Process for the preparation of azo compounds from amino compound

Details Process for the preparation of azo compounds from amino compound Process for the preparation of azo compounds from amino compound

1978-09-25

1981-06-09

Higel, Floyd D.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07C10700, C07C10702, C07C10704

Patent

active

042724350

ABSTRACT:
Azo compounds of the formula, ##STR1## wherein each of R.sub.1 and R.sub.2 is selected from the group consisting of (1) C.sub.1 -C.sub.8 aliphatic hydrocarbons unsubstituted or substituted with carboxyl, hydroxyl or alkoxy of the formula --OR.sub.4 in which R.sub.4 is a C.sub.1 -C.sub.4 aliphatic hydrocarbon, (2) C.sub.3 -C.sub.8 alicyclic hydrocarbons, (3) C.sub.6 -C.sub.10 aromatic hydrocarbons and (4) C.sub.4 -C.sub.12 alicyclic hydrocarbons formed by combining R.sub.1 and R.sub.2 together with the adjacent carbon atom, and R.sub.3 is selected from the group consisting of nitrile, esters of the formula --COOR.sub.4 in which R.sub.4 is a C.sub.1 -C.sub.4 aliphatic hydrocarbon, a carboxylate of the formula --COOM in which M is an alkali metal or alkaline earth metal, and a carboxylamido, which are useful as foaming agents or radical polymerization initiator, are prepared in a high yield by reacting a corresponding amino compound with a metal hypohalite or with an alkyl hypohalite in the presence of an alkali, using a phase transfer catalyst in a heterogeneous medium comprising water and organic solvent, the phase transfer catalyst being one member selected from the group consisting of organic quaternary ammonium salts, organic quaternary phosphonium salts and macrocyclic polyethers.

REFERENCES:
patent: 2515628 (1950-07-01), Castle
patent: 2711405 (1955-06-01), Anderson
patent: 2713576 (1955-07-01), Anderson
patent: 3775395 (1973-11-01), Koyanagi et al.
patent: 3783148 (1974-01-01), Fuchs
patent: 3937696 (1976-02-01), Knowles et al.
patent: 4028345 (1977-06-01), Moore
patent: 4051124 (1977-09-01), Moore
patent: 4061590 (1977-12-01), Moore
Weber et al., "Phase Transfer Catalysis in Organic Synthesis", vol. 4, pp. 3 to 7, (1977).

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