GB1060750A – Processes for preparing alkyl hydroxyalkyl fumarates
– Google Patents
GB1060750A – Processes for preparing alkyl hydroxyalkyl fumarates
– Google Patents
Processes for preparing alkyl hydroxyalkyl fumarates
Info
Publication number
GB1060750A
GB1060750A
GB30612/64A
GB3061264A
GB1060750A
GB 1060750 A
GB1060750 A
GB 1060750A
GB 30612/64 A
GB30612/64 A
GB 30612/64A
GB 3061264 A
GB3061264 A
GB 3061264A
GB 1060750 A
GB1060750 A
GB 1060750A
Authority
GB
United Kingdom
Prior art keywords
fumarate
alkyl
ethyl
hydrocarbon
fumarates
Prior art date
1963-07-19
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
Application number
GB30612/64A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Monsanto Co
Original Assignee
Monsanto Co
Priority date (The priority date 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 date listed.)
1963-07-19
Filing date
1964-08-04
Publication date
1967-03-08
1964-08-04
Application filed by Monsanto Co
filed
Critical
Monsanto Co
1967-03-08
Publication of GB1060750A
publication
Critical
patent/GB1060750A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
-1
alkyl hydroxyalkyl fumarates
Chemical class
0.000
title
abstract
4
125000000217
alkyl group
Chemical group
0.000
abstract
3
239000003054
catalyst
Substances
0.000
abstract
3
239000004215
Carbon black (E152)
Substances
0.000
abstract
2
VZCYOOQTPOCHFL-OWOJBTEDSA-N
Fumaric acid
Chemical compound
OC(=O)\C=C\C(O)=O
VZCYOOQTPOCHFL-OWOJBTEDSA-N
0.000
abstract
2
150000001412
amines
Chemical class
0.000
abstract
2
229910052751
metal
Inorganic materials
0.000
abstract
2
239000002184
metal
Substances
0.000
abstract
2
VZCYOOQTPOCHFL-UHFFFAOYSA-N
trans-butenedioic acid
Natural products
OC(=O)C=CC(O)=O
VZCYOOQTPOCHFL-UHFFFAOYSA-N
0.000
abstract
2
XLYMOEINVGRTEX-ONEGZZNKSA-N
(e)-4-ethoxy-4-oxobut-2-enoic acid
Chemical compound
CCOC(=O)\C=C\C(O)=O
XLYMOEINVGRTEX-ONEGZZNKSA-N
0.000
abstract
1
BGUIZQYQWQACDW-ONEGZZNKSA-N
1-o-ethyl 4-o-(2-hydroxyethyl) (e)-but-2-enedioate
Chemical compound
CCOC(=O)\C=C\C(=O)OCCO
BGUIZQYQWQACDW-ONEGZZNKSA-N
0.000
abstract
1
YDNGCTSTTCCHQE-UHFFFAOYSA-N
C(C)/C(/C(=O)O)=CC(=O)O.C(C)/C(/C(=O)O)=CC(=O)O.C(CO)O
Chemical compound
C(C)/C(/C(=O)O)=CC(=O)O.C(C)/C(/C(=O)O)=CC(=O)O.C(CO)O
YDNGCTSTTCCHQE-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
GOOHAUXETOMSMM-UHFFFAOYSA-N
Propylene oxide
Chemical class
CC1CO1
GOOHAUXETOMSMM-UHFFFAOYSA-N
0.000
abstract
1
229910052783
alkali metal
Inorganic materials
0.000
abstract
1
150000001340
alkali metals
Chemical class
0.000
abstract
1
229910052784
alkaline earth metal
Inorganic materials
0.000
abstract
1
150000001342
alkaline earth metals
Chemical class
0.000
abstract
1
150000001408
amides
Chemical class
0.000
abstract
1
125000003118
aryl group
Chemical group
0.000
abstract
1
125000001495
ethyl group
Chemical group
[H]C([H])([H])C([H])([H])*
0.000
abstract
1
VZCYOOQTPOCHFL-OWOJBTEDSA-L
fumarate(2-)
Chemical class
[O-]C(=O)\C=C\C([O-])=O
VZCYOOQTPOCHFL-OWOJBTEDSA-L
0.000
abstract
1
XLYMOEINVGRTEX-UHFFFAOYSA-N
fumaric acid monoethyl ester
Natural products
CCOC(=O)C=CC(O)=O
XLYMOEINVGRTEX-UHFFFAOYSA-N
0.000
abstract
1
229930195733
hydrocarbon
Natural products
0.000
abstract
1
125000002768
hydroxyalkyl group
Chemical group
0.000
abstract
1
238000011065
in-situ storage
Methods
0.000
abstract
1
150000003003
phosphines
Chemical class
0.000
abstract
1
150000003856
quaternary ammonium compounds
Chemical class
0.000
abstract
1
239000002904
solvent
Substances
0.000
abstract
1
Classifications
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C67/00—Preparation of carboxylic acid esters
C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
Abstract
An alkyl hydroxyalkyl fumarate is prepared by reacting a 1:2-alkylene oxide with an alkyl hydrogen fumarate in the presence of a catalyst selected from alkyl metal fumarates, aromatic N-heterocyclic amines, tri-hydrocarbon-substituted amines, di – hydrocarbon – substituted amides, hydroxyalkyl amines, quaternary ammonium compounds, amine oxides and tri-hydrocarbon substituted phosphines. Many alkyl fumarates are specified and ethylene or propylene oxides are preferred. The alkyl metal fumarate catalyst may be prepared in situ and alkali metal or alkaline earth metals are mentioned. The reaction may be with or without solvents, continuous or batchwise. Examples describe the preparation of ethyl 2-hydroxyethyl fumarate together with ethyl 2-(21-hydroxyethoxy) ethyl fumarate, and ethylene glycol bis (ethyl fumarate) using many of the catalysts specified.
GB30612/64A
1963-07-19
1964-08-04
Processes for preparing alkyl hydroxyalkyl fumarates
Expired
GB1060750A
(en)
Applications Claiming Priority (2)
Application Number
Priority Date
Filing Date
Title
US296387A
US3360544A
(en)
1963-07-19
1963-07-19
Processes for preparing alkyl hydroxyalkyl fumarates
US31851763A
1963-10-24
1963-10-24
Publications (1)
Publication Number
Publication Date
GB1060750A
true
GB1060750A
(en)
1967-03-08
Family
ID=26969628
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB30612/64A
Expired
GB1060750A
(en)
1963-07-19
1964-08-04
Processes for preparing alkyl hydroxyalkyl fumarates
Country Status (2)
Country
Link
US
(1)
US3360544A
(en)
GB
(1)
GB1060750A
(en)
Cited By (5)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US4757097A
(en)
*
1986-06-24
1988-07-12
Bayer Aktiengesellschaft
Process for the production of oligoesters containing hydroxy groups and their use
EP0345719A2
(en)
*
1988-06-10
1989-12-13
Chemische Fabrik Stockhausen GmbH
Compounds containing at least three functional ester groups, and process for their preparation
US5922658A
(en)
*
1996-09-06
1999-07-13
Exxon Chemical Patents Inc.
Two-cycle engine oil formed from a blend of a complex alcohol ester and other basestocks
US5942475A
(en)
*
1996-09-06
1999-08-24
Exxon Chemical Patents Inc.
Engine oil lubricants formed from complex alcohol esters
US5994278A
(en)
*
1996-09-06
1999-11-30
Exxon Chemical Patents Inc.
Blends of lubricant basestocks with high viscosity complex alcohol esters
Families Citing this family (2)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US3974083A
(en)
*
1974-03-29
1976-08-10
American Cyanamid Company
Control of corrosion and scale in circulating water systems by means of partial esters of polyfunctional organic acids
US8580864B2
(en)
*
2006-05-04
2013-11-12
Air Products And Chemicals, Inc.
Trimer catalysts with improved processability and surface cure
Family Cites Families (5)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US2386446A
(en)
*
1942-01-26
1945-10-09
Petrolite Corp
Composition of matter
US2910490A
(en)
*
1956-10-16
1959-10-27
Jefferson Chem Co Inc
Process for preparing glycol monoesters of organic carboxylic acids
US2929835A
(en)
*
1957-06-06
1960-03-22
Firestone Tire & Rubber Co
Reacting an alkylene oxide with an acrylic-type acid using an alkaline organic or inorganic catalyst
NL113424C
(en)
*
1958-08-01
NL278451A
(en)
*
1961-06-08
1963
1963-07-19
US
US296387A
patent/US3360544A/en
not_active
Expired – Lifetime
1964
1964-08-04
GB
GB30612/64A
patent/GB1060750A/en
not_active
Expired
Cited By (9)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US4757097A
(en)
*
1986-06-24
1988-07-12
Bayer Aktiengesellschaft
Process for the production of oligoesters containing hydroxy groups and their use
EP0345719A2
(en)
*
1988-06-10
1989-12-13
Chemische Fabrik Stockhausen GmbH
Compounds containing at least three functional ester groups, and process for their preparation
WO1989012040A1
(en)
*
1988-06-10
1989-12-14
Chemische Fabrik Stockhausen Gmbh
Compounds containing at least three functional ester groups and process for producing them
EP0345719A3
(en)
*
1988-06-10
1989-12-20
Chemische Fabrik Stockhausen Gmbh
Compounds containing at least three functional ester groups, and process for their preparation
JPH03504973A
(en)
*
1988-06-10
1991-10-31
ヒェミッシェ ファブリーク シュトックハウセン ゲー．エム．ベー．ハー
Compounds having at least 3 ester functional groups and methods for producing the same
US5177249A
(en)
*
1988-06-10
1993-01-05
Chemische Fabrik Stockhausen Gmbh
Compounds with at least three functional ester groups and process for the production thereof
US5922658A
(en)
*
1996-09-06
1999-07-13
Exxon Chemical Patents Inc.
Two-cycle engine oil formed from a blend of a complex alcohol ester and other basestocks
US5942475A
(en)
*
1996-09-06
1999-08-24
Exxon Chemical Patents Inc.
Engine oil lubricants formed from complex alcohol esters
US5994278A
(en)
*
1996-09-06
1999-11-30
Exxon Chemical Patents Inc.
Blends of lubricant basestocks with high viscosity complex alcohol esters
Also Published As
Publication number
Publication date
US3360544A
(en)
1967-12-26
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