Secondary alcohol phosphate ester

Abstract

The invention relates to a compound of following formula (I), and also to the addition salts thereof with an organic or mineral base, the solvates such as hydrates and the mixtures thereof; to the use thereof as a surfactant, wetting agent, detergent, emulsifier, dispersant, corrosion inhibitor, plasticizer, sequestering agent, ionic liquid, stabilizer, lubricant, bitumen additive, gelling agent in oils, flotation collector for ores, adjuvant in the manufacture of plastic objects, anti-static agent, additive for fertiliser coverings and for enhanced oil recovery, and also to the compositions comprising at least one compound of formula (I) and/or a salt thereof, alone or as a mixture. ##STR00001##

Claims

1. A salt of a compound of formula (I) below: ##STR00007## 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 selected from a 2-octyl radical and a 4-methyl-2-pentyl radical; 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; G denotes the group —O—[B].sub.p—R.sub.5; R.sub.5 represents a group chosen from a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group, comprising from 1 to 30 carbon atoms; B represents a sequence of one or more units chosen from ethylene oxide, propylene oxide and butylene oxide units, and mixtures thereof; p denotes an integer ranging from 0 to 100; J denotes the group —O-[E].sub.s-R.sub.6, R.sub.6 represents a group chosen from a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group, comprising from 1 to 30 carbon atoms; E represents a sequence of one or more units chosen from ethylene oxide, propylene oxide and butylene oxide units, and mixtures thereof; s denotes an integer ranging from 0 to 100; m denotes an integer ranging from 1 to 3; and q and r denote integers ranging from 0 to 2, where m+q+r=3, wherein the compound is in ammonium salt form or in organic amine salt form, the organic amine being chosen from alkylamines, alkyldiamines, cycloalkylamines, alkylamido(poly)amines, aromatic amines and alkanolamines, the amine optionally being primary, secondary or tertiary, and also optionally being alkoxylated, and also from heterocyclic amines, urea, and mixtures thereof.

2. The salt as claimed in claim 1, wherein n is between, limits inclusive, 1 and 75.

3. The salt as claimed in claim 1, wherein p and s, independently of each other, are between, limits inclusive, 0 and 75.

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

5. A salt of a compound of forumla (I) below: ##STR00008## 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 selected from a 2-octyl radical and a 4-methyl-2-pentyl radical; 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; G denotes the group —O—[B].sub.p—R.sub.5; R.sub.5 represents a group chosen from a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group, comprising from 1 to 30 carbon atoms; B represents a sequence of one or more units chosen from ethylene oxide, propylene oxide and butylene oxide units, and mixtures thereof; p denotes an integer ranging from 0 to 100; J denotes the group —O-[E]s-R.sub.6, R.sub.6 represents a group chosen from a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group, comprising from 1 to 30 carbon atoms; E represents a sequence of one or more units chosen from ethylene oxide, propylene oxide and butylene oxide units, and mixtures thereof; s denotes an integer ranging from 0 to 100; m denotes an integer ranging from 1 to 3; and q and r denote integers ranging from 0 to 2, where m+q+r=3, wherein the compound is in the form of an inorganic salt chosen from the elements from column 1 of the Periodic Table of the Elements; the elements from column 2 of the Periodic Table of the Elements, the elements from columns 3 to 12 of the Periodic Table of the Elements, the elements from column 13 of the Periodic Table of the Elements, and mixtures thereof.

6. The salt as claimed in claim 5, wherein n is between, limits inclusive, 1 and 75.

7. The salt as claimed in claim 5, wherein p and s, independently of each other, are between, limits inclusive, 0 and 75.

8. A composition comprising at least one salt of a compound of formula (I) as defined in claim 5, with one or more aqueous, organic or aqueous-organic solvents, and optionally 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: Synthesis of a Propoxylated Phosphate Ester of 2-octanol

(2) Step 1a: Propoxylation of 2-octanol

(3) 591 g (4.54 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 0.225 MPa at 27° C.

(4) The reaction medium is brought to 90° C. with stirring, and the temperature is then increased to 120° C. At this temperature of 120° C., 40 g of propylene oxide are introduced. When initiation of the reaction is observed, the rest of the propylene oxide is introduced, i.e. 792 g (13.62 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 propylene oxide is then stripped out with nitrogen. The reactor is cooled to 60° C. and 1381 g of alkoxylated 2-octanol comprising 3 propylene oxide units are withdrawn.

(5) Step 1b: Phosphatation of Propoxylated 2-octanol

(6) Method a): Phosphatation With Phosphorus Pentoxide

(7) 456 g (1.50 M) of propoxylated 2-octanol obtained previously are placed in a 1 L reactor, under a nitrogen atmosphere. The reactor is heated to 60° C. 71 g (0.5 M) of phosphorus pentoxide are then added. The addition of the phosphorus pentoxide is performed while taking care to ensure that the temperature does not exceed 80° C. At the end of the addition, the temperature of the reactor is maintained at 80° C. for 3 hours with stirring. At the end of the reaction, the reactor is cooled to a temperature of 60° C. and the product is isolated.

(8) 521 g of alkoxylated phosphate ester of 2-octanol comprising 3 propylene oxide units are recovered.

(9) The reaction is represented schematically below:

(10) ##STR00004##
Method b): Phosphatation With Polyphosphoric Acid

(11) 186 g (0.61 M) of propoxylated 2-octanol containing 3 PO are placed in a 1 L reactor, under a nitrogen atmosphere. The reactor is heated to 50° C. and 67.6 g (0.2 M) of polyphosphoric acid (115% equivalent H.sub.3PO.sub.4) are then added dropwise. The reactor is heated to a temperature of 60° C., with stirring.

(12) The reaction is monitored by determination of the acid number. The reaction is considered to be complete when the values no longer change. The reactor is then cooled to 40° C.

(13) 240 g of alkoxylated phosphate ester of 2-octanol comprising 3 propylene oxide units are recovered.

(14) The reaction is represented schematically below:

(15) ##STR00005##
Method c): Phosphatation With Phosphoryl Trichloride

(16) 456 g (1.50 M) of propoxylated 2-octanol obtained previously are placed in a 1 L reactor, under a nitrogen atmosphere. The reactor is heated to 70° C. and 76.5 g (0.50 M) of anhydrous phosphoryl trichloride are then added dropwise. The reactor is then heated to a temperature of 90° C., with stirring.

(17) The hydrochloric acid is removed continuously by sparging nitrogen into the reaction medium. The reaction is monitored by means of the amount of hydrochloric acid produced. The reaction is considered to be complete when no more HCl is evolved. The reactor is then cooled to 60° C.

(18) 470 g of alkoxylated 2-octanol phosphate comprising 3 propylene oxide units are recovered.

(19) The reaction is represented schematically below:

(20) ##STR00006##

Example 2: Ethoxylated Phosphate Ester of 2-octanol

(21) Step 2.a: Ethoxylation of 2-octanol

(22) 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.

(23) 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 withdrawn. (OHN: 210 mg of KOH/g and coloration of 26 Hz).

(24) Step 2.b: Phosphatation of Ethoxylated 2-octanol

(25) The phosphatation reaction is repeated with phosphorus pentoxide as described in example 1, step 1 b, method a), but with the product obtained in step 2a above.

Example 3: Salification with a Metal

(26) 465 g (1 M) of the ethoxylated 2-octanol phosphate obtained in example 2 as described previously are placed in a 1 L reactor. The reactor is heated to 125° C. 81 g (1 M) of zinc oxide are then added. The addition of the zinc oxide is performed with stirring. At the end of the addition, the temperature of the reactor is maintained at 125° C. for 2 hours with stirring. At the end, the reactor is cooled to a temperature of 60° C. and the product is isolated.

(27) About 540 g of the zinc salt of the alkoxylated phosphate ester of 2-octanol comprising 3 ethylene oxide units are recovered.

Example 4: Salification With a Fatty Amine

(28) 465 g (1 M) of the ethoxylated 2-octanol phosphate obtained in example 2 as described previously are placed in a 1 L reactor. The reactor is heated to 80° C. 259 g (1 M) of a fatty amine bearing a chain of about 18 carbon atoms, sold by Arkema France under the name Noram SH®, are then added with stirring while taking care to ensure that the temperature does not exceed 80° C. At the end of the addition, the temperature of the reactor is maintained at 80° C. for 15 minutes with stirring. At the end, the reactor is cooled and recovered.

(29) About 720 g of the fatty amine salt of the alkoxylated phosphate ester of 2-octanol comprising 3 ethylene oxide units are recovered.