Process for preparing polyoxyalkylene glycol ethers using alkoxylated alkylphenol-aldehyde resins as demulsifiers

Abstract

The invention provides a process for preparing polyoxyalkylene glycol monoethers and/or diethers by reacting an alkoxide with an alkylating agent, which comprises adding water and a compound of the formula 1

Description

EXAMPLES

Example 1: (Comparative)

Preparation of polypropylene glycol allyl butyl ether without breaker addition

In a stirred reactor with temperature and pressure monitoring, 96.4 g of a polypropylene glycol allyl ether having a mean molar mass of 1400 g/mol are admixed with 6.43 g of sodium hydroxide at 80° C. with stirring under nitrogen. Subsequently, 19.28 g of butyl chloride are added dropwise within one hour. The reactor is heated to 120° C. for postreaction and stirred at this temperature for another three hours. Subsequently, excess butyl chloride is distilled off and cooled to 90° C. With stirring, exactly the amount of water required to bring the amount of sodium chloride into solution is added.

Example 2

Preparation of polypropylene glycol allyl butyl ether with breaker addition

The procedure is as described in Example 1, with the difference that 50 ppm of a crude oil splitter of the formula 1 (alkoxylated alkylphenol-formaldehyde resin) are added to the aqueous phase separation.

Example 3 (Comparative)

Preparation of polyalkylene glycol allyl butyl ether without breaker addition

In a stirred reactor with temperature and pressure monitoring, 96.5 g of a polyalkylene glycol allyl ether having a mean molar mass of 1600 g/mol and a mixing ratio of ethylene glycol to propylene glycol of 3 to 1 are admixed with 3.7 g of sodium hydroxide at 80° C. with stirring under nitrogen. Subsequently, 11.6 g of butyl chloride are slowly added dropwise. The reactor is heated to 120° C. for postreaction and stirred at this temperature for three hours. Subsequently, excess butyl chloride is distilled off and the mixture is cooled to 90° C. With stirring, exactly the amount of water required to bring the amount of sodium chloride into solution is added.

Example 4

Preparation of polyalkylene glycol allyl butyl ether with breaker addition

The procedure is as described in Example 3, with the difference that 50 ppm of a crude oil splitter of the formula 1 (alkoxylated alkylphenol-formaldehyde resin) are added to the aqueous phase separation.

Example 5 (Comparative)

Preparation of polyalkylene glycol allyl methyl ether without breaker addition

In a stirred reactor with temperature and pressure monitoring, 99.6 g of a polyalkylene glycol allyl ether having a mean molar mass of 2000 g/mol and a mixing ratio of ethylene glycol to propylene glycol of 1 to 1 are admixed with 0.75 g of sodium hydroxide at 80° C. with stirring under nitrogen. Subsequently, 0.95 g of methyl chloride is slowly added dropwise. The reactor is heated to 120° C. for postreaction and stirred at this temperature for a further three hours. Thereafter, excess butyl chloride is distilled off and the mixture is cooled to 90° C. With stirring, the amount of water required to bring the amount of sodium chloride into solution is added.

Example 6

Preparation of polyalkylene glycol allyl methyl ether with breaker addition

The procedure is as described in Example 5, with the difference that 50 ppm of a crude oil splitter of the formula 1 (alkoxylated alkylphenol-formaldehyde resin) are added to the aqueous phase separation.

Results of the phase separation experiments:

To determine the effectiveness of the emulsion breaker, the water separation from the crude product emulsion was determined as a function of time. To this end, in each case 100 ml of the crude product emulsion were introduced into breakage bottles (conical, screw-closeable, graduated glass vessels). Thereafter, the breakage bottles were placed into a temperature-controlled bath and the water separation was monitored at 80° C.

	TABLE 1
	Water separation [ml] per unit time
Ex.	10 min	30 min	60 min	2 h	3 h	4 h	5 h	6 h	12 h	24 h
1	0	0	0	2	4	6.5	9	11.5	16.5	complete
2	4	8	10	13	16	17.5	complete
3	0	0	0	0	1	1	2.5	4	7	12.5
4	1	2	4.5	8.5	12	13.5	16.5	complete
5	0	0	0	0	0	0	0	1	3	4.5
6	0	3	5.5	8	12	14.5	complete

Claims

1. A process for preparing a polyoxyalkylene glycol monoether or a polyoxyalkylene glycol diether or a mixture thereof, said process comprising reacting a mixture of an alkoxide and an alkylating agent, said reacting comprising adding to said mixture water and a compound of formula 1

2. The process as claimed in claim 1, in which the polyoxyalkylene glycol monoether or polyoxyalkylene glycol diether or mixture thereof corresponds to formula 2 R—O-(AO)y—R1   (2)

3. The process as claimed in claim 2, in which y is from 2 to 100.

4. The process of claim 2, in which R is a group selected from the group consisting of an alkyl having from 1 to 24 carbon atoms,an alkenyl having from 2 to 24 carbon atoms,a formula R*—C(O)— where R* is a hydrocarbon group having from 1 to 24 carbon atoms,a phenyl, a benzyl, and an allyl group.

5. The process of claim 2, in which R comprises from 4 to 12 carbon atoms.

6. The process of claim 2, in which R1 is a group selected from the group consisting of an alkyl having from 1 to 12 carbon atoms, an alkenyl having from 2 to 12 carbon atoms, a phenyl, a benzyl, and an allyl group groups.

7. The process of claim 2, in which R1 comprises from 2 to 8 carbon atoms.

8. The process of claim 2, in which AO comprises at least one propoxy or butoxy group.

9. The process of claim 1, in which R2 is a C4-C12-alkyl radical.

10. The process of claim 1, in which p is from 2 to 40.

11. The process of claim 1, in which k is from 5 to 150.

12. The process of claim 1, further comprising adding to the mixture at least one codemulsifier is selected from the group consisting of a) an alkylene oxide block polymer based on alcohols, polyols, amines and amino alcoholsb) an crosslinked alkylene oxide block polymer of type a)c) an alkoxylated crosslinked alkylene oxide block polymer of type b)d) an alkoxylated polyethyleneimine, and mixtures thereof.