Electrolysis: processes – compositions used therein – and methods – Electrolytic synthesis – Preparing organic compound
Reexamination Certificate
2001-10-09
2004-02-24
Wong, Edna (Department: 1753)
Electrolysis: processes, compositions used therein, and methods
Electrolytic synthesis
Preparing organic compound
C205S413000, C205S343000
Reexamination Certificate
active
06695963
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an organic electrolysis reactor for performing an electrolytic oxidation reaction. More particularly, the present invention is concerned with an organic electrolysis reactor for performing an electrolytic oxidation reaction of a system comprising a substrate and a reductant, comprising: a casing; an anode which comprises an anode active material and which is ion-conductive or active species-conductive; a cathode which comprises a cathode active material and which is ion-conductive or active species-conductive; and means for applying a voltage between the anode and the cathode, wherein the means for applying a voltage is disposed in the outside of the casing and connected to the anode and the cathode, wherein the anode and the cathode are disposed in spaced relationship in the casing to partition the inside of the casing into an intermediate compartment between the anode and the cathode, and an anode compartment on the outside of the anode.
By using the organic electrolysis reactor of the present invention to perform an electrolytic oxidation reaction, such as an electrolytic carbonylation reaction, various useful chemical compounds, for example a carbonic diester, can be produced efficiently, safely and stably, with high selectivity under moderate conditions.
The organic electrolysis reactor of the present invention can solve the various problems of a non-electrolytic oxidation reaction which is performed by using a catalyst, i.e., the problems that a deterioration of a catalyst occurs, that the selectivity for and yield of a desired product become low, that complicated operations are necessary, and that a large amount of energy is consumed.
For example, when the production of a carbonic diester from carbon monoxide and an alcohol by an electrolytic carbonylation reaction is performed by using the organic electrolysis reactor of the present invention, there can be obtained advantages not only in that the carbonic diester can be produced efficiently, with high selectivity and at low cost under moderate conditions, but also in that the reactor of the present invention can solve the various problems of the conventional methods for producing a carbonic diester, such as the problems that the use of phosgene (which is poisonous) is necessary, that a corrosion of a reactor by a by-produced chlorine-containing compound occurs, that a deterioration of a catalyst occurs, that there occurs formation of a dangerous, explosive mixture of a starting material with oxygen, and that the selectivity for and yield of a desired carbonic diester become low.
The organic electrolysis reactor of the present invention can be used not only for performing an electrolytic carbonylation reaction, but also for performing electrolytic oxidation reactions other than an electrolytic carbonylation reaction, such as oxidation of an alkane, oxidation of an alcohol, epoxidation of an olefin, oxidation of a benzylic site, oxidation of an allylic site, oxidation of an aromatic ring of an aromatic hydrocarbon, oxidation of a sulfur compound and oxidation of a nitrogen compound. In addition, the organic electrolysis reactor of the present invention can also be used for performing an oxidative addition reaction by electrolysis, with respect to such a type of oxidative addition reaction as conventionally, usually performed by a non-electrolytic method.
The present invention is also concerned with a method for producing a chemical compound by performing an electrolytic oxidation reaction, using the organic electrolysis reactor mentioned above.
2. Prior Art
There are an extremely wide variety of oxidation reactions. One of such oxidation reactions is an electrolytic oxidation reaction.
An oxidation reaction using an electrolysis can be performed as follows. An anode and a cathode are placed in an electrolyte solution containing a substance to be oxidized. A voltage is applied between the anode and the cathode to thereby electrolyze the substance, so that the substance is oxidized at the anode. Such an oxidation reaction using an electrolysis is called an “electrolytic oxidation reaction”. In some cases, an oxidation reaction which hardly proceeds under ordinary reaction conditions not utilizing an electrolysis can easily proceed by electrolytic oxidation. Therefore, the electrolytic oxidation reaction is extremely useful.
The electrolytic oxidation is applicable to an extremely wide variety of oxidation reactions, such as oxidation of an alkane, oxidation of an alcohol, epoxidation of an olefin, oxidation of a benzylic site, oxidation of an allylic site, oxidation of an aromatic ring of an aromatic hydrocarbon, oxidation of a sulfur compound, and oxidation of a nitrogen compound.
Further, the electrolytic oxidation reaction is also applicable to oxidation reactions which are collectively referred to as the “oxidative addition reaction ” and which are usually performed by a non-electrolytic method. Examples of such oxidative addition reactions include the Wacker reaction for the synthesis of an aldehyde and a ketone from an olefin, acetoxylation, oxychlorination or oxycyanation of an olefin or an aromatic hydrocarbon, a coupling reaction of an olefin or an aromatic hydrocarbon, and a reaction for the synthesis of an ester from an alcohol (see, for example, “Shokubai Koza Vol. 8, (Kogyo Shokubai Hannohen 2), Kogyo Shokubai Hanno I (Lecture on Catalysts Vol. 8 (Commercial Catalytic Reactions No. 2), Commercial Catalytic Reactions I)”, edited by Japan Catalyst Society, p. 196, 1985, Japan). Furthermore, the electrolytic oxidation reaction is also applicable to a carbon monoxide insertion reaction (carbonylation reaction), which is a variant of the oxidative addition reaction.
Hereinbelow, an explanation will be made with respect to the prior art of the production of a chemical compound by the electrolytic oxidation reaction, taking the carbonylation reaction as an example.
In general, for overcoming a thermodynamic disadvantage, a carbonylation reaction is performed in the presence of oxygen while by-producing water. Such an ordinary carbonylation reaction which is performed without utilizing an electrolysis is represented by the following formula:
R—H+R′—H+CO+1/2O
2
→R—CO—R′+H
2
O.
That is, the carbonylation reaction is a reaction performed by subjecting two molecules of substrates each having a hydrogen atom (R—H and R′—H) and carbon monoxide to condensation in the presence of oxygen to thereby produce a condensation product while liberating hydrogen and converting the liberated hydrogen (hydrogen ions) into water.
The carbonylation reaction is generally performed by using a catalyst. Examples of such catalysts include the elements of the Groups 8, 9, 10 and 11 of the Periodic Table, such as palladium, and compounds of these elements.
As a substrate (R—H and/or R′—H), a wide variety of compounds can be used. Examples of substrates include organic compounds, such as an olefin (e.g. a polyene, such as a diene), an alcohol, an aromatic compound; and inorganic compounds, such as water. The substrates, R—H and R′—H, may be the same or different.
As examples of carbonylation reactions, there can be mentioned a reaction for the synthesis of an unsaturated carboxylic acid from an olefin and water, a reaction for the synthesis of an unsaturated ester from an olefin and an alcohol, a reaction for the synthesis of a dialkyl carbonate and a dialkyl oxalate from an alcohol, a reaction for the synthesis of a diaryl carbonate from phenol, and a reaction for the synthesis of a urea analogue and an oxalic diamide (oxamide) from an amine (see, for example, “Shokubai Koza Vol. 9 (Kogyo Shokubai Hanno-hen 3), Kogyo Shokubai Hanno II (Lecture on Catalysts Vol. 9 (Commercial Catalytic Reactions No. 3), Commercial Catalytic Reactions II)”, edited by Japan Catalyst Society, p. 31, 1985, Japan).
The carbonylation reactions, which can be used to produce useful chemical compounds efficiently, are of great use
Otsuka Kiyoshi
Suzuki Ken
Yamanaka Ichiro
Asahi Kasei Kabushiki Kaisha
Wong Edna
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