Non-estrogenic alkylphenol derivatives

Earth boring – well treating – and oil field chemistry – Well treating – Contains organic component

Reexamination Certificate

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C166S263000, C166S270100, C166S275000, C166S305100, C166S372000, C507S203000, C507S252000, C507S253000, C507S261000, C507S262000, C507S267000, C568S028000, C568S031000, C568S035000, C568S608000, C568S609000

Reexamination Certificate

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07977284

ABSTRACT:
A method of making phenol and alkylphenol ethoxylates non-estrogenic by inserting 1 mole of propylene oxide onto the phenolic group before proceeding with the addition of ethylene oxide or mixtures of ethylene and propylene oxide. The final phenolic products can be further reacted to form sulfates, sulfonates, phosphate esters, condensed alkylphenol alkoxylates and other derivatives of alkylphenol or phenol. Non-estrogenic phenol and alkylphenol alkoxylates and their derivatives have been found to be excellent salt tolerant, high temperature stable surfactants for oil recovery from subterranean reservoirs. These products are also useful in forming emulsions of heavy crude for transportation through pipelines.

REFERENCES:
patent: 6736211 (2004-05-01), Berger et al.
patent: 7435709 (2008-10-01), Stonebraker et al.
patent: WO 9706125 (1997-02-01), None
Huntsman Tech Bulletin Jeffsol Alkylene Carbonates Alkoxylation of Phenols and Phenolic Resins, Copyright 2005.
White et al, “environmentally Persistent Alkylphenolic Compounds are Estrogentic”, Endocrinology vol. 135 No. 1 (1994) p. 175-182.
Jobling and Sumpter—“Detergent Components in Sewage Effluent are Weakly Oestrogenic to Fish” Aquatic Toxicology—1993.
Routledge and Sumpter—“Structural Features of Alkylphenolic Chemicals Associated with Estrogenic Activity” Journ. of Biological Chemistry vol. 272, No. 6 p. 3280-3288, (1997).

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