(Methylcyclohexyl)toluene isomer mixtures,their production and their use in the manufacture of plasticizers

Patent metadata

Field	Value
Publication number	US-9580572-B2
Application number	US-201414201224-A
Country	US
Kind code	B2
Filing date	Mar 7, 2014
Priority date	Mar 14, 2013
Publication date	Feb 28, 2017
Grant date	Feb 28, 2017

Abstract

A composition is described comprising a mixture of (methylcyclohexyl)toluene isomers having the following formula:

wherein the mixture comprises at least 50 wt % in total of the 3,3, 3,4 4,3 and 4,4-isomers of (methylcyclohexyl)toluene.

First claim

The invention claimed is:

1. A composition comprising a mixture of (methylcyclohexyl)toluene isomers represented by the following formula:

wherein said mixture comprises at least 50 wt % in total of the 3,3, 3,4, 4,3 and 4,4-isomers of (methylcyclohexyl)toluene, wherein the mixture comprises less than 10 wt % of y-(x-ethylcyclopentenyl)toluene, x=2, 3, 4, y=2, 3, 4, and wherein said mixture comprises at least 10 wt % of 3,3-(methylcyclohexyl)toluene, at least 10 wt % of 3,4-(methylcyclohexyl)toluene, at least 10 wt % of 4,3-(methylcyclohexyl)toluene and at least 10 wt % of 4,4-(methylcyclohexyl)toluene.

2. The composition of claim 1 , wherein said mixture comprises at least 60 wt % in total of the 3,3, 3,4, 4,3 and 4,4-isomers of (methylcyclohexyl)toluene.

3. The composition of claim 1 , wherein the total amount of isomers with a methyl group at the 2-position on either the phenyl or the cyclohexyl ring is less than 40 wt % of said mixture.

4. The composition of claim 1 , wherein the total amount of isomers with a methyl group at the 2-position on either the phenyl or the cyclohexyl ring is less than 30 wt % of said mixture.

5. The composition of claim 1 , wherein the total amount of (1-methylcyclohexyl)toluene, (ethylcyclopentyl)toluenes and (diethylcyclopentyl)toluenes in said mixture is less than 5 wt %.

6. The composition of claim 1 , wherein the composition is produced by a process comprising contacting a feed comprising toluene with hydrogen in the presence of a hydroalkylation catalyst comprising an MCM-22 family molecular sieve and a hydrogenation component.

7. The composition of claim 1 , wherein the composition is produced by a process comprising:
(a) contacting a feed comprising toluene with hydrogen in the presence of a hydroalkylation catalyst under conditions effective to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluenes; wherein toluene feed is removed from the hydroalkylation reaction product of step a) and recycled back to the hydroalkylation of step a), and wherein fully saturated single ring by-products in the hydroalkylation reaction product of step a) are dehydrogenated to produce recyclable feed that is recycled back to the hydroalkylation of step a).

8. The composition of claim 1 , wherein the composition is produced by a process comprising:
(a) contacting a feed comprising toluene with hydrogen in the presence of a hydroalkylation catalyst under conditions effective to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluenes; wherein toluene feed is removed from the hydroalkylation reaction product of step a) and recycled back to the hydroalkylation of step a), and wherein methylcyclohexane and dimethylcyclohexane in the hydroalkylation reaction product of step a) are dehydrogenated to produce recyclable feed that is recycled back to the hydroalkylation of step a).

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Dakka Jihad M
• Decaul Lorenzo C
• Tang Wei

Classifications

• C07C5/367

  Formation of an aromatic six-membered ring from an existing six-membered ring, e.g. dehydrogenation of ethylcyclohexane to ethylbenzene · CPC title

• C08K5/12 Primary

  of cyclic polycarboxylic acids · CPC title

• C07C2523/62

  with gallium, indium, thallium, germanium, tin or lead · CPC title

• C07C2521/04

  Alumina · CPC title

• C07C2/74

  by addition with simultaneous hydrogenation · CPC title