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piperazine

Product name piperazine
Synonyms hexahydropyrazine
piperazidine
diethylenediamine
GOST no data
CAS 110-85-0

Piperazine is a colorless, hygroscopic, crystalline compound with weak amine odor and saline taste. It is freely soluble in water, glycols and glycerol; boundedly soluble in ethanol, almost insoluble in diethyl ether. It crystallizes from water solutions as hexahydrate [CAS 142-63-2; melting point 44-45°C, boiling point 145-156°C]

Piperazine exhibits most of chemical properties secondary aliphatic amines. It forms salts with mineral and carboxylic acids on one or both nitrogen atoms. Alkylation, arylation (including quaternization), acylation, chlorination and other reactions usually occur on both nitrogen atoms at once. In order to obtain monosubstituted derivatives one nitrogen atom is protected with easy-off functional group. Piperazine easily dehydrogenates in the presence of catalysts to form pyrazine.

Piperazine itself possesses a low toxicity for human, animals and poultry. It has a remarkable power to dissolve uric acid and producing a soluble urate, but in clinical experience it has not proved equally successful. Also it is known about it antihelmintic activity. Many piperazine derivatives are physiologically active compounds. Thus, its moiety exists in a number of psychotropic agents, other pharmaceuticals (including Viagra) and some drugs (e.g. ecstasy);

Production.

There are some routes for industrial piperazine preparation:

  • as a by-product in ethylene diamine manufacturing by the combining of 1,2-dichloroethane with ammonia;
  • by heating of ethylene diamine at 175-200°C in the presence of catalyst (nickel, cobalt, copper or platinum):

    piperazine synthesis from ethylene diamine


  • by dehydratation of monoethanol amine or ethanol amines mixture at 150-300°C, pressure 10-25MPa (NH3 and H2). Process is catalyzed with zinc chloride ZnCl2 or orthophosphoric acid H3PO4 or aluminum oxide:

    pyperazine preparation from ethanolamines


    Uses.

  • in medicine and veterinary as an antihelmintic drug (as hexahydrate, adipinate or citrate);
  • in pharmaceutical industry as an intermediate in preparation of psychotropic, spasmolytic, antihistamine, antiemetic, anaesthetic, impotence, leukemia drugs;
  • as a corrosion inhibitor;
  • as a polymerization accelerator for chloroprene rubbers and hardener for epoxy resins;
  • as a feedstock in manufacturing of high-melting polyamides (copolymerization with phthalic acid chloroanhydrides);
  • as an intermediate in insecticides, antioxidants and other fine chemicals production;

  • Manufacturer(s) no data
    Chemical structure of piperazine

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