DE2951289A1 - Verfahren zur herstellung von isobuttersaeure - Google Patents
Verfahren zur herstellung von isobuttersaeureInfo
- Publication number
- DE2951289A1 DE2951289A1 DE19792951289 DE2951289A DE2951289A1 DE 2951289 A1 DE2951289 A1 DE 2951289A1 DE 19792951289 DE19792951289 DE 19792951289 DE 2951289 A DE2951289 A DE 2951289A DE 2951289 A1 DE2951289 A1 DE 2951289A1
- Authority
- DE
- Germany
- Prior art keywords
- koch
- acid
- isobutyric acid
- isopropyl formate
- synthesis
- 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- Withdrawn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
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 title claims abstract description 42
- RMOUBSOVHSONPZ-UHFFFAOYSA-N Isopropyl formate Chemical compound CC(C)OC=O RMOUBSOVHSONPZ-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 12
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 11
- 229910052500 inorganic mineral Inorganic materials 0.000 title claims abstract description 4
- 239000011707 mineral Substances 0.000 title claims abstract description 4
- 239000003377 acid catalyst Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 11
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 5
- -1 isopropyl ester Chemical class 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 229910015900 BF3 Inorganic materials 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000006315 carbonylation Effects 0.000 description 2
- 238000005810 carbonylation reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VRERFCZMTJEUTK-UHFFFAOYSA-N 2-methylpentan-2-yl formate Chemical compound CCCC(C)(C)OC=O VRERFCZMTJEUTK-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- CUPFNGOKRMWUOO-UHFFFAOYSA-N hydron;difluoride Chemical group F.F CUPFNGOKRMWUOO-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 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
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
- C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
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)
- Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792951289 DE2951289A1 (de) | 1979-12-20 | 1979-12-20 | Verfahren zur herstellung von isobuttersaeure |
| EP80107045A EP0031886B1 (de) | 1979-12-20 | 1980-11-14 | Verfahren zur Herstellung von Isobuttersäure oder ihrer niederen Alkylester |
| DE8080107045T DE3067475D1 (en) | 1979-12-20 | 1980-11-14 | Process for the production of isobutyric acid or its lower alkyl esters |
| JP17909680A JPS5695146A (en) | 1979-12-20 | 1980-12-19 | Manufacture of isoethylacetic acid |
| US06/380,609 US4452999A (en) | 1979-12-20 | 1982-05-21 | Method for making isobutyric acid |
| US06/474,799 US4647696A (en) | 1979-12-20 | 1983-03-14 | Method for making isobutyric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792951289 DE2951289A1 (de) | 1979-12-20 | 1979-12-20 | Verfahren zur herstellung von isobuttersaeure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2951289A1 true DE2951289A1 (de) | 1981-07-02 |
Family
ID=6088997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792951289 Withdrawn DE2951289A1 (de) | 1979-12-20 | 1979-12-20 | Verfahren zur herstellung von isobuttersaeure |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5695146A (forum.php) |
| DE (1) | DE2951289A1 (forum.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3033655A1 (de) * | 1980-09-06 | 1982-04-22 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von isobuttersaeure |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3332436T1 (de) * | 1982-02-18 | 1984-12-13 | Ashland Oil Inc., Columbus, Ohio | Bildung von Isobuttersäure oder Methylisobutyrat |
| JP2526614B2 (ja) * | 1987-12-21 | 1996-08-21 | 三菱瓦斯化学株式会社 | イソ酪酸の製造方法 |
| DE102004011081A1 (de) * | 2004-03-06 | 2005-09-22 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von tertiären Carbonsäuren |
| JP5044947B2 (ja) * | 2005-03-10 | 2012-10-10 | 三菱瓦斯化学株式会社 | カルボン酸あるいはカルボン酸エステルの製造方法 |
-
1979
- 1979-12-20 DE DE19792951289 patent/DE2951289A1/de not_active Withdrawn
-
1980
- 1980-12-19 JP JP17909680A patent/JPS5695146A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3033655A1 (de) * | 1980-09-06 | 1982-04-22 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von isobuttersaeure |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0131496B2 (forum.php) | 1989-06-26 |
| JPS5695146A (en) | 1981-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |