CN106518670A - Method for synthesizing butyrin - Google Patents
Method for synthesizing butyrin Download PDFInfo
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- CN106518670A CN106518670A CN201610830547.3A CN201610830547A CN106518670A CN 106518670 A CN106518670 A CN 106518670A CN 201610830547 A CN201610830547 A CN 201610830547A CN 106518670 A CN106518670 A CN 106518670A
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- Prior art keywords
- glycerol
- synthetic method
- butanoic acid
- filtrate
- glycerol monobutyralte
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- Fats And Perfumes (AREA)
Abstract
The invention provides a method for synthesizing butyrin. According to the method, butyric acid, glycerinum, a catalyst and a solid dehydrating agent are subjected to an esterification reaction under the heating condition, after the reaction is finished, filtration is conducted, a sodium hydroxide solution is dropwise added to the filtrate until the filtrate is neutral, then still standing and layering are conducted, the supernatant oil phase is taken to pass through an anhydrous sodium sulfate dry column, and the butyrin product is obtained. According to the method, it is avoided that an organic solvent serves as a water-carrying agent, the evaporation cost is decreased, the potential production safety hazard is reduced, pollution to the environment is avoided, and the synthesis technology is environmentally friendlier and safer; meanwhile, it is avoided that the organic solvent possibly remains in the product to cause potential safety hazard when the product is applied to feed-products; in addition, the esterification reaction is more efficient by the addition of the solid dehydrating agent, the reaction time is shortened and the reaction conversion ratio is increased.
Description
Technical field
The invention belongs to chemosynthesis technical field, and in particular to a kind of glycerol monobutyralte synthetic method.
Background technology
Butanoic acid monoglyceride is a kind of short-chain aliphatic ester, is butanoic acid and the product after glycerine esterification.By our examination
Test research to find, glycerol monobutyralte will not decompose release substantially in the gastric of animal body, and after entering intestinal, can be intestinal
Various lipases decompose and discharge butanoic acid.And it is well known that butanoic acid is used as a kind of short-chain fatty acid, can be directly intestinal
Epithelial cell provides energy, promotes the growth of intestinal villi and the development of intestinal, repairs impaired enterocyte, maintains intestinal to stick
Theca cell integrity.Additionally, butanoic acid can suppress the life of the sex pheromones such as Salmonella, escherichia coli, clostridium
It is long, increase the profitable strain quantity such as lactobacilluss；Antiinflammatory work can also be played by affecting the expression of LAM
With, it is also possible to by suppressing NF- κ B, preventing secretion of IL-8 etc. from reducing local inflammation；And medical research data shows butanoic acid
Glyceride is with the inhibitory action to enteritiies and good therapeutic effect.Thus glycerol monobutyralte can be beneficial to animal as one kind
The feed additive of intestinal is applied in animal cultivation, also occurs in that many corresponding products on market.
And the synthesis of glycerol monobutyralte at present, typically all with butanoic acid and glycerol as raw material, take off under the catalytic action of acid
Water is condensed to yield ester, and esterification belongs to a kind of reversible reaction, so in order to promote reaction to carry out to positive direction, reduce reaction
Time, the generation of side reaction is reduced, be generally required for adding water entrainer, to take away the moisture of generation in time, improve the speed of reaction
Rate and product yield.Conventionally used water entrainer has the organic solvents such as carbon tetrachloride, toluene, dimethylbenzene, hexamethylene, petroleum ether,
These organic solvents can be dissolved each other with ester, be difficult to remove totally completely, have a small amount of residual in follow-up distillation dedoping step
In products, if for certain hidden danger and threat will be formed in feed additive.In addition, organic solvent is used in a large number,
For the health of environmental conservation and operator similarly has threat, in still-process, partial solvent can be caused to leak into
Air, and still-process itself can also increase cost.Therefore, the increase of the application with glycerol monobutyralte in animal feed,
A kind of synthesis technique of more environmental protection of exploitation also becomes particularly significant and urgent thing.
The content of the invention
It is an object of the invention to provide one kind is under conditions of it need not add any organic solvent as water entrainer, utilize
Acid catalysiss butanoic acid carries out the method that esterification efficiently synthesizes glycerol monobutyralte with glycerol.
The technical scheme is that there is provided a kind of glycerol monobutyralte synthetic method, comprise the steps：
1) heating of butanoic acid, glycerol, catalyst and solid dehydrating agent is carried out into esterification in the reactor,.
2), after esterification terminates, the reacting liquid filtering in reactor is taken into filtrate, and to Deca sodium hydroxide in filtrate
Solution, is neutral to filtrate pH, and stratification takes upper oil phase.
3) oil phase is obtained final product into glycerol monobutyralte product by post being dried filled with anhydrous sodium sulfate.
Further, above-mentioned catalyst is strong phosphoric acid.
Further, above-mentioned butanoic acid is 1～3 with the ratio of the amount of the material of glycerol:1, catalyst charge is butanoic acid quality
4～5%, by the ratio for controlling butanoic acid and glycerol can obtain the butanoic acid monoglyceride of different content, two glycerol monobutyraltes and
Tributyrin product.
Further, above-mentioned solid dehydrating agent is sulfamic acid or boron oxide.
Further, above-mentioned sulfamic acid is 0.9～1.1 with the ratio of the amount of the material of butanoic acid:1, or boron oxide and butanoic acid
Material amount ratio be 0.3～0.4:1.
Further, above-mentioned steps 1) in esterification reaction temperature be 80～120 DEG C, the response time be 6～12h.
Further, above-mentioned steps 2) in sodium hydroxide solution mass concentration be 10%.
Compared with prior art, beneficial effects of the present invention：
(1) this glycerol monobutyralte synthetic method that the present invention is provided is avoided using organic solvent as water entrainer, reduces steaming
Cost is sent out, production safety hidden danger is reduced, it is to avoid the pollution to environment, synthesis technique more green safety；Also avoid simultaneously
In product may remaining organic solvent, cause which in being applied to feed product, to there is potential safety hazard.
(2) this glycerol monobutyralte synthetic method that the present invention is provided is by increasing solid dehydrating agent so that reaction rate
More efficiently, the response time is shortened, reaction conversion ratio is improve.
Specific embodiment
Below the technical scheme in the embodiment of the present invention is clearly and completely described, it is clear that described embodiment
Only a part of embodiment of the invention, rather than the embodiment of whole.Based on the embodiment in the present invention, the common skill in this area
All other embodiment that art personnel are obtained under the premise of creative work is not made, belongs to the model of present invention protection
Enclose.
Embodiment 1：
A kind of glycerol monobutyralte synthetic method is present embodiments provided, following steps are specifically included：
(1) butanoic acid 120g, glycerol 41.8g, and strong phosphoric acid 4.8g are put into in 500mL flasks, is warming up to 100 DEG C, and in batches
Solid dehydrating agent sulfamic acid 119g is added, 12h is reacted, esterification terminates.
(2) reacting liquid filtering after esterification is removed into solid matter therein, filtrate is proceeded in flask, unlatching is stirred
Mix, 10% sodium hydroxide solution of Deca, until reactant liquor pH is close to neutrality, be further continued for stirring 0.5h, then proceeded to a point liquid leakage
In bucket, stratification discards lower floor's water phase, takes upper oil phase.
(3) oil phase is obtained into tributyrin by the glass column of filling anhydrous sodium sulfate, yield is 96.17%,
Jing HPLC detect that its content is 95.24%.
Embodiment 2：
A kind of glycerol monobutyralte synthetic method is present embodiments provided, following steps are specifically included：
(1) butanoic acid 120g, glycerol 125.4g, and strong phosphoric acid 6g are put into in 500mL flasks, is warming up to 90 DEG C, and adds in batches
Enter solid dehydrating agent sulfamic acid 145.5g, react 6h, esterification terminates.
(2) reacting liquid filtering after esterification is removed into solid matter therein, filtrate is proceeded in flask, unlatching is stirred
Mix, 10% sodium hydroxide solution of Deca, until reactant liquor pH is close to neutrality, be further continued for stirring 0.5h, then proceeded to a point liquid leakage
In bucket, stratification discards lower floor's water phase, takes upper oil phase.
(3) oil phase is obtained into butanoic acid monoglyceride by the glass column of filling anhydrous sodium sulfate, yield is 89.32%,
Jing HPLC detect that its content is 90.06%.
Embodiment 3：
A kind of glycerol monobutyralte synthetic method is present embodiments provided, following steps are specifically included：
(1) butanoic acid 120g, glycerol 41.8g, and strong phosphoric acid 6g are put into in 500mL flasks, is warming up to 100 DEG C, and adds in batches
Enter solid dehydrating agent boron oxide 28.5g, react 12h, esterification terminates.
(2) reacting liquid filtering after esterification is removed into solid matter therein, filtrate is proceeded in flask, unlatching is stirred
Mix, 10% sodium hydroxide solution of Deca, until reactant liquor pH is close to neutrality, be further continued for stirring 0.5h, then proceeded to a point liquid leakage
In bucket, stratification discards lower floor's water phase, takes upper oil phase.
(3) oil phase is obtained into tributyrin by the glass column of filling anhydrous sodium sulfate, yield is 95.96%,
Jing HPLC detect that its content is 96.33%.
Embodiment 4：
A kind of glycerol monobutyralte synthetic method is present embodiments provided, following steps are specifically included：
(1) butanoic acid 120g, glycerol 125.4g, and strong phosphoric acid 4.8g are put into in 500mL flasks, is warming up to 90 DEG C, and in batches
Solid dehydrating agent boron oxide 38g is added, 10h is reacted, esterification terminates.
(2) reacting liquid filtering after esterification is removed into solid matter therein, filtrate is proceeded in flask, unlatching is stirred
Mix, 10% sodium hydroxide solution of Deca, until reactant liquor pH is close to neutrality, be further continued for stirring 0.5h, then proceeded to a point liquid leakage
In bucket, stratification discards lower floor's water phase, takes upper oil phase.
(3) oil phase is obtained into butanoic acid monoglyceride by the glass column of filling anhydrous sodium sulfate, yield is 92.65%,
Jing HPLC detect that its content is 91.83%.
Exemplified as above is only the illustration to the present invention, does not constitute the restriction to protection scope of the present invention, all
It is that design same or analogous with the present invention is belonged within protection scope of the present invention.
Claims (7)
1. a kind of glycerol monobutyralte synthetic method, it is characterised in that：Comprise the steps：
1) heating of butanoic acid, glycerol, catalyst and solid dehydrating agent is carried out into esterification in the reactor,；
2), after esterification terminates, the reacting liquid filtering in reactor is taken into filtrate, and to Deca sodium hydroxide solution in filtrate,
It is neutral to filtrate pH, stratification takes upper oil phase；
3) oil phase is obtained final product into glycerol monobutyralte product by post being dried filled with anhydrous sodium sulfate.
2. glycerol monobutyralte synthetic method as claimed in claim 1, it is characterised in that：The catalyst is strong phosphoric acid.
3. glycerol monobutyralte synthetic method as claimed in claim 2, it is characterised in that：The amount of the material of the butanoic acid and glycerol
Ratio be 1～3:1, catalyst charge for butanoic acid quality 4～5%.
4. glycerol monobutyralte synthetic method as claimed in claim 1, it is characterised in that：The solid dehydrating agent is sulfamic acid
Or boron oxide.
5. glycerol monobutyralte synthetic method as claimed in claim 4, it is characterised in that：The material of the sulfamic acid and butanoic acid
Amount ratio be 0.9～1.1:1, or the ratio of boron oxide and the amount of the material of butanoic acid is 0.3～0.4:1.
6. glycerol monobutyralte synthetic method as claimed in claim 1, it is characterised in that：The step 1) in esterification reaction temperature
For 80～120 DEG C, the response time is 6～12h.
7. glycerol monobutyralte synthetic method as claimed in claim 1, it is characterised in that：The step 2) in sodium hydroxide solution
Mass concentration be 10%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201610830547.3A CN106518670A (en) | 2016-09-19 | 2016-09-19 | Method for synthesizing butyrin |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610830547.3A CN106518670A (en) | 2016-09-19 | 2016-09-19 | Method for synthesizing butyrin |
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| CN106518670A true CN106518670A (en) | 2017-03-22 |
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| CN201610830547.3A Pending CN106518670A (en) | 2016-09-19 | 2016-09-19 | Method for synthesizing butyrin |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106946699A (en) * | 2017-05-09 | 2017-07-14 | 江苏瑞晨化学有限公司 | A kind of method of the catalyst preparation tributyrin of utilization polyvinyl chloride resin carried heteropoly acid |
| CN107954868A (en) * | 2017-12-01 | 2018-04-24 | 湖北神舟化工有限公司 | 1- glycerol monobutyraltes and preparation method thereof |
| CN110002998A (en) * | 2019-03-26 | 2019-07-12 | 张平 | A kind of esterifying reaction method and the application in preparation wintergreen and diethy-aceto oxalate |
Citations (2)
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|---|---|---|---|---|
| CN102090517A (en) * | 2010-12-21 | 2011-06-15 | 南昌大学 | Synthesis method of functional feed additive butyric acid mono-and di-glyceride |
| CN103012137A (en) * | 2013-01-11 | 2013-04-03 | 南京郁氏生物科技有限公司 | Preparation method of butyrin |
-
2016
- 2016-09-19 CN CN201610830547.3A patent/CN106518670A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102090517A (en) * | 2010-12-21 | 2011-06-15 | 南昌大学 | Synthesis method of functional feed additive butyric acid mono-and di-glyceride |
| CN103012137A (en) * | 2013-01-11 | 2013-04-03 | 南京郁氏生物科技有限公司 | Preparation method of butyrin |
Non-Patent Citations (3)
| Title |
|---|
| CHARLESG.CARLSON, ET AL.,: "The preparation of esters of formic acid using boron oxide", 《CAN.J.CHEM.》 * |
| 张竞清等: "氨基磺酸对酯化反应的催化作用", 《化学研究与应用》 * |
| 罗一呜等: "氨基磺酸催化合成乙酸异戊酯的研究", 《化学世界》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106946699A (en) * | 2017-05-09 | 2017-07-14 | 江苏瑞晨化学有限公司 | A kind of method of the catalyst preparation tributyrin of utilization polyvinyl chloride resin carried heteropoly acid |
| CN107954868A (en) * | 2017-12-01 | 2018-04-24 | 湖北神舟化工有限公司 | 1- glycerol monobutyraltes and preparation method thereof |
| CN110002998A (en) * | 2019-03-26 | 2019-07-12 | 张平 | A kind of esterifying reaction method and the application in preparation wintergreen and diethy-aceto oxalate |
| CN110002998B (en) * | 2019-03-26 | 2021-07-30 | 张平 | Esterification reaction method and application of esterification reaction method in preparation of wintergreen oil and diethyl oxalate |
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