Method for converting an organic compound with a hydroperoxide

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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Reexamination Certificate

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06727371

ABSTRACT:

FIELD OF INVENTION
The present invention relates to a process for reacting an organic compound with a hydroperoxide using at least two reactors connected in parallel. The invention further provides the apparatus itself in which the process is carried out, and quite generally provides for the use of this apparatus for carrying out the process.
BACKGROUND INFORMATION
Reactions of organic compounds with hydroperoxides, i.e. compounds of the formula ROOH, are generally carried out in a single stage in customary processes of the prior art.
For example, U.S. Pat. No. 5,262,550 describes a process for the epoxidation of alkenes in which alkene is reacted in one step with hydrogen peroxide or a hydrogen peroxide precursor to give the corresponding alkene oxide.
U.S. Pat. No. 4,883,260 discloses a process in which alkene is reacted with hydrogen peroxide in one step in a steel autoclave or in a glass autoclave.
S. H. Wang, Process Economics Program, Report 2E, p. 6-1 to 6-27, SRI International (1994), for example, describes a process in which an about 17% strength by weight solution of ethylbenzene hydroperoxide is reacted with propene in a single step over a homogeneous Mo catalyst.
The same document discloses, on pages 6-28 to 6-47, a process in which an about 20% strength by weight solution of ethylbenzene hydroperoxide is reacted with propene in a single step over a heterogeneous Ti/SiO
2
catalyst, with the alkene being epoxidized.
This document likewise discloses, on pages 51 to 521, a process in which an about 40% strength by weight solution of tert-butyl hydroperoxide is reacted with propene in a single step over a homogeneous Mo catalyst, with the alkene being epoxidized.
Two-stage processes are also known from the prior art.
For example, the abovementioned SRI publication discloses, on pages 522 to 543, a process in which an about 72% strength by weight solution of tert-butyl hydroperoxide is reacted with propene over a homogeneous Mo catalyst in two directly successive stages, with the alkene being epoxidized.
U.S. Pat. No. 5,849,937 describes a process for the epoxidation of an olefin using a cascade of at least two fixed-bed reactors connected in series.
BRIEF SUMMARY
It is an object of the present invention to provide a process which allows a high throughput of feed streams and is, in particular, configured so that regeneration of catalysts used in the reaction of the organic compound with hydroperoxide can also be carried out in a simple way.
DETAILED DESCRIPTION OF THE INVENTION
We have found that this object is achieved by a continuous process for reacting an organic compound with hydroperoxide in the presence of a catalyst, wherein the reaction is carried out in a reactor assembly comprising at least two reactors connected in parallel.
Both single-stage and also two-stage and multistage processes are conceivable for carrying out the reaction. If multistage process configurations are chosen, it has to be ensured that at least one of the stages has at least one reactor assembly comprising at least two reactors connected in parallel.
For example, it is conceivable for the process to have a reaction stage (R1) in which the organic compound is reacted in the presence of a catalyst to give a product stream (P1), with a reactor assembly comprising two or more reactors connected in parallel being selected for reaction stage (R1). Likewise, (R1) can have a reactor assembly comprising at least two reactor cascades connected in parallel, with each reactor cascade having at least two reactors connected in series. It is also conceivable to have reactor assemblies in which at least one such reactor cascade is connected in parallel to at least one further reactor.
Apart from the reaction stage or stages, the process of the present invention can further comprise at least one intermediate treatment in which at least one product stream resulting from at least one reaction stage is treated in an appropriate manner.
For example, it is conceivable for the process to have a reaction stage (R1) as described above in which the organic compound is reacted in the presence of a catalyst to give a product stream (P1) and the product stream is passed to an intermediate treatment (I1). The product stream (PI1) resulting from the intermediate treatment (I1) can, for example, be recirculated to the reaction stage (R1) in order, for example, to react unreacted organic compound or/and unreacted hydroperoxide. Likewise, the product stream (PI1) can be fed to a further reaction stage (R2). It is also possible, for example, for the product stream (PI1) to be divided in an appropriate manner into at least two substreams and at least one of the substreams to be recirculated to (R1) and at least one of the substreams to be passed to the reaction stage (R2).
In principle, any desired reaction which can be carried out using the product stream (PI1) or the substream or substreams of (PI1) can be performed in (R2). In the process of the present invention, preference is given to feeding the product stream (PI1) comprising hydroperoxide to the reaction stage (R2) and reacting hydroperoxide with the organic compound in the presence of a catalyst in (R2) to give a product stream (P2).
The present invention accordingly provides a continuous process, as described above, for reacting an organic compound with hydroperoxide, in which
the organic compound is reacted with hydroperoxide in the presence of a catalyst in a reaction stage (R1) to give at least one product stream (P1),
the product stream or streams (P1) is passed to an intermediate treatment (I1) to give, as output from (I1), at least one product stream (PI1) comprising hydroperoxide, and
the product stream or streams (PI1) is passed to a reaction stage (R2) in which hydroperoxide is reacted with the organic compound in the presence of a catalyst to give at least one product stream (P2),
wherein at least two reactors connected in parallel are used in at least one of the reaction stages (R1) and (R2).
The present invention thus encompasses embodiments in which, for example, two or more reactors connected in parallel are used in the reaction stage (R1) and one reactor is used in the reaction stage (R2). It likewise encompasses embodiments in which one reactor is used in reaction stage (R1) and two or more reactors connected in parallel are used in reaction stage (R2). Furthermore, it also encompasses embodiments in which two or more reactors connected in parallel are used in reaction stage (R1) and two or more reactors connected in parallel are used in stage (R2), where the number of parallel reactors used in stage (R1) can be identical to or different from the number of parallel reactors used in stage (R2).
The number of feed streams which are introduced into the reactor or reactors in (R1) can essentially be chosen without restriction. All starting materials can, for example, be introduced as individual streams into the reactor or reactors. Likewise, the feed streams can be combined in an appropriate manner before introduction into the reactor or reactors and the resulting stream or streams can be introduced into the reactor or reactors. For example, it is conceivable for a reactor of (R1) to be fed with a feed stream which already has the composition of the mixture which is reacted in the reactor.
Quite generally, the feed stream or streams can be pretreated before it is introduced into a reactor of stage (R1). All methods are conceivable for this pretreatment. For example, at least one basic compound, at least one neutral compound, at least one acidic compound or a mixture of two or more of these compounds can be added to one or more feed streams used in (R1), with preference being given to adding a basic compound as is discussed below in respect of the intermediate treatment (I1).
Depending on the number of reactors used in stage (R1), stage (R1) results in a differing number of product streams which are passed to the intermediate treatment (I1). For example, it is conceivable for a product stream from (R1) to be divided in an appropriate manner into a plu

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