# US 8,785,670 B2 · Process for the production of propylene oxide

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- Number: US 8,785,670 B2
- Document ID: US8785670B2
- Status: Granted
- Kind: B2
- Application number: 13/312,222
- Filed: 2011-12-06
- Published: 2012-06-07
- Granted: 2014-07-22
- Earliest claimed: 2010-12-07
- Assignees: BASF SE; The Dow Chemical Company
- Applicants: Joaquim Henrique Teles; Kai Gumlich; Peter Bassler; Christian Bartosch; Philip Kampe; Hans-Georg Goebbel; Ulrich Mueller; Richard Jacubinas
- Inventors: Joaquim Henrique Teles; Kai Gumlich; Peter Bassler; Christian Bartosch; Philip Kampe; Hans-Georg Goebbel; Ulrich Mueller; Richard Jacubinas
- Web page: https://patentgrep.com/patent/US8785670B2

## CPC

- C07D 301/12: with hydrogen peroxide or inorganic peroxides or peracids
- Y02P 20/582: Recycling of unreacted starting or intermediate materials
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A continuous process for the production of propylene oxide comprising reacting propene with hydrogen peroxide in methanolic solution in the presence of a titanium silicalite-1 catalyst to obtain propylene oxide, wherein a reaction feed comprising propene, methanol and hydrogen peroxide is introduced into a reactor, said reaction feed containing potassium cations and phosphorus in the form of anions of at least one phosphorus oxyacid.

## Claims

### Claim 1

A continuous process for the production of propylene oxide comprising:
reacting propene with hydrogen peroxide in a methanolic solution in the presence of a titanium silicalite-1 catalyst to obtain propylene oxide,
wherein a reaction feed comprising propene, methanol and hydrogen peroxide is introduced into a reactor, wherein the reaction feed comprises from 110 to 190 micromol of potassium cations (K+), relative to 1 mol hydrogen peroxide contained in the reaction feed, and
wherein the reaction feed further comprises phosphorus (P) in the form of anions of at least one phosphorus oxyacid.

### Claim 2 (depends on 1)

The process of claim 1, wherein the reaction feed comprises from 120 to 175 micromol of K+, relative to 1 mol hydrogen peroxide contained the reaction feed.

### Claim 3 (depends on 1)

The process of claim 1, wherein in the reaction feed, a molar ratio of K+ to P is from 0.75 to 1.0.

### Claim 4 (depends on 1)

The process of claim 1, wherein the reaction feed additionally comprises sodium ions (Na+).

### Claim 5 (depends on 4)

The process of claim 4, wherein in the reaction feed, a molar ratio of K+ to Na+ at least 0.1.

### Claim 6 (depends on 4)

The process of claim 4, wherein in the reaction feed, a molar ratio of K+ to Na+ is from 1.0 to 3.0.

### Claim 7 (depends on 4)

The process of claim 4, wherein in the reaction feed, a molar ratio of K+ plus Na+ to P is from 1.43 to 1.53.

### Claim 8 (depends on 1)

The process of claim 1, wherein the total amount of (a) alkali metal ions other than K+ and Na+, (b) alkaline earth metal ions, and (c) other metal ions contained in the reaction feed is 5 micromol at most, relative to 1 mol hydrogen peroxide contained the reaction feed.

### Claim 9 (depends on 1)

The process of claim 1, wherein the reaction feed is obtained from a hydrogen peroxide feed, a methanol feed, and a propene feed.

### Claim 10 (depends on 9)

The process of claim 9, wherein the hydrogen peroxide feed contains less than 110 micromol of K+, relative to 1 mol hydrogen peroxide contained in the hydrogen peroxide feed.

### Claim 11 (depends on 1, 10)

The process of claim 10, wherein at least one solution containing K+ and P in the form of anions of at least one phosphorus oxyacid is added to at least one feed selected form the group consisting of the hydrogen peroxide feed, the propene feed, and the methanol feed, in such an amount that the reaction feed contains K+, Na+, and P in the form of anions of at least one phosphorus oxyacid in amounts as defined in claim 1.

### Claim 12 (depends on 11)

The process of claim 11, wherein the at least one solution is an aqueous solution of dipotassium hydrogen phosphate.

### Claim 13 (depends on 9)

The process of claim 9, wherein the hydrogen peroxide feed is an aqueous or a methanolic or an aqueous/methanolic.

### Claim 14 (depends on 9)

The process of claim 9, wherein the propene feed additionally comprises propane.

### Claim 15 (depends on 1)

The process of claim 1, wherein the reaction feed when introduced into the reactor consists of one liquid phase.

### Claim 16 (depends on 1)

The process of claim 1, wherein the pressure under which the reaction of propene with hydrogen peroxide in the methanolic solution in the presence of the titanium silicalite-1 catalyst is carried out in the reactor is at least 10 bar.

### Claim 17 (depends on 1)

The process of claim 1, wherein the reaction mixture in the reactor is externally and/or internally cooled, wherein the maximum temperature of the reaction mixture in the reactor from 30 to 70° C.

### Claim 18 (depends on 1)

The process of claim 1, wherein the titanium silicalite-1 catalyst contains titanium silicalite-1 as a catalytically active material embedded into a porous matrix.

### Claim 19 (depends on 1)

The process of claim 1, wherein the reaction of propene with hydrogen peroxide in the methanolic solution in the presence of the titanium silicalite-1 catalyst is carried out by a method comprising:
(i) reacting propene with hydrogen peroxide in the methanolic solution in the presence of the titanium silicalite-1 catalyst in at least one reactor R1, wherein a reaction feed comprising propene, methanol and hydrogen peroxide is introduced into R1, wherein the reaction feed comprises from 110 to 190 micromol of potassium cations (K+), relative to 1 mol hydrogen peroxide contained the reaction feed, and further comprises phosphorus (P) in the form of anions of at least one phosphorus oxyacid;
(ii) separating a stream containing non-reacted hydrogen peroxide from the reaction mixture obtained from (i) and removed from R1, wherein the separating is carried out by distillation in at least 1 distillation column K1; and
(iii) mixing the stream containing non-reacted hydrogen peroxide with a propene stream, passing the mixed stream into at least 1 reactor R2 containing the titanium silicalite-1 catalyst, and reacting propene with hydrogen peroxide in R2.

### Claim 20 (depends on 19)

The process of claim 19, further comprising:
(iv) distilling a combined stream comprising the reaction mixture obtained from (iii) and removed from R2, and the top stream obtained from K1, in a distillation column K2 to obtain a top stream having a propylene oxide content of not greater than 100 vol. ppm and a bottom stream having a propene content of not greater than 100 wt. ppm;
(v) distilling the bottoms stream obtained from (iv) in a distillation column K3 to obtain a top stream mixture comprising at least 98 wt. % of propylene oxide and a bottom stream having a propylene oxide content of not greater than 100 wt. ppm.

### Claim 21 (depends on 1, 20)

The process of claim 20, further comprising:
(vi) distilling the bottom stream obtained from (v) in at least one distillation column K4 to obtain a bottoms stream having a methanol content of not greater than 0.5 wt. % and a top stream having a methanol content of at least 98.5 wt. % and a water content of not greater than 1 wt. %;
(vii) recycling the bottoms stream obtained from (vi) as a starting material of the continuous process according to claim 1 and/or as external reflux into (iv) according to claim 20.