Polyol Production via Concentrated Formaldehyde Addition

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Solution Overview

Problem

Existing processes for preparing polyols through the reaction of aldehydes with formaldehyde result in high energy costs due to the need for extensive removal of unreacted formaldehyde, which is often supplied in dilute aqueous solutions, leading to inefficient energy use and potential temperature peaks that affect reaction selectivity.

Innovation Solution

A two-step process where an aliphatic C2-C9 aldehyde is first reacted with formaldehyde in the presence of an inorganic base, followed by the addition of a different aliphatic aldehyde to the reaction solution without intermediate workup, allowing for simultaneous consecutive conversion and reducing residual formaldehyde contamination, thereby minimizing energy expenditure for formaldehyde recovery.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If formaldehyde is supplied in dilute aqueous solutions to prepare polyols, then the reaction can proceed with good selectivity, but the energy costs for removal of unreacted formaldehyde become very high

Engineering Contradiction:
Improvereaction selectivityVSAvoidenergy costs for formaldehyde removal
Core Design Contradiction:
Manufacturing precisionVSUse of energy by moving object

Solution Approach 1:

The patent changes the concentration parameter of formaldehyde from dilute (typically 37-50% aqueous solutions) to concentrated (at least 70% by weight, preferably at least 85% by weight). This parameter change allows the reaction to proceed with acceptable selectivity while dramatically reducing the energy required for formaldehyde removal and water evaporation in the workup process.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies different quality requirements to different stages of the process: concentrated formaldehyde is used in the reaction zone to minimize water content and energy requirements, while controlled addition methods are applied locally to manage the exothermic reaction and maintain selectivity. This local differentiation of concentration quality resolves the contradiction between selectivity and energy efficiency.

Inventive Principle:
Principle #3Local quality

2Manufacturing precision

If a large amount of water is used to absorb heat of reaction, then temperature peaks are avoided and selectivity is maintained, but the amount of unreacted formaldehyde to be removed increases and energy costs rise

Engineering Contradiction:
Improvereaction selectivityVSAvoidamount of water in reaction mixture
Core Design Contradiction:
Manufacturing precisionVSQuantity of substance

Solution Approach 1:

The patent changes the water content parameter from high (traditional dilute aqueous formaldehyde) to low (concentrated formaldehyde with at least 70% by weight formaldehyde). This reduces the total water quantity in the system while managing heat through controlled addition rates and potentially external cooling, thereby reducing the burden of water removal without sacrificing selectivity.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies preliminary cooling measures or controlled addition protocols before temperature peaks can develop. By pre-planning heat management strategies and using concentrated formaldehyde from the start, the process avoids the need for large water quantities as a heat sink, thus reducing the quantity of substance that must be removed later.

Inventive Principle:
Principle #10Preliminary action

3Productivity

If excess formaldehyde is used to increase polyol yield and suppress by-products, then conversion is improved, but the amount of unreacted formaldehyde requiring energy-intensive removal increases

Engineering Contradiction:
Improvepolyol yieldVSAvoidenergy for formaldehyde recovery
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

The patent uses concentrated formaldehyde (at least 70% by weight) which changes the energy balance of the system. While excess formaldehyde is still used to drive conversion and suppress by-products, the concentrated form means less total volume and less associated water must be handled and removed, significantly reducing the energy required for recovery operations compared to using dilute formaldehyde solutions.

Inventive Principle:
Principle #35Parameter changes

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 achieves high conversions and selectivities for polyols while significantly reducing energy input for formaldehyde recovery, enhancing process economics and maintaining reactor flexibility across various reactor types.

Implementation Method 1

By the aldol addition mechanism, the aldehyde can at first form a methylol derivative of the corresponding aldehyde with formaldehyde in a first step

Methodology Applied
Scientific EffectAldol addition: Chemical Bonding

Implementation Method 2

Subsequently, in a second step, the aldehyde group can be reduced to the alcohol group with excess formaldehyde and with stoichiometric amounts of a base in a Cannizzaro reaction

Methodology Applied
Scientific EffectCannizzaro reaction: Chemical Bonding

Implementation Method 3

The underlying reaction between n-butanal and formaldehyde is highly exothermic, and the heat released leads to disadvantageous temperature peaks which can affect the selectivity of the reaction

Methodology Applied
Scientific EffectExothermic reaction: Exothermic Reaction

Data Source

PatentUS10450254B2Method for the combined production of polyols in the presence of an inorganic base
Publication Date: 2019.10.22 OQ CHEM GMBH
  • US10450254B2 patent drawing
  • US10450254B2 patent drawing

AI summary

The present invention relates to a process for simultaneously consecutive preparation of polyols by base-catalyzed reaction of at least two different mid-chain aldehydes with formaldehyde. The simultaneous consecutive mode of operation makes it possible to achieve high conversions and high selectivities for both aldehydes, with additional achievement of a distinct reduction in the amount of unreacted formaldehyde remaining. This leads to improved process economics, since the energy costs for workup of the formaldehyde stream are distinctly reduced.