# US 4,399,295 A · Process for preparing oxirane compounds

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- Number: US 4,399,295 A
- Document ID: US4399295A
- Status: Granted
- Kind: A
- Application number: 06/036,153
- Filed: 1979-05-04
- Granted: 1983-08-16
- Earliest claimed: 1977-12-19
- Assignees: Chem Systems Inc.
- Inventors: Martin B. Sherwin; Marshall E. Frank
- Web page: https://patentgrep.com/patent/US4399295A

## CPC

- C07D 301/02: Synthesis of the oxirane ring
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A process for preparing oxirane compounds by the deacyloxylation of a vicinal hydroxyester in the presence of a basic material which comprises carrying out the reaction in a dilute phase transport reactor into which is fed a stream of heated catalyst co-current with a feed gas stream. The catalyst is heated in a fluidized bed heater. The catalyst and product gases are separated in a cyclone separator, the catalyst being returned to the heater and the effluent product gas being further processed to recover product.

## Claims

### Claim 1

In a process for preparing an oxirane compound by the deacyloxylation of a vicinal hydroxyester using as a catalyst a basic material, the improvement which comprises carrying out the process continuously in a dilute phase transport reactor by:
(a) heating a fluidized bed of catalyst in a heating zone to the temperature necessary for carrying out the deacyloxylation process;
(b) introducing said heated catalyst and a preheated feed gas stream into the reactor, wherein the deacyloxylation of a vicinal hydroxyester component of the feed gas is accomplished, thereby producing an oxirane compound;
(c) separating the reacted gas stream from the catalyst;
(d) returning the catalyst to the heating zone for reheating; and
(e) further processing the reacted gas stream to separate out the oxirane product.

### Claim 2 (depends on 1)

The process of claim 1 where the catalyst is supported on an inert support material.

### Claim 3 (depends on 1)

The process of claim 1 where the catalyst support material comprises alumina, carborundum or silica gel.

### Claim 4 (depends on 1)

The process of claim 1 wherein the gas feed stream comprises a vicinal hydroxyester and a carrier gas for said ester.

### Claim 5 (depends on 1)

The process of claim 1 wherein the catalyst is fluidized by an inert gas wherein the inert gas is nitrogen, carbon dioxide or methane.

### Claim 6 (depends on 1)

The process of claim 1 wherein the total pressure in the reactor is sub-atmospheric.

### Claim 7 (depends on 1)

The process of claim 1 wherein the hydroxyester is proplyene hydroxyacetate and the catalyst is potassium silicate or sodium silicate.

### Claim 8 (depends on 6)

The process of claim 6 wherein the partial pressure of the vicinal hydroxyacetate in the reactor is about 1 psia to about 8 psia.

### Claim 9 (depends on 1)

The process of claim 1 wherein the catalyst is potassium silicate or sodium silicata.

### Claim 10 (depends on 1)

The process of claim 1 wherein the catalyst surface area is about 0.15 to about 20 square meters per gram.

### Claim 11 (depends on 1)

The process of claim 1 wherein the catalyst surface area is about 0.15 to about 2.0 square meters per gram.

### Claim 12 (depends on 1)

The process of claim 1 wherein the reactivating gas is steam.

### Claim 13 (depends on 1)

The process of claim 1 wherein the reactivating gas is oxygen containing gas.