GB1080867A - A process for the preparation of carboxylic acids and derivatives thereof - Google Patents
A process for the preparation of carboxylic acids and derivatives thereofInfo
- Publication number
- GB1080867A GB1080867A GB2974063A GB2974063A GB1080867A GB 1080867 A GB1080867 A GB 1080867A GB 2974063 A GB2974063 A GB 2974063A GB 2974063 A GB2974063 A GB 2974063A GB 1080867 A GB1080867 A GB 1080867A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- acid
- bis
- reaction
- metal
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 6
- 150000001336 alkenes Chemical class 0.000 abstract 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 6
- 150000004820 halides Chemical class 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- 229910052763 palladium Inorganic materials 0.000 abstract 4
- 239000000376 reactant Substances 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 150000008064 anhydrides Chemical class 0.000 abstract 3
- 229910052703 rhodium Inorganic materials 0.000 abstract 3
- 239000010948 rhodium Substances 0.000 abstract 3
- 229910052707 ruthenium Inorganic materials 0.000 abstract 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 238000011065 in-situ storage Methods 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 229910001507 metal halide Inorganic materials 0.000 abstract 2
- 150000005309 metal halides Chemical class 0.000 abstract 2
- 239000010970 precious metal Substances 0.000 abstract 2
- 239000012429 reaction media Substances 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- IGRURXZWJCSNKU-UHFFFAOYSA-N Isopropenylacetic acid Chemical compound CC(=C)CC(O)=O IGRURXZWJCSNKU-UHFFFAOYSA-N 0.000 abstract 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- 125000005595 acetylacetonate group Chemical group 0.000 abstract 1
- 229910001508 alkali metal halide Inorganic materials 0.000 abstract 1
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 229910052788 barium Inorganic materials 0.000 abstract 1
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 abstract 1
- OZQBDSLJTSETCK-UHFFFAOYSA-N but-3-enoyl but-3-enoate Chemical compound C=CCC(=O)OC(=O)CC=C OZQBDSLJTSETCK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052793 cadmium Inorganic materials 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract 1
- VUSWCWPCANWBFG-UHFFFAOYSA-N cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC=CC1 VUSWCWPCANWBFG-UHFFFAOYSA-N 0.000 abstract 1
- DJCGNGXZCYIMLT-UHFFFAOYSA-N cyclooct-3-ene-1-carbonyl chloride Chemical compound C1(CC=CCCCC1)C(=O)Cl DJCGNGXZCYIMLT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 150000002736 metal compounds Chemical class 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- UIUWNILCHFBLEQ-UHFFFAOYSA-N pent-3-enoic acid Chemical compound CC=CCC(O)=O UIUWNILCHFBLEQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/006—Palladium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—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
- C07C51/54—Preparation of carboxylic acid anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
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)
Abstract
Carboxylic acids, halides, anhydrides or esters thereof are prepared by reacting an olefin, optionally substituted by halogen, alkoxy or ester groups, with carbon monoxide in a substantially non-aqueous liquid medium and in the presence of a halide or p -complex of palladium, rhodium or ruthenium, said p -complex being derived from the halide of the metal and the olefin reactant, and optionally hydrolysing the resultant halide, anhydride or ester to the corresponding acid. Numerous olefin starting materials are specified, a preferred class being those containing allyl groups. In general, the reaction yields acid halides and anhydrides, but if the olefin reactant contains an ether linkage the initial product is an ester. The reaction product may contain halogen substituents orginating from the metal halide catalyst. The p -complex may be formed in situ from the metal halide and olefin reactant. The catalyst can be used to stoichiometric or greater quantities, but may also be employed in small amounts in combination with an oxidizing agent, e.g. HCl, O2, combined with a redox system, e.g. copper chloride, in order to regenerate any precious metal which is reduced. The reaction rate may be enhanced by the addition of other metal compounds, e.g. the carboxylates of alkali and alkaline earth metals, Cu, Fe, Al, Ba, Zn and Cd. Also alkali and/or alkaline earth metal halides may be used to increase the polarity of the reaction medium. A large number of substances are specified as suitable reaction media. The reaction may be effected within wide ranges of temperature and pressure, e.g. -80 DEG to 800 DEG C., 0.1 to 250 atmos. The carbon monoxide may be diluted with an inert gas, e.g. N2, CH4. Examples describe the preparation of acrylic acid, b -chloropropionic acid, 4,4,4-trichlorobutyric, b -chlorobutyric acid, b -dichloropropionic acid, b -chloroacrylic acid, vinylacetic acid, isopropenyl acetic acid, 3-pentenic acid, acetic anhydride, vinylacetic anhydride, 3-cyclohexene carboxylic acid and 3-cyclooctene carboxylic acid chloride. The p -complexes of Pd, Rh and Ru may be prepared in situ by reaction between the Pd, Rh or Ru chlorides and the olefin reactant. Alternatively, the complexes may be made in a separate step by reaction of the olefinic compound and a compound of the precious metal or the activated metal itself. Specified complexes are bis-(p -allylpalladium chloride), bis - (p - allylpalladium bromide), acetylacetonato - (allyl) palladium, bis - (p - isobutenylpalladium chloride), bis-(p -crotylpalladium chloride), bis - (p - crotylpalladium bromide), bis - (p - cyclohexenylpalladium chloride), bis - (p - 4 - chlorocrotylpalladium chloride), bis - (p - 2 - methyl - 4 - chlorocrotylpalladium chloride), p - allylcarbonylpalladium chloride, p - isobutenylcarbonylpalladium chloride, ethylenepalladium chloride and ethylenerhodium chloride.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2974063A GB1080867A (en) | 1963-07-26 | 1963-07-26 | A process for the preparation of carboxylic acids and derivatives thereof |
| DE19641468987 DE1468987A1 (en) | 1963-07-26 | 1964-07-24 | Process for the addition of carbon monoxide to unsaturated organic compounds |
| FR982857A FR1402383A (en) | 1963-07-26 | 1964-07-24 | Process for the preparation of carboxylic acids and their derivatives |
| NL6408476A NL6408476A (en) | 1963-07-26 | 1964-07-24 | |
| BE650980D BE650980A (en) | 1963-07-26 | 1964-07-24 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2974063A GB1080867A (en) | 1963-07-26 | 1963-07-26 | A process for the preparation of carboxylic acids and derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1080867A true GB1080867A (en) | 1967-08-23 |
Family
ID=10296402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2974063A Expired GB1080867A (en) | 1963-07-26 | 1963-07-26 | A process for the preparation of carboxylic acids and derivatives thereof |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE650980A (en) |
| DE (1) | DE1468987A1 (en) |
| GB (1) | GB1080867A (en) |
| NL (1) | NL6408476A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0640580A1 (en) * | 1993-07-26 | 1995-03-01 | E.I. Du Pont De Nemours And Company | Preparation of 3-pentenoic acid and a catalyst therefore |
| WO1995030637A1 (en) * | 1994-05-04 | 1995-11-16 | E.I. Du Pont De Nemours And Company | Catalyst recovery in the carbonylation of chlorobutenes to pentenoyl chloride |
| WO1997029069A1 (en) * | 1996-02-12 | 1997-08-14 | Dsm N.V. | Process for the preparation of pentenoic acid or pentenoate ester |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3415871A (en) * | 1965-08-09 | 1968-12-10 | Union Oil Co | Preparation of beta-acyloxy-carboxylic acids and alpha,beta-unsaturated carboxylic acids by oxidative carbonylation |
| US3530168A (en) * | 1966-08-30 | 1970-09-22 | Union Oil Co | Preparation of esters |
| US3505394A (en) * | 1966-10-04 | 1970-04-07 | Union Oil Co | Oxidative carbonylation |
| US3420873A (en) * | 1966-10-11 | 1969-01-07 | Union Oil Co | Oxidative carbonylation and catalyst recovery |
-
1963
- 1963-07-26 GB GB2974063A patent/GB1080867A/en not_active Expired
-
1964
- 1964-07-24 NL NL6408476A patent/NL6408476A/xx unknown
- 1964-07-24 BE BE650980D patent/BE650980A/xx unknown
- 1964-07-24 DE DE19641468987 patent/DE1468987A1/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0640580A1 (en) * | 1993-07-26 | 1995-03-01 | E.I. Du Pont De Nemours And Company | Preparation of 3-pentenoic acid and a catalyst therefore |
| WO1995030637A1 (en) * | 1994-05-04 | 1995-11-16 | E.I. Du Pont De Nemours And Company | Catalyst recovery in the carbonylation of chlorobutenes to pentenoyl chloride |
| WO1997029069A1 (en) * | 1996-02-12 | 1997-08-14 | Dsm N.V. | Process for the preparation of pentenoic acid or pentenoate ester |
Also Published As
| Publication number | Publication date |
|---|---|
| BE650980A (en) | 1965-01-25 |
| DE1468987A1 (en) | 1969-06-26 |
| NL6408476A (en) | 1965-01-27 |
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