1,4-Butanediol Purification via Hydrogenation and Distillation

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Solution Overview

Problem

Conventional distillation methods fail to achieve high purity 1,4-butanediol due to the reactive nature of the mixture, which leads to contamination and impurity issues, particularly with the presence of γ-butyrolactone and 3-(4-hydroxybutoxy)-tetrahydrofuran, limiting the achievable purity to below 99.8 wt %.

Innovation Solution

A novel process involving a series of distillation columns and hydrogenation steps to separate and purify 1,4-butanediol, including a first distillation column for side-draw removal of γ-butyrolactone, a hydrogenation zone to reduce 2-(4-hydroxybutoxy)-tetrahydrofuran content, and subsequent distillation columns to achieve high purity, with specific catalysts and conditions to manage reactions and impurities.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional distillation methods are used to separate 1,4-butanediol from the product mixture, then the separation process is simple and straightforward, but the achievable purity is limited to below 99.8 wt % due to reactive components forming impurities

Engineering Contradiction:
Improvepurity of 1,4-butanediolVSAvoidcomplexity of separation process
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The separation process is divided into multiple distinct stages: first distillation column for removing light components and γ-butyrolactone, hydrogenation zone for treating reactive impurities, second distillation column for final purification. This segmentation allows each stage to address specific impurity types, achieving >99.8 wt % purity that cannot be obtained through single-stage conventional distillation

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

A hydrogenation zone with catalyst is introduced as an intermediary step between distillation stages. This mediator converts reactive impurities like 2-(4-hydroxybutoxy)-tetrahydrofuran into less problematic compounds, enabling the subsequent distillation columns to achieve higher purity without the reactive components interfering with the separation

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If the mixture is subjected to distillation at conventional conditions, then the separation can be carried out using standard equipment, but reactive components undergo unwanted reactions that generate additional impurities and limit purity

Engineering Contradiction:
Improvepurity of 1,4-butanediolVSAvoidreactivity-induced impurities
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The harmful reactivity of components like γ-butyrolactone and 2-(4-hydroxybutoxy)-tetrahydrofuran is converted into a benefit through controlled hydrogenation. The catalyst in the hydrogenation zone selectively transforms these reactive impurities into less reactive compounds, turning the problematic reactivity into a manageable process feature that enables higher purity separation

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The process changes the chemical state of reactive components through hydrogenation reactions, altering their reactivity parameters. By converting double bonds and functional groups in the impurities, the mixture's overall reactivity is reduced, allowing subsequent distillation to proceed without generating additional unwanted reaction products

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

The process achieves 1,4-butanediol purity exceeding 99.8 wt %, overcoming the limitations of conventional methods by effectively managing reactive components and impurities, resulting in a high-purity product.

Implementation Method 1

supplying a crude product stream comprising 1,4-butanediol and one or more of γ-butyrolactone, 2-(4-hydroxybutoxy)-tetrahydrofuran, 4-hydroxybutyl(4-hydroxybutyrate), and 3-(4-hydroxybutoxy)-tetrahydrofuran to a first distillation column

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 2

subjecting the stream from step (c) to hydrogenation in the hydrogenation zone in the presence of a hydrogenation catalyst, and recovering from the hydrogenation zone a 1,4-butanediol product stream having a reduced content of 2-(4-hydroxybutoxy)-tetrahydrofuran

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 3

subjecting the stream from step (c) to hydrogenation in the hydrogenation zone in the presence of a hydrogenation catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 4

passing the 1,4-butanediol product stream from step (d) to a second distillation column operated such that 4-hydroxybutyl(4-hydroxybutyrate) is removed as a bottom stream and removing a 1,4-butanediol stream as overhead

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 5

passing the overhead stream removed in (e) to a third distillation column and recovering a purified 1,4-butanediol stream

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentUS10322988B2Process for purifying a stream comprising 1,4-butanediol
Publication Date: 2019.06.18 JOHNSON MATTHEY DAVY TECHNOLOGIES LTD
  • US10322988B2 patent drawing
  • US10322988B2 patent drawing
  • US10322988B2 patent drawing

AI summary

A crude product stream of 1,4-butandiol and one or more of γ-butyrolactone, 2-(4-hydroxybutoxy)-tetrahydrofuran, 4-hydroxybutyl(4-hydroxybutyrate), and 3-(4-hydroxybutoxy)-tetrahydrofuran is supplied to a first distillation column. A side-draw of 1,4-butanediol and light components is removed, with the light components including at least some of those produced by reaction in the first distillation column. The stream is passed to a hydrogenation zone and subjected to hydrogenation in the presence of a hydrogenation catalyst. A 1,4-butanediol product stream having a reduced content of 2-(4-hydroxybutoxy)-tetrahydrofuran is recovered and passed to a second distillation column operated such that (4-hyroxybutyl)-4-hydroxybutyrate is removed as a bottom stream and a 1,4-butanediol stream is removed as overhead. The overhead stream removed is passed to a third distillation column and a purified 1,4-butanediol stream is recovered.