Natural Oil Derivatives Including Primary Amine Functional Groups
A compound has Structure I: where R 1 and R 2 independently are C 2 -C 12 alkyl groups, X 1 is a C 4 -C 28 alkyl or alkenyl group, and R 3 is H or is a bis(aminoalkyl)amide group having Structure II: where R 4 and R 5 independently are C 2 -C 12 alkyl groups. The compound may be a reaction product of a metathesized natural oil and a bis(aminoalkyl)amine.
1 . A compound having Structure I:
where R 1 and R 2 independently are C 2 -C 12 alkyl groups,
X 1 is a C 4 -C 28 alkyl or alkenyl group, and
R 3 is selected from the group consisting of H and a bis(aminoalkyl)amide group having Structure II:
where R 4 and R 5 independently are C 2 -C 12 alkyl groups.
2 . The compound of claim 1 , where R 1 , R 2 , R 4 and R 5 independently are C 2 -C 6 alkyl groups.
3 . The compound of claim 1 , where X 1 is a C 8 -C 22 alkyl or alkenyl group.
4 . The compound of claim 1 , where X 1 is a C 10 -C 16 alkyl or alkenyl group.
5 . The compound of claim 1 , having Structure III:
where X 2 is a C 4 -C 28 alkyl or alkenyl group.
6 . The compound of claim 1 , where R 3 is the bis(aminoalkyl)amide group.
7 . The compound of claim 6 , where X 1 is a C 8 -C 22 alkyl or alkenyl group.
8 . The compound of claim 6 , where X 1 is a C 10 -C 16 alkyl or alkenyl group.
9 . The compound of claim 6 , having Structure IV:
where X 3 is a C 4 -C 28 alkyl or alkenyl group.
10 . An (aminoalkyl)amide composition, comprising:
the reaction product of
a metathesized natural oil and
a bis(aminoalkyl)amine.
11 . The (aminoalkyl)amide composition of claim 10 , where the natural oil is selected from the group consisting of vegetable oils, algal oils, animal fats, tall oils, derivatives thereof, and combinations thereof.
12 . The (aminoalkyl)amide composition of claim 10 where the natural oil is selected from the group consisting of canola oil, rapeseed oil, coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, soybean oil, sunflower oil, linseed oil, palm kernel oil, tung oil, jatropha oil, mustard oil, camelina oil, pennycress oil, hemp oil, algal oil, castor oil, lard, tallow, poultry fat, yellow grease, fish oil, tall oils, and combinations thereof.
13 . The (aminoalkyl)amide composition of claim 10 , where the bis(aminoalkyl)amine is selected from the group consisting of bis(2-aminopropyl)amine, N-2-aminopropyl-N-aminoethylmine, diethylenetriamine, and combinations thereof.
14 . The (aminoalkyl)amide composition of claim 10 , where the metathesized natural oil comprises metathesized soybean oil, and the bis(aminoalkyl)amine comprises diethylenetriamine.
15 . The (aminoalkyl)amide composition of claim 14 , where the reaction product comprises at least one of a compound having Structure III:
where X 2 is a C 4 -C 28 alkenyl group, and
a compound having Structure IV:
where X 3 is a C 4 -C 28 alkyl or alkenyl group.
16 . A method of making an (aminoalkyl)amide composition, comprising:
forming a reaction mixture comprising a metathesized natural oil and a bis(aminoalkyl)amine; and
forming a product mixture comprising an (aminoalkyl)amide formed from the metathesized natural oil and the bis(aminoalkyl)amine.
17 . The method of claim 16 , where the natural oil is selected from the group consisting of vegetable oils, algal oils, animal fats, tall oils, derivatives thereof, and combinations thereof.
18 . The method of claim 16 , where the natural oil is selected from the group consisting of canola oil, rapeseed oil, coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, soybean oil, sunflower oil, linseed oil, palm kernel oil, tung oil, jatropha oil, mustard oil, camelina oil, pennycress oil, hemp oil, algal oil, castor oil, lard, tallow, poultry fat, yellow grease, fish oil, tall oils, and combinations thereof.
19 . The method of claim 16 , where the bis(aminoalkyl)amine is selected from the group consisting of bis(2-aminopropyl)amine, N-2-aminopropyl-N-aminoethylmine, diethylenetriamine, and combinations thereof.
20 . (canceled)
21 . The method of claim 16 , where the reaction mixture further comprises a base.
22 . (canceled)
23 . The method of claim 16 , where the metathesized natural oil comprises metathesized soybean oil, and the bis(aminoalkyl)amine comprises diethylenetriamine.
24 . The method of claim 16 , where the product mixture comprises at least one of a compound having Structure III:
where X 2 is a C 4 -C 28 alkyl or alkenyl group, and
a compound having Structure IV:
where X 3 is a C 4 -C 28 alkyl or alkenyl group.
25 . (canceled)