Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2000-03-01
2001-04-24
Geist, Gary (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
Reexamination Certificate
active
06222061
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a novel norbornene carboxylate compound and a method of producing the same, and more particularly, to 2-alkyl-2-adamantyl 5-norbornene-2-carboxylates and a method of producing the same.
2. Description of the Related Art
Norbornene, which is a common name for bicyclo[2.2.1]-2-heptene, is an alicyclic hydrocarbon compound and is widely used in various chemical reactions due to high reactivity of cyclo-double bonds. Specifically, in a norbornene carboxylate compound having a carboxyl group introduced to norbornene, the norbornene can be easily replaced by a bulky substituent. In particular, a bulky substituent containing an alicyclic compound which has low chemical reactivity is in wide use commercially.
Norbornene compounds having a bulky alicylic substitute are commercially used as various flame retardants. Furthermore, the norbornene compound having a bulky alicyclic substituent is capable of copolymerizing with existing monomers to then be used as a polymer flame retardant. Thus, much attention is being paid to the production of norbornene compounds having a bulky alicyclic substituent.
However, conventional norbornene carboxylate compounds having a bulky alicyclic substituent are cumbersome in view of reaction conditions, resulting in poor yield, and the purification thereof is difficult. Thus, it is quite difficult to produce the conventional norbornene carboxylate compounds on a commercial scale.
SUMMARY OF THE INVENTION
To solve the above problems, it is an object of the present invention to provide a norbornene carboxylate compound which can be produced and purified by a simplified process to be suitable for commercial-scale production.
It is another object of the present invention to provide a method for producing the norbornene carboxylate compound.
Accordingly, to achieve the first object, there is provided 2-alkyl-2-adamantyl 5-norbornene-2-carboxylate represented by formula (1):
wherein R is methyl or ethyl.
To achieve the second objective, there is provided a method of producing the compound recited in claim
1
, including the steps of a) synthesizing 2-alkyl-2-adamantanol having an alkyl group at its own 2-position by reacting 2-adamantanone with either an alkyl Grignard reagent or an alkyl lithium reagent, b) synthesizing 2-alkyl-2-adamantyl acrylate by reacting the 2-alkyl-2-adamantanol synthesized in the step a) with acryloyl chloride, and c) applying the 2-alkyl-2-adamantyl acrylate synthesized in the step b) and cyclopentadiene to Diels-Alder reaction.
Preferably, the Grignard reagent is either alkyl magnesium bromide or alkyl magnesium chloride.
More preferably, if the alkyl is methyl, either methyl magnesium bromide or methyl magnesium chloride is used as the Grignard reagent, and if the alkyl is ethyl, ethyl lithium reagent is used.
In the production method of the norbornene compound according to the present invention, a separation process may be performed after each step is completed. However, the separation process may be performed after all steps are performed in situ.
BRIEF DESCRIPTION OF THE DRAWINGS
REFERENCES:
patent: 4200588 (1980-04-01), Lednicer et al.
patent: 6147249 (2000-11-01), Watanabe et al.
patent: 6153785 (2000-11-01), Jung et al.
Chem Search Corp.
Geist Gary
Reed Smith Hazel & Thomas LLP
Reyes Hector M.
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