Waste-free process for manufacture of amides and amines from...

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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C564S490000, C564S493000

Reexamination Certificate

active

06476270

ABSTRACT:

BACKGROUND
This invention relates generally to a process for conversion of carbonium ion precursors and nitrites to amines.
U.S. Pat. No. 2,457,660 discloses a process for preparation of N-tertiary alkyl amides from carbonium ion precursors and nitrites in the presence of an acidic catalyst. The list of suitable acidic catalysts includes ammonium bisulfate. This reference does not disclose a process for conversion of the amides to the corresponding amines.
The problem addressed by this invention is to reduce the need for a strong acid catalyst in a process for conversion of carbonium ion precursors and nitriles to amines.
STATEMENT OF INVENTION
In one embodiment, the present invention is a method for preparation of an amine from a carbonium ion precursor and a nitrile. The method comprises the steps of: (a) contacting the carbonium ion precursor and the nitrile with aqueous ammonium hydrogen sulfate to produce an amide; and (b) hydrolyzing the amide to the amine.
In another embodiment, the present invention is directed to a substantially waste-free method for preparation of an amide from a carbonium ion precursor and a nitrile. The method comprises the steps of (a) contacting the carbonium ion precursor and the nitrile with aqueous ammonium hydrogen sulfate to produce an amide; (b) recovering diammonium sulfate from an aqueous phase; and (c) decomposing diammonium sulfate by heating to produce ammonia and ammonium hydrogen sulfate.


REFERENCES:
patent: 2457660 (1948-12-01), Gresham et al.
patent: 2601387 (1952-06-01), Gresham et al.
patent: 0099752 (1984-02-01), None
patent: 902342 (1945-08-01), None
Luzgin, Mikhail and Alexander G. Stepanov., “The Ritter reaction in zeolite H-ZSM-5. NMR observation if the intermediate N-alkylnitrilium cation formed on interaction between ButOH and MeCN”, Medeleev Commun., pp. 238-239 (1996).
Firouzabadi et al., “Highly Selective Admiration of Benzylic Alcohols With Nitriles. A Modified Ritter Reaction.”, Synthetic Communications, 24(5) pp. 601-607 (1994).
Olah et al., “Nafion-HRCatalized Baeyer-Villiger Oxidation and Ritter Reaction (1)”, Materials Chemistry and Physics, 17, pp. 21-30 (1987).

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