CA1176657A - Production of carboxylic acids from acylium anions formed by carbonylation - Google Patents
Production of carboxylic acids from acylium anions formed by carbonylationInfo
- Publication number
- CA1176657A CA1176657A CA000404467A CA404467A CA1176657A CA 1176657 A CA1176657 A CA 1176657A CA 000404467 A CA000404467 A CA 000404467A CA 404467 A CA404467 A CA 404467A CA 1176657 A CA1176657 A CA 1176657A
- Authority
- CA
- Canada
- Prior art keywords
- fluoride
- recited
- acid
- acyl
- ninety
- 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
- 150000001450 anions Chemical class 0.000 title claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 title description 6
- 238000005810 carbonylation reaction Methods 0.000 title description 3
- 230000006315 carbonylation Effects 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001265 acyl fluorides Chemical class 0.000 claims abstract description 39
- 239000002253 acid Substances 0.000 claims abstract description 33
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- FSQOYWQCIXSBNP-UHFFFAOYSA-N 2-methylpropanoyl fluoride Chemical compound CC(C)C(F)=O FSQOYWQCIXSBNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 18
- -1 isobutyric acid Chemical class 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 33
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 32
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 32
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 27
- 238000006460 hydrolysis reaction Methods 0.000 claims description 25
- 150000002894 organic compounds Chemical class 0.000 claims description 22
- 230000007062 hydrolysis Effects 0.000 claims description 19
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 9
- 150000001336 alkenes Chemical class 0.000 claims description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 4
- WVRPFQGZHKZCEB-UHFFFAOYSA-N Isopropyl 2-methylpropanoate Chemical compound CC(C)OC(=O)C(C)C WVRPFQGZHKZCEB-UHFFFAOYSA-N 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 229940024423 isopropyl isobutyrate Drugs 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 5
- 239000007788 liquid Substances 0.000 claims 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 2
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims 2
- WGCJTTUVWKJDAX-UHFFFAOYSA-N 1-fluoro-2-methylpropane Chemical compound CC(C)CF WGCJTTUVWKJDAX-UHFFFAOYSA-N 0.000 claims 1
- IJMWOMHMDSDKGK-UHFFFAOYSA-N Isopropyl propionate Chemical compound CCC(=O)OC(C)C IJMWOMHMDSDKGK-UHFFFAOYSA-N 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002895 organic esters Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000567 combustion gas Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940099990 ogen Drugs 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/04—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid halides
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27069881A | 1981-06-05 | 1981-06-05 | |
| US270,698 | 1981-06-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1176657A true CA1176657A (en) | 1984-10-23 |
Family
ID=23032417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000404467A Expired CA1176657A (en) | 1981-06-05 | 1982-06-04 | Production of carboxylic acids from acylium anions formed by carbonylation |
Country Status (12)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0101719B1 (en) * | 1982-02-18 | 1987-05-06 | Ashland Oil, Inc. | Formation of isobutyric acid or methyl isobutyrate |
| DE3213395A1 (de) * | 1982-04-10 | 1983-10-13 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von isobuttersaeurefluorid bzw. isobuttersaeure |
| JPH07327833A (ja) * | 1994-06-07 | 1995-12-19 | Morii Kinzoku Kogyo Kk | 鍋類、湯沸し類等の容器 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL302250A (enrdf_load_stackoverflow) * | 1963-01-21 | |||
| GB1120714A (en) * | 1965-07-22 | 1968-07-24 | Distillers Co Yeast Ltd | Improvements in or relating to the production of carboxylic acids |
| NL6816940A (enrdf_load_stackoverflow) * | 1967-11-28 | 1969-05-30 | ||
| BE755997A (fr) * | 1969-09-11 | 1971-03-10 | Bp Chem Int Ltd | Production d'acides dicarboxyliques |
| US3661951A (en) * | 1969-12-01 | 1972-05-09 | Armour Ind Chem Co | Carboxylation of olefins |
| DE2406223A1 (de) * | 1974-02-09 | 1975-08-21 | Basf Ag | Verfahren zur herstellung von carbonsaeuren |
| DE3067475D1 (en) * | 1979-12-20 | 1984-05-17 | Roehm Gmbh | Process for the production of isobutyric acid or its lower alkyl esters |
-
1982
- 1982-06-04 GB GB8216301A patent/GB2099821B/en not_active Expired
- 1982-06-04 AU AU84606/82A patent/AU532972B2/en not_active Ceased
- 1982-06-04 BE BE0/208269A patent/BE893417A/fr not_active IP Right Cessation
- 1982-06-04 KR KR8202509A patent/KR850001913B1/ko not_active Expired
- 1982-06-04 CH CH3475/82A patent/CH657122A5/de not_active IP Right Cessation
- 1982-06-04 NL NLAANVRAGE8202270,A patent/NL186959C/xx not_active IP Right Cessation
- 1982-06-04 CA CA000404467A patent/CA1176657A/en not_active Expired
- 1982-06-04 DE DE3221174A patent/DE3221174C2/de not_active Expired
- 1982-06-04 JP JP57096067A patent/JPS6024086B2/ja not_active Expired
- 1982-06-04 IT IT8221708A patent/IT1210894B/it active
- 1982-06-04 FR FR8209807A patent/FR2507179A1/fr active Granted
- 1982-06-07 AT AT0220282A patent/AT389694B/de not_active IP Right Cessation
-
1984
- 1984-02-09 GB GB08403476A patent/GB2134113B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| KR840000462A (ko) | 1984-02-22 |
| GB2134113A (en) | 1984-08-08 |
| JPS57212134A (en) | 1982-12-27 |
| BE893417A (fr) | 1982-10-01 |
| JPS6024086B2 (ja) | 1985-06-11 |
| GB2134113B (en) | 1985-11-20 |
| NL186959C (nl) | 1991-04-16 |
| GB2099821A (en) | 1982-12-15 |
| IT1210894B (it) | 1989-09-29 |
| KR850001913B1 (ko) | 1985-12-31 |
| GB2099821B (en) | 1985-10-23 |
| CH657122A5 (de) | 1986-08-15 |
| NL8202270A (nl) | 1983-01-03 |
| ATA220282A (de) | 1989-06-15 |
| AU532972B2 (en) | 1983-10-20 |
| DE3221174C2 (de) | 1985-06-20 |
| DE3221174A1 (de) | 1982-12-23 |
| FR2507179B1 (enrdf_load_stackoverflow) | 1985-05-17 |
| IT8221708A0 (it) | 1982-06-04 |
| AT389694B (de) | 1990-01-10 |
| NL186959B (nl) | 1990-11-16 |
| FR2507179A1 (fr) | 1982-12-10 |
| AU8460682A (en) | 1982-12-09 |
| GB8403476D0 (en) | 1984-03-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |