DE2750719A1 - Verfahren zur herstellung von isobuttersaeure - Google Patents
Verfahren zur herstellung von isobuttersaeureInfo
- Publication number
- DE2750719A1 DE2750719A1 DE19772750719 DE2750719A DE2750719A1 DE 2750719 A1 DE2750719 A1 DE 2750719A1 DE 19772750719 DE19772750719 DE 19772750719 DE 2750719 A DE2750719 A DE 2750719A DE 2750719 A1 DE2750719 A1 DE 2750719A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- carboxylic acid
- isobutyric acid
- acid
- propylene
- 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.)
- Granted
Links
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 title claims abstract description 67
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 title claims abstract description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title abstract description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 title abstract description 11
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title description 3
- 229910052796 boron Inorganic materials 0.000 title description 3
- 238000005810 carbonylation reaction Methods 0.000 title description 3
- 230000006315 carbonylation Effects 0.000 title description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title 2
- 150000002148 esters Chemical class 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- -1 isopropyl ester Chemical class 0.000 claims abstract description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 26
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 18
- 229910015900 BF3 Inorganic materials 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 150000001735 carboxylic acids Chemical class 0.000 claims description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- VPLWTTJJBXGWSU-UHFFFAOYSA-N C=CC.C(C(C)C)(=O)O Chemical group C=CC.C(C(C)C)(=O)O VPLWTTJJBXGWSU-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- 239000003054 catalyst Substances 0.000 abstract description 6
- 229960000583 acetic acid Drugs 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 150000008064 anhydrides Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- WVRPFQGZHKZCEB-UHFFFAOYSA-N Isopropyl 2-methylpropanoate Chemical compound CC(C)OC(=O)C(C)C WVRPFQGZHKZCEB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229940024423 isopropyl isobutyrate Drugs 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HKBWUGPHBIJXBY-UHFFFAOYSA-N 2,2,3,5,5-pentamethyloxolane Chemical compound CC1CC(C)(C)OC1(C)C HKBWUGPHBIJXBY-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- AVWLPUQJODERGA-UHFFFAOYSA-L cobalt(2+);diiodide Chemical compound [Co+2].[I-].[I-] AVWLPUQJODERGA-UHFFFAOYSA-L 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- MVJKXJPDBTXECY-UHFFFAOYSA-N trifluoroborane;hydrate Chemical compound O.FB(F)F MVJKXJPDBTXECY-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure 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
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
-
- 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
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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772750719 DE2750719A1 (de) | 1977-11-12 | 1977-11-12 | Verfahren zur herstellung von isobuttersaeure |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772750719 DE2750719A1 (de) | 1977-11-12 | 1977-11-12 | Verfahren zur herstellung von isobuttersaeure |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2750719A1 true DE2750719A1 (de) | 1979-05-17 |
| DE2750719C2 DE2750719C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-06-04 |
Family
ID=6023624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772750719 Granted DE2750719A1 (de) | 1977-11-12 | 1977-11-12 | Verfahren zur herstellung von isobuttersaeure |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2750719A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2508441A1 (fr) * | 1981-06-29 | 1982-12-31 | Ashland Oil Inc | Procede pour produire un derive anionique d'acylium a partir de monoxyde de carbone, d'un acide anhydre et d'un compose organique susceptible d'addition de monoxyde de carbone |
| FR2512811A1 (fr) * | 1981-07-10 | 1983-03-18 | Ashland Oil Inc | Procede pour produire un derive anionique d'acylium et des acides et esters organiques en derivant |
| US4452999A (en) * | 1979-12-20 | 1984-06-05 | Rohm Gmbh | Method for making isobutyric acid |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2439951A1 (de) * | 1973-08-21 | 1975-02-27 | Monsanto Co | Verfahren zur herstellung von propionsaeure |
-
1977
- 1977-11-12 DE DE19772750719 patent/DE2750719A1/de active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2439951A1 (de) * | 1973-08-21 | 1975-02-27 | Monsanto Co | Verfahren zur herstellung von propionsaeure |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4452999A (en) * | 1979-12-20 | 1984-06-05 | Rohm Gmbh | Method for making isobutyric acid |
| US4647696A (en) * | 1979-12-20 | 1987-03-03 | Rohm Gmbh | Method for making isobutyric acid |
| FR2508441A1 (fr) * | 1981-06-29 | 1982-12-31 | Ashland Oil Inc | Procede pour produire un derive anionique d'acylium a partir de monoxyde de carbone, d'un acide anhydre et d'un compose organique susceptible d'addition de monoxyde de carbone |
| FR2512811A1 (fr) * | 1981-07-10 | 1983-03-18 | Ashland Oil Inc | Procede pour produire un derive anionique d'acylium et des acides et esters organiques en derivant |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2750719C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-06-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |