CN1450046A - Method for synthesizing high-recovery and high-optical purity L-butyl lactate - Google Patents
Method for synthesizing high-recovery and high-optical purity L-butyl lactate Download PDFInfo
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- CN1450046A CN1450046A CN 02109429 CN02109429A CN1450046A CN 1450046 A CN1450046 A CN 1450046A CN 02109429 CN02109429 CN 02109429 CN 02109429 A CN02109429 A CN 02109429A CN 1450046 A CN1450046 A CN 1450046A
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- butyl lactate
- anhydrous sodium
- lactic acid
- vitriol oil
- solid anhydrous
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Abstract
The method for synthesizing L-butyl lactate with high yield and high optical purity uses concentrated sulfuric acid as catalyst, the added quantity of the concentrated sulfuric acid is 1.5% of lactic acid mass, the mole ratio of the n-butyl alcohol and lactic acid can be 0.5-4, reaction temp. is 50-150 deg.c, after the reaction is completed the solid anhydrous sodium acetate, solid anhydrous sodium carbonate, solid anhydrous sodium hydroxide or solid anhydrous sodium hydroxide can be directly added to neutralize sulfuric acid, then the above-mentioned material is filtered and separated so as to obtain the invented product. Its yield rate is up to above 90% and its optical purity is up to above 99.5%.
Description
Technical field
The invention relates to the synthetic method of L-n-Butyl lactate, refer in particular in the process of synthetic L-n-Butyl lactate and in the last handling process, reduce the loss of L-n-Butyl lactate, avoid racemization, improve the optical purity and the yield of L-n-Butyl lactate.
Background technology
N-Butyl lactate is the important alpha-hydroxy esters compounds of a class, it be a kind of do not have colour-stable, smell is gentle, be slightly soluble in the liquid of water.Be again a kind of excellent property, broad-spectrum high boiling solvent simultaneously, be mainly used in natural resin, synthetic resins, paint, printing-ink, dry-cleaning liquid, binding agent etc.It also is a kind of welcome edible synthetic perfume.Can be used in the food such as some soft drinks, ice river in Henan Province icepro.Particularly have optically active L-n-Butyl lactate and can be used for the intermediate of environment friendly agricultural.Present industrial synthesizing lactic acid butyl ester is many to be catalyzer with the vitriol oil, and by lactic acid and propyl carbinol direct esterification, reaction finishes the back and need handle through neutralization and washing for removing unnecessary sulfuric acid.Cause production process numerous and diverse, product loss is big, and produces a large amount of waste water.Along with environmental regulation to the improving constantly of environmental requirement, over past ten years, both at home and abroad extensive exploitation the catalyst for esterification reaction of a series of novel desirable thiosulfuric acids.As rare earth compound (summer golden red, the abundant rare earth compound of Liang Fu is synthetic to the catalysis of n-Butyl lactate, " Guangxi chemical industry " 1997,26 (1) 21-23), crystallization iron trichloride (Liu Lizhong, Yu Shanxin, Xiao Lixin etc., iron trichloride is synthetic to the catalysis of n-Butyl lactate, " chemical engineer " 1993, (5) 9-10), tosic acid (Lin Min, Qin Jingyun, Lin Jing, Synthesis of butyl lactatel, " Xiamen University's journal " 1997,36 (4) 581-584), (king deposits solid super-strong acid, Niu Youqin, Yu Shilong, solid super-strong acid T:O2/SO4-2 catalysis synthesizing lactic acid butyl ester, " chemistry world " 1993 (3): 311-313) etc.Though the intact back of these catalyst reactions only need be filtered, but production process simplified, but cost is than sulfuric acid height (the sulfuric acid price is 280 yuan/ton, and the tosic acid price is 2800 yuan/ton, and the iron trichloride price is 3500 yuan/ton).
Summary of the invention
The object of the present invention is to provide a kind of employing vitriol oil is catalyzer, handles the processing method of vitriolic operation but improved, thereby obtains the L-n-Butyl lactate of the synthetic high-optical-purity of high yield.
Technical scheme of the present invention is that the synthetic of L-n-Butyl lactate is to be catalyzer with the vitriol oil, the add-on of the vitriol oil is 1.5% (is benchmark with the lactic acid quality), the mol ratio of propyl carbinol and lactic acid can be 0.5-4, optimum mole ratio is 1.5-2, temperature of reaction is 50-150 ℃, and optimal reaction temperature is 80-120 ℃; Its principal character is directly to add solid water-free sodium-acetate, solid anhydrous sodium carbonate, solid water-free sodium bicarbonate or solid water-free sodium hydroxide, neutralisation of sulphuric acid after esterification finishes in reaction system; Filtering separation then, separating liquid can be directly used in distillation, preferably adds solid anhydrous sodium carbonate.
The above-mentioned vitriol oil and the mol ratio of solid anhydrous sodium carbonate are 1: 1.5-3, best 1: 1.5-2.
The present invention has abandoned traditional sodium carbonate solution neutralization, washing process, the generation of a large amount of waste water and the loss of n-Butyl lactate soluble in water have been avoided, even especially also make system be alkalescence a little easily by washing after the sodium carbonate solution neutralisation of sulphuric acid, in the still-process of the n-Butyl lactate of synthesis of optically active, easily make the n-Butyl lactate racemization.Improve the yield of back synthesizing lactic acid butyl ester and bring up to more than 90%, optical activity (e.e.%) also reaches more than 99.5%.
Embodiment
Example 1:
480g lactic acid, 348g benzene, 640g propyl carbinol and the adding of the 7.36g vitriol oil are equipped with in the 2000ml reaction flask of water trap and reflux condensing tube, and 80-100 ℃ was refluxed 17 hours, divided water 156ml.Reaction finishes the back and directly adds 11.93g solid anhydrous sodium carbonate neutralisation of sulphuric acid, and the mol ratio of the solid anhydrous sodium carbonate and the vitriol oil is 1.5: 1, filters then.The yield of L-n-Butyl lactate is 90%, and optical purity is 99.5%.
Example 2:
480g lactic acid, 348g benzene, 505g propyl carbinol and the adding of the 7.36g vitriol oil are equipped with in the 2000ml reaction flask of water trap and reflux condensing tube, and 80-100 ℃ was refluxed 17 hours, divided water 156ml.Reaction finishes the back and directly adds 14.32g solid anhydrous sodium carbonate neutralisation of sulphuric acid, and the mol ratio of the solid anhydrous sodium carbonate and the vitriol oil is 1.8: 1, filters then.The yield of L-n-Butyl lactate is 90%, and optical purity is 99.7%.
Example 3:
480g lactic acid, 348g benzene, 370g propyl carbinol and the adding of the 7.36g vitriol oil are equipped with in the 2000ml reaction flask of water trap and reflux condensing tube, and 80-100 ℃ was refluxed 17 hours, divided water 156ml.Reaction finishes the back and directly adds 15.91g solid anhydrous sodium carbonate neutralisation of sulphuric acid, and the mol ratio of the solid anhydrous sodium carbonate and the vitriol oil is 2: 1, filters then.The yield of L-n-Butyl lactate is 91%, and optical purity is 99.8%.
Example 4:
480g lactic acid, 348g benzene, 1010g propyl carbinol and the adding of the 7.36g vitriol oil are equipped with in the 2000ml reaction flask of water trap and reflux condensing tube, and 50-150 ℃ was refluxed 17 hours, divided water 156ml.Reaction finishes the back and directly adds 23.88g solid anhydrous sodium carbonate neutralisation of sulphuric acid, and the mol ratio of the solid anhydrous sodium carbonate and the vitriol oil is 3: 1, filters then.The yield of L-n-Butyl lactate is 91%, and optical purity is 99.8%.
Comparative example 1:
480g lactic acid, 348g benzene, 640g propyl carbinol and the adding of the 7.36g vitriol oil are equipped with in the 2000ml reaction flask of water trap and reflux condensing tube, and 80-120 ℃ was refluxed 17 hours, divided water 156ml.Reaction finishes the back with 600ml saturated acetic acid sodium solution neutralisation of sulphuric acid, washes secondary with the 1200ml saturated sodium-chloride then, uses anhydrous magnesium sulfate drying, filtration at last.The yield of L-n-Butyl lactate is 60%, and optical purity is 94%.
Comparative example 2:
480g lactic acid, 348g benzene, 640g propyl carbinol and the adding of the 7.36g vitriol oil are equipped with in the 2000ml reaction flask of water trap and reflux condensing tube, and 80-120 ℃ was refluxed 17 hours, divided water 156ml.Reaction finishes back 600ml saturated sodium carbonate solution neutralisation of sulphuric acid, and it is inferior to give a baby a bath on the third day after its birth with the 1200ml saturated sodium-chloride then, uses anhydrous magnesium sulfate drying, filtration at last.The yield of L-n-Butyl lactate is 56%, and optical purity is 90%.
Comparative example 3:
480g lactic acid, 348g benzene, 640g propyl carbinol and the adding of the 7.36g vitriol oil are equipped with in the 2000ml reaction flask of water trap and reflux condensing tube, and 80-120 ℃ was refluxed 17 hours, divided water 156ml.Reaction finishes the back with 600ml5% sodium hydroxide solution neutralisation of sulphuric acid, washes four times with the 2000ml saturated sodium-chloride then, uses anhydrous magnesium sulfate drying, filtration at last.The yield of L-n-Butyl lactate is 73%, and optical purity is 87%.
Claims (6)
1. the L-n-Butyl lactate synthetic method of a high yield, high-optical-purity, that is be catalyzer with the vitriol oil, lactic acid and propyl carbinol carry out esterification, it is characterized in that directly in reaction system, adding solid water-free sodium-acetate, solid anhydrous sodium carbonate, solid water-free sodium bicarbonate or solid water-free sodium hydroxide, neutralisation of sulphuric acid after esterification finishes; Filtering separation then.
2. L-n-Butyl lactate synthetic method as claimed in claim 1, the mol ratio that it is characterized in that the described vitriol oil and solid anhydrous sodium carbonate is 1: 1.5-3.
3. L-n-Butyl lactate synthetic method as claimed in claim 2, the mol ratio that it is characterized in that the described vitriol oil and solid anhydrous sodium carbonate is 1: 1.5-2.
4. L-n-Butyl lactate synthetic method as claimed in claim 1, the add-on that it is characterized in that the described vitriol oil is 1.5% of a lactic acid quality, and the mol ratio of propyl carbinol and lactic acid is 0.5-4, and temperature of reaction is 50-150 ℃.
5. L-n-Butyl lactate synthetic method as claimed in claim 4, the mol ratio that it is characterized in that described propyl carbinol and lactic acid is 1.5-2.
6. L-n-Butyl lactate synthetic method as claimed in claim 4 is characterized in that described temperature of reaction is 80-120 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021094292A CN1317255C (en) | 2002-04-05 | 2002-04-05 | Method for synthesizing high-recovery and high-optical purity L-butyl lactate |
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| CNB021094292A CN1317255C (en) | 2002-04-05 | 2002-04-05 | Method for synthesizing high-recovery and high-optical purity L-butyl lactate |
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| CN1450046A true CN1450046A (en) | 2003-10-22 |
| CN1317255C CN1317255C (en) | 2007-05-23 |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101914022A (en) * | 2010-08-23 | 2010-12-15 | 孝感市易生新材料有限公司 | Method for producing methyl lactate with high content and high optical purity in two steps |
| CN101914021A (en) * | 2010-08-23 | 2010-12-15 | 孝感市易生新材料有限公司 | Method for producing high-content and high-optical purity butyl lactate with two-step method |
| CN102659578A (en) * | 2012-04-28 | 2012-09-12 | 孝感市易生新材料有限公司 | Method for synthesizing lactate through microwave irradiation |
| WO2013159347A1 (en) | 2012-04-27 | 2013-10-31 | 孝感市易生新材料有限公司 | Method for continuously producing high-content high-optical-purity lactate |
| CN104876819A (en) * | 2015-05-14 | 2015-09-02 | 安徽中草香料有限公司 | Preparation method of isopropyl lactate |
| CN106187757A (en) * | 2016-07-13 | 2016-12-07 | 盐城华德（郸城）生物工程有限公司 | A kind of butyl lactate esterification technique |
| CN115073290A (en) * | 2022-06-24 | 2022-09-20 | 安徽华业香料股份有限公司 | Method for preparing butyl butyryl lactate with high yield without additional wastewater |
| CN115073280A (en) * | 2022-08-02 | 2022-09-20 | 马鞍山同杰良生物材料有限公司 | Method for recovering high-optical-purity lactic acid from polylactic acid synthetic substrate |
| CN115504958A (en) * | 2022-10-20 | 2022-12-23 | 山东寿光巨能金玉米开发有限公司 | Method for joint production of lactide and lactate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1076725C (en) * | 1999-09-09 | 2001-12-26 | 湖北省广水市民族化工有限公司 | Process for preparing sodium lactate |
-
2002
- 2002-04-05 CN CNB021094292A patent/CN1317255C/en not_active Expired - Fee Related
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101914022A (en) * | 2010-08-23 | 2010-12-15 | 孝感市易生新材料有限公司 | Method for producing methyl lactate with high content and high optical purity in two steps |
| CN101914021A (en) * | 2010-08-23 | 2010-12-15 | 孝感市易生新材料有限公司 | Method for producing high-content and high-optical purity butyl lactate with two-step method |
| CN101914021B (en) * | 2010-08-23 | 2013-06-05 | 孝感市易生新材料有限公司 | Method for producing high-content and high-optical purity butyl lactate with two-step method |
| CN101914022B (en) * | 2010-08-23 | 2013-08-21 | 孝感市易生新材料有限公司 | Method for producing methyl lactate with high content and high optical purity in two steps |
| WO2013159347A1 (en) | 2012-04-27 | 2013-10-31 | 孝感市易生新材料有限公司 | Method for continuously producing high-content high-optical-purity lactate |
| CN102659578A (en) * | 2012-04-28 | 2012-09-12 | 孝感市易生新材料有限公司 | Method for synthesizing lactate through microwave irradiation |
| CN104876819A (en) * | 2015-05-14 | 2015-09-02 | 安徽中草香料有限公司 | Preparation method of isopropyl lactate |
| CN106187757A (en) * | 2016-07-13 | 2016-12-07 | 盐城华德（郸城）生物工程有限公司 | A kind of butyl lactate esterification technique |
| CN115073290A (en) * | 2022-06-24 | 2022-09-20 | 安徽华业香料股份有限公司 | Method for preparing butyl butyryl lactate with high yield without additional wastewater |
| CN115073290B (en) * | 2022-06-24 | 2024-04-26 | 安徽华业香料股份有限公司 | Method for preparing butyl butyrylacetate without additional wastewater and with high yield |
| CN115073280A (en) * | 2022-08-02 | 2022-09-20 | 马鞍山同杰良生物材料有限公司 | Method for recovering high-optical-purity lactic acid from polylactic acid synthetic substrate |
| CN115504958A (en) * | 2022-10-20 | 2022-12-23 | 山东寿光巨能金玉米开发有限公司 | Method for joint production of lactide and lactate |
| CN115504958B (en) * | 2022-10-20 | 2023-12-19 | 山东寿光巨能金玉米开发有限公司 | Method for joint production of lactide and lactate |
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| CN1317255C (en) | 2007-05-23 |
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