Alkenylphosphonic ester and preparation process thereof
AssigneeNational Institute of Advanced Industrial Science and Technology
InventorsLi-Biao Han, ChangQiu Zhao, Masato Tanaka
Life of this patent
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Abstract
Novel alkenylphosphonic acid esters of the following general formula (I): R1CH═CR2[P(O)(OCR3R4CR5R6O)] (I) and a simple process for the preparation thereof are provided by the use of secondary cyclic phosphonic acid esters as the starting material.
Claims9
(amended) An alkenylphosphonic acid ester compound of the following general formula (I):
- R1CH═CR2[P(O)(OCR3R4CR5R6O)] (I)
- wherein R1 and R2 each stand for a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, a heteroaryl group, an alkenyl group, an alkoxy group, an aryloxy group or a silyl group, provided that R1 does not stand for a hydrogen atom or a methyl group, and R3, R4, R5 and R6 each stand for a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group.
(amended) A process for the preparation of an alkenylphosphonic acid ester compound, comprising reacting an acetylene compound of the following formula (II):
- R1C≡CR2 (II)
- wherein R1 and R2 each stand for a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, a heteroaryl group, an alkenyl group, an alkoxy group, an aryloxy group or a silyl group, provided that R1 does not stand for a hydrogen atom or a methyl group, with a cyclic secondary phosphonic acid ester of the following formula (III):
- HP(O)(OCR3R4CR5R6O) (III)
- wherein R3, R4, R5 and R6 each stand for a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group, in the presence of a catalyst of a metal of Group 9 of the Periodic Table to obtain an alkenylphosphonic acid ester compound of the following formula (I):
- R1CH═CR2[P(O)(OCR3R4CR5R6O)] (I)
- wherein R1, R2, R3, R4, R5 and R6 have the same meaning as above.
An alkenyldiphosphonic acid ester compound of the following general formula (IV):
- R7C[P(O)(OCR3R4CR5R6O)]═CH—R8—CH═CR9[P(O)(OCR3R4CR5R6O)] (IV)
- wherein R3, R4, R5 and R6 have the same meaning as above, R7 and R9 each stand for a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, a heteroaryl group, an alkenyl group, an alkoxy group, an aryloxy group or a silyl group and R8 stands for an alkylene group, a cycloalkylene group or an arylene group.
An alkenyldiphosphonic acid ester compound of the following general formula (V):
- R7CH═C[P(O)(OCR3R4CR5R6O)]—R8—C[P(O)(OCR3R4CR5R6O )]═CHR9 (V)
- wherein R3, R4, R5, R6, R7 and R8 have the same meaning as above.
A process for the preparation of an alkenyldiphosphonic acid ester, comprising reacting a diacetylene compound of the following formula (VI):
- R7C≡C—R8—C≡CR9 (VI)
- wherein R7, R8 and R9 have the same meaning as above, with a cyclic secondary phosphonic acid ester of the following formula (III):
- HP(O)(OCR3R4CR5R6O) (III)
- wherein R3, R4 and R5 and R6 have the same meaning as above, in the presence of a catalyst of a metal of Group 9 of the Periodic Table to obtain an alkenyldiphosphonic acid ester of the following formula (IV) and/or formula (V):
- R7C[P(O)(OCR3R4CR5R6O)]═CH—R8—CH═CR9[P(O)(OCR3R4CR5R6O)] (IV)R7CH═C[P(O)(OCR3R4CR5R6O)]—R8—C[P(O)(OCR3R4CR5R6O)]═CHR9 (V)
- wherein R3, R4, R5, R6, R7, R8 and R9 have the same meaning as above.
Dependencies are inferred from the claim text.