Organic compounds -- part of the class 532-570 series – Organic compounds – Cyclopentanohydrophenanthrene ring system containing
Patent
1991-07-22
1992-09-29
Siegel, Alan
Organic compounds -- part of the class 532-570 series
Organic compounds
Cyclopentanohydrophenanthrene ring system containing
552630, C07J 100
Patent
active
051515334
DESCRIPTION:
BRIEF SUMMARY
SUMMARY OF THE INVENTION
The invention relates to a process for the production of 3-hydroxy-1,3,5(10)-estratrien-17-one (=estrone) as well as a device for performing this process.
From German patent specification 25 37 254, a process for the production of 3-hydroxy-1,3,5(10)-estratrien-17-one by pyrolysis of 1,4-androstadiene-3,17-dione in the presence of hydrocarbons as hydrogen donors is previously known whose features are that a hydrocarbon, preheated to a temperature of 450.degree.-850.degree. C., in a mixing zone is mixed in a hydrocarbon, with a solution of 1,4-androstadiene-3,17-dione, heated to a temperature of up to 300.degree. C., the reaction gas is heated in a pyrolysis zone at a retention time of 0.001 to 60 seconds to temperatures of 450.degree.-700.degree. C. and the product leaving the pyrolysis zone is cooled off. In the embodiments of this patent specification, it is mentioned that 1,2,3,4-tetrahydronaphthalene can also be used as hydrocarbon, and that the reaction can be performed under a pressure of up to 3.times.10.sup.6 Pa.
The most significant drawback of this previously known process is to be seen in that the pyrolysis zone is quickly clogged by the formation of tar and soot in the performance of the process and the frequently, necessary cleaning of this zone impedes a performance of the process which is acceptable under economic conditions. In addition in the previously known processes, in which the reaction is performed in the gas phase, only a relatively low space-time yield of process product is obtained.
It has now been found that this drawback of the previously known process surprisingly can be avoided, if the pyrolysis is performed under a pressure of 3.5.times.10.sup.6 -3.times.10.sup.8 Pa.
Under these conditions of the process according to the invention, surprisingly high yields of process product are also achieved, overheating is avoided and a high space-time yield of process product is obtained.
The process according to the invention is performed under conditions in which both the critical temperature of 1,2,3,4-tetrahydronaphthalene of 446.degree. C. and its critical pressure of about 3.5.times.10.sup.6 Pa is exceeded, so that the reaction is performed in a supercritical fluid phase.
The process according to the invention can be performed in the devices which are described in German patent specification 25 37 254, provided that they have suitable dimensions and are manufactured from a material which withstands a pressure of 3.5.times.10.sup.6 Pa to 3.times.10.sup.8 Pa and that it contains a valve between the heat exchanger and the collecting vessel which guarantees the maintenance of the desired pressure in the pyrolysis zone.
A very suitable, sturdy and simple device is represented in attached FIG. 1. It is manufactured basically of stainless steel.
From a storage vessel 1, which contains the solution of 1,4-androstadiene-3,17-dione in 1,2,3,4-tetrahydronaphthalene, the latter is fed by a pump 2 in mixing zone 3. Simultaneously, 1,2,3,4-tetrahydronaphthalene is guided from a second storage vessel 4 by a pump 5 through a preheating cell 7 provided with a pressure guage and after reaching the desired temperature it is also fed into mixing zone 3. Mixing zone 3 is itself in the head of electrically heatable pyrolysis reactor 8, which contains a 130 mm long annular gap 9 of a 4.5 mm outer diameter and a 4.2 mm inner diameter. A thermocouple element 10 and 11 is respectively placed at the head of the annular gap and at its end.
After leaving the pyrolysis reactor, the reaction mixture is cooled in a cooling device 12 gets into collecting tank 14 by a valve 13, which guarantees the maintenance of the desired pressure in the pyrolysis zone.
It is obvious to one skilled in the art that this device can be modified according to the requirements. Thus, the device can be provided, for example, with an additional preheating cell, which also makes it possible to heat the solution of 1,4-androstadiene-3,17-dione in 1,2,3,4-tetrahydronaphthalene before it is fed into mixing zone 3. Bu
Al-Massri ZaKarya
Buback Michael
Hader Josef
Voegele Hans-Peter
Kestler Kimberly J.
Schering Aktiengesellschaft
Siegel Alan
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