The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Apr. 09, 2019

Filed:

Apr. 11, 2013
Applicant:

The United States of America As Represented BY the Secretary of the Navy, Washington, DC (US);

Inventors:

Benjamin G. Harvey, Ridgecrest, CA (US);

Heather A. Meylemans, Ridgecrest, CA (US);

Attorney:
Primary Examiner:
Int. Cl.
CPC ...
C04B 26/12 (2006.01); C07C 41/30 (2006.01); C07C 261/02 (2006.01); C07C 41/18 (2006.01); C07C 43/205 (2006.01); C07C 43/23 (2006.01); C08G 64/16 (2006.01); C08G 73/06 (2006.01);
U.S. Cl.
CPC ...
C07C 41/30 (2013.01); C07C 41/18 (2013.01); C07C 43/2055 (2013.01); C07C 43/23 (2013.01); C07C 261/02 (2013.01); C08G 64/1608 (2013.01); C08G 73/0644 (2013.01); C08G 73/0655 (2013.01);
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 yield and purity without resorting to solvent intense purification methods. Zinc acetate was shown to be selective catalyst for ortho-coupling of formaldehyde but was unreactive with more sterically demanding aldehydes. Dilute HCl and HBr solutions were shown to be effective catalysts for the selective coupling of aldehydes in the position meta to the phenol. Acid solutions could be recycled and used multiple times without decreases in activity or yield.


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