Trimethylamine 99, cool to 0～5 ℃ and separate out, filter and obtain white crystals, wash with small amount of acetone.Product obtains finished product 187g in 70 ℃ of following vacuum-drying 5h, HPLC content 99.5%, yield 89.2%.
Embodiment 6: add 150.6g γ-chloro ethyl butyrate (1.0mol, 99%), 118g Trimethylamine 99 (2.0mol, 99%), 180g dehydrated alcohol in the 1L autoclave, airtight back is stirred and is heated up 85 ℃ insulation reaction 10h.Reaction finishes and reduces to room temperature, discharging.Steam and remove excessive Trimethylamine 99, cool to 0～5 ℃ and separate out, filter and obtain white crystals, wash with small amount of acetone.Product obtains finished product 195g in 70 ℃ of following vacuum-drying 5h, HPLC content 99.5%, yield 93.0%.
Claims (6)
1. produce the method for gamma-butyrobetaine ester, it is characterized in that: described method is to be raw material, to be solvent with alcohol that with γ-chloro butyric ester and Trimethylamine 99 the mode of reacting by heating is produced the gamma-butyrobetaine ester in autoclave.
2. the method for production gamma-butyrobetaine ester as claimed in claim 1 is characterized in that: described reaction is to react 5～24h under 50～120 ℃ of temperature.
3. the method for production gamma-butyrobetaine ester as claimed in claim 1 is characterized in that: the molar ratio of described γ-chloro butyric ester and Trimethylamine 99 is 1: 1.2～3.0; The solvent alcohol consumption is 1～5 times of γ-chloro butyric ester quality.
4. the method for production gamma-butyrobetaine ester as claimed in claim 1 is characterized in that: described gamma-butyrobetaine ester is methyl esters or ethyl ester; Solvent alcohol is a kind of in methyl alcohol, dehydrated alcohol, propyl alcohol or the Virahol.
5. as the method for each described production gamma-butyrobetaine ester of claim 1 to 4, it is characterized in that: reacted after concentrate and the concentration method by the organic solvent recrystallization obtains gamma-butyrobetaine ester product.
6. the method for production gamma-butyrobetaine ester as claimed in claim 5 is characterized in that: described recrystallization solvent is alcohols, ketone or ester class, as methyl alcohol, ethanol, Virahol, acetone or ethyl acetate, and preferred acetone or ethyl acetate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910014910A CN101538215A (en) | 2009-04-24 | 2009-04-24 | Method for preparing gamma-butyrobetaine ester |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910014910A CN101538215A (en) | 2009-04-24 | 2009-04-24 | Method for preparing gamma-butyrobetaine ester |
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| CN101538215A true CN101538215A (en) | 2009-09-23 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107879944A (en) * | 2017-10-30 | 2018-04-06 | 杭州海尔希畜牧科技有限公司 | A kind of method for preparing butyrobetaine |
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2009
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107879944A (en) * | 2017-10-30 | 2018-04-06 | 杭州海尔希畜牧科技有限公司 | A kind of method for preparing butyrobetaine |
| CN107879944B (en) * | 2017-10-30 | 2020-05-22 | 杭州海尔希畜牧科技有限公司 | Method for preparing butyl betaine |
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Application publication date: 20090923 |