Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-02-07
2002-11-12
Trinh, Ba K. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S531000, C210S294000, C210S322000
Reexamination Certificate
active
06479680
ABSTRACT:
The present invention relates to a process for the reaction of an organic compound with a hydroperoxide, during the course of which hydroperoxide is separated off and reacted again with the organic compound. The present invention likewise relates to an apparatus for the reaction of an organic compound with a hydroperoxide.
Reactions of organic compounds with hydroperoxides, i.e. with compounds of the formula ROOH, are generally carried out in one step in customary processes of the prior art.
In this context, the term “in one step” relates to the hydroperoxide starting material and means that hydroperoxide is added to the respective organic compound only in a single step during the overall process.
For example, U.S. Pat. No. 5,262,550 describes a process for the epoxidation of alkenes, in which alkene is reacted with hydrogen peroxide or a hydrogen peroxide precursor in one step 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, pp. 6-1 to 6-27, SRI International (1994), describes, for example, a process in which an about 17% strength by weight ethylbenzene hydroperoxide solution is reacted with propene in one step over a homogeneous Mo catalyst. A total of 7.2 mol of propene are used per mole of hydroperoxide in this process.
The same document discloses, on pages 6-28 to 6-47, a process in which an about 20% strength by weight ethylbenzene hydroperoxide solution is reacted with propene in one step over a heterogeneous TiO/SiO
2
catalyst, with the alkene being epoxidized. Here, 16.7 mol of propene are used per mole of hydroperoxide.
This document likewise discloses, on pages 5-1 to 5-21, a process in which an about 40% strength by weight tert-butyl hydroperoxide solution is reacted with propene in one step over a homogeneous Mo catalyst, with the alkene being epoxidized. Here, 3.7 mol of propene are used per mole of hydroperoxide.
The same document discloses, on pages 5-22 to 5-43, a process in which an about 72% strength by weight tert-butyl hydroperoxide solution is reacted with propene over a homogeneous Mo catalyst in two directly successive steps, with the alkene being epoxidized. Here, 1.2 mol of propene are used per mole of hydroperoxide.
A disadvantage of these processes is that it is necessary either to employ a relatively high excess of the organic compound to be reacted or to employ a very concentrated hydroperoxide in order to achieve optimal selectivity.
It is an object of the present invention to provide a process which allows the excess of organic compound to be reacted to be kept as low as possible and a relatively low-concentration hydroperoxide to be used.
We have found that this object is achieved by a process for the reaction of an organic compound with a hydroperoxide, which comprises at least the steps (i) to (iii) below:
(i) reaction of the hydroperoxide with the organic compound to give a mixture comprising the reacted organic compound and unreacted hydroperoxide,
(ii) separation of the unreacted hydroperoxide from the mixture resulting from step (i),
(iii) reaction of the hydroperoxide separated off in step (ii) with the organic compound.
Accordingly, the reaction of the organic compound with the hydroperoxide takes place in at least two steps (i) and (iii). In the process of the present invention, it is likewise conceivable for the reaction of the organic compound with the hydroperoxide to take place in more than two steps. Depending on the number of steps in which the reaction takes place, it is of course also conceivable for more than one step in which the hydrogen peroxide used is separated off to be employed in the process of the present invention.
An example which may be mentioned is a process in which the reaction of the organic compound with the hydroperoxide takes place in steps (i), (iii) and (v), and the separation of the hydroperoxide takes place in steps (ii) and (iv).
In general, from two to five steps in which the organic compound is reacted with the hydroperoxide are employed in the process of the present invention. The present invention therefore also provides a process for the reaction of an organic compound with a hydroperoxide, which comprises the steps (i) to (ix) below:
(i) reaction of the hydroperoxide with the organic compound to give a mixture M
I
,
(ii) separation of the hydroperoxide from the mixture M
I
resulting from step (i),
(iii) reaction of the hydroperoxide separated off in step (ii) with the organic compound to give a mixture M
II
,
(iv) separation of the hydroperoxide from the mixture M
II
resulting from step (iii),
(v) reaction of the hydroperoxide separated off in step (iv) with the organic compound to give a mixture M
III
,
(vi) separation of the hydroperoxide from the mixture M
III
resulting from step (v),
(vii) reaction of the hydroperoxide separated off in step (vi) with the organic compound to give a mixture M
IV
,
(viii) separation of the hydroperoxide from the mixture M
IV
resulting from step (vii),
(ix) reaction of the hydroperoxide separated off in step (viii) with the organic compound.
The process of the present invention preferably has from two to four steps in which the organic compound is reacted with hydroperoxide, particularly preferably from two to three steps. The reaction of the organic compound with the hydroperoxide preferably takes place in two steps.
The separation of the hydroperoxide in the abovementioned separation steps (ii), (iv), (vi) and (viii) in the process of the present invention can be carried out by all customary methods of the prior art. It is also possible to use different separation methods in different separation steps.
The separation of the hydroperoxide in the separation steps is preferably carried out by distillation. Depending on the requirements of the process, separation in one or more distillation columns is possible. Preference is given to using one distillation columns for separating off the hydroperoxide in one separation step.
In the process of the present invention, it is conceivable for a dedicated separation apparatus A
i
to be provided for each step in which the hydroperoxide is separated off. It is likewise possible, in the case of an appropriate reaction procedure and a plurality of separation steps, for the separations to be carried out in a single separation apparatus.
If a plurality of separation steps are provided, it is also possible, by means of a suitable reaction procedure, to carry out two or more separation steps in one separation apparatus. Accordingly, it is quite generally possible for a total of m separation apparatuses to be provided for n separation steps, where 1≦m≦n.
Should a further separation of the hydroperoxide be desired subsequent to the last stage in which reaction of the organic compound with the hydroperoxide takes place, for example to recycle any residual hydroperoxide, this is of course likewise possible within the scope of the process of the present invention.
In the process of the present invention, not only the hydroperoxide but also the reacted organic compound can be separated off in a separation apparatus from the mixture resulting from a reaction step in which the organic compound is reacted with the hydroperoxide. It is naturally also possible for the remaining reaction product after the hydroperoxide has been separated off to be transferred to a further separation apparatus provided specifically for this purpose and the reacted organic compound to be separated from the reaction product there.
In both cases, it is possible, for example, to collect the reacted organic compound in the m separation apparatuses and to separate it off after the reactions of the organic compound with the hydroperoxide are complete.
However, the reacted organic compound is preferably separated off in addition to the hydroperoxide in the respective separation apparatus. In the case of separation by distillation, it is possible, for example, to take
Bassler Peter
Harder Wolfgang
Resch Peter
Rieber Norbert
Ruppel Wilhelm
BASF - Aktiengesellschaft
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
Trinh Ba K.
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