Process for producing n-alkyl-dinitroalkylanilines
AssigneeSRM Chemical, Ltd. Co.
InventorsStefan Kwiatkowski, Krzysztof Pupek, Brenda L. Lawrence, Lowell J. Lawrence
Life of this patent
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Abstract
This invention relates to a process for producing N-alkyl-dinitroalkylaniline and particularly N-sec-butyl-4-tert-butyl-2,6-dinitroaniline by methylation of an alkylphenol followed by nitration of the resulting alkylanisole which is followed by reaction with an amine.
Claims19
A process for producing N-sec-butyl-4-tert-butyl-2,6-dinitroaniline, comprising:
- reacting 4-tert-butylphenol with dimethyl sulfate to produce 4-tert-butylanisole;
- reacting 4-tert-butylanisole with nitric acid to produce 4-tert-butyl-2,6-dinitroanisole;
- and
- reacting 4-tert-butyl-2,6-dinitroanisole with sec-butylamine to produce N-sec-butyl-4-tert-butyl-2,6-dinitroaniline.
A process for producing N-sec-butyl-4-tert-butyl-2,6-dinitroaniline, comprising:
- reacting 4-tert-butylphenol with a halide free methylating agent to produce a first reaction intermediate;
- reacting said first reaction intermediate with a nitrating agent to produce a second reaction intermediate;
- and
- reacting said second reaction intermediate with sec-butylamine to produce N-sec-butyl-4-tert-butyl-2,6-dinitroaniline.
A process for producing N-sec-butyl-4-tert-butyl-2,6-dinitroaniline, comprising:
- reacting 4-tert-butylanisole with a nitrating agent to produce a reaction intermediate;
- and
- reacting said reaction intermediate with sec-butylamine to produce N-sec-butyl-4-tert-butyl-2,6-dinitroaniline.
A process for producing an N-alkyl-dinitroalkylaniline comprising:
- reacting an alkylphenol with a methylating agent to produce an alkylantsole intermediate;
- reacting the alkylanisole intermediate with a nitrating agent to produce a dinitro-substituted alkylanisole intermediate;
- reacting the dinitro-substituted alkylanisole intermediate with an amine to produce an N-alkyl-dinitroalkylaniline.
A process for producing N-alkyl-dinitroalkylaniline, comprising:
- reacting an alkylphenol of a formula:
- ##STR5## wherein R=an alkyl group with one to ten carbon atoms, CF.sub.3, CH.sub.3 SO.sub.2 -- or H.sub.2 NSO.sub.2 --;
- R.sup.1 =--H or --CH.sub.3 ;
- with a halide-free methylating agent to produce a first reaction intermediate;
- reacting said first reaction intermediate with a nitrating agent to produce a second reaction intermediate;
- reacting said second reaction intermediate with an amine selected from a group including sec-butylamine and 1-ethylpropylamine to produce N-alkyl-dinitroalkylaniline.
A process for producing N-alkyl-dinitroalkylaniline, comprising:
- reacting an alkyl anisole with a nitrating agent selected from a group consisting of nitric acid, acetyl nitrate, a mixture of nitric acid and acetic anhydride and mixtures thereof to produce a reaction intermediate;
- and
- reacting said reaction intermediate with an amine selected from a group consisting of sec-butylamine and 1-ethylpropylamine to produce N-alkyl-dinitroalkylaniline.
A process for producing N-sec-butyl-4-tert-butyl-2,6-dinitroaniline, comprising:
- reacting 4-tert-butylphenol with dimethyl sulfate to produce 4-tert-butylanisole;
- reacting 4-tert-butylanisole with nitric acid and acetic anhydride to produce 4-tert-butyl-2,6-dinitroanisole;
- reacting 4-tert-butyl-2,6-dinitroanisole with sec-butylamine to produce N-sec-butyl-4-tert-butyl-2,6-dinitroaniline;
- and
- reacting the acetic acid by-product produced during the process with ketene to produce acetic anhydride for use in subsequent processing.
Dependencies are inferred from the claim text.