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Oxo‐alcohols
developed in partnership with
The Dow Chemical Company (Dow)
The LP OxoSM technology is the world’s leading technology for use in the manufacture of oxo alcohols from
olefins. This technology from Johnson Matthey 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‐catalyzed 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 aldolization of the normal‐butyraldehyde followed by hydrogenation of the aldol
intermediates.
The globally proven LP Oxo technology has been licensed in more than 30 plants in 15 countries around the
world. Plants utilizing this technology collectively produce over 60% of the world’s butyraldehyde and
contribute to more than 85% of the world’s licensed propylene based oxo capacity.
We offer a range of 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.
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
utilizing the proprietary NORMAX™ catalyst, an organophosphite ligand available from Dow.
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 aldolization and dehydration reactions are conducted in the
presence of aqueous caustic soda at 120°C:
Hydrogenation
In the LP Oxo Alcohols process, alcohols are produced by low pressure rhodium‐catalyzed 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:
2‐ethylhexanol (2‐EH) is produced from normal‐butyraldehyde in two reaction steps. The first step is the
aldolization 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:
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 Oxo technology
Our LP Oxo technology for production of 2‐ethylhexanol, n‐butanol, iso‐butanol:
Additional applications of the LP OxoSM technology in commercial applications include a process for
producing 2‐propylheptanol (2‐PH), a high‐value C10 plasticizer from mixed butenes feedstock.
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.
A unique application of the LP Oxo technology include conversions of long chain olefins derived from Fischer
Tropsch to synthesis to C12 to C15 detergent range alcohols.
Process option: SELECTOR catalyst technology
For applications using propylene, the LP Oxo technology offers different catalyst systems depending on the
desired conversion to normal and iso‐butyraldehydes.
SELECTOR 10
The SELECTOR 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.
SELECTOR 30
The SELECTOR 30 technology utilizes 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 Oxo technology.
VST allows isomer selectivity to be varied online in a single LP Oxo 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 Johnson Matthey advantage
LP Oxo SELECTOR 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.
For applications using propylene, the LP Oxo 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 Oxo technology is suitable for a range of C3‐C16 olefin feedstocks and
product mixes.
Process flexibility
The LP Oxo technology has been utilized 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 product needs.
The superior catalyst system and simple flow sheet of LP Oxo enables low
investment cost, high feedstock efficiency and a reliable plant which is easy
to operate and maintain.
LP OxoSM ‐ value for We have an extensive track record of delivering project success using
money 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.
The information contained within this document was previously published on a former DAVYTM website.
Information contained in this publication or as otherwise supplied to Users is believed to be accurate and correct at time of going to
press, and is given in good faith, but it is for the User to satisfy itself of the suitability of the Product for its own particular purpose.
Johnson Matthey plc (JM) gives no warranty as the fitness of the Product for any particular purpose and any implied warranty or
condition (statutory or otherwise) is excluded except to the extent that exclusion is prevented by law. JM accepts no liability for loss
or damage (other than that arising from death or personal injury caused by JM’s negligence or by a defective Product, if proved),
resulting from reliance on this information. Freedom under Patent, Copyright and Designs cannot be assumed.
Johnson Matthey Davy Technologies Limited, Registered Office 5th Floor 25 Farringdon Street London EC4A 4AB Registered in
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