Fatty amines, amidoamines, and their derivatives from natural oil metathesis
Fatty amine compositions made from a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives are disclosed. In another aspect, fatty amidoamines made by reacting a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with an aminoalkyl-substituted tertiary amine are disclosed. The fatty amines or amidoamines are advantageously sulfonated, sulfitated, oxidized, or reduced. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin.
1. A fatty amidoamine having the formula:
R 3 (R 2 )N(CH 2 ) n NH(CO)R 1
wherein R 1 is —C 9 H 16 —R 4 or —C 16 H 30 —(CO)NH(CH 2 ) n N(R 2 )R 3 ; each of R 2 and R 3 is independently substituted or unsubstituted alkyl, aryl, alkenyl, oxyalkylene, or polyoxyalkylene; R 4 is hydrogen or C 1 -C 7 alkyl; and n=2-8; wherein when R 4 is C 1 -C 7 alkyl, the fatty amidoamine has at least 1 mole % of trans-Δ 9 unsaturation.
2. A derivative made by one or more of sulfonating, sulfitating, or oxidizing the amidoamine of claim 1 .
3. The amidoamine of claim 1 wherein the fatty amidoamine has at least 50 mole % of trans-Δ 9 unsaturation.
4. The amidoamine of claim 1 wherein (i) R 2 and R 3 are methyl and n is 3; (ii) R 2 and R 3 are ethyl and n is 3; (iii) R 2 and R 3 are methyl and n is 2; or (iv) R 2 and R 3 are methyl and n is 4.
5. A fatty amidoamine comprising a reaction product of an aminoalkyl-substituted tertiary amine with (a) a modified triglyceride made by self-metathesis of a natural oil; or (b) an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin.
6. The amidoamine of claim 5 wherein the aminoalkyl-substituted tertiary amine is selected from the group consisting of N,N-dimethyl-1,3-propanediamine (DMAPA), N,N-diethyl-1,3-propanediamine, N,N-dimethyl-1,2-ethanediamine, and N,N-dimethyl-1,4-butanediamine.
7. A derivative made by one or more of sulfonating, sulfitating, or oxidizing the amidoamine of claim 5 .
8. The amidoamine of claim 5 wherein the natural oil is selected from the group consisting of soybean oil, palm oil, rapeseed oil, algal oil, and mixtures thereof.
9. The amidoamine of claim 5 wherein the olefin is a C 2 -C 8 α-olefin or a C 4 -C 9 internal olefin.
10. A laundry detergent formulation comprising the amidoamine of claim 1 .
11. A laundry detergent formulation comprising the amidoamine derivative of claim 2 .
12. A laundry detergent formulation comprising the amidoamine of claim 5 .
13. A laundry detergent formulation comprising the amidoamine derivative of claim 7 .