Integrated Fischer-Tropsch Hydroformylation and Alkylation Process

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Solution Overview

Problem

The existing methods for producing detergent range alcohols and alkyl benzenes are inefficient, particularly when the concentration of olefins is low, as the cost of recovery exceeds the value generated by converting olefins to alcohols, and there is a challenge in effectively separating aldehydes/alcohols from paraffins due to overlapping boiling points.

Innovation Solution

A process integrating Fischer-Tropsch with hydroformylation and alkylation reactions, where a hydrocarbon feed stream from Fischer-Tropsch is subjected to hydroformylation, followed by separation of aldehydes/alcohols and paraffins, dehydrogenation of paraffins to olefins, and subsequent alkylation to produce alkyl benzene, using a mid-boiling polar entrainer in azeotropic distillation for efficient separation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If distillation is used to recover olefins from Fischer-Tropsch condensate, then olefin recovery is achieved, but the cost of recovery exceeds the value generated when olefin concentration is low

Engineering Contradiction:
Improveolefin recoveryVSAvoidrecovery cost
Core Design Contradiction:
Quantity of substanceVSEase of manufacture

Solution Approach 1:

The patent combines the hydroformylation reaction with the alkylation reaction in a single integrated process flow. The hydroformylation reactor produces aldehydes/alcohols directly from olefins, and the same stream is then fed to the alkylation reactor without requiring separate recovery and processing steps. This merging eliminates the need for costly distillation-based olefin recovery when olefin concentration is low, as the olefins are directly converted to valuable products in situ.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The integrated reactor system performs multiple functions simultaneously: it conducts hydroformylation to convert olefins to aldehydes/alcohols, separates the reaction products, and feeds the output to alkylation to produce alkyl benzenes. This multi-functional approach allows the process to handle varying olefin concentrations efficiently, converting low-concentration olefins directly into high-value detergent range products without requiring separate recovery operations.

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

2Quantity of substance

If conventional separation methods are used to separate aldehydes/alcohols from paraffins, then separation is achieved, but the overlapping boiling points make effective separation difficult

Engineering Contradiction:
Improvealdehyde/alcohol separationVSAvoidseparation difficulty
Core Design Contradiction:
Quantity of substanceVSDevice complexity

Solution Approach 1:

The patent introduces a selective catalyst system in the hydroformylation reaction that facilitates the formation of aldehydes/alcohols with distinct physical properties from the paraffin stream. The catalyst system (modified Rh or Co) selectively converts olefins to oxygenated products that can be more easily separated from paraffins through subsequent separation units, overcoming the difficulty posed by overlapping boiling points through chemical transformation rather than purely physical separation.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Productivity

If high temperature Fischer-Tropsch reaction is used, then hydrocarbon production is achieved, but the concentration of olefins is relatively high making economic recovery difficult

Engineering Contradiction:
Improvehydrocarbon productionVSAvoidolefin recovery economics
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent changes the operational parameters by integrating the hydroformylation and alkylation reactions into a single continuous process flow at controlled temperatures. Instead of recovering high-concentration olefins from high-temperature Fischer-Tropsch condensate, the process directly converts these olefins to aldehydes/alcohols and then to alkyl benzenes, transforming the economic challenge of high olefin concentration into an advantage by directly utilizing the olefins as feedstock for high-value detergent 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

This integrated process enables the co-production of alcohols and alkyl benzene efficiently, reducing production costs and overcoming separation challenges, achieving economies of scale and flexibility in product output.

Implementation Method 1

a hydrocarbon feed stream containing olefins and paraffins is subjected to a hydroformylation reaction to provide a hydroformylation product containing aldehydes/alcohols and paraffins

Methodology Applied
Scientific EffectHydroformylation reaction: Chemical Bonding

Implementation Method 2

The aldehyde/alcohol product is preferably separated from the paraffins by azeotropic distillation in an azeotropic distillation column, wherein the solvent in the column is a mid-boiling polar entrainer

Methodology Applied
Scientific EffectAzeotropic distillation: Distillation

Implementation Method 3

the paraffin stream separated from the hydroformylation product is subjected to a dehydrogenation reaction to form a dehydrogenation product containing olefins and paraffins

Methodology Applied
Scientific EffectDehydrogenation reaction: Chemical Bonding

Implementation Method 4

the dehydrogenation product is subjected to an alkylation reaction to convert olefins to alkyl benzene

Methodology Applied
Scientific EffectAlkylation reaction: Chemical Bonding

Data Source

PatentUS7728178B2Production of detergent range alcohols
Publication Date: 2010.06.01 SASOL TECHNOLOGY (PTY) LTD
  • US7728178B2 patent drawing
  • US7728178B2 patent drawing

AI summary

This invention relates to a process for the production of aldehydes/alcohols and alkyl benzene. According to the invention, a hydrocarbon feed stream containing olefins and paraffins having an average number of carbon atoms from 10 to 18 per molecule, typically derived from the condensation product of a Fischer-Tropsch reaction is subjected to a hydroformylation reaction to provide a hydroformylation product containing aldehydes/alcohols and paraffins. An aldehyde/alcohol product is separated from the paraffins in the hydroformylation product to provide an aldehyde/alcohol product stream and a paraffin stream. The paraffin stream separated from the hydroformylation product is then subjected to a dehydrogenation reaction to form a dehydrogenation product containing olefins and paraffins, and the dehydrogenation product is subjected to an alkylation reaction to convert olefins to alkyl benzene.