Chemically modified vegetable oil-based industrial fluid
AssigneeThe United States of America as represented by the Secretary of Agriculture
InventorsSevim Z. Erhan, Atanu Adhvaryu, Zengshe Liu
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Abstract
Triglyceride oils having unsaturated fatty acid substituents are modified to convert sites of unsaturation to C-2 to C-10 diesters. The resulting derivatives are characterized by thermal and oxidative stability, have low temperature performance properties and are environmentally-friendly. They have utility as hydraulic fluids, lubricants, metal working fluids and other industrial fluids. The triglyceride oils are most easily prepared via epoxidized vegetable oils which are converted to the diesters in either a one- or two-step reaction.
Claims22
A modified vegetable triglyceride characterized by the following formula:
- wherein R, R′ and R″ are independently selected from C-7 to C-21 aliphatic fatty acid residues, each including the structures:
- wherein R′″ is H or C-2 to C-10 straight chain or branched hydrocarbon;
- wherein the ratio of R′″=hydrocarbon:R′″=H in said modified triglyceride is at least 90:10;
- wherein m=0-1;
- wherein n=0-3;and
- wherein the average Σn for R, R′ and R″ in said modified triglyceride is at least 1.
A method for preparing a modified vegetable triglyceride characterized by the following formula:
- wherein R, R′ and R″ are independently selected from C-7 to C-21 aliphatic fatty acid residues, each including the structures:
- wherein R′″ is H or C-2 to C-10 straight chain or branched hydrocarbon;
- wherein the ratio of R′″=hydrocarbon:R′″=H in said modified triglyceride is at least 90:10;
- wherein m=0-1;
- wherein n=0-3;and
- wherein the average Σn for R, R′ and R″ in said modified triglyceride is at least 1;
- the method comprising reacting an epoxidized vegetable triglyceride having at least one oxirane ring structure with an anhydride selected from the group consisting of acetic, propionic, butyric, valeric, hexanoic, heptanoic, octanoic, nonanoic and n-decanoic in the presence of a suitable catalyst for simultaneously opening the oxirane ring and activating the anhydride in order to convert each of said oxirane ring structures to a diester derivative.
A method for preparing a modified vegetable triglyceride characterized by the following formula:
- wherein R, R′ and R″ are independently selected from C-7 to C-21 aliphatic fatty acid residues, each including the structures:
- wherein R′″ is H or C-2 to C-10 straight chain or branched hydrocarbon;
- wherein the ratio of R′″=hydrocarbon:R′″=H in said modified triglyceride is at least 90:10;
- wherein m=0″1;
- wherein n=0″3;
- and
- wherein the average Σn for R, R′ and R″ in said modified triglyceride is at least 1;
- the-method comprising:
- a. refluxing an epoxidized vegetable triglyceride having oxirane ring structures in an aqueous solvent in the presence of a strong acid catalyst in order to hydrolyze the oxirane ring to a dihydroxy intermediate;
- b. reacting said dihydroxy intermediate with an anhydride selected from the group consisting of acetic, propionic, butyric, valeric, hexanoic, heptahoic, octanoic, nonanoic and n-decanoic in order to covert said dihydroxy intermediate to a diester derivative.
Dependencies are inferred from the claim text.