JP2020519574A - メチオニンの製造方法 - Google Patents
メチオニンの製造方法 Download PDFInfo
- Publication number
- JP2020519574A JP2020519574A JP2019559812A JP2019559812A JP2020519574A JP 2020519574 A JP2020519574 A JP 2020519574A JP 2019559812 A JP2019559812 A JP 2019559812A JP 2019559812 A JP2019559812 A JP 2019559812A JP 2020519574 A JP2020519574 A JP 2020519574A
- Authority
- JP
- Japan
- Prior art keywords
- methionine
- potassium
- alkali metal
- process solution
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229930182817 methionine Natural products 0.000 title claims description 47
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 title claims description 45
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 claims abstract description 54
- 239000011734 sodium Substances 0.000 claims abstract description 50
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 29
- 239000011591 potassium Substances 0.000 claims abstract description 27
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 27
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 26
- 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 abstract description 24
- SBKRXUMXMKBCLD-SCSAIBSYSA-N (R)-5-[2-(methylthio)ethyl]hydantoin Chemical compound CSCC[C@H]1NC(=O)NC1=O SBKRXUMXMKBCLD-SCSAIBSYSA-N 0.000 claims abstract description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 14
- -1 alkali metal hydrogen carbonate Chemical class 0.000 claims abstract description 14
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 8
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims abstract description 7
- SBKRXUMXMKBCLD-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)imidazolidine-2,4-dione Chemical compound CSCCC1NC(=O)NC1=O SBKRXUMXMKBCLD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims abstract description 4
- 150000008041 alkali metal carbonates Chemical class 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 54
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 24
- 238000010926 purge Methods 0.000 claims description 14
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 12
- 239000001569 carbon dioxide Substances 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 abstract description 2
- 229960004452 methionine Drugs 0.000 description 39
- 229960003975 potassium Drugs 0.000 description 23
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- 230000007062 hydrolysis Effects 0.000 description 10
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 9
- 229940091173 hydantoin Drugs 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 239000012065 filter cake Substances 0.000 description 7
- 108010085203 methionylmethionine Proteins 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 6
- ZYTPOUNUXRBYGW-UHFFFAOYSA-N methionyl-methionine Chemical compound CSCCC(N)C(=O)NC(C(O)=O)CCSC ZYTPOUNUXRBYGW-UHFFFAOYSA-N 0.000 description 6
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 description 4
- 239000011736 potassium bicarbonate Substances 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 159000000001 potassium salts Chemical class 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000975 co-precipitation Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 238000009533 lab test Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 2
- IREPZTZSVPKCAR-WCCKRBBISA-M sodium;(2s)-2-amino-4-methylsulfanylbutanoate Chemical compound [Na+].CSCC[C@H](N)C([O-])=O IREPZTZSVPKCAR-WCCKRBBISA-M 0.000 description 2
- QHMWJBZUZWPWFB-WCCKRBBISA-N (2s)-2-amino-4-methylsulfanylbutanoic acid;potassium Chemical compound [K].CSCC[C@H](N)C(O)=O QHMWJBZUZWPWFB-WCCKRBBISA-N 0.000 description 1
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 125000000393 L-methionino group Chemical group [H]OC(=O)[C@@]([H])(N([H])[*])C([H])([H])C(SC([H])([H])[H])([H])[H] 0.000 description 1
- ZYTPOUNUXRBYGW-YUMQZZPRSA-N Met-Met Chemical compound CSCC[C@H]([NH3+])C(=O)N[C@H](C([O-])=O)CCSC ZYTPOUNUXRBYGW-YUMQZZPRSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000007059 Strecker synthesis reaction Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- JSXPCVUETJIQHE-UHFFFAOYSA-L dipotassium;methanedisulfonate Chemical compound [K+].[K+].[O-]S(=O)(=O)CS([O-])(=O)=O JSXPCVUETJIQHE-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000001863 plant nutrition Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Images
Classifications
-
- 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
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05C—NITROGENOUS FERTILISERS
- C05C11/00—Other nitrogenous fertilisers
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05D—INORGANIC FERTILISERS NOT COVERED BY SUBCLASSES C05B, C05C; FERTILISERS PRODUCING CARBON DIOXIDE
- C05D1/00—Fertilisers containing potassium
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05D—INORGANIC FERTILISERS NOT COVERED BY SUBCLASSES C05B, C05C; FERTILISERS PRODUCING CARBON DIOXIDE
- C05D9/00—Other inorganic fertilisers
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05F—ORGANIC FERTILISERS NOT COVERED BY SUBCLASSES C05B, C05C, e.g. FERTILISERS FROM WASTE OR REFUSE
- C05F11/00—Other organic fertilisers
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
KHCO3の溶解度:
Seidell,1940:Seidel,A.;Solubility Data Ser.,1940
Gmelin:Gmelins Handbuch,22,1938
Takahashi,1927:Takahashi,G.;Bull.Imp.Seric.Stn.Tokyo 29,1927,165
NaHCO3の溶解度:
Trypuc & Kielkowska,1998:Trypuc,M.;Kielkowska,U.;J.Chem.Eng.Data 43(2),1998,201−204
Fedotev,1904:Fedotev,P.P.,Z.Phys.Chem.49,1904,168
メチオニンの溶解度:
Fuchs et al.,2006:Fuchs et al.,2006,Ind.Eng.Chem.Res.,45,6578−6584
(Fuchs et al.,2006に従った)実験室実験:独自の実験室実験の結果
炭酸化反応では、0.5当量の炭酸カリウムを伴うメチオニンのカリウム塩(K−Met)をCO2と反応させる。KHCO3が形成され、メチオニン(H−Met)が沈殿する(化学反応式1および2):
K−Met+CO2+H2O→H−Met(s)+KHCO3 (化学反応式1)
K2CO3+CO2+H2O→2KHCO3 (化学反応式2)
モル比K/Naが90/10のプロセス溶液を製造するための実験手順
1000mlのビーカーを氷浴に入れ、KOH(水中40%、354.2g、2.53mol)、NaOH(水中40%、11.2g、0.28mol)、D,L−メチオニン(159.7g、1.07mol)、DL−メチオニル−DL−メチオニン(29.9g、0.11mol)およびギ酸(水中50%、41.4g、0.45mol)を200mlの脱イオン水に溶解し、45分間撹拌した。次いで、この溶液を20℃に加温し、1000mlのメスフラスコに移し、脱イオン水で1000mlの総容量に満たした。
Claims (6)
- メチオニンの製造方法であって、アルカリ金属水酸化物および/またはアルカリ金属炭酸塩および/またはアルカリ金属炭酸水素塩を含む水性プロセス溶液中で5−(2−メチルメルカプトエチル)−ヒダントイン(メチオニンヒダントイン)をアルカリ加水分解してメチオニンアルカリ金属塩を形成し、二酸化炭素によりメチオニンを沈殿させ、沈殿させたメチオニンを前記プロセス溶液から分離し、前記プロセス溶液を濃縮し、前記プロセス溶液に再び送られるメチオニンヒダントインの前記アルカリ加水分解において前記プロセス溶液を再利用することを含み、ここで、前記プロセス溶液中のアルカリ金属カチオンは、99/1〜20/80の範囲のK/Naモル比を有するカリウムおよびナトリウムである、方法。
- 前記プロセス溶液中の前記K/Naモル比が90/10〜20/80の範囲である、請求項1記載の方法。
- 前記プロセス溶液中の前記K/Naモル比が70/30〜50/50の範囲である、請求項1または2記載の方法。
- 前記沈殿させたメチオニンを水溶液から再結晶し、ろ過して乾燥させ、そのようにして得られた結晶性メチオニンは、99%を超える純度ならびに0.3%未満のカリウム含有量および0.1%未満のナトリウム含有量を有する、請求項1から3までのいずれか1項記載の方法。
- 前記結晶性メチオニン中の前記カリウム含有量が0.05〜0.3%の範囲であり、前記ナトリウム含有量が0.01〜0.1%の範囲である、請求項4記載の方法。
- 前記プロセス溶液の一部であるパージ溶液をプロセスから連続的に除去し、新鮮なアルカリ金属水酸化物溶液と交換する、請求項1から5までのいずれか1項記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP17171060.1 | 2017-05-15 | ||
EP17171060.1A EP3404018A1 (en) | 2017-05-15 | 2017-05-15 | Process for preparing methionine |
EP17182515.1A EP3431465A1 (en) | 2017-07-21 | 2017-07-21 | Process for preparing methionine |
EP17182515.1 | 2017-07-21 | ||
PCT/EP2018/061799 WO2018210615A1 (en) | 2017-05-15 | 2018-05-08 | Process for preparing methionine |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2020519574A true JP2020519574A (ja) | 2020-07-02 |
JP7431581B2 JP7431581B2 (ja) | 2024-02-15 |
Family
ID=62091905
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2019559812A Active JP7431581B2 (ja) | 2017-05-15 | 2018-05-08 | メチオニンの製造方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US10919848B2 (ja) |
EP (1) | EP3625211B1 (ja) |
JP (1) | JP7431581B2 (ja) |
CN (1) | CN110678446B (ja) |
SG (1) | SG11201909687QA (ja) |
WO (1) | WO2018210615A1 (ja) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4069251A (en) * | 1969-02-08 | 1978-01-17 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Continuous process for the manufacture of methionine |
JPS6092258A (ja) * | 1983-09-29 | 1985-05-23 | デグツサ・アクチエンゲゼルシヤフト | 5‐(β‐メチルメルカプトエチル)‐ヒダントインの加水分解方法 |
JPH09176111A (ja) * | 1995-12-18 | 1997-07-08 | Degussa Ag | メチオニンおよびその塩の製造方法 |
JP2004175716A (ja) * | 2002-11-27 | 2004-06-24 | Nippon Soda Co Ltd | メチオニンの晶析方法 |
JP2005511733A (ja) * | 2001-12-08 | 2005-04-28 | デグサ アクチエンゲゼルシャフト | メチオニンの製造方法 |
JP2015515458A (ja) * | 2012-03-20 | 2015-05-28 | エボニック インダストリーズ アクチエンゲゼルシャフトEvonik Industries AG | メチオニンの製造方法 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4259525A (en) | 1979-10-01 | 1981-03-31 | Diamond Shamrock Corporation | Methionine process |
US4272631A (en) | 1980-02-25 | 1981-06-09 | Diamond Shamrock Corporation | Hydrolysis of 5-(beta-methylmercaptoethyl)-hydantoin |
DE3104997A1 (de) * | 1981-02-12 | 1982-08-26 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung von waessrigen natriummethioninat-loesungen (a) |
EP0839804B1 (en) * | 1996-10-31 | 2002-01-09 | Sumitomo Chemical Company, Limited | Process for producing methionine |
DE19822099A1 (de) * | 1998-05-16 | 1999-11-18 | Degussa | Verfahren zur Herstellung von wäßrigen Natriummethioninat-Lösungen und Verwendung dieser Lösungen zur Herstellung eines Granulats |
WO2003045904A1 (fr) * | 2001-11-29 | 2003-06-05 | Nippon Soda Co.,Ltd. | Procede de production de methionine |
ATE509908T1 (de) | 2004-02-14 | 2011-06-15 | Evonik Degussa Gmbh | Verfahren zur herstellung von methionin |
JP2009292796A (ja) * | 2008-06-09 | 2009-12-17 | Sumitomo Chemical Co Ltd | メチオニンの製造方法 |
MY171361A (en) | 2011-08-30 | 2019-10-10 | Evonik Operations Gmbh | Method for producing a methionine salt |
FR3035400B1 (fr) | 2015-04-21 | 2017-04-07 | Adisseo France Sas | Procede de fabrication de methionine |
CN106432018A (zh) * | 2016-09-14 | 2017-02-22 | 宁夏紫光天化蛋氨酸有限责任公司 | 一种d,l‑蛋氨酸的环保清洁生产方法 |
CN106432020B (zh) * | 2016-09-14 | 2018-11-20 | 宁夏紫光天化蛋氨酸有限责任公司 | 一种d,l-蛋氨酸的分离纯化方法 |
-
2018
- 2018-05-08 JP JP2019559812A patent/JP7431581B2/ja active Active
- 2018-05-08 CN CN201880028831.6A patent/CN110678446B/zh active Active
- 2018-05-08 SG SG11201909687Q patent/SG11201909687QA/en unknown
- 2018-05-08 US US16/605,075 patent/US10919848B2/en active Active
- 2018-05-08 EP EP18721400.2A patent/EP3625211B1/en active Active
- 2018-05-08 WO PCT/EP2018/061799 patent/WO2018210615A1/en unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4069251A (en) * | 1969-02-08 | 1978-01-17 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Continuous process for the manufacture of methionine |
JPS6092258A (ja) * | 1983-09-29 | 1985-05-23 | デグツサ・アクチエンゲゼルシヤフト | 5‐(β‐メチルメルカプトエチル)‐ヒダントインの加水分解方法 |
JPH09176111A (ja) * | 1995-12-18 | 1997-07-08 | Degussa Ag | メチオニンおよびその塩の製造方法 |
JP2005511733A (ja) * | 2001-12-08 | 2005-04-28 | デグサ アクチエンゲゼルシャフト | メチオニンの製造方法 |
JP2004175716A (ja) * | 2002-11-27 | 2004-06-24 | Nippon Soda Co Ltd | メチオニンの晶析方法 |
JP2015515458A (ja) * | 2012-03-20 | 2015-05-28 | エボニック インダストリーズ アクチエンゲゼルシャフトEvonik Industries AG | メチオニンの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
WO2018210615A1 (en) | 2018-11-22 |
SG11201909687QA (en) | 2019-11-28 |
EP3625211A1 (en) | 2020-03-25 |
CN110678446A (zh) | 2020-01-10 |
US10919848B2 (en) | 2021-02-16 |
EP3625211B1 (en) | 2021-03-17 |
US20200039928A1 (en) | 2020-02-06 |
CN110678446B (zh) | 2021-11-26 |
JP7431581B2 (ja) | 2024-02-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7671234B2 (en) | Method for producing methylglycine-N,N-diethanoic acid-trialkali metal salts with a low by-product content | |
US9994517B1 (en) | Method for preparing taurine | |
US9850200B1 (en) | Method for preparing taurine | |
US8119837B2 (en) | Process for producing methionine | |
JP4338524B2 (ja) | メチオニンの製造方法 | |
US11578036B2 (en) | Cyclic process for producing taurine from monoethanolamine | |
JP7431581B2 (ja) | メチオニンの製造方法 | |
JP2003176261A (ja) | アミノアセトニトリルおよびグリシン誘導体の製造方法 | |
EP3431465A1 (en) | Process for preparing methionine | |
EP3404018A1 (en) | Process for preparing methionine | |
US20200188834A1 (en) | Recovered-carbon-dioxide purifying method and methionine manufacturing method including recovered-carbon-dioxide purifying step | |
US20200347015A1 (en) | Method for producing methionine | |
CN111757867B (zh) | 蛋氨酸及其羟基类似物的甲酯的去甲基化 | |
US11180447B2 (en) | Method for producing methionine | |
US20230104350A1 (en) | Process sulfonation of aminoethylene sulfonic ester with carbon dioxide addition to produce taurine | |
JPH10306071A (ja) | 粒状dl−メチオニン結晶およびその製造方法 | |
JP2716467B2 (ja) | グリシンの製造方法 | |
US2889347A (en) | Process for producing alkali metal methyl arsonates | |
JP2801781B2 (ja) | グリシンの製造方法 | |
WO2021195001A1 (en) | Process sulfonation to produce taurine | |
WO2023067061A1 (en) | Precursors for the preparation of dl-methionine and dlld-methionylmethionine | |
JPH01193245A (ja) | S−カルボキシメチル−l−システインの製造法 | |
JP2011195517A (ja) | メチオニンの製造方法 | |
WO2021108179A1 (en) | Process sulfonation of aminoethylene sulfonic ester to produce taurine | |
JPH03193748A (ja) | グリシンの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20210419 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20211029 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20211108 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20220420 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20220817 |
|
C60 | Trial request (containing other claim documents, opposition documents) |
Free format text: JAPANESE INTERMEDIATE CODE: C60 Effective date: 20220817 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20220825 |
|
C21 | Notice of transfer of a case for reconsideration by examiners before appeal proceedings |
Free format text: JAPANESE INTERMEDIATE CODE: C21 Effective date: 20220830 |
|
A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20221028 |
|
C211 | Notice of termination of reconsideration by examiners before appeal proceedings |
Free format text: JAPANESE INTERMEDIATE CODE: C211 Effective date: 20221108 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20240202 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7431581 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |