Process for preparing 1,2-propanediol from propane

Patent metadata

Field	Value
Publication number	US-12459882-B2
Application number	US-202118249729-A
Country	US
Kind code	B2
Filing date	Oct 7, 2021
Priority date	Oct 21, 2020
Publication date	Nov 4, 2025
Grant date	Nov 4, 2025

Abstract

A process for preparing 1,2-propanediol involves dehydrogenating propane to provide a product stream containing propane, propene, and hydrogen; and separating the product stream into a stream containing essentially hydrogen, a stream enriched in propane, and a stream enriched in propene. The process then involves reacting the stream containing essentially hydrogen with oxygen to provide a stream containing hydrogen peroxide; and reacting the stream enriched in propene with the stream containing hydrogen peroxide in the presence of a catalyst mixture, containing a phase transfer catalyst and a heteropolytungstate, in a reaction mixture with two liquid phases. The process further involves separating the reaction mixture of the propene oxidation into an aqueous phase and an organic phase, recycling the organic phase to the propene oxidation, and separating 1,2-propanediol from the aqueous phase.

First claim

The invention claimed is:

1 . A process for preparing 1,2-propanediol, comprising:
a) dehydrogenating a feed stream SI comprising propane, to provide a product stream S2 comprising propane, propene and hydrogen; b) separating product stream S2 into a stream S3 consisting essentially of the hydrogen and a stream S4 comprising the propane and the propene with a combined amount of the propane and the propene of at least 95% by weight; c) reacting all or a part of stream S3 with oxygen, to provide a stream S5 comprising hydrogen peroxide; d) separating stream S4 into a stream S6 enriched in the propane and a stream S7 enriched in the propene; e) reacting all or a part of stream S7 with stream S5 in the presence of a catalyst mixture, comprising a phase transfer catalyst and a heteropolytungstate, in a liquid reaction mixture comprising an aqueous phase with a maximum apparent pH of 6 and an organic phase, wherein apparent pH refers to a value determined by measurement with a glass electrode employing a commercial pH meter calibrated with aqueous buffer solution of known pH for measuring dilute aqueous solutions; f) separating the liquid reaction mixture of e) into an aqueous phase (P a ) comprising 1,2-propanediol and an organic phase (P o ); g) recycling the organic phase (P o ) separated in f) to the reaction of e); and h) separating the 1,2-propanediol from the aqueous phase (P a ) separated in f).

2 . The process of claim 1 , wherein c) comprises
c1) hydrogenating a working solution comprising an alkylanthraquinone and/or an alkyltetrahydroanthraquinone, and at least one solvent for said alkylanthraquinone and/or alkyltetrahydroanthraquinone, with stream S3 in the presence of a hydrogenation catalyst, to provide a hydrogenated working solution, c2) oxidizing the hydrogenated working solution of c1) with a gas comprising molecular oxygen, to provide an oxidized working solution containing dissolved hydrogen peroxide; and c3) extracting the oxidized working solution of c2) with an aqueous extractant to provide stream S5 as an extract comprising water and from 15 to 50% by weight of the hydrogen peroxide.

3 . The process of claim 1 , wherein stream S6 separated in d) is recycled to a).

4 . The process of claim 1 , wherein f) comprises:
separating a stream S8 comprising the propane and the propene, with a combined amount of the propane and the propene of at least 70% by weight, from the liquid reaction mixture, and recycling stream S8 to the separating of d).

5 . The process of claim 4 , wherein stream S8 is combined with stream S4 prior to recycling to d).

Assignees

• Evonik Operations Gmbh

Inventors

• Bolz David
• Wiederhold Holger

Classifications

• C07C29/84

  by extractive distillation · CPC title

• Y02P20/10

  Process efficiency · CPC title

• B01J27/188

  with chromium, molybdenum, tungsten or polonium · CPC title

• C01B15/023

  by the alkyl-anthraquinone process · CPC title

• C07C11/06

  Propene · CPC title