GB1014153A - A process for the preparation of alpha,beta-unsaturated carboxylic acids - Google Patents
A process for the preparation of alpha,beta-unsaturated carboxylic acidsInfo
- Publication number
- GB1014153A GB1014153A GB3489162A GB3489162A GB1014153A GB 1014153 A GB1014153 A GB 1014153A GB 3489162 A GB3489162 A GB 3489162A GB 3489162 A GB3489162 A GB 3489162A GB 1014153 A GB1014153 A GB 1014153A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- butan
- carboxylic acid
- acetoxy
- catalyst
- 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
Links
- 238000000034 method Methods 0.000 title abstract 2
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 title abstract 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 9
- 229910052799 carbon Inorganic materials 0.000 abstract 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 4
- 150000001721 carbon Chemical group 0.000 abstract 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 150000002576 ketones Chemical class 0.000 abstract 4
- YUXLUIFZKUCMQL-UHFFFAOYSA-N (2-methyl-3-oxobutyl) acetate Chemical compound CC(=O)C(C)COC(C)=O YUXLUIFZKUCMQL-UHFFFAOYSA-N 0.000 abstract 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 abstract 2
- 229910001882 dioxygen Inorganic materials 0.000 abstract 2
- 125000001033 ether group Chemical group 0.000 abstract 2
- 229940071125 manganese acetate Drugs 0.000 abstract 2
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- NWCYECXHIYEBJE-UHFFFAOYSA-N 3-oxobutyl acetate Chemical compound CC(=O)CCOC(C)=O NWCYECXHIYEBJE-UHFFFAOYSA-N 0.000 abstract 1
- XVYLGLMTEZPIQC-UHFFFAOYSA-N 4-(dimethylamino)-3-methylpentan-2-one Chemical compound CN(C)C(C)C(C)C(C)=O XVYLGLMTEZPIQC-UHFFFAOYSA-N 0.000 abstract 1
- QFHUGPZHHLXOBK-UHFFFAOYSA-N 4-methoxy-3-methylbutan-2-one Chemical compound COCC(C)C(C)=O QFHUGPZHHLXOBK-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 239000011572 manganese Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229940032007 methylethyl ketone Drugs 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL269224 | 1961-09-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1014153A true GB1014153A (en) | 1965-12-22 |
Family
ID=19753279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3489162A Expired GB1014153A (en) | 1961-09-14 | 1962-09-12 | A process for the preparation of alpha,beta-unsaturated carboxylic acids |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1290137B (enrdf_load_stackoverflow) |
| GB (1) | GB1014153A (enrdf_load_stackoverflow) |
| NL (1) | NL269224A (enrdf_load_stackoverflow) |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1069614B (de) * | 1959-11-26 | Knapsack-Griesheim Aktiengesellschaft, Knapsack bei Köln | Verfahren zur Herstellung von aliphatischen a,/i-ungesättigten Carbonsäuren und bzw. oder ihren Derivaten | |
| DE597973C (de) * | 1933-01-20 | 1934-06-02 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von Saeuren aus Ketonen |
| DE657377C (de) * | 1933-08-03 | 1938-03-11 | Ici Ltd | Verfahren zum Herstellen von Estern oder Nitrilen von ungesaettigten aliphatischen ª‡-ª‰-Monocarbonsaeuren |
| DE670782C (de) * | 1935-10-29 | 1939-01-27 | Wacker Chemie Gmbh | Verfahren zur Herstellung von Acrylsaeure |
| DE698970C (de) * | 1939-03-02 | 1940-11-20 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von Carbonsaeuren durch katalytische Oxydation von Ketonen |
| US2379625A (en) * | 1940-08-16 | 1945-07-03 | Du Pont | Manufacture of methacrylic acid |
| DE724722C (de) * | 1940-11-29 | 1942-09-07 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von Carbonsaeuren |
| DE868297C (de) * | 1944-12-08 | 1953-02-23 | Distillers Co Yeast Ltd | Verfahren und Vorrichtung zur kontinuierlichen katalytischen Oxydation von Aldehyden und Ketonen |
| GB585527A (en) * | 1945-02-26 | 1947-02-10 | Distillers Co Yeast Ltd | Improvements in or relating to the oxidation of mesityl oxide |
| GB647094A (en) * | 1948-03-31 | 1950-12-06 | Amber Pharmaceuticals Ltd | Improvements in and relating to the manufacture of isovaleric acid |
| DE932368C (de) * | 1949-02-19 | 1955-08-29 | British Petroleum Co | Verfahren zur Herstellung von Carbonsaeuren |
| DE871147C (de) * | 1949-03-25 | 1953-03-19 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von ª‡-Neopentylacrylsaeure |
| US2744929A (en) * | 1952-09-26 | 1956-05-08 | Shell Dev | Production of unsaturated carboxylic acids |
| DE1062696B (de) * | 1952-11-06 | 1959-08-06 | Minnesota Mining & Mfg | Verfahren zur Herstellung von Acrylsaeure oder ihren Alkylestern aus Milchsaeure oder Milchsaeurealkylestern |
| BE528694A (enrdf_load_stackoverflow) * | 1953-05-08 | |||
| DE1018410B (de) * | 1954-01-14 | 1957-10-31 | Rhone Poulenc Sa | Verfahren zur Herstellung von Essigsaeure, Ameisensaeure und Formaldehyd durch katalytische Oxydation von Aceton |
| US2847464A (en) * | 1955-12-29 | 1958-08-12 | Escambia Chem Corp | Preparation of lactic acid |
| US2811545A (en) * | 1956-07-23 | 1957-10-29 | Escambia Chem Corp | Production of alpha-hydroxy isobutyric and methacrylic acids and their esters |
| US2811546A (en) * | 1956-09-11 | 1957-10-29 | Escambia Chem Corp | Production of alpha-hydroxy isobutyric and methacrylic acids and their esters |
| US2993373A (en) * | 1956-09-18 | 1961-07-25 | Kritz Jack | Ultrasonic flowmeters and transducers therefor |
| US2847465A (en) * | 1957-01-15 | 1958-08-12 | Escambia Chem Corp | Production of alpha hydroxyisobutyric acid |
| DE1174177B (de) * | 1957-03-01 | 1964-07-16 | Xaver Fendth & Co Maschinen Un | Kraftfahrzeug-Triebwerk, vorzugsweise fuer landwirtschaftliche Zugfahrzeuge |
| US2858330A (en) * | 1957-04-29 | 1958-10-28 | Shell Dev | Preparation of acrylate esters |
| US2971981A (en) * | 1957-05-10 | 1961-02-14 | Robert S Aries | Preparation of alpha-hydroxyisobutyric acid |
| US2945058A (en) * | 1957-09-11 | 1960-07-12 | Eastman Kodak Co | Manufacture of crotonic acid |
| DE1118193B (de) * | 1957-09-17 | 1961-11-30 | Knapsack Ag | Verfahren zur Herstellung von Methacrylsaeureestern durch katalytische Wasserabspaltung aus ª‡-Oxyisobuttersaeureestern |
| FR1210246A (fr) * | 1957-09-17 | 1960-03-07 | Knapsack Ag | Procédé de déshydratation des alpha-hydroxy-isobutyrates |
| FR1215702A (fr) * | 1957-10-29 | 1960-04-20 | Escambia Chem Corp | Perfectionnements à la production de l'acide méthacrylique et de ses esters |
| BE577067A (enrdf_load_stackoverflow) * | 1958-03-25 | |||
| BE579270A (enrdf_load_stackoverflow) * | 1958-06-03 | |||
| DE1124482B (de) * | 1958-06-25 | 1962-03-01 | Wacker Chemie Gmbh | Verfahren zur Herstellung von Acrylsaeure- und ª‡-Alkylacrylsaeureestern durch Alkoholabspaltung aus ª‰-Alkoxymonocarbonsaeureestern |
| FR1247411A (fr) * | 1958-12-24 | 1960-12-02 | Du Pont | Oxydation en phase vapeur des composés non saturés, notamment des alcènes-1 en acides acrylique et alcacrylique |
-
0
- NL NL269224D patent/NL269224A/xx unknown
-
1962
- 1962-09-12 GB GB3489162A patent/GB1014153A/en not_active Expired
- 1962-09-12 DE DE1962S0081433 patent/DE1290137B/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1290137B (de) | 1969-03-06 |
| NL269224A (enrdf_load_stackoverflow) |
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