GB797483A - Improvements in or relating to catalytic hydrogenation of nitrosamines - Google Patents

Improvements in or relating to catalytic hydrogenation of nitrosamines

Info

Publication number
GB797483A
GB797483A GB3327156A GB3327156A GB797483A GB 797483 A GB797483 A GB 797483A GB 3327156 A GB3327156 A GB 3327156A GB 3327156 A GB3327156 A GB 3327156A GB 797483 A GB797483 A GB 797483A
Authority
GB
United Kingdom
Prior art keywords
palladium
carbon
nitrosamine
platinum
hydrogen
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
GB3327156A
Inventor
Dewey Robert Levering
Lucien Garnett Maury
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.)
Hercules Powder Co
Original Assignee
Hercules Powder 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 Hercules Powder Co filed Critical Hercules Powder Co
Priority to GB3327156A priority Critical patent/GB797483A/en
Publication of GB797483A publication Critical patent/GB797483A/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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C241/02—Preparation of hydrazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/03—Precipitation; Co-precipitation

Landscapes

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

Abstract

Hydrazines are produced by reacting a nitrosamine with hydrogen at a pressure above atmospheric and in the presence of particulate catalytic material comprising a Group 8 metal selected from palladium, platinum, rhodium, nickel, cobalt and iridium, said catalytic material having a specific surface area of at least 15 square metres per gram, said nitrosamine being of sufficiently high purity to thereby undergo reaction with hydrogen to form said hydrazine. Preferably a hydrogen pressure of between about 50 and 10,000 p.s.i.g. and a temperature of from about 20 DEG to 75 DEG C. will be employed. Palladium supported on carbon, alumina, silica, silica-alumina, or titania, is the preferred catalyst, but platinum employed as platinum oxide or platinum supported on carbon is nearly as effective. The nitrosamine starting materials may be produced by nitrosation of the corresponding secondary amines with nitric oxide as described in Specification 789,702. The nitrosamines may be dialkyl, diaryl, mixed alkylaryl or heterocyclicnitrosamines, or the nitrosamine may contain more than one nitroso group in which case the dihydrazine product can be obtained. The nitrosamine may also contain carboxyl, hydroxyl or ester groups. A list of suitable nitrosamines is given. The starting material may be purified by fractionation, solvent extraction, or recrystallization. It is preferred to fractionate the material in a column having at least four theoretical plates. The hydrogenation is preferably effected in an inert solvent such as water, hydrocarbons such as toluene, chlorinated hydrocarbons, or alcohols such as ethanol. In examples: 17 to 74 grams of nitrosamine is charged into a pressure vessel (either a Parr shaker bottle or a rocking autoclave) and agitated under various conditions of temperature and pressure, the catalyst being a supported catalyst comprising 5 per cent by weight of the metal. The starting materials and catalysts are as follows: dimethyl nitrosamine with platinum oxide, Raney cobalt, Raney nickel, palladium on carbon, platinum/carbon, rhodium/carbon, and palladium/calcium carbonate; diethylnitrosamine with palladium/carbon; nitrosopiperidine with palladium/carbon; diamylnitrosamine with palladium/carbon; dinitrosopiperazine with palladium carbon. Ruthenium and potassium perrhenate are shown to be inoperative as catalysts, and comparative examples in which the catalytic materials have a specific surface of below 15 square metres per gram are described. Example (49) describes a continuous process using a palladium-on-alumina catalyst which is supported in a layer of toluene which floats on a water layer in a stainless steel reactor; dimethylnitrosamina is continuously introduced at the top of the reactor, hydrogen at 300 p.s.i.g. is continuously introduced and the water layer containing the products of reaction, dimethylhydrazine, dimethylamine and ammonia is continuously removed.
GB3327156A 1956-10-31 1956-10-31 Improvements in or relating to catalytic hydrogenation of nitrosamines Expired GB797483A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3327156A GB797483A (en) 1956-10-31 1956-10-31 Improvements in or relating to catalytic hydrogenation of nitrosamines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3327156A GB797483A (en) 1956-10-31 1956-10-31 Improvements in or relating to catalytic hydrogenation of nitrosamines

Publications (1)

Publication Number Publication Date
GB797483A true GB797483A (en) 1958-07-02

Family

ID=10350763

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3327156A Expired GB797483A (en) 1956-10-31 1956-10-31 Improvements in or relating to catalytic hydrogenation of nitrosamines

Country Status (1)

Country Link
GB (1) GB797483A (en)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3113152A (en) * 1959-01-05 1963-12-03 Fmc Corp Preparation of methylhydrazine
US3129263A (en) * 1958-11-21 1964-04-14 Fmc Corp Preparation of hydrazine derivatives
US3133120A (en) * 1959-11-19 1964-05-12 Allied Chem Vapor phase hydrogenation of nitrosodialkylamines
US3153095A (en) * 1958-11-17 1964-10-13 Commercial Solvents Corp Process for the production of dialkylhydrazines
US3167588A (en) * 1959-12-01 1965-01-26 Allied Chem Catalytic hydrogenation of nitrosodialkylamines to produce unsymmetrical dialkylhydrazines
US3169993A (en) * 1959-08-17 1965-02-16 Allied Chem Catalytic hydrogenation of nitrosodialkylamines
US3182086A (en) * 1955-07-20 1965-05-04 Hercules Powder Co Ltd Catalytic hydrogenation of nitrosamines to hydrazines
US3187051A (en) * 1956-02-10 1965-06-01 Du Pont Process for the preparation of unsymmetrical dialkyl hydrazines
US3214474A (en) * 1953-09-28 1965-10-26 Aerojet General Co Preparation of unsymmetrical hydrazines
US3271454A (en) * 1957-02-20 1966-09-06 Allied Chem Production of unsymmetrical dialkylhydrazines
US3274251A (en) * 1962-08-17 1966-09-20 Electro Chimie Metal Production of unsymmetrical dimethylhydrazine
US3296307A (en) * 1962-09-27 1967-01-03 Allied Chem Production of monoalkylhydrazines
WO2014011041A1 (en) 2012-07-11 2014-01-16 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Nitrosamine and/or nitramines reduction in a liquid medium

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3214474A (en) * 1953-09-28 1965-10-26 Aerojet General Co Preparation of unsymmetrical hydrazines
US3182086A (en) * 1955-07-20 1965-05-04 Hercules Powder Co Ltd Catalytic hydrogenation of nitrosamines to hydrazines
US3187051A (en) * 1956-02-10 1965-06-01 Du Pont Process for the preparation of unsymmetrical dialkyl hydrazines
US3271454A (en) * 1957-02-20 1966-09-06 Allied Chem Production of unsymmetrical dialkylhydrazines
US3153095A (en) * 1958-11-17 1964-10-13 Commercial Solvents Corp Process for the production of dialkylhydrazines
US3129263A (en) * 1958-11-21 1964-04-14 Fmc Corp Preparation of hydrazine derivatives
US3113152A (en) * 1959-01-05 1963-12-03 Fmc Corp Preparation of methylhydrazine
US3169993A (en) * 1959-08-17 1965-02-16 Allied Chem Catalytic hydrogenation of nitrosodialkylamines
US3133120A (en) * 1959-11-19 1964-05-12 Allied Chem Vapor phase hydrogenation of nitrosodialkylamines
US3167588A (en) * 1959-12-01 1965-01-26 Allied Chem Catalytic hydrogenation of nitrosodialkylamines to produce unsymmetrical dialkylhydrazines
US3274251A (en) * 1962-08-17 1966-09-20 Electro Chimie Metal Production of unsymmetrical dimethylhydrazine
US3296307A (en) * 1962-09-27 1967-01-03 Allied Chem Production of monoalkylhydrazines
WO2014011041A1 (en) 2012-07-11 2014-01-16 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Nitrosamine and/or nitramines reduction in a liquid medium

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