N-hydroxyalkylated polyamines, methods of making n-hydroxyalkylated polyamines, and fluids containing an n-hydroxyalkylated polyamine

Patent metadata

Field	Value
Publication number	US-11028043-B2
Application number	US-202016853336-A
Country	US
Kind code	B2
Filing date	Apr 20, 2020
Priority date	Jan 3, 2018
Publication date	Jun 8, 2021
Grant date	Jun 8, 2021

Abstract

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 R1 and R2 are independently a —C or —CH group; R3 is an aliphatic hydrocarbyl; and R4 and R5 are independently acyclic hydrocarbyls, or are covalently connected to form an unsaturated cyclic hydrocarbyl.

First claim

The invention claimed is:

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.

Assignees

• Saudi Arabian Oil Co

Inventors

• Hilfiger Matthew
• Reddy B Raghava

Classifications

• C07C215/14 Primary

  the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by amino groups · CPC title

• C09K8/36

  Water-in-oil emulsions · CPC title

• C07C213/00 Primary

  Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton · CPC title

• C07C215/10

  with one amino group and at least two hydroxy groups bound to the carbon skeleton · CPC title

• C07B41/02

  of hydroxy or O-metal groups · CPC title