Claims
- 1. A process for the epoxidation of an unsaturated (meth)acrylic compound of formula I: ##STR49## wherein: X is oxygen, sulphur, NH, -NR.sup.3 in which R.sup.3 is an alkyl group having 1 to 12 carbon atoms, or --O--(CH.sub.2).sub.n in which n is an integer ranging from 1 to 16 inclusive, R.sup.2 is a hydrocarbon of 2 to 20 carbon atoms, which is straight-chain or branched alkyl, monocyclic or polycyclic cycloalkyl or heterocycloalkyl, and alkylaryl chains, said hydrocarbon comprising an olefinic double bond,
- R.sup.1 is hydrogen or alkyl of 1 to 5 carbon atoms, comprising reacting said unsaturated (meth) acrylate, at a temperature of between 10.degree. C. and 60.degree. C. with at least one oxidizing compound chosen from:
- hydrogen peroxide in the presence of at least one catalyst chosen from alkali metal molybdates and tungstates and in the presence of at least one phase transfer agent, and
- when R.sup.2 denotes a polycyclic cycloalkyl or heterocycloalkyl chain, an organic peracid or hydrogen peroxide in the presence of at least one heteropolyacid.
- 2. An epoxidation process according to claim 1, wherein the reaction is carried out in the presence of a chlorinated or aromatic solvent.
- 3. An epoxidation process according to claim 1, a peracid being chosen as the oxidizing compound, the peracid being formed in situ by the action of hydrogen peroxide on the corresponding organic acid.
- 4. An epoxidation process according to claim 2, a peracid being chosen as the oxidizing compound, the peracid being formed in situ by the action of hydrogen peroxide on the corresponding organic acid.
- 5. An epoxidation process according to claim 1, the combination of hydrogen peroxide and a heteropolyacid being chosen as the oxidizing agent, wherein the heteropolyacid is of the formula:
- H.sub.n A.sub.a D.sub.c O.sub.y.xH.sub.2 O
- in which
- A represents phosphorus, boron, silicon, germanium, tin, arsenic, antimony, copper, nickel, cobalt, iron, cerium, thorium, chromium or a mixture of at least two of these elements;
- D represents molybdenum, tungsten, vanadium or a combination of at least two of these elements;
- a is a number from 0.1 to 10 inclusive;
- c is a number from 6 to 18 inclusive;
- n is the number of acid hydrogens in the heteropolyacid and is a number higher than 1;
- y is the number of oxygens in the heteropolyacid and is a number on the order of 10 to 70; and
- x is the number of moles of water of crystallization and is a number of from 0 to about 40.
- 6. An epoxidation process according to claim 2, the combination of hydrogen peroxide and a heteropolyacid being chosen as the oxidizing agent, wherein the said heteropolyacid is of the formula:
- H.sub.n A.sub.a D.sub.c O.sub.y.xH.sub.2 O
- in which
- A represents phosphorus, boron, silicon, germanium, tin, arsenic, antimony, copper, nickel, cobalt, iron, cerium, thorium, chromium or a mixture of at least two of these elements;
- D represents molybdenum, tungsten, vanadium or a combination of at least two of these elements;
- a is a number from 0.1 to 10 inclusive;
- c is a number from 6 to 18 inclusive;
- n is the number of acid hydrogens in the heteropolyacid and is a number higher than 1;
- y is the number of oxygens in the heteropolyacid and is a number on the order of 10 to 70; and
- x is the number of moles of water of crystallization and is a number of from 0 to about 40.
- 7. A (meth) acrylic epoxide of formula V: ##STR50## wherein: X is oxygen or sulfur, a --NH radical, --NR.sup.3 in which R.sup.3 is an alkyl group of 1 to 12 carbon atoms, and oxyalkylene --O--(CH.sub.2).sub.n in which n is an integer ranging from 3 to 16, inclusive,
- R.sup.1 is a hydrogen or alkyl of 1 to 5 carbon atoms, and
- R.sup.4 is a hydrocarbon chain comprising 2 to 20 carbon atoms, chosen from straight-chain or branched alkyl, monocyclic or polycyclic cycloalkyl or heterocycloalkyl, and alkylaryl chains, said hydrocarbon chain comprising an oxirane group with the exception of vinylnorbornyl and dicyclopentenyloxyethyl epoxides.
- 8. An opened (meth) acrylic epoxide of formula V: ##STR51## wherein: X is oxygen or sulfur, an --NH radical, --NR.sup.3 in which R.sup.3 is an alkyl group of 1 to 12 carbon atoms, or oxyalkylene --O--(CH.sub.2).sub.n, in which n is an integer ranging from 3 to 16 inclusive;
- R.sup.1 is hydrogen or alkyl having 1-5 C atoms; and
- R.sup.4 is a hydrocarbon chain comprising 2-20 C atoms, which is straight-chain or branched-chain alkyl, monocyclic or polycyclic cycloalkyl, heterocycloalkyl or alkylaryl, said hydrocarbon chain comprising an opened oxirane group with the exception of that from vinylnorbornyl and dicyclopentenyloxyethyl epoxides,
- with the proviso that if R.sup.4 is straight-chain or branched chain alkyl, X is not oxygen.
- 9. A compound of the formula: ##STR52##
- 10. A compound of the formula: ##STR53##
- 11. A compound according to claim 6, wherein R.sup.4 is monocyclic or polycyclic cycloalkyl, heterocycloalkyl or alkylaryl.
- 12. A compound according to claim 6, wherein X is is sulfur, an --NH radical, --NR.sup.3 in which R.sup.3 is an alkyl group of 1 to 12 carbon atoms, or oxyalkylene --O--(CH.sub.2).sub.n, in which n is an integer ranging from 3 to 16 inclusive.
Priority Claims (1)
Number |
Date |
Country |
Kind |
90/08 607 |
Jul 1990 |
FRX |
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Parent Case Info
This is a division, of application Ser. No. 07/725,318 filed Jul. 8, 1991, U.S. Pat. No. 5,283,360.
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Divisions (1)
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Number |
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Parent |
725318 |
Jul 1991 |
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