N-hydroxyalkylated polyamines, methods of making n-hydroxyalkylated polyamines, and fluids containing an n-hydroxyalkylated polyamine
Methods of making N-hydroxyalkylated polyamines are provided, in which the method includes reacting a polyamine comprising Formula (XXIV): with a cyclic oxide to produce the N-hydroxyalkylated polyamine, where R 1 and R 2 are independently a —C or —CH group; R 3 is an aliphatic hydrocarbyl; and R 4 and R 5 are independently acyclic hydrocarbyls, or are covalently connected to form an unsaturated cyclic hydrocarbyl.
1. A method of making an N-hydroxyalkylated polyamine comprising:
reacting a polyamine of Formula (XXIV):
with a cyclic oxide to produce the N-hydroxyalkylated polyamine;
where:
R 1 and R 2 are independently a —C or —CH group;
R 3 is an aliphatic hydrocarbyl; and
R 4 and R 5 are independently acyclic hydrocarbyls, or R 1 , R 2 , R 4 , and R 5 are covalently connected to form an unsaturated cyclic hydrocarbyl, wherein the unsaturated cyclic hydrocarbyl is substituted with one or more of alkyl, aminoalkyl, aminoalkoxy, hydroxyl, alkoxyl, alkylthio, amino, halo, haloalkyl, silyl, phosphoryl, sulfonyl, saturated C 2 -C 20 acyclic hydrocarbyls, or unsaturated C 2 -C 20 acyclic hydrocarbyls.
2. The method of claim 1 , where R 3 is a saturated or unsaturated C 2 -C 20 acyclic hydrocarbyl group.
3. The method of claim 1 , in which the produced N-hydroxyalkylated polyamine is of Formula (I):
where:
R 1 and R 2 are independently a —C or —CH group;
R 3 is an aliphatic hydrocarbyl;
R 4 and R 5 are independently acyclic hydrocarbyls, or R 1 , R 2 , R 4 , and R 5 are covalently connected to form an unsaturated cyclic hydrocarbyl, wherein the unsaturated cyclic hydrocarbyl is substituted with one or more of alkyl, aminoalkyl, aminoalkoxy, hydroxyl, alkoxyl, alkylthio, amino, halo, haloalkyl, silyl, phosphoryl, sulfonyl, saturated C 2 -C 20 acyclic hydrocarbyls, or unsaturated C 2 -C 20 acyclic hydrocarbyls; and
R 6 , R 7 , R 8 , and R 9 are independently acyclic hydrocarbyls or acyclic heterohydrocarbyls.
4. The method of claim 3 , wherein in Formula (I), R 1 , R 2 , R 4 , and R 5 are covalently connected to form an unsaturated cyclic hydrocarbyl selected from the group consisting of cyclohexene, benzene, naphthalene, and decahydronaphthalene, wherein the unsaturated cyclic hydrocarbyl is substituted with one or more of alkyl, aminoalkyl, aminoalkoxy, hydroxyl, alkoxyl, alkylthio, amino, halo, haloalkyl, silyl, phosphoryl, sulfonyl, saturated C 2 -C 20 acyclic hydrocarbyls, or unsaturated C 2 -C 20 acyclic hydrocarbyls.
5. The method of claim 1 , where the cyclic oxide is selected from the group consisting of ethylene oxide, butylene oxide, propylene oxide, and combinations thereof.
6. The method of claim 1 , where the reacting step is a ring-opening epoxide reaction.