GB1010175A - Process for preparing esters - Google Patents
Process for preparing estersInfo
- Publication number
- GB1010175A GB1010175A GB20654/62A GB2065462A GB1010175A GB 1010175 A GB1010175 A GB 1010175A GB 20654/62 A GB20654/62 A GB 20654/62A GB 2065462 A GB2065462 A GB 2065462A GB 1010175 A GB1010175 A GB 1010175A
- Authority
- GB
- United Kingdom
- Prior art keywords
- organic
- arsenic
- catalyst
- acid
- organic acid
- 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
- 150000002148 esters Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000007524 organic acids Chemical class 0.000 abstract 6
- 229910052785 arsenic Inorganic materials 0.000 abstract 4
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 abstract 4
- 150000001621 bismuth Chemical class 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 abstract 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- -1 butyl alcohols Chemical class 0.000 abstract 3
- FUXMTEKFGUWSNC-UHFFFAOYSA-N 2,3,4,5-tetrachlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C(Cl)=C1Cl FUXMTEKFGUWSNC-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 2
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 abstract 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 2
- 150000002888 oleic acid derivatives Chemical class 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 abstract 1
- QNSFQIRYXVVLGT-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;2-ethyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(C)(C)CO.CCC(CO)(CO)CO QNSFQIRYXVVLGT-UHFFFAOYSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 1
- 229930195725 Mannitol Natural products 0.000 abstract 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001559 benzoic acids Chemical class 0.000 abstract 1
- RHGQOMYDGHIKFH-GNOQXXQHSA-K bis[[(z)-octadec-9-enoyl]oxy]bismuthanyl (z)-octadec-9-enoate Chemical compound [Bi+3].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O RHGQOMYDGHIKFH-GNOQXXQHSA-K 0.000 abstract 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 239000000594 mannitol Substances 0.000 abstract 1
- 235000010355 mannitol Nutrition 0.000 abstract 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 abstract 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 235000013772 propylene glycol Nutrition 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/68—Arsenic compounds without As—C bonds
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/94—Bismuth compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/49—Esterification or transesterification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Polyesterification reactions are carried out in the presence, as a catalyst, of an arsenic or bismuth salt of an organic acid. The catalyst may be an arsenic or bismuth salt of 2-ethylhexoic, acetic, tallic, pelargonic, oleic, lauric, phthalic, oxalic, tetrachlorobenzoic, stearic, propionic, sebacic or azelaic acid, and is preferably used in an amount of 0.01 to 1% by weight of the reactants. The invention is illustrated by the polyesterification reaction of neopentyl glycol with adipic acid in the presence of bismuth trioleate.ALSO:Esterification reactions comprising reacting an organic hydroxy compound with an organic acid, an organic anhydride or a half ester of a dibasic organic acid, and transesterification reactions comprising reacting an ester of an organic acid and a highly volatile alcohol with a less volatile alcohol, are carried out in the presence, as a catalyst, of an arsenic or bismuth salt of an organic acid. The catalyst may be an arsenic or bismuth salt of 2-ethylhexoic, acetic, tallic, pelargonic, oleic, lauric, phthalic, oxalic, stearic, tetrachlorobenzoic, propionic, sebacic or azelaic acid, and is preferably used in an amount of 0.01 to 1% by weight of the reactants. Organic hydroxy compounds are, for example, butyl alcohols, amyl alcohols, isooctyl alcohols, ethylene glycol, propylene glycols, butylene glycols, neopentyl glycol trimethylol propane, sorbitol and mannitol. Organic acids are, for example, adipic, butyric, sebacic, maleic, tetrachlorophthalic, phthalic, cyclohexane carboxylic, 1,4-cyclohexane dicarboxylic, terephthalic, benzoic and paramethyl benzoic acids.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11305761A | 1961-05-29 | 1961-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1010175A true GB1010175A (en) | 1965-11-17 |
Family
ID=22347388
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20654/62A Expired GB1010175A (en) | 1961-05-29 | 1962-05-29 | Process for preparing esters |
| GB16335/65A Expired GB1011660A (en) | 1961-05-29 | 1962-05-29 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16335/65A Expired GB1011660A (en) | 1961-05-29 | 1962-05-29 |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH397634A (en) |
| DE (1) | DE1258408B (en) |
| GB (2) | GB1010175A (en) |
| NL (1) | NL279071A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3312427A1 (en) * | 1983-04-07 | 1984-10-11 | Henkel KGaA, 4000 Düsseldorf | METHOD FOR PRODUCING 2-CYANACRYLATES FROM 2,4-DICYANGLUTARATES |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1039748B (en) * | 1953-06-30 | 1958-09-25 | Bayer Ag | Process for the production of polyesters |
| DE1103335B (en) * | 1955-10-13 | 1961-03-30 | Goodrich Co B F | Process for the production of carboxylic acid esters |
-
0
- NL NL279071D patent/NL279071A/xx unknown
-
1962
- 1962-05-25 DE DEM52983A patent/DE1258408B/en active Pending
- 1962-05-28 CH CH644162A patent/CH397634A/en unknown
- 1962-05-29 GB GB20654/62A patent/GB1010175A/en not_active Expired
- 1962-05-29 GB GB16335/65A patent/GB1011660A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL279071A (en) | 1900-01-01 |
| GB1011660A (en) | 1965-12-01 |
| DE1258408B (en) | 1968-01-11 |
| CH397634A (en) | 1965-08-31 |
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