CN115197110A - Preparation method of hydroxymethionine and application of hydroxymethionine in acidifying agent - Google Patents
Preparation method of hydroxymethionine and application of hydroxymethionine in acidifying agent Download PDFInfo
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- CN115197110A CN115197110A CN202210999886.XA CN202210999886A CN115197110A CN 115197110 A CN115197110 A CN 115197110A CN 202210999886 A CN202210999886 A CN 202210999886A CN 115197110 A CN115197110 A CN 115197110A
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Abstract
The invention discloses a preparation method of hydroxy methionine and application thereof in an acidifier, wherein the preparation method comprises the following steps: pulping, dropwise adding sodium nitrite, and stirring for reaction; the stirring reaction has two methods, the first method is to control the temperature of the mixed solution to 23-27 ℃, start stirring and stir for 28-30min at the stirring speed of 80-120rpm to obtain egg orange clear solution; secondly, adding a catalyst into the mixed solution, controlling the temperature to 23-27 ℃, starting stirring, and stirring at a stirring speed of 80-120rpm for 28-30min to obtain egg orange clear liquid; the preparation method of the invention can simplify the preparation process, reduce the dependence on reaction temperature, reduce the generation of three wastes and toxic substances in the preparation and improve the purity of the hydroxy methionine.
Description
Technical Field
The invention relates to the technical field of methionine, in particular to a preparation method of hydroxy methionine and application thereof in an acidifier.
Background
Methionine, also known as methionine, is an important animal nutrition. Methionine was first discovered from casein hydrolysate by Miller in 1921, pajie was first chemically synthesized successfully in 1928, and Decusate in Germany led to industrial production in 1948. The main component of protein is amino acid, methionine is essential amino acid of all vertebrates, and is involved in more than 80 biochemical reactions in vivo, and for ruminants, methionine is the first or second limiting amino acid of animals such as high-yield cows, growing beef cattle and goats, and only a small part of unprotected methionine can enter the small intestine due to the degradation of rumen microorganisms of ruminants, so how to protect methionine or hydroxy methionine analogue capable of passing through rumen becomes important for research.
Hydroxymethionine is usually used in a form of calcium salt and ammonium salt nutrition, norweiss develops the hydroxymethionine into norweisamine micro-mineral, namely hydroxymethionine micro-mineral salt, and the hydroxymethionine micro-mineral salt is used in feed additives as trace mineral elements and protein sources required by organisms, and obtains the north american animal feed additive 'product differentiation outstanding prize' in 2012.
Acidifier effect study of liquid methionine hydroxy analogue (HMB)' feed industry, vol.27, no. 12, 2006; the king discloses that hydroxymethionine can be used as an acidifier, and can kill bacteria in intestinal tracts of livestock and poultry, improve the health of the intestinal tracts and promote the growth of intestinal villi. On the market, hydroxymethionine is usually sold in the form of salt, and small batches of acid are sold at higher prices, and are used as acidulants in places where the acid is less valuable. When the inventor researches the application of the medium-chain fatty acid as an acidifier in cooperation with the small-molecule acid, the inventor unexpectedly finds that the hydroxymethionine can compatibilize part of the medium-chain fatty acid in 60% of formic acid, so that the hydroxymethionine not only can be used as the acidifier, but also plays a role in compatibilizing media, and has a function-nutrition effect similar to that of the medium-chain fatty acid.
Hydroxymethionine is regarded as one of animal protein sources and developed vigorously, and researchers have developed methods such as a cyanohydrin hydrolysis method, a cyanohydrin enzymatic hydrolysis method, a methionine conversion method, a keto acid conversion method, a ketol oxidation method, a cyanophosphoric acid diethyl ester method, an alpha-hydroxy-gamma-butyrolactone method and the like in sequence.
The process is essentially the conversion of functional groups, the diazotization reaction usually adopts sulfuric acid and hydrochloric acid as media, the aim is that diazotize salt exists more stably, if smooth denitrification is needed, the concentration of the sulfuric acid or the hydrochloric acid needs to be low enough, taking the hydrochloric acid as an example, the concentration is lower than 10%, the temperature is kept below 0 ℃, the temperature is increased to more than 5 ℃ after the diazotization is finished to finish the denitrification, and the operation process is more complicated, so the operation can avoid the appearance of self-coupled products; however, the hydroxymethionine prepared by sulfuric acid or hydrochloric acid cannot be directly used for preparing an acidifier, the hydroxymethionine needs to be separated from inorganic acid to obtain pure hydroxymethionine, the pure hydroxymethionine is compounded with other organic acid, the separated acid solution needs three-waste treatment such as neutralization, the price of the methionine is higher than that of the hydroxymethionine, the process using the inorganic acid has no economy at all, and oily self-coupling matters exist in the reaction finished solution and float; the cyanohydrin hydrolysis method comprises the steps of reacting methyl thiopropionaldehyde with hydrocyanic acid to obtain 2-hydroxy-4-methylthiobutyronitrile, hydrating the obtained 2-hydroxy-4-methylthiobutyronitrile under the action of sulfuric acid to generate 2-hydroxy-4-methylthiobutyronitrile, hydrolyzing the obtained product under the action of sulfuric acid to obtain hydrolysate containing the hydroxy methionine analogue, ammonium sulfate and ammonium bisulfate, and separating and purifying the hydroxy methionine analogue from the 2-hydroxy-4-methylthiobutyronitrile hydrolysate; the cyanide alcohol method is the mainstream production method in the industry at present, but the virulent hydrocyanic acid is used in the process, and the hydrolysis of the cyano group generates a large amount of waste salt, so that the method is not favorable for small-scale production.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a preparation method of hydroxymethionine and application thereof in an acidifier, which can simplify the preparation process, reduce the dependence on reaction temperature, reduce the generation of three wastes and toxic substances in preparation and improve the purity of the hydroxymethionine.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
a method for producing hydroxymethionine, comprising: pulping, dropwise adding sodium nitrite, and stirring for reaction;
the step of pulping, formic acid and methionine are added into a reaction container, and pulping is carried out for 28-32min to obtain slurry;
the mass fraction of the formic acid is 84-86%;
the mass fraction of the methionine is 97-99%;
wherein the mass ratio of formic acid to methionine is 95-105;
dropwise adding sodium nitrite, slowly dropwise adding a sodium nitrite solution into the slurry, controlling the dropwise adding speed to be 0.5-1ml/min, controlling the temperature of a four-mouth bottle to be less than or equal to 35 ℃ in the dropwise adding process, and obtaining a mixed solution after the dropwise adding is finished;
the mass fraction of the sodium nitrite solution is 33-37%;
wherein the mass ratio of the sodium nitrite solution to the slurry is 15-16;
the stirring reaction has two methods, the first method is to control the temperature of the mixed solution to 23-27 ℃, start stirring and stir for 28-30min at the stirring speed of 80-120rpm to obtain egg orange clear solution;
secondly, adding a catalyst into the mixed solution, controlling the temperature to 23-27 ℃, starting stirring, and stirring at a stirring speed of 80-120rpm for 28-30min to obtain egg orange clear liquid;
wherein the mass ratio of the catalyst to the mixed solution is 0.01;
the preparation method of the catalyst comprises the following steps: uniformly mixing xanthan gum, succinic acid, methionine and polyethylene glycol 4000, placing the mixture in a closed reactor, vacuumizing the closed reactor until the vacuum degree is 0.02-0.03MPa, controlling the temperature of the closed reactor to be 40-45 ℃, standing the mixture in the closed reactor for 25-30min to obtain a primary catalyst, mixing the primary catalyst, sodium o-phenylphenol and phytic acid, performing ball milling, and after the ball milling is finished, placing the mixture at-15 ℃ to-12 ℃ for freezing treatment for 18-22min to obtain a catalyst;
wherein, the mass ratio of xanthan gum, succinic acid, methionine and polyethylene glycol 4000 is 0.8-1;
wherein the mass ratio of the primary catalyst, the sodium o-phenylphenol and the phytic acid is 4.5-5;
the ball-material ratio in the ball milling is 10-12, the rotating speed is 300-320rpm, and the time is 30-35min.
The application of the hydroxymethionine in the acidifying agent and the application of the hydroxymethionine obtained by the preparation method in the acidifying agent.
Compared with the prior art, the invention has the beneficial effects that:
(1) The preparation method of the hydroxymethionine can simplify the preparation process;
(2) The preparation method of the hydroxymethionine reduces the dependence on the reaction temperature, and the reaction can be carried out at 23-27 ℃;
(3) The preparation method of the hydroxymethionine can reduce the generation of three wastes and toxic substances in the preparation;
(4) The preparation method of the hydroxymethionine can improve the content of the hydroxymethionine in the prepared product, and the content of the hydroxymethionine in the prepared product can reach 80.2-89.1%;
(5) The preparation method of the hydroxymethionine can avoid the generation of oily liquid floating substances in the prepared product;
(6) According to the preparation method of the hydroxymethionine, the prepared hydroxymethionine has antibacterial property and can inhibit the propagation of escherichia coli and staphylococcus aureus.
Detailed Description
In order to more clearly understand the technical features, objects, and effects of the present invention, specific embodiments of the present invention will now be described.
Formic acid, acetic acid, propionic acid in examples and comparative examples were purchased from russian chemical group ltd;
methionine in examples and comparative examples was purchased from Shandong New and patent drug industries, inc.
EXAMPLE 1 diazotization of formic acid to Hydroxymethionine
Adding 100g of 85% formic acid and 10g of 99% methionine into a 500ml four-mouth bottle with a stirring paddle, a thermometer and a constant-pressure dropping funnel, pulping for 30min, controlling the temperature to 25 ℃, taking 15.5g of 35% sodium nitrite solution, adding the 35% sodium nitrite solution into the dropping funnel, slowly dropwise adding the solution into the four-mouth bottle, controlling the dropwise adding speed to be 0.5ml/min, controlling the temperature of the four-mouth bottle to be less than or equal to 35 ℃ in the dropwise adding process, after the dropwise adding is finished, controlling the temperature of the four-mouth bottle to be 25 ℃, starting stirring and stirring for 30min at the stirring speed of 100rpm to obtain an egg orange clear liquid without oily liquid floaters, wherein the content of hydroxymethionine in the egg orange clear liquid is 81.5%.
EXAMPLE 2 diazotization of acetic acid to Hydroxymethionine
Adding 100g of 99% acetic acid and 10g of 99% methionine into a 500ml four-mouth bottle with a stirring paddle, a temperature agent and a constant pressure dropping funnel, pulping for 30min, controlling the temperature to be 25 ℃, taking 15.5g of 35% sodium nitrite solution, adding the 35% sodium nitrite solution into the dropping funnel, slowly dropping the solution into the four-mouth bottle at a dropping speed of 0.5ml/min, controlling the temperature of the four-mouth bottle to be not more than 35 ℃ in the dropping process, after dropping, controlling the temperature of the four-mouth bottle to be 25 ℃, starting stirring and stirring at a stirring speed of 100rpm for 30min to obtain an egg orange clear solution without oily liquid floaters, wherein the content of hydroxymethionine in the egg orange clear solution is 82.4%.
EXAMPLE 3 diazotization of propionic acid to prepare Hydroxymethionine
Adding 100g of 99% propionic acid and 10g of 99% methionine into a 500ml four-mouth bottle with a stirring paddle, a temperature agent and a constant-pressure dropping funnel, pulping for 30min, taking 15.5g of 35% sodium nitrite solution, adding the 35% sodium nitrite solution into the dropping funnel, slowly dropping the solution into the four-mouth bottle, controlling the dropping speed to be 0.5ml/min, controlling the temperature of the four-mouth bottle in the dropping process to be less than or equal to 35 ℃, after the dropping is finished, controlling the temperature of the four-mouth bottle to be 25 ℃, starting stirring and stirring for 30min at the stirring speed of 100rpm to obtain egg orange clear liquid without oily liquid floaters, wherein the content of hydroxymethionine in the egg orange clear liquid is 80.2%.
EXAMPLE 4 diazotization of formic acid to Hydroxymethionine
Adding 100g of 85% formic acid and 10g of 99% methionine into a 500ml four-mouth bottle with a stirring paddle, a thermometer and a constant-pressure dropping funnel, pulping for 30min, controlling the temperature to be 25 ℃, taking 15.5g of 35% sodium nitrite solution, adding the 35% sodium nitrite solution into the dropping funnel, slowly dropwise adding the solution into the four-mouth bottle, controlling the dropwise adding speed to be 0.5ml/min, controlling the temperature of the four-mouth bottle to be less than or equal to 35 ℃ in the dropwise adding process, adding 0.01g of catalyst after the dropwise adding is finished, then controlling the temperature of the four-mouth bottle to be 25 ℃, starting stirring and stirring at the stirring speed of 100rpm for 30min to obtain an egg orange clear liquid without oily liquid floaters, wherein the content of hydroxy methionine in the egg orange clear liquid is 89.1%;
the preparation method of the catalyst comprises the following steps: uniformly mixing 1g of xanthan gum, 0.2g of succinic acid, 0.5g of methionine and 4000 g of polyethylene glycol, placing the mixture in a closed reactor, vacuumizing the closed reactor to the vacuum degree of 0.02MPa, controlling the temperature of the closed reactor to 40 ℃, standing the mixture in the closed reactor for 25min to obtain a primary catalyst, mixing the primary catalyst, 0.2g of sodium o-phenylphenol and 0.2g of phytic acid, and then carrying out ball milling, wherein the ball-to-material ratio during ball milling is controlled to be 10, the rotating speed is 300rpm, the time is 30min, and after the ball milling is finished, placing the mixture at the temperature of-15 ℃ for freezing treatment for 20min to obtain the catalyst.
Comparative example 1 preparation of Hydroxymethionine by diazotization of sulfuric acid
In a 500ml four-mouth bottle with a stirring paddle, a temperature agent and a constant pressure dropping funnel, 100g of 85% concentrated sulfuric acid and 10g of 99% methionine are added, the mixture is pulped for 30min, and the temperature is reduced to-15 ℃ in an ice bath. Adding 15.5g of 35% sodium nitrite solution (prepared in advance and then placed at-15 ℃ for standing for 8 h) into a dropping funnel, slowly dropping into a four-mouth bottle, controlling the dropping speed to be 0.5ml/min, controlling the temperature of the four-mouth bottle to be less than or equal to 5 ℃ in the dropping process, standing for 30min at 5 ℃ after the dropping is finished, then heating to 15 ℃, starting stirring and stirring at the stirring speed of 100rpm for 8h to obtain light yellow clear liquid, wherein the clear liquid contains oily liquid floaters with the red wine color of 1-angle coin size, and the content of hydroxy methionine in the light yellow clear liquid after the liquid floaters are filtered is 72.5%.
Comparative example 2 diazotization of hydrochloric acid to produce Hydroxymethionine
In a 500ml four-mouth bottle with a stirring paddle, a temperature agent and a constant pressure dropping funnel, 100g of 30% hydrochloric acid and 10g of 99% methionine are added, the mixture is pulped for 30min, and the temperature is reduced to-15 ℃ in an ice bath. Adding 15.5g of 35% sodium nitrite solution (prepared in advance and then placed at-15 ℃ for standing for 8 h) into a dropping funnel, slowly dropping into a four-mouth bottle, controlling the dropping speed to be 0.5ml/min, controlling the temperature of the four-mouth bottle to be less than or equal to 5 ℃ in the dropping process, standing for 30min at 5 ℃ after the dropping is finished, then heating to 15 ℃, starting stirring and stirring at the stirring speed of 100rpm for 8h to obtain light yellow clear liquid, wherein the clear liquid contains oily liquid floaters with the red wine color of 1-angle coin size, and the content of hydroxy methionine in the light yellow clear liquid after the liquid floaters are filtered is 68.2%.
Test example 1
Research shows that the acidification agent added into the feed plays a key role in healthy growth of animals, the hydroxy methionine analogue (HMB) is a product obtained by substituting hydroxyl in methionine, and is used as a methionine source in the feed of domestic fowls, the equimolar hydroxy methionine analogue (HMB) and methionine have the same activity on piglets, but the bacteriostatic effect of the equimolar hydroxy methionine analogue (HMB) is greater than that of the methionine;
the bacteriostatic effect of the hydroxymethionine and the composition of hydroxymethionine and acidulant prepared in examples 1-4 and comparative examples 1-2 was tested by this test example, and 6 samples, sample nos. 1-6, were first prepared, and the correspondence between the samples and hydroxymethionine was as follows:
then, carrying out bacteriostasis test by a minimum bacteriostasis concentration (MIC) 96-well plate method, preparing 700ml of culture medium, evenly distributing the culture medium into 7 triangular flasks numbered 1-7, preparing 7ml of bacterial suspension, controlling the concentration of escherichia coli in the bacterial suspension to be 100CFU/ml and the concentration of staphylococcus aureus to be 100CFU/ml, evenly distributing the bacterial suspension into 7 parts, marking 1-7 bacterial suspensions, and respectively inoculating 1-7 bacterial suspensions into the 1-7 triangular flasks;
respectively adding 0.2g of No. 1-6 samples into No. 1-6 triangular flasks, then respectively adding 1ml of TTC test solution color developing agent into No. 1-7 triangular flasks, placing the flasks in a constant-temperature incubator at 37 ℃ for 20h, and recording whether the No. 1-7 triangular flasks develop color or not, wherein the recording result is as follows:
according to the color development principle of TTC, if bacteria grow, the TTC test solution is red, and if bacteria do not grow, the TTC test solution is not colored, which indicates that after the methionine is converted into the hydroxy methionine by the preparation method of the embodiment 1-3, the bacteriostatic effect is obvious, and the application of the methionine in piglet feed can improve the digestion and absorption of piglets on the feed, reduce the diarrhea of piglets and promote the growth of piglets.
All percentages used in the present invention are mass percentages unless otherwise indicated.
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A method for producing hydroxymethionine, comprising: pulping, dropwise adding sodium nitrite, and stirring for reaction;
the stirring reaction has two methods, the first method is to control the temperature of the mixed solution to 23-27 ℃, start stirring and stir for 28-30min at the stirring speed of 80-120rpm to obtain egg orange clear solution;
secondly, adding a catalyst into the mixed solution, controlling the temperature to 23-27 ℃, starting stirring, and stirring at a stirring speed of 80-120rpm for 28-30min to obtain egg orange clear liquid;
wherein the mass ratio of the catalyst to the mixed solution is 0.01.
2. The method for producing hydroxymethionine according to claim 1, wherein the slurry is prepared by adding formic acid and methionine into a reaction vessel and stirring for 28-32 min.
3. The method for producing hydroxymethionine according to claim 2, wherein the formic acid is present in an amount of 84-86% by mass; the mass fraction of the methionine is 97-99%; wherein the mass ratio of formic acid to methionine is 95-105.
4. The method for preparing hydroxymethionine according to claim 1, wherein sodium nitrite is added dropwise, the sodium nitrite solution is slowly added dropwise into the slurry at a speed of 0.5-1ml/min, the temperature of the four-mouth bottle during the dropwise addition process is controlled to be less than or equal to 35 ℃, and a mixed solution is obtained after the dropwise addition.
5. The method according to claim 4, wherein the mass fraction of the sodium nitrite solution is 33 to 37%; wherein the mass ratio of the sodium nitrite solution to the slurry is 15-16.
6. The method according to claim 1, wherein the catalyst is prepared by: uniformly mixing xanthan gum, succinic acid, methionine and polyethylene glycol 4000, placing the mixture in a closed reactor, vacuumizing the closed reactor until the vacuum degree is 0.02-0.03MPa, controlling the temperature of the closed reactor to be 40-45 ℃, standing the mixture in the closed reactor for 25-30min to obtain a primary catalyst, mixing the primary catalyst, sodium o-phenylphenol and phytic acid, performing ball milling, and after the ball milling is finished, placing the mixture at the temperature of-15 ℃ to-12 ℃ for freezing treatment for 18-22min to obtain the catalyst.
7. The method for preparing hydroxymethionine according to claim 6, wherein the mass ratio of xanthan gum, succinic acid, methionine to polyethylene glycol 4000 is 0.8-1.2.
8. The method for producing hydroxymethionine according to claim 6, wherein the mass ratio of the primary catalyst, sodium o-phenylphenol and phytic acid is 4.5 to 5.
9. The method for preparing hydroxymethionine according to claim 6, wherein the ball-to-material ratio in the ball milling is 10-12, the rotation speed is 300-320rpm, and the time is 30-35min.
10. Use of hydroxymethionine in an acidifying agent, characterized in that the use of hydroxymethionine obtained according to any one of claims 1 to 9 in an acidifying agent is used.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107628976A (en) * | 2017-09-27 | 2018-01-26 | 山东新和成氨基酸有限公司 | A kind of method of the methylmercapto butyric acid of 2 hydroxyl of continuous preparation 4 of cleaning |
| CN109912471A (en) * | 2019-04-02 | 2019-06-21 | 禄丰天宝磷化工有限公司 | A kind of method of continuous fast hydrolyzing 2- 2-hydroxy-4-methylthio butyronitrile synthetic methionine hydroxy analogs |
| CN112645857A (en) * | 2020-12-24 | 2021-04-13 | 浙江昂利泰制药有限公司 | Preparation method of racemic hydroxy methionine calcium |
-
2022
- 2022-08-19 CN CN202210999886.XA patent/CN115197110A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107628976A (en) * | 2017-09-27 | 2018-01-26 | 山东新和成氨基酸有限公司 | A kind of method of the methylmercapto butyric acid of 2 hydroxyl of continuous preparation 4 of cleaning |
| CN109912471A (en) * | 2019-04-02 | 2019-06-21 | 禄丰天宝磷化工有限公司 | A kind of method of continuous fast hydrolyzing 2- 2-hydroxy-4-methylthio butyronitrile synthetic methionine hydroxy analogs |
| CN112645857A (en) * | 2020-12-24 | 2021-04-13 | 浙江昂利泰制药有限公司 | Preparation method of racemic hydroxy methionine calcium |
Non-Patent Citations (4)
| Title |
|---|
| KLEEMANN, AXEL 等: "Enantioselective synthesis of the hydroxy analogs of D- and L-methionine", ANGEWANDTE CHEMIE, vol. 91, no. 10, pages 858 - 859 * |
| PATTI, ANGELA: "Biosynthetic relationship between sulfonium and N-methylated compounds in the red alga Vidalia volubilis", JOURNAL OF NATURAL PRODUCTS, vol. 55, no. 1, pages 53 - 57 * |
| 冯海涛: "蛋氨酸羟基类似物在饲料中的应用进展", 饲料与畜牧, pages 36 * |
| 徐宏斌 等: "羟基蛋氨酸及其钙盐的合成研究进展", 现代生物医学进展, pages 1388 * |
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