# US 6,723,861 B2 · Method for producing oxirane

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- Number: US 6,723,861 B2
- Document ID: US6723861B2
- Status: Granted
- Kind: B2
- Application number: 10/297,927
- Filed: 2002-12-19
- Published: 2003-10-02
- Granted: 2004-04-20
- Earliest claimed: 2000-06-28
- Assignees: Solvay (Societe Anonyme)
- Inventors: Dominique Balthasart
- Web page: https://patentgrep.com/patent/US6723861B2

## CPC

- C07D 301/12: with hydrogen peroxide or inorganic peroxides or peracids
- Y02P 20/52: using catalysts, e.g. selective catalysts
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Process for manufacturing oxirane by reaction of an olefin with a peroxide compound in the presence of a catalyst and a solvent in at least two reactors arranged in series, each of which contains a portion of the catalyst, according to which two epoxidation reactions are carried out in series including intermediate distillation, to minimize the formation of by-products.

## Claims

### Claim 1

A process for manufacturing oxirane by reacting of an olefin with a peroxide compound in the presence of a catalyst and a solvent in at least two reactors arranged in series, each of which contains a portion of the catalyst, according to which a first portion of the olefin, the solvent and the peroxide compound are introduced into a first reactor, an epoxidation of the first portion of the olefin is carried out therein in order to form a first portion of the oxirane, a medium comprising the first portion of oxirane formed, the solvent, the unconverted olefin and, where appropriate, the unconsumed peroxide compound is removed from this reactor and introduced into a distillation column, the majority of the oxirane formed and of the unconverted olefin is collected at the top of the column, the medium depleted in oxirane and containing, where appropriate, the unconsumed peroxide compound is collected at the bottom of the column, the medium depleted in oxirane and another portion of the olefin and optionally another portion of the peroxide compound are introduced into a subsequent reactor, an epoxidation of the other portion of the olefin is carried out therein in order to form another portion of the oxirane, and the other portion of the oxirane thus formed is collected.

### Claim 2 (depends on 1)

The process according to claim 1, in which the medium leaving the subsequent reactor and containing the other portion of the oxirane, the solvent, the unconverted olefin and possibly the unconsumed peroxide compound is introduced into a subsequent distillation column, the majority of the other portion of the oxirane and of the unconverted olefin are collected at the top of this column and the solvent and possibly the unconsumed peroxide compound are collected at the bottom of this column.

### Claim 3 (depends on 2)

The process according to claim 2, in which the process is carried out in two reactors arranged in series and in which the medium collected at the bottom of the second distillation column is recycled into the first reactor.

### Claim 4 (depends on 1)

The process according to claim 1, in which the mixture of oxirane and of unconverted olefin collected at the top of the distillation column (first and/or subsequent column) is introduced into a condenser in which the oxirane is separated from the unconverted olefin which is recycled into one of the reactors.

### Claim 5 (depends on 1)

The process according to claim 1, in which all the reactors are of identical size.

### Claim 6 (depends on 1)

The process according to claim 1, in which the catalyst is present in each reactor in the form of particles, at least a portion of which is in fluidized form.

### Claim 7 (depends on 6)

The process according to claim 6, in which the medium leaving the reactor (first and/or subsequent reactor) passes through a filter before being introduced into the distillation column (first and/or subsequent column).

### Claim 8 (depends on 1)

The process according to claim 1, in which the medium entering the distillation column (first and/or subsequent column) is first subjected to a depressurization before being introduced into this distillation column.

### Claim 9 (depends on 1)

The process according to claim 1, in which all of the peroxide compound is introduced into the first reactor.

### Claim 10 (depends on 1)

The process according to claim 1, in which the oxirane is propylene oxide or epichlorohydrin, the olefin is propylene or allyl chloride, the peroxide compound is hydrogen peroxide, the solvent is methanol and the catalyst contains TS-1.

### Claim 11 (depends on 1)

The process according to claim 1, wherein no substantial amount of solvent is removed between reactors and immediate subsequent reactors.

### Claim 12 (depends on 1)

The process according to claim 1, wherein three reactors arranged in series are used.