Chemistry of hydrocarbon compounds – Aromatic compound synthesis – Having alkenyl moiety – e.g. – styrene – etc.
Reexamination Certificate
2000-02-28
2001-10-09
Griffin, Walter D. (Department: 1764)
Chemistry of hydrocarbon compounds
Aromatic compound synthesis
Having alkenyl moiety, e.g., styrene, etc.
C585S436000, C585S443000, C585S444000, C585S445000
Reexamination Certificate
active
06300534
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a process for producing hydrocarbons, and more specifically, relates to a process for selectively producing (m-vinylphenyl)phenylmethane, 1-(m-vinylphenyl)-1-phenylethane, 1-(m-ethylphenyl)-1-phenylethylene, or 1-(m-vinylphenyl)-1-phenylethylene which is a useful compound as a synthetic raw material of &agr;-(m-benzoylphenyl)propionic acid (tradename: Ketoprofen) of a profen analgesic.
BACKGROUND ART
A mixture comprising an o-ethyldiphenylalkane and a m-ethyldiphenylalkane can be industrially produced in low cost utilizing an alkylation reaction, a disproportionation reaction, a condensation reaction and the like in the presence of an acid catalyst from a raw material such as an alkylbenzene.
Hereby, &agr;-(m-benzoylphenyl)propionic acid (tradename: Ketoprofen) of a profen analgesic is obtained by a reaction such as a carbonylation from 1-(m-vinylphenyl)-1-phenylethane in Japanese Patent Application Laid-open No. Hei 2-101041. In addition, &agr;-(m-benzoylphenyl)propionic acid of a profen analgesic is obtained from 1-(m-vinylphenyl)-1-phenylethylene in Japanese Patent Application Laid-open No. Hei 3-31221. Further, in U.S. Pat. No. 4,922,052 (m-vinylphenyl)phenylmethane or the like is produced using a Grignard reagent, and &agr;-(m-benzoylphenyl)propionic acid (tradename: Ketoprofen) of a profen analgesic is obtained therefrom.
Any of the processes for producing &agr;-(m-benzoylphenyl)propionic acid (tradename: Ketoprofen) of a profen analgesic from the above-mentioned 1-(m-vinylphenyl)-1-phenylethane, 1-(m-vinylphenyl)-1-phenylethylene, (m-vinylphenyl)phenylmethane is according to a cheap and simple process such as carbonylation or the like. Accordingly, it should be said that 1-(m-vinylphenyl)-1-phenylethane, 1-(m-vinylphenyl)-1-phenylethylene, (m-vinylphenyl)phenylmethane and the like are useful as a raw material for &agr;-(m-benzoylphenyl)propionic acid (tradename: Ketoprofen) of a profen analgesic.
Hereby, as already described, the mixture comprising the o-ethyldiphenylalkane and the m-ethyldiphenylalkane can be industrially produced in low cost utilizing an alkylation reaction, a disproportionation reaction, a condensation reaction and the like in the presence of an acid catalyst from an alkylbenzene and the like.
Therefore, if 1-(m-vinylphenyl)-1-phenylethane, 1-(m-vinylphenyl)-1-phenylethylene, (m-vinylphenyl)phenylmethane and the like can be obtained utilizing the mixture, it is industrially advantageous.
However, anethyldiphenylalkane is obtained as a mixture comprising an o-ethyldiphenylalkane, a m-ethyldiphenylalkane and a p-ethyldiphenylalkane by the process utilizing an alkylation reaction, a disproportionation reaction, a condensation reaction and the like in the presence of an acid catalyst from a raw material such as an alkylbenzene or the like.
The boiling points of o-, m- and p-(ethylphenyl)phenylmethane are 290.9° C., 291.5° C. and 297.0° respectively. In addition, the boiling points of o-, m- and p-1-(ethylphenyl)-1-phenylethane are 285° C., 284° C. and 293° C.
Accordingly, in case of a p-ethyldiphenylalkane, the p-ethyldiphenylalkane can be separated by a usual separation method of distillation from a mixture of ethyldiphenylalkanes containing thereof.
However, it is practically difficult to separate a m-ethyldiphenylalkane from a mixture comprising an o-ethyldiphenylalkane and a m-ethyldiphenylalkane by distillation. Therefore, it is considered the process of using the mixture comprising the above-mentioned o-ethyldiphenylalkane, m-ethyldiphenylalkane and p-ethyldiphenylalkane as a raw material is difficult to be industrially adopted. In fact, such proposal is not proposed yet.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide a process for selectively producing (m-vinylphenyl)phenylmethane, 1-(m-vinylphenyl)-1-phenylethane, 1-(m-ethylphenyl)-1-phenylethylene, or 1-(m-vinylphenyl)-1-phenylethylene which is a useful compound as a synthetic raw material of &agr;-(m-benzoylphenyl)propionic acid (tradename: Ketoprofen) of a profen analgesic, utilizing a mixture of an o-ethyldiphenylalkane and a m-ethyldiphenylalkane which are difficult to be separated by an industrial distillation and whose ingredients are difficult to be utilized, as a raw material.
Namely, the present invention is a process for producing hydrocarbons, wherein a mono-olefin hydrocarbon and/or a di-olefin hydrocarbon represented by the following general formula (3) is selectively produced by dehydrogenating or oxidative-dehydrogenating a mixture of any one of hydrocarbons among the hydrocarbons represented by the following general formula (1) and any one of hydrocarbons among the hydrocarbons represented by the following general formula (2), to be distilled.
and R
1
is a vinyl group or an ethyl group)
According to the process for producing hydrocarbons of the present invention, a mixture of an o-ethyldiphenylalkane and a m-ethyldiphenylalkane which are difficult to be separated by an industrial distillation and whose ingredients are difficult to be utilized as a mixture in the prior art can be used as a raw material. When a dehydrogenation reaction is carried out using the raw material, the o-ethyldiphenylalkane in the mixture is a cyclo-dehydrogenated compound having a higher boiling point than the dehydrogenating compound of the m-ethyldiphenylalkane, a solid cyclo-dehydrogenated compound, and a compound obtained by eliminating an ethyl group which was substituted at a phenyl group, i.e., a compound having a lower boiling point than the dehydrogenated compound of the m-ethyldiphenylalkane. Accordingly, the dehydrogenated compound of the o-ethyldiphenylalkane can be easily separated from the dehydrogenated compound of the m-ethyldiphenylalkane by usually distilling a mixture of the dehydrogenation reaction after reaction. As a result, the dehydrogenated compound of the m-ethyldiphenylalkane which is the objective product of the present invention can be easily obtained in high purity.
BEST MODE FOR CARRYING OUT THE INVENTION
The content of the present invention is illustrated in more detail below.
The hydrocarbon represented by the aforementioned general formula (1) is specifically (m-ethylphenyl)phenylmethane or 1-(m-ethylphenyl)-1-phenylethane.
The hydrocarbon represented by the aforementioned general formula (2) is specifically (o-ethylphenyl)phenylmethane or 1-(o-ethylphenyl)-1-phenylethane.
The mono-olefin hydrocarbon or the di-olefin hydrocarbon represented by the aforementioned general formula (3) is specifically (m-vinylphenyl)phenylmethane (mono-olefin hydrocarbon) obtained by dehydrogenating an ethyl group which is substituted at the m-position of a phenyl group of (m-ethylphenyl)phenylmethane, 1- (m-vinylphenyl) -1-phenylethane (mono-olefin hydrocarbon) obtained by dehydrogenating an ethyl group which is substituted at the m-position of a phenyl group of 1-(m-ethylphenyl)phenylethane, 1-(m-ethylphenyl)-1-phenylethylene (mono-olefin hydrocarbon) obtained by dehydrogenating an ethyl group to which two phenyl groups of 1-(m-ethylphenyl)-1-phenylethane are substituted, and 1-(m-vinylphenyl)-1-phenylethylene (di-olefin hydrocarbon) obtained by dehydrogenating both an ethyl group which is substituted at the m-position of a phenyl group of 1-(m-ethylphenyl)-1-phenylethane and an ethyl group to which two phenyl groups are substituted.
The dehydrogenated compound of an o-ethyldiphenylalkane is merely prepared by a dehydrogenation reaction of the o-ethyldiphenylalkane represented by the general formula (2), and the dehydrogenated compounds of the o-ethyldiphenylalkane are mainly a cyclo-dehydrogenated compound shown as described below and a compound from which an ethyl group substituted at a phenyl group is eliminated.
Namely, the cyclo-dehydrogenated compound prepared from the o-ethyldiphenylalkane is as follow.
1-Phenylindene and the like are prepared from (o-ethylphenyl)phenylmethane. 1-Phenylnaphthalene (boiling point: 324-325° C.), 9,10-dimethylanthracene (melting point: 182-184° C.), and 9-methylanth
Konishi Tomohiro
Suyama Kazuharu
Dang Thuan D.
Griffin Walter D.
Hollander Law Firm, P.L.C.
Nippon Petrochemicals Company Limited
LandOfFree
Process for producing dehydrogenated compounds of... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for producing dehydrogenated compounds of..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for producing dehydrogenated compounds of... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2565721