Production of cyclic acetals or ketals using liquid-phase acid catalysts

Patent metadata

Field	Value
Publication number	US-9394271-B2
Application number	US-201514605067-A
Country	US
Kind code	B2
Filing date	Jan 26, 2015
Priority date	Jun 24, 2011
Publication date	Jul 19, 2016
Grant date	Jul 19, 2016

Abstract

A liquid composition containing at least 2 mole % of water, at least 50 mole % of polyhydroxyl compounds, at least 3 mole % of cyclic compounds, and at least 0.01 mole % of a homogeneous acid catalyst. The mole percentages are based on the moles of all liquids in the composition. The liquid composition optionally contains up to 20 mole % of carbonyl compounds, based on the number of moles of the cyclic compounds. The cumulative amount of any other liquid ingredient in the liquid composition does not exceed 10 mole %. The cyclic compounds include cyclic acetals, cyclic ketals, or a combination thereof. The liquid composition is derived from a process for making cyclic compounds by feeding aldehyde or ketone compounds and polyhydroxyl compounds to a reaction vessel at a molar ratio of polyhydroxyl compounds to aldehyde or ketone compounds of at least 3:1, reacting these compounds in the presence of a homogeneous acid catalyst to generate a liquid phase homogeneous reaction mixture containing the acid catalyst without separating water from the reaction mixture as it is being formed in the reaction mixture, withdrawing the liquid phase homogeneous reaction mixture from the reaction vessel as a liquid product stream, and feeding the liquid reaction product stream to a distillation column to separate cyclic acetal or ketal compounds from unreacted polyhydroxyl compounds.

First claim

What we claim is:

1. A liquid composition comprising:
a) at least 2 mole % of water;
b) at least 50 mole % of polyhydroxyl compounds;
c) at least 3 mole % of cyclic compounds; and
d) at least 0.01 mole % of a homogeneous acid catalyst;
wherein the mole percentages are based on the moles of all liquids in the composition,
wherein the liquid composition optionally contains carbonyl compounds which, if present, do not exceed 20% of the number of moles of the cyclic compounds,
wherein the cumulative amount of any other liquid ingredient in the liquid composition does not exceed 10 mole %, and
wherein the cyclic compounds comprise cyclic acetals, cyclic ketals, or a combination thereof.

2. The liquid composition of claim 1 , which comprises:
a) 3 to 25 mole % of water;
b) 50 to 90 mole % of polyhydroxyl compounds;
c) 3 to 25 mole % of cyclic compounds; and
d) 0.02 to 5 mole % of a homogeneous acid catalyst.

3. The liquid composition of claim 2 , which comprises:
a) 8 to 25 mole % of water;
b) 50 to 85 mole % of polyhydroxyl compounds; and
c) 7 to 25 mole % of cyclic compounds.

Assignees

• Eastman Chem Co

Inventors

• Terrill Daniel Latham
• Mcmurray Brian David
• Billodeaux Damon Ray
• Little James Lon
• Howard Adam Scott

Classifications

• C07D317/12 Primary

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms · CPC title