ALKOXYLATED SECONDARY ALCOHOL

Abstract

The invention relates to a compound of following formula (I):

##STR00001##

a preparation process, uses thereof and compositions containing the same, wherein R.sub.1 and R.sub.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.sub.1 and R.sub.2 ranges from 2 to 7, and where R.sub.1 and R.sub.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.sub.1, R.sub.2 and the carbon atom to which R.sub.1 and R.sub.2 are attached has a degree of branching equal to 0, 1 or 2.

Claims

1. A compound of formula (I) below: ##STR00003## in which: the groups R.sub.1 and R.sub.2, which may be identical or different, represent, independently of each other, 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.sub.1 and R.sub.2 ranges from 2 to 7, and where the groups R.sub.1 and R.sub.2 may also form, together with the carbon atom that bears them, a 6 or 7- or membered ring; n is an integer between, limits inclusive, 1 and 100; A represents a sequence of one or more units chosen from ethylene oxide, propylene oxide and butylene oxide units, and mixtures thereof; and the group formed by R.sub.1, R.sub.2 and the carbon atom to which R.sub.1 and R.sub.2 are attached has a degree of branching equal to 0, 1 or 2.

2. The compound as claimed in claim 1, wherein the group formed by R.sub.1, R.sub.2 and the carbon atom to which R.sub.1 and R.sub.2 are attached has a degree of branching of 1 or 2.

3. The compound as claimed in claim 1, wherein the group formed by R.sub.1, R.sub.2 and the carbon atom to which R.sub.1 and R.sub.2 are attached is a 4-methyl-2-pentyl radical.

4. A process for preparing a compound of formula (I) as defined in claim 1, comprising the following successive steps: (a) reacting a secondary alcohol of formula (II) below:
R.sub.1CH(OH)R.sub.2  (II), in which R.sub.1 and R.sub.2 are as defined in claim 1, with n ethylene oxide(s), where n is as defined in claim 1, in the presence of at least one catalyst of dimetallic cyanide type; and (b) reacting the product obtained from step (a) with one or more oxides chosen from ethylene oxide, propylene oxide and butylene oxide, and mixtures thereof, in the presence of at least one catalyst of dimetallic cyanide type.

5. The process as claimed in claim 4, wherein the secondary alcohol of formula (II) has a weight-average molar mass ranging from 70 to 200 g/mol.

6. The process as claimed in claim 4, wherein the secondary alcohol of formula (II) is methylisobutylcarbinol.

7. The process as claimed in a claim 4, wherein the catalyst of dimetallic cyanide type is zinc hexacyanocobaltate.

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

9. The process as claimed in a claim 4, wherein the ethylene oxide/secondary alcohol of formula (II) mole ratio ranges from 2 to 100.

10. (canceled)

11. The compound of formula (I) as defined in claim 1, where the compound is one or more of 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, sequestrants, mineral deposition inhibitor, ionic liquid, stabilizer, lubricant, bitumen additive, deinking additive, oil gellant, ore flotation collector, processing aid in manufacturing plastics, antistatic agent, and fertilizer coating additive.

12. 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.

Description

EXAMPLES

[0066] The 2-octanol (CAS RN 123-96-6) used is the “refined” grade 2-octanol Oleris® (purity>99%), sold by Arkema France.

Example 1: Ethoxylation of 2-Octanol

[0067] 619 g (4.76 M) of 2-octanol dried to less than 200 ppm of water and 0.06 g (100 ppm) of catalyst DMC Arcol® are placed in a clean, dry 4 L autoclave. The reactor is closed and purged with nitrogen and the leaktightness under pressure is checked. The reactor is pressurized with nitrogen to 0.269 MPa at 20° C.

[0068] The reaction medium is brought to 120° C. with stirring. At this temperature of 120° C., 40 g of ethylene oxide are introduced. When initiation of the reaction is observed, the rest of the ethylene oxide is introduced, i.e. 628 g (14.27 M) in total over 60 minutes at a temperature of 140° C.-150° C. At the end of the addition, the temperature is maintained for 30 minutes and the residual ethylene oxide is then stripped out with nitrogen. The reactor is cooled to 60° C. and 1240 g of alkoxylated 2-octanol comprising 3 ethylene oxide units are recovered. The hydroxyl number (OHN) is 210 mg of KOH/g and the coloration is 26 Hz.

Example 2: Ethoxylation of Methylisobutylcarbinol (MIBC)

[0069] 441 g (4.32 M) of MIBC dried to less than 200 ppm of water and 0.044 g (100 ppm) of catalyst DMC Arcol® are placed in a clean, dry 4 L autoclave. The reactor is closed and purged with nitrogen and the leaktightness under pressure is checked. The reactor is pressurized with nitrogen to 0.246 MPa at 28° C.

[0070] The reaction medium is brought to 120° C. with stirring. At this temperature of 120° C., 40 g of ethylene oxide are introduced. When initiation of the reaction is observed at 141° C., the rest of the ethylene oxide is introduced, i.e. 380 g (8.64 M) in total over 40 minutes at a temperature of 140° C.-150° C. At the end of the addition, the temperature is maintained for 60 minutes and the residual ethylene oxide is then stripped out with nitrogen. The reactor is cooled to 60° C. and 815 g of alkoxylated methylisobutylcarbinol comprising 2 ethylene oxide units are recovered. (OHN): 290 mg of KOH/g and coloration: 3 Hz).

Example 3: Ethoxylation-Propoxylation of 2-Octanol

[0071] 1034 g (7.95 M) of 2-octanol dried to less than 200 ppm of water and 0.15 g (145 ppm) of catalyst DMC Arcol® are placed in a clean, dry 10 L autoclave. The reactor is closed and purged with nitrogen and the leaktightness under pressure is checked. The reactor is pressurized with nitrogen to 0.12 MPa at 27° C.

[0072] The reaction medium is brought to 120° C. with stirring. At this temperature of 120° C., 35 g of ethylene oxide are introduced. When initiation of the reaction is observed, the rest of the ethylene oxide is introduced, i.e. 2098 g (47.68 M) in total over 4 hours at a temperature of 140° C.-150° C. At the end of the addition, the temperature is maintained for 30 minutes to consume the residual ethylene oxide. A sample of the intermediate product withdrawn for analysis indicates the following features: OHN=136 mg of KOH/g and coloration of 39 Hz.

[0073] The reaction is continued by introducing propylene oxide, i.e. 1844 g (31.18 M) in total over 3 hours. At the end of the reaction, the temperature is maintained at 140° C. for 30 minutes to consume the residual propylene oxide, the system is then purged and degassed, and 4910 g of 2-octanol-6OE-4PO are recovered. OHN=86 mg of KOH/g and coloration of 44 Hz.