Process for preparing and recovering 4,4'-dihydroxy-alpha-alkylstilbene or 4,4'-dihydroxy-alpha, alpha'dialkylstilbene

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United States of America Patent

PATENT NO 5723693
SERIAL NO

08713906

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Abstract

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A process for preparing a 4,4'-dihydroxy-alpha-alkylstilbene or 4,4'-dihydroxy-alpha,alpha'-dialkylstilbene which includes the steps of (A) reacting at a temperature of from -20.degree. C. to 20.degree. C. a mixture of: (1) at least one alpha-haloketone; (2) at least one compound containing one phenolic hydroxyl group or aromatic alkoxy group per molecule such that the mole ratio of phenolic hydroxyl group-containing or aromatic alkoxy group-containing compound(s):alpha-haloketone(s) is at least 0.1:1; and (3) either (a) at least one strong protonic acid or (b) at least one Lewis acid, or (c) any combination thereof; thereby forming a reaction product containing at least one halogen-containing bisphenol compound which, upon being dehydrohalogenated, forms a 4,4'-dihydroxy-alpha-alkylstilbene or 4,4'-dihydroxy-alpha, alpha'-dialkylstilbene; (B) reducing the acid content of the product resulting from step (A) to less than 10,000 ppm; (C) dehydrohalogenating the product obtained from step (B), thereby forming a dehydrohalogenated product containing 4,4'-dihydroxy-alpha-alkylstilbene or 4,4'-dihydroxy-alpha,alpha'-dialkylstilbene; (D) adding water to the product of step (C) in amounts sufficient to crystallize at least a portion of the, 4,4'-dihydroxy-alpha-alkylstilbene or 4,4'-dihydroxy-alpha,alpha'-dialkylstilbene and recovering the crystals and the remaining organic phase separately; (E) independently repeating steps (A), (B), and (C) to obtain a dehydrohalogenated product; (F) mixing at least a portion of organic phase obtained in step (D) with the product obtained in step (E); and (G) adding water to the mixture obtained in step (F) in amounts sufficient to crystallize at least a portion of the 4,4'-dihydroxy-alpha-alkylstilbene or 4,4'-dihydroxy-alpha,alpha'-dialkylstilbene and recovering the crystals.

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Patent Owner(s)

Patent OwnerAddress
MICHIGAN MOLECULAR INSTITUTE1910 WEST SAINT ANDREWS ROAD MIDLAND MI 48640

International Classification(s)

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  • 1996 Application Filing Year
  • C07C Class
  • 1796 Applications Filed
  • 734 Patents Issued To-Date
  • 40.87 % Issued To-Date
Click to zoom InYear of Issuance% of Matters IssuedCumulative IssuancesYearly Issuances19961997199819992000200120022003200420052006200720080255075100

Inventor(s)

Inventor Name Address # of filed Patents Total Citations
Carr, David A Lake Jackson, TX 6 20
Hefner, Jr Robert E Lake Jackson, TX 181 1680

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  • 5 Citation Count
  • C07C Class
  • 17.02 % this patent is cited more than
  • 27 Age
Citation count rangeNumber of patents cited in rangeNumber of patents cited in various citation count ranges33612422548226937313801 - 1011 - 2021 - 3031 - 4041 - 5051 - 6061 - 7071 - 8081 - 9091 - 100100 +010020030040050060070080090010001100120013001400

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