CN107373094A - A kind of synthesis of tributyrin and the application in feed - Google Patents
A kind of synthesis of tributyrin and the application in feed Download PDFInfo
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- CN107373094A CN107373094A CN201710572760.3A CN201710572760A CN107373094A CN 107373094 A CN107373094 A CN 107373094A CN 201710572760 A CN201710572760 A CN 201710572760A CN 107373094 A CN107373094 A CN 107373094A
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
Abstract
A kind of synthetic method of tributyrin and the application in feed.Butyric acid and glycerine high temperature in the presence of solvent-free are directly synthesized tributyrin by described synthetic method using liquid catalyst, tributyrin is separated with unreacted raw material by rectifying column with the method for high vacuum distillation again, cut corresponding to collection is tributyrin, and content is 98%（w/w）The reuse after with high performance liquid chromatography detection content of above distillation.Described application refers to the tributyrin of present invention process production, for preparing the feed addictive for promoting economic animal growth and improving feed conversion rate, actual interpolation amount is 100 2000ppm, and addition can be reduced relative to the tributyrin of other technique productions on the market.
Description
Technical field
The invention belongs to field of feed additive technology, preparation more particularly to tributyrin and its in economy
Application in terms of animal feeding.
Background technology
Tributyrin（glyceryl tributyrate）It is that chemical formula is C15H26O6Short-chain aliphatic ester, CAS
Number：60-01-5, molecular weight：302.36, also known as glycerin tributyrate, the nearly oily liquids of white.Almost odorlessness, slightly fat
Fragrance.It is soluble in ethanol, chloroform and ether, it is extremely difficult to be dissolved in water (0.010%).Natural product are present in tallow.
Tributyl glyceride does not decompose in gastric juice, is slowly discharged into butyric acid and glycerine in the presence of intestines lipase.Fourth
Acid is a kind of short chain fatty acids, is intestinal epithelial cell primary energy source, can significantly stimulate Intestinal epitheliual cell proliferation, increases small intestine
Height of naps, so promote Nutrient Absorption, strengthen immunity, improve animal health, so as to overcome stress of baby pigs caused ablaction syndrome,
Improve production performance and reduce the death rate.
Usual tributyrin need to be obtained by butyl chloride and glycerine reaction（CN104045556A）, due to the spy of acyl chlorides
Property, corrosivity is strong, it is not easy to which shipping storage, running into air is easy for producing acid mist, and property is extremely unstable, so in production exercise
More difficult use in work.
Butyl chloride is with after glycerine reaction, producing a large amount of hydrochloric acid, it is difficult to is injured using and to equipment larger.
Although butyl chloride activity is higher, prepared tributyrin content is difficult in patent CN104045556A
Reach 90%（w/w）More than
, it is necessary to use water or soda lye wash product after traditional course of reaction, unnecessary hydrochloric acid and butyric acid are removed, can be produced more
Waste water, due to butyric acid odor-sensitive, caused waste water is more intractable.
Patent CN105801413A refer to reclaim butyric acid with the mode of distillation, but due to being urged using superpower solid acid
Agent, during need logical nitrogen protection, and rectifying column and vacuum distillation is used, it is larger that relative boiling point gap can only be reclaimed
Butyric acid, and super acids price is higher, and it is more difficult to preserve use.
Because the tributyrin content produced with existing process is not high, impurity is more, and the butyric acid of residual has larger
Smell, influence animal food calling, and the catalyst that part remains easily causes digestive tract reaction, therefore have patent
（CN03128368）Iing is proposed its addition in feed needs to reach that 5000-10000ppm is just effective, and this, which is undoubtedly added, adds
Addition sheet.
The content of the invention
For some shortcomings of prior art production method, the invention provides a kind of new synthetic method, can obtain
The tributyrin product of content more than 98%, it can be used for preparing the growth of promotion economic animal and improve feed conversion rate
Feed addictive, actual interpolation amount are 100-2000ppm, can relative to the tributyrin of other technique productions on the market
Reduce addition.
It is as follows that the present invention solves the technical scheme that its technical problem uses：
A kind of synthetic method of tributyrin, described synthetic method using liquid catalyst by butyric acid with glycerine without molten
High temperature directly synthesizes tributyrin in the presence of agent, and the wherein raw material mass ratio that feeds intake is：Butyric acid：Glycerine：Catalyst=5-10：
1：0.05-0.1, reaction temperature are 150-160 DEG C；Again with vacuum distillation method using rectifying column by tributyrin with not
The raw material separation of reaction, cut corresponding to collection is tributyrin, and content is 98%（w/w）More than；Distillation is with height
Reuse after effect liquid phase chromatogram detection level.Preferably, described liquid catalyst is oleum, and content is calculated as 110% with sulfuric acid
（w/w）.
Preferably, for the vacuum of the vacuum distillation in more than 100pa, the filler of rectifying column is ceramics or glass.
The application for the tributyrin that the inventive method is prepared, promote economic animal growth and raising for preparing
The feed addictive of feed conversion rate, actual interpolation amount are 100-2000ppm.
Preferably, described application process is that directly this product is added in the feed of economic animal according to addition, or
By this product and bearer configuration into pre-mixing agent, or fed after being mixed into premix, concentrate feed with other feed addictives or feedstuff
Food.
Preferably, described economic animal includes the aquatic products of chicken, duck, goose, quail, pig, ox, sheep, horse or artificial feeding
Animal.
Using the common catalyst being easy to get and vacuum distillation, it can avoid protecting using nitrogen, make production operation simpler
It is single；All raw materials can be put into reaction, and yield can reach 100% in theory；Product need not wash, and greatly reduce
The discharge of waste water and waste gas, meet the developing direction of China Search green chemistry.
Beneficial effects of the present invention：The tributyrin that this method is prepared, shows through zoopery, can be significantly
Addition is reduced, addition 100ppm was both effective in feed, had maximum economic valency when addition reaches 500-1000ppm
It is worth, the addition mentioned in other patents（CN03128368）Need to reach more than 5000ppm, the product that this method obtains has 5-
10 times of effect, addition cost being greatly reduced, its main cause is that the product purity of this method is high, alimentary canal is stimulated less,
Animal is liked eating, and increases feed feed intake, and product is fully able to play its effect according to Biological Principles.
The preparation-obtained tributyrin of the present invention can be not only used for piglet, and it is dynamic to can be used for other economy
The domestic animals such as the thing such as birds such as chicken and duck goose, pig sheep ox rabbit.
Specific embodiment：
In following examples, used chemical raw material is purchased from Chinese medicines group.Finished product detection just detects skill by Zhejiang state
Art Co., Ltd is detected.
Embodiment 1：The synthesis of tributyrin
In the 1000ml there-necked flasks equipped with stirring and with water installations, 92g glycerine, 440g butyric acid, the 9.8g concentrated sulfuric acids, stirring are put into
150 DEG C are warming up to, is incubated, and caused water, 5 hours reaction time are gone using band water installations point.Reaction terminates, will be with water installations
Change the rectifying column filled with ceramics into, keep vacuum 70-100pa, the cut for collecting 170-175 DEG C is three butyric acid glycerine
Ester, total amount 298g, it is 99.1% through gas chromatographic analysis content, total yield 97.78%.Front-end volatiles and substrate are collected into rear enclosure to use
In being produced to next group.
Embodiment 2：The synthesis of tributyrin
In the 1000ml there-necked flasks equipped with stirring and with water installations, 92g glycerine, 440g butyric acid, the 5g concentrated sulfuric acids, stirring liter are put into
Temperature is to 160 DEG C, insulation, and goes caused water, 3 hours reaction time using band water installations point.Reaction terminates, and will be changed with water installations
Into the rectifying column filled with glass, vacuum 70-100pa is kept, the cut for collecting 170-175 DEG C is tributyrin,
Total amount 295g, it is 99.0% through gas chromatographic analysis content, total yield 96.7%.Front-end volatiles and substrate are collected into rear enclosure to use down
In a collection of production.
Embodiment 3：The tributyrin that this patent method obtains and other like products contrast experiment（Piglet）
The tributyrin and conventional antibiotic Nosiheptide obtained using this patent is used as trial drug.Selection nest is other, parity
The DLY piglet of close 7 nests health, per about 20, nest column pig, the kg of average weight about 11.It is divided into 5 by Random Design principle
Individual treatment group and 2 control groups, every group of 2 columns.Tributyrin addO-on therapy is：50 mg, 100 are added per kilogram of feed
Mg, 500 mg, 1000 mg, 2000mg tributyrins.Positive controls add 5 mg/kg Nosiheptides using basal diet.
Blank control group does not add any medicine using basal diet.
Experiment piglet uses subfield group feeding, free choice feeding and drinking-water, carries out conventional piglet immunological program, feeding management is by normal
Rule are carried out, and pig house is routinely carried out disinfection before experiment, weighed after the d of preliminary trial period 5, positive to try the d of the phase 35.Pig is observed during experiment daily
Mine massively food situation, health status.After off-test, prohibit 24 h of feeding and weigh, calculate average daily gain (ADFI), average daily gain
And feed-weight ratio (F/G), survival rate and diarrhea rate (ADG).And significance difference analysis is carried out to result, analysis result is shown in Table 1 He
Table 2.
Influence of the tributyrin of table 1 to weaned piglets
| Group | Starting weight/kg | End weight/kg | Daily gain/g | Daily ingestion amount/g | Feed-weight ratio |
| Blank control group | 11.49±0.21 | 25.00±1.25a | 385.95±30.52a | 841.84±40.13b | 2.16± 0.35b |
| Positive drug group | 11.59±0.27 | 26.79±1.33b | 434.75±35.41c | 821.66±39.07b | 1.89± 0.56a |
| 50mg/kg | 11.49±0.31 | 25.89±1.42a | 404.25±33.25b | 853.65±36.23c | 2.08± 0.63b |
| 100mg/kg | 11.57±0.17 | 26.25±1.03b | 423.71±30.13c | 786.15±32.16a | 1.74± 0.47a |
| 500mg/kg | 11.61±0.13 | 27.62±1.01c | 457.66±29.96d | 823.21±20.47b | 1.80± 0.31a |
| 1000mg/kg | 11.53±0.24 | 27.64±1.34c | 460.43±40.32d | 851.71±40.36c | 1.85± 0.67a |
| 2000mg/kg | 11.56±0.21 | 27.30±0.75c | 449.85±16.91c | 861.71±26.11c | 1.87± 0.19b |
a,b,c,d:In same row different internal standards represent significant difference (P<0.05)。
Result of the test shows：Compared with blank control group, three butyric acid that 100-2000mg/kg dosage is added in feed are sweet
Grease, piglet can be promoted to increase weight, reduce feedstuff-meat ratio.Compared with Nosiheptide group, three butyric acid of 50mg/kg and 100mg/kg dosage
The feeding effect of glyceride is slightly worse, and the piglet daily gain of the butyric acid glycerine groups of 500mg/kg tri- is relatively averaged day compared with positive controls
Weightening is suitable, and the piglet daily gain of the butyric acid glycerine group of 1000mg/kg, 2000mg/kg tri- is relatively averaged day compared with positive controls
Weightening dramatically increase (P<0.05), feed-weight ratio decreases, and difference is not notable.
Influence of the tributyrin of table 2 to piglet survival ratio and Scours index
| Group | Survive number | Survival rate（%） | Head of suffering from diarrhoea is secondary | Diarrhea rate（%） |
| Blank control group | 38 | 95a | 25 | 1.78c |
| Positive controls | 40 | 100b | 14 | 1.00b |
| 50mg/kg | 38 | 95a | 24 | 1.71c |
| 100mg/kg | 40 | 100b | 17 | 1.21b |
| 500mg/kg | 40 | 100b | 10 | 0.71a |
| 1000mg/kg | 40 | 100b | 11 | 0.80a |
| 2000mg/kg | 40 | 100b | 12 | 0.88a |
a,b,c:In same column different internal standards represent significant difference (P<0.05)。
Result of the test shows：Compared with blank control group, three butyric acid of 100~2000 mg/kg dosage are added in feed
Glyceride, piglet survival ratio can be significantly increased, reduce grice diarrhoea rate.Three butyric acid of 500~2000 mg/kg dosage groups
Glyceride can more preferable prevention of diarrhea in piglets than Nosiheptide group.
Conclusion：Tributyrin addition can remarkably promote piglet growth in pig starter feed, improve efficiency of feed utilization, dimension
Protect its intestinal health and prevention of diarrhea in piglets.
Embodiment 4：Influence of the tributyrin to meat chicken production performance
Healthy " AA " broiler chicken of 7000 1 ages in days of selection, is randomly divided into 5 treatment groups and 2 control groups.Every group 1000, and often
Component is 5 repetitions.Tributyrin addO-on therapy is：10mg/kg、50 mg/kg、100 mg/kg、500 mg/kg、
1000 mg/kg.Positive controls use basal diet addition 2.5mg/kg Nosiheptides.Blank control group uses basal diet simultaneously
Any medicine is not added.The basal diet and additive of each group（Multivitamin, trace element, amino acid etc.）It is identical.
Each test group is under same raising and management condition, using net-rearing.All hen houses are carried out before experiment strict
Sterilize and vacant more than one week.Full period chicken group's free choice feeding is tested, free water, routinely feeding standard controls house temperature, by normal
Advise immune programme for children and carry out immunity inoculation.Experimental period is 49 d.On-test, with the end of, to be repeated as unit, is carried out to chicken
Weigh on an empty stomach, obtain its initial weight and end weight, record whole experimental period feed quantity, remaining doses and loss doses, calculate average day
Weightening (ADG), average daily gain (ADFI) and feed-weight ratio (F/G).And significance difference analysis, analysis result are carried out to result
It is shown in Table 3.
Influence of the tributyrin of table 3 to meat chicken production performance
| Group | Starting weight/g | End weight/g | Daily gain/g | Feed-weight ratio |
| Blank control group | 51.25±2.16 | 2552±149a | 51.00±3.22a | 2.11±0.09b |
| Positive controls | 51.46±2.32 | 2811±154b | 57.38±2.92b | 1.78±0.06a |
| 10mg/kg | 50.95±2.01 | 2650±151a | 53.04±3.42a | 1.99±0.14b |
| 50 mg/kg | 51.29±2.32 | 2820±147a | 56.51±3.01b | 1.90±0.04b |
| 100 mg/kg | 51.15±2.37 | 2928±139b | 58.72±2.67b | 1.71±0.07a |
| 500 mg/kg | 51.47±2.31 | 2868±185b | 57.49±3.81b | 1.79±0.11a |
| 1000 mg/kg | 51.36±2.12 | 2830±144a | 56.72±2.83b | 1.92±0.11b |
a,b:In same column different internal standards represent significant difference (P<0.05)。
Result of the test shows：Compared with negative control group, three butyric acid of 50~1000 mg/kg dosage are added in feed
Glyceride can be effectively promoted broiler chicken growth, reduce feedstuff-meat ratio.Compared with Nosiheptide group, 10mg/kg, 50mg/kg dosage
The feeding effect of three butyric acid glycerine groups is slightly worse, piglet daily gain and the Nosiheptide group of the butyric acid glycerine groups of 100 ~ 1000 mg/kg tri-
Feeding effect is suitable.
Conclusion：Tributyrin can remarkably promote growth of meat chicken in broiler fodder, improve the price of deed.
Above-mentioned embodiment is used for illustrating the present invention, only the preferred embodiments of the present invention, rather than
Limit the invention, in the protection domain of spirit and claims of the present invention, to the present invention make any modification,
Equivalent substitution, improvement etc., both fall within protection scope of the present invention.
Claims (6)
- A kind of 1. synthetic method of tributyrin, it is characterised in that：Described synthetic method uses liquid catalyst by fourth Acid directly synthesizes tributyrin with glycerine high temperature in the presence of solvent-free, and the wherein raw material mass ratio that feeds intake is：Butyric acid：It is sweet Oil：Catalyst=4-6：1：0.05-0.1, reaction temperature are 150-160 DEG C, hour in reaction time 3-5；Again with the side of vacuum distillation Method is separated tributyrin with unreacted raw material using rectifying column, and cut corresponding to collection is content 98%（w/w） Tributyrin above；Distillation reuse after with high performance liquid chromatography detection content.
- A kind of 2. synthetic method of tributyrin according to claim 1, it is characterised in that described liquid catalyst For oleum, content is calculated as 110% with sulfuric acid（w/w）.
- A kind of 3. synthetic method of tributyrin according to claim 1, it is characterised in that the vacuum distillation it is true For reciprocal of duty cycle in more than 100pa, the filler of rectifying column is ceramics or glass.
- 4. the application of tributyrin described in a kind of claim 1, it is characterised in that promote economic animal growth for preparing With the feed addictive for improving feed conversion rate, actual interpolation amount is 100-2000ppm.
- A kind of 5. application of tributyrin according to claim 4, it is characterised in that described application process be according to This product is directly added in the feed of economic animal by addition, or by this product and bearer configuration into pre-mixing agent, or with other feedings Feed additives or feedstuff are mixed into feeding after premix, concentrate feed.
- 6. a kind of application of tributyrin according to claim 1, it is characterised in that described economic animal includes The aquatic livestock of chicken, duck, goose, quail, pig, ox, sheep, horse or artificial feeding.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107950775A (en) * | 2017-12-29 | 2018-04-24 | 湖北浩华生物技术有限公司 | A kind of pig interferon derivant and its preparation method and application |
| CN108029863A (en) * | 2018-01-19 | 2018-05-15 | 广州英赛特生物技术有限公司 | The application of butyryl glycine and its derivative in animal feed additive is prepared |
| CN111149944A (en) * | 2020-01-15 | 2020-05-15 | 四川农业大学 | Premix and feed for improving reproductive capacity of broiler breeder and application of premix and feed |
| CN112666301A (en) * | 2020-12-17 | 2021-04-16 | 太仓安佑生物科技有限公司 | Method for measuring content of tributyrin |
| CN112697920A (en) * | 2020-12-23 | 2021-04-23 | 浙江高晟生物科技有限公司 | Liquid chromatography determination method for tributyrin in mixed feed additive |
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| CN106554385A (en) * | 2016-04-08 | 2017-04-05 | 浙江汇能生物股份有限公司 | Polypeptide compounds and its application in terms of livestock and poultry |
| 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 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107950775A (en) * | 2017-12-29 | 2018-04-24 | 湖北浩华生物技术有限公司 | A kind of pig interferon derivant and its preparation method and application |
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| CN111149944A (en) * | 2020-01-15 | 2020-05-15 | 四川农业大学 | Premix and feed for improving reproductive capacity of broiler breeder and application of premix and feed |
| CN112666301A (en) * | 2020-12-17 | 2021-04-16 | 太仓安佑生物科技有限公司 | Method for measuring content of tributyrin |
| CN112697920A (en) * | 2020-12-23 | 2021-04-23 | 浙江高晟生物科技有限公司 | Liquid chromatography determination method for tributyrin in mixed feed additive |
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Application publication date: 20171124 |