Process for the regiospecific sulfonation of sulfonyl substitute

Details Process for the regiospecific sulfonation of sulfonyl substitute Process for the regiospecific sulfonation of sulfonyl substitute

1986-11-24

1992-01-21

Lee, Mary C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Sulfate esters

558 61, 534629, 534642, C07C30512, C07C31316

Patent

active

050829637

ABSTRACT:
A process for the preparation of isomerically pure sulfonic acids of 2-aminonaphthalenes having a fiber reactive substituent of the formula --(SO.sub.2 X) wherein X is --CH.sub.2 --CH.sub.2 --Z and Z is a substituent such as thiosulfato, phosphato or sulfato. The process comprises a first step of acylating the amino group of the substituted 2-aminonaphthalene to form a N-acyl derivative of the formula, R--CO--NH--A--SO.sub.2 X wherein A represents a naphthalene nucleus. The N-acyl derivative is then sulfonated to provide an essentially isomerically pure sulfonic acid derivative of the formula R--CO--NH--A(--SO.sub.2 X, --SO.sub.3 H). Depending upon the position of the --SO.sub.2 X group in the starting material, the sulfonation reaction product will have one of the following isomeric ring positions for the sulfonyl and sulfo groups, respectively; 5:7 or 7:5 or 6:8 or 8:6. Exemplary products are 2-acetylamino-5-(beta-sulfatoethylsulfonyl)-naphthalene-7-sulfonic acid or 2-acetylamino-7-(beta-sulfatoethylsulfonyl)-naphthalene-5-sulfonic acid or 2-acetylamino-6-(beta-sulfatoethylsulfonyl)-naphthalene-8-sulfonic acid or 2-acetylamino-8-(beta-sulfatoethylsulfonyl)-naphthalene-6-sulfonic acid. The latter aminonaphthalene sulfonic acid having 2-8-6 substitution is an important starting material for the preparation of fiber reactive dyes; the former three are not. New monoazo and disazo dyes or their metal complexes may be prepared from the 2,6,8; 2,5,7; and 2,7,5 isomers by diacylating, diazotizing and coupling them with coupling components selected from an unsubstituted or substituted benzene, naphthylene, acetoacetic acid arylide, arylamide, pyazolone or pyridone.

REFERENCES:
patent: 2657205 (1953-10-01), Heyna et al.
patent: 4045428 (1977-08-01), Meininger et al.
patent: 4046754 (1977-09-01), Meininger et al.
patent: 4110365 (1978-08-01), Bildstein et al.
patent: 4118184 (1978-10-01), Opitz et al.
patent: 4252529 (1981-02-01), Steuernagel
patent: 4334076 (1982-06-01), Steuernagel et al.
patent: 4379937 (1983-04-01), Corso et al.
patent: 4492654 (1985-01-01), Hoyer et al.
patent: 4600542 (1986-07-01), Lindner et al.
Cerfontain, "Mechanistic Aspects in Aromatic Sulfonation and Desulfonation", pp. 1 to 45 (1968).

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