Integrated Propylene Oxide Process Using Two-Phase Catalyst Recycling

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Solution Overview

Problem

Existing integrated processes for producing propylene oxide and propylene glycol require significant capacity increases and additional equipment, leading to increased energy consumption and operational complexity, particularly when using chlorine, organic hydroperoxides, or hydrogen peroxide as oxidants.

Innovation Solution

Introduce a new step in the process involving the reaction of propene and hydrogen peroxide in the presence of a catalyst mixture comprising a phase transfer catalyst and a heteropolytungstate, maintaining a maximum apparent pH of 6, to produce a solution containing propylene glycols, which is then separated to yield monopropylene glycol and dipropylene glycol, thereby reducing the propylene oxide fed to the water reaction step and increasing overall output.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If the capacity of the reaction unit for reacting propene with oxidant is increased to increase propylene oxide production, then propylene oxide output increases, but additional equipment and substantial investment are required

Engineering Contradiction:
Improvepropylene oxide outputVSAvoidadditional equipment
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent merges the propylene oxide production reaction and propylene glycol production reaction into a single integrated reaction unit. Propene reacts with hydrogen peroxide to form propylene oxide, which immediately reacts with water present in the reaction mixture to form propylene glycol. This combined reaction approach eliminates the need for separate production units and increases propylene oxide output without requiring additional equipment for oxidant production or alcohol conversion.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The reaction unit performs multiple functions simultaneously: it produces propylene oxide, converts propylene oxide to propylene glycol, and handles oxidant conversion. The single reaction unit serves as both a propylene oxide synthesis reactor and a propylene glycol production reactor, maximizing the utility of existing equipment and avoiding the need for additional specialized equipment.

Inventive Principle:
Principle #6Universality (Multi-functionality)

2Productivity

If chlorine or organic hydroperoxide is used as oxidant to produce propylene oxide, then propylene oxide can be produced, but additional equipment is needed for producing the oxidant and preventing its transport

Engineering Contradiction:
Improvepropylene oxide productionVSAvoidoxidant production unit
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent extracts and eliminates the problematic oxidant production and handling steps by using hydrogen peroxide as the oxidant. Hydrogen peroxide can be produced on-site through anthraquinone process or imported in aqueous solution, avoiding the need for complex chlorine handling equipment or organic hydroperoxide production units. This extraction of the problematic oxidant step resolves the contradiction between productivity and device complexity.

Inventive Principle:
Principle #2Taking out (Extraction)

3Adaptability or versatility

If organic hydroperoxide is used as oxidant with conversion of resulting alcohol to marketable product, then propylene oxide production is integrated, but additional equipment is needed for further reacting the alcohol

Engineering Contradiction:
Improveintegration of propylene oxide productionVSAvoidalcohol conversion unit
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent extracts and eliminates the alcohol conversion step by using hydrogen peroxide as oxidant instead of organic hydroperoxide. When hydrogen peroxide is used, water is formed as the byproduct rather than alcohol, eliminating the need for additional equipment to convert alcohol to marketable products like MTBE or styrene. This maintains process integration while reducing device complexity.

Inventive Principle:
Principle #2Taking out (Extraction)

4Productivity

If hydrogen peroxide is used as oxidant with zeolite catalyst, then propylene oxide can be produced, but solvent separation equipment is needed leading to increased energy consumption

Engineering Contradiction:
Improvepropylene oxide productionVSAvoidenergy consumption for solvent separation
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

The patent extracts and eliminates the solvent separation step by using a phase transfer catalyst system that operates without requiring organic solvents. The reaction uses a two-phase system (aqueous phase with hydrogen peroxide and organic phase with propene) separated by a phase transfer catalyst, eliminating the need for solvent recovery and separation equipment, thereby significantly reducing energy consumption.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the reaction parameters by using a phase transfer catalyst system that operates with immiscible aqueous and organic phases. This parameter change eliminates the need for soluble organic solvents that would require energy-intensive separation and recycling, while maintaining high reaction efficiency and propylene oxide production capacity.

Inventive Principle:
Principle #35Parameter changes

5Productivity

If a new unit for reacting propene and hydrogen peroxide is added to increase propylene oxide output, then additional propylene oxide for sale is available, but process complexity increases

Engineering Contradiction:
Improvepropylene oxide output for saleVSAvoidprocess unit complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent merges the propylene oxide production and propylene glycol production into a single integrated reaction unit. By operating this unit at optimized conditions with phase transfer catalyst, the system produces both propylene oxide (for sale) and propylene glycol (for the existing glycol production line) simultaneously, increasing overall productivity without adding separate reaction units or equipment.

Inventive Principle:
Principle #5Merging (Combining)

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

This approach enhances propylene oxide production capacity without expanding existing units, reduces energy consumption, and simplifies the process by recycling the organic phase, thus optimizing the production of propylene glycols and propylene oxide.

Implementation Method 1

reacting propene and hydrogen peroxide in the presence of a catalyst mixture comprising a phase transfer catalyst and a heteropolytungstate

Methodology Applied
Scientific EffectPhase transfer catalysis: Catalysis

Implementation Method 2

catalyst mixture comprising a phase transfer catalyst and a heteropolytungstate

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

dividing the two-phase mixture from step a) into an aqueous phase and an organic phase containing propylene oxide

Methodology Applied
Scientific EffectPhase separation: Density Gradient

Data Source

PatentUS12577218B2Method for increasing propylene oxide output of an integrated process for making propylene oxide and propylene glycol
Publication Date: 2026.03.17 EVONIK OPERATIONS GMBH

AI summary

An integrated process for making propylene oxide and propylene glycol involves reacting propene with an oxidant to provide propylene oxide, reacting a fraction of the propylene oxide with water to provide an aqueous glycol solution containing monopropylene glycol and dipropylene glycol, and separating monopropylene glycol and dipropylene glycol from the glycol solution by a multi-step distillation. The propylene oxide output can be increased without increasing capacity of the unit for reacting propene to propylene oxide, by reacting propene and hydrogen peroxide in the presence of a catalyst mixture, containing a phase transfer catalyst and a heteropolytungstate, in a liquid reaction mixture which contains an aqueous phase with a maximum apparent pH of 6 and an organic phase. The reaction mixture is separated into an organic phase, which is recycled to the reaction, and an aqueous phase containing monopropylene glycol and dipropylene glycol, which is passed to replace the glycol solution.