KR850004108A - 액상 2-하이드록시-메틸티오부티르산의 제조방법 - Google Patents
액상 2-하이드록시-메틸티오부티르산의 제조방법 Download PDFInfo
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- KR850004108A KR850004108A KR1019840007114A KR840007114A KR850004108A KR 850004108 A KR850004108 A KR 850004108A KR 1019840007114 A KR1019840007114 A KR 1019840007114A KR 840007114 A KR840007114 A KR 840007114A KR 850004108 A KR850004108 A KR 850004108A
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- South Korea
- Prior art keywords
- hydroxy
- water
- hydrolyzate
- mentioned
- extraction
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- 239000007788 liquid Substances 0.000 title claims 2
- SOGMDUPYAJRSJA-UHFFFAOYSA-N 2-hydroxy-2-methylbutanethioic s-acid Chemical compound CCC(C)(O)C(S)=O SOGMDUPYAJRSJA-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 21
- 238000000605 extraction Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 12
- 239000002904 solvent Substances 0.000 claims 12
- PICCHNWCTUUCAQ-UHFFFAOYSA-N 2-hydroxypentanethioic s-acid Chemical compound CCCC(O)C(O)=S PICCHNWCTUUCAQ-UHFFFAOYSA-N 0.000 claims 9
- 238000006460 hydrolysis reaction Methods 0.000 claims 9
- 230000007062 hydrolysis Effects 0.000 claims 7
- DOLNLDKZJKDWLS-UHFFFAOYSA-N 2-hydroxypentanethioamide Chemical compound CCCC(O)C(N)=S DOLNLDKZJKDWLS-UHFFFAOYSA-N 0.000 claims 6
- VWWOJJANXYSACS-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanenitrile Chemical compound CSCCC(O)C#N VWWOJJANXYSACS-UHFFFAOYSA-N 0.000 claims 5
- 238000004821 distillation Methods 0.000 claims 5
- 239000000047 product Substances 0.000 claims 5
- 239000007787 solid Substances 0.000 claims 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- 238000009835 boiling Methods 0.000 claims 3
- 239000012071 phase Substances 0.000 claims 3
- 238000001256 steam distillation Methods 0.000 claims 3
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 claims 2
- 239000008346 aqueous phase Substances 0.000 claims 2
- 239000000539 dimer Substances 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 2
- 239000000178 monomer Substances 0.000 claims 2
- 238000005192 partition Methods 0.000 claims 2
- OTIJNTWWDCIUNM-UHFFFAOYSA-N pentanethioic s-acid Chemical compound CCCCC(S)=O OTIJNTWWDCIUNM-UHFFFAOYSA-N 0.000 claims 2
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 claims 1
- QJDRJTFSPVQEDV-UHFFFAOYSA-N 2-methylbutanethioic s-acid Chemical compound CCC(C)C(O)=S QJDRJTFSPVQEDV-UHFFFAOYSA-N 0.000 claims 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 235000019730 animal feed additive Nutrition 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000012263 liquid product Substances 0.000 claims 1
- 238000000622 liquid--liquid extraction Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 238000010586 diagram Methods 0.000 description 2
- 238000005259 measurement 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/105—Aliphatic or alicyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/142—Amino acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
- A23K50/75—Feeding-stuffs specially adapted for particular animals for birds for poultry
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Birds (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 본 발명의 공정을 도시한 개요도.
제2도는 제1도을 좀더 구체적으로 도시한 공정도.
제3도는 본 발명에 이용된 가로흐름추출공정(Crossfolw extraction system)을 도시한 것이며,
제4도는 분배계수측정에 사용된 추출공정을 도시한 것이다.
Claims (25)
- 2-하이드록시-4-메틸티오부티로니트릴을 유기성분이 없는 상태로 초기농도가 약 50wt% 내지 약 70wt 사이인 황산으로 가수분해하여 2-하이드록시-4-메틸티오부티르아미드가 포함된 중간체인 수용성 가수분해 생성물용액을 제조항, 2-하이드록시-4-메틸티오부티르아미드를 유기성분이 없는 상태로 농도가 약 30wt% 내지 약 50wt% 사이인 황산으로 가수분해하여 2-하이드록시-4-메틸티오부티르산을 포함하는 수용성 가수분해물 용액을 제조한 다음, 가수분해물용액을 액-액추출공정에서 실제적으로 수불용성인 유기용매와 접속시켜 언급한 용매와 가스분해물로부터 전이된 2-하이드록시-4-메틸티오부티르산을 포함하는 추출물을 얻고, 여기에서 2-하이드록시-4-메틸티오부티르산을 회수하는 것을 특징으로 하는 색도와 냄새가 개선되고 저점도을 가지는 2-하이드록시-4-메틸티오부티르산의 제조방법.
- 제1항에 있어서, 가수분해 반응들을 가수분해물내에 2-하이드록시-4-메틸티오부티로니트릴과 2-하이드록시-4-메틸티오부티르아미드의 여분이 실질적으로 존재하지 않는 완전히 전환된 조건하에서 행하여진다는 것.
- 제1항에 있어서, 가수분해 반응들은 2-하이드록시-4-메틸티오부티로니트릴을 황산이 들어있는 용기에서 교반하면서 첨가하는 배치식으로 행한다는 것.
- 제3항에 있어서, 2-하이드록시-4-메틸티오부티로니트릴을 황산에 가하여 약 25℃ 내지 약 65℃ 사이의 온도에서서 가수분해함으로써 2-하이드록시-4-메틸티오부티르아미드를 함유하는 언급된 중간체 수용성가수분해 생성물 용액을 얻고, 언급된 2-하이드록시-4-메틸티오부티르아미드를 약 70℃ 내지 약 120℃사이의 온도에서 가수분해시켜 언급된 가수분해물 수용액을 얻는다는 것.
- 제4항에 있어서, 언급된 2-하이드록시-4-메틸티오부티로니트릴을 초기농도가 약 55wt% 내지 약 65wt% 사이인 황산에 가하여 약 40℃ 내지 약 60℃ 사이의 온도에서 2-하이드록시-4-메틸티오부티르산을 2-하이드록시-4-메틸티오부티르아미드로 가수분해한 후, 언급된 2-하이드록시-4-메틸티오부티르아미드를 유기성분이 없는 상태에서 농도가 약 30wt% 내지 약 40wt%사이인 황산과 약 85℃ 내지 약 95℃의 온도 사이에서 반응시켜 가수분해한다는 것.
- 제1항에 있어서, 언급된 2-하이드록시-4-메틸티오부티르산을 언급된 용매를 사용하여 연속적으로 향류추출을 행함으로써 수용성 가수분해물로부터 전이된 것이라는 것.
- 제6항에 있어서, 추출을 향류추출공정으로 행하고 여기에서 추출물은 가수분해물이 추출계내로 도입되는 위치보다 위에 위치한 지점에서 물과 혼합시켜 세척한다는 것.
- 제6항에 있어서, 추출은 용매상과 수용성상 사이의 물질전달을 증진시키기 위한 수단을 포함하는 추출지역을 가지는 연속식 향류추출시스템에서 행하며, 추출조작은 추출지역내에서 용매상이 연속상이 되도록 유지하면서 행한다는 것.
- 제1항에 있어서, 언급딘 용매의 비등점은 약 60℃ 내지 약 200℃ 사이이며, 2-하이드록시-4-메틸티오부티르산을 포함하는 언급된 용매와, 가수분해물과 언급된 용매가 서로 접촉한 후 남아있는 수용성 라피네이트 사이의 평형상태에서의 2-하이드록시-4-메틸티오부티르산에 대한 분배계수는 적어도 약 2이며, 2-하이드록시-4-메틸티오부티르산을 포함하는 추출시험편과, 언급된 추출시험편과 세척수가 서로 접촉한 후의 수용성상 사이의 평형상태에서의 분배계수는 적어도 약 1.0이며, 언급된 용매내에서 물의 용해도는 실온에서 약 12wt%를 초과하지 않는다는 것.
- 제9항에 있어서, 언급된 비등점은 약 70 내지 약 170℃ 사이이고, 용해도는 약 8wt%를 초과하지 않는다는 것.
- 제9항에 있어서, 용매는 케톤, 알데히드, 카르복실산의 알킬에스테르로 구성된 군으로부터 선택된 것이라는 것.
- 제1항에 있어서, 용매는 메틸푸로필케톤, 메틸에틸케톤, 메틸이소부틸케톤, 메틸아밀케톤, 에틸부틸케톤, 이이소부틸케톤, 메틸이소아밀케톤으로 구성된 군으로부터 선택된 것이라는 것.
- 제1항에 있어서, 가수분해물은 가수분해물내에 존재하는 고체를 사전에 분리함이 없는 추출함으로써, 라피네이트의 물함량은 추출시스템내에 고체들이 축적될 수 없는 충분한 량을 포함한다는 것.
- 제13항에 있어서, 추출시스템내로 충분한 물의 양이 도입되기 때문에 추출시스템내에 고체가 실질적인 양으로 도입되지 않는다는 것.
- 제14항에 있어서, 추출시스템내로 충분한 물의 양이 도입되기 때문에 추출시스템내에 실질적으로 고체가 형성되지 않는다는 것.
- 제14항에 있어서, 혼합물의 물의 함량은 가수분해결과에 따른 고체의 형성을 방지한다는 것.
- 제1항에 있어서, 추출하기전에 가수분해물은 감소된 압력하에서 부분적으로 증류한다는 것.
- 제17항에 있어서, 증류는 가수분해물로부터 유기액체상을 분리시키기전에 종결시킨다는 것.
- 제17항에 있어서, 가수분해물은 증류시킨 후에 가수분해물로부터 분리된 유기상물질을 재흡수하기 위해 물로 희석시킨다는 것.
- 제1항에 있어서, 추출물을 증기증류하여 용매를 제거시키고, 2-하이드록시-4-메틸티오부티르산과 물을 함유한 액체생성물인 하부생성물을 얻는다는 것.
- 제20항에 있어서, 증기증류는 하부생성물의 물의 양이 적어도 약 5wt%가 되도록 행한다는 것.
- 제21항에 있어서, 증류는 다수의 평형단(equilibrium stage)으로 구성된 컬럼에서 행하며 평형단의 하단은 온도가 약 120℃를 초과하지 않고, 압력은 약 1기압을 초과하지 않도록 유지시킨다는 것.
- 제20항에 있어서, 증류컬럼내에서 2-하이드록시-4-메틸티오부티르산의 체류시간은 약 1시간 30분을 넘지 않는다는 것.
- 제22항에 있어서, 증기증류는 증류컬럼내에서 액체상중 물이 적어도 약 4wt%를 유지하도록 조작하여야 한다는 것.
- 가드너 스케일로 측정한 색도가 약 10이하, 이량체와 기타 소중합체 합에 대한 단량체의 무게비가 적어도 2.8이고 케논-펜스키점도계로 측정한 25℃의 동점도가 90센티스토크 이하이며, 가속비 열계량법으로 측정한 결과 약 150℃ 이하의 어떠한 온도에서도 열화학적 흡열이나 발열을 나타내지 않는 2-하이드록시-4-메틸티오부티르산 단량체, 이량체 및 소주합체를 약 80 내지 95wt%, 물을 약 5 내지 20wt% 함유시킴으로써 구성된 액체상의 가축사료 첨가물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/550,857 US4524077A (en) | 1983-11-14 | 1983-11-14 | Liquid 2-hydroxy-4-methylthiobutyric acid and process for the preparation thereof |
| US550857 | 1983-11-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850004108A true KR850004108A (ko) | 1985-07-01 |
| KR870000657B1 KR870000657B1 (ko) | 1987-04-04 |
Family
ID=24198852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840007114A KR870000657B1 (ko) | 1983-11-14 | 1984-11-13 | 액상 2-하이드록시-메틸티오부티르산의 제조방법 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4524077A (ko) |
| EP (1) | EP0142488B1 (ko) |
| JP (2) | JPS60156396A (ko) |
| KR (1) | KR870000657B1 (ko) |
| AT (1) | ATE29131T1 (ko) |
| AU (1) | AU562078B2 (ko) |
| CA (1) | CA1263668C (ko) |
| DE (1) | DE3465592D1 (ko) |
| GB (1) | GB2149791B (ko) |
| GE (1) | GEP19960463B (ko) |
| MX (1) | MX163989B (ko) |
| SU (1) | SU1428193A3 (ko) |
| ZA (1) | ZA848847B (ko) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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. |
| MY109603A (en) * | 1992-05-21 | 1997-03-31 | Daicel Chem | Process for producing 2-hydroxy-4-methylthiobutanoic acid |
| 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 |
| EP0770061B1 (de) * | 1994-07-11 | 1999-04-07 | Degussa Aktiengesellschaft | Verfahren zur gewinnung von 2-hydroxy-4-methylthiobuttersäure (mha), mha und dessen verwendung |
| DE4428608C1 (de) * | 1994-08-12 | 1996-02-29 | Degussa | Verfahren zur Gewinnung von 2-Hydroxy-4-methylthiobuttersäure (MHA) |
| CN1094925C (zh) * | 1995-06-07 | 2002-11-27 | 诺沃斯国际公司 | 制备2－羟基－4－甲基硫代丁酸或其盐的连续水解法 |
| US5856567A (en) * | 1995-06-07 | 1999-01-05 | Novus International, Inc. | Continuous hydrolysis process for preparing 2-hydroxy-4-methylthiobutanioc acid or salts thereof |
| DE19548538C2 (de) * | 1995-12-23 | 1997-12-18 | Degussa | Verfahren zur Gewinnung von 2-Hydroxy-4-methylthiobuttersäure (MHA) |
| DE19654485A1 (de) * | 1996-12-27 | 1998-07-02 | Degussa | Verfahren zur Gewinnung von lagerstabiler 2-Hydroxy-4-methylthiobuttersäure (MHA) |
| JP3804210B2 (ja) * | 1997-03-04 | 2006-08-02 | 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 |
| US6017563A (en) | 1997-07-25 | 2000-01-25 | Novus International, Inc. | Process for optimizing milk production |
| FR2780968B1 (fr) * | 1998-07-10 | 2000-08-18 | Rhone Poulenc Nutrition Animal | Procede de preparation de l'acide hydroxymethylthiobutyrique |
| FR2780969B1 (fr) * | 1998-07-10 | 2000-08-18 | Rhone Poulenc Nutrition Animal | Procede de separation de l'acide hydroxymethylthiobutyrique |
| FR2791673B1 (fr) * | 1999-04-02 | 2001-06-08 | Rhone Poulenc Animal Nutrition | Procede de preparation des esters de l'acide hydroxymethylthiobutyrique |
| US6342651B1 (en) | 1999-08-05 | 2002-01-29 | Novus International, Inc. | Reductive combustion of ammonium salts of sulfuric acid |
| US6649794B2 (en) | 2000-02-18 | 2003-11-18 | Sumitomo Chemical Company, Limited | Method for producing 2-Hydroxy-4-Methylthiobutanoic Acid |
| TWI296652B (en) * | 2000-03-29 | 2008-05-11 | Mitsui Chemicals Inc | Production process of amide compound |
| 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 |
| 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 |
| DE10316110A1 (de) * | 2003-04-09 | 2004-10-28 | Degussa Ag | Verfahren zur Herstellung von 2-Hydroxy-4-methylthio-buttersäure Ammoniumsalz |
| FR2871028B1 (fr) * | 2004-06-08 | 2006-12-29 | Adisseo Ireland Ltd | Complement alimentaire pour animaux, comprenant un additif olfactif |
| JP4696496B2 (ja) | 2004-08-18 | 2011-06-08 | 住友化学株式会社 | ２−ヒドロキシ−４−メチルチオ酪酸の製造方法 |
| WO2006041209A1 (ja) * | 2004-10-14 | 2006-04-20 | Sumitomo Chemical Company, Limited | ２－ヒドロキシ－４－（メチルチオ）酪酸の製造方法 |
| DE102005050106B4 (de) * | 2005-10-18 | 2008-04-30 | Josef Meissner Gmbh & Co. Kg | Rückgewinnung von Nitriersäuregemischen aus Nitrienprozessen |
| ES2279719B1 (es) * | 2006-01-26 | 2008-07-16 | Timac Agro España, S.A. | Nuevo activador metabolico y nutricional para las plantas. |
| ES2411712T3 (es) | 2006-07-21 | 2013-07-08 | Sumitomo Chemical Company, Limited | Proceso para producir compuestos de 2-hidroxi-4-(metiltio)butirato y sus intermedios |
| DE102007062199A1 (de) * | 2007-12-21 | 2009-06-25 | Evonik Degussa Gmbh | 2-Methylthioethyl-substituierte Heterocyclen als Futtermitteladditive |
| JP2009161499A (ja) * | 2008-01-10 | 2009-07-23 | Sumitomo Chemical Co Ltd | ２−ヒドロキシ−４−メチルチオブタンアミドの製造方法 |
| FR2938535B1 (fr) | 2008-11-20 | 2012-08-17 | Arkema France | Procede de fabrication de methylmercaptopropionaldehyde et de methionine a partir de matieres renouvelables |
| FR2939791B1 (fr) * | 2008-12-16 | 2011-01-14 | Adisseo France Sas | Procede de preparation d'acroleine a partir de glycerol ou de glycerine brute |
| CN103429748B (zh) | 2010-12-30 | 2016-01-06 | 代谢探索者公司 | 甲硫氨酸羟基类似物(mha)的发酵产生 |
| RS57845B1 (sr) | 2012-02-09 | 2018-12-31 | Novus Int Inc | Ciklični dimeri koji sadrže heteroatom |
| KR101419118B1 (ko) * | 2012-07-11 | 2014-07-11 | 김건희 | 사료용 향료 조성물 |
| ES2703051T3 (es) | 2012-07-12 | 2019-03-06 | Novus Int Inc | Composiciones de matriz y de capa para la protección de agentes bioactivos |
| MX2016010596A (es) * | 2014-02-20 | 2016-11-15 | Smidth As F L | Sedimentador de columna para la separacion de fases liquido/liquido de alto redimiento en procesos hidromelurciales y metodos de los mismos. |
| CN104860855B (zh) * | 2014-12-08 | 2017-06-16 | 宁夏紫光天化蛋氨酸有限责任公司 | 一种高纯度的d,l‑2‑羟基‑4‑甲硫基丁酸酯的制备方法 |
| US10106496B2 (en) | 2016-06-24 | 2018-10-23 | Novus International, Inc. | Hydroxy methionine analog formulations suitable for specialty chemical applications |
| FR3064006B1 (fr) | 2017-03-16 | 2019-03-29 | Adisseo France S.A.S. | Procede de fabrication de l'acide-2-hydroxy-4-methylthio-butyrique |
| US10584306B2 (en) | 2017-08-11 | 2020-03-10 | Board Of Regents Of The University Of Oklahoma | Surfactant microemulsions |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB722024A (en) * | 1950-10-31 | 1955-01-19 | Monsanto Chemicals | Production of alpha-hydroxy-gamma-mercapto-carboxylic acids and salts thereof and compositions containing the same |
| US2745745A (en) * | 1952-10-30 | 1956-05-15 | Monsanto Chemicals | Poultry feed |
| US2938053A (en) * | 1955-12-29 | 1960-05-24 | Monsanto Chemicals | Amino acid analogues |
| CH385823A (de) * | 1959-09-01 | 1964-12-31 | Inventa Ag | Verfahren zur Herstellung des Calciumsalzes der a-Oxy-y-methylthio-buttersäure |
| BE611435A (fr) * | 1960-12-14 | 1962-06-12 | Stamicarbon | Procédé de préparation de sels métalliques d'acide alpha-hydroxy- gamma -méthylmercaptobutyrique |
| US3773927A (en) * | 1971-12-20 | 1973-11-20 | Du Pont | Preparation of an aqueous slurry of ammonium chloride and methylmercapto-hydroxybutyric acid |
| US4310690A (en) * | 1980-10-08 | 1982-01-12 | E. I. Du Pont De Nemours And Company | Preparation of the calcium salt of α-hydroxy-gamma-methylmercaptobutyric acid |
-
1983
- 1983-11-14 US US06/550,857 patent/US4524077A/en not_active Expired - Lifetime
-
1984
- 1984-11-13 SU SU843812267A patent/SU1428193A3/ru active
- 1984-11-13 KR KR1019840007114A patent/KR870000657B1/ko not_active IP Right Cessation
- 1984-11-13 GB GB08428657A patent/GB2149791B/en not_active Expired
- 1984-11-13 JP JP59239325A patent/JPS60156396A/ja active Granted
- 1984-11-13 CA CA467699A patent/CA1263668C/en not_active Expired
- 1984-11-13 ZA ZA848847A patent/ZA848847B/xx unknown
- 1984-11-13 AU AU35359/84A patent/AU562078B2/en not_active Expired
- 1984-11-13 EP EP84870150A patent/EP0142488B1/en not_active Expired
- 1984-11-13 MX MX7002A patent/MX163989B/es unknown
- 1984-11-13 DE DE8484870150T patent/DE3465592D1/de not_active Expired
- 1984-11-13 AT AT84870150T patent/ATE29131T1/de not_active IP Right Cessation
-
1992
- 1992-07-27 JP JP4199865A patent/JPH0797970B2/ja not_active Expired - Lifetime
- 1992-12-25 GE GEAP1992440A patent/GEP19960463B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05211846A (ja) | 1993-08-24 |
| ZA848847B (en) | 1985-09-25 |
| EP0142488A3 (en) | 1985-06-26 |
| US4524077A (en) | 1985-06-18 |
| GEP19960463B (en) | 1996-07-15 |
| SU1428193A3 (ru) | 1988-09-30 |
| KR870000657B1 (ko) | 1987-04-04 |
| CA1263668A (en) | 1989-12-05 |
| GB2149791B (en) | 1988-04-20 |
| ATE29131T1 (de) | 1987-09-15 |
| GB2149791A (en) | 1985-06-19 |
| CA1263668C (en) | 1989-12-05 |
| JPS60156396A (ja) | 1985-08-16 |
| AU3535984A (en) | 1985-05-23 |
| JPH051787B2 (ko) | 1993-01-11 |
| EP0142488A2 (en) | 1985-05-22 |
| MX163989B (es) | 1992-07-07 |
| GB8428657D0 (en) | 1984-12-19 |
| EP0142488B1 (en) | 1987-08-26 |
| DE3465592D1 (en) | 1987-10-01 |
| JPH0797970B2 (ja) | 1995-10-25 |
| AU562078B2 (en) | 1987-05-28 |
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