GB1439234A – Vicinal glycol ester preparation process
– Google Patents
GB1439234A – Vicinal glycol ester preparation process
– Google Patents
Vicinal glycol ester preparation process
Info
Publication number
GB1439234A
GB1439234A
GB3773573A
GB3773573A
GB1439234A
GB 1439234 A
GB1439234 A
GB 1439234A
GB 3773573 A
GB3773573 A
GB 3773573A
GB 3773573 A
GB3773573 A
GB 3773573A
GB 1439234 A
GB1439234 A
GB 1439234A
Authority
GB
United Kingdom
Prior art keywords
cation
cations
basicity control
saturated
basicity
Prior art date
1972-08-09
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
GB3773573A
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.)
Halcon International Inc
Original Assignee
Halcon International Inc
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.)
1972-08-09
Filing date
1973-08-09
Publication date
1976-06-16
1973-08-09
Application filed by Halcon International Inc
filed
Critical
Halcon International Inc
1976-06-16
Publication of GB1439234A
publication
Critical
patent/GB1439234A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
-1
glycol ester
Chemical group
0.000
title
abstract
4
238000002360
preparation method
Methods
0.000
title
abstract
2
LYCAIKOWRPUZTN-UHFFFAOYSA-N
ethylene glycol
Natural products
OCCO
LYCAIKOWRPUZTN-UHFFFAOYSA-N
0.000
title
1
WGCNASOHLSPBMP-UHFFFAOYSA-N
hydroxyacetaldehyde
Natural products
OCC=O
WGCNASOHLSPBMP-UHFFFAOYSA-N
0.000
title
1
150000001768
cations
Chemical class
0.000
abstract
11
239000000376
reactant
Substances
0.000
abstract
5
SIKJAQJRHWYJAI-UHFFFAOYSA-N
Indole
Chemical compound
C1=CC=C2NC=CC2=C1
SIKJAQJRHWYJAI-UHFFFAOYSA-N
0.000
abstract
4
JUJWROOIHBZHMG-UHFFFAOYSA-N
Pyridine
Chemical compound
C1=CC=NC=C1
JUJWROOIHBZHMG-UHFFFAOYSA-N
0.000
abstract
4
KAESVJOAVNADME-UHFFFAOYSA-N
Pyrrole
Chemical compound
C=1C=CNC=1
KAESVJOAVNADME-UHFFFAOYSA-N
0.000
abstract
4
239000000243
solution
Substances
0.000
abstract
4
QTBSBXVTEAMEQO-UHFFFAOYSA-N
Acetic acid
Chemical compound
CC(O)=O
QTBSBXVTEAMEQO-UHFFFAOYSA-N
0.000
abstract
3
239000003054
catalyst
Substances
0.000
abstract
3
229920006395
saturated elastomer
Polymers
0.000
abstract
3
VGGSQFUCUMXWEO-UHFFFAOYSA-N
Ethene
Chemical compound
C=C
VGGSQFUCUMXWEO-UHFFFAOYSA-N
0.000
abstract
2
239000005977
Ethylene
Substances
0.000
abstract
2
239000002253
acid
Substances
0.000
abstract
2
229910052787
antimony
Inorganic materials
0.000
abstract
2
239000007864
aqueous solution
Substances
0.000
abstract
2
229910052785
arsenic
Inorganic materials
0.000
abstract
2
239000006227
byproduct
Substances
0.000
abstract
2
150000001735
carboxylic acids
Chemical class
0.000
abstract
2
238000006243
chemical reaction
Methods
0.000
abstract
2
229910052802
copper
Inorganic materials
0.000
abstract
2
230000000694
effects
Effects
0.000
abstract
2
150000002334
glycols
Chemical group
0.000
abstract
2
PZOUSPYUWWUPPK-UHFFFAOYSA-N
indole
Natural products
CC1=CC=CC2=C1C=CN2
PZOUSPYUWWUPPK-UHFFFAOYSA-N
0.000
abstract
2
RKJUIXBNRJVNHR-UHFFFAOYSA-N
indolenine
Natural products
C1=CC=C2CC=NC2=C1
RKJUIXBNRJVNHR-UHFFFAOYSA-N
0.000
abstract
2
229910052742
iron
Inorganic materials
0.000
abstract
2
239000007791
liquid phase
Substances
0.000
abstract
2
229910052748
manganese
Inorganic materials
0.000
abstract
2
230000003647
oxidation
Effects
0.000
abstract
2
238000007254
oxidation reaction
Methods
0.000
abstract
2
QQONPFPTGQHPMA-UHFFFAOYSA-N
propylene
Natural products
CC=C
QQONPFPTGQHPMA-UHFFFAOYSA-N
0.000
abstract
2
125000004805
propylene group
Chemical group
[H]C([H])([H])C([H])([*:1])C([H])([H])[*:2]
0.000
abstract
2
UMJSCPRVCHMLSP-UHFFFAOYSA-N
pyridine
Natural products
COC1=CC=CN=C1
UMJSCPRVCHMLSP-UHFFFAOYSA-N
0.000
abstract
2
230000001603
reducing effect
Effects
0.000
abstract
2
150000003839
salts
Chemical class
0.000
abstract
2
229910052727
yttrium
Inorganic materials
0.000
abstract
2
229910052725
zinc
Inorganic materials
0.000
abstract
2
QOPGOCFNXRFNQH-UHFFFAOYSA-N
3-acetyloxybut-3-en-2-yl acetate
Chemical compound
CC(=O)OC(C)C(=C)OC(C)=O
QOPGOCFNXRFNQH-UHFFFAOYSA-N
0.000
abstract
1
241001292396
Cirrhitidae
Species
0.000
abstract
1
MYMOFIZGZYHOMD-UHFFFAOYSA-N
Dioxygen
Chemical compound
O=O
MYMOFIZGZYHOMD-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
150000003973
alkyl amines
Chemical class
0.000
abstract
1
150000001448
anilines
Chemical class
0.000
abstract
1
229910052797
bismuth
Inorganic materials
0.000
abstract
1
IAQRGUVFOMOMEM-UHFFFAOYSA-N
butene
Natural products
CC=CC
IAQRGUVFOMOMEM-UHFFFAOYSA-N
0.000
abstract
1
229910052793
cadmium
Inorganic materials
0.000
abstract
1
229910052791
calcium
Inorganic materials
0.000
abstract
1
229910052804
chromium
Inorganic materials
0.000
abstract
1
150000005690
diesters
Chemical class
0.000
abstract
1
229910001882
dioxygen
Inorganic materials
0.000
abstract
1
150000002148
esters
Chemical class
0.000
abstract
1
150000004820
halides
Chemical class
0.000
abstract
1
229910052736
halogen
Inorganic materials
0.000
abstract
1
150000002367
halogens
Chemical class
0.000
abstract
1
150000002475
indoles
Chemical class
0.000
abstract
1
229910052747
lanthanoid
Inorganic materials
0.000
abstract
1
150000002602
lanthanoids
Chemical class
0.000
abstract
1
229910052745
lead
Inorganic materials
0.000
abstract
1
229910052744
lithium
Inorganic materials
0.000
abstract
1
229910052749
magnesium
Inorganic materials
0.000
abstract
1
229910052750
molybdenum
Inorganic materials
0.000
abstract
1
229910052759
nickel
Inorganic materials
0.000
abstract
1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N
pentanoic acid group
Chemical class
C(CCCC)(=O)O
NQPDZGIKBAWPEJ-UHFFFAOYSA-N
0.000
abstract
1
239000000047
product
Substances
0.000
abstract
1
150000003222
pyridines
Chemical class
0.000
abstract
1
150000003233
pyrroles
Chemical class
0.000
abstract
1
229910052706
scandium
Inorganic materials
0.000
abstract
1
229910052708
sodium
Inorganic materials
0.000
abstract
1
IAQRGUVFOMOMEM-ONEGZZNKSA-N
trans-but-2-ene
Chemical compound
C\C=C\C
IAQRGUVFOMOMEM-ONEGZZNKSA-N
0.000
abstract
1
ODHXBMXNKOYIBV-UHFFFAOYSA-N
triphenylamine
Chemical compound
C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1
ODHXBMXNKOYIBV-UHFFFAOYSA-N
0.000
abstract
1
Classifications
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
B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
B01J27/06—Halogens; Compounds thereof
B01J27/08—Halides
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
Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
Y02P20/00—Technologies relating to chemical industry
Y02P20/50—Improvements relating to the production of bulk chemicals
Y02P20/582—Recycling of unreacted starting or intermediate materials
Abstract
1439234 Vicinal glycol esters HALCON INTERNATIONAL Inc 9 Aug 1973 [9 Aug 1972] 37735/73 Heading C2C [Also in Division Bl] Mono- and diesters of vicinal glycols are obtained by the reaction of ethylene and/or propylene with molecular oxygen and at least one C 1-5 monobasic saturated aliphatic hydrocarbyl carboxylic acid, said at least one acid being in excess of that stoichiometrically required, in the liquid phase at between 150 and 250 C. in the presence of a catalyst comprising one or more of (i) Te+Br, (ii) Se+Br and (iii) Se+Cl and at least one basicity control cation in an amount to provide at least 0.05 gram (equivalent (e.g. 0.2 to 3.0) of basicity control cation per gram-atom of total halogen present, said cation having, when in the form of a salt with the halide(s) of the catalyst system, an activity coefficient of at least 0.40 determined at 25 C. in aqueous solution of concentration 0À1 N or saturated, whichever is the more dilute and said cation not having a pH- reducing effect when in the form of a salt(s) with the carboxylic acid reactant. Presence or absence of a pH-reducing effect is determined by comparison of the pH of a 0.1 N or saturated aqueous solution of the carboxylic acid reactant, whichever is the more dilute, with the pH of an otherwise identical solution which also contains 0.1 equivalent of the basicity control cation or which is saturated with respect to the cation salt if this requires less than 0.1 equivalent. The solutions are heated to 50 C. in sealed containers, maintained at 50 C. for 6 hours, cooled to 25 C. and the pH measured. An absence of a pH reducing effect is indicated if the pH of the solution comprising the cation is equal to or greater than the pH of the standard acid solution. More than one of said basicity control cations may be present and specified cations are those formed from alkali metals, alkaline earth metals, the lanthanides, Sc, Y, Fe, Co, Ni, Zn, Bi, Cr, Mn, Mo, Cu, As, Sb, alkyl amines, phenyl amines, alkyl quaternary ammonium salts, pyrrole, pyridine, indole and alkylsubstituted pyrroles, pyridines and indoles. In a preferred embodiment, the reactants are continuously introduced into the oxidation zone and at least a portion of the liquid phase is continuously withdrawn, the withdrawn portion being processed to recover ester products, unconverted reactants and halogenated by-products and the unconverted reactants and at least a major portion of the halogenated by-products being recycled to the oxidation zone. Examples describe the reaction of ethylene or propylene with formic, acetic, propionic and valeric acids using as basicity control cations those formed from Li, Mg, Zn, Ca, Mn, Ni, Ce, As, Sb, Na, Fe, Cr, Mo, Sc, Y, Bi, Cu, (C 2 H 5 ) 3 N, pyridine, pyrrole, indole, triphenylamine and (C 2 H 5 ) 4 NOH. Control runs presented for comparison include the preparation of 2,3-diacetoxybutene from butene-2 and acetic acid, the use of Te + Cl as the catalyst system and the use of cations of Ag, Hg, Cd or Pb and of H 2 SO 4 , in place of the basicity control cations.
GB3773573A
1972-08-09
1973-08-09
Vicinal glycol ester preparation process
Expired
GB1439234A
(en)
Applications Claiming Priority (1)
Application Number
Priority Date
Filing Date
Title
US278903A
US3907874A
(en)
1972-08-09
1972-08-09
Vicinal glycol ester preparation process
Publications (1)
Publication Number
Publication Date
GB1439234A
true
GB1439234A
(en)
1976-06-16
Family
ID=23066884
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB3773573A
Expired
GB1439234A
(en)
1972-08-09
1973-08-09
Vicinal glycol ester preparation process
Country Status (13)
Country
Link
US
(1)
US3907874A
(en)
JP
(1)
JPS5745213B2
(en)
AU
(1)
AU472966B2
(en)
BE
(1)
BE803189A
(en)
CA
(1)
CA1026370A
(en)
DE
(1)
DE2340395C3
(en)
ES
(1)
ES417707A1
(en)
FR
(1)
FR2195616B1
(en)
GB
(1)
GB1439234A
(en)
IN
(1)
IN139697B
(en)
IT
(1)
IT990208B
(en)
NL
(1)
NL165452C
(en)
SE
(1)
SE405474B
(en)
Families Citing this family (13)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US4045477A
(en)
*
1975-07-17
1977-08-30
Chem Systems Inc.
Acetoxylation process
US4073876A
(en)
*
1976-07-01
1978-02-14
Halcon International, Inc.
Preparation of glycol esters
JPS5449043A
(en)
*
1977-09-27
1979-04-18
Tokyo Electric Co Ltd
Electronic cash register
US4153806A
(en)
*
1977-10-11
1979-05-08
Halcon Research And Development Corp.
Recovery of vicinal glycol esters by plural stage distillation
US4228301A
(en)
*
1977-10-21
1980-10-14
Japan Synthetic Rubber Co., Ltd.
Process for the preparation of diacetoxybutene
JPS5556237A
(en)
*
1978-09-27
1980-04-24
Tokyo Electric Co Ltd
Date change system of label printer
US4245114A
(en)
*
1978-12-19
1981-01-13
Halcon Research And Development Corporation
Glycol ester preparation
US4237312A
(en)
*
1979-04-02
1980-12-02
Phillips Petroleum Company
Oxidation process including recovery and recycle of catalyst
US4224301A
(en)
*
1979-08-20
1980-09-23
Atlantic Richfield Company
Removal of tellurium from glycol ester solutions
US4256912A
(en)
*
1979-10-09
1981-03-17
Atlantic Richfield Company
Removal of soluble tellurium or compounds thereof from a crude glycol ester solution
US4271090A
(en)
*
1979-10-29
1981-06-02
Halcon Research And Development Corp.
Novel 2-bromoethyl tellurium bromides
US4528396A
(en)
*
1982-09-24
1985-07-09
Texaco Inc.
Dicyclopentadiene derived ester compounds
JPS5972808U
(en)
*
1982-11-05
1984-05-17
株式会社明電舎
Disconnect section of closed switchboard
Family Cites Families (3)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US3479395A
(en)
*
1966-05-02
1969-11-18
Celanese Corp
Oxidation of olefins with tellurium compounds
US3689535A
(en)
*
1968-09-26
1972-09-05
John Kollar
Process for preparing ethylene glycol esters
US3668239A
(en)
*
1970-04-23
1972-06-06
Halcon International Inc
Process for preparing glycol esters from olefinically unsaturated compounds
1972
1972-08-09
US
US278903A
patent/US3907874A/en
not_active
Expired – Lifetime
1973
1973-05-26
IN
IN1239/CAL/73A
patent/IN139697B/en
unknown
1973-07-24
NL
NL7310271.A
patent/NL165452C/en
not_active
IP Right Cessation
1973-08-02
AU
AU58838/73A
patent/AU472966B2/en
not_active
Expired
1973-08-03
BE
BE134210A
patent/BE803189A/en
unknown
1973-08-08
CA
CA178,315A
patent/CA1026370A/en
not_active
Expired
1973-08-08
FR
FR7328953A
patent/FR2195616B1/fr
not_active
Expired
1973-08-09
DE
DE2340395A
patent/DE2340395C3/en
not_active
Expired
1973-08-09
JP
JP48089620A
patent/JPS5745213B2/ja
not_active
Expired
1973-08-09
GB
GB3773573A
patent/GB1439234A/en
not_active
Expired
1973-08-09
SE
SE7310908A
patent/SE405474B/en
unknown
1973-08-09
ES
ES417707A
patent/ES417707A1/en
not_active
Expired
1973-08-09
IT
IT51940/73A
patent/IT990208B/en
active
Also Published As
Publication number
Publication date
CA1026370A
(en)
1978-02-14
BE803189A
(en)
1974-02-04
US3907874A
(en)
1975-09-23
DE2340395C3
(en)
1982-05-27
AU472966B2
(en)
1976-06-10
IN139697B
(en)
1976-07-17
NL7310271A
(en)
1974-02-12
DE2340395A1
(en)
1974-02-21
NL165452C
(en)
1981-04-15
NL165452B
(en)
1980-11-17
AU5883873A
(en)
1975-02-06
ES417707A1
(en)
1976-06-01
JPS4945012A
(en)
1974-04-27
FR2195616B1
(en)
1979-04-13
JPS5745213B2
(en)
1982-09-27
IT990208B
(en)
1975-06-20
DE2340395B2
(en)
1980-09-04
FR2195616A1
(en)
1974-03-08
SE405474B
(en)
1978-12-11
Similar Documents
Publication
Publication Date
Title
GB1439234A
(en)
1976-06-16
Vicinal glycol ester preparation process
EP0065817B1
(en)
1985-07-24
Process for producing carboxylic acids
US4830716A
(en)
1989-05-16
Preparation of pharmaceutical grade amino acid chelates
US3920756A
(en)
1975-11-18
Method for preparing catechol and hydroquinone
GB1208550A
(en)
1970-10-14
Process for producing molybdenum carboxylates
GB1272820A
(en)
1972-05-03
Production of ethylene glycol esters and compounds derived thereform
GB1300718A
(en)
1972-12-20
2-THIOMETHYL- AND 2-THIOMETHYLENE-Delta<3>-CEPHALOSPORIN COMPOUNDS AND SULFOXIDE THEREOF
GB1473447A
(en)
1977-05-11
Production of salts of lower fatty acids and halogenated fatty acids
EP0121366B1
(en)
1987-11-04
Process for the preparation of n-formylaspartic anhydride
ES8105692A1
(en)
1981-06-01
Process for preparing 2-nitro-5-(substituted-phenoxy) benzoic acids and salts thereof.
GB1381058A
(en)
1975-01-22
Process for the manufacture of alkyl esters of carboxylic acids
DE3360106D1
(en)
1985-05-15
Process for the production of oil-soluble metal salts
ES353474A1
(en)
1969-09-16
Process for the manufacture of linear polyesters using metal germanates and metal glycol germanates as the catalyst
US4296243A
(en)
1981-10-20
Process for producing sorbic acid or its derivatives
SU581864A3
(en)
1977-11-25
Mehtod of preparing imidazole derivatives or salts thereof
GB1423495A
(en)
1976-02-04
Oligocarboxyalkane-phosphonic acids and process for makiing them
DE3564425D1
(en)
1988-09-22
Process for preparing carbonyl compounds
EP0098689B1
(en)
1986-12-17
Process for the production of monocarboxylic acid anhydrides
SU441702A1
(en)
1974-08-30
Method for producing ethylene glycol esters
GB1416773A
(en)
1975-12-10
Process for the preparation of certain thionphosphoric acid esters
GB1456446A
(en)
1976-11-24
Process for the production of dichlorobenzoic acids
EP0359098B1
(en)
1993-03-17
Method of manufacturing alkali metal salt of 2,3,6,7-naphthalenetetracarboxylic acid
ES8606238A1
(en)
1986-04-16
Process for the preparation of dibasic lead (II) salts of fatty acids by the fusion process.
JPS61112073A
(en)
1986-05-30
Production of 1-(2-tetrahydrofuryl)-5-fluorouracil
DE3273805D1
(en)
1986-11-20
Improved bacterial growth medium and method of growing bacteria
Legal Events
Date
Code
Title
Description
1976-10-27
PS
Patent sealed [section 19, patents act 1949]
1980-12-03
732
Registration of transactions, instruments or events in the register (sect. 32/1977)
1982-09-15
732
Registration of transactions, instruments or events in the register (sect. 32/1977)
1984-04-04
PCNP
Patent ceased through non-payment of renewal fee
