Oxo alcohols developed in partnership with The Dow Chemical Company (Dow)

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1 Process description: Oxo alcohols developed in partnership with The Dow Chemical Company (Dow) The LP Oxo SM 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 H 2) 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 SELECTOR SM 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.

2 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 SELECTOR SM 10 technology to provide a normal butyraldehyde isomer ratio of 10:1. An alternative is the LP Oxo SELECTOR SM 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:

3 Hydrogenation In the LP Oxo Alcohols process, alcohols are produced by low pressure rhodium catalyzed hydroformylation of an olefin with syngas (CO and H 2) 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, normalbutanol and iso butanol.

4 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 Oxo SM 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.

5 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 normalbutyraldehyde 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 NORMAX TM catalyst, an organophosphite ligand available from Dow. This provides the highest commercially proven isomer selectivity in the industry with a normalbutyraldehyde 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.

6 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. Process flexibility 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. 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. LP Oxo SM value for money 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. 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.

7 The information contained within this document was previously published on a former DAVY TM 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 England No Offices worldwide. For contact details please visit our website. DAVY is a trademark of the Johnson Matthey group of companies. LP Oxo and SELECTOR are service marks of The Dow Chemical Company JM/0317/0/PT/web 2017 Johnson Matthey Group