# US 2020/0399518 A1 · Additives for oil and gas drilling and production

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- Number: US 2020/0399518 A1
- Document ID: US20200399518A1
- Status: Published application
- Kind: A1
- Application number: 17/010,604
- Filed: 2020-09-02
- Published: 2020-12-24
- Earliest claimed: 2018-10-31
- Assignees: Saudi Arabian Oil Company
- Applicants: Saudi Arabian Oil Company
- Inventors: Ashok Santra; Matthew Gary Hilfiger
- Web page: https://patentgrep.com/patent/US20200399518A1

## CPC

- C09K 8/035: Organic additives
- C09K 8/06: Clay-free compositions (containing inorganic compounds only C09K8/05)
- C07C 213/04: by reaction of ammonia or amines with olefin oxides or halohydrins
- C07C 215/40: with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
- C09K 8/34: Organic liquids
- C09K 8/54: Compositions for in situ inhibition of corrosion in boreholes or wells
- C09K 8/82: Oil-based compositions (C09K8/64 takes precedence)
- C09K 8/86: containing organic compounds
- E21B 41/02: in situ inhibition of corrosion in boreholes or wells
- C09K 2208/12: Swell inhibition, i.e. using additives to drilling or well treatment fluids for inhibiting clay or shale swelling or disintegrating
- C09K 2208/32: Anticorrosion additives
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- E21B: EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS

## Abstract

A quaternary amine composition selected from the group consisting of Formula I, Formula II, Formula III, and combinations of the same. A method of synthesizing a quaternary amine composition comprising the steps of reacting an alkoxylated dimer diamine with a methyl halogen, where the methyl halogen is selected from the group consisting of methyl chloride, methyl iodine, and combinations of the same; and allowing the reaction to proceed to produce the quaternary amine composition, the quaternary amine composition selected from the group consisting of Formula I, Formula II, Formula III, and combinations of the same. A method of treating a well comprising the steps of introducing an additive-containing well fluid to a well, where the additive-containing well fluid comprises a quaternary amine composition and a well fluid, allowing the additive-containing well fluid to interact with the well, and treating the well with the additive-containing fluid.

## Claims

### Claim 1

A method of synthesizing a quaternary amine composition, the method comprising the steps of: reacting an alkoxylated dimer diamine with a methyl halogen to produce the quaternary amine composition, where the methyl halogen is selected from the group consisting of methyl chloride, methyl iodine, and combinations of the same, where the quaternary amine composition comprises Formula I, where Formula I is:
where:
each of R1 and R2 is selected from the group consisting of a carbon atom (C—) and a carbon bonded to a hydrogen (—CH),
each R3 is selected from the group consisting of a saturated aliphatic hydrocarbyl and an unsaturated aliphatic hydrocarbyl,
each R4 is selected from the group consisting of an acyclic hydrocarbyl and an acyclic heterohydrocarbyl,
each of R5 and R6 is selected from the group consisting of a saturated acyclic hydrocarbyl and an unsaturated acyclic hydrocarbyl,
X is selected from the group consisting of an iodine ion (I—), a chlorine ion (Cl—), and combinations of the same.

### Claim 2 (depends on 1)

The method of claim 1, where the step of reacting the alkoxylated dimer diamine with the methyl halogen is at ambient conditions.

### Claim 3 (depends on 1)

The method of claim 1, where Formula I is:
where the quaternary amine composition takes the form of Formula I; where R1 is a carbon bonded to a hydrogen (—CH), R2 is a carbon atom (C—), each R3 is a saturated C6 acyclic hydrocarbyl, R5 is an unsaturated C8 acyclic hydrocarbyl, R6 is an unsaturated C8 acyclic hydrocarbyl, and each R4 is a saturated C2 acyclic hydrocarbyl.

### Claim 4

A method of treating a wellbore, the method comprising the steps of:
introducing an additive-containing well fluid to the wellbore, where the additive-containing well fluid comprises a quaternary amine composition and a well fluid, where the wellbore is defined by a wellbore wall, and where the wellbore is in fluid contact with a hydrocarbon-bearing formation through the wellbore wall;
where the quaternary amine composition comprises Formula I, where Formula I is:
where:
each of R1 and R2 is selected from the group consisting of a carbon atom (C—) and a carbon bonded to a hydrogen (—CH),
each R3 is selected from the group consisting of a saturated aliphatic hydrocarbyl and an unsaturated aliphatic hydrocarbyl,
each R4 is selected from the group consisting of an acyclic hydrocarbyl and an acyclic heterohydrocarbyl,
each of R5 and R6 is selected from the group consisting of a saturated acyclic hydrocarbyl and an unsaturated acyclic hydrocarbyl,
X is selected from the group consisting of an iodine ion (I—), a chlorine ion (Cl—), and combinations of the same; and
treating the wellbore with the additive-containing fluid.

### Claim 5 (depends on 4)

The method of claim 4, where the quaternary amine composition further comprises an additional quaternary amine composition selected from the group consisting of Formula II, Formula III, and combinations of the same, where Formula II is:
where:
each of R7, R8, R9, and R10 is selected from the group consisting of a C— and a —CH,
each of R11, R12, R13, and R14 is selected from the group consisting of a hydrogen atom (H—), an aliphatic hydrocarbyl group, and a substituted aliphatic hydrocarbyl group;
where Formula III is:
R15 is selected from the group consisting of a C—, a —CH, and a carbon bonded to R25 (—CR25),
each of R16, R17, R18, and R19 is selected from the group consisting of a C— and a —CH,
R20 is selected from the group consisting of a C—, a —CH, and a carbon bonded to R26 (—CR26),
each of R21, R22, R23, and R24 can include a hydrogen atom (H—), an aliphatic hydrocarbyl group, and a substituted aliphatic hydrocarbyl group,
R25 is selected from the group consisting of an aliphatic hydrocarbyl group, a substituted aliphatic hydrocarbyl group, and combinations of the same,
R26 is selected from the group consisting of an aliphatic hydrocarbyl group, a substituted aliphatic hydrocarbyl group, and combinations of the same.

### Claim 6 (depends on 4)

The method of claim 4, where the well fluid is selected from the group consisting of an aqueous-based fluid, an oil-based fluid, and combinations of the same.

### Claim 7 (depends on 4)

The method of claim 4, where during the step of treating the wellbore with the additive-containing well fluid at least a portion of the quaternary amine composition is operable to contact a clay material in fluid contact with the wellbore wall.

### Claim 8 (depends on 4)

The method of claim 4, where during the step of treating the wellbore with the additive-containing well fluid at least a portion of the quaternary amine composition is operable to contact an emulsion within the wellbore.

### Claim 9 (depends on 4)

The method of claim 4, where the quaternary amine composition of Formula I is:
such that R1 is a carbon bonded to a hydrogen (—CH), R2 is a carbon atom (C—), each R3 is a saturated C6 acyclic hydrocarbyl, R5 is an unsaturated C8 acyclic hydrocarbyl, R6 is an unsaturated C8 acyclic hydrocarbyl, and each R4 is a saturated C2 acyclic hydrocarbyl.