GB1191380A - Process for the preparation of Diesters of 1,2-Dicarboxylic Acids - Google Patents
Process for the preparation of Diesters of 1,2-Dicarboxylic AcidsInfo
- Publication number
- GB1191380A GB1191380A GB5093668A GB5093668A GB1191380A GB 1191380 A GB1191380 A GB 1191380A GB 5093668 A GB5093668 A GB 5093668A GB 5093668 A GB5093668 A GB 5093668A GB 1191380 A GB1191380 A GB 1191380A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mixture
- acid
- monoesters
- alcohols
- anhydride
- 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
- 150000005690 diesters Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 abstract 10
- 239000002253 acid Substances 0.000 abstract 5
- 150000001298 alcohols Chemical class 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 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
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- -1 aliphatic alcohols Chemical class 0.000 abstract 1
- 229910052787 antimony Inorganic materials 0.000 abstract 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract 1
- 229910052785 arsenic Inorganic materials 0.000 abstract 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 abstract 1
- 238000010533 azeotropic distillation Methods 0.000 abstract 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 150000002689 maleic acids Chemical class 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003444 succinic acids Chemical class 0.000 abstract 1
- 229910052723 transition metal Inorganic materials 0.000 abstract 1
- 150000003624 transition metals Chemical class 0.000 abstract 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1,191,380. Diesters of dicarboxylic acids; alcohols. SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ N.V. 28 Oct., 1968, No. 50936/68. Heading C2C. [Also in Division C3] Mixed diesters of a 1,2-dicarboxylic acid, together with the anhydride of the acid, are obtained by heating a mixture of monoesters of the acid to a temperature of at least 100‹ C. in the absence of alcohols and while removing the water formed, preferably by azeotropic distillation. The preferred starting materials are mixtures of monoesters of the acids with aliphatic alcohols of 6-11 carbon atoms, and such mixtures may be prepared by mixing appropriate monoesters of the acid or by monoesterifying the acid with an appropriate mixture of alcohols. Such a mixture may be obtained by reacting an olefine or olefine mixture with carbon monoxide and hydrogen in the presence of a catalyst complex comprising (a) a transition metal of atomic number between 23 and 85, preferably cobalt, and (b) a biphyllic ligand containing trivalent phosphorus, arsenic or antimony (see Specification 988,943). The diester-forming reaction may be effected in the presence of catalysts, among which zinc chloride and tetrabutyl orthotitanate are specified. The acid anhydride also produced in the process may be separated by filtration or extraction or it may be worked up by adding a mixture of alcohols to the reaction product to convert part or all of the anhydride into monoesters, which may then be treated in accordance with the invention. In Example 1, monoesters of phthalic acid are prepared by heating phthalic anhydride with an alcohol mixture prepared by reacting a mixture of olefines of 6-8 carbon atoms with carbon monoxide and hydrogen in the presence of a catalyst comprising dicobalt octacarbonyl and tri-n-butylphosphine, the mixture being then fractionated and the fractions being heated to 175‹ C. in the presence of xylene. The products of this example are useful as plasticizers for polyvinyl chloride (see Division C3). Other specified 1,2- dicarboxylic acids, the mono esters of which may be treated, are succinic and maleic acids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5093668A GB1191380A (en) | 1968-10-28 | 1968-10-28 | Process for the preparation of Diesters of 1,2-Dicarboxylic Acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5093668A GB1191380A (en) | 1968-10-28 | 1968-10-28 | Process for the preparation of Diesters of 1,2-Dicarboxylic Acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1191380A true GB1191380A (en) | 1970-05-13 |
Family
ID=10458013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5093668A Expired GB1191380A (en) | 1968-10-28 | 1968-10-28 | Process for the preparation of Diesters of 1,2-Dicarboxylic Acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1191380A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011041349A1 (en) * | 2009-09-29 | 2011-04-07 | Exxonmobil Research And Engineering Company | Phenylene oxo-diester plasticizers and methods of making |
| CN104418748A (en) * | 2013-08-22 | 2015-03-18 | 中国科学院大连化学物理研究所 | Method for preparation of diester phthalate by o-xylene liquid-phase oxidation and esterification coupling |
-
1968
- 1968-10-28 GB GB5093668A patent/GB1191380A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011041349A1 (en) * | 2009-09-29 | 2011-04-07 | Exxonmobil Research And Engineering Company | Phenylene oxo-diester plasticizers and methods of making |
| CN104418748A (en) * | 2013-08-22 | 2015-03-18 | 中国科学院大连化学物理研究所 | Method for preparation of diester phthalate by o-xylene liquid-phase oxidation and esterification coupling |
| CN104418748B (en) * | 2013-08-22 | 2016-03-23 | 中国科学院大连化学物理研究所 | A method for preparing phthalic acid diester by coupling liquid-phase oxidation and esterification of o-xylene |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |