Environmentally Benign Synthesis of Resorcinol from Glucose

EPA Grant Number: R826116
Title: Environmentally Benign Synthesis of Resorcinol from Glucose
Investigators: Frost, John W.
Institution: Michigan State University
EPA Project Officer: Richards, April
Project Period: November 1, 1997 through October 31, 2000
Project Amount: $337,202
RFA: Technology for a Sustainable Environment (1997) RFA Text |  Recipients Lists
Research Category: Sustainability , Pollution Prevention/Sustainable Development


Resorcinol is a widely used chemical building block globally produced at volumes of 3.0-3.5 x 107 kg/yr. Demand for resorcinol ranges from its formulation with formaldehyde to produce wood adhesives and tackifiers in the manufacture of steel tires to its use in the synthesis of fine chemicals ranging from UV blockers to the active ingredient in Sucrets. New, environmentally benign routes are proposed for the synthesis of resorcinol which share the common feature of employing microbial biocatalysis and use of glucose as a starting material.

Current resorcinol manufacture employs benzene as a starting material. Benzene is carcinogenic, volatile, and is obtained from nonrenewable petroleum feedstocks. All of resorcinol's carbon atoms in the proposed syntheses will be derived from the carbon atoms of glucose. In addition to being nontoxic and nonvolatile, glucose can be derived from the renewable starch and cellulose content of plants cultivated on an enormous scale in the U.S. Resorcinol's oxygen atoms will also be derived from the oxygen atoms of glucose. Use of a starting material which already contains what will become the two oxygen atoms of resorcinol avoids high-temperature fusion with caustic lye, high-salt effluent streams, and explosive intermediates which are associated with chemically forcing oxygen atoms into the aromatic ring of benzene.

By taking advantage of the diversity of aromatic-biosynthesizing pathways and enzymes found in nature, the spectrum of chemicals synthesized by environmentally benign routes from renewable feedstocks can be greatly expanded. Proposed research is distinguished by the fact that polyketide biosynthesis and fatty acid biosynthesis will be the pathways chosen for converting glucose into resorcinol. Previous efforts to replace benzene with glucose as a starting material in chemical manufacture have employed the common pathway of aromatic amino acid biosynthesis (the shikimate pathway) as the biocatalytic route for synthesis of key intermediates or the final chemical product.

The primary objective of the proposed research is to establish the basic route(s) by which resorcinol can be synthesized from glucose. Fatty acid biosynthesis and polyketide biosynthesis will be modified so that triacetic acid lactone (TAL) or 3-hydroxy-5-ketohexanoic acid (HKH) accumulates in microbial culture supernatants. Abiotic, chemical methodology will then be used to catalytically convert the microbially produced TAL or HKH into resorcinol. To create a TAL-synthesizing microbe, fatty acid biosynthesis in Escherichii co!i K-12 will be modified. The gene encoding 6-methylsalicylic acid synthase will also be mutagenized and then expressed in Streptomyces coelicolor A(3)2 to create a TAL- or HKH-synthesizing biocatalyst. For the abiotic, chemical conversion of TAL and HKM into resorcinol, proposed research is to focus on both the ordering of the chemical steps and the reagents needed to catalyze each step.

Supplemental Keywords:

biocatalysis, resorcinol, glucose, benzene, renewable, triacetic acid lactone., RFA, Scientific Discipline, Toxics, Sustainable Industry/Business, Sustainable Environment, Environmental Chemistry, cleaner production/pollution prevention, HAPS, Technology for Sustainable Environment, Economics and Business, triacetic acid lactone, cleaner production, environmentally conscious manufacturing, waste minimization, waste reduction, microbial biocatalysis, green process systems, UV blockers, biosynthesis, Benzene (including benzene from gasoline), pollution prevention, alternative chemical synthesis, environmentally-friendly chemical synthesis, green chemistry

Progress and Final Reports:

Final Report