Selective epoxidation of unsaturated (meth)acrylates, new functi

Details Selective epoxidation of unsaturated (meth)acrylates, new functi Selective epoxidation of unsaturated (meth)acrylates, new functi

1991-07-08

1994-02-01

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560224, 558250, 564208, C07C 6952

Patent

active

052833607

ABSTRACT:
An unsaturated (meth)acrylic compound of formula: ##STR1## (X.dbd.O, S, NH, NR.sup.3 (R.sup.3 =C.sub.1-12 -alkyl) or O--(CH.sub.2).sub.n (where n=1-16 approximately); R.sup.2 =C.sub.2-20 straight-chain or branched alkyl, monocyclic or polycyclic cycloalkyl or heterocycloalkyl, or alkylaryl hydrocarbon chain, comprising an olefinic double bond in the chain, or at the end of the chain in the case of alkyl or alkylaryl, or an exocyclic or endocyclic olefinic double bond in the case of monocyclic or polycyclic cycloalkyl or heterocycloalkyl; and R.sup.1 =H or C.sub.1-5 -alkyl), is reacted at 10.degree.-60.degree. C. with at least one oxidizing compound (hydrogen peroxide) in the presence of at least one catalyst (alkali metal molybdates and tungstates) and in the presence of at least one phase transfer agent and when R.sup.2 =polycyclic cycloalkyl or hetercycloalkyl, an organic peracid or hydrogen peroxide in the presence of at least one heteropolyacid. To open the epoxide function, the epoxide obtained is reacted with a compound chosen from strong inorganic acids, boron trifluoride etherate complexes, acid salts in the presence of the corresponding acid, halides of trialkylsilanes or trialkoxysilanes, and ketones in the presence of cationic resins.

REFERENCES:
patent: 2794029 (1957-05-01), Phillips et al.
patent: 2935516 (1960-05-01), Frostick, Jr. et al.
Chow et al., "Homo-and Copolymers of Vinyl Este s, Acrylates, and Methacrylates of Some Derivatives of Fatty Acids," Journal of Applied Polymer Science, vol. 13, pp. 1545-1553 (1969).

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