DE977706C - Process for the preparation of 1, 3, 5-trinitro-2, 4, 6-trichlorobenzene - Google Patents

Process for the preparation of 1, 3, 5-trinitro-2, 4, 6-trichlorobenzene

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Publication number
DE977706C
DE977706C DEJ20222A DEJ0020222A DE977706C DE 977706 C DE977706 C DE 977706C DE J20222 A DEJ20222 A DE J20222A DE J0020222 A DEJ0020222 A DE J0020222A DE 977706 C DE977706 C DE 977706C
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DE
Germany
Prior art keywords
trichlorobenzene
trinitro
preparation
nitration
parts
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
DEJ20222A
Other languages
German (de)
Inventor
Hans Mueller V D Dr Haegen
Karl Dr Meyer
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.)
Bundesrepublik Deutschland
Original Assignee
Bundesrepublik Deutschland
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 Bundesrepublik Deutschland filed Critical Bundesrepublik Deutschland
Priority to DEJ20222A priority Critical patent/DE977706C/en
Application granted granted Critical
Publication of DE977706C publication Critical patent/DE977706C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von 1,3 ,5-Trinitro-2,4,6-Trichlorbenzol Trinitrotrichlorbenzol hat in neuerer Zeit als Ausgangsmaterial für Explosivstoffe bzw. auf Grund seiner ausreichenden Detonationsfähigkeit als Sprengstoff für Panzerabwehrladungen Verwendung gefunden. Process for the preparation of 1,3,5-trinitro-2,4,6-trichlorobenzene Trinitrotrichlorobenzene has recently been used as a starting material for explosives or because of its sufficient detonation capability as an explosive for anti-tank charges use found.

Die Herstellung des r,3,5-Trinitro-2,4,6-trichlorbenzols erfolgt nach 0. Turek in über 800/obiger Ausbeute (Chimie et industrie, 26 [1931] 78I; deutsche Patentschrift 767 5Io) aus I,3,s-Trichlorbenzol durch Lösen in 350/oigem Oleum, Zusatz von rauchender Salpetersäure (gemäß der deutschen Patentschrift 767 mio durch Lösen in einer als Nitryltetrasulfat bezeichneten Nitriersäure) und Erhitzen auf I40 bis I500 C bis kein Reaktionsprodukt mehr ausfällt. Die Ausbeute gemäß der genannten Patentschrift beträgt 730/0. Die lange Reaktionszeit (g Stunden gemäß dem Beispiel der genannten Patentschrift) erwies sich als unwirtschaftlich. The production of r, 3,5-trinitro-2,4,6-trichlorobenzene takes place after 0. Turek in over 800 / above yield (Chimie et industrie, 26 [1931] 78I; German Patent specification 767 5Io) from I, 3, s-trichlorobenzene by dissolving in 350% oleum, Addition of fuming nitric acid (according to the German patent 767 mio Dissolve in a nitrating acid called nitryl tetrasulphate) and heat I40 to I500 C until no more reaction product precipitates. The yield according to the above Patent is 730/0. The long reaction time (g hours according to the example of the patent mentioned) turned out to be uneconomical.

Es wurde festgestellt, daß bei diesen bekannten Verfahren das zunächst während der Nitrierung ausfallende Reaktionsprodukt ein Gemisch aus Dinitrochlorbenzol mit Trinitrochlorbenzol darstellt. It was found that in these known methods the first The reaction product which precipitates out during the nitration is a mixture of dinitrochlorobenzene with trinitrochlorobenzene.

Die Weiternitrierung im heterogenen System erfolgt erst nach langer Reaktionszeit mit fortschreitender Ausbeuteminderung.Further nitration in the heterogeneous system takes a long time Response time with progressive reduction in yield.

Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von I,3,5-Trinitro-2,4,6-trichlorbenzol durch Nitrieren von I,3,5-Trichlorbenzol in Salpetersäureoleumgemischen, das dadurch gekennzeichnet ist, daß die Nitrierung bei Temperaturen oberhalb 1400 C in geschlossenen Nitrierapparaten, also unter Druck, erfolgt. Die Durchführung der Nitrierung erfolgt unter Anwendung üblicher Säureverhältnisse in homogener Phase. Unter den genannten Bedingungen ergibt sich eine Erniedrigung der Reaktionszeit auf 3 bis 5 Stunden. Damit stellt diese neue Methode zur Herstellung dieses Sprengstoffes einen wesentlichen technischen Fortschritt dar. The present invention relates to a method of production of 1,3,5-trinitro-2,4,6-trichlorobenzene by nitrating 1,3,5-trichlorobenzene in nitric acid oil mixtures, which is characterized in that the nitration at temperatures above 1400 C in closed nitriding apparatus, i.e. under pressure, he follows. the The nitration is carried out using the application usual acid ratios in homogeneous phase. Under the stated conditions results the reaction time is reduced to 3 to 5 hours. So this represents new method of producing this explosive an essential technical Progress.

Beispiel I,85 Teile (Gewichtsteile) I,3,5-Trichlorbenzol werden innerhalb I Stunde bei 70 bis go0 C in 20 Teile einer Nitriersäure (bestehend aus 12 Teilen 600/obigem Oleum und 8 Teilen rauchender Salpetersäure) eingetragen. Darauf wird der Nitrierapparat verschlossen und die Temperatur unter Rühren innerhalb 2 Stunden auf I50 bis I650 C gesteigert. Es wurden Drücke unterhalb 10 atü beobachtet. Bei dieser Temperatur wird 2 Stunden weitergerührt. Nach dem Abkühlen wird das abgeschiedene Rohprodukt von der Restsäure abgesaugt und mit Wasser neutral gwaschen. Es resultieren 2,30 bis 2,70 Teile Trinitrotrichlorbenzol vom Schmelzpunkt I80 bis I850 C. Durch Umkristallisieren aus Cloroform wird der Stoff rein (F I88 bis I90° C) erhalten. Die Ausbeute beträgt im Mittel 77,5 ovo der Theorie an Rohprodukt bzw. Example I, 85 parts (parts by weight) of I, 3,5-trichlorobenzene are within I hour at 70 to 0 C in 20 parts of a nitrating acid (consisting of 12 parts 600 / above oleum and 8 parts of fuming nitric acid). On it will the nitriding apparatus closed and the temperature with stirring within 2 hours increased to I50 to I650 C. Pressures below 10 atmospheres were observed. at this temperature is stirred for a further 2 hours. After cooling, the deposited The residual acid is sucked off the crude product and washed neutral with water. It result 2.30 to 2.70 parts of trinitrotrichlorobenzene with a melting point of 180 to 1850 C. Avg When recrystallized from chloroform, the substance is obtained in pure form (F 188 to 190 ° C.). The average yield is 77.5 ovo of theory of crude product or

72,5 O/o an Reinprodukt, bezogen auf I,3,5-Trichlorbenzol.72.5% of pure product, based on 1,3,5-trichlorobenzene.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von I,3,s-Trinitro-2,4,6-trichlorbenzol durch Nitrieren von I,3,5-Trichlorbenzol in Salpetersäureoleumgemischen, dadurdi gekennzeidhnet, daß die Nitrierung bei Temperaturen oberhalb I400 C unter Druckeinwirkung in homogener Phase vorgenommen wird. ~~~~~~~~ In Betracht gezogene Druckschriften: Deutsche Patentschrift Nr. 767 5Io; Chimie et industrie, 26 (I93I), S.78I; J. org. Chemistry. 25 (Ig60), S. 1037 und Io38 PATENT CLAIM: Process for the production of I, 3, s-trinitro-2,4,6-trichlorobenzene by nitrating 1,3,5-trichlorobenzene in nitric acid oil mixtures, dadurdi marked that the nitration at temperatures above 1400 C under the action of pressure is carried out in a homogeneous phase. ~~~~~~~~ Publications considered: German Patent No. 767 50; Chimie et industrie, 26 (I93I), p.78I; J. org. Chemistry. 25 (Ig60), p. 1037 and Io38
DEJ20222A 1961-07-14 1961-07-14 Process for the preparation of 1, 3, 5-trinitro-2, 4, 6-trichlorobenzene Expired DE977706C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEJ20222A DE977706C (en) 1961-07-14 1961-07-14 Process for the preparation of 1, 3, 5-trinitro-2, 4, 6-trichlorobenzene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEJ20222A DE977706C (en) 1961-07-14 1961-07-14 Process for the preparation of 1, 3, 5-trinitro-2, 4, 6-trichlorobenzene

Publications (1)

Publication Number Publication Date
DE977706C true DE977706C (en) 1968-07-11

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DEJ20222A Expired DE977706C (en) 1961-07-14 1961-07-14 Process for the preparation of 1, 3, 5-trinitro-2, 4, 6-trichlorobenzene

Country Status (1)

Country Link
DE (1) DE977706C (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE767510C (en) * 1936-08-12 1952-09-15 Chem Fab Griesheim Process for the preparation of 1, 3, 5-trichloro-2, 4, 6-trinitrobenzene

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE767510C (en) * 1936-08-12 1952-09-15 Chem Fab Griesheim Process for the preparation of 1, 3, 5-trichloro-2, 4, 6-trinitrobenzene

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