Transesterification composition of fatty acid esters, and uses thereof

• US 20080020956A1
• Filed: 06/25/2007
• Published: 01/24/2008
• Est. Priority Date: 08/02/2000
• Status: Active Grant

• Current Assignee: MJ Research & Development LP
• Original Assignee: Gulf Research and Development Company
• Inventors: Duffy, Bryan, Mosier, Benjamin
• Granted Patent: US 7,968,504 B2
• Time in Patent Office: Days
• US Class Current: 508/421
• CPC Class Codes: C07C 305/06 Hydrogenosulfates
• CPC Class Codes: C07C 67/03 by reacting an ester group with a hydroxy group
• CPC Class Codes: C07C 69/732 of unsaturated hydroxy carboxylic acids
• CPC Class Codes: C07F 9/113 with unsaturated acyclic alcohols
• CPC Class Codes: C07F 9/143 with unsaturated acyclic alcohols
• CPC Class Codes: C09K 5/00 Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
• CPC Class Codes: C10M 101/04 Fatty oil fractions
• CPC Class Codes: C10M 105/32 Esters
• CPC Class Codes: C10M 109/00 Lubricating compositions characterised by the base-material being a compound of unknown or incompletely defined constitution C10M101/00 takes precedence
• CPC Class Codes: C10M 129/68 Esters epoxidised C10M129/66
• CPC Class Codes: C10M 159/08 Fatty oils
• CPC Class Codes: C10M 171/008 Lubricant compositions compatible with refrigerants
• CPC Class Codes: C10M 2207/28 Esters
• CPC Class Codes: C10M 2207/40 Fatty vegetable or animal oils
• CPC Class Codes: C10M 2207/404 obtained from genetically modified species
• CPC Class Codes: C10N 2040/00 Specified use or application for which the lubricating composition is intended
• CPC Class Codes: C10N 2040/04 Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
• CPC Class Codes: C10N 2040/042 for automatic transmissions
• CPC Class Codes: C10N 2040/044 for manual transmissions
• CPC Class Codes: C10N 2040/046 for traction drives
• CPC Class Codes: C10N 2040/08 : Hydraulic fluids, e.g. brake-fluids
• CPC Class Codes: C10N 2040/16 : Dielectric; Insulating oil or insulators
• CPC Class Codes: C10N 2040/17 : for electric contacts
• CPC Class Codes: C10N 2040/22 : with essential removal of material , e.g. cutting, grinding or drilling
• CPC Class Codes: C10N 2040/25 : Internal-combustion engines
• CPC Class Codes: C10N 2040/251 : Alcohol-fuelled engines
• CPC Class Codes: C10N 2040/255 : Gasoline engines
• CPC Class Codes: C10N 2040/28 : Rotary engines
• CPC Class Codes: C10N 2040/30 : Refrigerators lubricants or compressors lubricants
• CPC Class Codes: C10N 2040/32 : Wires, ropes or cables lubricants
• CPC Class Codes: C10N 2040/34 : Lubricating-sealants
• CPC Class Codes: C10N 2040/36 : Release agents or mold release agents
• CPC Class Codes: C10N 2040/38 : Conveyors or chain belts
• CPC Class Codes: C10N 2040/40 : Generators or electric motors in oil or gas winning field
• CPC Class Codes: C10N 2040/42 : Flashing oils or marking oils
• CPC Class Codes: C10N 2040/44 : Super vacuum or supercritical use
• CPC Class Codes: C10N 2040/50 : Medical uses
• CPC Class Codes: C11C 3/003 : by esterification of fatty acids with alcohols C11C3/02 takes precedence
• CPC Class Codes: C11C 3/10 : Ester interchange

Abstract

This invention is a composition that includes a transesterified fatty acid ester resulting from the reaction of a fatty acid ester, in the presence of an acid, with a hydroxyl-containing compound. The fatty acid esters of the invention are selected from those with a carbon number of eight to twenty. The hydroxyl-containing compound is an alcohol having a carbon number between one and eighteen. The resulting composition is useful as a lubricant, as a heat transfer agent, as a rheological modifier and as a corrosion/moisture inhibitor, among other uses.

Claims

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2. A composition comprising reaction products from a reaction of a ricinoleic acid with propyl alcohol in the presence of a phosphorous-containing acid, the reaction products including a propyl ester of ricinoleic acid formed through partial transesterification, and a phosphorus-containing compound, the reaction products exhibiting solubility with refrigerant, hydrocarbons or fuel solvents.

4. The composition of claim 2 wherein castor oil is used in the reaction to supply the ricinoleic acid.

11. The composition of claim 2 wherein the reaction produces a phosphated fatty acid ester.

12. The composition of claim 2 wherein the reaction produces glycerol ricinoleate and n-propyl ricinoleate.

13. The composition of claim 2 wherein the fatty acid ester is dimerized or trimerized.

16. The composition of claim 2 wherein the acid is phosphoric acid.

19. The composition of claim 2 wherein the propyl ester of ricinoleic acid contains a phosphate functional group.

23. The composition of claim 2 wherein the propyl alcohol comprises isopropyl alcohol.

24. The composition of claim 2 further comprising reaction with a second alcohol wherein the second alcohol is butyl alcohol.

25. The composition of claim 2 wherein the propyl alcohol comprises n-propyl alcohol.

33. The composition of claim 2 further comprising a miscibility-enhancement additive effective to increase miscibility with naphthenes, paraffins, alkyl benzenes, mineral oils, polyol esters, polyalphaolefins, polyalkylene glycols, polybutenes, polyvinyl ethers and substituted hydrocarbons.

58. A process for lubrication of a lubricant-dependant system with a fluid comprising adding an effective amount of the composition of claim 2 to the lubricant-dependant system in the fluid.

59. A process for increasing heat transfer in a heat transfer system capable of receiving a heat transfer fluid comprising adding an effective amount of the composition of claim 2 to the heat transfer fluid.

60. A process for modification of rheological properties of a hydro-mechanical fluid comprising adding an effective amount of the composition of claim 2 to the hydro-mechanical fluid.

61. A process for inhibition of corrosion for a corrosion-susceptible mechanical system comprising contacting the corrosion-susceptible mechanical system with a fluid having an effective amount of the composition of claim 2.

62. A process for inhibition of moisture for a moisture-susceptible mechanical system comprising contacting the moisture-susceptible mechanical system with a fluid having an effective amount of the composition of claim 2

94. The process of claim 58 further comprising a miscibility-enhancement additive effective to increase miscibility with napthenes, paraffins, alkyl benzenes, mineral oils, polyol esters, polyalphaolefins, polyalkylene glycols, polybutenes, polyvinyl ethers and substituted hydrocarbons.

98. The process of claim 58 further comprising reacting the transesterified fatty acid ester with a second compound having an acetyl, alkyl oxy, alkyl propoxy or carboxyl functional group to form a further-substituted fatty acid ester that includes an acetyl, alkyl oxy, alkyl propoxy or ester functional group.

99. The process of claim 58 wherein the lubricant-dependant system is selected from the group comprising a mechanical device, a refrigeration system, a motor oil system, an engine, an engine part, a gear, a drilling operation and a reciprocating combustion engine.

100. The process of claim 58 wherein the composition is capable of providing lubrication at temperatures up to about 350 degrees C.

101. The process of claim 58 wherein the composition lubricant is capable of providing lubrication below 0 degrees C.

102. The process of claim 59 wherein the heat transfer system is selected from the group comprising a coolant system, a hydraulic braking system, a hydraulic transmission system, a refrigeration system and an air-conditioning system.

103. The process of claim 60 wherein the hydro-mechanical fluids are functional fluids.

104. The process of claim 60 wherein the hydro-mechanical fluids are selected from the group consisting of radiator fluid, drilling fluid, engine fluid, anti-corrosive fluid, transmission fluid, hydraulic fluid, brake fluid, dielectric fluid, heat transfer fluid and cutting fluid.

105. The process of claim 61 wherein the mechanical system is a reciprocating combustion engine, a hydraulic braking system, a hydraulic transmission system or a coolant system.

106. The composition of claim 2 wherein:

The composition is effective in providing lubrication to a mechanical system;

the transesterified fatty acid ester has an HLB between about 0.5 and 4.8; and

the transesterified fatty ester exhibits in excess of 1000 pounds force load to failure.

110. A process for cleaning mechanical system comprising contacting the mechanical system with a fluid having an effective amount of the composition of claim 2.

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9. The composition of claim 8 wherein the transesterified fatty acid ester includes ricinoleic n-propyl ester.

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112. The transesterified fatty acid ester of claim 111 wherein the compound containing a hydroxyl functional group is n-propyl alcohol.

113. The transesterified fatty acid ester of claim 111 wherein the acid is phosphoric acid.

114. A method of making a phosphorus-containing composition comprising the steps of:

reacting a fatty acid ester comprising ricinoleic acid with propyl alcohol in the presence of a phosphorus-containing acid such that the reaction products include a propyl ester of ricinoleic acid formed through partial transesterification and a phosphorus-containing compound, the phosphorus-containing composition exhibiting solubility with refrigerant, hydrocarbons or fuel solvents.