GB2050372A - Process for the alkoxylation of alcohols - Google Patents
Process for the alkoxylation of alcohols Download PDFInfo
- Publication number
- GB2050372A GB2050372A GB8015219A GB8015219A GB2050372A GB 2050372 A GB2050372 A GB 2050372A GB 8015219 A GB8015219 A GB 8015219A GB 8015219 A GB8015219 A GB 8015219A GB 2050372 A GB2050372 A GB 2050372A
- Authority
- GB
- United Kingdom
- Prior art keywords
- inclusive
- process according
- catalyst
- alcohol
- molybdenum
- Prior art date
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- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 150000001298 alcohols Chemical class 0.000 title abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000011733 molybdenum Substances 0.000 claims abstract description 17
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 16
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 15
- 239000010937 tungsten Substances 0.000 claims abstract description 14
- -1 alkylene glycol mono alkyl ethers Chemical class 0.000 claims abstract description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 239000011964 heteropoly acid Substances 0.000 claims abstract description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 229960004592 isopropanol Drugs 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical group O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 2
- 229940044613 1-propanol Drugs 0.000 claims 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 3
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 3
- 238000007046 ethoxylation reaction Methods 0.000 description 3
- 229910052684 Cerium Inorganic materials 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- QVYYOKWPCQYKEY-UHFFFAOYSA-N [Fe].[Co] Chemical compound [Fe].[Co] QVYYOKWPCQYKEY-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- VVRQVWSVLMGPRN-UHFFFAOYSA-N oxotungsten Chemical class [W]=O VVRQVWSVLMGPRN-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
A process for the production of alkylene glycol mono alkyl ethers by the alkoxylation of alcohols in the presence of a molybdenum or tungsten heteropoly acid catalyst. The process is particularly useful in the alkoxylation of alcohols to give high ratios of mono- to di-alkoxylated products.
Description
SPECIFICATION
Process for the alkoxylation of alcohols
This invention relates to a process for the production of alkylene glycol ethers by the alkoxylation of alcohols and more particularly to the use of the heteropoly acids of molybdenum and tungsten as catalysts in the alkoxylation of alcohols.
In the commercial production of alkylene glycol ethers by the alkoxylation of the lower alcohols, the product distribution, or ratio of mono-, di-, tri- and higher alkoxylates, is of considerable importance. The mono-alkoxylates are, in the main the most important commercial products but their production is always accompanied by the production of some of the di-, tri- and higher alkoxylates.
From studies using the ethoxylation of ethanol as a model it appears that as a general rule the slower the reaction the higher the proportion of the mono-ethoxylate in the final product. For example, the ethoxylation of ethanol at 160"C using an ethanol to ethylene oxide mole ratio of 6:1 and no catalyst gives a product in which the mole ratio of mono- to di-ethoxylate is of the order of 18. However, while this ratio represents a good mono- to di-ethoxylate product distribution the uncatalysed reaction is unacceptably slow having a half-life of the order of 100 minutes. On the other hand when ethanol is ethoxylated under the same conditions using potassium hydroxide as catalyst the reaction proceeds at an acceptable rate with a half-life of the order of 8 minutes but the ratio of mono- to di-ethoxylate is much less favourable being of the order of 6.
It follows, that an alkoxylation process which combined the features of a relatively fast reaction rate and a product with a relatively high mono- to di-alkoxylate ratio would have considerable merit. It has now been found that the oxo acids of certain transition elements may be used as catalysts to give an alkoxylation process which combines the abovementioned desired features.
Accordingly, the invention provides a process for the production of alkylene glycol mono-alkyl ethers which process comprises the reaction of a C2 to C4 alkylene oxide with a C1 to C5 alcohol in the presence of a soluble catalyst comprising a heteropoly acid of molybdenum or tungsten.
Throughout the specification and claims the term "heteropoly acid of molybdenum or tungsten" refers to those compounds which comprise linked MoO6 and/or WO6 octahedra surrounding one or two central (hetero) atoms. The heteropoly acids of tungsten and molybdenum are discussed in the the standard texts "Advanced Inorganic Chemistry. A Comprehensive Text", A F Cotton and G Wilkinson, Second Revised and augmented Edition, Interscience New York 1966, pp 938-946, "Comprehensive Inorganic Chemistry", Editors
J. C. Bailar, H. J. Emelius, R. Nyholm and A. F. Trotman-Dickenson, First Edition, Pergamon Press 1973,
Volume 3 pp 739-741 and pp 767-768 and more comprehensively in Volume 4 pp 656-672 of the latter reference.
Considered in terms of the ratio of the number of central hetero atoms to the number of peripheral metal atoms the heteropoly acids of molybdenum and tungsten fall into four main groups, the 1:6, 1:9, 1:12 and 2.18 groups, and three minor groups, the 1:10,1:11 and 2:17 groups. The four main groups may be represented by the following formulae in which n represents the valency of the hetero atom, X represents the hetero atom and M represents a molybdenum or tungsten atom
1:6 series
1:9 series 1:12 series 2:18 series.
The hetero atom X may be chosen from a wide range of elements including the cations of phosphorous, silicon, boron, copper, zinc, iron, aluminium, germanium, vanadium, chromium, gallium, tellurium, manganese, beryllium, cerium, iodine, cobalt, tin, arsenic, antimony, bismuth, selenium, titanium, nickel and cerium. Preferred cations include those of phosphorus and silicon.
While M is usually chosen from either molybdenum or tungsten certain of the heteropoly acids of molybdenum and tungsten contain both molybdenum and tungsten and in others one or more but not all of the molybedenum or tungsten atoms may be replaced by one or more other metal atoms such as, for example, vanadium, manganese, iron cobalt, nickel, copper, zinc, and titanium.
Preferred heteropoly acids for use in the process of the invention include phosphomolybdic acid (H3PMo,2040 xH20) The heteropoly acids of molybdenum and tungsten may conveniently be prepared by the acidification of molybdate and tungstate solutions containing other oxo anions. For example, phosphopoly acids of molybdenum or tungsten may be prepared by the dissolution of molybdenum or tungsten oxides in phosphoric acid. In the process of the invention the heteropoly acids of molybdenum and tungsten may be used as catalysts in the form of purified compounds or in crude form, for example, without isolation from the reaction mixture in which they were prepared.
The amount of the heteropoly acid of molybdenum or tungsten used as catalyst in the process of the invention will depend to a large extent on the nature of the catalyst used and the alcohol and alkylene oxide which are being reacted. However, in general a catalyst level in the range of from 10 to 5,000 ppm, based on the weight of the alcohol reactant, is suitable provided that the catalyst is soluble in the alcohol reactant at the level of use. A range of from 100 to 1000 ppm is preferred.
Suitable alcohols for use in the process of the inventon include the primary and secondary C1 to C6 alcohols such as methanol, ethanol, propanol, isopropanol, butanol, 1-methylpropanol and 2methylpropanol. Suitable alkylene oxides include ethylene oxide, propylene oxide and butylene oxide.
The temperature at which the process of the invention is carried out will depend on a number of factors including the heating and cooling facilities available on the reaction vessel and the pressure at which the reaction vessel may be operated. However, in general, a temperature in the range of from 50 to 250"C is satisfactory and a temperature in the range from 80 to 200"C is preferred.
The process of the invention may be used to particular advantage in the production of ethylene glycol mono-alkyl ethers by the ethoxylation of ethanol, iso-propanol and n-butanol.
The invention is now illustrated, but not limited, by the following Examples.
Examples lto4 In order to demonstrate the effectiveness of the process of the invention ethanol was ethoxylated in an autoclave at a temperature of 1 60 C according to the following general procedure.
Ethanol containing the dissolved catalyst was charged into an evacuated autoclave. The autoclave and contents were heated with stirring to a temperature of 1 600C. Ethylene oxide (EO) was then introduced into the autoclave and the contents were heated with stirring until the reaction was complete.
The progress of the reaction was monitored by sampling the reaction mixture at regular intervals. The samples were quenched and analysed by vapour phase chromatography over 10% Carbowax 20M/
Chromosorb W using added butanol as an internal standard (Chromosorb is a Registered Trade Mark). The data from the analyses were used to calculate the reaction half-life (t1/2) and the mole ratio of the products ethylene glycol mono ethyl ether (EGE) and diethylene glycol mono ethyl ether (DEGE).
The results are recorded in Table 1 in which Examples 1 and 2 are comparative Examples not of the invention and PMA refers to the catalyst phosphomolybdic acid (H3PMoa2040.24H2O).
TABLE 1
Ex- Catalyst
ample Mole Ratio Level t1/2 Mole Ratio
No EtOH:EO Catalyst (w/w (min) EGE:DEGE
w.r.t. EtOH)
1 6:1 None - 104 18.5:1
2 6:1 KOH 100 ppm 8.5 6.5:1
3 6:1 PMA 1750 ppm < < 5 10.1:1 4 6:1 PMA 525 ppm 5 10.8:1
Claims (12)
1. A process for the production of an alkylene glycol mono-alkyl ether which process comprises reacting
C2 to C4 alkylene oxide with a C1 to C6 alcohol in the presence of a soluble catalyst comprising a heteropoly acid of molybdenum or tungsten as hereinbefore defined.
2. A process according to claim 1 wherein in said heteropoly acid catalyst the hetero atom is chosen from phosphorus and silicon.
3. A process according to claim 1 or claim 2 wherein said catalyst is a heteropoly acid of molybdenum and the heteroatom is phosphorus.
4. A process according to any one of claims 1 to 3 inclusive wherein said catalyst is phosphomolybdic acid.
5. A process according to any one of claims 1 to 4 inclusive wherein said catalyst is used at a level in the range of from 10 to 5,000 parts per million based on the weight of the alcohol.
6. A process according to any one of claims 1 to 5 inclusive wherein said catalyst is used at a level in the range of from 100 to 1,000 parts per million based on the weight of the alcohol.
7. A process according to any one of claims 1 to 6 inclusive wherein said alcohol is chosen from methanol, ethanol, 1 -propanol, isopropanol, 1 -butanol, 1 -methylpropanol and 2-methylpropanol.
8. A process according to any one of claims 1 to 7 inclusive wherein said alcohol is chosen from ethanol, 2-propanol and 1-butanol.
9. A process according to any one of claims 1 to 7 inclusive wherein said alkylene oxide is ethylene oxide and said alcohol is ethanol.
10. A process according to any one of claims 1 to 9 inclusive wherein the reaction is carried out at a temperature in the range of from 50 to 2500C.
11. A process substantially as hereinbefore described with reference to Example 3 or Example 4.
12. An alkylene glycol mono-alkyl ether prepared according to the process of any one of claims 1 to 11 inclusive.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU879579 | 1979-05-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2050372A true GB2050372A (en) | 1981-01-07 |
| GB2050372B GB2050372B (en) | 1983-03-02 |
Family
ID=3699513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8015219A Expired GB2050372B (en) | 1979-05-14 | 1980-05-08 | Process for the alkoxylation of alcohols |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU533952B2 (en) |
| GB (1) | GB2050372B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5874714A (en) * | 1981-10-27 | 1983-05-06 | Mitsui Petrochem Ind Ltd | Production of polyepoxide/aliphatic alcohol adduct |
| EP0419077A3 (en) * | 1989-09-20 | 1992-05-27 | Texaco Chemical Company | Synthesis of low molecular weight ethylene propylene glycol ethers via olefin addition to the corresponding glycol |
| US5349110A (en) * | 1990-08-20 | 1994-09-20 | Texaco Chemical Company | Synthesis of low molecular weight glycol ethers from oxiranes plus olefins |
| WO2005087696A1 (en) * | 2004-03-11 | 2005-09-22 | Basf Aktiengesellschaft | Method for producing monoalkylene glycol monoether |
| CN103012077A (en) * | 2011-09-28 | 2013-04-03 | 中国石油化工股份有限公司 | Method for preparing propylene glycol monomethyl ether by catalyzing alcoholysis of propylene epoxide |
-
1979
- 1979-05-14 AU AU58504/80A patent/AU533952B2/en not_active Ceased
-
1980
- 1980-05-08 GB GB8015219A patent/GB2050372B/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5874714A (en) * | 1981-10-27 | 1983-05-06 | Mitsui Petrochem Ind Ltd | Production of polyepoxide/aliphatic alcohol adduct |
| EP0419077A3 (en) * | 1989-09-20 | 1992-05-27 | Texaco Chemical Company | Synthesis of low molecular weight ethylene propylene glycol ethers via olefin addition to the corresponding glycol |
| US5349110A (en) * | 1990-08-20 | 1994-09-20 | Texaco Chemical Company | Synthesis of low molecular weight glycol ethers from oxiranes plus olefins |
| WO2005087696A1 (en) * | 2004-03-11 | 2005-09-22 | Basf Aktiengesellschaft | Method for producing monoalkylene glycol monoether |
| CN103012077A (en) * | 2011-09-28 | 2013-04-03 | 中国石油化工股份有限公司 | Method for preparing propylene glycol monomethyl ether by catalyzing alcoholysis of propylene epoxide |
| CN103012077B (en) * | 2011-09-28 | 2015-02-25 | 中国石油化工股份有限公司 | Method for preparing propylene glycol monomethyl ether by catalyzing alcoholysis of propylene epoxide |
Also Published As
| Publication number | Publication date |
|---|---|
| AU533952B2 (en) | 1983-12-22 |
| GB2050372B (en) | 1983-03-02 |
| AU5850480A (en) | 1980-11-20 |
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| Date | Code | Title | Description |
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| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940508 |