GB859251A - A process for reducing organic nitro-compounds to amines and a catalyst for the same - Google Patents

A process for reducing organic nitro-compounds to amines and a catalyst for the same

Info

Publication number
GB859251A
GB859251A GB27688/59A GB2768859A GB859251A GB 859251 A GB859251 A GB 859251A GB 27688/59 A GB27688/59 A GB 27688/59A GB 2768859 A GB2768859 A GB 2768859A GB 859251 A GB859251 A GB 859251A
Authority
GB
United Kingdom
Prior art keywords
chloro
nitro
reduction
catalyst
compounds
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
GB27688/59A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB859251A publication Critical patent/GB859251A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
    • C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/18—Carbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/45—Monoamines
    • C07C211/46—Aniline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups

Landscapes

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

Abstract

In the reduction of halogen-substituted aromatic nitro compounds to the corresponding amines by hydrogenation in the presence of platinum-on-carbon as catalyst, dehalogenation is obviated by making the weight-ratio of nitrocompound to platinum greater than 10,000 and by providing magnesium oxide or hydroxide in the reaction medium in an amount from 0,1 to 1,0 weight per cent of the nitrocompound. The reduction is preferably carried out in the presence of water or methanol, at a temperature of 30 to 120 DEG C., and at atmospheric or superatmospheric pressure, the liquid being vigorously agitated while the hydrogen is being passed into the reaction-vessel. Detailed examples are given relating to the preparation of: ortho- and parachloroanilines, 3, 4-dichloroaniline, 2, 5-dichloroaniline, p-bromoaniline, p-fluoroaniline, 4-chloro-2-aminotoluene, 2-chloro-4-aminotoluene, o-chloro-p-phenylenediamine, 4-chloro-2-aminoanisole, 2-chloro-4-aminobenzoic acid, 6 chloro-2-amino-benzoic acid, and 4-chloro-3-aminobenzene sodium sulphonate. Brief reference is made to the reduction of the following nitro compounds: 4-chloronitronaphthalene, 4-chloro-2, 6-dinitrobenzene, 2, 6-dichloro-4-nitrophenol, 4-chloro-2, 6-dinitrophenol, 2-chloro-4-nitro-benzyl alcohol, 2-nitro 7-chloroanthraquinone, 5-chloro-3-nitro-o-phenylenediamine, 2, 6-dibromo-4-nitrophenol, 4-bromo-3-nitrobenzene sodium sulphonate, and 2-chloro-4-nitrobenzyl-malonic acid. Specifications 713,622 and 799,871 are referred to.
GB27688/59A 1958-09-17 1959-08-13 A process for reducing organic nitro-compounds to amines and a catalyst for the same Expired GB859251A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US859251XA 1958-09-17 1958-09-17

Publications (1)

Publication Number Publication Date
GB859251A true GB859251A (en) 1961-01-18

Family

ID=22194890

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27688/59A Expired GB859251A (en) 1958-09-17 1959-08-13 A process for reducing organic nitro-compounds to amines and a catalyst for the same

Country Status (1)

Country Link
GB (1) GB859251A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3145231A (en) * 1962-04-09 1964-08-18 Du Pont Process for the reduction of halo nitro aromatic compounds
DE2036313A1 (en) * 1970-07-22 1972-02-03 Farbenfabriken Bayer Ag, 5090 Leverkusen Process for the preparation of halogen-substituted aromatic amines
CN102675127A (en) * 2012-05-25 2012-09-19 山东沾化天九化工有限公司 Method and device for preparing 3,4-dichloroaniline without solvent
CN114890901A (en) * 2022-06-17 2022-08-12 老河口华辰化学有限公司 Synthesis method for synthesizing m-toluidine by 2-chloro-3-nitrotoluene one-step method

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3145231A (en) * 1962-04-09 1964-08-18 Du Pont Process for the reduction of halo nitro aromatic compounds
DE2036313A1 (en) * 1970-07-22 1972-02-03 Farbenfabriken Bayer Ag, 5090 Leverkusen Process for the preparation of halogen-substituted aromatic amines
CN102675127A (en) * 2012-05-25 2012-09-19 山东沾化天九化工有限公司 Method and device for preparing 3,4-dichloroaniline without solvent
CN114890901A (en) * 2022-06-17 2022-08-12 老河口华辰化学有限公司 Synthesis method for synthesizing m-toluidine by 2-chloro-3-nitrotoluene one-step method

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