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:

Dzwiniel, Trevor L.; Pupek, Krzysztof

Issue Date:

Tue Feb 11 00:00:00 EST 2020

Research Org.:

Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Org.:

USDOE

OSTI Identifier:

1632539

Patent Number(s):

10556917

Application Number:

16/508,550

Assignee:

UChicago Argonne, LLC (Chicago, IL)

Patent Classifications (CPCs):

B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

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B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY

B01J2231/49 - Esterification or transesterification
B01J31/0245 - {being derivatives of carboxylic or carbonic acids}
B01J31/0251 - {Guanidides
B01J31/0265 - {Phosphazenes, oligomers thereof or the corresponding phosphazenium salts

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

C07F7/00 - Compounds containing elements of Groups 4 or 14 of the Periodic System
C07F7/02 - Silicon compounds
C07F7/08 - Compounds having one or more C—Si linkages
C07F7/0803 - {Compounds with Si-C or Si-Si linkages}
C07F7/081 - {comprising at least one atom selected from the elements N, O, halogen, S, Se or Te}
C07F7/0825 - {Preparations of compounds not comprising Si-Si or Si-cyano linkages}
C07F7/083 - {Syntheses without formation of a Si-C bond}

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DOE Contract Number:  

AC02-06CH11357

Resource Type:

Patent

Resource Relation:

Patent File Date: 07/11/2019

Country of Publication:

United States

Language:

English

Subject:

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 25 ENERGY STORAGE