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## wherein: R.sub.1 and R.sub.2 form, together with the carbon atom to which R.sub.1 and R.sub.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.sub.1CH(OH)R.sub.2 (II) and at least one dimetallic cyanide catalyst, wherein R.sub.1 and R.sub.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.

Description

EXAMPLES

(1) 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

(2) 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.

(3) 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)

(4) 441 g (4.32 M) of MI BC 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.

(5) 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

(6) 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.

(7) 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.

(8) 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-60E-4P0 are recovered. OHN=86 mg of KOH/g and coloration of 44 Hz.