Organic compounds -- part of the class 532-570 series – Organic compounds – Halogen containing
Patent
1997-05-05
1999-02-02
Mach, D. Margaret M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Halogen containing
570249, 570250, C07C 1708, C07C 1720
Patent
active
058667318
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP95/02292, filed 9 Nov. 1995.
TECHNICAL FIELD
This invention relates to a halogenated organic compound which is useful as a raw material for the production of pharmaceuticals, pesticides and functional polymers.
BACKGROUND ART
The processes for preparing a brominated hydrocarbon by adding hydrogen bromide to an alkene compound or an alkyne compound are classified into two types. The first type is a process for introducing a bromine atom to a molecular terminal by a free radical reaction effected by using a free radical initiator such as a peroxide, ultraviolet light, molecular oxygen, a metal such as iron, cobalt or nickel, or .alpha.-halo-ketone. The second type is a process for introducing a bromine atom into the inside of a molecule by an ionic reaction effected by using an ionic reaction source such as an ionic phase transfer catalyst, for example, a quaternary Experimental Chemistry!, p418; and J. Org. Chem., vol. 45, No. 17, 3527-3529 (1980)) and silica gel (Kagaku to Kogyo (Chem. and Ind.) vol. 45, No. 4, 134 (1992).
The first type process generally has a problem in that a radical source has poor handling properties. The second type process generally has a problem in that an ionic source is troublesome to make and the production is costly.
DISCLOSURE OF INVENTION
An object of the invention is to provide a process for producing a halogenated organic compound by an addition reaction of a hydrogen halide to an organic compound having a carbon-carbon unsaturated bond, wherein a catalyst is used which has a good handling property and is inexpensive and readily available.
In accordance with the present invention, there is provided a process for producing a halogenated organic compound wherein a hydrogen halide is added to an organic compound having an aliphatic carbon-carbon unsaturated bond, as a substrate, characterized by using as a catalyst 0.0001 to 50% by weight, based on the weight of the organic compound having an aliphatic carbon-carbon unsaturated bond, of an organic compound having at least two polar groups in the molecule each containing a heteroatom having an unshared electron pair, and having no aliphatic carbon-carbon unsaturated bond.
PREFERRED EMBODIMENTS FOR CARRYING OUT THE INVENTION
The substrate used in the hydrogen halide addition reaction of the present invention is not particularly limited provided that it is an organic compound having at least one aliphatic carbon-carbon unsaturated bond in the molecule. As the substrate, there can be mentioned generally alkenes and alkynes. The alkenes and alkynes are represented by the following formulae (1) and (2), respectively: ##STR1##
In the above formulae, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 may be the same or different, and are selected from a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aralkyl group, a phenoxy group, a halogen atom, a hydroxyl group, a carboxyl group and a nitro group, and R.sup.1 and R.sup.3 in formula (1) may form a ring and R.sup.5 and R.sup.6 in formula (2) may form a ring, together with the carbon atoms of the carbon-carbon unsaturated bond.
The number of carbon atoms in each of the alkyl, alkoxy, aryl, aralkyl and phenoxy groups is not particularly limited, but is usually in the range of 1 to 20, preferably 1 to 15 and more preferably 1 to 10. In the case where R.sup.1 and R.sup.3 in formula (1) form a ring and R.sup.5 and R.sup.6 in formula (2) form a ring, together with the carbon atoms of the carbon-carbon unsaturated bond, each of the rings is usually a 4-membered to 20-membered ring, preferably 4-membered to 10-membered ring and more preferably 5-membered or 6-membered ring.
The alkyl, alkoxy, aryl, aralkyl and phenoxy groups may have a substituent or substituents. The substituents are not particularly limited unless the substituents have baneful effects on the halogenation reaction.
The number of carbon atoms in each of the alkenes and alkynes is not particularly limited and is usually in the range of 2 to 30, preferably 3
REFERENCES:
patent: 5744663 (1998-04-01), Landscheidt
CASREACT #113:190788, abstract of Kropp, J. Am. Chem. Soc., (1990, vol. 112(20), pp. 7433-7434, 1990.
Jikken Kagaku Koza (Lectures on Experimental Chemistry) 20, pp. 193-195,
Shin Jikken Kagaku Koza (Lectures on New Experimental Chemistry) 14, pp. enclosed), 1958.
J. Org. Chem. 1994, 59 pp. 3102-3112, Surface-Mediated Reactions. 4. Hydrohalogenation of Alkynes, by Paul J. Kropp, et al.
J. Org. Chem. 1980, 45 pp. 3527-2529, Addition of Hydrohalogenic Acids to Alkenes in Aqueous-Organic, Two-Phase Systems in the Presence of Catalytic Amounts of Onium Salts, by Dario Landini, et al.
Matsuura Tomoo
Watanabe Kiyoshi
M. Mach D. Margaret
Nippon Zeon Co. Ltd.
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