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Title: Methods for the synthesis of deuterated vinyl pyridine monomers

Abstract

Methods for synthesizing deuterated vinylpyridine compounds of the Formula (1), wherein the method includes: (i) deuterating an acyl pyridine of the Formula (2) in the presence of a metal catalyst and D.sub.2O, wherein the metal catalyst is active for hydrogen exchange in water, to produce a deuterated acyl compound of Formula (3); (ii) reducing the compound of Formula (3) with a deuterated reducing agent to convert the acyl group to an alcohol group, and (iii) dehydrating the compound produced in step (ii) with a dehydrating agent to afford the vinylpyridine compound of Formula (1). The resulting deuterated vinylpyridine compounds are also described.

Inventors:
; ;
Issue Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1125020
Patent Number(s):
8658802
Application Number:
13/553,293
Assignee:
UT-Battelle, LLC (Oak Ridge, TN)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
DOE Contract Number:  
AC05-00OR22725
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Hong, Kunlun, Yang, Jun, and Bonnesen, Peter V. Methods for the synthesis of deuterated vinyl pyridine monomers. United States: N. p., 2014. Web.
Hong, Kunlun, Yang, Jun, & Bonnesen, Peter V. Methods for the synthesis of deuterated vinyl pyridine monomers. United States.
Hong, Kunlun, Yang, Jun, and Bonnesen, Peter V. Tue . "Methods for the synthesis of deuterated vinyl pyridine monomers". United States. https://www.osti.gov/servlets/purl/1125020.
@article{osti_1125020,
title = {Methods for the synthesis of deuterated vinyl pyridine monomers},
author = {Hong, Kunlun and Yang, Jun and Bonnesen, Peter V},
abstractNote = {Methods for synthesizing deuterated vinylpyridine compounds of the Formula (1), wherein the method includes: (i) deuterating an acyl pyridine of the Formula (2) in the presence of a metal catalyst and D.sub.2O, wherein the metal catalyst is active for hydrogen exchange in water, to produce a deuterated acyl compound of Formula (3); (ii) reducing the compound of Formula (3) with a deuterated reducing agent to convert the acyl group to an alcohol group, and (iii) dehydrating the compound produced in step (ii) with a dehydrating agent to afford the vinylpyridine compound of Formula (1). The resulting deuterated vinylpyridine compounds are also described.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2014},
month = {2}
}

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Works referenced in this record:

Stereoregularity of poly(2-vinylpyridine) determined by 1H-NMR and 13C-NMR spectroscopy
journal, June 1976


Stereoregularity of poly(2-vinylpyridine) and poly-(4-vinylpyridine)
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NMR spectra of poly-2-vinylpyridine
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General method of obtaining deuterium-labeled heterocyclic compounds using neutral D2O with heterogeneous Pd/C
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Efficient and Selective Pt/C-Catalyzed H–D Exchange Reaction of Aromatic Rings
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Hydrogen/Deuterium Exchange Reactions of Olefins with Deuterium Oxide Mediated by the Carbonylchlorohydrido- tris(triphenylphosphine)ruthenium(II) Complex
journal, May 2010


Solvent-free reduction of aldehydes and ketones using solid acid-activated sodium borohydride
journal, August 2006


Oligomerization stereochemistry of vinyl monomers. IV. Ion-pair structure and β-carbon stereochemistry in anionic oligomerization of 2-vinylpyridine
journal, October 1978


1H-NMR spectra of epimerized polymers derived from isotactic poly(β,β-dideuterio-2-vinylpyridine)
journal, February 1993