IP Library Granted Patent US 7,009,072
Granted Patent B2
US 7,009,072 · App. 10/674,896 · Granted Mar 7, 2006

Method for producing lubricant detergents

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Quick Facts
Patent No.
US 7,009,072
App. No.
10/674,896
Granted
Mar 7, 2006
Kind
B2
Abstract

The invention is a process for producing alkaline earth metal salicylates for use as lubricant detergents and to compositions prepared by the process. The process comprises two steps. Step 1 is the alkylation of salicylic acid is conducted using C 14 or greater linear α-olefins to produce alkyl salicylic acids in commercially acceptable yields. The alkylation conditions produce predominately mono-substituted para alkyl salicylic acids that are oil soluble. Step 2 is the oil soluble acid is subsequently neutralized and overbased by carbonation of lime using CO 2 in the presence of a promoter and a surfactant. The reaction mixture after overbasing is filtered and solvents are removed by distillation. Alternatively, alkyl salicylic acid can be reacted with a previously overbased alkaline earth sulfonate, e.g., calcium sulfonate, to produce alkaline earth salicylate salts comprising varying percentages of dispersed alkaline earth carbonate salts. In this method, no filtration of the end product is required, and, thus, it is commercially preferred.

Claims (16)

1. A process for producing alkaline earth metal salicylates comprising the steps of:

A) alkylating salicylic acid with a linear α-olefin comprising at least 14 carbon atoms in the presence of a strong acid catalyst to form an oil soluble alkylated salicylic acid;

B) neutralizing the oil soluble alkylated salicylic acid;

C) overbasing the oil soluble alkylated salicylic acid by carbonation of lime using CO 2 in the presence of a promoter and a surfactant;

D) filtering the product of C); and

E) removing solvents by distillation.

2. The process of claim 1 wherein the strong acid catalyst is anhydrous methanesulfonic acid.

3. The process of claim 1 wherein the alkylation step is carried out at a temperature in the range of from about 50 to about 200° C.

4. The process of claim 1 wherein the linear α-olefin is selected from the group consisting of 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene, 1-docosene, 1-tetracosene, and mixtures of the foregoing.

5. A process for producing alkali metal or alkaline earth metal salicylates comprising the steps of:

A) alkylating salicylic acid with a linear α-olefin comprising at least 14 carbon atoms in the presence of a strong acid catalyst to form an oil soluble alkylated salicylic acid;

B) reacting the oil soluble alkylated salicylic acid with a previously overbased detergent selected from the group consisting of overbased alkali or alkaline earth sulfonates, phenates, or carboxylates to produce alkali or alkaline earth salicylate salts comprising varying percentages of dispersed alkali or alkaline earth carbonate salts.

6. The process of claim 5 wherein the strong acid catalyst is anhydrous methanesulfonic acid.

7. The process of claim 5 wherein the alkylation step is carried out at a temperature in the range of from about 50 to about 200° C.

8. The process of claim 5 wherein the linear α-olefin is selected from the group consisting of 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene, 1-docosene, 1-tetracosene, and mixtures of the foregoing.

9. The process of claim 5 wherein the overbasing step is carried out it the presence of a promoter.

Assignments (10)
RELEASE OF SECURITY INTEREST Recorded Mar 13, 2024
From: CITIBANK N.A., AS ADMINISTRATIVE AGENT
To: APPLIED MEDICAL RESOURCES CORPORATION
Reel/Frame 066796/0262 →
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 →
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 →
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 →
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 →
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 →
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 →
SECURITY AGREEMENT Recorded May 12, 2009
From: CHEMTURA CORPORATION; A & M CLEANING PRODUCTS, LLC; AQUA CLEAR INDUSTRIES, LLC; ASCK, INC.; ASEPSIS, INC.; BIOLAB TEXTILE ADDITIVES, LLC; BIO-LAB, INC.; CNK CHEMICAL REALTY CORPORATION; CROMPTON HOLDING CORPORATION; CROMPTON COLORS INCORPORATED; CROMPTON MONOCHEM, INC.; 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.; BIOLAB COMPANY STORE, LLC; BIOLAB FRANCHISE COMPANY, LLC; GLCC LAUREL, LLC
To: CITIBANK, N.A.
Reel/Frame 022668/0658 →
ASSIGNMENT OF 50% INTEREST Recorded Aug 11, 2004
From: CROMPTON CO./CIE
To: CROMPTON CORPORATION
Reel/Frame 015672/0761 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 30, 2003
From: MUIR, RONALD J.
To: CROMPTON CO./CIE
Reel/Frame 014844/0329 →