CN110122667B - Feed antibacterial agent and preparation method thereof - Google Patents
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- CN110122667B CN110122667B CN201910463290.6A CN201910463290A CN110122667B CN 110122667 B CN110122667 B CN 110122667B CN 201910463290 A CN201910463290 A CN 201910463290A CN 110122667 B CN110122667 B CN 110122667B
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- chain fatty
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- 239000003242 anti bacterial agent Substances 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 17
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims abstract description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 12
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims abstract description 12
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 10
- 229930195729 fatty acid Natural products 0.000 claims abstract description 10
- 239000000194 fatty acid Substances 0.000 claims abstract description 10
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims abstract description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229920005862 polyol Polymers 0.000 claims abstract description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract description 9
- 229920000223 polyglycerol Polymers 0.000 claims abstract description 9
- -1 fatty acid polyol ester Chemical class 0.000 claims abstract description 8
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 7
- 239000004310 lactic acid Substances 0.000 claims abstract description 6
- 235000014655 lactic acid Nutrition 0.000 claims abstract description 6
- 229960002446 octanoic acid Drugs 0.000 claims abstract description 6
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims abstract description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims abstract description 5
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims abstract description 5
- 235000011054 acetic acid Nutrition 0.000 claims abstract description 5
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 5
- 235000019253 formic acid Nutrition 0.000 claims abstract description 5
- 239000001530 fumaric acid Substances 0.000 claims abstract description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 4
- 150000003077 polyols Chemical class 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 20
- 238000010438 heat treatment Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- 238000005070 sampling Methods 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 9
- 150000004666 short chain fatty acids Chemical class 0.000 claims description 8
- 150000004667 medium chain fatty acids Chemical class 0.000 claims description 6
- 230000003472 neutralizing effect Effects 0.000 claims description 5
- 229940088710 antibiotic agent Drugs 0.000 abstract description 9
- 238000005886 esterification reaction Methods 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 4
- 239000003674 animal food additive Substances 0.000 abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- 125000002252 acyl group Chemical group 0.000 abstract description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 238000004821 distillation Methods 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 abstract description 2
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 238000007670 refining Methods 0.000 abstract 1
- 238000004062 sedimentation Methods 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
- ARIWANIATODDMH-UHFFFAOYSA-N Lauric acid monoglyceride Natural products CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 244000144972 livestock Species 0.000 description 6
- 244000144977 poultry Species 0.000 description 6
- 239000000341 volatile oil Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- 239000005639 Lauric acid Substances 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 238000011010 flushing procedure Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 241000723353 Chrysanthemum Species 0.000 description 2
- 235000007516 Chrysanthemum Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000246358 Thymus Species 0.000 description 2
- 235000007303 Thymus vulgaris Nutrition 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229960004106 citric acid Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000007413 intestinal health Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000001585 thymus vulgaris Substances 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 229960004543 anhydrous citric acid Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZJYFSPXGHKSDMR-UHFFFAOYSA-N dodecanoic acid 2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(CC(O)=O)C(O)=O.CCCCCCCCCCCC(O)=O ZJYFSPXGHKSDMR-UHFFFAOYSA-N 0.000 description 1
- PCVZXIPDCYWKPQ-UHFFFAOYSA-N dodecanoic acid;2-hydroxypropanoic acid Chemical compound CC(O)C(O)=O.CCCCCCCCCCCC(O)=O PCVZXIPDCYWKPQ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000003910 polypeptide antibiotic agent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A23K20/105—Aliphatic or alicyclic compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention is disclosed inAn antibacterial agent for feed and a preparation method thereof are provided, belonging to the field of feed additives. The invention adopts middle and short fatty acid and polyol to obtain middle and short fatty acid polyol ester through the processes of esterification, acylation, transesterification, neutralization sedimentation, distillation and refining. The product meets the sanitary standard of feed additives, can be used as feed antibacterial agent, can replace antibiotics, and can ensure food safety. The structure is as follows:
Description
Technical Field
The invention relates to a feed antibacterial agent, in particular to a medium-short chain fatty acid polyol ester which is suitable for replacing antibiotics in feed and a preparation method thereof, belonging to the field of feed additives.
Background
In order to promote the growth of livestock and poultry, the feed industry in China has long been to add antibiotics drugs into the feed to maintain the intestinal health of the livestock and poultry. After a large amount of antibiotics are used, the metabolism and decomposition of the antibiotics in animals are incomplete, so that the bacterial drug resistance in the environment is enhanced, the liver and kidney functions of human bodies are seriously damaged, even anaphylactic reaction is caused, and the health and living standard of the human bodies are seriously influenced. The European and American countries do not allow antibiotics to be added into the feed, and the China does not allow antibiotics to be added into the feed until 2020. Therefore, the development of the antibiotic substitution product in the feed has practical significance.
In order to ensure food safety, natural plants are used as feed antibacterial agents to be the current development trend, chinese patent 201710689951.8 reports a plant source livestock feed antibacterial additive and a preparation method thereof, wherein Chuzhou chrysanthemum essential oil is used as a main antibacterial agent, and a film-ultrasonic dispersion method is adopted to prepare Chuzhou chrysanthemum essential oil nano-liposome; chinese patent 201710689979.1 reports a plant source poultry feed antibacterial additive and a preparation method thereof, wherein thyme essential oil is used as a main antibacterial agent to prepare thyme essential oil nanoliposome. The preparation method is complex, has low extraction rate, and is inconvenient to popularize and apply. The natural plant fatty acid and the polyalcohol are utilized to synthesize lipid products, and the lipid products are used as feed antibacterial agents to replace the natural plant antibacterial agents, so that no related report is available at present.
Disclosure of Invention
The invention aims to provide a feed antibacterial agent which can replace natural plant antibacterial agents and has good antibacterial effect; another object is to provide a method for its preparation.
The feed antibacterial agent provided by the invention is a medium-short chain fatty acid polyol ester or a medium-carbon chain fatty acid and polyol ester mixed product. The medium and short chain fatty acid polyol ester has the following structure: is a mixture of c and b or a mixture of c and a or a mixture of c, b and a:
a b c
wherein RCOO is caproic acid, caprylic acid, capric acid, lauroyl or a mixed fatty acid acyl thereof;
wherein R' COO is a low carbon chain acyl group or a phosphate group with a carboxyl structure such as formic acid, acetic acid, propionic acid, butyric acid, lactic acid, citric acid, fumaric acid and the like;
the medium and short chain fatty glyceride is prepared by the following technical scheme:
adding medium short chain fatty acid and polyalcohol into a reaction kettle according to a proportion, adding a catalyst, heating to 150-200 ℃ under vacuum for reaction, sampling, measuring an acid value and controlling a reaction end point. Then cooling, neutralizing, standing and precipitating. And adding short-chain fatty acid and a catalyst, heating to 140-180 ℃ under vacuum, continuing to react, sampling to measure the acid value, and cooling after the reaction is finished to obtain the medium-short-chain fatty acid polyol ester product.
The catalyst is NaOH or KOH;
the polyalcohol is glycerol, polyglycerin and the like;
the medium-chain fatty acid is caproic acid, caprylic acid, capric acid, lauric acid or mixed fatty acid thereof.
The short chain fatty acid is formic acid, acetic acid, propionic acid, butyric acid, lactic acid, citric acid, fumaric acid or phosphoric acid and the like;
the feeding mole ratio of the three materials in the production process is as follows: polyol, medium chain fatty acid and short chain fatty acid=1:1:1-2.
The invention utilizes natural plant fatty acid and polyalcohol to synthesize ester products, and the ester products are used as feed antibacterial agents to replace antibiotics and natural plant antibacterial agents, and can be slowly decomposed into medium-short chain fatty acid monoacyl ester and short chain fatty acid (short chain is preferentially decomposed) under the action of gastrointestinal lipase in livestock and poultry bodies, thereby having the functions of sterilizing, inhibiting bacteria, regulating the PH value of the gastrointestinal tract and the like, so that the intestinal health of the livestock and poultry is maintained, and the growth of the livestock and poultry is promoted. Compared with the scheme of replacing antibiotics with antibacterial peptide, traditional Chinese medicine, essential oil and the like, the method has the characteristics of designability, stable quality, rich resources, no toxicity and harm and the like, and is convenient for industrialization.
Detailed Description
For a better illustration of the invention, examples are as follows:
example 1
Adding 310 kg of metered glycerin and 600 kg of lauric acid into a reaction kettle with vacuum condition, adding 8.5 kg of catalyst NaOH, stirring and heating to 150 ℃, reacting for two hours under vacuum condition, gradually heating to 170 ℃ for further reacting for two hours, flushing nitrogen, sampling and measuring to obtain an acid value less than 3mgkOH/g, cooling to about 80 ℃ after the acid value reaches the requirement, neutralizing, standing and settling, performing thin film distillation and molecular distillation to remove unreacted glycerin, and collecting more than 80% of lauric acid monoglyceride.
Weighing 600 kg of lauric acid monoglyceride with the content of more than 80%, putting into a reaction kettle again, adding 300 kg of butyric acid, adding 3.2 kg of catalyst NaOH, heating to more than 140 ℃ again, continuing to react for about 4 hours, measuring the acid value to be less than 3mgkOH/g, and cooling to 50 ℃ after the acid value reaches the requirement to obtain the butyryl lauric acid monoglyceride and diglyceride product.
Example 2
Adding 850 kg of measured polyglycerol and 650 kg of lauric acid into an esterification reaction kettle, adding 11.5 kg of catalyst NaOH, heating to 150 ℃ under stirring and vacuum to react for about two hours, then gradually heating to 170 ℃ to react for about two hours, flushing nitrogen to sample and measure, cooling to about 80 ℃ after the acid value is less than 3mgkOH/g to meet the requirement, neutralizing, standing and settling, removing unreacted polyglycerol, adding 400 kg of measured polyglycerol and 200 kg of butyric acid, adding 5.5 kg of KOH into the reaction kettle, heating to 150-170 ℃ again under stirring and vacuum, continuing to react for about 4 hours, sampling and measuring the acid value to be less than 3mgkOH/g, and cooling to 50 ℃ after the acid value is less than the requirement to obtain the butyryl laurate product.
Example 3
Taking 600 kg of more than 80% lauric acid monoglyceride and 300 kg of lactic acid and 3.8 kg of KOH, which are prepared in example 1, simultaneously putting the mixture into an esterification reaction kettle, heating the mixture to 150-170 ℃ again under stirring and vacuum, reacting the mixture for about 4 hours, sampling the mixture, measuring the acid value to be less than 6mgkOH/g, and cooling the mixture to 50 ℃ after the acid value reaches the requirement, thus obtaining the lactic acid lauric acid monoglyceride and diglyceride product.
Example 4
Taking more than 80% of lauric acid monoglyceride 600 kg and 250 kg of propionic acid prepared in example 1, simultaneously adding 7.5 kg of NaOH into an esterification reaction kettle, heating to 145-165 ℃ again under stirring and vacuum, reacting for about 4 hours, sampling, measuring an acid value of less than 3mgkOH/g, and cooling to 50 ℃ after the required acid value is met, thus obtaining propionyl lauric acid monoglyceride.
Example 5
Adding 850 kg of measured polyglycerol and 580 kg of octanoic acid into an esterification reaction kettle, adding 20 kg of NaOH, heating to about 150 ℃ under stirring and vacuum, reacting for about two hours, then gradually heating to about 170 ℃ for reacting for two hours, flushing nitrogen, sampling and measuring, cooling to about 80 ℃ after the acid value is less than 3mgkOH/g to meet the requirement, neutralizing, standing and settling, removing unreacted polyglycerol, adding 380 kg of measured polyglycerol product, 200 kg of butyric acid and 5.2 kg of NaOH into the reaction kettle, heating to 158-172 ℃ again under stirring and vacuum, continuing to react for about 4 hours, sampling and measuring the acid value to be less than 3mgkOH/g, cooling to 50 ℃ after the acid value is less than the requirement, and obtaining the butyryl octanoic acid polyglycerol ester product.
Example 6
Taking 600 kg of more than 80% lauric acid monoglyceride and 404 kg of anhydrous citric acid prepared in the example 1, simultaneously adding 12 kg of KOH into an esterification reaction kettle, heating to 158-175 ℃ again under stirring and vacuum, reacting for about 4 hours, sampling, measuring an acid value of less than 3mgkOH/g, and cooling to 50 ℃ after the required acid value is met, thus obtaining citric acid lauric acid monoglyceride and diglyceride.
Claims (1)
1. The preparation method of the feed antibacterial agent is characterized by comprising the following steps of: adding medium-chain fatty acid and polyalcohol into a reaction kettle according to a proportion, adding a catalyst, heating to 150-200 ℃ under vacuum for reaction, sampling, measuring an acid value and controlling a reaction end point; after the reaction is finished, cooling, neutralizing, standing and settling; then adding short-chain fatty acid and catalyst, heating to 140-180 ℃ under vacuum to continue the reaction, sampling to determine the acid value, and cooling after the reaction is finished to obtain a medium short-chain fatty acid polyol ester product;
the medium-chain fatty acid is caproic acid, caprylic acid, capric acid, lauroyl or a mixed fatty acid thereof;
the short chain fatty acid is formic acid, acetic acid, propionic acid, butyric acid, lactic acid, citric acid or fumaric acid;
wherein the polyalcohol is glycerol or polyglycerol;
the catalyst is NaOH or KOH;
feed molar ratio: polyol: medium chain fatty acids: short chain fatty acid = 1:1:1 to 2;
the feed antibacterial agent is a mixture c and b or a mixture c and a or a mixture c, b and a:
a b c
wherein RCOO is caproic acid, caprylic acid, capric acid, lauroyl or a mixed fatty acid acyl thereof;
wherein R' COO is formic acid, acetic acid, propionic acid, butyric acid, lactic acid, citric acid or fumaric acid acyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201910463290.6A CN110122667B (en) | 2019-05-30 | 2019-05-30 | Feed antibacterial agent and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910463290.6A CN110122667B (en) | 2019-05-30 | 2019-05-30 | Feed antibacterial agent and preparation method thereof |
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| CN110122667A CN110122667A (en) | 2019-08-16 |
| CN110122667B true CN110122667B (en) | 2023-06-23 |
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| WO2024003941A1 (en) * | 2022-07-01 | 2024-01-04 | Fine Organic Industries Limited | An ester product of polyglycerol |
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| 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 |
| 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 |
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5462967A (en) * | 1991-06-17 | 1995-10-31 | Kao Corporation | Feed additive for livestock and feed for livestock |
| TW414697B (en) * | 1996-12-11 | 2000-12-11 | Riken Vitamin Co | Antimicrobial agent for food |
| WO2001097799A1 (en) * | 2000-06-20 | 2001-12-27 | Nutrition Sciences | Medium chain fatty acids applicable as antimicrobial agents |
| GB0410038D0 (en) * | 2004-05-05 | 2004-06-09 | Danisco | Composition |
| CN101161802A (en) * | 2006-10-12 | 2008-04-16 | 李建成 | Method for manufacturing polyglycerol compound (medium-carbon) fatty acid ester |
| BE1021434B1 (en) * | 2013-11-20 | 2015-11-20 | Proviron Holding | FEED FEED WITH A COMBINATION OF MONOGLYCERIDES. |
| CN104529773B (en) * | 2014-12-12 | 2016-06-15 | 武汉轻工大学 | A kind of preparation method and application of sad glyceride lactate feed additive |
| CN106858065B (en) * | 2017-02-28 | 2020-11-17 | 齐鲁工业大学 | Hybrid glycerides and methods of production and use |
| 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 |
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2019
- 2019-05-30 CN CN201910463290.6A patent/CN110122667B/en active Active
Patent Citations (5)
| 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 |
| 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 |
| 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 |
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| CN110122667A (en) | 2019-08-16 |
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