IP Library Granted Patent US 7,964,002
Granted Patent B2
US 7,964,002 · App. 11/453,586 · Granted Jun 21, 2011

Antioxidant additive for biodiesel fuels

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Quick Facts
Patent No.
US 7,964,002
App. No.
11/453,586
Granted
Jun 21, 2011
Kind
B2
Abstract

A synergistic combination antioxidant mixture that provides excellent characteristics for biodiesel fuel compositions, when incorporated therein.

Claims (22)

1. A composition comprising

(a) biodiesel fuel and

(b) an antioxidizing effective amount of a mixture of

(i) at least one aromatic diamine selected from the group consisting of N-(1,4-dimethylbutyl)-N′-phenyl-p-phenylenediamine, N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine, and N,N′-di-sec-butyl-p-phenylenediamine and

(ii) at least one sterically hindered phenol selected from the group consisting of 2,4-di-methyl-6-tert-butyl phenol, 2-methyl-6-tert-butyl phenol, 2,6-di-tert-butyl-4-methyl phenol, and 1,2,3-trihydroxybenzene

wherein the ratio of aromatic amine to hindered phenol is about 1:1 by weight.

2. The composition of claim 1 wherein the biodiesel fuel comprises methyl esters of soybean oil, mustard seed oil, rapeseed oil, canola oil or tallow.

3. The composition of claim 1 wherein the mixture is present in the biodiesel fuel in an amount of about 1 to about 10,000 ppm.

4. The composition of claim 3 wherein the mixture is present in the biodiesel fuel in an amount from about 50 to about 5,000 ppm.

5. The composition of claim 4 wherein the mixture is present in the biodiesel fuel in an amount from about 100 to about 2,000 ppm.

6. The composition of claim 1 wherein the aromatic diamine of the mixture is a blend of N-(1,4-dimethylbutyl)-N′-phenyl-1,4-phenylenediamine and N-(1,3-dimethylbutyl)-N′-phenyl-1,4-phenylenediamine), and the sterically hindered phenol of the mixture is 2,6-di-tert-butyl-4-methyl phenol.

7. The composition of claim 1 wherein the aromatic diamine of the mixture is a blend of N-(1,4-dimethylbutyl)-N′-phenyl-1,4-phenylenediamine and N-(1,3-dimethylbutyl)-N′-phenyl-1,4phenylenediamine), and the sterically hindered phenol of the mixture is 1,2,3-trihydroxybenzene.

8. The composition of claim 1 further comprising at least one other component selected from the group consisting of dispersants/detergents, octane improvers, cetane improvers, carrier fluids, demulsifiers, antifoam agents, anti-icing additives, biocides, combustion improvers, alkali or alkaline-earth metal detergents, drag reducers, metal deactivators, lubricity additives, dyes, markers, odor masks, odorants and stability improvers.

9. The composition of claim 2 wherein the mixture is present in the biodiesel fuel in an amount of about 50 to about 5,000 ppm.

10. The composition of claim 2 wherein the aromatic diamine of the mixture is a blend of N-(1,4-dimethylbutyl)-N′-phenyl-1,4-phenylenediamine and N-(1,3-dimethylbutyl)-N′-phenyl-1,4-phenylenediamine), and the sterically hindered phenol of the mixture is 2,6-di-tert-butyl-4-methyl phenol.

11. The composition of claim 2 wherein the aromatic diamine of the mixture is a blend of N-(1,4-dimethylbutyl)-N′-phenyl-1,4-phenylenediamine and N-(1,3-dimethylbutyl)-N′-phenyl-1,4phenylenediamine), and the sterically hindered phenol of the mixture is 1,2,3-trihydroxybenzene.

12. The composition of claim 2 further comprising at least one other component selected from the group consisting of dispersants/detergents, octane improvers, cetane improvers, carrier fluids, demulsifiers, antifoam agents, anti-icing additives, biocides, combustion improvers, alkali or alkaline-earth metal detergents, drag reducers, metal deactivators, lubricity additives, dyes, markers, odor masks, odorants and stability improvers.

13. The composition of claim 2 wherein the biodiesel fuel comprises methyl esters of rapeseed oil or tallow.

14. The composition of claim 13 wherein the mixture is present in the biodiesel fuel in an amount of about 50 to about 5,000 ppm.

15. The composition of claim 13 wherein the aromatic diamine of the mixture is a blend of N-(1,4-dimethylbutyl)-N′-phenyl-1,4-phenylenediamine and N-(1,3-dimethylbutyl)-N′-phenyl-1,4-phenylenediamine), and the sterically hindered phenol of the mixture is 2,6-di-tert-butyl-4-methyl phenol.

16. The composition of claim 13 wherein the aromatic diamine of the mixture is a blend of N-(1,4-dimethylbutyl)-N′-phenyl-1,4-phenylenediamine and N-(1,3-dimethylbutyl)-N′-phenyl-1,4phenylenediamine), and the sterically hindered phenol of the mixture is 1,2,3-trihydroxybenzene.

17. The composition of claim 13 further comprising at least one other component selected from the group consisting of dispersants/detergents, octane improvers, cetane improvers, carrier fluids, demulsifiers, antifoam agents, anti-icing additives, biocides, combustion improvers, alkali or alkaline-earth metal detergents, drag reducers, metal deactivators, lubricity additives, dyes, markers, odor masks, odorants and stability improvers.

Assignments (11)
MERGER AND CHANGE OF NAME Recorded Sep 7, 2018
From: CHEMTURA CORPORATION; LANXESS SOLUTIONS US INC.
To: LANXESS SOLUTIONS US INC.
Reel/Frame 046811/0266 →
RELEASE OF AMENDED AND RESTATED SECOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 12, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
Reel/Frame 042452/0759 →
RELEASE OF THIRD LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 12, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
Reel/Frame 042452/0894 →
RELEASE OF FIRST LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 11, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
Reel/Frame 042447/0508 →
RELEASE OF SECOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 11, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
Reel/Frame 042449/0001 →
AMENDED AND RESTATED SECOND LIEN INTELLECTUAL PROPERY SECURITY AGREEMENT Recorded Jul 18, 2014
From: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
To: BANK OF AMERICA, N.A.
Reel/Frame 033360/0225 →
THIRD LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Jul 18, 2014
From: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
To: BANK OF AMERICA, N.A.
Reel/Frame 033360/0325 →
FIRST LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT. Recorded Mar 21, 2011
From: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 026028/0622 →
INTELLECTUAL PROPERTY SECURITY RELEASE AGREEMENT Recorded Mar 21, 2011
From: CITIBANK, N.A.
To: CHEMTURA CORPORATION; A & M CLEANING PRODUCTS, LLC; ASCK, INC; BIOLAB COMPANY STORE, LLC; AQUA CLEAR INDUSTRIES, LLC; ASEPSIS, INC.; BIOLAB TEXTILES ADDITIVES, LLC; BIOLAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON MONOCHEM, INC.; CNK CHEMICAL REALTY CORPORATION; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GT SEED TREATMENT, INC.; ISCI, INC; GREAT LAKES CHEMICAL GLOBAL, INC.; HOMECARE LABS, INC.; KEM MANUFACTURING CORPORATION; LAUREL INDUSTRIES HOLDINGS, INC.; NAUGATUCK TREATMENT COMPANY; UNIROYAL CHEMICAL COMPANY LIMITED (DELAWARE); MONOCHEM, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC; WRL OF INDIANA, INC.; BIOLAB FRANCHISE COMPANY, LLC
Reel/Frame 026039/0142 →
SECDOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 21, 2011
From: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORORATED; CROMPTON HOLDING CORPORATION; CLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; HAOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
To: BANK OF AMERICA, N. A.
Reel/Frame 027881/0347 →
AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Feb 22, 2010
From: CHEMTURA CORPORATION; A & M CLEANING PRODUCTS, LLC; AQUA CLEAR INDUSTRIES, LLC; ASCK, INC.; ASEPSIS, INC.; BIOLAB COMPANY STORE, LLC; BIOLAB FRANCHISE COMPANY, LLC; BIOLAB TEXTILE ADDITIVES, LLC; BIO-LAB, INC.; CNK CHEMICAL REALTY CORPORATION; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; CROMPTON MONOCHEM, INC.; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; ISCI, INC.; KEM MANUFACTURING CORPORATION; LAUREL INDUSTRIES HOLDINGS, INC.; MONOCHEM, INC.; NAUGATUCK TREATMENT COMPANY; RECREATIONAL WATER PRODUCTS, INC.; UNIROYAL CHEMICAL COMPANY LIMITED (DELAWARE); WEBER CITY ROAD LLC; WRL OF INDIANA, INC.
To: CITIBANK, N.A.
Reel/Frame 023998/0001 →