# US 11,299,665 B2 · Olefinic ester compositions and their use in stimulating hydrocarbon production from a subterranean formation

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- Number: US 11,299,665 B2
- Document ID: US11299665B2
- Status: Granted
- Kind: B2
- Application number: 16/108,288
- Filed: 2018-08-22
- Published: 2019-01-31
- Granted: 2022-04-12
- Earliest claimed: 2014-01-16
- Assignees: Wilmar Trading Pte. Ltd.
- Applicants: Wilmar Trading Pte. Ltd.
- Inventors: Frederyk Ngantung; Robin Weitkamp
- Web page: https://patentgrep.com/patent/US11299665B2

## CPC

- C09K 8/602: {containing surfactants}
- C09K 8/524: organic depositions, e.g. paraffins or asphaltenes
- C09K 8/86: containing organic compounds
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

Compositions for stimulating hydrocarbon production from a subterranean formation are generally disclosed. In some embodiments, such compositions include olefinic ester compounds, such as alkyl esters of C10-18 unsaturated fatty acids. In some embodiments, the olefinic ester compounds are derived from a natural oil or a natural oil derivative, for example, by catalytic olefin metathesis. Uses of such compounds, such as in oil- and gas-production methods are also generally disclosed.

## Claims

### Claim 1

A method of stimulating an oil or gas well, comprising:
providing a composition comprising olefinic ester compounds, wherein the olefinic ester compounds comprise methyl 9-decenoate, methyl 9-undenenoate, methyl 9-dodecenoate, or mixtures thereof, wherein the composition is an oil-in-water emulsion, and wherein the dispersed phase comprises the olefinic ester compounds and the continuous phase comprises water, wherein the olefinic ester compounds make up at least 50 percent by weight of the dispersed phase; and
introducing the composition into an oil or gas well.

### Claim 2 (depends on 1)

The method of claim 1, wherein the oil or gas well is a gas well for shale gas or tight gas.

### Claim 3 (depends on 1)

The method of claim 1, wherein the introducing comprises injecting the composition into the oil or gas well under pressure.

### Claim 4 (depends on 1)

The method of claim 1, wherein the composition further comprises a surfactant.

### Claim 5 (depends on 1)

The method of claim 1, wherein the composition further comprises a terpene.

### Claim 6 (depends on 5)

The method of claim 5, wherein the terpene is selected from the group consisting of linacool, geraniol, nopol, α-terpineol, β-terpineol, γ-terpineol, 4-terpineol, menthol, eucapyptol, menthone, d-limonene, terpinolene, α-ocimene, β-ocimene, α-terpinene, β-terpinene, γ-terpinene, δ-terpinene, α-pinene, β-pinene, citronellene, turpentine, and any combinations thereof.

### Claim 7 (depends on 6)

The method of claim 6, wherein the terpene is d-limonene.

### Claim 8 (depends on 1)

The method of claim 1, wherein the composition further comprises C1-6 alkanolic esters of C10-18 saturated fatty acids.