# US 11,028,043 B2 · N-hydroxyalkylated polyamines, methods of making n-hydroxyalkylated polyamines, and fluids containing an n-hydroxyalkylated polyamine

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- Number: US 11,028,043 B2
- Document ID: US11028043B2
- Status: Granted
- Kind: B2
- Application number: 16/853,336
- Filed: 2020-04-20
- Published: 2020-08-06
- Granted: 2021-06-08
- Earliest claimed: 2018-01-03
- Assignees: Saudi Arabian Oil Company
- Applicants: Saudi Arabian Oil Company
- Inventors: Matthew Hilfiger; B. Raghava Reddy
- Web page: https://patentgrep.com/patent/US11028043B2

## CPC

- C07C 213/00: Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07B 41/02: of hydroxy or O-metal groups
- C07C 213/04: by reaction of ammonia or amines with olefin oxides or halohydrins
- C07C 215/10: with one amino group and at least two hydroxy groups bound to the carbon skeleton
- C07C 215/14: the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by amino groups
- C09K 8/36: Water-in-oil emulsions
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## 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.

## Claims

### Claim 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:
R1 and R2 are independently a —C or —CH group;
R3 is an aliphatic hydrocarbyl; and
R4 and R5 are independently acyclic hydrocarbyls, or R1, R2, R4, and R5 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 C2-C20 acyclic hydrocarbyls, or unsaturated C2-C20 acyclic hydrocarbyls.

### Claim 2 (depends on 1)

The method of claim 1, where R3 is a saturated or unsaturated C2-C20 acyclic hydrocarbyl group.

### Claim 3 (depends on 1)

The method of claim 1, in which the produced N-hydroxyalkylated polyamine is of Formula (I):
where:
R1 and R2 are independently a —C or —CH group;
R3 is an aliphatic hydrocarbyl;
R4 and R5 are independently acyclic hydrocarbyls, or R1, R2, R4, and R5 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 C2-C20 acyclic hydrocarbyls, or unsaturated C2-C20 acyclic hydrocarbyls; and
R6, R7, R8, and R9 are independently acyclic hydrocarbyls or acyclic heterohydrocarbyls.

### Claim 4 (depends on 3)

The method of claim 3, wherein in Formula (I), R1, R2, R4, and R5 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 C2-C20 acyclic hydrocarbyls, or unsaturated C2-C20 acyclic hydrocarbyls.

### Claim 5 (depends on 1)

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.

### Claim 6 (depends on 1)

The method of claim 1, where the reacting step is a ring-opening epoxide reaction.