IP Library Granted Patent US 11,485,695
Granted Patent B2
US 11,485,695 · App. 16/760,564 · Granted Nov 1, 2022

Alkoxylated secondary alcohol

Inventors: Jean-Philippe Gillet (Brignais, FR); Thierry Beillon (Sainte Foy les Lyon, FR)
Assignee: Arkema France
C07C43/13C07C41/03C08G65/2609C08G65/2663
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Quick Facts
Patent No.
US 11,485,695
App. No.
16/760,564
Granted
Nov 1, 2022
Kind
B2
Abstract

The invention relates to a compound of following formula (I): a preparation process, uses thereof and compositions containing the same, wherein R 1 and R 2 , represent, independently of one another, a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group comprising from 1 to 6 carbon atoms, where the sum of the carbon atoms of the groups R 1 and R 2 ranges from 2 to 7, and where R 1 and R 2 may also form, together and with the carbon atom bearing them, a 6-, 7-, or 8-membered ring; n is an integer of between 1 and 100, limits included; A represents a sequence of one or more units chosen from ethylene oxide, propylene oxide, butylene oxide units and mixtures thereof; the group formed by R 1 , R 2 and the carbon atom to which R 1 and R 2 are attached has a degree of branching equal to 0, 1 or 2.

Claims (28)

1. A compound of formula (I) below:

wherein:

R 1 and R 2 form, together with the carbon atom to which R 1 and R 2 are attached, a 2-octyl radical;

n is an integer between, limits inclusive, 1 and 100; and

A represents a sequence of one or more units selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide units, and mixtures thereof.

2. A process for preparing a compound of formula (I) as defined in claim 1 , comprising the following successive steps:

mixing in a reactor at least one secondary alcohol of formula (II) below:

R 1 CH(OH)R 2 (II)

and at least one dimetallic cyanide catalyst, wherein R 1 and R 2 are as defined in claim 1 and where the secondary alcohol was previously dried to contain to less than 200 ppm of water,

gradually adding to the mixture n ethylene oxide(s), where n is an integer between, limits inclusive, 1 and 100;

maintaining reaction temperature until reaction pressure has stabilized;

removing any residual ethylene oxide from the reactor;

adding one or more oxides selected from the group consisting of ethylene oxide, propylene oxide and butylene oxide, and mixtures thereof;

maintaining reaction temperature until reaction pressure has stabilized; and

recovering the compound of formula (I) after optional removal of any residual ethylene oxide, propylene oxide, butylene oxide and mixtures thereof.

3. The process as claimed in claim 2 , wherein the dimetallic cyanide catalyst is zinc hexacyanocobaltate.

4. The process as claimed in claim 2 , wherein the content of the dimetallic cyanide catalyst ranges from 1 to 1000 ppm relative to the content of the secondary alcohol of formula (II).

5. The process as claimed in claim 2 , wherein the ethylene oxide/secondary alcohol of formula (II) mole ratio ranges from 2 to 100.

6. A method for alkoxylating 2-octanol comprising:

mixing in a reactor 2-octanol and at least one dimetallic cyanide catalyst, where the 2-octanol was previously dried to contain to less than 200 ppm of water,

gradually adding to the mixture n ethylene oxide(s), where n is an integer between, limits inclusive, 1 and 100;

maintaining reaction temperature until reaction pressure has stabilized;

removing any residual ethylene oxide from the reactor;

adding one or more oxides selected from the group consisting of ethylene oxide, propylene oxide and butylene oxide, and mixtures thereof;

maintaining reaction temperature until reaction pressure has stabilized; and

recovering the alkoxylate octanol after optional removal of any residual ethylene oxide, propylene oxide, butylene oxide and mixtures thereof.

7. A nonionic surfactant, low-foaming surfactant, wetting agent, foaming agent, hydrotrope, detergent, solvent, reactive solvent, coalescer, compatibilizer, emulsifying agent, dispersant, chemical intermediary, corrosion inhibitor, demulcent, plasticizer, sequestrant, mineral deposition inhibitor, ionic liquid, stabilizer, lubricant, bitumen additive, deinking additive, oil gellant, ore flotation collector, processing aid, antistatic agent or fertilizer coating additive comprising the compound of formula (I) as defined in claim 1 .

8. A composition comprising at least one compound of formula (I) as defined in claim 1 , and one or more aqueous, organic or aqueous-organic solvents, optionally with one or more additives and fillers.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 5, 2020
From: GILLET, JEAN-PHILIPPE; BEILLON, THIERRY
To: ARKEMA FRANCE
Reel/Frame 052569/0531 →