Isolation and purification of oxadimethacrylics

A process for preparing oxadimethacrylics of the formula I

• CH.sub.2 .dbd.C(A)CH.sub.2 --O--CH.sub.2 C(A).dbd.CH.sub.2 I
• where A is selected from the group consisting of --COOR.sup.1, --COR.sup.1, --CONR.sup.2 R.sup.3 and --CN and R, R.sup.2 and R.sup.3 are each defined as follows:
• R.sup.1 is hydrogen, alkyl, substituted or unsubstituted cycloalkyl or cycloalkylalkyl, hydroxyalkyl, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalky, substituted or unsubstituted aryl or arylalkyl,
• R.sup.2 and R.sup.3 are each hydrogen, alkyl, substituted or unsbstituted cycloalkyl or cycloalkylalkyl, substituted or unsubstituted aryl or arylalkyl,
• comprising the following steps:
• (I) converting an alcohol of the formula III
• H.sub.2 C.dbd.C(A)CH.sub.2 OH
• into the oxadimethacrylics I, by heating the alcohol in the present of oxygen and at least one tertiary amine yielding a crude mixture;
• and
• (II) adding to the crude mixture obtained in step (I) at least one liquid hydrocarbon having a boiling point of from 20.degree. to 200.degree. C., the weight ratio of hydrocarbon to oxadimethacrylics I being from 1:1 to 100:1, and thereafter separating the crystallized oxadimethacrylics I from the reaction mixture.

A process for preparing oxadimethacrylics of the general formula I'

• CH.sub.2 .dbd.C(A)CH.sub.2 --O--CH.sub.2 C(B).dbd.CH.sub.2 I'
• where A and B are selected from the group consisting of --COOR.sup.1, --COR.sup.1, --CONR.sup.2 R.sup.3 and --CN with the proviso that A is not the same as B and R.sup.1 and R.sup.2 and R.sup.3 are each defined as follows:
• R.sup.1 is hydrogen, alkyl, substituted or unsubstituted cycloalkyl or cycloalkylalkyl, hydroxyalkyl, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalky, substituted or unsubstituted aryl or arylalkyl,
• R.sup.2 and R.sup.3 are each hydrogen, alkyl, substituted or unsubstituted cycloalkyl or cycloalkylalkyl, substituted or unsubstituted aryl or arylalkyl,
• comprising the following steps:
• (I) reacting a mixture of two different acrylics of the general formulae II and IIA ##STR3## with formaldehyde or a formaldehyde donor compound in the presence of oxygen, with at least one tertiary amine to form a reaction mixture containing the alcohols of the formulae III and IIIA ##STR4## converting the reaction mixture containing these alcohols into the oxadimethacrylic I', CH.sub.2 .dbd.C(A)CH.sub.2 --O--CH.sub.2 C(B).dbd.CH.sub.2, by heating in the presence of oxygen, with at least one tertiary amine yielding a crude mixture;
• and
• (III) adding to the crude mixture obtained in step (II) at least one liquid hydrocarbon having a boiling point of from 20.degree. to 200.degree. C. the weight ratio of hydrocarbon to oxadimethacrylics I being from 1:1 to 100:1, and thereafter separating the crystallized oxadimethacrylics from the reaction mixture.

A process for preparing oxadimethacrylics of the formula

• CH.sub.2 .dbd.C(A)CH.sub.2 --O--CH.sub.2 C(B).dbd.CH.sub.2 I'
• where A and B are selected from the group consisting of --COOR.sup.1, --COR.sup.1, --CONR.sup.2 R.sup.3 and CN with the proviso that A is not the same as B and R.sup.1, R.sup.2 and R.sup.3 are each defined as follows:
• R.sup.1 is hydrogen, alkyl, substituted or unsubstituted cycloalkyl or cycloalkylalkyl, hydroxyalkyl, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalky, substituted or unsubstituted aryl or arylalkyl,
• R.sup.2 and R.sup.3 are each hydrogen, alkyl, substituted or unsubstituted cycloalkyl or cycloalkylalkyl, substituted or unsubstituted aryl or arylalkyl,
• comprising the following steps:
• (I) reacting an acrylic II H.sub.2 C.dbd.C(A)H with formaldehyde or a formaldehyde donor compound in the presence of oxygen, with at least one tertiary amine and in the presence of at least one polymerization inhibitor to form an alcohol III and subsequently reacting of the isolated alcohol III, or of the reaction mixture containing the non-isolated alcohol III, with a further, different alcohol IIIA H.sub.2 C.dbd.C(B)CH.sub.2 OH by heating in the presence of oxygen, of at least one tertiary amine and of at least one polymerization inhibitor to form the oxadimethacrylic I, CH.sub.2 .dbd.C(A)CH.sub.2 --O--CH.sub.2 C(B).dbd.CH.sub.2, yielding a crude mixture;
• and
• (II) by adding to the crude mixture obtained in step (I) at least one liquid hydrocarbon having a boiling point of from 20.degree. to 200.degree. C., the weight ratio of hydrocarbon to oxadimethacrylics I being from 1:1 to 100:1, and thereafter separating the crystallized oxadimethacrylics I from the reaction mixture.

A process for preparing oxadimethacrylics of the formula

• CH.sub.2 .dbd.C(A)CH.sub.2 --O--CH.sub.2 C(B).dbd.CH.sub.2 I'
• where A and B are selected from the group consisting of --COOR.sup.1, --COR.sup.1, --CONR.sup.2 R.sup.3 and --CN with the proviso that A is not the same as B and R.sup.1, R.sup.2 and R.sup.3 are each defined as follows:
• R.sup.1 is hydrogen, alkyl, substituted or unsubstituted cycloalkyl or cycloalkylalkyl, hydroxyalkyl, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl, substituted or unsubstituted aryl or arylalkyl,
• R.sup.2 and R.sup.3 are each hydrogen, alkyl, substituted or unsubstituted cycloalkyl or cycloalkylalkyl, substituted or unsubstituted aryl or arylalkyl,
• comprising the following steps:
• (I) converting a mixture of two different alcohols CH.sub.2 .circleincircle.C(A)CH.sub.2 OH III and H.sub.2 C.dbd.C(B)CH.sub.2 OH IIIA into the oxadimethacrylic I', CH.sub.2 .dbd.C(A)CH.sub.2 --O--CH.sub.22 C(B).dbd.CH.sub.2 by heating in the presence of oxygen, of at least one tertiary amine and of at least one polymerization inhibitor, yielding a crude mixture;
• and
• (II) adding to the crude mixture obtained in step (I) at least one liquid hydrocarbon having a boiling point of from 20.degree. to 200.degree. C., the weight ratio of hydrocarbon to oxadimethacrylics I being from 1:1 to 100:1, and thereafter separating the crystallized oxadimethacrylics I from the reaction mixture.