Electrolysis: processes – compositions used therein – and methods – Electrolytic synthesis – Preparing organic compound
Reexamination Certificate
2001-10-09
2003-05-27
Wong, Edna (Department: 1741)
Electrolysis: processes, compositions used therein, and methods
Electrolytic synthesis
Preparing organic compound
C205S413000, C205S439000, C205S440000, C205S441000, C429S010000, C429S010000, C429S006000
Reexamination Certificate
active
06569309
ABSTRACT:
This nonprovisional application claims priority under 35 U.S.C. §119(a) on Patent Application No. 2001-204435 filed in JAPAN on Jul. 5, 2001, which is herein incorporated by reference.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a fuel cell type reactor and a method for producing a chemical compound by using the reactor. More particularly, the present invention is concerned with a fuel cell type reactor for performing an oxidation reaction of a system comprising a substrate, a reductant and an oxidant, comprising: a casing; an anode which comprises an anode active material and which is ion-conductive or active species-conductive; and a cathode which comprises a cathode active material and which is ion-conductive or active species-conductive, 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, an anode compartment on the outside of the anode and a cathode compartment on the outside of the cathode. The reactor of the present invention can be used for producing various chemical compounds which are useful in the chemical industry. The present invention is also concerned with a method for producing a chemical compound by performing an oxidation reaction, using the reactor of the present invention. The reactor of the present invention can be applied to various oxidation reactions, and is especially useful for performing selective oxidation reactions, for example, partial oxidation of an alkane, partial oxidation of an alcohol, epoxidation of an olefin, hydroxylation of an aromatic compound, partial oxidation of an amine and partial oxidation of a ketone. By using the reactor of the present invention, various chemical compounds having high values added thereto can be produced directly from a low-priced oxidant (such as oxygen), a reductant and a substrate, without using an expensive oxidizing agent, such as hydrogen peroxide or an organic or an inorganic peroxide. The reactor of the present invention is also applicable to various oxidative addition reactions, for example, a carbonylation reaction of an alcohol, a phenolic compound or an olefin; the Wacker reaction of an olefin; an acetoxylation reaction, oxychlorination reaction or coupling reaction of an olefin or an aromatic compound; and an esterification reaction of an alcohol. The reactor enables efficient and stable production of useful chemical compounds. For example, by using the reactor of the present invention, t-butylhydroperoxide can be synthesized in a single step by a selective oxidation reaction, from oxygen, t-butanol and hydrogen. t-Butyl-hydroperoxide is a useful chemical compound which is used as an oxidizing agent, a polymerization initiator, a curing agent and a desiccant in the chemical, pharmaceutical and food industries and the like.
2. Prior Art
Conventionally, oxidation reactions which are well known in the industry, especially a selective oxidation reaction and an oxidative addition reaction, have been carried out by employing the techniques as described below.
Useful chemical compounds can be efficiently produced under moderate conditions with high selectivity by performing a selective oxidation reaction, using an oxidizing agent (such as hydrogen peroxide or an organic or an inorganic peroxide) which can produce an active oxygen species (an electrophilic oxygen species) having high chemical potential (see, for example, “Shin Jikken Kagaku Koza 15, Sanka to Kangen I-2 (New Lecture on Experimental Chemistry 15, Oxidation and Reduction, I-2)”, edited by Japan Chemical Society, p. 605, 1976, Japan; and “Catalytic Oxidations with Hydrogen Peroxide as Oxidant”, G. Strukul, Kluwer Academic Publishers, 1992, the Netherlands). Examples of selective oxidation reactions include oxidation of an alkane, oxidation of an alcohol, epoxidation of an olefin, oxidation or ammoximation of a ketone, oxidation of an aldehyde, oxidation of an ether, hydroxylation of an aromatic compound, oxidation of an amine and oxidation of a sulfur compound.
The “selective oxidation reaction” mentioned herein means a reaction which proceeds in the presence of an electrophilic oxygen species, such as the selective oxidation reactions mentioned in the above-mentioned documents.
On the other hand, it is well known that, as a conventional method for producing hydrogen peroxide, which is a useful oxidizing agent as mentioned above, an autoxidation reaction using alkylanthraquinone is commercially used (see “Kagaku Binran, Oyo-kagaku-hen I (Chemical Handbook, Applied Chemistry I)”, edited by Japan Chemical Society, p. 302, 1986, Japan). However, the conventional method for producing hydrogen peroxide is economically disadvantageous not only in that the method requires a large amount of an organic solvent and but also in that, due to the generation of various by-products and degradation of a catalyst, the method requires various additional steps for separation of by-products and for regeneration of the degraded catalyst. Therefore, it has been desired to develop a production method by which hydrogen peroxide can be produced at a low cost, as compared to the case of the conventional method.
In addition, as a useful organic peroxide, t-butylhydroperoxide is also known. Conventionally, t-butylhydroperoxide has been produced, for example, by a method in which t-butanol or isobutylene as a substrate, namely a raw material, is reacted with a strong acid, such as sulfuric acid, and hydrogen peroxide (see, for example, “Yuki-Kasankabutsu (Organic Peroxides)”, edited by the Organic Peroxide Research Group, p. 220, 1972, Japan). However, the conventional method is disadvantageous from the viewpoint of economy and safety; specifically, the conventional method has disadvantages in that hydrogen peroxide (which is expensive) is necessary, and the raw material is reacted with a liquid mixture of a high concentration aqueous sulfuric acid (60 to 70 wt %) and a high concentration aqueous hydrogen peroxide (30 to 50 wt %).
For these reasons, from the practical and commercial viewpoint, it has been desired to develop a method by which various types of selective oxidation reactions can be performed by directly oxidizing a substrate with oxygen in the presence of a catalyst without using an expensive oxidizing agent, such as hydrogen peroxide. For example, a method for producing phenol directly from benzene and oxygen in the presence of a catalyst has long been studied. However, the reaction method which has been studied has the following problems. First, a high temperature is necessary for the reaction. Further, although various types of catalysts can catalyze the reaction, many of such catalysts pose a problem in that the reaction system containing such catalysts causes phenol as a reaction product to have higher reactivity than benzene as a substrate, so that, although the reaction rate of benzene can be increased, the selectivity for phenol is decreased. Thus, no method which is commercially employable has been developed. With respect not only to such reaction system (which causes phenol as a reaction product to have higher reactivity than benzene) but also to other oxidation reactions using oxygen, great efforts have been made for increasing the selectivity for a desired reaction product. However, there is no method which is satisfactory from the viewpoint of economy and safety. It is considered that the reason why such an oxidation reaction using oxygen does not proceed with high selectivity for a desired product is because, when oxygen molecules are activated by a catalyst, an electron transfer from the catalyst to the oxygen molecules inevitably occurs, so that oxygen molecules are mainly converted to nucleophilic oxygen anion active species, making it difficult for an electrophilic addition reaction to proceed (see Catalysis Today, 45, 3-12, 1998, the U.S.A.).
In recent years, in order to alleviate the above-mentioned problems, studies on a new method have been made for synthesizi
Otsuka Kiyoshi
Suzuki Ken
Yamanaka Ichiro
Asahi Kasei Kabushiki Kaisha
Wong Edna
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