GB969017A - A process for the preparation of alkenyl esters of carboxylic acids - Google Patents
A process for the preparation of alkenyl esters of carboxylic acidsInfo
- Publication number
- GB969017A GB969017A GB928861A GB928861A GB969017A GB 969017 A GB969017 A GB 969017A GB 928861 A GB928861 A GB 928861A GB 928861 A GB928861 A GB 928861A GB 969017 A GB969017 A GB 969017A
- Authority
- GB
- United Kingdom
- Prior art keywords
- salts
- carboxylic acids
- olefines
- palladium
- carboxylic
- 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 5
- 125000003342 alkenyl group Chemical group 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 abstract 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical class [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 150000002940 palladium Chemical class 0.000 abstract 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 abstract 2
- -1 platinum group metals Chemical class 0.000 abstract 2
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 150000001868 cobalt Chemical class 0.000 abstract 1
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 238000005336 cracking Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002736 metal compounds Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052763 palladium Chemical class 0.000 abstract 1
- 150000002942 palmitic acid derivatives Chemical class 0.000 abstract 1
- 125000005498 phthalate group Chemical class 0.000 abstract 1
- 229950010765 pivalate Drugs 0.000 abstract 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 150000003890 succinate salts Chemical class 0.000 abstract 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 abstract 1
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 1
- 239000004291 sulphur dioxide Substances 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
- C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
a , b alkenyl esters of carboxylic acids are prepared by reacting olefines with salts of carboxylic acids and palladium and platinum group metals, in a substantially non-aqueous liquid medium. Ethylene, propylene, 1- and 2-butylene, 1-pentene, olefines from the polymerization or copolymerization of ethylene and/or propylene, olefines from the cracking of paraffins, butadiene and isoprene are referred to and a salt of carboxylates such as acetate, propionate, butyrate, pivalate, palmitates, stearates, benzoates, succinates, adipates, phthalates, terephthalates and mixtures thereof, or those derived from carboxylic acids with the carboxylic group directly linked to a t- or quaternary carbon atom such as is prepared by the reaction of olefines and carbon monoxide, preferably a palladium salt, may be used. Salts of alkali and/or alkaline earth metals and carboxylic acids may be present in the medium which may be liquid sulphur dioxide, thiocyclopentane-1, 1-dioxide, a ketone, hydrocarbon, halogenated hydrocarbon, or ester, amide, ether, a nitrile or a nitro compound. The metal compounds may be reoxidised, preferably in the presence of a promotor, nitrogen dioxide, or of metallic salts comprising redox systems such as copper, iron or cobalt salts of carboxylic acid, under oxygen pressure and the water formed removed before recirculation. Examples describe the preparation of vinyl acetate and the vinyl ester of a branched carboxylic acid obtained by the reaction of an 8-10C. olefine with carbon monoxide, using the palladium salts of the respective acids, together with the sodium salts. Specification 969,018 is referred to.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB928861A GB969017A (en) | 1961-03-14 | 1961-03-14 | A process for the preparation of alkenyl esters of carboxylic acids |
| CA844,367A CA958030A (en) | 1961-03-14 | 1962-03-14 | Production of alkenyl carboxylates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB928861A GB969017A (en) | 1961-03-14 | 1961-03-14 | A process for the preparation of alkenyl esters of carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB969017A true GB969017A (en) | 1964-09-09 |
Family
ID=9869095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB928861A Expired GB969017A (en) | 1961-03-14 | 1961-03-14 | A process for the preparation of alkenyl esters of carboxylic acids |
Country Status (2)
| Country | Link |
|---|---|
| CA (1) | CA958030A (en) |
| GB (1) | GB969017A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3548021A (en) * | 1968-06-27 | 1970-12-15 | Union Oil Co | Production of paraxylene |
| US4602103A (en) * | 1984-10-29 | 1986-07-22 | Sun Refining And Marketing Company | Process for the oxidation of butenes to linear acetates |
| WO2003024914A1 (en) * | 2001-09-14 | 2003-03-27 | Resolution Research Nederland B.V. | Manufacture of allyl esters of tertiary alkane carboxylic acids |
-
1961
- 1961-03-14 GB GB928861A patent/GB969017A/en not_active Expired
-
1962
- 1962-03-14 CA CA844,367A patent/CA958030A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3548021A (en) * | 1968-06-27 | 1970-12-15 | Union Oil Co | Production of paraxylene |
| US4602103A (en) * | 1984-10-29 | 1986-07-22 | Sun Refining And Marketing Company | Process for the oxidation of butenes to linear acetates |
| WO2003024914A1 (en) * | 2001-09-14 | 2003-03-27 | Resolution Research Nederland B.V. | Manufacture of allyl esters of tertiary alkane carboxylic acids |
Also Published As
| Publication number | Publication date |
|---|---|
| CA958030A (en) | 1974-11-19 |
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