GB457518A - Process for the manufacture of 2.4-dinitro-3:6-dihalogenanilines - Google Patents

Process for the manufacture of 2.4-dinitro-3:6-dihalogenanilines

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Publication number
GB457518A
GB457518A GB31295/35A GB3129535A GB457518A GB 457518 A GB457518 A GB 457518A GB 31295/35 A GB31295/35 A GB 31295/35A GB 3129535 A GB3129535 A GB 3129535A GB 457518 A GB457518 A GB 457518A
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United Kingdom
Prior art keywords
dinitro
sulphuric acid
specific gravity
dichloraniline
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB31295/35A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sandoz AG
Original Assignee
Sandoz AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB457518A publication Critical patent/GB457518A/en
Expired legal-status Critical Current

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Abstract

2 : 4-Dinitro-3 : 6-dihalogenanilines are prepared (1) by treating 3 : 6-dihalogen-4-nitranilines with nitric acid of specific gravity about 1,54, or (2) by treating 3 : 6-dihalogen-N-alkylsulphonylanilines with nitric acid of specific gravity not below about 1,4 in the absence of sulphuric acid, and subsequently removing the alkylsulphonyl group by hydrolysis, or (3) by treating 3 : 6-dihalogen-N-arylsulphonyl group by hydrolysis, Process (1) may be effected in the presence or absence of sulphuric acid; if sulphuric acid is present the 2 : 4-dinitro-3 : 6-dihalogenaniline is obtained directly, but if sulphuric acid is absent the 3 : 6-dihalogen-4-nitrophenylnitramine is first obtained, and is then converted into the 2 : 4-dinitro-3 : 6-dihalogenaniline by treatment with sulphuric acid. The products are useful as diazo components in the manufacture of azo dyes. In the examples, (1) 3 : 6-dichloro 4-nitraniline is treated with sulphuric acid monohydrate and nitric acid of specific gravity 1,54; 2 : 4-dinitro-3 : 6-dichloraniline is obtained; (2) 2 : 4 - dinitro - 3 : 6 - dibromaniline is obtained similarly from 3 : 6-dibromo-4-nitraniline; (3) 3 : 6-dichloro-4-nitraniline is treated with nitric acid of specific gravity 1,54, and the 3 : 6-dichloro-4-nitrophenylnitramine so obtained is treated with sulphuric acid, this yielding 2 : 4-dinitro-3 : 6-dichloraniline; (4) N-methanesulphonyl-3 : 6-dichloraniline is boiled with nitric acid of specific gravity 1,4 to yield N-methanesulphonyl - 2 : 4 - dinitro - 3 : 6-dichloraniline, which is then warmed with sulphuric acid to split off the methanesulphonyl group; (5) N-p-toluenesulphonyl-3 : 6-dichloraniline is treated with nitric acid of specific gravity 1,54 to yield N-(3<1>-nitro-4<1>-methylbenzenesulphonyl)-3 : 6-dichlor-2 : 4-dinitraniline, which is then warmed with sulphuric acid to split off the arylsulphonyl group; 3 - nitro - 4 - methylbenzenesulphonic acid is obtained as a by-product. The Specification as open to inspection under Sect. 91 states that the 2 : 4-dinitro-3 : 6-dihalogenanilines may be prepared by nitrating N-alkylsulphonyl- or N-arylsulphonyl-4-nitro-3 : 6-dihalogenanilines, and includes an example in which N-p-toluenesulphonyl-4-nitro-3 : 6-dichloraniline is treated with nitric acid of specific gravity 1,52 to yield an initial product identical with that of example 5 above, which is then hydrolyzed as described in that example. This subject-matter does not appear in the Specification as accepted.
GB31295/35A 1934-11-24 1935-11-12 Process for the manufacture of 2.4-dinitro-3:6-dihalogenanilines Expired GB457518A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH457518X 1934-11-24

Publications (1)

Publication Number Publication Date
GB457518A true GB457518A (en) 1936-11-30

Family

ID=4515644

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31295/35A Expired GB457518A (en) 1934-11-24 1935-11-12 Process for the manufacture of 2.4-dinitro-3:6-dihalogenanilines

Country Status (1)

Country Link
GB (1) GB457518A (en)

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