GB596034A - Improvements relating to the production of unsaturated carboxylic acids - Google Patents
Improvements relating to the production of unsaturated carboxylic acidsInfo
- Publication number
- GB596034A GB596034A GB1812845A GB1812845A GB596034A GB 596034 A GB596034 A GB 596034A GB 1812845 A GB1812845 A GB 1812845A GB 1812845 A GB1812845 A GB 1812845A GB 596034 A GB596034 A GB 596034A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- lead
- oxygen
- carboxylic acids
- unsaturated carboxylic
- 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
- 150000001735 carboxylic acids Chemical class 0.000 title abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 3
- 239000011133 lead Substances 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 2
- 229910017052 cobalt Inorganic materials 0.000 abstract 2
- 239000010941 cobalt Substances 0.000 abstract 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 2
- 229910052748 manganese Inorganic materials 0.000 abstract 2
- 239000011572 manganese Substances 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 abstract 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000005642 Oleic acid Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229930016911 cinnamic acid Natural products 0.000 abstract 1
- 235000013985 cinnamic acid Nutrition 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract 1
- 150000004670 unsaturated fatty acids Chemical class 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
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
Abstract
Unsaturated carboxylic acids are produced by treating their corresponding aldehydes in the liquid phase with a gas containing oxygen in the presence of a catalyst consisting of the salts of unsaturated fatty acids containing more than ten carbon atoms, e.g. oleic acid, with a plurality of multivalent metals, e.g. lead, manganese and cobalt. In the preparation of unsaturated acids, such as acrylic acid, methacrylic acid and crotonic acid, which possess a strong tendency to undergo polymerization, it is advantageous to use oxygen or a current of air enriched by oxygen with a catalyst containing a lead salt, and not allowing the temperature to rise above 35 DEG C. When the aldehyde is a solid or a liquid of high viscosity, the oxidation may be carried out in an inert solvent, e.g. esters such as ethyl acetate. A catalyst consisting of a mixture of lead, manganese and cobalt oleates is used in examples in which cinnamic acid, oenanthylidene-oenanthic acid, crotonic acid, acrylic acid and a -ethyl hexenoic acid are obtained by the oxidation of their corresponding aldehydes. Specifications 550,134 and 560,166 are referred to.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB596034A true GB596034A (en) | 1947-12-24 |
Family
ID=1733670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1812845A Expired GB596034A (en) | 1945-07-16 | Improvements relating to the production of unsaturated carboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB596034A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1244768B (en) * | 1963-02-06 | 1967-07-20 | Hoechst Ag | Process for the production of sorbic acid or its alkali metal salts by the oxidation of sorbic aldehyde |
| DE1245363B (en) * | 1957-03-18 | 1967-07-27 | Standard Oil Co | Process for the production of acrylic acid or methacrylic acid by the oxidation of acrolein or methacrolein |
| DE1253703B (en) * | 1960-04-14 | 1967-11-09 | Distillers Co Yeast Ltd | Process for the production of acrylic or methacrylic acid from acrolein, methacrolein or propylene |
| DE1543046B1 (en) * | 1964-02-13 | 1971-02-11 | Ici Ltd | Process for the production of acrylic acid |
-
1945
- 1945-07-16 GB GB1812845A patent/GB596034A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1245363B (en) * | 1957-03-18 | 1967-07-27 | Standard Oil Co | Process for the production of acrylic acid or methacrylic acid by the oxidation of acrolein or methacrolein |
| DE1253703B (en) * | 1960-04-14 | 1967-11-09 | Distillers Co Yeast Ltd | Process for the production of acrylic or methacrylic acid from acrolein, methacrolein or propylene |
| DE1244768B (en) * | 1963-02-06 | 1967-07-20 | Hoechst Ag | Process for the production of sorbic acid or its alkali metal salts by the oxidation of sorbic aldehyde |
| DE1543046B1 (en) * | 1964-02-13 | 1971-02-11 | Ici Ltd | Process for the production of acrylic acid |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1042631A (en) | New fused polycyclic hydrocarbon derivatives and processes for the preparation thereof | |
| GB596034A (en) | Improvements relating to the production of unsaturated carboxylic acids | |
| Skellon et al. | Some new metallic compounds of unsaturated fatty acids: Their preparation and properties | |
| US2287537A (en) | Process for the production of betaalkoxycarboxylic acids | |
| US2820046A (en) | Oxidation of fatty acids | |
| ES396478A1 (en) | Gel-forming monoglycerides of cyclic carboxylic acids | |
| ES348640A1 (en) | Preparation of aromatic disubstituted carboxylic acids | |
| GB740005A (en) | Manufacture of acrylates | |
| GB716124A (en) | Improvements in or relating to the production of acetic acid and/or the secondary butyl ester thereof | |
| GB813842A (en) | Improvements in or relating to the production of aliphatic mono-and di-carboxylic acids | |
| US3013038A (en) | Conversion of acids to alcohols having one less carbon atom and esters thereof | |
| GB560166A (en) | Improvements in or relating to the oxidation of unsaturated aldehydes | |
| GB608539A (en) | A process for the oxidation of cyclic ethers | |
| US2288965A (en) | Pbocess fob the manufacture of | |
| JPS5227089A (en) | Catalyst for production of carboxylic acid ester | |
| GB461808A (en) | Improvements in the production of acetic anhydride | |
| GB550134A (en) | Improvements relating to the production of carboxylic acids | |
| GB809451A (en) | Oxidation of fatty acids | |
| GB567009A (en) | New quinoline derivatives | |
| GB530269A (en) | Improvements in or relating to the manufacture of the nitriles of organic carboxylicacids | |
| GB679662A (en) | Process of preparing aliphatic carboxylic acid anhydrides | |
| GB719574A (en) | Improvements in or relating to new fluorocarbon acyl sulphuric acids and methods of making the same | |
| GB830671A (en) | Process for oxidizing glutaraldehydes | |
| GB956180A (en) | Process for the production of higher carboxylic acid esters | |
| GR14319B (en) | METHOD FOR PREPARATION OF MONOESTERS OF TERREPHALIC ACID. |