CN114853644A - Method for preparing acetyl methionine by using saponification liquid - Google Patents
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- CN114853644A CN114853644A CN202210475251.XA CN202210475251A CN114853644A CN 114853644 A CN114853644 A CN 114853644A CN 202210475251 A CN202210475251 A CN 202210475251A CN 114853644 A CN114853644 A CN 114853644A
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- acetylmethionine
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- 239000007788 liquid Substances 0.000 title claims abstract description 43
- XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 title claims abstract description 39
- 238000007127 saponification reaction Methods 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 74
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 33
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 33
- 235000011152 sodium sulphate Nutrition 0.000 claims description 33
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000000706 filtrate Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000007787 solid Substances 0.000 claims description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 14
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 11
- 239000012295 chemical reaction liquid Substances 0.000 claims description 11
- 239000000413 hydrolysate Substances 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- BTUDTSGOEFVJTD-WCCKRBBISA-N (2s)-2-amino-4-methylsulfanylbutanoic acid;sodium Chemical compound [Na].CSCC[C@H](N)C(O)=O BTUDTSGOEFVJTD-WCCKRBBISA-N 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 230000021736 acetylation Effects 0.000 claims description 7
- 238000006640 acetylation reaction Methods 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- SBKRXUMXMKBCLD-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)imidazolidine-2,4-dione Chemical compound CSCCC1NC(=O)NC1=O SBKRXUMXMKBCLD-UHFFFAOYSA-N 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 22
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 abstract description 11
- 229930182817 methionine Natural products 0.000 abstract description 11
- 239000002253 acid Substances 0.000 abstract description 8
- 239000002351 wastewater Substances 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 2
- 229910017053 inorganic salt Inorganic materials 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000012071 phase Substances 0.000 description 27
- 229960004452 methionine Drugs 0.000 description 10
- 235000006109 methionine Nutrition 0.000 description 10
- 238000003756 stirring Methods 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000004811 liquid chromatography Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 2
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 2
- XUYPXLNMDZIRQH-UHFFFAOYSA-N N-acetylmethionine Chemical compound CSCCC(C(O)=O)NC(C)=O XUYPXLNMDZIRQH-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000004470 DL Methionine Substances 0.000 description 1
- 229930195722 L-methionine Natural products 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the field of methionine production, and in particular relates to a method for preparing acetyl methionine by using saponification liquid. Compared with the prior art, the method adopts the saponification liquid as the raw material, realizes the thorough separation of the acetylmethionine and the inorganic salt under the condition of not introducing other substances, shortens the process flow, greatly reduces the production cost in the actual production, does not generate acid wastewater, is environment-friendly, obtains the byproduct acetic acid with the concentration of more than 95 percent, and has high utilization value.
Description
Technical Field
The invention relates to the field of methionine production, and in particular relates to a method for preparing acetyl methionine by using saponification liquid.
Background
The acetyl methionine is a medical intermediate and is widely used in related industries such as medicine, food, feed and the like. In addition, DL-acetylmethionine is also an intermediate product in the production of L-methionine.
At present, most of the methods for synthesizing DL-acetylmethionine in the market add solutions of commercial DL-methionine in NaOH and other similar bases, add acetic anhydride or acetyl chloride and the like for acetylation to obtain an acetylmethionine reaction solution, then add acid for neutralization, further concentrate and precipitate to obtain acetylmethionine and partial mother liquor, and the partial mother liquor can only be selected for application or discharge after treatment due to difficult complete separation. The acid is selected to be used indiscriminately, and the acid is accumulated along with the increase of times, so that the acid waste liquid cannot be discharged out completely. There is also a problem that a certain amount of acetic acid-containing wastewater is generated by condensation of the gas phase during the concentration. In summary, the current methods for producing acetylmethionine inevitably have several problems, namely, the commercial methionine is high in value and a large amount of alkali is consumed in the reaction process; secondly, a certain amount of acidic waste liquid is inevitably generated in the production process, thirdly, acetic acid-containing waste water is generated, the pressure on environmental protection is increased, and therefore, the production cost is increased.
According to the public patent (CN103342671A), saponification liquid is utilized to be directly acetylated to generate reaction liquid, after the reaction liquid is neutralized by adding acid, a part of acetylmethionine crystals are obtained by cooling and crystallizing, then, alkali is added into filtrate for concentration and desalination, then, acid is added, cooling and crystallizing are carried out to obtain the other part of acetylmethionine, and the rest filtrate is difficult to separate and is returned for reuse. The method uses saponification liquid for direct acetylation, reduces the amount of returned and used acidic mother liquid, greatly reduces the production cost, but does not completely solve the problems in the production of the acetylmethionine, and has the operations of repeatedly raising, lowering the temperature, adding alkali and then adding acid in the operation processes of separation, concentration and the like, so that the steps are complex, the resource waste is caused, and the production cost is increased.
Disclosure of Invention
In order to solve the problems mentioned in the background art, the invention aims to provide a method for preparing acetyl methionine by using saponification liquid, which adopts the saponification liquid as a raw material, directly separates the acetyl methionine from a sodium sulfate solution under the condition of not introducing other substances, shortens the process flow, does not generate acidic waste liquid or acetic acid-containing waste water, and greatly reduces the production cost.
On one hand, the method for preparing the acetyl methionine by using the saponification solution is characterized by comprising the following steps:
s1, performing acetylation treatment on a sodium hydrolysate of 5- (2-methylthioethyl) -hydantoin to obtain a reaction solution containing acetylmethionine;
s2, adding sodium sulfate into the reaction liquid, adjusting the pH value to be acidic, and layering to form an oil phase containing the acetyl methionine and a water phase containing the sodium sulfate;
s3, crystallizing and separating the oil phase into methionine solid and filtrate.
Preferably, the sodium hydrolysate in S1 consists of the following components in percentage by mass: 16.5-18.5% of sodium methionine, 10.5-12.5% of sodium carbonate and the balance of water.
Preferably, in S1: dropwise adding acetic anhydride into the sodium hydrolysate for acetylation at the reaction temperature of 30-45 ℃ for 2-4 h, wherein the reaction formula of sodium methionine and acetic anhydride in the saponified solution is as follows:
Reaction of
Preferably, in S2: sodium sulfate solid was added to the reaction solution, and after sodium sulfate was substantially saturated, the pH of the reaction solution was adjusted.
Preferably, in S2: adding concentrated sulfuric acid to acidify until the pH value is 2-4, keeping the temperature of the reaction liquid at 40 +/-5 ℃, and layering to form an oil phase and a water phase.
Preferably, in S3: cooling the oil phase to 20-25 ℃, and crystallizing and separating out solid acetylmethionine and filtrate.
On the other hand, the method for preparing the acetyl methionine by using the saponification liquid in a circulating way is characterized by comprising the following steps:
s1, performing acetylation treatment on a sodium hydrolysate of 5- (2-methylthioethyl) -hydantoin to obtain a reaction solution containing acetylmethionine;
s2, adding sodium sulfate into the reaction liquid, adjusting the pH value to be acidic, and layering to form an oil phase containing the acetyl methionine and a water phase containing the sodium sulfate;
s3, crystallizing and separating an oil phase into a methionine solid and a filtrate; and (3) carrying out negative pressure distillation on the filtrate, wherein the distillate is acetic acid with high concentration of over 95 percent, and the residual filtrate is directly returned to the oil phase. In actual production, the high-concentration acetic acid can be used for preparing ethyl acetate and the like, and the filtrate from which the acetic acid is removed is returned to the oil phase for reuse.
Preferably, in S2: and adding a sodium hydrolysate of S1 into the water phase to adjust the pH to 7-9, heating and concentrating, crystallizing and separating to obtain sodium sulfate and a sodium sulfate residual liquid, and returning the sodium sulfate residual liquid to S1 to be combined with the sodium hydrolysate. In the actual production, because the water phase contains sulfuric acid and has lower pH, direct evaporation has strong corrosion effect on equipment, acetic acid-containing wastewater is generated, and the pH value is adjusted by using saponification liquid under the condition of not introducing other substances, so that the use of alkali for neutralization is avoided, the cost is reduced, and a small amount of acetyl dissolved in the water phase is recycled.
Has the advantages that: compared with the prior art, the method for preparing the acetyl methionine by using the saponification liquid disclosed by the invention has the advantages that the acetyl methionine and the inorganic salt are thoroughly separated without introducing other substances, the process flow is shortened, the production cost is greatly reduced in the actual production, no acidic wastewater is generated, the environment is friendly, the concentration of the obtained byproduct acetic acid is high, and the utilization value is high.
Drawings
FIG. 1 is a process flow diagram of the present invention.
Detailed Description
The present invention is described in detail below with reference to specific examples, which are given for the purpose of further illustrating the invention and are not to be construed as limiting the scope of the invention, and the invention may be modified and adapted by those skilled in the art in light of the above disclosure. Except for special description, the parts are parts by weight, the percentages are mass percentages, and the concentration is mass percentage concentration.
Example 1
Taking 50kg of saponification liquid in a production workshop, and analyzing the composition of the saponification liquid: the mass fraction of the sodium methionine is 17.2%; 11.8 percent of sodium carbonate by mass; the balance of water. Dripping 6.95kg of acetic anhydride in a water bath at 40 ℃, reacting for 4 hours at constant temperature, sampling, and detecting by using liquid chromatography, wherein the conversion rate of methionine is 99.6%.
Example 2
Taking 100kg of saponification liquid in a production workshop, and analyzing the composition of the saponification liquid: the mass fraction of the sodium methionine is 17.5 percent; 11.3 percent of sodium carbonate by mass; the balance of water. Dripping 13.9kg of acetic anhydride in a water bath at 40 ℃, reacting for 4 hours at a constant temperature, sampling, and detecting by using liquid chromatography, wherein the conversion rate of methionine is 99.6%; then adding 10kg of sodium sulfate solid into the reaction liquid, adding concentrated sulfuric acid while stirring to enable the pH value to be 2-4, stopping stirring, standing for 3-5 minutes, and respectively extracting an oil phase and a water phase; cooling the oil phase to 20-25 ℃ for crystallization, filtering to obtain 16.2kg of an acetylmethionine solid crude product and filtrate, adding the filtrate into a distillation device, starting to heat, controlling the temperature to be 50-70 ℃, adjusting the vacuum degree to be 0.04-0.06 MPa, condensing and collecting evaporated acetic acid gas to obtain 6.8kg of acetic acid, wherein the mass fraction of the acetic acid is 96.4%, and the residual filtrate is reserved; and adding the aqueous phase into a saponification solution to adjust the pH value to 7-9, adding the aqueous phase into a concentration device, starting heating, controlling the temperature to be more than 70 ℃, adjusting the vacuum degree to be more than 0.07Mpa, concentrating to obtain sodium sulfate to obtain 17.1kg of solid sodium sulfate, and separating sodium sulfate residual liquid for later use.
The following provides a specific example of production practice using the technical scheme provided by the invention, and practical operation is performed in sequence, so that the process of industrial continuous production using the method is simulated.
Example 3-1
Taking 100kg of saponification liquid in a production workshop, and analyzing the composition of the saponification liquid: the mass fraction of the sodium methionine is 17.9%; 11.8 percent of sodium carbonate by mass; the balance of water. Adding all the sodium sulfate residual liquid described in example 2 into the saponified solution, dropwise adding 15kg of acetic anhydride at 40 ℃ in a water bath, reacting for 4 hours at constant temperature, sampling, and detecting by using liquid chromatography, wherein the conversion rate of methionine is 99.5%. Then adding 10kg of sodium sulfate solid into the reaction liquid, adding concentrated sulfuric acid while stirring to enable the pH value to be 2-4, stopping stirring, standing for 3-5 minutes, and respectively extracting an oil phase and a water phase; adding the residual filtrate obtained in the step 2 after acetic acid evaporation into an oil phase, cooling to 20-25 ℃ for crystallization, filtering to obtain 19.1kg of acetylmethionine, adding the obtained filtrate into a distillation device, starting to heat, controlling the temperature to be 50-70 ℃, adjusting the vacuum degree to be 0.04-0.06 MPa, condensing and collecting evaporated acetic acid gas to obtain 6.7kg of acetic acid, wherein the mass fraction of the acetic acid is 95.8%. The remaining filtrate is ready for use. And adding the aqueous phase into the saponification liquid to adjust the pH value to be 7-9, adding the saponification liquid into a concentration device, starting heating, controlling the temperature to be more than 70 ℃, adjusting the vacuum degree to be more than 0.07Mpa, concentrating to obtain sodium sulfate to obtain 17.1kg of solid sodium sulfate, and keeping the residual mother liquid for later use.
Examples 3 to 2
Taking 100kg of saponification liquid in a production workshop, and analyzing the composition of the saponification liquid: the mass fraction of the sodium methionine is 17.8%; 11.8 percent of sodium carbonate by mass; the balance of water. Adding all the sodium sulfate residual liquid described in example 3-1 into the saponified solution, dropwise adding 15kg of acetic anhydride at 40 ℃ in a water bath, reacting for 4 hours at constant temperature, sampling, and detecting by using liquid chromatography, wherein the conversion rate of methionine is 99.6%. Then adding 10kg of sodium sulfate solid into the reaction liquid, adding concentrated sulfuric acid while stirring to enable the pH value to be 2-4, stopping stirring, standing for 3-5 minutes, and respectively extracting an oil phase and a water phase; then adding the residual filtrate after the acetic acid is removed in the example 3-1 into an oil phase, cooling to 20-25 ℃ for crystallization, filtering to obtain 19.5kg of acetyl methionine, adding the obtained filtrate into a distillation device, starting to heat, controlling the temperature to be 50-70 ℃, adjusting the vacuum degree to be 0.04-0.06 MPa, condensing and collecting the evaporated acetic acid gas to obtain 7.0kg of acetic acid, wherein the mass fraction of the acetic acid is 96.7%. The remaining filtrate is ready for use. And adding the aqueous phase into the saponification liquid to adjust the pH value to be 7-9, adding the saponification liquid into a concentration device, starting heating, controlling the temperature to be more than 70 ℃, adjusting the vacuum degree to be more than 0.07Mpa, concentrating to obtain sodium sulfate to obtain 17.7kg of solid sodium sulfate, and keeping the residual mother liquid for later use.
Examples 3 to 3
Taking 100kg of saponification liquid in a production workshop, and analyzing the composition of the saponification liquid: the mass fraction of the sodium methionine is 18.1 percent; the mass fraction of sodium carbonate is 12.0 percent; the balance of water. And (3) completely adding the sodium sulfate residual liquid described in the example 3-2 into the saponified liquid, dropwise adding 15kg of acetic anhydride at the temperature of 40 ℃ in a water bath, reacting for 4 hours at constant temperature, sampling, and detecting by using liquid chromatography, wherein the conversion rate of methionine is 99.5%. Then adding 10kg of sodium sulfate solid into the reaction liquid, adding concentrated sulfuric acid while stirring to enable the pH value to be 2-4, stopping stirring, standing for 3-5 minutes, and respectively extracting an oil phase and a water phase; adding the residual filtrate obtained by distilling off the acetic acid in the example 3-2 into an oil phase, cooling to 20-25 ℃ for crystallization, filtering to obtain 19.6kg of acetylmethionine, adding the obtained filtrate into a distillation device, starting to heat, controlling the temperature to be 50-70 ℃, adjusting the vacuum degree to be 0.04-0.06 MPa, condensing and collecting the distilled acetic acid gas to obtain 6.6kg of acetic acid, wherein the mass fraction of the acetic acid is 95.2%, and the residual filtrate is reserved. And adding the aqueous phase into a saponification solution to adjust the pH value to 7-9, adding the aqueous phase into a concentration device, starting heating, controlling the temperature to be more than 70 ℃, adjusting the vacuum degree to be more than 0.07Mpa, concentrating to obtain sodium sulfate to obtain 18.1kg of solid sodium sulfate, and keeping the residual mother liquor for later use.
Finally, the above embodiments are only for illustrating the technical solutions of the present invention and not for limiting, although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions may be made to the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention, and all of them should be covered in the claims of the present invention.
Claims (8)
1. A method for preparing acetyl methionine by using saponification liquid is characterized by comprising the following steps:
s1, performing acetylation treatment on a sodium hydrolysate of 5- (2-methylthioethyl) -hydantoin to obtain a reaction solution containing acetylmethionine;
s2, adding sodium sulfate into the reaction liquid, adjusting the pH value to be acidic, and layering to form an oil phase containing the acetyl methionine and a water phase containing the sodium sulfate;
s3, crystallizing and separating the oil phase into an acetylmethionine solid and a filtrate.
2. The method for preparing acetylmethionine using saponification solution as claimed in claim 1, wherein the sodium hydrolysate of S1 comprises the following components in percentage by mass: 16.5-18.5% of sodium methionine, 10.5-12.5% of sodium carbonate and the balance of water.
3. The method for preparing acetylmethionine using saponification solution as claimed in claim 1, wherein in S1: and dropwise adding acetic anhydride into the sodium hydrolysate for acetylation, wherein the reaction temperature is 30-45 ℃, and the reaction time is 2-4 h.
4. The method for preparing acetylmethionine using saponification solution as claimed in claim 1, wherein in S2: sodium sulfate solid was added to the reaction solution, and the pH of the reaction solution was adjusted until sodium sulfate was substantially saturated.
5. The method for preparing acetylmethionine using saponification solution as claimed in claim 1, wherein in S2: adding concentrated sulfuric acid to acidify until the pH value is 2-4, keeping the temperature of the reaction liquid at 40 +/-5 ℃, and layering to form an oil phase and a water phase.
6. The method for preparing acetylmethionine using saponification solution as claimed in claim 1, wherein in S3: cooling the oil phase to 20-25 ℃, and crystallizing and separating out solid acetylmethionine and filtrate.
7. A method for preparing acetyl methionine by using saponification liquid circulation is characterized in that: comprising the process according to any one of claims 1 to 6, and subjecting the filtrate of S3 to negative pressure distillation to obtain a distillate containing acetic acid with a concentration of 95% or more, and returning the remaining filtrate directly to the oil phase.
8. The method for preparing acetylmethionine using saponification solution cycle as claimed in claim 7, wherein: and adding a sodium hydrolysate of S1 into the water phase of the S2 to adjust the pH value to 7-9, heating, concentrating, crystallizing and separating to obtain sodium sulfate and sodium sulfate residual liquid, and returning the sodium sulfate residual liquid to S1 to be combined with the sodium hydrolysate.
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|---|---|---|---|---|
| US6114163A (en) * | 1995-12-13 | 2000-09-05 | Degussa Aktiengesellschaft | Process for obtaining active L-α-amino carboxylic acids from corresponding racemic d, L-α-amino carboxylic acids |
| CN103342671A (en) * | 2013-07-24 | 2013-10-09 | 重庆紫光化工股份有限公司 | Method for preparing L-methionine by using acetylated saponification solution |
| CN103408474A (en) * | 2013-08-28 | 2013-11-27 | 重庆紫光化工股份有限公司 | Efficient production method of high-purity N-acetyl-D, L-methionine |
| CN106380433A (en) * | 2016-08-26 | 2017-02-08 | 宁夏紫光天化蛋氨酸有限责任公司 | Separation and purification method for N-acetyl-D, L-methionine |
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2022
- 2022-04-29 CN CN202210475251.XA patent/CN114853644A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6114163A (en) * | 1995-12-13 | 2000-09-05 | Degussa Aktiengesellschaft | Process for obtaining active L-α-amino carboxylic acids from corresponding racemic d, L-α-amino carboxylic acids |
| CN103342671A (en) * | 2013-07-24 | 2013-10-09 | 重庆紫光化工股份有限公司 | Method for preparing L-methionine by using acetylated saponification solution |
| CN103408474A (en) * | 2013-08-28 | 2013-11-27 | 重庆紫光化工股份有限公司 | Efficient production method of high-purity N-acetyl-D, L-methionine |
| CN106380433A (en) * | 2016-08-26 | 2017-02-08 | 宁夏紫光天化蛋氨酸有限责任公司 | Separation and purification method for N-acetyl-D, L-methionine |
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