US 9,517,987 B1 · Renewable bisphenols and resins from salicylic acid

Abstract

A method for the selective synthesis of bisphenols, thermosetting resins, and thermoplastics from salicylic acid, the major component of wintergreen oil, and a viable target for engineered biosynthesis. Condensation of salicylic acid, structural analogs of salicylic acid, and derivatives of salicylic acid with short chain aldehydes or ketones and subsequent decarboxylation has the potential to produce bisphenols that are direct replacements for conventional resins, while the steric and electronic effects of salicylic acid improve the efficiency and selectivity of the conversion process. The utilization of renewable polyphenols as precursors to epoxies, poly carbonates, and high temperature thermosets including cyanate esters, provides an opportunity to develop full-performance resins while reducing the use of petroleum based feedstocks. This approach will then diminish the overall environmental impact of resin production while allowing for a sustainable source of phenols.

Claims17

Dependent claims

A method for synthesizing polyphenol compounds from a renewable, ortho-substituted phenol source, comprising:

a) condensing a carbonyl reactant with said renewable ortho-substituted phenol utilizing at least one acid catalyst to form a polyphenol;
said renewable ortho-substituted phenol having the formula:
where each R″ is independently selected from alkyl, cycloalkyl, arene, alkoxy, and OH;
each R3 is independently selected from hydrogen, alkyl, cycloalkyl, arene, or alkoxy;
x is 0 to 3;
y is 0 to 4;
x+y is 1 to 5;
and,
where one of said x+y substituent groups is ortho to the hydroxy group on said phenol, and
said carbonyl reactant having the formula:
where R and R′ are each independently selected from the group consisting of hydrogen, an aliphatic group or an aromatic group or are mutually part of a ring system;
b) where y is greater than zero, modifying said polyphenols by reducing said (C02R3) groups to either hydrogen or a methyl group.

9 more elements

Dependencies are inferred from the claim text.

Renewable bisphenols and resins from salicylic acid

Life of this patent

Renewable bisphenols and resins from salicylic acid

Life of this patent

Abstract

Claims17