Licensed Processes

Oxo Alcohols

Developed in partnership with The Dow Chemical Company (Dow)

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Introduction

The LP OxoSM technology is the world’s leading technology for use in the manufacture of oxo alcohols from olefins. This technology from JM Davy and Dow Global Technologies, Inc., a subsidiary of The Dow Chemical Company (Dow) offers licensees a combination of superior catalyst systems and a simple flowsheet, which results in few equipment items, low investment cost, and high feedstock efficiency in a plant that is environmentally compliant, reliable, easy to operate, and maintain.

In the LP Oxo Alcohols process, alcohols are produced by low pressure rhodium-catalysed hydroformylation of an olefin with syngas (CO and H2) followed by hydrogenation of the intermediate aldehyde.

For example, propylene is hydroformylated to produce normal-butyraldehyde and iso-butyraldehyde which are then hydrogenated to produce normal-butanol and iso-butanol respectively. The production of 2-ethylhexanol is achieved by aldolisation of the normal-butyraldehyde followed by hydrogenation of the aldol intermediates.

The globally proven LP OxoSM technology has been licensed in more than 30 plants in 15 countries around the world. Plants utilising this technology collectively produce over 60% of the world’s butyraldehyde and contribute to more than 85% of the world’s licensed propylenebased oxo capacity.

We offer a range SELECTORSM technologies providing extensive flexibility over the production ratio of normal- to iso-butyraldehyde, enabling our licensees to vary product yields in an ever-changing market environment.

LP OxoSM and SELECTORSM are service marks for process licensing services.

Process Flowsheet

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LP oxo ro LP oxo ora adolisation ora adolisation ro hydrogenation ora hydrogenation ro refining ora hydrogenation lower ora hydrogenation lower ro refining lower ora
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Key Reactions

2-ethylhexanol production follows the overall reaction as shown:

Oxo Alcohols big equation1

The following overall reaction produces normal- and iso-butanol:

Oxo Alcohols big equation2

Process Description

Hydroformylation

Butyraldehyde is produced by reacting propylene with carbon monoxide and hydrogen. The major product is the straight chain normal-butyraldehyde with a smaller amount of branched chain iso-butyraldehyde. The reactions are carried out at mild temperature (< 100°C) and low pressure (< 20 bara) in the presence of a homogeneous rhodium based catalyst with a phosphine ligand in the case of LP Oxo SELECTORSM 10 Technology to provide a normal-butyraldehyde isomer ratio of 10:1. An alternative is the LP Oxo SELECTORSM 30 Technology which enables a normal to isomer ratio of 30:1 utilising the proprietary NORMAXTM Catalyst, an organophosphite ligand available from Dow.

NORMAXTM Catalyst is a trademark of Dow.

Oxo Alcohols small equation1-sm

Oxo Alcohols small equation2-sm

Aldolisation

2-ethylhexanol (2-EH) is produced from normal-butyraldehyde in two reaction steps.

The first step is the aldolisation of normal-butyraldehyde to butyraldol and dehydration of butyraldol to produce 2-ethyl 3-propyl acrolein (EPA). The aldolisation and dehydration reactions are conducted in the presence of aqueous caustic soda at 120°C:

Oxo Alcohols small equation3

Oxo Alcohols small equation4

Hydrogenation

In the LP Oxo Alcohols process, alcohols are produced by low pressure rhodium-catalysed hydroformylation of an olefin with syngas (CO and H2) followed by hydrogenation of the intermediate aldehyde.

For example, propylene is hydroformylated to produce normal-butyraldehyde and iso-butyraldehyde which are then hydrogenated to produce normal-butanol and iso-butanol respectively:

Oxo Alcohols small equation5

Oxo Alcohols small equation6

2-ethylhexanol (2-EH) is produced from normal-butyraldehyde in two reaction steps. The first step is the aldolisation of normal-butyraldehyde to butyraldol and dehydration of butyraldol to produce 2-ethyl 3-propyl acrolein (EPA). The second step is the hydrogenation of EPA to 2-EH:

Oxo Alcohols small equation7

Two options are available for hydrogenation. In the liquid-phase hydrogenation scheme the reactions are carried out in the liquid phase over a heterogeneous catalyst at a temperature of approximately 160°C and at pressure below 30 bara. In the vapour-phase hydrogenation scheme the reactions are carried out in the vapour phase over a heterogeneous catalyst at a temperature of approximately 170°C and at pressure below 6 bara.

The crude alcohol produced in hydrogenation is refined to produce the final product 2-ethylhexanol, normal-butanol and iso-butanol.

Process Option: Application of LP OxoSM Technology

Our LP OxoSM Technology for production of 2-ethylhexanol, n-butanol, iso-butanol:

Oxo process options flowsheet1

Oxo process options flowsheet2

Additional applications of the LP OxoSM Technology in commercial application include a process for producing 2-propylheptanol (2-PH), a high-value C10 plasticizer from mixed butenes feedstock.

Oxo process options flowsheet3

The technology has also been used as part of a process to convert heptenes extracted from Fischer Tropsch products to produce co-monomer grade octene-1.

Oxo process options flowsheet4

A unique application of the LP OxoSM Technology include conversions of long chain olefins derived from Fischer Tropsch to synthesis to C12 to C15 detergent range alcohols.

Oxo process options flowsheet5

Process Option: SELECTORSM Catalyst Technology

For applications using propylene, the LP OxoSM Technology offers different catalyst systems depending on the desired conversion to normal and iso-butyraldehydes.


SELECTORSM 10

  • The SELECTORSM 10 Technology employs a phosphine ligand and typically provides a normal-butyraldehyde isomer ratio of 10:1.
  • By varying process conditions it is possible to achieve an isomer ratio in the range from 6:1 to 12:1.


SELECTORSM 30

  • The SELECTORSM 30 Technology utilises the proprietary NORMAXTM Catalyst, an organophosphite ligand available from Dow.
  • This provides the highest commercially-proven isomer selectivity in the industry with a normal-butyraldehyde isomer ratio of 30:1.


VST

  • ‘Variable Selector Technology’ (VST) – is a recent development of the LP OxoSM Technology.
  • VST allows isomer selectivity to be varied online in a single LP OxoSM process without the need for either block or campaign operation.
  • This advanced catalyst system enables complete flexibility in varying the n:i ratio from 2:1 up to 30:1.
The JM Davy Advantage

LP OxoSM SELECTORSM Technology is the world’s premier oxo technology used in the production of alcohols from olefins due to its milder operating conditions, simplified flowsheet and superior catalyst systems.

+Process flexibility:

  • For applications using propylene, the LP OxoSM Technology offers a unique catalyst system enabling flexibility in varying normal- to iso-butyraldehyde ratio from 2:1 to 30:1.
  • The same hydrogenation catalyst and refining systems can be used to make high-quality commercial-grade 2-ethylhexanol, n-butanol and iso-butanol.
  • The LP OxoSM Technology is suitable for a range of C3-C16 olefin feedstocks and product mixes.
  • The LP Oxo Technology has been utilised in converting mixed butenes to 2-propylheptanol (2-PH), a growing plasticizer alcohol alternative to 2-EH. A plant designed to produce 2-ethylhexanol can be converted to produce 2-propylheptanol.
  • The flexibility of the LP Oxo Technology gives our customers the ability to respond to changing market dynamics in areas such as feedstock availability and new products needs.

+LP OxoSM - value for money:

  • The superior catalyst system and simple flow sheet of LP OxoSM enables low investment cost, high feedstock efficiency and a reliable plant which is easy to operate and maintain.
  • We have an extensive track record of delivering project success using experienced personnel within an organization dedicated to licensing. This gives our customers complete confidence in our technology offering.
  • We pursue continuous technology advancement ensuring the long-term competitiveness of our licensees.