CN110122667A - A kind of feed antibacterial agent and preparation method thereof - Google Patents

A kind of feed antibacterial agent and preparation method thereof Download PDF

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Publication number
CN110122667A
CN110122667A CN201910463290.6A CN201910463290A CN110122667A CN 110122667 A CN110122667 A CN 110122667A CN 201910463290 A CN201910463290 A CN 201910463290A CN 110122667 A CN110122667 A CN 110122667A
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China
Prior art keywords
acid
chain fatty
acyl group
polyalcohol
reaction
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CN201910463290.6A
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CN110122667B (en
Inventor
楚喆
李兴伟
楚军政
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Henan Zhengtong Food Technology Co ltd
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HENAN ZHENGTONG CHEMICAL CO Ltd
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    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23KFODDER
    • A23K20/00Accessory food factors for animal feeding-stuffs
    • A23K20/10Organic substances
    • A23K20/105Aliphatic or alicyclic compounds

Abstract

The invention discloses a kind of feed antibacterial agents and preparation method thereof, belong to feed additive field.The processes such as short fatty acid and polyalcohol are settled through esterification, acylation, transesterification, neutralization in present invention use, distillation refines obtain Short-Chain Fatty Acids polyol ester.The product meets feed addictive sanitary standard, can be used for feed antibacterial agent, and substitute antibiotics ensure food safety.Its structure is as follows:

Description

A kind of feed antibacterial agent and preparation method thereof
Technical field
The present invention relates to a kind of feed antibacterial agent, the Short-Chain Fatty Acids especially suitable for substitute antibiotics in feed are polynary Alcohol ester and preparation method thereof belongs to feed additive field.
Background technique
China's feedstuff industry adds antibiotics maintenance poultry all the time in order to promote the growths of livestock and poultry in feed The intestinal health of fowl.Metabolic breakdown not exclusively causes the bacterium in environment resistance in animal body after a large amount of uses of antibiotics Pharmacological property enhancing, causes serious harm to the hepatic and renal function of human body, or even can cause allergic reaction, and it is strong to have seriously affected human body Health and living standard.American-European countries does not allow to add antibiotic in feed, and China to the year two thousand twenty also no longer allows in feed Add antibiotic.For this purpose, the development of antibiotic substitute products has realistic meaning in feed.
In order to ensure food safety, current development trend is had become using natural plants as feed antibacterial agent, China is specially Benefit 201710689951.8 reports a kind of plant source feed stripped antibacterial additives and preparation method thereof, is with chu chrysanthemum essential oil Main antibacterial agent prepares chu chrysanthemum essence oil nanometer liposome using film-ultrasonic wave dispersion technique;Chinese patent 201710689979.1 is reported A kind of plant source poultry feed antibacterial additives in road and preparation method thereof, with thyme essential oil for main antibacterial agent, preparation hundred In essential oil nano liposomes.Preparation method is complicated, and recovery rate is lower, and inconvenience promotes and applies.And utilize natural vegetable fats Acid and polyalcohol synthesize lipid product, as feed antibacterial agent, substitute natural plants antibacterial agent, do not see related report at present Road.
Summary of the invention
Natural plants antibacterial agent, and the feed antibacterial of good anti-bacterial effect can be substituted the purpose of the present invention is to provide a kind of Agent;Another object is to provide preparation method.
Feed antibacterial agent of the present invention is Short-Chain Fatty Acids polyol ester or it mixes medium-chain fatty acid and more First ester product.The Short-Chain Fatty Acids polyol ester has the following structure: for c and b mixture or c and a mixture or c, B, a mixture:
a b c
Wherein RCOO is caproic acid, octanoic acid, capric acid, lauric acid acyl group or its fatty acid mixed acyl group;
Wherein R'COO is the low carbon chain acid with carboxyl structure such as formic acid, acetic acid, propionic acid, butyric acid, lactic acid, citric acid, fumaric acid Acyl group or phosphate;
The Short-Chain Fatty Acids glyceride is prepared by the following technical programs:
Short-Chain Fatty Acids and polyalcohol are put into reaction kettle according to the ratio, while adding catalyst, is warming up under vacuum Then 150-200 DEG C of reaction is measured by sampling acid value and controls reaction end.Then cool down, neutralize, staticly settle.Short chain is put into again Fatty acid and catalyst are warming up to 140-180 DEG C under vacuum, and the reaction was continued, and acid value is measured by sampling, and cooling obtains after reaction Short-Chain Fatty Acids polyol ester product.
The catalyst is NaOH or KOH;
The polyalcohol is glycerol, polyglycereol etc.;
The medium chain fatty acid is caproic acid, octanoic acid, capric acid, lauric acid or its fatty acid mixed.
The short chain fatty acids are formic acid, acetic acid, propionic acid, butyric acid, lactic acid, citric acid, fumaric acid or phosphoric acid etc.;
The molar ratio of three kinds of materials in production process: polyalcohol: medium chain fatty acid: short chain fatty acids=1:1:1~2.
The present invention utilizes natural vegetable fatty acids and polyalcohol synthesizing ester product, as feed antibacterial agent, substitution Antibiotic substitutes natural plants antibacterial agent, this esters product is interior under the action of gastrointestinal lipase to livestock and poultry body, can be sustained point Solution is Short-Chain Fatty Acids list acyl rouge and short chain fatty acids (short chain preferentially decomposes), has sterilization, antibacterial, adjusting gastrointestinal tract pH value Etc. functions promote the growth of livestock and poultry to safeguard the intestinal health of livestock and poultry.With the substitute antibiotics side such as antibacterial peptide, Chinese medicine, essential oil Case is compared, have the characteristics that can to design, quality it is stable, resourceful, nontoxic, just industrialize with realizing.
Specific embodiment
It is as follows for embodiment to be better illustrated to the present invention:
Embodiment 1
310 kg of glycerin measured and 600 kilograms of lauric acid are put into the reaction kettle of vacuum condition, while addition is urged 8.5 kilograms of agent NaOH, after stirring is warming up to 150 DEG C, after reacting two hours under vacuum conditions, then gradually it is warming up to 170 DEG C the reaction was continued two hours, rushes nitrogen sampling and measuring, and acid value is less than 3mgkOH/g, after reaching requirement, is cooled to 80 DEG C or so, in With, quiescent settling, carry out thin-film distillation and molecular distillation remove unreacted glycerol and collect 80% or more lauric acid list it is sweet Ester.
600 kilograms of Glycerol Monolaurate for weighing 80% or more content put into reaction kettle again, add 300 kilograms of butyric acid, Add 3.2 kilograms of catalyst n aOH is warming up to 140 DEG C or more again simultaneously, and the reaction was continued 4 hours or so, and measurement acid value is less than 3mgkOH/g is cooled to 50 DEG C after reaching requirement, obtains butyryl lauric acid list double glyceride product.
Embodiment 2
Measure 850 kilograms of polyglycereol and 650 kilograms of lauric acid are put into reaction kettle of the esterification, while it is public to add 11.5 Jin catalyst n aOH is being stirred and is being warming up to 150 DEG C or so under vacuum, reacting about two hours, be then gradually warming up to 170 DEG C again Left and right is reacted two hours again, is rushed nitrogen sampling and measuring and is cooled to 80 DEG C or so after acid value reaches requirement less than 3mgkOH/g, in With, quiescent settling, unreacted polyglycereol is removed, then 400 kilograms and 200 kilograms of butyric acid, 5.5 kilograms of the product for measuring KOH is put into reaction kettle, is being warming up between 150 DEG C -170 DEG C again under stirring and vacuum, the reaction was continued 4 hours or so, takes Sample measures acid value and is less than 3mgkOH/g, is cooled to 50 DEG C after reaching requirement, obtains butyryl lauric acid polyglyceryl ester product.
Embodiment 3
80% or more lauric acid monoglyceride, 600 kilograms and 300 kilograms lactic acid made from Example 1,3.8 kilograms of KOH, simultaneously It puts into the reaction kettle of esterification, is being warming up between 150 DEG C -170 DEG C again under stirring and vacuum, react about 4 hours or so, take Sample measures acid value and is less than 6mgkOH/g, is cooled to 50 DEG C after reaching requirement, obtains lactic acid lauric acid list double glyceride product.
Embodiment 4
80% or more lauric acid monoglyceride, 600 kilograms and 250 kilograms propionic acid made from Example 1,7.5 kilograms of NaOH are simultaneously It puts into reaction kettle of the esterification, is being warming up between 145 DEG C -165 DEG C again under stirring and vacuum, reacted about 4 hours or so, sampling It measures acid value and is less than 3mgkOH/g, be cooled to 50 DEG C after reaching requirement, obtain propionyl lauric acid list double glyceride.
Embodiment 5
The octanoic acid of measure 850 kilograms of polyglycereol and 580 kilograms is put into reaction kettle of the esterification, while adding 20 kilograms NaOH is being stirred and is being warming up to 150 DEG C or so under vacuum, reacting about two hours, be then gradually warming up to 170 DEG C or so again again instead It answers two hours, rushes nitrogen sampling and measuring, after acid value reaches requirement less than 3mgkOH/g, be cooled to 80 DEG C or so, neutralize, it is static heavy Drop removes unreacted polyglycereol, then 380 kilograms of the product that will be measured, 200 kilograms and 5.2 kilograms NaOH investments of butyric acid It in reaction kettle, is being warming up between 158 DEG C -172 DEG C again under stirring and vacuum, the reaction was continued 4 hours or so, and acid is measured by sampling Value is less than 3mgkOH/g, is cooled to 50 DEG C after reaching requirement, obtains butyryl octanoic acid polyglycerol ester product.
Embodiment 6
80% or more lauric acid monoglyceride, 600 kilograms and 404 kilograms anhydrous citric acids, 12 kilograms of KOH made from Example 1 It puts into reaction kettle of the esterification simultaneously, is stirring and be warming up to 158 DEG C -175 DEG C under vacuum again, reacting about 4 hours or so, sampling It measures acid value and is less than 3mgkOH/g, be cooled to 50 DEG C after reaching requirement, obtain citric acid lauric acid list double glyceride.

Claims (2)

1. a kind of feed antibacterial agent, it is characterised in that: the antibacterial agent be Short-Chain Fatty Acids polyol ester, be c and b mixture or C and a mixture or c, b, a mixture:
a b c
Wherein RCOO is caproic acid, octanoic acid, capric acid, lauric acid acyl group or its fatty acid mixed acyl group;
Wherein R'COO is formic acid, acetic acid, propionic acid, butyric acid, lactic acid, citric acid, fumaric acid acyl group or phosphate;
Wherein polyalcohol is glycerol or polyglycereol.
2. preparing feed antibacterial agent method as described in claim 1, which is characterized in that prepared by following steps: by middle chain Fatty acid and polyalcohol are put into reaction kettle according to the ratio, while being added catalyst and being warming up to 150-200 DEG C of reaction under vacuum, are taken Sample measures acid value and controls reaction end;After reaction, cool down, neutralize, standing sedimentation;Then short chain fatty acids are put into again and are urged Agent, being warming up to 140-180 DEG C under vacuum, the reaction was continued, and acid value is measured by sampling, after reaction, cooling, obtain in short chain rouge Fat acid polyol ester product;
The medium chain fatty acid is caproic acid, octanoic acid, capric acid, lauric acid acyl group or its fatty acid mixed;
The short chain fatty acids are formic acid, acetic acid, propionic acid, butyric acid, lactic acid, citric acid, fumaric acid or phosphoric acid;
Wherein polyalcohol is glycerol or polyglycereol;
The catalyst is NaOH or KOH;
Molar ratio: polyalcohol: medium chain fatty acid: short chain fatty acids=1:1:1~2.
CN201910463290.6A 2019-05-30 2019-05-30 Feed antibacterial agent and preparation method thereof Active CN110122667B (en)

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CN110122667B CN110122667B (en) 2023-06-23

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024003941A1 (en) * 2022-07-01 2024-01-04 Fine Organic Industries Limited An ester product of polyglycerol

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8815426D0 (en) * 1988-06-29 1988-08-03 Unilever Plc Process for synthesis of polyol fatty acid polyesters
EP0582246A2 (en) * 1992-08-07 1994-02-09 Solvay Fluor und Derivate GmbH Mixture of polyglycerine fatty acids esters
US5462967A (en) * 1991-06-17 1995-10-31 Kao Corporation Feed additive for livestock and feed for livestock
EP0847704A1 (en) * 1996-12-11 1998-06-17 Riken Vitamin Co., Ltd. Antimicrobial agents for foods
US20030176500A1 (en) * 2000-06-20 2003-09-18 Koen Molly Medium chain fatty acids applicable as antimicrobial agents
WO2005104878A1 (en) * 2004-05-05 2005-11-10 Danisco A/S Anti-microbial composition
CN101161802A (en) * 2006-10-12 2008-04-16 李建成 Method for manufacturing polyglycerol compound (medium-carbon) fatty acid ester
ITFI20090050A1 (en) * 2009-03-16 2010-09-17 Fernando Cantini COMPOSITIONS CONTAINING MONOGLICERIDES OF ORGANIC ACIDS FROM C1 TO C7 AND GLYCEROL, THEIR PREPARATION AND USE AS ANTIBACTERIALS IN THE ZOOTECHNY.
WO2014176515A2 (en) * 2013-04-26 2014-10-30 Solazyme, Inc. Low polyunsaturated fatty acid oils and uses thereof
CN104529773A (en) * 2014-12-12 2015-04-22 武汉轻工大学 Preparation method and applications of lacti-glyceride caprylate feed additives
CN105916385A (en) * 2013-11-20 2016-08-31 普罗维隆控股股份有限公司 Animal feed comprising a combination of mono glycerides
CN106858065A (en) * 2017-02-28 2017-06-20 齐鲁工业大学 Heterozygosis glyceride and production method and application
CN109511811A (en) * 2019-01-29 2019-03-26 潍坊加易加生物科技有限公司 One kind is for anti-Short-Chain Fatty Acids essential oil formulation and preparation method thereof and its application
FR3071496A1 (en) * 2017-09-25 2019-03-29 Guerin MIXED GLYCERIDE OF FORMICIC ACID, COMPOSITION COMPRISING AT LEAST ONE SUCH MIXED GLYCERIDE, PROCESS FOR PREPARATION AND USES

Patent Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8815426D0 (en) * 1988-06-29 1988-08-03 Unilever Plc Process for synthesis of polyol fatty acid polyesters
US5462967A (en) * 1991-06-17 1995-10-31 Kao Corporation Feed additive for livestock and feed for livestock
EP0582246A2 (en) * 1992-08-07 1994-02-09 Solvay Fluor und Derivate GmbH Mixture of polyglycerine fatty acids esters
EP0847704A1 (en) * 1996-12-11 1998-06-17 Riken Vitamin Co., Ltd. Antimicrobial agents for foods
US20030176500A1 (en) * 2000-06-20 2003-09-18 Koen Molly Medium chain fatty acids applicable as antimicrobial agents
WO2005104878A1 (en) * 2004-05-05 2005-11-10 Danisco A/S Anti-microbial composition
CN101161802A (en) * 2006-10-12 2008-04-16 李建成 Method for manufacturing polyglycerol compound (medium-carbon) fatty acid ester
US20120029075A1 (en) * 2009-03-16 2012-02-02 Fernando Cantini Compositions containing c1 to c7 organic acid monoglycerides and glycerol, their preparation and use as antibacterials and anti-mould agents
ITFI20090050A1 (en) * 2009-03-16 2010-09-17 Fernando Cantini COMPOSITIONS CONTAINING MONOGLICERIDES OF ORGANIC ACIDS FROM C1 TO C7 AND GLYCEROL, THEIR PREPARATION AND USE AS ANTIBACTERIALS IN THE ZOOTECHNY.
WO2014176515A2 (en) * 2013-04-26 2014-10-30 Solazyme, Inc. Low polyunsaturated fatty acid oils and uses thereof
CN105916385A (en) * 2013-11-20 2016-08-31 普罗维隆控股股份有限公司 Animal feed comprising a combination of mono glycerides
US20160286836A1 (en) * 2013-11-20 2016-10-06 Proviron Holding N.V. Animal feed comprising a combination of mono glycerides
CN104529773A (en) * 2014-12-12 2015-04-22 武汉轻工大学 Preparation method and applications of lacti-glyceride caprylate feed additives
CN106858065A (en) * 2017-02-28 2017-06-20 齐鲁工业大学 Heterozygosis glyceride and production method and application
FR3071496A1 (en) * 2017-09-25 2019-03-29 Guerin MIXED GLYCERIDE OF FORMICIC ACID, COMPOSITION COMPRISING AT LEAST ONE SUCH MIXED GLYCERIDE, PROCESS FOR PREPARATION AND USES
CN109511811A (en) * 2019-01-29 2019-03-26 潍坊加易加生物科技有限公司 One kind is for anti-Short-Chain Fatty Acids essential oil formulation and preparation method thereof and its application

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
王国建编著: "《功能高分子材料》", 30 June 2014, 同济大学出版社, pages: 1 - 2 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024003941A1 (en) * 2022-07-01 2024-01-04 Fine Organic Industries Limited An ester product of polyglycerol

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Address after: 450064 South West Point, Intersection of Jianshe Road and Gongye Road, Xingyang City, Zhengzhou City, Henan Province

Patentee after: Henan Zhengtong Food Technology Co.,Ltd.

Address before: 450064 South West Point, Intersection of Jianshe Road and Gongye Road, Xingyang City, Zhengzhou City, Henan Province

Patentee before: HENAN ZHENGTONG CHEMICAL Co.,Ltd.