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Title: Method for preparing bis-(silylalkyl)carbonate esters

Abstract

Carbonate esters of Formula (I): (R1)(R2)(R3)Si—R4—O—C(═O)—O—R4—Si(R1)(R2)(R3) are prepared by reaction of a silyl-substituted alcohol of Formula (II): (R1)(R2)(R3)Si—R4—OH with an activated carbonyl compound of Formula (III): C(═O)Z2 in the presence of a catalyst (e.g., an bicyclic amidine, a bicyclic guanidine, or a phosphazene) in an aprotic solvent. In Formulas (I) and (II) each of R1 and R2 independently is alkyl; R3 is alkyl or —X1—Si(R5)(R6)(R7); X1 is O or alkylene; R4 is alkylene; and each R5, R6, and R7 independently is alkyl. In Formula (III), Z is 1-N-imidazolyl or 1-N-succinimidyl. In some embodiments, the catalyst used in the methods described herein comprises at least one base selected from the group consisting of a bicyclic amidine and a bicyclic guanidine. The reaction proceeds readily under both bulk and continuous flow reactor conditions.

Inventors:
;
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1632539
Patent Number(s):
10,556,917
Application Number:
16/508,550
Assignee:
UChicago Argonne, LLC (Chicago, IL)
DOE Contract Number:  
AC02-06CH11357
Resource Type:
Patent
Resource Relation:
Patent File Date: 07/11/2019
Country of Publication:
United States
Language:
English

Citation Formats

Dzwiniel, Trevor L., and Pupek, Krzysztof. Method for preparing bis-(silylalkyl)carbonate esters. United States: N. p., 2020. Web.
Dzwiniel, Trevor L., & Pupek, Krzysztof. Method for preparing bis-(silylalkyl)carbonate esters. United States.
Dzwiniel, Trevor L., and Pupek, Krzysztof. Tue . "Method for preparing bis-(silylalkyl)carbonate esters". United States. https://www.osti.gov/servlets/purl/1632539.
@article{osti_1632539,
title = {Method for preparing bis-(silylalkyl)carbonate esters},
author = {Dzwiniel, Trevor L. and Pupek, Krzysztof},
abstractNote = {Carbonate esters of Formula (I): (R1)(R2)(R3)Si—R4—O—C(═O)—O—R4—Si(R1)(R2)(R3) are prepared by reaction of a silyl-substituted alcohol of Formula (II): (R1)(R2)(R3)Si—R4—OH with an activated carbonyl compound of Formula (III): C(═O)Z2 in the presence of a catalyst (e.g., an bicyclic amidine, a bicyclic guanidine, or a phosphazene) in an aprotic solvent. In Formulas (I) and (II) each of R1 and R2 independently is alkyl; R3 is alkyl or —X1—Si(R5)(R6)(R7); X1 is O or alkylene; R4 is alkylene; and each R5, R6, and R7 independently is alkyl. In Formula (III), Z is 1-N-imidazolyl or 1-N-succinimidyl. In some embodiments, the catalyst used in the methods described herein comprises at least one base selected from the group consisting of a bicyclic amidine and a bicyclic guanidine. The reaction proceeds readily under both bulk and continuous flow reactor conditions.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2020},
month = {2}
}

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