Methods of making compounds having antidegradant and antifatigue efficacy

Patent metadata

Field	Value
Publication number	US-10160718-B2
Application number	US-201715618298-A
Country	US
Kind code	B2
Filing date	Jun 9, 2017
Priority date	Dec 22, 2015
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

A method of making antidegradant compounds is disclosed, in which a p-phenylenediamine is reacted with an alpha-hydroxy carbonyl compound to thereby obtain an enediamine, which is reduced to thereby obtain a mixture comprising the antidegradant compound.

First claim

The invention claimed is:

1. A method of making an antidegradant compound, the method comprising:
reacting a p-phenylenediamine corresponding to formula IV:

wherein X is selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen;
with an alpha-hydroxy carbonyl compound corresponding to formula

wherein R 1 and R 3 are each independently selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen,
and wherein R 1 and R 3 may optionally be bridged by a polymethylene group;

to thereby obtain an enediamine; and
reducing the enediamine to thereby obtain a mixture comprising the antidegradant compound according to formula I:

wherein X is each independently selected from the group consisting of alkyl, aryl, alkylaryi groups and hydrogen;
wherein R 1 and R 3 are each independently selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen; and
wherein R 1 and R 3 may optionally be bridged by a polymethylene group to form a cycloalkyl.

2. The method of claim 1 , wherein the p-phenylenediamine comprises 4-aminodiphenvlamine.

3. The method of claim 1 , wherein the alpha-hydroxy carbonyl comprises one or more of acetoin acetoin, acetol, and benzoin.

4. The method of claim 1 , wherein the alpha-hydroxy carbonyl comprises acetoin, and wherein the p-phenylenediamine and the alpha-hydroxy carbonyl are reacted in the presence of a solvent and an acid catalyst.

5. The method of claim 4 , wherein the acid catalyst comprises one or more of formic acid, acetic acid, propionic acid, p-toluenesulfonic acid, camphorsulfonic acid, hydrochloric acid, sulfuric acid, phosphoric acid, and a solid-supported acidic resin.

6. The method of claim 4 , wherein the solvent comprises methylisobutylketone and the mixture comprising the antidegradant compound further comprises N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine.

7. The method of claim 4 , wherein the solvent comprises acetone and the mixture comprising the antidegradant compound further comprises N-isopropyl-N′-phenyl-p-phenylenediamine.

8. The method of claim 1 , wherein the enediamine is reduced by hydrogenation in the presence of: (a) a solvent, (b) a homogeneous or heterogeneous metal catalyst, and (c) one or more of hydrogen gas, formic acid, or a formic acid salt.

9. The method of claim 1 , wherein the step of reacting the p-phenylenediamine with the alpha-hydroxy carbonyl and the step of reducing the enediamine thereby obtained are carried out in sequence, with optional isolation of the intermediate diimine compound.

10. The method of claim 1 , wherein the step of reacting the p-phenylenediamine with the alpha-hydroxy carbonyl and the step of reducing the enediamine thereby obtained are carried out simultaneously in the same reaction mixture.

11. The method of claim 1 , wherein the antidegradant compound comprises N,N′-(butane-2,3-diyl)bis(N-phenylbenzene-1,4-diamine).

Assignees

• Eastman Chem Co

Inventors

• Boone Matthew Allen
• Fields Jr Donald L
• Ignatz-Hoover Frederick

Classifications

• C10N2030/08

  Resistance to extreme temperature · CPC title

• C10L1/223

  having at least one amino group bound to an aromatic carbon atom {(C10L1/221, C10L1/2227 take precedence)} · CPC title

• C10M133/12

  having amino groups bound to a carbon atom of a six-membered aromatic ring · CPC title

• C10N2030/10

  Inhibition of oxidation, e.g. anti-oxidants · CPC title

• C07C209/18

  with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings · CPC title