US 4,071,568 AGranted

Process for producing glycol monoether

AssigneeMitsubishi Chemical Industries Limited

InventorsTakeru Onoda, Shimpei Tomita

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Abstract

Glycol monoethers are produced in high yields by reacting an acetal with carbon monoxide and hydrogen in the presence of a catalyst comprising a cobalt compound and a trivalent organic phosphorus compound or a bidentate chelate ligand containing nitrogen or oxygen. An aldehyde or a compound capable or releasing an aldehyde under reaction conditions and an alcohol can be used instead of the acetal.

Claims19

Dependent claims

A process for producing a glycol monoether which comprises reacting

A. at least one member selected from the group consisting of
i. an acetal having the general formula:
R.sup.1 OCHR.sup.3 OR.sup.2
wherein R.sup.1 and R.sup.2 are the same or different and represent an aliphatic or alicyclic radical of 1 to 8 carbon atoms, or aromatic hydrocarbon radicals of 6 to 7 carbon atoms, R.sup.3 represents hydrogen, an aliphatic or alicyclic radical of 1 to 8 carbon atoms or aromatic hydrocarbons radicals of 6 to 7 carbon atoms and the hydrocarbon radicals may have a substituent inert to the reaction,
ii.
a. an aldehyde having the general formula:
R.sup.3 CHO
wherein R.sup.3 is the same as defined above and
b. an alcohol having the general formula:
R.sup.4 OH
wherein R.sup.4 is the same as R.sup.1 or R.sup.2, and
iii.
c. paraformaldehyde or trioxane and
d. an alcohol as defined above (b), with
B. carbon monoxide and
C. hydrogen
wherein the molar ratio of hydrogen/carbon monoxide is 0.1 to 10, in the presence of
D. a catalyst comprising
1. a cobalt compound selected from the group consisting of cobalt carbonyl, cobalt oxide, organic acid salts of cobalt and inorganic acid salts of cobalt, and
2. at least one compound selected from the group consisting of
e. trivalent organic phosphorus compounds selected from the group consisting of tertiary phosphines having an alkyl group of 1 to 8 carbon atoms, an aryl group of 6 to 7 carbon atoms or a cyclohexyl group, phosphines having two phosphorus atoms and tertiary phosphites corresponding to the above-mentioned phosphines,
f. nitrogen-containing bidentate chelate ligand selected from the group consisting of ##STR3## and dinitriles having the general formula:
NC(CH.sub.2).sub.n CN, wherein n is an integer of 1 to 10, and
g. oxygen-containing bidentate chelate ligand selected from the group consisting of CH.sub.3 COCH.sub.2 COCH.sub.3, CH.sub.3 CH.sub.2 OCOCH.sub.2 COOCH.sub.2 CH.sub.3 and ##STR4## at a temperature of 50.degree. to 300.degree. C and under the pressure of 10 to 1,000 kg/cm.sup.2 gauge.

21 more elements

Dependencies are inferred from the claim text.

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Abstract

A process for producing a glycol monoether which comprises reacting

A. at least one member selected from the group consisting of
i. an acetal having the general formula:
R.sup.1 OCHR.sup.3 OR.sup.2
wherein R.sup.1 and R.sup.2 are the same or different and represent an aliphatic or alicyclic radical of 1 to 8 carbon atoms, or aromatic hydrocarbon radicals of 6 to 7 carbon atoms, R.sup.3 represents hydrogen, an aliphatic or alicyclic radical of 1 to 8 carbon atoms or aromatic hydrocarbons radicals of 6 to 7 carbon atoms and the hydrocarbon radicals may have a substituent inert to the reaction,
ii.
a. an aldehyde having the general formula:
R.sup.3 CHO
wherein R.sup.3 is the same as defined above and
b. an alcohol having the general formula:
R.sup.4 OH
wherein R.sup.4 is the same as R.sup.1 or R.sup.2, and
iii.
c. paraformaldehyde or trioxane and
d. an alcohol as defined above (b), with
B. carbon monoxide and
C. hydrogen
wherein the molar ratio of hydrogen/carbon monoxide is 0.1 to 10, in the presence of
D. a catalyst comprising
1. a cobalt compound selected from the group consisting of cobalt carbonyl, cobalt oxide, organic acid salts of cobalt and inorganic acid salts of cobalt, and
2. at least one compound selected from the group consisting of
e. trivalent organic phosphorus compounds selected from the group consisting of tertiary phosphines having an alkyl group of 1 to 8 carbon atoms, an aryl group of 6 to 7 carbon atoms or a cyclohexyl group, phosphines having two phosphorus atoms and tertiary phosphites corresponding to the above-mentioned phosphines,
f. nitrogen-containing bidentate chelate ligand selected from the group consisting of ##STR3## and dinitriles having the general formula:
NC(CH.sub.2).sub.n CN, wherein n is an integer of 1 to 10, and
g. oxygen-containing bidentate chelate ligand selected from the group consisting of CH.sub.3 COCH.sub.2 COCH.sub.3, CH.sub.3 CH.sub.2 OCOCH.sub.2 COOCH.sub.2 CH.sub.3 and ##STR4## at a temperature of 50.degree. to 300.degree. C and under the pressure of 10 to 1,000 kg/cm.sup.2 gauge.

21 more elements