Synthesis of Renewable Bisphenols from Creosol

Authors

  • Dr. Heather A. Meylemans,

    1. Research Department, Chemistry Division, US Navy, Naval Air Warfare Center Weapons Division (NAWCWD), 1900 N. Knox Rd. Stop 6303, China Lake, CA 93555 (USA), Fax: (+1) 760-939-1617
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  • Dr. Thomas J. Groshens,

    1. Research Department, Chemistry Division, US Navy, Naval Air Warfare Center Weapons Division (NAWCWD), 1900 N. Knox Rd. Stop 6303, China Lake, CA 93555 (USA), Fax: (+1) 760-939-1617
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  • Dr. Benjamin G. Harvey

    Corresponding author
    1. Research Department, Chemistry Division, US Navy, Naval Air Warfare Center Weapons Division (NAWCWD), 1900 N. Knox Rd. Stop 6303, China Lake, CA 93555 (USA), Fax: (+1) 760-939-1617
    • Research Department, Chemistry Division, US Navy, Naval Air Warfare Center Weapons Division (NAWCWD), 1900 N. Knox Rd. Stop 6303, China Lake, CA 93555 (USA), Fax: (+1) 760-939-1617
    Search for more papers by this author

Abstract

A series of renewable bisphenols has been synthesized from creosol (2-methoxy-4-methylphenol) through stoichiometric condensation with short-chain aldehydes. Creosol can be readily produced from lignin, potentially allowing for the large scale synthesis of bisphenol A replacements from abundant waste biomass. The renewable bisphenols were isolated in good yields and purities without resorting to solvent-intense purification methods. Zinc acetate was shown to be a selective catalyst for the ortho-coupling of formaldehyde, but was unreactive when more sterically demanding aldehydes were used. Dilute HCl and HBr solutions were shown to be effective catalysts for the selective coupling of aldehydes in the position meta to the hydroxyl group. The acid solutions could be recycled and reused multiple times without decrease in activity or yield.

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