# US 2020/0399520 A1 · Additives for oil and gas drilling and production

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2020/0399520 A1
- Document ID: US20200399520A1
- Status: Published application
- Kind: A1
- Application number: 17/010,683
- 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/US20200399520A1

## 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 quaternary amine composition, the quaternary amine composition comprises Formula III, where Formula III is:
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 R7 and R10 is selected from the group consisting of a C— and a —CH,
each of R11 and R14 is selected from the group consisting of a hydrogen atom (H—), an aliphatic hydrocarbyl group, and a substituted aliphatic hydrocarbyl group;
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,
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 quaternary amine composition of claim 1, where R3 is selected from the group consisting of a saturated C2-C20 acyclic hydrocarbyl and an unsaturated C2-C20 acyclic hydrocarbyl.

### Claim 3 (depends on 1)

The quaternary amine composition of claim 1, where R3 is a saturated C5-C10 acyclic hydrocarbyl.

### Claim 4 (depends on 1)

The quaternary amine composition of claim 1, where the composition comprises Formula III, where a double ring formed by R1, R2, R7, R15, R16, R17, R18, R19, R20, and R10 is selected from the group consisting of a decahydronapthalene, a tetralin, a dialin, a naphthalene, and other bicyclic compounds.

### Claim 5 (depends on 1)

The quaternary amine composition of claim 1, where Formula III is selected from the group consisting of Formula IX, Formula X, Formula XI, Formula XII, Formula XIII, Formula XIV, Formula XV, Formula XVI, Formula XVII, Formula XVIII, Formula XIX, and Formula XX where the compositions of Formulas IX-Formula XX are:

### Claim 6 (depends on 1)

The quaternary amine composition of claim 1, where the substituted aliphatic hydrocarbyl group comprises a replacement group, where the replacement group is selected from the group consisting of a hydroxyl group, an aminoalkyl group, an alkoxyl group, an alkylthio group, an amino group, a halo group, a haloalkyl group, a silyl group, a phosphoryl group, a sulfonyl group, and combinations of the same.

### Claim 7 (depends on 1)

The quaternary amine composition of claim 1, further comprising an additional quaternary amine composition selected from the group consisting of Formula I, Formula II, and combinations of the same, where Formula I:
where Formula I is:
where:
each of R5 and R6 is selected from the group consisting of a saturated acyclic hydrocarbyl and an unsaturated acyclic hydrocarbyl,
where Formula II is:
where:
each of R8 and R9 is selected from the group consisting of a C— and a —CH, and
each of R12 and R13 is selected from the group consisting of a hydrogen atom (H—), an aliphatic hydrocarbyl group, and a substituted aliphatic hydrocarbyl group.

### Claim 8

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 III, where Formula III is:
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 R7 and R10 is selected from the group consisting of a C— and a —CH,
each of R11 and R14 is selected from the group consisting of a hydrogen atom (H—), an aliphatic hydrocarbyl group, and a substituted aliphatic hydrocarbyl group;
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,
X is selected from the group consisting of an iodine ion (I—), a chlorine ion (Cl—), and combinations of the same.

### Claim 9 (depends on 8)

The method of claim 8, where the step of reacting the alkoxylated dimer diamine with the methyl halogen is at ambient conditions.

### Claim 10 (depends on 8)

The method of claim 8, where a double ring formed by R1, R2, R7, R15, R16, R17, R18, R19, R20, and R10 is selected from the group consisting of a decahydronapthalene, a tetralin, a dialin, a naphthalene, and other bicyclic compounds.

### Claim 11 (depends on 8)

The method of claim 8, where Formula III is selected from the group consisting of Formula IX, Formula X, Formula XI, Formula XII, Formula XIII, Formula XIV, Formula XV, Formula XVI, Formula XVII, Formula XVIII, Formula XIX, and Formula XX where the compositions of Formulas IX-Formula XX are:

### Claim 12

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 where Formula III is:
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 R7 and R10 is selected from the group consisting of a C— and a —CH,
each of R11 and R14 is selected from the group consisting of a hydrogen atom (H—), an aliphatic hydrocarbyl group, and a substituted aliphatic hydrocarbyl group;
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,
X is selected from the group consisting of an iodine ion (I—), a chlorine ion (Cl—), and combinations of the same.

### Claim 13 (depends on 12)

The method of claim 12, 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 14 (depends on 12)

The method of claim 12, 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 15 (depends on 12)

The method of claim 12, 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 metal material positioned within the wellbore.

### Claim 16 (depends on 12)

The method of claim 12, 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.