GB560166A - Improvements in or relating to the oxidation of unsaturated aldehydes - Google Patents
Improvements in or relating to the oxidation of unsaturated aldehydesInfo
- Publication number
- GB560166A GB560166A GB1443340A GB1443340A GB560166A GB 560166 A GB560166 A GB 560166A GB 1443340 A GB1443340 A GB 1443340A GB 1443340 A GB1443340 A GB 1443340A GB 560166 A GB560166 A GB 560166A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxidation
- acrylic acid
- alcohol
- recovery
- compounds
- 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
- 230000003647 oxidation Effects 0.000 title abstract 4
- 238000007254 oxidation reaction Methods 0.000 title abstract 4
- 150000001299 aldehydes Chemical class 0.000 title 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- 238000011084 recovery Methods 0.000 abstract 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052770 Uranium Inorganic materials 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229910052804 chromium Inorganic materials 0.000 abstract 1
- 239000011651 chromium Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910001882 dioxygen Inorganic materials 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 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
- 238000000034 method Methods 0.000 abstract 1
- 229910052750 molybdenum Inorganic materials 0.000 abstract 1
- 239000011733 molybdenum Substances 0.000 abstract 1
- 229910052762 osmium Inorganic materials 0.000 abstract 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- -1 peroxide compounds Chemical class 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000004291 sulphur dioxide Substances 0.000 abstract 1
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052721 tungsten Inorganic materials 0.000 abstract 1
- 239000010937 tungsten Substances 0.000 abstract 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052720 vanadium Inorganic materials 0.000 abstract 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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
- 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
Acrylic acid is made by oxidizing acrolein with molecular oxygen in the presence of an acidic compound of vanadium at a temperature not above 45 DEG C. and, if desired, in the presence of a water-miscible solvent such as acetic acid, acrylic acid, or acetone. The recovery of the product from the reaction mixture may be effected without polymerization by adding a substance which will decompose the peroxide compounds present such as sulphur dioxide. The oxidation may be effected under conditions which prevent saponification during the process and recovery stages in which case acrylic anhydride is obtained. The acrylic acid in the reaction product may be esterified with acetylene or an alcohol, or an alcohol may be added initially so that esterification occurs during the oxidation. Examples are given. The Provisional Specification includes the oxidation of alpha substituted acrolein such as methylacrolein and chloracrolein, and mentions other catalysts including compounds, preferably acidic compounds, of chromium, tungsten, molybdenum, osmium and uranium and polyacids of such metals such as phosphotungstic and phosphomolybdic acids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1443340A GB560166A (en) | 1940-09-21 | 1940-09-21 | Improvements in or relating to the oxidation of unsaturated aldehydes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1443340A GB560166A (en) | 1940-09-21 | 1940-09-21 | Improvements in or relating to the oxidation of unsaturated aldehydes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB560166A true GB560166A (en) | 1944-03-23 |
Family
ID=10041121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1443340A Expired GB560166A (en) | 1940-09-21 | 1940-09-21 | Improvements in or relating to the oxidation of unsaturated aldehydes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB560166A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744928A (en) * | 1952-11-28 | 1956-05-08 | Shell Dev | Oxidation of unsaturated aldehydes to acids |
| US2744929A (en) * | 1952-09-26 | 1956-05-08 | Shell Dev | Production of unsaturated carboxylic acids |
| US2881212A (en) * | 1957-03-18 | 1959-04-07 | Standard Oil Co | Process and catalyst for the production of unsaturated carboxylic acids |
| US3021366A (en) * | 1958-10-10 | 1962-02-13 | Standard Oil Co | Process for the conversion of unsaturated aldehydes to the corresponding unsaturated acids |
-
1940
- 1940-09-21 GB GB1443340A patent/GB560166A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744929A (en) * | 1952-09-26 | 1956-05-08 | Shell Dev | Production of unsaturated carboxylic acids |
| US2744928A (en) * | 1952-11-28 | 1956-05-08 | Shell Dev | Oxidation of unsaturated aldehydes to acids |
| US2881212A (en) * | 1957-03-18 | 1959-04-07 | Standard Oil Co | Process and catalyst for the production of unsaturated carboxylic acids |
| US3021366A (en) * | 1958-10-10 | 1962-02-13 | Standard Oil Co | Process for the conversion of unsaturated aldehydes to the corresponding unsaturated acids |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1234641A (en) | ||
| US2292950A (en) | Catalytic oxidation | |
| GB560166A (en) | Improvements in or relating to the oxidation of unsaturated aldehydes | |
| GB655074A (en) | An improved process for the preparation of terephthalic acid | |
| GB948687A (en) | Process for producing acrylic acid and acrylic acid methyl ester | |
| US2341339A (en) | Oxidation of acrolein to acrylic acid | |
| US2259895A (en) | Process for manufacture of aliphatic carboxylic acid anhydrides | |
| Raacke-Fels et al. | THE INFLUENCE OF MOLYBDATES ON THE HYDROGEN PEROXIDE OXIDATION OF NAPHTHALENE AND β-NAPHTHOL1 | |
| GB1031229A (en) | Process for the manufacture of saturated aliphatic percarboxylic acids | |
| US2212509A (en) | Method of esterifying phenolic hydroxyls | |
| US2014310A (en) | Esters of 2-butyloctanol | |
| GB953775A (en) | Processes for the preparation of sorbic acid and alkyl esters of sorbic acid | |
| US2389187A (en) | Oxidation of organic compounds | |
| GB573334A (en) | Improvements in or relating to the manufacture of hydroxy acids | |
| GB573723A (en) | Improvements in or relating to the manufacture of polymerisable unsaturated acids | |
| GB461808A (en) | Improvements in the production of acetic anhydride | |
| GB742282A (en) | Process for producing unsaturated carboxylic acids | |
| GB572752A (en) | A process for the preparation of ª€-valerolactone | |
| US2439212A (en) | Dithiadecane diester | |
| GB482736A (en) | Process for the manufacture of methacrylic acid and esters thereof | |
| GB814360A (en) | Improvements in the production of esters of tertiary alcohols with unsaturated acids | |
| GB765903A (en) | Partial epoxidation of naturally occurring oils | |
| GB577992A (en) | Production of allyl alcohol and esters thereof | |
| GB992017A (en) | Process for the manufacture of peracetic acid | |
| GB830671A (en) | Process for oxidizing glutaraldehydes |