Water solubilization of DDGS via derivatization with phosphite esters

Bioresour Technol. 2008 Aug;99(12):5193-205. doi: 10.1016/j.biortech.2007.09.036. Epub 2007 Dec 11.

Abstract

Ethanol production from corn starch in the corn dry milling process leaves Distillers' Dry Grains and Solubles (DDGS) as a major by-product from which additional ethanol may be economically obtained from its glucan content. A challenge in processing the cellulose content of this material lies in its extensive inter-cellulose chain hydrogen bonding, which inhibits access of enzymes capable of cleaving glycosidic bonds, a transformation required for providing fermentable sugars. The phosphitylation of cellulosic OH groups using a reactive bicyclic phosphite ester is utilized to disrupt cellulosic hydrogen bonds, thus providing access to cellulose chains for further processing. We describe a method of pretreating DDGS with commercially available trimethylolpropane phosphite [P(OCH2)3CEt] in the presence of a slight molar excess of water to afford greater than 90% DDGS solubility in the reaction mixture in methanol and in water. Preliminary results using a model compound [D-(+)-permethylated cellobiose] indicate that glycosidic bonds are cleaved as a consequence of this pretreatment.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Cellulose / chemistry
  • Esters / chemistry
  • Esters / metabolism*
  • Hydrolysis
  • Industrial Waste*
  • Isomerism
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Phosphites / chemistry
  • Phosphites / metabolism*
  • Solubility
  • Solvents
  • Water / metabolism*
  • Zea mays / metabolism*

Substances

  • Esters
  • Industrial Waste
  • Phosphites
  • Solvents
  • Water
  • Cellulose