Process for preparing a para-branched alkyl-substituted hydroxyaromatic compound

Patent metadata

Field	Value
Publication number	US-9803154-B2
Application number	US-201414529252-A
Country	US
Kind code	B2
Filing date	Oct 31, 2014
Priority date	Oct 31, 2013
Publication date	Oct 31, 2017
Grant date	Oct 31, 2017

Abstract

Disclosed herein is a process for preparing an isomeric mixture comprising a major amount of a para-branched mono-alkyl-substituted hydroxyaromatic compound. The process involves the steps of: (a) providing an isomeric mixture comprising a major amount of a para-di(alkyl-substituted)aromatic compound; wherein a first alkyl substituent is a C 3 to C 8 alkyl moiety and a second alkyl substituent is a C 4+n to C 8+n branched alkyl moiety, wherein n is 0 to 42 and further wherein the second alkyl substituent is at least one carbon atom greater than the first alkyl substituent; (b) subjecting the isomeric mixture comprising a major amount of a para-di(alkyl-substituted)aromatic compound to oxidation conditions in the presence of an oxygen-containing source, thereby converting the first alkyl substituent which is a C 3 to C 8 alkyl moiety to a hydroperoxide-containing substituted moiety to produce an isomeric mixture comprising a major amount of a para-branched alkyl-substituted, hydroperoxide-containing substituted aromatic compound; and (c) converting the hydroperoxide-containing substituted moiety to a hydroxyl moiety thereby providing an isomeric mixture comprising a major amount of a para-branched mono-alkyl-substituted hydroxyaromatic compound.

First claim

What is claimed is:

1. A process for preparing an isomeric mixture comprising a major amount of a para-branched mono-alkyl-substituted hydroxyaromatic compound, the process comprising the steps of:
(a) providing an isomeric mixture comprising a major amount of a para-di(alkyl-substituted)aromatic compound; wherein a first alkyl substituent is a C 3 to C 8 alkyl moiety and a second alkyl substituent is a C 4+n to C 8+n branched alkyl moiety, wherein n is 0 to 42 and further wherein the second alkyl substituent is at least one carbon atom greater than the first alkyl substituent;
(b) subjecting the isomeric mixture comprising a major amount of a para-di(alkyl-substituted)aromatic compound to oxidation conditions in the presence of an oxygen-containing source, thereby converting the first alkyl substituent which is a C 3 to C 8 alkyl moiety to a hydroperoxide-containing substituted moiety to produce a mixture comprising a major amount of a para-branched alkyl-substituted, hydroperoxide-containing substituted aromatic compound; and
(c) converting the hydroperoxide-containing substituted moiety to a hydroxyl moiety thereby providing a mixture comprising a major amount of a para-branched mono-alkyl-substituted hydroxyaromatic compound.

2. The process of claim 1 , wherein the second alkyl substituent is derived from a C 4 to C 50 branched alpha olefin.

3. The process of claim 1 , wherein the mixture of step (a) is obtained from the reaction of a monoalkylaromatic compound and one or more branched alkylating agents in the presence of an acidic catalyst.

4. The process of claim 3 , wherein the one or more branched alkylating agents is a C 4 to C 50 branched alpha olefin.

5. The process of claim 3 , wherein the acidic catalyst is an acidic zeolite catalyst.

6. The process of claim 3 , the molar ratio of the monoalkylaromatic compound to the one or more branched alkylating agents is in the range of about 0.5:2 to about 2:0.5.

7. The process of claim 1 , wherein the oxygen-containing source is air.

8. The process of claim 1 , wherein step (b) is carried out in the presence of a free radical initiator.

9. The process of claim 8 , wherein the free radical initiator is a peroxy compound or azo compound.

10. The process of claim 1 , wherein the oxidation conditions for step (b) comprise a temperature ranging from about 70° C. to about 200° C.

11. The process of claim 1 , wherein step (c) is carried out in the presence of a catalyst.

12. The process of claim 11 , wherein the catalyst is selected from the group consisting of sulfuric acid, perchloric acid, phosphoric acid, hydrochloric acid, p-toluenesulfonic acid, ferric chloride, boron trifluoride, sulfur dioxide and sulfur trioxide.

13. The process of claim 1 , wherein the isomeric mixture contains about 60 mole % or greater of the para-branched mono-alkyl-substituted hydroxyaromatic compounds with the remaining isomeric mixture comprising ortho isomers of the mono-alkyl-substituted hydroxyaromatic compound.

14. The process of claim 1 , wherein the isomeric mixture contains about 80 mole % or greater of the para-branched mono-alkyl-substituted hydroxyaromatic compounds with the remaining isomeric mixture comprising ortho isomers of the mono-alkyl-substituted hydroxyaromatic compound.

15. The process of claim 1 , wherein the isomeric mixture contains about 90 mole % or greater of the para-branched mono-alkyl-substituted hydroxyaromatic compounds with the remaining isomeric mixture comprising ortho isomers of the mono-alkyl-substituted hydroxyaromatic compound.

16. The process of claim 1 , wherein the isomeric mixture contains about 95 mole % or greater of the para-branched mono-alkyl-substituted hydroxyaromatic compounds with the remaining isomeric mixture comprising ortho isomers of the mono-alkyl-substituted hydroxyaromatic compound.

17. The process of claim 1 , wherein the isomeric mixture contains about 99 mole % or greater of the para-branched mono-alkyl-substituted hydroxyaromatic compounds with the remaining isomeric mixture comprising ortho isomers of the mono-alkyl-substituted hydroxyaromatic compound.

18. A process comprising the steps of:
(a) providing an isomeric mixture comprising a major amount of a para-di(alkyl-substituted)aromatic compound of formula I:

wherein R and R 1 are the same or different alkyl group such that the combined number of carbon atoms is no more than 8 carbon atoms, and R 2 is a branched alkyl group of from 4 to 50 carbon atoms, wherein R 2 is at least one carbon atom greater than the combined number of carbon atoms of R and R 1 ;
(b) subjecting the isomeric mixture comprising a major amount of the para-di(alkyl-substituted)aromatic compound of formula I to oxidation conditions in the presence of an oxygen-containing source to produce an isomeric mixture comprising a major amount of a para-branched alkyl-substituted, hydroperoxide-containing substituted aromatic compound of formula II:

wherein R, R 1 and R 2 have the aforestated meanings; and
(c) converting the hydroperoxide-containing substituted moiety of the para-branched alkyl-substituted, hydroperoxide-containing substituted aromatic compound of formula II to a hydroxyl moiety thereby providing an isomeric mixture comprising a major amount of a para-branched mono-alkyl-substituted hydroxyaromatic compound of formula III:

wherein R 2 has the aforestated meaning.

Assignees

• Chevron Oronite Co

Inventors

• Mahieux Cedrick
• Campbell Curtis Bay
• Kuperman Alexander

Classifications

• C07C2529/18

  of the mordenite type · CPC title

• C07C407/00

  Preparation of peroxy compounds · CPC title

• C10M2207/023

  having hydroxy groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C10N2040/252

  Diesel engines · CPC title

• C10N2070/00

  Specific manufacturing methods for lubricant compositions · CPC title