GB586732A - Improvements in the nitration of aromatic hydrocarbons - Google Patents

Improvements in the nitration of aromatic hydrocarbons

Info

Publication number
GB586732A
GB586732A GB1237444A GB1237444A GB586732A GB 586732 A GB586732 A GB 586732A GB 1237444 A GB1237444 A GB 1237444A GB 1237444 A GB1237444 A GB 1237444A GB 586732 A GB586732 A GB 586732A
Authority
GB
United Kingdom
Prior art keywords
benzene
nitric acid
mono
nitrogen dioxide
catalysts
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
GB1237444A
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.)
ALFRED EDGAR ROUT
Imperial Chemical Industries Ltd
Original Assignee
ALFRED EDGAR ROUT
Imperial Chemical Industries Ltd
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 ALFRED EDGAR ROUT, Imperial Chemical Industries Ltd filed Critical ALFRED EDGAR ROUT
Priority to GB1237444A priority Critical patent/GB586732A/en
Publication of GB586732A publication Critical patent/GB586732A/en
Expired legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Metaphosphate catalysts, suitable for nitrating aromatic hydrocarbons in the vapour phase using nitric acid or nitrogen dioxide, are prepared by dissolving the metallic oxides, hydroxides, oxalates or carbonates and sometimes the metals themselves in orthophosphoric acid, evaporating to dryness and drying the solid catalyst at 250 to 400 DEG C. Phosphoric acid catalysts, for the same purpose, are made by calcining a mixture of a phosphoric acid, e.g., o- or pyro. phosphoric acid and a solid absorbent g. Kieselguhr, at 180 to 400 DEG C. Specification 463,272 is referred to.ALSO:Mono-nitro derivatives of aromatic hydrocarbons are obtained (in a process which may be used continuously) by nitrating the corresponding hydrocarbon in the vapour phase using nitric acid or nitrogen dioxide and a catalyst selected from the metallic metaphosphates, boron phosphate, solid and sup <PICT:0586732/IV/1> ported phosphoric acid catalysts. Specified products are: mono-nitrobenzene and mononitro alkyl benzenes such as mono-nitrotoluenes, mono-nitro xylenes and mono-nitroethylbenzenes. Specified catalysts are: calcium, magnesium, cadmium, nickel, ferric, ferrosoferric, strontium, copper and potassium metaphosphates. The nitrogen dioxide may be used as such, or after having been made in situ by using nitric oxide and oxygen, nitrogen trioxide and oxygen, or nitrogen pentoxide. Advantageously in the production of mononitro benzene, the molar ratio of benzene to nitric acid ranges from 3 : 1 to 1 :. Generally, the reaction temperature ranges from 130 DEG to 430 DEG C., and ordinary or elevated pressure is used. In examples: (1) an apparatus illustrated schematically, in the Figure comprises nitric acid and benzene feed tanks: (1) and (2) connected to separate vaporisers (3) and (4) leading to a converter (5) of stainless steel provided with a glass liner and connected to a condenser (6). The condensate-comprising aqueous nitric acid and an oily layer, collects in catch pot 7 while the gaseous products are passed to oxidiser (8) in which the nitric oxide is oxidised to nitrogen dioxide by means of oxygen (e.g. air) and then to the absorber (9) in which the nitrogen dioxide is absorbed in water. The condensate in 7 is passed to the decanter 10 and there separated into an oily layer and an aqueous nitric acid layer which are passed respectively to the benzene stripping still 12 attached to a condenser 13 (or two condensers in series) for the stripped benzene which is recycled to the feed tank 2; and to the still 17 (to which also that from absorber 9 is led) for concentrating the nitric acid to constant boiling strength and thence to feed tank 1. In example (2) benzene and 98 per cent nitric acid are vaporised in separate glass vessels and the vapours are heated in a glass converter filled with granules of calcium metaphosphate at a maximum temperature of 175 DEG C. The benzene and nitro benzene in the oily layer of the condensate are separated by distillation. Specification 463,272, [Group III], is referred to.
GB1237444A 1944-06-29 1944-06-29 Improvements in the nitration of aromatic hydrocarbons Expired GB586732A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1237444A GB586732A (en) 1944-06-29 1944-06-29 Improvements in the nitration of aromatic hydrocarbons

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1237444A GB586732A (en) 1944-06-29 1944-06-29 Improvements in the nitration of aromatic hydrocarbons

Publications (1)

Publication Number Publication Date
GB586732A true GB586732A (en) 1947-03-28

Family

ID=10003365

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1237444A Expired GB586732A (en) 1944-06-29 1944-06-29 Improvements in the nitration of aromatic hydrocarbons

Country Status (1)

Country Link
GB (1) GB586732A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0092372A1 (en) * 1982-04-16 1983-10-26 Sumitomo Chemical Company, Limited Process for nitration of benzene
WO2012160072A1 (en) 2011-05-24 2012-11-29 Basf Se Process for preparing polyisocyanates from biomass
US8933262B2 (en) 2011-05-24 2015-01-13 Basf Se Process for preparing polyisocyanates from biomass
EP3023412B1 (en) * 2013-07-16 2019-05-29 Mitsubishi Gas Chemical Company, Inc. Method for producing -hydroxyisobutyric acid amide and reactor

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0092372A1 (en) * 1982-04-16 1983-10-26 Sumitomo Chemical Company, Limited Process for nitration of benzene
US4551568A (en) * 1982-04-16 1985-11-05 Sumitomo Chemical Company, Limited Process for nitration of benzene
WO2012160072A1 (en) 2011-05-24 2012-11-29 Basf Se Process for preparing polyisocyanates from biomass
US8933262B2 (en) 2011-05-24 2015-01-13 Basf Se Process for preparing polyisocyanates from biomass
EP3023412B1 (en) * 2013-07-16 2019-05-29 Mitsubishi Gas Chemical Company, Inc. Method for producing -hydroxyisobutyric acid amide and reactor
US10364213B2 (en) 2013-07-16 2019-07-30 Mitsubishi Gas Chemical Company, Inc. Method for producing α-hydroxyisobutyric acid amide and reactor

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