IP Library Granted Patent US 7,737,297
Granted Patent B2
US 7,737,297 · App. 11/915,218 · Granted Jun 15, 2010

Esterification process of polyols with tertiary alkyl substituted acids

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Quick Facts
Patent No.
US 7,737,297
App. No.
11/915,218
Granted
Jun 15, 2010
Kind
B2
Abstract

A process to prepare polyol esters from tertiary alkyl acid with reduced homo-polymerisation of the polyols. The ester polyol can be used in the synthesis of further polyester resins for coating or structural/composite or lube oil applications.

Claims (10)

1. A process of preparing polyol esters from tertiary alkyl acids comprising reacting a polyol and the tertiary alkyl acid in the presence of an acid catalyst having a pKa from −2 to +2 at a temperature below 180° C., and optionally in presence of an inert organic solvent, wherein the polyol ester is predominantly a mono-ester of the polyol, wherein the acid catalyst is selected from the group consisting of methane sulphonic acid, ethane sulphonic acid, trifluoromethane sulphonic acid, para toluene sulphonic acid, xylene sulphonic acids and combinations thereof.

2. The process of claim 1 , wherein the acid catalyst is methane sulphonic acid or para toluene sulphonic acid.

3. The process of claim 1 , wherein the acid catalyst is used in a range from 0.05 to 4 weight % relative to the weight of the tertiary alkyl acid and the polyol ester.

4. The process claim 1 , wherein the tertiary alkyl acid is represented by the formula (I),

in which R 1 , R 2 are independently aliphatic alkyl radicals of having 1 to 10 carbon atoms, and the total carbon atoms of the three radicals, CH 3 +R 1 +R 2 ranges from 3 to 20.

5. The process claim 1 , wherein the polyol is selected from the group consisting of ethylene glycol, propylene glycol, glycol oligomers having 2 to 10 repeating units, glycerol, neopentyl glycol, trimethylolpropane, pentaerythritol, and combinations thereof.

6. The process of claim 1 , wherein the acid catalyst is used in a range from 0.10 to 2.5 weight % relative to the weight of the tertiary alkyl acid and the polyol ester.

7. The process of claim 1 , wherein the tertiary alkyl acid is represented by formula (I),

in which R 1 , R 2 are independently aliphatic alkyl radicals having 1 to 10 carbon atoms and the total carbon atoms of the three radicals, CH 3 +R 1 +R 2 , ranges from 3 to 13.

8. The process of claim 1 , wherein the polyol is selected from the group consisting of neopentyl glycol, trimethylolpropane, pentaerythritol, and combinations thereof.

Assignments (14)
RELEASE OF SECURITY INTEREST IN PATENTS (TERM LOAN) RECORDED AT REEL/FRAME 049741/0425 Recorded Mar 18, 2022
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: HEXION INC.
Reel/Frame 059435/0473 →
RELEASE OF SECURITY INTEREST IN PATENTS (ABL) RECORDED AT REEL/FRAME 049740/0770 Recorded Mar 18, 2022
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: HEXION INC.
Reel/Frame 059435/0490 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0748 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0823 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: ROYAL BANK OF CANADA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0842 →
PATENT SECURITY INTEREST (TERM LOAN) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049741/0425 →
PATENT SECURITY INTEREST (ABL) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049740/0770 →
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (030146/0970) Recorded Jul 9, 2019
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT AND COLLATERAL AGENT
To: HEXION INC. (FORMERLY KNOWN AS MOMENTIVE SPECIALTY CHEMICALS INC.)
Reel/Frame 049706/0264 →
PATENT SECURITY INTEREST ASSIGNMENT AGREEMENT Recorded Apr 3, 2019
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS THE PRIOR COLLATERAL AGENT
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS THE CURRENT COLLATERAL AGENT
Reel/Frame 048788/0617 →
RELEASE OF SECURITY INTEREST Recorded Feb 23, 2017
From: WILMINGTON TRUST, NATIONAL ASSOCIATION (SUCCESSOR BY MERGER TO WILMINGTON TRUST FSB), AS COLLATERAL AGENT
To: HEXION INC. (FORMERLY KNOWN AS HEXION SPECIALTY CHEMICALS INC.); BORDEN CHEMICAL FOUNDRY, LLC; HEXION INVESTMENTS INC. (FORMERLY KNOWN AS BORDEN CHEMICAL INVESTMENTS, INC.); HEXION U.S. FINANCE CORP.; HSC CAPITAL CORPORATION; LAWTER INTERNATIONAL INC.; HEXION INTERNATIONAL INC. (FORMERLY KNOWN AS BORDEN CHEMICAL INTERNATIONAL INC.); OILFIELD TECHNOLOGY GROUP, INC.; HEXION CI HOLDING COMPANY (CHINA) LLC
Reel/Frame 041793/0001 →
SECURITY INTEREST Recorded Feb 13, 2017
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 041693/0888 →
CHANGE OF NAME Recorded Jan 27, 2015
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: HEXION INC.
Reel/Frame 034817/0806 →
SECURITY AGREEMENT Recorded Feb 5, 2010
From: HEXION LLC; HEXION SPECIALTY CHEMICALS, INC.; BORDEN CHEMICAL FOUNDRY, LLC; BORDEN CHEMICAL INVESTMENTS, INC.; HEXION U.S. FINANCE CORP.; HSC CAPITAL CORPORATION; LAWTER INTERNATIONAL INC.; BORDEN CHEMICAL INTERNATIONAL, INC.; OILFIELD TECHNOLOGY GROUP, INC.; HEXION CI HOLDING COMPANY (CHINA) LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 023905/0451 →
SECURITY INTEREST Recorded Jan 29, 2010
From: HEXION SPECIALTY CHEMICALS, INC.; BORDEN CHEMICAL FOUNDRY, LLC; BORDEN CHEMICAL INVESTMENTS, INC.; HEXION U.S. FINANCE CORP.; HSC CAPITAL CORPORATION; LAWTER INTERNATIONAL INC.; BORDEN CHEMICAL INTERNATIONAL, INC.; OILFIELD TECHNOLOGY GROUP, INC.; HEXION CI HOLDING COMPANY (CHINA) LLC
To: WILMINGTON TRUST FSB, AS COLLATERAL AGENT
Reel/Frame 023963/0038 →