Mixed carbon length synthesis of primary guerbet alcohols

Patent metadata

Field	Value
Publication number	US-9617464-B2
Application number	US-201615340747-A
Country	US
Kind code	B2
Filing date	Nov 1, 2016
Priority date	Sep 15, 2011
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

Abstract

In an embodiment of the disclosure, mixtures of different carbon length alcohols are used as the primary feedstock for Guerbet alcohols. Specifically, embodiments relate to a method of synthesizing mixed molecular weight additives from a mixture of primary alcohols comprising, receiving a mixture of primary alcohols having greater than two different chain length primary alcohols and reacting the mixture of primary alcohols in a single reactor to produce a mixture of at least five Guerbet alcohols. The mixture of Guerbet alcohols can then be used to produce an additive or surfactant composition comprising additives or surfactants of different molecular weights.

First claim

What is claimed is:

1. A method of synthesizing mixed chain length surfactants from a mixture of primary alcohols, the method comprising:
receiving a mixture of primary alcohols comprising greater than two different chain length primary alcohols in equal parts of each primary alcohol;
reacting in a single reactor the mixture of primary alcohols to produce a mixture of at least five Guerbet alcohols having different molecular weights wherein:
i. the number of Guerbet alcohols produced is equal to twice the number of primary alcohols minus one;
ii. the mixture of at least five Guerbet alcohols comprises a lowest molecular weight Guerbet alcohol, a highest molecular weight Guerbet alcohol, a Guerbet alcohol having a molecular weight halfway between the molecular weight of the lowest molecular weight Guerbet alcohol and the highest molecular weight Guerbet alcohol;
iii. the Guerbet alcohol having the molecular weight halfway between the molecular weight of the lowest molecular weight Guerbet alcohol and the highest molecular weight Guerbet alcohol has a highest concentration of the Guerbet alcohols in the mixture of at least five Guerbet alcohols;
iv. the lowest molecular weight Guerbet alcohol and the highest molecular weight Guerbet alcohol each have a lowest concentration of the Guerbet alcohols in the mixture of at least five Guerbet alcohols; and
v. remaining Guerbet alcohols in the mixture of at least five Guerbet alcohols have concentrations increasing as molecular weight approaches the molecular weight halfway between the molecular weight of the lowest molecular weight Guerbet alcohol and the highest molecular weight Guerbet alcohol and decreasing as molecular weight approaches the lowest and the highest molecular weight Guerbet alcohols; and

producing a surfactant composition from the mixture of greater than two Guerbet alcohols;
wherein the reacting the mixture of primary alcohols to produce the mixture of greater than two Guerbet alcohols is stopped when a Guerbet alcohol conversion of at least 80% is obtained; and
wherein unreacted primary alcohols are removed from the mixture of greater than two Guerbet alcohols.

2. The method of claim 1 , wherein the producing the surfactant from the mixture of greater than two Guerbet alcohols comprises forming an alkoxylated Guerbet alcohol by reacting a lower weight epoxide with a Guerbet alcohol alkoxylate.

3. The method of claim 1 , wherein the producing the surfactant composition from the mixture of greater than two Guerbet alcohols comprises forming a Guerbet sulfate by sulfation of a Guerbet alcohol alkoxylate.

4. The method of claim 1 , wherein the producing the surfactant composition from the mixture of greater than two Guerbet alcohol comprises forming a Guerbet sulfonate by sulfonation of a Guerbet alcohol alkoxylate.

5. The method of claim 1 , wherein the mixture of primary alcohols is derived from a natural source selected from the group consisting of palm oil, algal oil, canola oil, castor bean oil, coconut oil, corn oil, cotton oil, fish oil, flaxseed oil, hempseed oil, jatropha oil, lard, mustard seed oil, nut oil, olive oil, palm kernel oil, peanut oil, rapeseed oil, safflower seed oil, soybean oil, sunflower oil, tall oil, tallow, yellow grease, and any oil produced by using the following: bacteria, yeast, fungi, unicellular organisms, multicellular organisms or a combination thereof.

6. The method of claim 1 , further comprising injecting the surfactant composition into a subterranean reservoir in an enhanced oil recovery process.

7. The method of claim 1 , wherein the mixture of primary alcohols comprises three primary alcohols, four primary alcohols, five primary alcohols, six primary alcohols or seven primary alcohols.

8. The method of claim 1 , wherein the mixture of primary alcohols comprises greater than two different primary alcohols in equal ratios.

9. The method of claim 1 , wherein the mixture of primary alcohols comprises greater than two different primary alcohols in different ratios.

10. The method of claim 1 , wherein the producing the surfactant composition from the mixture of greater than two Guerbet alcohols comprises forming a Guerbet carboxylate by carboxylation of a Guerbet alcohol.

Assignees

• Chevron Usa Inc

Inventors

• Dwarakanath Varadarajan
• Shong Robert G
• Winslow Gregory A
• Thach Sophany

Classifications

• C09K8/58

  Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids · CPC title

• C09K8/588

  characterised by the use of specific polymers {(polymeric surfactants C09K8/584)} · CPC title

• C09K8/584 Primary

  characterised by the use of specific surfactants · CPC title

• C07C29/60

  by elimination of -OH groups, e.g. by dehydration (C07C29/34 takes precedence) · CPC title

• E21B43/16

  Enhanced recovery methods for obtaining hydrocarbons · CPC title