AU717705B2 - Method for the isolation of 2-hydroxy-4-methylthiobutyric acid (MHA) - Google Patents
Method for the isolation of 2-hydroxy-4-methylthiobutyric acid (MHA) Download PDFInfo
- Publication number
- AU717705B2 AU717705B2 AU11906/97A AU1190697A AU717705B2 AU 717705 B2 AU717705 B2 AU 717705B2 AU 11906/97 A AU11906/97 A AU 11906/97A AU 1190697 A AU1190697 A AU 1190697A AU 717705 B2 AU717705 B2 AU 717705B2
- Authority
- AU
- Australia
- Prior art keywords
- mha
- extraction
- liquid
- salt
- water
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 96
- 238000002955 isolation Methods 0.000 title claims description 19
- PICCHNWCTUUCAQ-UHFFFAOYSA-N 2-hydroxypentanethioic s-acid Chemical compound CCCC(O)C(O)=S PICCHNWCTUUCAQ-UHFFFAOYSA-N 0.000 title claims description 10
- 238000000605 extraction Methods 0.000 claims description 139
- 150000003839 salts Chemical class 0.000 claims description 114
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 89
- 239000002904 solvent Substances 0.000 claims description 79
- 239000007788 liquid Substances 0.000 claims description 66
- 238000001704 evaporation Methods 0.000 claims description 65
- 230000008020 evaporation Effects 0.000 claims description 62
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 58
- 239000007791 liquid phase Substances 0.000 claims description 53
- 235000011149 sulphuric acid Nutrition 0.000 claims description 52
- 239000001117 sulphuric acid Substances 0.000 claims description 50
- 238000006460 hydrolysis reaction Methods 0.000 claims description 47
- 230000007062 hydrolysis Effects 0.000 claims description 39
- 239000012141 concentrate Substances 0.000 claims description 29
- 239000012071 phase Substances 0.000 claims description 28
- 239000011541 reaction mixture Substances 0.000 claims description 28
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 claims description 26
- 239000003960 organic solvent Substances 0.000 claims description 24
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 22
- -1 MHA amide Chemical class 0.000 claims description 21
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 21
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 17
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 17
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 17
- 239000000470 constituent Substances 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 9
- 150000003863 ammonium salts Chemical class 0.000 claims description 7
- 150000002170 ethers Chemical class 0.000 claims description 6
- 239000013557 residual solvent Substances 0.000 claims description 3
- 238000005185 salting out Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 79
- 239000000413 hydrolysate Substances 0.000 description 48
- 239000000203 mixture Substances 0.000 description 46
- 239000000047 product Substances 0.000 description 27
- 238000002474 experimental method Methods 0.000 description 25
- 238000011084 recovery Methods 0.000 description 24
- 239000000706 filtrate Substances 0.000 description 19
- 238000000926 separation method Methods 0.000 description 19
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 18
- 150000001408 amides Chemical class 0.000 description 17
- 239000008346 aqueous phase Substances 0.000 description 17
- 238000009833 condensation Methods 0.000 description 17
- 230000005494 condensation Effects 0.000 description 17
- 239000001166 ammonium sulphate Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 239000000539 dimer Substances 0.000 description 13
- 229930182817 methionine Natural products 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 239000012266 salt solution Substances 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 10
- 238000005191 phase separation Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000003247 decreasing effect Effects 0.000 description 8
- 238000010586 diagram Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 238000007127 saponification reaction Methods 0.000 description 8
- 229910021653 sulphate ion Inorganic materials 0.000 description 8
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
- 230000003750 conditioning effect Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000000654 additive Substances 0.000 description 6
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000002485 combustion reaction Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000002351 wastewater Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000001256 steam distillation Methods 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- VWWOJJANXYSACS-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanenitrile Chemical compound CSCCC(O)C#N VWWOJJANXYSACS-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000019728 animal nutrition Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000011552 falling film Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000000050 nutritive effect Effects 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000010414 supernatant solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000003685 thermal hair damage Effects 0.000 description 2
- 230000008646 thermal stress Effects 0.000 description 2
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 1
- ONFOSYPQQXJWGS-UHFFFAOYSA-N 2-hydroxy-4-(methylthio)butanoic acid Chemical compound CSCCC(O)C(O)=O ONFOSYPQQXJWGS-UHFFFAOYSA-N 0.000 description 1
- DOLNLDKZJKDWLS-UHFFFAOYSA-N 2-hydroxypentanethioamide Chemical compound CCCC(O)C(N)=S DOLNLDKZJKDWLS-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- 101001041669 Oryctolagus cuniculus Corticostatin 1 Proteins 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000567 combustion gas Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000006052 feed supplement Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 150000003568 thioethers Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
-
- 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
- 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
- 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
- C07C323/52—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 acyclic and saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Power Steering Mechanism (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19548538A DE19548538C2 (de) | 1995-12-23 | 1995-12-23 | Verfahren zur Gewinnung von 2-Hydroxy-4-methylthiobuttersäure (MHA) |
| DE19548538 | 1995-12-23 | ||
| PCT/EP1996/005437 WO1997023452A1 (de) | 1995-12-23 | 1996-12-05 | Verfahren zur gewinnung von 2-hydroxy-4-methylthiobuttersäure (mha) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1190697A AU1190697A (en) | 1997-07-17 |
| AU717705B2 true AU717705B2 (en) | 2000-03-30 |
Family
ID=7781282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU11906/97A Ceased AU717705B2 (en) | 1995-12-23 | 1996-12-05 | Method for the isolation of 2-hydroxy-4-methylthiobutyric acid (MHA) |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6140536A (ref) |
| EP (1) | EP0874811B1 (ref) |
| JP (1) | JP3962089B2 (ref) |
| KR (1) | KR100460364B1 (ref) |
| CN (1) | CN1067377C (ref) |
| AU (1) | AU717705B2 (ref) |
| BR (1) | BR9612235A (ref) |
| DE (2) | DE19548538C2 (ref) |
| ES (1) | ES2160264T3 (ref) |
| ID (1) | ID16007A (ref) |
| IN (1) | IN190919B (ref) |
| MX (1) | MX9804881A (ref) |
| MY (1) | MY117493A (ref) |
| RU (1) | RU2160730C2 (ref) |
| TR (1) | TR199801190T2 (ref) |
| TW (1) | TW371655B (ref) |
| WO (1) | WO1997023452A1 (ref) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6814988B2 (en) | 1997-07-25 | 2004-11-09 | Novus International, Inc. | Process for optimizing milk production |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3942715B2 (ja) | 1998-01-06 | 2007-07-11 | パイオニア株式会社 | 有機ｅｌディスプレイパネル及びその製造方法 |
| FR2780969B1 (fr) * | 1998-07-10 | 2000-08-18 | Rhone Poulenc Nutrition Animal | Procede de separation de l'acide hydroxymethylthiobutyrique |
| JP4517474B2 (ja) * | 2000-07-25 | 2010-08-04 | 住友化学株式会社 | ２−ヒドロキシ−４−メチルチオブタン酸の製造方法 |
| JP4517486B2 (ja) * | 2000-09-25 | 2010-08-04 | 住友化学株式会社 | ２−ヒドロキシ−４−メチルチオブタンニトリルの製造方法 |
| JP4517491B2 (ja) * | 2000-10-11 | 2010-08-04 | 住友化学株式会社 | ２−ヒドロキシ−４−メチルチオブタン酸の製造方法 |
| JP4517520B2 (ja) * | 2001-02-27 | 2010-08-04 | 住友化学株式会社 | ２−ヒドロキシ−４−メチルチオブタン酸の製造方法 |
| DE102004041250A1 (de) * | 2004-08-26 | 2006-03-02 | Degussa Ag | Herstellung von 2-Hydroxy-4-Methylthiobuttersäure |
| JP2007238552A (ja) * | 2006-03-10 | 2007-09-20 | Sumitomo Chemical Co Ltd | ２−ヒドロキシ−４−メチルチオブタン酸の製造方法および製造装置 |
| KR101911563B1 (ko) | 2011-02-23 | 2018-10-24 | 에보니크 데구사 게엠베하 | 3-(메틸티오)프로판알 및 시안화수소로부터 2-히드록시-4-(메틸티오)부탄니트릴을 제조하는 방법 |
| DE102011081828A1 (de) | 2011-08-30 | 2013-02-28 | Evonik Degussa Gmbh | Verfahren zur Umsetzung von Methylmercaptopropionaldehyd aus Roh-Acrolein und Roh-Methylmercaptan |
| MY171361A (en) | 2011-08-30 | 2019-10-10 | Evonik Operations Gmbh | Method for producing a methionine salt |
| RU2571755C2 (ru) * | 2013-10-23 | 2015-12-20 | Андрей Вилорьевич Доронин | Способ сернокислотной переработки сырья |
| EP3388523A1 (en) | 2017-04-13 | 2018-10-17 | Evonik Degussa GmbH | Enzymatic method for producing 2-hydroxy-4-methylmercaptobutanoic acid (mha) |
| CN114349671B (zh) * | 2022-03-18 | 2022-05-27 | 蓝星安迪苏南京有限公司 | 化合物及蛋氨酸羟基衍生物的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1269995C (en) * | 1983-11-14 | 1990-06-05 | PREPARATION OF 2-HYDROXY-METHYLTHIOBUTYRIC ACID LIQUID | |
| US4524077A (en) * | 1983-11-14 | 1985-06-18 | Monsanto Company | Liquid 2-hydroxy-4-methylthiobutyric acid and process for the preparation thereof |
| ES2005784A6 (es) * | 1988-02-22 | 1989-03-16 | Desarrollo Tecnico Ind S A Soc | Un procedimiento para preparar soluciones acuosas de acido 2-hidroxi-4-metil-tiobutirico. |
| US5498790A (en) * | 1993-06-09 | 1996-03-12 | Novus International, Inc. | Regeneration of sulfuric acid from sulfate by-products of 2-hydroxy-4-(methylthio)butyric acid manufacture |
| DE4428608C1 (de) * | 1994-08-12 | 1996-02-29 | Degussa | Verfahren zur Gewinnung von 2-Hydroxy-4-methylthiobuttersäure (MHA) |
-
1995
- 1995-12-23 DE DE19548538A patent/DE19548538C2/de not_active Expired - Fee Related
-
1996
- 1996-12-05 CN CN96199293A patent/CN1067377C/zh not_active Expired - Lifetime
- 1996-12-05 TR TR1998/01190T patent/TR199801190T2/xx unknown
- 1996-12-05 BR BR9612235A patent/BR9612235A/pt not_active Application Discontinuation
- 1996-12-05 ES ES96943038T patent/ES2160264T3/es not_active Expired - Lifetime
- 1996-12-05 US US09/091,796 patent/US6140536A/en not_active Expired - Lifetime
- 1996-12-05 EP EP96943038A patent/EP0874811B1/de not_active Expired - Lifetime
- 1996-12-05 RU RU98114099/04A patent/RU2160730C2/ru active
- 1996-12-05 JP JP52325597A patent/JP3962089B2/ja not_active Expired - Lifetime
- 1996-12-05 DE DE59607103T patent/DE59607103D1/de not_active Expired - Lifetime
- 1996-12-05 KR KR10-1998-0704772A patent/KR100460364B1/ko not_active Expired - Fee Related
- 1996-12-05 WO PCT/EP1996/005437 patent/WO1997023452A1/de not_active Ceased
- 1996-12-05 AU AU11906/97A patent/AU717705B2/en not_active Ceased
- 1996-12-19 ID IDP963809A patent/ID16007A/id unknown
- 1996-12-19 MY MYPI96005345A patent/MY117493A/en unknown
- 1996-12-20 IN IN2209CA1996 patent/IN190919B/en unknown
- 1996-12-20 TW TW085115766A patent/TW371655B/zh active
-
1998
- 1998-06-17 MX MX9804881A patent/MX9804881A/es not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6814988B2 (en) | 1997-07-25 | 2004-11-09 | Novus International, Inc. | Process for optimizing milk production |
Also Published As
| Publication number | Publication date |
|---|---|
| IN190919B (ref) | 2003-08-30 |
| AU1190697A (en) | 1997-07-17 |
| DE19548538A1 (de) | 1997-06-26 |
| EP0874811A1 (de) | 1998-11-04 |
| WO1997023452A1 (de) | 1997-07-03 |
| DE59607103D1 (de) | 2001-07-19 |
| TW371655B (en) | 1999-10-11 |
| MX9804881A (es) | 1998-10-31 |
| MY117493A (en) | 2004-07-31 |
| ES2160264T3 (es) | 2001-11-01 |
| BR9612235A (pt) | 1999-07-13 |
| KR19990076661A (ko) | 1999-10-15 |
| JP3962089B2 (ja) | 2007-08-22 |
| KR100460364B1 (ko) | 2005-05-20 |
| RU2160730C2 (ru) | 2000-12-20 |
| JP2000502110A (ja) | 2000-02-22 |
| CN1067377C (zh) | 2001-06-20 |
| DE19548538C2 (de) | 1997-12-18 |
| TR199801190T2 (xx) | 1998-11-23 |
| US6140536A (en) | 2000-10-31 |
| CN1205688A (zh) | 1999-01-20 |
| ID16007A (id) | 1997-08-28 |
| EP0874811B1 (de) | 2001-06-13 |
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