IL33840A - Process for the preparation of methionine - Google Patents
Process for the preparation of methionineInfo
- Publication number
- IL33840A IL33840A IL33840A IL3384070A IL33840A IL 33840 A IL33840 A IL 33840A IL 33840 A IL33840 A IL 33840A IL 3384070 A IL3384070 A IL 3384070A IL 33840 A IL33840 A IL 33840A
- Authority
- IL
- Israel
- Prior art keywords
- methionine
- alkali metal
- carbon dioxide
- mother liquor
- solution
- Prior art date
Links
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 title claims description 42
- 229930182817 methionine Natural products 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 46
- 239000001569 carbon dioxide Substances 0.000 claims description 23
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 23
- 239000012452 mother liquor Substances 0.000 claims description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- 238000006460 hydrolysis reaction Methods 0.000 claims description 17
- 230000007062 hydrolysis Effects 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- -1 alkali metal bicarbonate Chemical class 0.000 claims description 7
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 7
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 6
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 13
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 13
- 229940091173 hydantoin Drugs 0.000 description 13
- 239000000126 substance Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- GGLZPLKKBSSKCX-YFKPBYRVSA-N L-ethionine Chemical compound CCSCC[C@H](N)C(O)=O GGLZPLKKBSSKCX-YFKPBYRVSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical compound [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002741 methionine derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691906405 DE1906405C (de) | 1969-02-08 | Verfahren zur Herstellung von Methio mn |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL33840A0 IL33840A0 (en) | 1970-04-20 |
| IL33840A true IL33840A (en) | 1973-08-29 |
Family
ID=5724731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL33840A IL33840A (en) | 1969-02-08 | 1970-02-04 | Process for the preparation of methionine |
Country Status (13)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60344B2 (ja) * | 1979-01-25 | 1985-01-07 | 住友化学工業株式会社 | メチオニン合成排ガスから有効成分の回収方法 |
| EP0839804B1 (en) * | 1996-10-31 | 2002-01-09 | Sumitomo Chemical Company, Limited | Process for producing methionine |
| DE19846825A1 (de) † | 1998-10-10 | 2000-04-13 | Degussa | Rieselfähige Methionin-haltige Formlinge und Verfahren zu deren Herstellung |
| DE10160358A1 (de) * | 2001-12-08 | 2003-06-18 | Degussa | Verfahren zur Herstellung von Methionin |
| JP4997729B2 (ja) * | 2005-08-29 | 2012-08-08 | 住友化学株式会社 | メチオニンの製造方法 |
| WO2008006977A1 (fr) * | 2006-07-11 | 2008-01-17 | Adisseo France S.A.S. | Procédé de préparation du 2-hydroxy-4-(méthylthio)butyronitrile et de la méthionine |
| FR2903690B1 (fr) * | 2006-07-11 | 2008-11-14 | Adisseo Ireland Ltd | Procede de preparation de la methionine a partir d'acroleine sans isoler de produits intermediaires |
| JP2009292796A (ja) | 2008-06-09 | 2009-12-17 | Sumitomo Chemical Co Ltd | メチオニンの製造方法 |
| JP5307512B2 (ja) | 2008-11-07 | 2013-10-02 | 住友化学株式会社 | メチオニンの製造方法 |
| JP2010111640A (ja) | 2008-11-07 | 2010-05-20 | Sumitomo Chemical Co Ltd | メチオニンの製造方法 |
| FR2951195B1 (fr) | 2009-10-14 | 2014-01-31 | Roquette Freres | Composition riche en methionine destinee a l'alimentation animale |
| FR3035400B1 (fr) * | 2015-04-21 | 2017-04-07 | Adisseo France Sas | Procede de fabrication de methionine |
| CN116535338B (zh) * | 2023-04-25 | 2023-11-03 | 重庆渝化新材料有限责任公司 | 一种d,l-蛋氨酸生产过程中钾盐回收循环工艺 |
| CN116675631B (zh) * | 2023-06-07 | 2023-12-12 | 重庆渝化新材料有限责任公司 | 一种d,l-蛋氨酸的循环生产方法 |
-
1970
- 1970-02-03 CH CH148170A patent/CH529118A/de not_active IP Right Cessation
- 1970-02-03 BE BE745432D patent/BE745432A/xx not_active IP Right Cessation
- 1970-02-04 IL IL33840A patent/IL33840A/en unknown
- 1970-02-05 RO RO62373A patent/RO56492A/ro unknown
- 1970-02-06 SU SU1402139A patent/SU503509A3/ru active
- 1970-02-06 JP JP1056570A patent/JPS549174B1/ja active Pending
- 1970-02-06 AT AT113170A patent/AT295489B/de not_active IP Right Cessation
- 1970-02-06 NL NL707001725A patent/NL150435B/xx not_active IP Right Cessation
- 1970-02-06 FR FR7004281A patent/FR2032788A5/fr not_active Expired
- 1970-02-06 SE SE7001569A patent/SE373842B/xx unknown
- 1970-02-07 IT IT48405/70A patent/IT954084B/it active
- 1970-02-09 GB GB1296347D patent/GB1296347A/en not_active Expired
- 1970-02-09 HU HUDE708A patent/HU162233B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU503509A3 (ru) | 1976-02-15 |
| CH529118A (de) | 1972-10-15 |
| AT295489B (de) | 1972-01-10 |
| DE1906405A1 (de) | 1970-12-03 |
| GB1296347A (enrdf_load_stackoverflow) | 1972-11-15 |
| FR2032788A5 (enrdf_load_stackoverflow) | 1970-11-27 |
| HU162233B (enrdf_load_stackoverflow) | 1973-01-29 |
| RO56492A (enrdf_load_stackoverflow) | 1975-06-15 |
| SE373842B (enrdf_load_stackoverflow) | 1975-02-17 |
| IL33840A0 (en) | 1970-04-20 |
| BE745432A (fr) | 1970-07-16 |
| NL150435B (nl) | 1976-08-16 |
| NL7001725A (enrdf_load_stackoverflow) | 1970-08-11 |
| JPS549174B1 (enrdf_load_stackoverflow) | 1979-04-21 |
| IT954084B (it) | 1973-08-30 |
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