DE2527120A1 - Verfahren zur herstellung von alpha-hydroxyisobutyramid aus acetoncyanhydrin - Google Patents
Verfahren zur herstellung von alpha-hydroxyisobutyramid aus acetoncyanhydrinInfo
- Publication number
- DE2527120A1 DE2527120A1 DE19752527120 DE2527120A DE2527120A1 DE 2527120 A1 DE2527120 A1 DE 2527120A1 DE 19752527120 DE19752527120 DE 19752527120 DE 2527120 A DE2527120 A DE 2527120A DE 2527120 A1 DE2527120 A1 DE 2527120A1
- Authority
- DE
- Germany
- Prior art keywords
- acetone
- catalyst
- hydration
- hydroxyisobutyramide
- cyanohydrin
- 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.)
- Withdrawn
Links
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical compound CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-N 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 50
- 239000003054 catalyst Substances 0.000 claims description 24
- 230000036571 hydration Effects 0.000 claims description 15
- 238000006703 hydration reaction Methods 0.000 claims description 15
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 8
- 230000004048 modification Effects 0.000 claims description 5
- 238000012986 modification Methods 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 238000002474 experimental method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007596 consolidation process Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- PVGRIQYJDHKRFC-UHFFFAOYSA-N copper;oxomolybdenum Chemical compound [Cu].[Mo]=O PVGRIQYJDHKRFC-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- ZADYMNAVLSWLEQ-UHFFFAOYSA-N magnesium;oxygen(2-);silicon(4+) Chemical compound [O-2].[O-2].[O-2].[Mg+2].[Si+4] ZADYMNAVLSWLEQ-UHFFFAOYSA-N 0.000 description 1
- 150000002697 manganese compounds Chemical class 0.000 description 1
- 229940099596 manganese sulfate Drugs 0.000 description 1
- 239000011702 manganese sulphate Substances 0.000 description 1
- 235000007079 manganese sulphate Nutrition 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
- C07C231/065—By hydration using metals or metallic ions as catalyst
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752527120 DE2527120A1 (de) | 1975-06-18 | 1975-06-18 | Verfahren zur herstellung von alpha-hydroxyisobutyramid aus acetoncyanhydrin |
| FR7613771A FR2314915A1 (fr) | 1975-06-18 | 1976-05-07 | Procede de preparation du 2-hydroxyisobutyramide a partir de l'acetone-cyanhydrine |
| US05/692,109 US4018829A (en) | 1975-06-18 | 1976-06-02 | Method for making α-hydroxy-isobutyramide from acetone cyanohydrin |
| GB23729/76A GB1490324A (en) | 1975-06-18 | 1976-06-08 | Preparing alpha-hydroxyisobutyramide |
| JP51067566A JPS52222A (en) | 1975-06-18 | 1976-06-09 | Method of manufacturing alpha hydroxyisobutylamide |
| NL7606579A NL7606579A (nl) | 1975-06-18 | 1976-06-17 | Werkwijze voor de bereiding van (alpha)-hydroxyisobu- tyramide uit acetoncyaanhydrien. |
| BE168076A BE843129A (fr) | 1975-06-18 | 1976-06-18 | Procede de preparation d'amide alpha-hydroxyisobutyrique a partir d'acetone-cyanhydrine et produit ainsi obtenu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752527120 DE2527120A1 (de) | 1975-06-18 | 1975-06-18 | Verfahren zur herstellung von alpha-hydroxyisobutyramid aus acetoncyanhydrin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2527120A1 true DE2527120A1 (de) | 1976-12-30 |
Family
ID=5949338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752527120 Withdrawn DE2527120A1 (de) | 1975-06-18 | 1975-06-18 | Verfahren zur herstellung von alpha-hydroxyisobutyramid aus acetoncyanhydrin |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4018829A (enExample) |
| JP (1) | JPS52222A (enExample) |
| BE (1) | BE843129A (enExample) |
| DE (1) | DE2527120A1 (enExample) |
| FR (1) | FR2314915A1 (enExample) |
| GB (1) | GB1490324A (enExample) |
| NL (1) | NL7606579A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006140A1 (de) * | 1978-06-08 | 1980-01-09 | Chemie Linz Aktiengesellschaft | Verfahren zur Herstellung von alpha-Hydroxycarbonsäureamiden |
| EP0597298A1 (en) * | 1992-11-09 | 1994-05-18 | Mitsubishi Gas Chemical Company, Inc. | Process for producing alpha-hydroxyisobutyramide |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4222960A (en) * | 1978-06-08 | 1980-09-16 | Chemie Linz Aktiengesellschaft | Process for the manufacture of α-hydroxycarboxylic acid amides |
| US4950801A (en) * | 1989-01-19 | 1990-08-21 | Mitsubishi Gas Chemical Company, Inc. | Process for producing alpha-hydroxycarboxylic acid amide |
| US5175366A (en) * | 1989-08-08 | 1992-12-29 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a denaturated manganese dioxide catalyst for the hydration reaction of cyanohydrins |
| JP2853190B2 (ja) * | 1989-08-08 | 1999-02-03 | 三菱瓦斯化学株式会社 | ニトリル水和触媒の製造方法 |
| JP2780373B2 (ja) * | 1989-09-07 | 1998-07-30 | 三菱瓦斯化学株式会社 | α―ヒドロキシカルボン酸アミドの製造法 |
| JP2827368B2 (ja) * | 1989-12-19 | 1998-11-25 | 三菱瓦斯化学株式会社 | α―ヒドロキシイソ酪酸アミドの製造法 |
| US5276185A (en) * | 1990-06-11 | 1994-01-04 | Mitsui Toatsu Chemicals, Inc. | Process for producing amide compounds |
| US5387715A (en) * | 1991-12-03 | 1995-02-07 | Mitsui Toatsu Chemicals, Inc. | Process for producing α-hydroxy-isobutyramide |
| KR960000850A (ko) | 1994-06-06 | 1996-01-25 | 사토 아키오 | 메타크릴산메틸의 연속제조방법 |
| US5756842A (en) * | 1995-11-07 | 1998-05-26 | Mitsubishi Gas Chemical Company, Inc. | Process for preparing lactamide |
| US7455827B2 (en) * | 2003-03-20 | 2008-11-25 | Council Of Scientific And Industrial Research | Process for preparing a catalyst for conversion of cyanopyridines to nicotinamides |
| DE102005047597A1 (de) * | 2005-10-05 | 2007-04-12 | Degussa Ag | Mangandioxid-Katalysator zur Hydrolyse von Carbonsäurenitrilen |
| DE102008001319A1 (de) | 2008-04-22 | 2009-10-29 | Evonik Röhm Gmbh | Katalysator zur Umsetzung von Carbonsäurenitrilen |
| DE102008044218A1 (de) | 2008-12-01 | 2010-06-02 | Evonik Röhm Gmbh | Verfahren zur Herstellung von einem Carbonsäureamid aus einer Carbonylverbindung und Blausäure |
| TW201102365A (en) * | 2009-07-03 | 2011-01-16 | China Petrochemical Dev Corp | Method for producing organic carboxylic acid amide |
| WO2011108717A1 (ja) | 2010-03-04 | 2011-09-09 | 三菱瓦斯化学株式会社 | アミド化合物製造用触媒およびアミド化合物の製造方法 |
| JP6274210B2 (ja) | 2013-07-16 | 2018-02-07 | 三菱瓦斯化学株式会社 | α−ヒドロキシイソ酪酸アミドの製造方法及び反応装置 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2229897A (en) * | 1940-03-02 | 1941-01-28 | American Cyanamid Co | Method of preparing alpha hydroxy carboxylic acids |
| US3166588A (en) * | 1961-04-14 | 1965-01-19 | Union Carbide Corp | Process for the production of alpha-hydroxy amides |
| CH479520A (de) * | 1964-07-09 | 1969-10-15 | Lonza Ag | Verfahren zur Herstellung von a-Oxycarbonsäuren |
| US3781351A (en) * | 1971-10-27 | 1973-12-25 | Union Oil Co | Preparation of alpha-hydroyamides |
-
1975
- 1975-06-18 DE DE19752527120 patent/DE2527120A1/de not_active Withdrawn
-
1976
- 1976-05-07 FR FR7613771A patent/FR2314915A1/fr active Granted
- 1976-06-02 US US05/692,109 patent/US4018829A/en not_active Expired - Lifetime
- 1976-06-08 GB GB23729/76A patent/GB1490324A/en not_active Expired
- 1976-06-09 JP JP51067566A patent/JPS52222A/ja active Pending
- 1976-06-17 NL NL7606579A patent/NL7606579A/xx not_active Application Discontinuation
- 1976-06-18 BE BE168076A patent/BE843129A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006140A1 (de) * | 1978-06-08 | 1980-01-09 | Chemie Linz Aktiengesellschaft | Verfahren zur Herstellung von alpha-Hydroxycarbonsäureamiden |
| EP0597298A1 (en) * | 1992-11-09 | 1994-05-18 | Mitsubishi Gas Chemical Company, Inc. | Process for producing alpha-hydroxyisobutyramide |
| US5463123A (en) * | 1992-11-09 | 1995-10-31 | Mitsubishi Gas Chemical Company, Inc. | Process for producing α-hydroxyisobutyramide |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52222A (en) | 1977-01-05 |
| NL7606579A (nl) | 1976-12-21 |
| FR2314915A1 (fr) | 1977-01-14 |
| US4018829A (en) | 1977-04-19 |
| BE843129A (fr) | 1976-10-18 |
| GB1490324A (en) | 1977-11-02 |
| FR2314915B1 (enExample) | 1979-07-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |