Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1986-07-03
1987-12-15
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
514533, C07C 6976
Patent
active
047134747
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD AND DISCLOSURE OF THE INVENTON
This invention relates to novel alkanedicarboxylic diester compounds represented by the formula: ##STR2## wherein n is an integer of 0.about.8 and R is benzyl group or alkyl group having 3.about.8 carbon atoms.
The compounds are useful as pest-repellants and plasticizers.
The present inventors have prepared various types of new compounds in order to develop compounds having pest-repellancy action and increasing plasticization efficiency to a thermoplastic polymer, and then have discovered such compounds.
This invention has been accomplished based on these findings.
This invention relates to alkanedicarboxylic diester compounds represented by the formula: ##STR3## wherein n is an integer of 0.about.8 and R is benzyl group or alkyl group having 3.about.8 carbon atoms.
The compounds of this invention can be readily prepared by reacting, for example, alkanedicarboxylic acid dichloride represented by the formula: ##STR4## wherein n is an integer of 0.about.8, with alkyl p-hydroxybenzoate or benzyl p-hydroxybenzoate in a suitable solvent such as toluene, benzene, chloroform, dichloroethane in the presence of an amine such as triethylamine, pyridine, dimethylaniline.
The resulting compound is purified by a conventional method such as column chromatography, recrystallization by methanol, DMF, acetonitrile, etc.
In using the compound of this invention as a pest-repellant, it is mixed with a conventional carrier for a pest-repellant, kneaded in a synthetic resin, e.g. polyvinyl chloride or any other material intended for repellency of vermin, coated or impregnated with a brush or by spraying.
The amount in which the compound is used varies depending on the mode of use and is such that is enough to exhibit a repellency action to vermin. For example, 0.5 to 10 parts by weight of it may be compounded to 1 part by weight of a carrier.
Further, the compounds of this invention impart a superior plasticization efficiency to a thermoplastic polymer and increase its suppleness, elasticity, plasticity with a low volatility. Hence they are useful as a plasticizer for polymers.
EXAMPLE 1
Into a 300 ml four-neck flask equipped with a dropping funnel, a calcium chloride tube and a thermometer are charged 16.6 g of ethyl p-hydroxybenzoate, 7.9 g of pyridine and 150 ml of ethylether. A solution of 9.2 g of adipic acid dichloride in 20 ml of ethylether is added dropwise to the mixture with stirring while retaining the mixture at 0.degree.-5.degree. C. over 30 minutes. After addition, the mixture is further allowed to react at 0.degree.-5.degree. C. for 1 hour. Thereafter, the ethylether from the resulting reaction product is distilled and subsequently, recrystallized from methanol to give di(p-ethyloxycarbonylphenyl) adipate melting at 82.degree.-83.degree. C. as white crystals.
EXAMPLE 2
A similar procedure to Example 1 is carried out by using 16.6 g of ethyl p-hydroxybenzoate and 8.5 g of glutaric acid dichloride to yield di(p-ethyloxycarbonylphenyl)glutarate, m.p. 81.degree.-82.degree. C., as white crystals.
EXAMPLE 3
A similar procedure to Example 1 is carried out by using 7.8 g of propyl p-hydroxybenzoate and 18 g of succinic acid dichloride to yield di(p-propyloxycarbonylphenyl)succinate, m.p 122.degree.-123.5.degree. C., as white crystals.
EXAMPLE 4
A similar procedure to Example 1 is carried out by using 18 g of propyl p-hydroxybenzoate and 8.5 g of glutaric acid dichloride to yield di(p-propyloxycarbonylphenyl)glutarate, m.p. 74.degree.-75.degree. C., as white crystals.
EXAMPLE 5
A similar procedure to Example 1 is carried out by using 15.2 g of methyl p-hydroxybenzoate and 7.8 g of succinic dichloride to yield di(p-methyloxycarbonylphenyl)succinate, m.p. 189.5.degree.-190.degree. C., as white crystals.
EXAMPLE 6
A similar procedure to Example 1 is carried out by using 15.2 g of methyl p-hydroxybenzoate and 12 g of sebacic acid dichloride to yield di(p-methyloxycarbonylphenyl)sebacate, m.p. 109.5.degree.-110.5.degree. C., as white crystals.
EXAMPLE 7
A sim
REFERENCES:
C. A., 93(6):47827k, 1980.
C. A., 97(16):128211g, 1982.
C. A., 93(24):221373w, 1980.
Chemical Abstracts, vol. 84(9), 58848h, (1976).
Akashi Hiroyuki
Horie Shoichi
Inoue Takeshi
Killos Paul J.
Yoshitomi Pharmaceutical Industries Ltd.
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