Stabilizing Ester Viscosity via Ethene Co-oligomerization

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Solution Overview

Problem

The challenge lies in maintaining a constant viscosity of ester mixtures used as plasticizers for PVC, particularly when the composition of n-butene sources fluctuates, making it difficult to ensure consistent plasticizer quality due to changes in the availability and quality of raw materials.

Innovation Solution

Incorporating ethene into the production process by either adding ethene oligomers to butene oligomers or co-oligomerizing ethene with butene, allowing for the adjustment of viscosity through controlled addition of ethene, thereby stabilizing the viscosity of the ester mixture.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If n-butene from fluctuating sources is used as raw material, then productivity is improved by utilizing available C4 sources, but manufacturing precision deteriorates due to variable viscosity of the ester mixture

Engineering Contradiction:
Improveproduction capacityVSAvoidviscosity consistency
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

C2-olefins (ethene) are introduced as an intermediary substance to mediate between the variable n-butene feedstock and the desired constant viscosity product. The C2-olefins mix with C4-olefins in the oligomerization process to produce C8-olefins with controlled branching, thereby buffering the effect of feedstock variations on final product viscosity.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The composition parameters of the feed mixture are dynamically adjusted by varying the proportion of C2-olefins added to the n-butene stream. When viscosity deviates from target values, the C2-olefin content is modified to shift the branching degree of C8-olefins, thereby restoring viscosity to specification.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If the composition of n-butene changes over time, then adaptability is improved by using alternative C4 sources, but stability of the object's composition deteriorates as viscosity becomes unpredictable

Engineering Contradiction:
Improveraw material flexibilityVSAvoidviscosity stability
Core Design Contradiction:
Adaptability or versatilityVSStability of the object's composition

Solution Approach 1:

C2-olefins serve as a stabilizing intermediary that decouples the relationship between variable n-butene composition and final ester viscosity. By introducing this additional controllable variable, the system can adapt to different n-butene sources while maintaining stable product composition through active composition management.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

A feedback control system continuously monitors the viscosity or composition of the ester mixture and adjusts the C2-olefin addition rate accordingly. When viscosity drifts from target values due to n-butene composition changes, the control system modifies the C2-olefin feed to compensate and restore viscosity stability.

Inventive Principle:
Principle #23Feedback

3Ease of manufacture

If branching of C8 olefins is increased, then ease of manufacture is improved by using conventional n-butene oligomerization, but viscosity of the ester mixture increases beyond desired levels

Engineering Contradiction:
Improveprocess simplicityVSAvoidviscosity
Core Design Contradiction:
Ease of manufactureVSTemperature

Solution Approach 1:

The branching parameter of C8-olefins is adjusted by changing the feed composition ratio of C2- to C4-olefins. Lower C2-olefin proportions produce more branched C8-olefins (higher viscosity), while higher C2-olefin proportions produce less branched C8-olefins (lower viscosity), allowing viscosity control while maintaining the simplicity of catalytic oligomerization.

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 enables the production of ester mixtures with a stable viscosity over time, even with fluctuating raw material qualities, by minimizing the branching of C8 olefins and thus reducing the viscosity of the final ester mixture.

Implementation Method 1

a first oligomerization is subjected to obtain an oligomer. At least some of the butene oligomers contained in the oligomer are subjected to a hydroformylation

Methodology Applied
Scientific EffectOligomerization:

Implementation Method 2

at least some of the butene oligomers contained in the oligomer are subjected to a hydroformylation Aldehydes are oxidized

Methodology Applied
Scientific EffectHydroformylation:

Implementation Method 3

at least some of which are hydrogenated by subsequent hydrogenation into an alcohol mixture

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 4

which is then converted into the ester mixture

Methodology Applied
Scientific EffectEsterification:

Data Source

PatentEP3170805B1Influencing the viscosity of n-butene based esters mixtures by targeted use of ethene in the production of the esters precursors
Publication Date: 2018.09.12 EVONIK OPERATIONS GMBH
  • EP3170805B1 patent drawingFigure 0
  • EP3170805B1 patent drawingFigure 1
  • EP3170805B1 patent drawingFigure 2

AI summary

The invention relates to a process for producing an ester mixture in which a feed mixture containing n-butene, the composition of which changes over time, is first oligomerized and then converted into an ester mixture by hydroformylation, hydrogenation, and esterification. An approximation of the actual viscosity of the ester mixture is determined in this process. The objective is to provide a comparatively simple process that makes it possible to convert n-butene with a time-varying composition into an ester mixture whose viscosity can be kept largely constant over a long period, even when using a discontinuous C4 source that yields fluctuating qualities over this period. This is achieved through the targeted use of a second raw material, namely ethene.It has been found that the viscosity of n-butene-based ester mixtures can be influenced by the targeted use of ethene in the preparation of the ester precursors. Specifically, the invention proposes two methods for using ethene: firstly, directly as a C2 olefin, and secondly, as a C8 olefin after prior separate oligomerization.