Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2000-03-29
2001-09-11
Shippen, Michael L. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C560S266000, C549S514000
Reexamination Certificate
active
06288285
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a process for the production of dichloroacetoxypropane and derivatives thereof which are raw materials for useful organic products.
2. Description of the Related Art
The term “dichloroacetoxypropane” as used herein refers to 2,3-dichloro-1-acetoxypropane, 1,3-dichloro-2-acetoxypropane or a mixture thereof. Further, the term “dichloropropanol”, as used herein refers to 2,3-dichloro-1-propanol, 1,3-dichloro-2-propanol or a mixture thereof.
A process for producing dichloroacetoxypropane by reacting allyl acetate with chlorine in a liquid phase is described, for example, in
Khim. Prom
., No. 5, 277-280 (1981),
Khim. Prom
., No. 6, 328-335 (1982) and Japanese Examined Patent Publication (Kokoku) No. 52-16091. The reaction is represented by the following formula.
These conventional techniques all relate to the reaction in a liquid phase and use a metal salt such as a metal halide as a catalyst. However, when a metal salt is used as a catalyst, the catalyst must be separated and recovered after the reaction. Moreover, the metal salt dissolves into the reaction solution and the separation and recovery of the dissolved metal salt presents another problem. In order to prevent the metal salt dissolving, Japanese Examined Patent Publication No. 52-16091 proposes a supported catalyst in which a metal salt is supported on a support. However, it is still difficult to prevent the metal salt dissolving out of the support.
Furthermore, in all the above-described conventional techniques, the reaction of allyl acetate with chlorine is effected in the presence of an organic solvent. The use of an organic solvent has, however, a problem in that a recovery step therefor is necessary or loss of the organic solvent is caused at the time of recovery.
There is still another problem in that since the production of dichloroacetoxypropane by the reaction of allyl acetate with chlorine is an exothermic reaction, external cooling or the like is necessary in order to obtain dichloroacetoxypropane with high efficiency and this causes a loss of energy.
As a conventional technique for chlorination in a gaseous phase, a reaction of ethylene with chlorine is known (see, for example, U.S. Pat. No. 2,099,231). However, a method of producing dichloroacetoxypropane by reacting allyl acetate with chlorine in a gaseous phase has not hitherto been reported.
BRIEF SUMMARY OF THE INVENTION
An object of the present invention is to overcome the defects of the liquid phase processes conventionally employed for the production of dichloroacetoxypropane, more specifically, problems such as the necessity of a step for separating and recovering a catalyst, the necessity of a step for recovering an organic solvent resulting from use of an organic solvent, the loss of the organic solvent during recovery or the loss of energy accompanying external cooling, and to provide an industrially more advantageous production process for dichloroacetoxypropane as well as an industrially more advantageous production process for a derivative of dichloroacetoxypropane, such as dichloropropanol or epichlorohydrin, using the above-described process.
As a result of extensive investigations to solve the above-described problems, the present inventors have found that the object of the present invention can be attained by a process for producing dichloroacetoxypropane, comprising reacting allyl acetate with chlorine in a gaseous phase in the presence of a catalyst comprising an element of Group 16 of the long-form Periodic Table or in the absence of a catalyst. The present invention has been accomplished based on this finding. In other words, the present invention provides a process for producing dichloroacetoxypropane, comprising reacting allyl acetate with chlorine in a gaseous phase in the presence of a catalyst comprising an element of Group 16 of the long-form Periodic Table or in the absence of a catalyst.
The present invention also provides a process for efficiently producing dichloroacetoxypropane by reacting allyl acetate with chlorine in a gaseous phase and then efficiently producing a derivative thereof, for example, a process for efficiently producing dichloropropanol from the resulting dichloroacetoxypropane and a process for further producing epichlorohydrin in good efficiency.
DETAILED DESCRIPTION OF THE INVENTION
The present invention is described in detail below.
Allyl acetate for use in the present invention may be any commercially or industrially available allyl acetate and is not particularly limited.
Chlorine for use in the present invention may be any commercially or industrially available chlorine and is not particularly limited.
The catalyst for use in the production of dichloroacetoxypropane according to the present invention is a catalyst containing an element of Group 16 of the long-form Periodic Table, preferably Te. The element may be in the form of a compound containing the element.
Specific examples of the compound include halides, oxides, carbonates, phosphates, nitrates, sulfates, oxyhalides, basic carbonates, hydroxides, carboxylates and organic metal complexes of the above-described elements, however, the present invention is by no means limited thereto. Of these, halides and oxides are preferred.
Examples of the halogen of the halides or oxyhalides include fluorine, chlorine, bromine and iodine. Of these, chlorine is preferred.
The catalyst can be used in any known form and is not particularly limited. The catalyst is preferably a support type, a coprecipitation type or an ion exchange type, more preferably a support type.
The element of Group 16 of the long-form Periodic Table to be used for the catalyst in the present invention may suitably have a concentration of from 0.01 to 100 wt %, preferably from 0.1 to 50 wt %, based on the total weight of the catalyst.
In the case of a supported catalyst, specific examples of the support include single oxides such as alumina, zirconia, titania, niobia, silica and magnesia, complex oxides such as silica alumina, and zeolite, heteropolyacids, activated carbon and polymers, but the support is not particularly limited thereto.
The supported catalyst can be prepared by a known process, for example, a process for impregnating a metal compound into a support. More specifically, for supporting a metal compound on a support, the metal compound is dissolved in an appropriate solvent such as water, alcohol, hydrochloric acid or aqueous ammonia, in an amount such that the support can absorb the solution. To the resulting solution, a support having an appropriate particle size is added and, after being impregnated with the solution, the support is dried. The drying may be performed either under normal pressure or a reduced pressure. For example, in the case of drying the catalyst under a reduced pressure, the drying may be performed in a vacuum dryer at from 20 to 300° C. The drying is preferably continued until the catalyst reaches a constant weight.
The dried supported catalyst may be used as it is in the reaction or may be calcined before use. The calcination may be performed in an atmosphere of nitrogen, carbon dioxide, air, oxygen, hydrogen or the like, however, the atmosphere is not particularly limited as far as it matches the purpose.
The catalyst containing an element of Group 16 of the long-form Periodic Table may be prepared by any known process. For example, the catalyst may be prepared by calcining and reducing a catalyst containing an element of Group 16 of the long-form Periodic Table in an atmosphere containing a reducing agent such as hydrogen, paraffin or olefin, however, the present invention is by no means limited thereto.
The calcination temperature is not particularly limited, however, it is preferably a temperature higher than the reaction temperature. The calcination time is also not particularly limited, but the calcination is preferably continued until the catalyst reaches a constant weight.
The catalyst used in the present invention may have any shape such as a tablet, a
Aoki Takanori
Ishikami Haruki
Ohe Takami
Shippen Michael L.
Showa Denko K.K.
Sughrue Mion Zinn Macpeak & Seas, PLLC
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