Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1990-12-10
1992-05-05
Lone, Werren B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568719, 568718, 568722, 568728, C07C 3912, C07C 3720
Patent
active
051109948
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The invention concerns a process for making 9,9-vis(4-hydroxyphenyl)fluorene by reacting fluorenone with excess phenol in a condensation reaction while using hydrochloric-acid gas as the condensing agent and aluminum trichloride as the catalyst.
STATE OF THE ART
A method of this sort is known from the European patent document A 00 65 060 wherein the solid catalyst, for instance AlCl.sub.3, is added to the reaction mixture and the hydrochloric-acid gas is introduced into the reaction mixture during the reaction. It is important in this respect that the temperature in the reaction vessel shall not exceed 60.degree.-80.degree. C. This method makes it possible to substantially impede formation of isomers of 9,9-bis(4-hydrophenyl)fluorene and of byproducts of higher condensation. However where synthesis batches in large vessels are concerned, this method incurs several process-technological drawbacks. One of these is that the solid, pulverulent catalyst (AlCl.sub.3) cannot be kept in suspension in the reaction mixture but instead soon settles at the bottom of this vessel and there is then danger of clogging the bottom discharge valves. Moreover it is no simple matter to introduce the hydrochloric-acid gas over the time of reaction, which is several hours. Lastly the heat release in this known method--especially where large batches and increasing viscosities are concerned--can be controlled only poorly by means of wall cooling.
DESCRIPTION OF THE INVENTION
The object of the invention is to create a process of the initially cited kind that shall be free of the above drawbacks.
The basic problem of the invention is solved by the innovative process in that aluminum chloride is dissolved in an anhydrous organic solvent of mixture of solvents at least nearly inert relative to the condensation reaction, where this solvent or at least one component of the mixture of solvents evinces the property of electron donor, with simultaneous introduction of hydrochloric-acid gas, in order to prepare a liquid catalyst, and in that this liquid catalyst is dripped into the reaction mixture subjected to agitation, the temperature of the reaction mixture being kept below 60.degree. C. during this dripping procedure by controlling the catalyst addition rate.
In an advantageous implementation of the process of the invention, the solvent or the component of the mixture of solvents is benzene or a substituted benzene, preferably toluene.
In another advantageous implementation of the invention, the solvent or the component of the mixture of solvents is an ether. This ether advantageously may be methyl-tert.-butylether.
ILLUSTRATIVE IMPLEMENTATION OF THE INVENTION
A) Substances Used
80.degree.-82.degree. C. and a density of 1.13 g/cm.sup.3, gas, anhydrous toluene.
B) Preparing the Liquid Catalyst
Three liters of anhydrous toluene and the stated amount of aluminum chloride are placed in a flask equipped with agitator. Next and at room temperature, hydrochloric-acid gas is introduced, in the presence of constant agitation, into the flask until the entire aluminum trichloride has dissolved and a two-phase, liquid system has been created. The supernatant phase consists mainly of toluene and the hydrochloric-acid gas dissolved therein.
C) Carrying Out the Synthesis
The solid fluorenone is placed in a 100-liter reaction vessel and is mixed with phenol heated to 60.degree. C., that is in the liquid state, with agitation. The reaction mixture is heated to 40.degree. to 50.degree. C. Then, with further agitation, the liquid catalyst is slowly dripped in and thereby the temperature is kept at about 50.degree. C. Dripping the catalyst requires about 11/2 h.
After termination of catalyst addition, increase of the viscosity of the reaction mixture--from which the raw product already accumulates in part--is noted. After 4 to 5 h from the beginning of the reaction, 20 liters of hot water are added and thereupon the excess phenol is removed by steam distillation.
Following phase separation, the supernatant water is decan
REFERENCES:
patent: 2775620 (1956-12-01), Williamson
patent: 4024194 (1977-05-01), Corn, Jr.
patent: 4048200 (1977-09-01), Tresper et al.
patent: 4049721 (1977-09-01), Corn, Jr. et al.
patent: 4675458 (1987-06-01), Riemann et al.
ISONOVA Technische Innovationen G.m.b.H
Lone Werren B.
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