1,6-Hexanediol Purification via Distillation

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Solution Overview

Problem

Current methods for producing 1,6-hexanediol with low nitrogen content are costly and inefficient, as they require the use of acidic and/or basic ion exchangers, leading to increased solvent use and product losses, and existing processes do not effectively remove nitrogenous compounds, which can cause catalytic side reactions in polyurethane production.

Innovation Solution

A process involving the distillation of 1,6-hexanediol with carboxylic acids or esters that have a higher boiling point than 1,6-hexanediol, where these components are in contact with the 1,6-hexanediol at temperatures ≥100°C for at least 5 minutes, allowing for the effective removal of nitrogenous components and achieving a nitrogen content of less than 5 ppm without the need for ion exchangers or additional solvents.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If acidic and/or basic ion exchangers are used to remove nitrogen-containing compounds from 1,6-hexanediol, then the nitrogen content is reduced, but the production costs increase due to the need for ion exchanger replacement and regeneration

Engineering Contradiction:
Improvenitrogen contentVSAvoidproduction cost
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The invention extracts and removes nitrogen-containing compounds from the 1,6-hexanediol stream through distillation, separating the harmful nitrogenous impurities from the desired product without requiring ion exchange media

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention replaces expensive, regenerable ion exchangers with a simple distillation process that uses heat and separation, eliminating the need for costly ion exchange materials and their periodic replacement and regeneration

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Manufacturing precision

If acidic and/or basic ion exchangers are used to purify 1,6-hexanediol, then nitrogen-containing compounds are removed, but solvent use increases due to rinsing requirements

Engineering Contradiction:
Improvenitrogen contentVSAvoidsolvent use
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The invention extracts nitrogen-containing compounds through distillation separation, removing impurities without requiring rinsing solvents that would be needed to clean ion exchanger beads

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The distillation process continuously separates nitrogenous compounds from 1,6-hexanediol in a single operation, eliminating the intermittent rinsing steps required when using ion exchangers

Inventive Principle:
Principle #20Continuity of useful action

3Manufacturing precision

If ion exchangers are used to remove nitrogenous compounds, then purification is achieved, but product losses increase due to rinsing requirements

Engineering Contradiction:
Improvenitrogen contentVSAvoidproduct loss
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The invention extracts and removes nitrogen-containing compounds through distillation, separating impurities from the product without requiring product-contact rinsing that causes losses

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention replaces ion exchangers that require product-rinsing for regeneration with a distillation process that uses heat and vapor-liquid separation, eliminating product loss associated with rinsing operations

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

4Manufacturing precision

If additional heating is applied to enable ion exchanger reaction, then purification can proceed, but energy consumption increases

Engineering Contradiction:
Improvenitrogen contentVSAvoidheating energy
Core Design Contradiction:
Manufacturing precisionVSUse of energy by moving object

Solution Approach 1:

The invention utilizes phase transitions (vaporization and condensation) in distillation to separate nitrogenous compounds from 1,6-hexanediol, achieving purification through physical property differences rather than chemical reactions requiring sustained heating

Inventive Principle:
Principle #36Phase transitions

Solution Approach 2:

The distillation process continuously separates components based on volatility differences, maintaining efficient heat utilization throughout the separation process without the intermittent heating cycles required for ion exchanger regeneration

Inventive Principle:
Principle #20Continuity of useful action

5Manufacturing precision

If ion exchangers are used for nitrogen removal, then purification is achieved, but device complexity increases due to regeneration requirements

Engineering Contradiction:
Improvenitrogen contentVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention extracts nitrogen-containing compounds through simple distillation separation, eliminating the complex ion exchange and regeneration equipment required by alternative methods

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention replaces complex, regenerable ion exchange systems with a simpler distillation process that requires no regeneration equipment, operator intervention, or complex process control systems

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

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 process efficiently produces 1,6-hexanediol with a nitrogen content of less than 5 ppm, reducing production costs and minimizing side reactions in subsequent polyurethane production, enabling the production of high-quality polymers without the need for costly ion exchanger regeneration or additional solvent use.

Implementation Method 1

more than 500 ppm of carboxylic acids and/or esters are present which have a higher boiling point than 1,6-hexanediol and are in contact with at temperatures of ≥100° C. for at least 5 minutes the 1,6-hexanediol

Methodology Applied
Scientific EffectThermal contact: Heating

Implementation Method 2

distilling this mixture from step I... collecting a 1,6-hexanediol with a nitrogen content of less than 5 ppm

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentEP2504301B1Method for producing 1,6-hexanediol
Publication Date: 2014.07.02 BASF SE
  • EP2504301B1 patent drawing

AI summary

The invention relates to a method for producing 1,6-hexanediol, a hexanediol having a nitrogen weight of less than 5 ppm being obtained. The invention further relates to 1,6-hexanediol having a nitrogen content of less than 5 ppm and to the use of said 1,6-hexanediol for producing polymers.