US 5,703,270 AGranted

Method for preparing a vinyl compound having a hydroxy group

AssigneeNippon Shokubai Co., Ltd.

InventorsKoichi Nakagawa, Mitsuaki Makino, Yuichi Kita

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Abstract

A vinyl compound having a hydroxy group of the formula (1) ##STR1## wherein R is a hydrogen atom or an organic residue, X is a --CN group, a --COR.sub.0 group or a --COOR.sub.0 group and R.sub.0 is a hydrogen atom or an organic residue, is prepared by reacting a vinyl compound of the formula (2) ##STR2## wherein X is a --CN group, a --COR.sub.0 group or a --COOR.sub.0 group and R.sub.0 is a hydrogen atom or an organic residue, with an aldehyde series compound in the presence of a tertiary amine compound, and water in a sufficient amount for forming an aqueous phase upon the completion of the reaction. In this method, since the aqueous phase is formed upon the completion of the reaction, the organic phase including the vinyl compound having a hydroxy group and the aqueous phase including the tertiary amine compound can be easily separated.

A method for preparing a vinyl compound having a hydroxy group of the formula (1) ##STR5## wherein R is derived from an aldehyde series compound selected from the group consisting of formaldehyde, acetoaldehyde, propionaldehyde, butylaldehyde, valeraldehyde, isobutylaldehyde, pivalynaldehyde, cyclohexylaldehyde, cyclohexenealdehyde, benzaldehyde, tolualdehyde, anisaldehyde, furfural, trioxane, paraacetoaldehyde, and an oxymethylene compound of the formula

HO(CH.sub.2 O).sub.p Y
wherein Y is a hydrogen atom, a straight-chain or branched-chain alkyl group of 1 to 8 carbons, or an optionally substituted cycloalkyl group of 3 to 10 carbons, and p is an integer of from 1 to 100;
X is a --COOR.sub.0 group and R.sub.0 is a hydrogen atom or an organic residue selected from the group consisting of an alkyl group of 1 to 18 carbons, a cycloalkyl group of 3 to 10 carbons, an aryl group, a hydroxyalkyl group of 1 to 8 carbons, a --(CH.sub.2).sub.m NR.sub.1 R.sub.2 group, a --(CH).sub.2 N.sup.+ R.sub.1 R.sub.2 R.sub.3.M.sup.- group or a --(C.sub.2 H.sub.4 O).sub.n R.sub.4 group, wherein R.sub.1, R.sub.2 and R.sub.3 respectively represent straight-chain or branched-chain alkyl groups of 1 to 8 carbons, m is an integer of from 2 to 5, M.sup.- is Cl.sup.-, Br.sup.-, CH.sub.3 COOO.sup.-, HCOO.sup.-, 1/2SO.sub.4.sup.2-, 1/3 PO.sub.4.sup.3-, R.sub.4 is a straight-chain or branched-chain alkyl group of 1 to 18 carbons and n is an integer of from 1 to 80, comprising the step of:
reacting a vinyl compound of the formula (2) ##STR6## wherein X is a --COOR.sub.0 group;
with an aldehyde series compound selected from the group consisting of formaldehyde, acetoaldehyde, propionaldehyde, butylaldehyde, valeraldehyde, isobutylaldehyde, pivalynaldehyde, cyclohexylaldehyde, cyclohexenealdehyde, benzaldehyde, tolualdehyde, anisaldehyde, furfural, trioxane, paraacetoaldehyde, and an oxymethylene compound of the formula
HO(CH.sub.2 O).sub.p Y
wherein Y is a hydrogen atom, a straight-chain or branched-chain alkyl group of 1 to 8 carbons, or an optionally substituted cycloalkyl group of 3 to 10 carbons, and p is an integer of from 1 to 100;
in a presence of a tertiary amine compound and water in a sufficient amount for obtaining an aqueous phase upon completion of the reaction.

5 more elements

Facts

Application

08/394,013Filed 22 Feb 1995

Priority

JP 6-02844725 Feb 1994

Granted

30 Dec 1997

Term ends

Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07C 253/30
Preparation of carboxylic acid nitriles: by reactions not involving the formation of cyano groups
C07C 45/72
By increase in the number of carbon atoms: by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
C07C 45/75
By reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups: reactions with formaldehyde
C07C 67/343
By isomerisation; by change of size of the carbon skeleton: by increase in the number of carbon atoms

Abstract

Claims43