IP Library Granted Patent US 9,181,283
Granted Patent B2
US 9,181,283 · App. 14/532,250 · Granted Nov 10, 2015

Methods of preparing low molecular weight carbosilanes and precursors thereof

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Quick Facts
Patent No.
US 9,181,283
App. No.
14/532,250
Granted
Nov 10, 2015
Kind
B2
Abstract

A series of silicon compounds are provided, which are excellent precursors to small carbosilanes, such as 1,3,5-trisilapentane, 2,4,6-trisilaheptane, tris(silylmethyl)silane and tetrakis(silylmethyl)silane. A method of preparing a carbosilane involves forming a Grignard, lithium, or metallic reagent from a halomethyltrialkoxysilane, reacting the Grignard, lithium, or metallic reagent with a dihalodihydridosilane, a trihalohydridosilane, a tetrahalosilane, a dialkoxydihydridosilane, a trialkoxyhydridosilane, or a tetraalkoxysilane to yield a carbosilane precursor, and reducing the precursor to form the carbosilane.

Claims (8)

1. A method of preparing a carbosilane comprising: forming a Grignard, lithium, or metallic reagent from a halomethyltrialkoxysilane; reacting the Grignard, lithium, or metallic reagent with a dihalodihydridosilane, a trihalohydridosilane, a tetrahalosilane, a dialkoxydihydridosilane, a trialkoxyhydridosilane, or a tetraalkoxysilane to yield a carbosilane precursor; and reducing the precursor to form the carbosilane;

wherein the carbosilane precursor is a silicon compound having formula (I):

wherein R 1 and R 4 are independently selected from the group consisting of linear alkyl groups having one to about four carbon atoms and linear or branched alkoxy group having one to about eight carbon atoms, R 2 , R 3 , R 5 , and R 6 are each independently selected from the group consisting of branched alkyl groups having about three to about eight carbon atoms, and R 7 and R 8 are independently selected from the group consisting of hydrogen, chlorine, bromine, iodine, linear and branched alkoxy groups having one to about eight carbon atoms, and substituted and unsubstituted linear and branched alkyl groups having one to eight carbon atoms.

2. The method according to claim 1 , wherein the carbosilane is 1,3,5-trisilapentane.

3. The method according to claim 1 , wherein the carbosilane is 2,4,6-trisilaheptane.

4. The method according to claim 1 , wherein the carbosilane is tris(silylmethyl)silane.

5. The method according to claim 1 , wherein the carbosilane is tetrakis(silylmethyl)silane.

6. The method according to claim 1 , wherein the carbosilane is tris(silylmethyl)methylsilane.

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 22, 2024
From: GELEST TECHNOLOGIES, INC.
To: GELEST, INC.
Reel/Frame 068467/0243 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2022
From: GELEST TECHNOLOGIES, INC.
To: GELEST, INC.
Reel/Frame 058668/0350 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 28, 2021
From: GELEST TECHNOLOGIES, INC.
To: GELEST, INC.
Reel/Frame 058595/0701 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 7, 2021
From: GELEST TECHNOLOGIES, INC.
To: GELEST, INC.
Reel/Frame 056272/0183 →
RELEASE OF SECURITY INTEREST Recorded Oct 1, 2020
From: ANTARES CAPITAL LP
To: GELEST BIOSYSTEMS, LLC; GELEST, INC.; GELEST TECHNOLOGIES, INC.
Reel/Frame 053946/0556 →
RELEASE OF SECURITY INTEREST Recorded Jun 24, 2019
From: WELLS FARGO BANK, NATIONAL ASSOCIATION
To: GELEST TECHNOLOGIES, INC.; GELEST, INC.; GELEST BIOSYSTEMS, LLC
Reel/Frame 049567/0194 →
PATENT SECURITY AGREEMENT Recorded Jun 21, 2019
From: GELEST, INC.; GELEST TECHNOLOGIES, INC.; GELEST BIOSYSTEMS, LLC
To: ANTARES CAPITAL LP
Reel/Frame 049557/0526 →
SECURITY INTEREST Recorded Aug 14, 2017
From: GELEST, INC.; GELEST TECHNOLOGIES, INC.; GELEST BIOSYSTEMS, LLC
To: WELLS FARGO BANK, NATIONAL ASSOCIATION
Reel/Frame 043540/0963 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 4, 2014
From: LARSON, GERALD L; PAN, YOULIN; ARKLES, BARRY C
To: GELEST TECHNOLOGIES, INC.
Reel/Frame 034099/0153 →