Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
1999-03-16
2001-11-13
Shippen, Michael L. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S723000
Reexamination Certificate
active
06316677
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a process of the production of bisphenol compounds, which are useful as raw materials of thermoplastic polymers, surface-active agents and stabilizers.
With respect to the process of producing a bisphenol compound, German Patent No. 2,534,558 and JP 58-13528 A (Tokkaisho) each disclose a process in which an &agr;, &agr;″-dihydroxydiisopropylbenzene or a diisopropenylbenzene is reacted with a phenol in the presence of an acidic catalyst such as an ion exchange resin.
In these processes, however, there is a problem that the isolation yield of a bisphenol compound, the intended product, from a reaction mixture is low. This is because an acid, isolated from an ion exchange resin in the reaction, generates a high order adduct of a bisphenol compound when the reaction mixture is heated to remove phenol after the reaction. To solve the problem, JP 8-13770 B (Tokkohei) discloses a process in which excess phenol is distilled off from the reaction mixture containing a bisphenol compound after neutralization by adding a base such as disodium hydrogen phosphate. Then, the resulting mixture is washed with water after the removal of phenol. The bisphenol compound is isolated through crystallization and drying.
This process prevents the production of high order adducts of bisphenol compound but needs inorganic base aqueous solutions for neutralization when bisphenol compounds are isolated from the reaction mixture and purified as the intended products. Moreover, there is a problem in that waste water that contains phenol is generated inevitably and its treatment costs are very high.
JP 5-44932 B (Tokkohei) discloses a process in which a small amount of hydrogen chloride remaining in bisphenol A is removed with anion exchange resins that have pyridyl groups and excellent thermal stability at temperatures higher than 100° C. The gazette does not disclose bisphenol M that is produced according to the present invention, and discloses that basic ion exchange resins having secondary or tertiary amines as exchange groups cannot be used in the production of bisphenol A.
DESCRIPTION OF THE INVENTION
The present inventors recognized that there were the above-mentioned problems in the production of bisphenol compounds and studied separation and purification steps to solve the above-mentioned problems.
The present inventors thought that neutralization could be carried out by using an anion exchange resin such as Amberlist A-21 when a free acid generated in the reaction is removed. Because bisphenol A, as disclosed in JP 5-44932 B, is produced by removing hydrogen chloride without existence of solvent, the reactant product must be heated higher than 100° C. for treating in a fused state.
Therefore, it was impossible to use basic ion exchange resin having at least one group of amino group or quaternary ammonium salt group in the process of JP 5-44932.
The present inventors have found that when a step for neutralization of reaction products is done in the presence of at least one solvent selected from the group consisting of aromatic hydrocarbon compounds and aliphatic hydrocarbon compounds, because it is possible to deal with a reaction product at lower than 100° C., it is possible to use an anion exchange resin in the neutralization step.
Thus the use of an inorganic base aqueous solution became unnecessary and a process free from waste water could be constructed. They treated the reaction mixture with an anion exchange resin in place of conventional alkali washing, and found that the thus obtained bisphenol compounds were usable offering no problem of quality and the isolation yield was satisfactory.
Accordingly, the present invention includes the following items.
(1) A process for the production of a bisphenol compound comprising:
a step for reacting a phenolic compound (a) with at least one compound (b) selected from the group consisting of dialkenylbenzene compounds, bis(hydroxyalkyl)benzene compounds and (hydroxyalkyl)-alkenylbenzene compounds or at least one compound (c) selected from the group consisting of monoalkenylphenolic compounds and mono(hydroxyalkyl)phenolic compounds in the presence of an acidic catalyst to obtain a reaction mixture containing said bisphenol compound,
a step for neutralizing said reaction mixture with an anion exchange resin,
a step for removing the phenolic compound remaining in said reaction mixture to concentrate said neutralized reaction mixture, and
a step for isolating said bisphenol compound from said concentrated mixture.
(2) A process as described above in (1), wherein said acidic catalyst is a cation exchange resin.
(3) A process as described above in (1), wherein said step for neutralizing is carried out in at least one solvent selected from the group consisting of aromatic hydrocarbon compounds and aliphatic hydrocarbon compounds.
(4) A process as described above in (1), wherein said reaction is carried out in at least one solvent selected from the group consisting of aromatic hydrocarbon compounds and aliphatic hydrocarbon compounds.
(5) A process as described above in (1), wherein said anion exchange resin is an ion exchange resin having at least one basic group selected from the group consisting of amino groups and quaternary ammonium salts.
(6) A process as described above in (1), wherein said isolation is carried out by crystallization.
(7) A process as described above in (6), wherein toluene or xylene is used as the solvent of said crystallization.
The preparation process of bisphenol compounds, related to the present invention, will concretely be described.
With respect to the preparation process of bisphenol compounds related to the present invention, illustrative examples of the raw material of the reaction include a phenolic compound (a), at least one compound (b) selected from the group consisting of dialkenylbenzene compounds, bis(hydroxyalkyl)benzene compounds and (hydroxyalkyl)alkenylbenzene compounds or at least one compound (c) selected from the group consisting of monoalkenylphenolic compounds and mono(hydroxyalkyl)phenolic compounds.
In this case, illustrative examples of the phenolic compound include aromatic hydrocarbons having a phenolic hydroxyl group, such as phenol, o- or p-cresol, o- or p-ethylphenol, m-isopropylphenol, 2,6-xylenol, 3,5-xylenol, 1-naphthol and 2-naphthol.
Illustrative examples of the alkenyl group and the hydroxy group of the above-mentioned dialkenylbenzene compounds, (hydroxyalkyl)alkenylbenzene compounds and monoalkenylphenolic compounds (b), and bis(hydroxyalkyl)benzene compounds, (hydroxyalkyl)alkenylbenzene compounds and mono(hydroxyalkyl)phenolic compounds (c) include 1-alkenyl groups preferably having 1-6 carbon atoms, such as vinyl group, isopropenyl group, 1-ethylvinyl group and 1-propylvinyl group, and include 1-hydroxyalkyl groups preferably having 1-6 carbon atoms, such as hydroxymethyl group, 1-hydroxyethyl group, 1-hydroxy-1-methylethyl group, 1-hydroxy-1-methylpropyl group and 1-hydroxy-1-ethylpropyl group.
The substitution format of the above-mentioned dialkenylbenzene compounds, bis(hydroxyalkyl)benzene compounds, (hydroxyalkyl)alkenylbenzene compounds, monoalkenylphenolic compounds and mono(hydroxyalkyl)phenolic compounds may be any of the o-, m- and p-substitutions.
In the above-mentioned compound (b), reacted with the phenolic compound (a) in the present invention, illustrative examples of the dialkenylbenzene compounds include divinylbenzenes, diisopropenylbenzenes, isopropenylvinylbenzenes and bis(1-ethylvinyl)benzenes. Illustrative examples of the bis(hydroxyalkyl)benzene compounds include bis(hydroxymethyl)benzenes, bis(1-hydroxyethyl)benzenes, bis(1-hydroxy-1-methylethyl)benzenes and bis(1-hydroxy-1-methylpropyl)benzenes. Illustrative examples of the (hydroxyalkyl)alkenylbenzene compounds include (1-hydroxyethyl)vinylbenzene, (1-hydroxy-1-methylethyl)-vinylbenzene, (1-hydroxyethyl)-isopropenylbenzene and (1-hydroxy-1-methylpropyl)-(1-ethylvinyl)benzene.
In the above-mentioned compound (c), reacted with the phenolic compound (
Enna Masahiro
Isaka Toshiyuki
Nagai Naoshi
Burns Doane Swecker & Mathis L.L.P.
Mitsui Chemicals Inc.
Shippen Michael L.
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