JP4949249B2 - ２−ヒドロキシ−４−メチルチオ酪酸の製造 - Google Patents
２−ヒドロキシ−４−メチルチオ酪酸の製造 Download PDFInfo
- Publication number
- JP4949249B2 JP4949249B2 JP2007528639A JP2007528639A JP4949249B2 JP 4949249 B2 JP4949249 B2 JP 4949249B2 JP 2007528639 A JP2007528639 A JP 2007528639A JP 2007528639 A JP2007528639 A JP 2007528639A JP 4949249 B2 JP4949249 B2 JP 4949249B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- less
- methylthiobutyramide
- acid
- carried out
- 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.)
- Expired - Fee Related
Links
- PICCHNWCTUUCAQ-UHFFFAOYSA-N 2-hydroxypentanethioic s-acid Chemical compound CCCC(O)C(O)=S PICCHNWCTUUCAQ-UHFFFAOYSA-N 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000000463 material Substances 0.000 claims description 39
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 17
- DOLNLDKZJKDWLS-UHFFFAOYSA-N 2-hydroxypentanethioamide Chemical compound CCCC(O)C(N)=S DOLNLDKZJKDWLS-UHFFFAOYSA-N 0.000 claims description 14
- 238000000227 grinding Methods 0.000 claims description 14
- 230000007797 corrosion Effects 0.000 claims description 13
- 238000005260 corrosion Methods 0.000 claims description 13
- VWWOJJANXYSACS-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanenitrile Chemical compound CSCCC(O)C#N VWWOJJANXYSACS-UHFFFAOYSA-N 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 8
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 claims description 4
- 229910000990 Ni alloy Inorganic materials 0.000 claims description 4
- 229910000851 Alloy steel Inorganic materials 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- ONFOSYPQQXJWGS-UHFFFAOYSA-N 2-hydroxy-4-(methylthio)butanoic acid Chemical compound CSCCC(O)C(O)=O ONFOSYPQQXJWGS-UHFFFAOYSA-N 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- 229930182817 methionine Natural products 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003674 animal food additive Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 229910000856 hastalloy Inorganic materials 0.000 description 3
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 244000144977 poultry Species 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 235000019728 animal nutrition Nutrition 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- -1 ester acids Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000005554 pickling Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- 229910000599 Cr alloy Inorganic materials 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000005275 alloying Methods 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000788 chromium alloy Substances 0.000 description 1
- OGSYQYXYGXIQFH-UHFFFAOYSA-N chromium molybdenum nickel Chemical compound [Cr].[Ni].[Mo] OGSYQYXYGXIQFH-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 150000002742 methionines Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000003754 zirconium Chemical class 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
- C07C319/14—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004041250.2 | 2004-08-26 | ||
| DE102004041250A DE102004041250A1 (de) | 2004-08-26 | 2004-08-26 | Herstellung von 2-Hydroxy-4-Methylthiobuttersäure |
| PCT/EP2005/007530 WO2006021268A1 (de) | 2004-08-26 | 2005-07-12 | Herstellung von 2-hydroxy-4-methylthiobuttersäure |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011225834A Division JP5340362B2 (ja) | 2004-08-26 | 2011-10-13 | ２−ヒドロキシ−４−メチルチオ酪酸の製造 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008510739A JP2008510739A (ja) | 2008-04-10 |
| JP2008510739A5 JP2008510739A5 (enExample) | 2011-06-02 |
| JP4949249B2 true JP4949249B2 (ja) | 2012-06-06 |
Family
ID=35169872
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007528639A Expired - Fee Related JP4949249B2 (ja) | 2004-08-26 | 2005-07-12 | ２−ヒドロキシ−４−メチルチオ酪酸の製造 |
| JP2011225834A Expired - Fee Related JP5340362B2 (ja) | 2004-08-26 | 2011-10-13 | ２−ヒドロキシ−４−メチルチオ酪酸の製造 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011225834A Expired - Fee Related JP5340362B2 (ja) | 2004-08-26 | 2011-10-13 | ２−ヒドロキシ−４−メチルチオ酪酸の製造 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7148379B2 (enExample) |
| EP (1) | EP1781603B1 (enExample) |
| JP (2) | JP4949249B2 (enExample) |
| CN (1) | CN1984884B (enExample) |
| BR (1) | BRPI0514673A (enExample) |
| DE (1) | DE102004041250A1 (enExample) |
| ES (1) | ES2388141T3 (enExample) |
| WO (1) | WO2006021268A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2919607B1 (fr) * | 2007-07-31 | 2012-10-12 | Adisseo Ireland Ltd | Procede pour la conversion catalytique de 2-hydroxy-4- methylthiobutanenitrile (hmtbn) en 2-hydroxy-4- methylthiobutanamide (hmtbm). |
| JP5463839B2 (ja) * | 2008-10-10 | 2014-04-09 | 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 |
| SG161158A1 (en) * | 2008-10-10 | 2010-05-27 | Sumitomo Chemical Co | Process for producing 2-hydroxy-4-methylthiobutanoic acid |
| JP2010111665A (ja) * | 2008-10-10 | 2010-05-20 | 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 |
| US9169203B2 (en) | 2012-01-06 | 2015-10-27 | Novus International, Inc. | Sulfoxide-based surfactants |
| EP3374428A4 (en) | 2015-11-12 | 2019-06-05 | Novus International Inc. | SULFUR COMPOUNDS AS SOLVENTS |
| FR3081721B1 (fr) * | 2018-06-01 | 2022-04-15 | Arkema France | Procede de preparation d'un sel de lithium de bis(fluorosulfonyl)imide |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4533414A (en) * | 1980-07-10 | 1985-08-06 | Cabot Corporation | Corrosion-resistance nickel alloy |
| 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. |
| DE4342188C2 (de) * | 1993-12-10 | 1998-06-04 | Bayer Ag | Austenitische Legierungen und deren Verwendung |
| US5856567A (en) * | 1995-06-07 | 1999-01-05 | Novus International, Inc. | Continuous hydrolysis process for preparing 2-hydroxy-4-methylthiobutanioc acid or salts thereof |
| 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 |
| DE19548538C2 (de) | 1995-12-23 | 1997-12-18 | Degussa | Verfahren zur Gewinnung von 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 |
| RU2213729C2 (ru) | 1999-02-03 | 2003-10-10 | Сумитомо Кемикал Компани, Лимитед | Способ получения 2-гидрокси-4-метилтиобутановой кислоты |
| JP2003104959A (ja) * | 2001-09-28 | 2003-04-09 | Nippon Soda Co Ltd | メチオニンの製造方法 |
-
2004
- 2004-08-26 DE DE102004041250A patent/DE102004041250A1/de not_active Withdrawn
-
2005
- 2005-07-12 BR BRPI0514673-9A patent/BRPI0514673A/pt not_active Application Discontinuation
- 2005-07-12 EP EP05758847A patent/EP1781603B1/de not_active Expired - Lifetime
- 2005-07-12 WO PCT/EP2005/007530 patent/WO2006021268A1/de not_active Ceased
- 2005-07-12 ES ES05758847T patent/ES2388141T3/es not_active Expired - Lifetime
- 2005-07-12 CN CN2005800239581A patent/CN1984884B/zh not_active Expired - Fee Related
- 2005-07-12 JP JP2007528639A patent/JP4949249B2/ja not_active Expired - Fee Related
- 2005-08-25 US US11/212,023 patent/US7148379B2/en not_active Expired - Lifetime
-
2011
- 2011-10-13 JP JP2011225834A patent/JP5340362B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE102004041250A1 (de) | 2006-03-02 |
| WO2006021268A1 (de) | 2006-03-02 |
| CN1984884B (zh) | 2011-01-19 |
| EP1781603A1 (de) | 2007-05-09 |
| EP1781603B1 (de) | 2012-06-06 |
| BRPI0514673A (pt) | 2008-06-17 |
| JP5340362B2 (ja) | 2013-11-13 |
| ES2388141T3 (es) | 2012-10-09 |
| CN1984884A (zh) | 2007-06-20 |
| US20060047169A1 (en) | 2006-03-02 |
| US7148379B2 (en) | 2006-12-12 |
| JP2012031193A (ja) | 2012-02-16 |
| JP2008510739A (ja) | 2008-04-10 |
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