IP Library Granted Patent US 9,422,469
Granted Patent B2
US 9,422,469 · App. 13/833,045 · Granted Aug 23, 2016

Mixed carbon length synthesis of primary guerbet alcohols

Inventors: Varadarjan Dwarakanath (Houston, TX); Robert Shong (Houston, TX)
Assignee: Chevron U.S.A. Inc.
C09K8/584C07C29/34C07C41/03E21B43/16
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Quick Facts
Patent No.
US 9,422,469
App. No.
13/833,045
Granted
Aug 23, 2016
Kind
B2
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 surfactants from a mixture of primary alcohols comprising, receiving a mixture of primary alcohols comprising at least two different chain length primary alcohols and reacting the mixture of primary alcohols to produce a mixture of Guerbet alcohols. The mixture of Guerbet alcohols is then used to produce a surfactant composition comprising surfactants of different molecular weights.

Claims (20)

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 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;

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 surfactant composition from the mixture of greater than two Guerbet alcohols comprises 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 , further comprising injecting the surfactant composition into a subterranean reservoir in an enhanced oil recovery process.

6. 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.

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

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

9. 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.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2013
From: DWARAKANATH, VARADARAJAN; SHONG, ROBERT
To: CHEVRON U.S.A. INC.
Reel/Frame 030485/0150 →
Continuity (1)
Related Publication 20140262282A1 · Sep 18, 2014