Method for producing (meth)acrylate derivative having isocyanate group
View Patent ↗The invention aims to provide a method whereby (meth)acrylate derivatives having an isocyanate group can be obtained in high yield by dehydrochlorination of 3-chloropropionate derivatives having an isocyanate group under industrially advantageous and mild conditions, and the content of residual hydrolyzable chlorine can be reduced. A method for producing a (meth)acrylate derivative having an isocyanate group comprises performing dehydrochlorination of a 3-chloropropionate derivative having an isocyanate group in the presence of a basic nitrogen compound having a tertiary nitrogen, the tertiary nitrogen of the basic nitrogen compound having at least one group other than an aromatic ring group.
1. A method for producing a (meth)acrylate derivative having an isocyanate group, the method comprising performing dehydrochlorination of a 3-chloropropionate derivative having an isocyanate group, the derivative being represented by the formula (1), in the presence of a basic nitrogen compound having a tertiary nitrogen to prepare a (meth)acrylate derivative having an isocyanate group, the derivative being represented by the formula (2), wherein the tertiary nitrogen of the basic nitrogen compound has at least one group other than an aromatic ring group:
Cl—CH 2 —CHR 1 —COO—R 2 —NCO (1)
CH 2 ═CR 1 —COO—R 2 —NCO (2)
wherein R 1 is a hydrogen atom or a methyl group, R 2 is an alkylene group of 1 to 10 carbon atoms that may be branched, or a hydrocarbon group in which a cycloalkylene group of 3 to 6 carbon atoms has alkylene groups of 0 to 3 carbon atoms at ends thereof,
wherein the basic nitrogen compound is a trialkylamine.
2. The method for producing a (meth)acrylate derivative having an isocyanate group according to claim 1 , wherein the basic nitrogen compound has a boiling point lower than that of the (meth)acrylate derivative produced.
3. The method for producing a (meth)acrylate derivative having an isocyanate group according to claim 1 , wherein the basic nitrogen compound is insoluble in a reaction solvent.
4. The method for producing a (meth)acrylate derivative having an isocyanate group according to claim 3 , wherein the basic nitrogen compound insoluble in a reaction solvent is an ion-exchange resin having a tertiary nitrogen.
5. The method for producing a (meth)acrylate derivative having an isocyanate group according to claim 1 , wherein the dehydrochlorination is performed at temperatures of 40 to 120° C.
6. The method for producing a (meth)acrylate derivative having an isocyanate group according to claim 1 , wherein the dehydrochlorination is followed by distillation to remove the residual basic nitrogen compound.
7. The method for producing a (meth)acrylate derivative having an isocyanate group according to claim 1 , wherein the group R 2 is an alkylene group of 1 to 10 carbon atoms that may be branched.
8. The method for producing a (meth)acrylate derivative having an isocyanate group according to claim 7 , wherein the group R 2 is —CH 2 —CH 2 — or —CH 2 —CH 2 —.
9. The method for producing a (meth)acrylate derivative having an isocyanate group according to claim 1 , wherein the dehydrochlorination is performed in the presence of the basic nitrogen compound in an equivalent amount of 0.5 to 10 moles per mole of alkali decomposable chlorine in a solution that contains the 3-chloropropionate derivative having an isocyanate group of the formula (1).
10. The method for producing a (meth)acrylate derivative having an isocyanate group according to claim 1 , wherein the hydrolyzable chlorine concentration in the product isolated by simple distillation is not more than 300 ppm.