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Title: Method and reaction pathway for selectively oxidizing organic compounds

Abstract

A method of selectively oxidizing an organic compound in a single vessel comprises: a) combining an organic compound, an acid solution in which the organic compound is soluble, a compound containing two oxygen atoms bonded to one another, and a metal ion reducing agent capable of reducing one of such oxygen atoms, and thereby forming a mixture; b) reducing the compound containing the two oxygen atoms by reducing one of such oxygen atoms with the metal ion reducing agent to, 1) oxidize the metal ion reducing agent to a higher valence state, and 2) produce an oxygen containing intermediate capable of oxidizing the organic compound; c) reacting the oxygen containing intermediate with the organic compound to oxidize the organic compound into an oxidized organic intermediate, the oxidized organic intermediate having an oxidized carbon atom; d) reacting the oxidized organic intermediate with the acid counter ion and higher valence state metal ion to bond the acid counter ion to the oxidized carbon atom and thereby produce a quantity of an ester incorporating the organic intermediate and acid counter ion; and e) reacting the oxidized organic intermediate with the higher valence state metal ion and water to produce a quantity of alcoholmore » which is less than the quantity of ester, the acid counter ion incorporated in the ester rendering the carbon atom bonded to the counter ion less reactive with the oxygen containing intermediate in the mixture than is the alcohol with the oxygen containing intermediate.« less

Inventors:
 [1];  [1]
  1. (Richland, WA)
Issue Date:
Research Org.:
BATTELLE MEMORIAL INSTITUTE
OSTI Identifier:
871743
Patent Number(s):
5786505
Assignee:
Battelle Memorial Institute (Richland, WA) PNNL
DOE Contract Number:  
AC06-76RL01830
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
method; reaction; pathway; selectively; oxidizing; organic; compounds; compound; single; vessel; comprises; combining; acid; solution; soluble; containing; oxygen; atoms; bonded; metal; reducing; agent; capable; forming; mixture; oxidize; valence; produce; intermediate; reacting; oxidized; carbon; atom; counter; bond; quantity; ester; incorporating; water; alcohol; incorporated; rendering; reactive; compound containing; vessel comprises; oxygen containing; organic compound; acid solution; organic compounds; reducing agent; carbon atom; oxygen atoms; agent capable; selectively oxidizing; atom bonded; single vessel; oxidized carbon; oxidizing organic; oxygen atom; reaction pathway; /999/

Citation Formats

Camaioni, Donald M., and Lilga, Michael A. Method and reaction pathway for selectively oxidizing organic compounds. United States: N. p., 1998. Web.
Camaioni, Donald M., & Lilga, Michael A. Method and reaction pathway for selectively oxidizing organic compounds. United States.
Camaioni, Donald M., and Lilga, Michael A. Thu . "Method and reaction pathway for selectively oxidizing organic compounds". United States. https://www.osti.gov/servlets/purl/871743.
@article{osti_871743,
title = {Method and reaction pathway for selectively oxidizing organic compounds},
author = {Camaioni, Donald M. and Lilga, Michael A.},
abstractNote = {A method of selectively oxidizing an organic compound in a single vessel comprises: a) combining an organic compound, an acid solution in which the organic compound is soluble, a compound containing two oxygen atoms bonded to one another, and a metal ion reducing agent capable of reducing one of such oxygen atoms, and thereby forming a mixture; b) reducing the compound containing the two oxygen atoms by reducing one of such oxygen atoms with the metal ion reducing agent to, 1) oxidize the metal ion reducing agent to a higher valence state, and 2) produce an oxygen containing intermediate capable of oxidizing the organic compound; c) reacting the oxygen containing intermediate with the organic compound to oxidize the organic compound into an oxidized organic intermediate, the oxidized organic intermediate having an oxidized carbon atom; d) reacting the oxidized organic intermediate with the acid counter ion and higher valence state metal ion to bond the acid counter ion to the oxidized carbon atom and thereby produce a quantity of an ester incorporating the organic intermediate and acid counter ion; and e) reacting the oxidized organic intermediate with the higher valence state metal ion and water to produce a quantity of alcohol which is less than the quantity of ester, the acid counter ion incorporated in the ester rendering the carbon atom bonded to the counter ion less reactive with the oxygen containing intermediate in the mixture than is the alcohol with the oxygen containing intermediate.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1998},
month = {1}
}

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