Claims
- 1. A method of epoxidation of olefins by hydrogen peroxide at a temperature between 0.degree. C. and 120.degree. C. in a liquid phase which comprises, reacting an olefin and hydrogen peroxide in the presence of a catalyst selected from boron oxide or boron oxyacid catalysts, used in an amount of 0.0001 mole to 1 mole of catalyst per mole of hydrogen peroxide, continuously eliminating water introduced with the hydrogen peroxide as well as the water formed in the course of the reaction, from the reaction mixture by distillation during the course of the reaction, and recovering the epoxidized olefin.
- 2. A method according to claim 1 wherein the boron oxide is boron trioxide.
- 3. A method according to claim 1 wherein the boron oxyacid is metaboric acid, orthoboric acid or tetraboric acid.
- 4. A method according to claim 1 in which at least one organic solvent is included in the liquid phase, said solvent being inert with respect to the reactants and in which hydrogen peroxide is soluble under the reaction conditions.
- 5. A method according to claim 4 in which the organic solvent is a member of the group consisting of ethers, alcohols, polyols, esters.
- 6. A method according to claim 5 wherein the organic solvent is a member of the group consisting of oligomers of ethylene oxide, propylene oxide, corresponding methyl ethers, ethyl ethers and the formate, acetate or propionate species thereof.
- 7. A method according to claim 5 wherein the reaction is effected in the presence of diethylene glycol dimethyl ether as the solvent.
- 8. A method according to claim 5 wherein the reaction is effected in the presence of dioxane as the solvent.
- 9. A method according to claim 1 in which the olefin has the general formula: ##STR3## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are identical or different and represent either a hydrogen atom, a straight alkyl radical having from 1 to 30 carbon atoms, a branched alkyl radical or cycloalkyl radical, either substituted or unsubstituted and having from 3 to 12 carbon atoms, a hydrocarbon radical having from 6 to 12 carbon atoms and containing a phenyl group which may be substituted or unsubstituted by alkyl groups: R.sub.1 and R.sub.2 or R.sub.3 and R.sub.4 together may also represent a straight or branched alkylene group having from 2 to 11 carbon atoms or R.sub.1 and R.sub.3 or R.sub.2 and R.sub.4 together may represent a linear or branched alkylene group having from 1 to 10 carbon atoms: the radicals R.sub.1, R.sub.2, R.sub.3 and R.sub.4 can be unsaturated and/or substituted with functional groups which are stable in the reaction medium, such as hydroxy, chloro, fluoro, bromo, iodo, nitro, nitroso, alkoxy, amino, carbonyl, alkylcarbonyl, carboxylic acid, carboxylic acid ester, amide or carbamyl, nitrile or cyano.
- 10. A method according to claim 9 in which the olefin is propene.
- 11. A method according to claim 1 in which the reaction temperature is between 70.degree. C. and 120.degree. C.
- 12. A method according to claim 1 in which the pressure of reaction is between 20 mm. of Hg and 100 bars.
- 13. A method according to claim 1 in which the reactor contains 0.1 to 50 moles of olefins per mole of hydrogen peroxide.
- 14. A method according to claim 1 in which the hydrogen peroxide is in aqueous solution titrating between 70% to 95% by weight of hydrogen peroxide.
- 15. A method according to claim 1 in which the hydrogen peroxide is applied in organic solution titrating between 1% and 30% by weight of hydrogen peroxide.
Priority Claims (2)
Number |
Date |
Country |
Kind |
77 02748 |
Feb 1977 |
FRX |
|
77 32584 |
Oct 1977 |
FRX |
|
Parent Case Info
This is a continuation of application Ser. No. 872,947, filed Jan. 27, 1978, now abandoned.
US Referenced Citations (8)
Foreign Referenced Citations (1)
Number |
Date |
Country |
868890 |
May 1961 |
GBX |
Non-Patent Literature Citations (3)
Entry |
Wolf et al., Jour. Org. Chem., vol. 34, No. 11, Nov. 1969, pp. 3441-3445. |
Chemical Abstracts, vol. 66 (1967) 77863d. |
Daniel Swern, Organic Peroxides, vol. I (1970) pp. 50-51. |
Continuations (1)
|
Number |
Date |
Country |
Parent |
872947 |
Jan 1978 |
|