Method for increasing the hydrogen:carbon ratio of an organic compound

A method for increasing the hydrogen:carbon ratio of an organic compound is disclosed. The organic compound can be one having any of the following functions: hydroxyl, carbonyl, epoxide, acetal, ketal, hemiacetal and hemiketal. The method involves introducing the organic compound and a silicon hydride into a liquid which is either chemically inert or acidic and introducing BF3 into the liquid to produce a reaction product having a higher hydrogen:carbon ratio than the starting organic compound. Examples of organic compound starting materials disclosed include undecanal, benzaldehyde, p-methylbenzaldehyde, p-chlorobenzaldehyde, p-methoxybenzaldehyde, p-cyanobenzaldehyde, p-nitrobenzaldehyde, 2-undecanone, cyclohexanone, 2-methylcyclohexanone, adamantanone, p-cyanoacetophenone, fluorenone, 1-naphthaldehyde, p-nitroacetophenone, fructose and cotton. The use, as the silicon hydride, of triethylsilane, (R)-(+)-1-naphthylphenylmethylsilane, dimethylethylsilane, phenylneopentylmethylsilane, and of tri-n-hexylsilane is disclosed, while methylene chloride is disclosed as the liquid in which the reaction is conducted.
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Abstract/Description: A method for increasing the hydrogen:carbon ratio of an organic compound is disclosed. The organic compound can be one having any of the following functions: hydroxyl, carbonyl, epoxide, acetal, ketal, hemiacetal and hemiketal. The method involves introducing the organic compound and a silicon hydride into a liquid which is either chemically inert or acidic and introducing BF3 into the liquid to produce a reaction product having a higher hydrogen:carbon ratio than the starting organic compound. Examples of organic compound starting materials disclosed include undecanal, benzaldehyde, p-methylbenzaldehyde, p-chlorobenzaldehyde, p-methoxybenzaldehyde, p-cyanobenzaldehyde, p-nitrobenzaldehyde, 2-undecanone, cyclohexanone, 2-methylcyclohexanone, adamantanone, p-cyanoacetophenone, fluorenone, 1-naphthaldehyde, p-nitroacetophenone, fructose and cotton. The use, as the silicon hydride, of triethylsilane, (R)-(+)-1-naphthylphenylmethylsilane, dimethylethylsilane, phenylneopentylmethylsilane, and of tri-n-hexylsilane is disclosed, while methylene chloride is disclosed as the liquid in which the reaction is conducted.
Subject(s): 558/423
558/411
568/648
568/705
568/814
568/835
568/881
568/907
568/939
570/201
585/469
585/638
Date Issued: 1978-12-19
Title: Method for increasing the hydrogen:carbon ratio of an organic compound.
Name(s): The University of Toledo, assignee
Fry, James L., inventor
Type of Resource: text
Genre: patent
Publisher: United States Patent and Trademark Office
Other Date: Date Filed: 1977-08-01
Date Issued: 1978-12-19
Physical Form: application/pdf
Extent: 5 p.
Abstract/Description: A method for increasing the hydrogen:carbon ratio of an organic compound is disclosed. The organic compound can be one having any of the following functions: hydroxyl, carbonyl, epoxide, acetal, ketal, hemiacetal and hemiketal. The method involves introducing the organic compound and a silicon hydride into a liquid which is either chemically inert or acidic and introducing BF3 into the liquid to produce a reaction product having a higher hydrogen:carbon ratio than the starting organic compound. Examples of organic compound starting materials disclosed include undecanal, benzaldehyde, p-methylbenzaldehyde, p-chlorobenzaldehyde, p-methoxybenzaldehyde, p-cyanobenzaldehyde, p-nitrobenzaldehyde, 2-undecanone, cyclohexanone, 2-methylcyclohexanone, adamantanone, p-cyanoacetophenone, fluorenone, 1-naphthaldehyde, p-nitroacetophenone, fructose and cotton. The use, as the silicon hydride, of triethylsilane, (R)-(+)-1-naphthylphenylmethylsilane, dimethylethylsilane, phenylneopentylmethylsilane, and of tri-n-hexylsilane is disclosed, while methylene chloride is disclosed as the liquid in which the reaction is conducted.
Identifier(s): utpatents-US4130574 (IID)
Patent No.: US4130574 (patno)
Appl. No.: 05/820734 (appno)
Subject(s): 558/423
558/411
568/648
568/705
568/814
568/835
568/881
568/907
568/939
570/201
585/469
585/638
Held by: United States Patent and Trademark Office (USPTO) Public Search Facility
Location: University of Toledo Digital Repository
Rights Statement: No Copyright - United States
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