LPG Dehydrogenation for Flexible C5 and C9 Aldehyde Production

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current processes for producing C5 and C9 aldehydes are dependent on specific raw materials, have inefficient resource utilization, and struggle with flexibility in responding to demand fluctuations, leading to economic inefficiencies and increased buyer dependence on volatile raw material prices.

Innovation Solution

A process that uses LPG or NGL as raw materials, where the intermediate is divided into two portions for parallel hydroformylation, allowing flexible production of C5 and C9 aldehydes based on demand, with oligomerization conducted with partial conversion to optimize isomer distribution and heat management, and incorporating isobutene removal through MTBE synthesis to enhance product quality.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If complexly connected compound installations are used for producing C5 and C9 aldehydes from C4 olefins, then C5 and C9 aldehydes can be produced, but the process becomes dependent on specific raw materials (crack C4, FCC C4) and volatile oil prices

Engineering Contradiction:
Improveraw material flexibilityVSAvoiddependence on specific raw materials
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The process uses LPG/NGL as a universal raw material that can be supplied from multiple sources (oil refining, natural gas processing) rather than being dependent on specific C4 cut streams. This multi-source availability provides both adaptability to different feedstock types and reliability through diversified supply chains, resolving the contradiction between raw material flexibility and dependence on specific materials.

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

2Productivity

If steam crackers are optimized towards production of C2 and C3 olefins, then ethene and propene production increases, but C4 yield decreases and availability of high-value crack C4 falls

Engineering Contradiction:
ImproveC2 and C3 olefin productionVSAvoidC4 yield
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The process introduces LPG/NGL as an intermediary raw material that bridges the gap between the optimized C2/C3 production streams and the desired C4-based aldehyde production. By using LPG/NGL (which contains C3-C5 hydrocarbons) as the feedstock, the process can produce C5 and C9 aldehydes without depending on the decreasing C4 yield from steam crackers, thus resolving the contradiction between high C2/C3 productivity and sufficient C4 availability.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Ease of manufacture

If field butanes are used as raw material, then C4 aldehydes can be produced, but continuous turnover of C9 and C13 alcohols is required and buyer dependence on long-term supply contracts increases

Engineering Contradiction:
Improveraw material availabilityVSAvoidcontinuous turnover requirement
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The process changes the molecular weight parameters of the product distribution by using LPG/NGL with a broader C3-C5 hydrocarbon composition. This allows simultaneous production of C5 aldehydes (from C4 olefins) and C9 aldehydes (from C8 olefins via oligomerization), eliminating the need for continuous turnover of high molecular weight alcohols and reducing dependence on long-term supply contracts, thus resolving the contradiction between raw material ease of manufacture and operational complexity.

Inventive Principle:
Principle #35Parameter changes

4Productivity

If dehydrogenation of LPG is used to produce C4 olefins, then C5 and C9 aldehydes can be produced, but resource efficiency is low and inert n-butane and isobutane are not utilized

Engineering Contradiction:
Improvealdehyde productionVSAvoidunutilized inert components
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The process performs preliminary separation and selective utilization of the LPG/NGL feedstock components. By separating the feedstock into useful fractions and selectively dehydrogenating the appropriate components, the process maximizes the utilization of valuable hydrocarbons while managing inert components, thereby improving resource efficiency without compromising aldehyde production productivity.

Inventive Principle:
Principle #10Preliminary action

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 reduces dependence on specific raw material suppliers, optimizes resource use, and allows for flexible production to meet changing demand, improving economic efficiency and product quality by enabling efficient parallel hydroformylation and heat management.

Implementation Method 1

in the case that the feed mixture comprises more than 1.0% by weight unsaturated hydrocarbons: reducing the content of unsaturated hydrocarbons in the feed mixture to a value below 1.0% by weight by subjecting the feed mixture to a hydrogenation

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 2

dehydrogenating the feed mixture to obtain at least one dehydrogenation mixture

Methodology Applied
Scientific EffectDehydrogenation:

Implementation Method 3

subjecting the first portion of the intermediate to an oligomerization in the presence of a solid catalyst comprising amorphous silica/alumina and at least 15% by weight nickel, whereby an oligomer is obtained comprising olefins having eight carbon atoms

Methodology Applied
Scientific EffectOligomerization:

Implementation Method 4

pressurizing the separated olefins having eight carbon atoms with synthesis gas for the purpose of carrying out a first hydroformylation to obtain a first hydroformylation mixture comprising at least aldehydes having nine carbon atoms

Methodology Applied
Scientific EffectHydroformylation:

Implementation Method 5

separating the dehydrogenation mixture by distillation into a first fraction and a second fraction, wherein the first fraction comprises hydrocarbons having four carbon atoms and the second fraction comprises hydrocarbons having three carbon atoms

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 6

incorporating isobutene removal through MTBE synthesis to enhance product quality

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Data Source

PatentUS10227279B2Dehydrogenation of LPG or NGL and flexible utilization of the olefins thus obtained
Publication Date: 2019.03.12 EVONIK OPERATIONS GMBH
  • US10227279B2 patent drawing
  • US10227279B2 patent drawing
  • US10227279B2 patent drawing

AI summary

The object of the invention is to specify a process with which both C5 and C9 aldehydes can be produced economically. Here, the process should be able to to be supplied with the lowest possible dependence on raw material suppliers and also should be able to react flexibly to fluctuations in demand with respect to C5 and C9 aldehydes. The use of resources should also be optimized. The process proposed uses LPG or NGL as raw material. The process according to the invention essentially differs from known LPG-based processes in that the intermediate obtained, after dehydrogenation and removal of by-products, is divided into two portions. C9 aldehyde is produced from the first portion by oligomerization and hydroformylation while C5 aldehyde is obtained by hydroformylation of the second portion. This has the critical advantage that it is possible to divide the intermediate flexibly into the two portions so that either more C5 or more C9 aldehydes can be produced depending on the respective demand.