CN107652180A - The production method of tributyrin - Google Patents
The production method of tributyrin Download PDFInfo
- Publication number
- CN107652180A CN107652180A CN201610583067.1A CN201610583067A CN107652180A CN 107652180 A CN107652180 A CN 107652180A CN 201610583067 A CN201610583067 A CN 201610583067A CN 107652180 A CN107652180 A CN 107652180A
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- Prior art keywords
- tributyrin
- butyric acid
- cut
- acid
- temperature
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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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a kind of production method of tributyrin, including：Using butyric acid and glycerine as raw material, high content tributyrin is produced by water entrainer of excessive butyric acid.Wherein, the butyric acid, the mol ratio of glycerine are（4~6）：1.Methods described also includes reactant mixture carrying out segmentation reaction distillation, further comprises and reaction product is washed or filtered, and the recycling of excessive butyric acid.Tributyrin yield is produced using this kind of method and reaches 95%, purity is up to more than 90%, and technological operation is simple and convenient, and cost is cheap, does not introduce other poisonous or dangerous raw material or solvent.
Description
Technical field
The present invention relates to the preparation of glyceryl ester, and in particular to a kind of preparation method of tributyrin.
Background technology
Butyric acid is the main energy sources of Colon mucosa cell, also has the effect for suppressing to kill harmful bacteria, is
Thing enteron aisle provides health environment, can improve animal ingestion product level etc..Tributyrin just starts point after entering animal intestinal tract
Solve as butyric acid and glycerine, be fully absorbed and utilize, provide energy source to greatest extent for animal, it will be apparent that practical function obtains
Accreditation, tributyrin are widely popularized and applied in recent years as a kind of feed addictive.In chemical industry synthesis, three fourths
Acid glyceride is often used as intermediate or solvent.In addition, tributyrin is as degradable green, high boiling plasticising
Agent draws attention.
The production method of traditional triglyceride, it is using carboxylic acid and glycerine as raw material, esterification is simultaneously with organic solvent
Band water, then removes the complete material of unreacted, yield 60% or so, composition includes single, double short and long-chain acyl triglyceride molecules, further can use again
Molecular distillation separates, and obtains more pure glyceryl ester.The method has that yield is low, post processing is cumbersome, equipment is expensive, water entrainer
The deficiencies of poisonous.Shen Jun equalitys are carried out under rudimentary sodium alkoxide or the catalysis of rudimentary potassium alcoholate using aliphatic acid low-carbon-ester and glycerine as raw material
Ester exchange, fatty acid triglyceride can be prepared, conjugated linoleic acid triglyceride content can be accomplished using molecular distillation
81.8%.（CN104479883A, the preparation method of fatty glyceride）.Equally exist high cost of material, equipment costliness and rear place
Manage the deficiencies of cumbersome.
Have at present some on tributyrin synthesis document and patent report, Zhou Zhigang etc. with butyl chloride and glycerine
Tributyrin, content 83.76% are prepared for for raw material.（CN104045556A.A kind of preparation side of tributyrin
Method）.The method use the very high butyl chloride of activity, cost is high, and security is poor, in addition, during to introduce chloroform etc. poisonous
Material, animal insecurity is undoubtedly added for for feed addictive.Yu Jiqiang leads to using butyric acid and glycerine as raw material
Enter nitrogen and carry out band water, synthesize target product only son's acid glyceride（CN 103012137A.Glycerol monobutyralte preparation method）, production
There is the tributyrin less than 22.6% in thing, be to occur as impure by-products, it is necessary to further study.
The content of the invention
The present invention seeks to overcome the deficiencies in the prior art, there is provided a kind of tributyrin production method, gained produce eventually
Thing purity is up to more than 90%, and more suitable for feed additive industry and intermediate building-up process, and reaction yield is up to 95%, former material
Material is cheap, safe operation.
To achieve the above object, the production method of the tributyrin designed by the present invention, comprises the following steps：With fourth
Acid and glycerine are raw material, while add catalyst, carry out esterification, while condensing reflux, intercept this section of cut, to be distillated
Temperature starts to warm up vacuum distillation when reaching 116~120 DEG C, stop when being distillated to no liquid, collects this section of cut, distills residue
As finished product crude product, residue filtering can will be distilled according to catalyst type, washing is further purified.
In the present invention, described cut processing method is：Leading portion cut reclaims butyric acid, the fourth of recovery by known method
Acid is used for lower batch of dispensing, and back segment cut is used for lower batch of dispensing directly as butyric acid.
Catalyst in the present invention selects p-methyl benzenesulfonic acid, sulfamic acid or niter cake, dosage for glycerine 3~
4%。
Excessive butyric acid of the present invention be for ensure generate tributyrin and ensure generation water taken away in time and
Increased butyric acid amount, it is from ratio：The mol ratio of butyric acid and glycerine is（4~7）：1.
Reaction distillation kettle control condition in the present invention is：Esterification reaction temperature is 130~160 DEG C, starts to warm up vacuum
The condition of distillation is that recovered (distilled) temperature reaches 116~120 DEG C, in distillation still reacting liquid temperature be not higher than 180 DEG C, vacuum for-
0.060~-0.090MPa, terminal are that there is no liquid outflow when 180 DEG C of reacting liquid temperature, vacuum are -0.090MPa.
Reactant does not stop to stir in course of reaction kettle in the present invention.
The removing method of catalyst of the present invention is washing or filtering, more specifically refers to p-methyl benzenesulfonic acid, amino sulphur
Acid residual can be removed with alkaline wash, and available filter off is crystallized after niter cake cooling and is removed.
To obtain the higher product of purity, the present invention is separated oil reservoir, preferably used using weak base water washing distillation residue
5~20% aqueous sodium carbonates.
Embodiment
Below by specific embodiment, the present invention will be described, but the invention is not limited in this.
Embodiment 1
Input n-butyric acie 900kg, recovery butyric acid 300kg, glycerine 300kg, p-methyl benzenesulfonic acid 12kg, stirring rise in reactor
Temperature, 150 DEG C of temperature in the kettle is kept, collects and distillates cut, when temperature to be distillated reaches 116~120 DEG C, change cut receiving tank,
Vacuum distillation is started to warm up, interior 160 DEG C of temperature, -0.085Mpa, is stopped when being distillated to no liquid, collects this section of cut, distills residue
As crude product, washed with 8% sodium carbonate liquor 850kg, it is finished product to separate oil reservoir, and liquid chromatographic detection tributyrin contains
Amount 78.12%, collects leading portion cut 300kg, reclaims out butyric acid 120kg, later stage cut 200kg, obtain product 900kg, yield
91.46%。
Embodiment 2
Input n-butyric acie 900kg, recovery butyric acid 600kg, glycerine 300kg, sulfamic acid 12kg, stirring heating, are protected in reactor
150 DEG C of temperature in the kettle is held, collects and distillates cut, when temperature to be distillated reaches 116~120 DEG C, cut receiving tank is changed, starts to rise
Temperature vacuum distillation, interior 160 DEG C of temperature, -0.085Mpa, stops when no liquid distillates, and collects this section of cut, and distillation residue is as thick
Product, washed with 10% sodium carbonate liquor 680kg, it is finished product to separate oil reservoir, liquid chromatographic detection tributyrin content
90.18%, leading portion cut 350kg is collected, butyric acid 160kg is reclaimed out, later stage cut 420kg, obtains product 930kg, yield
94.46%。
Embodiment 3
Input n-butyric acie 900kg, recovery butyric acid 900kg, glycerine 300kg, niter cake 12kg, stirring heating, are protected in reactor
150 DEG C of temperature in the kettle is held, collects and distillates cut, when temperature to be distillated reaches 116~120 DEG C, cut receiving tank is changed, starts to rise
Temperature vacuum distillation, interior 160 DEG C of temperature, -0.075Mpa, stops when no liquid distillates, and collects this section of cut, and distillation residue is as thick
Product, cooled and filtered, mother liquor are washed with 8% sodium carbonate liquor 750kg, and it is finished product to separate oil reservoir, the butyric acid of liquid chromatographic detection three
Glyceride content 93.12%, leading portion cut 400kg is collected, reclaim out butyric acid 210kg, later stage cut 670kg, obtain product
950kg, yield 96.49%.
Claims (10)
1. a kind of production method of tributyrin, this method comprise the following steps：
Step carries out esterification 1. using butyric acid and glycerine as raw material, while add catalyst under normal pressure, carry out esterification
While, condensing reflux, this section of cut is intercepted, the temperature of reaction is 130~160 DEG C, and the reaction time is 1~4h；The butyric acid
Reaction mol ratio with glycerine is：（4~7）：1, catalyst amount is the 3~4% of glycerine；
Step starts to warm up vacuum distillation when 2. temperature to be distillated reaches 116~120 DEG C, stop when being distillated to no liquid, collects this
Section cut, reacting liquid temperature is no more than 180 DEG C in distillation still, and the vacuum of vacuum distillation is -0.060~-0.090MPa；
3. it is finished product that step distills residue, can will distill residue filtering according to catalyst type, washing is carried out further
Purifying；
4. step 1 cut reclaims butyric acid to step by known method, and step 2 cut is used for dispensing directly as butyric acid.
2. a kind of production method of tributyrin according to claim 1, it is characterised in that catalyst is selected, to methyl
Benzene sulfonic acid, sulfamic acid or niter cake.
A kind of 3. production method of tributyrin according to claim 1, it is characterised in that the excessive butyric acid be for
Ensure that generate tributyrin and the water of generation is taken away and increased butyric acid amount in time.
4. according to a kind of production method of tributyrin of claim 1,4,5, it is characterised in that the butyric acid and sweet
Oil mol ratio be（4~7）：1.
A kind of 5. production method of tributyrin according to claim 1, it is characterised in that the esterification reaction temperature
For 130~160 DEG C of.
6. a kind of preparation method of tributyrin according to claim 1, it is characterised in that described to start to warm up vacuum
The condition of distillation is that recovered (distilled) temperature reaches 116~120 DEG C.
A kind of 7. preparation method of tributyrin according to claim 1, it is characterised in that the step 1 cut recovery
Butyric acid and step 2 cut be all used for dispensing.
A kind of 8. preparation method of tributyrin according to claim 1, it is characterised in that the step 2. distillation still
Interior reacting liquid temperature is less than 180 DEG C, and vacuum is -0.060~-0.090MPa.
9. according to the method described in claim 1,2, it is characterised in that the removing method of the catalyst is washing or filters, more
Specifically refer to p-methyl benzenesulfonic acid, sulfamic acid residual can be removed with alkaline wash, available filter off of niter cake is removed.
10. a kind of preparation method of tributyrin according to claim 1, it is characterised in that described be further purified be
Refer to using weak base water washing distillation residue, oil reservoir is separated, preferably using 5~20% aqueous sodium carbonates.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610583067.1A CN107652180A (en) | 2016-07-23 | 2016-07-23 | The production method of tributyrin |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610583067.1A CN107652180A (en) | 2016-07-23 | 2016-07-23 | The production method of tributyrin |
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| CN107652180A true CN107652180A (en) | 2018-02-02 |
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| CN201610583067.1A Withdrawn CN107652180A (en) | 2016-07-23 | 2016-07-23 | The production method of tributyrin |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107673970A (en) * | 2017-11-01 | 2018-02-09 | 泸天化（集团）有限责任公司 | A kind of preparation method of tributyrin |
| CN112299993A (en) * | 2020-10-30 | 2021-02-02 | 河北金谷再生资源开发有限公司 | Device and method for producing tributyrin |
| CN112321423A (en) * | 2020-12-11 | 2021-02-05 | 河南智盛优品生物科技有限公司 | Synthesis process of tributyrin |
| CN114456066A (en) * | 2022-01-29 | 2022-05-10 | 山东成武易信环保科技有限公司 | Distillation method for purifying glycerol monobutyrate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1604950A (en) * | 2001-12-20 | 2005-04-06 | 费罗公司 | Glycerin triester plasticizer |
-
2016
- 2016-07-23 CN CN201610583067.1A patent/CN107652180A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1604950A (en) * | 2001-12-20 | 2005-04-06 | 费罗公司 | Glycerin triester plasticizer |
Non-Patent Citations (3)
| Title |
|---|
| OSCAR YESID SUAREZ PALACIOS，ET AL.: "Low-Molecular-Weight Glycerol Esters as Plasticizers for Poly(vinyl chloride)", 《JOURNAL OF VINYL & ADDITIVE TECHNOLOGY》 * |
| 李楠，张曙生主编: "《基础有机化学实验》", 28 February 2002 * |
| 毛尚良: "丁酸戊酯的制备", 《化学试剂》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107673970A (en) * | 2017-11-01 | 2018-02-09 | 泸天化（集团）有限责任公司 | A kind of preparation method of tributyrin |
| CN112299993A (en) * | 2020-10-30 | 2021-02-02 | 河北金谷再生资源开发有限公司 | Device and method for producing tributyrin |
| CN112299993B (en) * | 2020-10-30 | 2023-06-16 | 河北金谷再生资源开发有限公司 | Device and method for producing tributyrin |
| CN112321423A (en) * | 2020-12-11 | 2021-02-05 | 河南智盛优品生物科技有限公司 | Synthesis process of tributyrin |
| CN114456066A (en) * | 2022-01-29 | 2022-05-10 | 山东成武易信环保科技有限公司 | Distillation method for purifying glycerol monobutyrate |
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Application publication date: 20180202 |
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