Production of cyclic acetals or ketals using solid acid catalysts

Patent metadata

Field	Value
Publication number	US-9440944-B2
Application number	US-201414337544-A
Country	US
Kind code	B2
Filing date	Jul 22, 2014
Priority date	Jun 24, 2011
Publication date	Sep 13, 2016
Grant date	Sep 13, 2016

Abstract

A process for making a cyclic compounds such as cyclic acetal or cyclic ketones by feeding aldehyde or ketone compounds and polyhydroxyl compounds to a reaction zone 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 solid acid such as an acidic ion exchange resin, to generate a liquid reaction mixture without separating water from the reaction mixture as it is being formed in the reaction mixture, withdrawing the liquid reaction mixture from the reaction zone as a liquid product stream, and feeding the liquid reaction product stream to a distillation column to separate cyclic acetal compounds from unreacted polyhydroxyl compounds, and optionally recycling back the unreacted polyhydroxyl compounds to the reaction zone. The process produces cyclic acetal compounds in yields of at least 90% with long catalyst life. The process is also suitable to make cyclic ketals from ketone compounds.

First claim

What we claim is:

1. A liquid composition comprising:
a) at least 2 mole % of water;
b) at least 75 mole % of polyhydroxyl compounds; and
c) at least 3 mole % of cyclic compounds;
wherein the mole percentages of water, polyhydroxyl compounds, and cyclic compounds 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 cyclic compounds, and
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) at least 3 mole % of water;
b) at least 80 mole % of polyhydroxyl compounds; and
c) at least 6 mole % of cyclic compounds.

3. The liquid composition of claim 2 , which comprises:
a) at least 9 mole % of water; and
c) at least 9 mole % of cyclic compounds.

4. The liquid composition of claim 1 , which comprises:
a) at least 12 mole % of water;
b) at least 75 mole % of polyhydroxyl compounds mole %; and
c) at least 12 mole % of cyclic compounds.

5. The liquid composition of claim 1 , wherein the cyclic compounds comprise cyclic acetals.

6. The liquid composition of claim 1 , wherein the amount of any other liquid ingredient in the liquid composition does not exceed 8 mole %.

7. The liquid composition of claim 6 , wherein the amount of any other liquid ingredient in the liquid composition does not exceed 5 mole %.

8. An isolated composition comprising the liquid composition according to any one of claims 1 - 7 .

Assignees

• Eastman Chem Co

Inventors

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

Classifications

• C07D323/00 Primary

  Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms · CPC title

• C07D321/08

  1,4-Dioxepines; Hydrogenated 1,4-dioxepines · CPC title

• C07D319/12

  not condensed with other rings · CPC title

• C07D317/12

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

• C07D321/06

  1,3-Dioxepines; Hydrogenated 1,3-dioxepines · CPC title