Mitsubishi Chemical Oxo Alcohol Technology
1. PROCESS FEATURE
The characteristic and superiority of Mitsubishi Oxo Process are following points.
(1) Very high quality of products
The major derivatives of OXO alcohols are plasticizers and acrylates. From the quality
point of view, not only the normal specifications but also small amounts of impurities are
highlighted by our investigations. The small amounts of impurities are hardly able to be
removed by easy distillation of alcohol. Typical advantage of Mitsubishi OXO Process is
it provides super grade alcohol, containing negligible level of those impurities.
Mitsubishi OXO Process is able to produce the highest grade alcohol in the world. This
feature would be a great advantage for the user of Mitsubishi OXO Process.
(2) High conversion efficiency
Two steps reaction makes high propylene conversion.
(3) Economical process
Investment cost and energy consumption are low, because of lower reaction pressure
and moderate reaction temperature,
Plant utilizing Mitsubishi OXO Process needs less labor cost, because of simple process
and stable operation. Particularly less management man-power is needed because the
catalyst activity is stable and so management is not necessary.
(4) Easy operation
Simple process and adequate control system provides easy operation. Mitsubishi OXO
Process has specially advanced OXO Reactor control system to stabilize the reaction
rate and productivity. The selectivity, which is related to the product ratio of normal-
and iso-Butyraldehyde, is also adjusted easily.
(5) Catalyst recovery process
Catalyst activity is stable and high, because of continuous operation of Heavy End
Separation process and Catalyst Recovery process. Stable and high catalyst activity
result in stable plant operation and less labor cost.
MCC has a special process that can recover the greater portion of the expensive Rh
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metal within the battery limit.
(6) High safety
The advantages mentioned above are also the basis of higher safety of Mitsubishi OXO
Process.
2. BLOCK FLOW DIAGRAM
Propylene Synthesis Gas
OXO Reaction H.E. Separation
Catalyst Recovery
iso-Butyraldehyde N/I Separation
n-Butyraldehyde
Aldol Condensation
Hydrogen Gas
Hydrogenation Hydrogenation Hydrogenation
iso-Butanol 2-Ethyl-Hexanol n- Butanol
Raw Material
Reaction
Intermediate Chemical Reaction
Other than Reaction
Final Product
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3. PROCESS DECCRIPTION
PLANT consists of the following four sections.
(1) OXO Section
(2) 2EH Section
(3) NBA Section
(4) IBA Section
3.1 OXO Section
In this section, NBD and IBD are produced from Propylene and Syn-gas.
This section consists of the following four process.
(1) OXO Reaction Process
(2) Aldehyde Separation Process
(3) Heavy End Separation Process
(4) Catalyst Recovery Process
The major reactions are as follows.
CH3CHCH2 + CO + H2 CH3CH2CH2CHO
Propylene Syn-gas Normal- Butyraldehyde (NBD)
CH3CHCH2 + CO + H2 CH3CHCHO
CH3
Propylene Syn-gas Iso-Butyraldehyde (IBD)
3.2 2EH Section
In this section, 2-Ethylhexanol (2EH) is produced from NBD and hydrogen gas.
This section consists of the following three process.
(1) Aldol Condensation and EPA Distillation Process
(2) EPA Hydrogenation Process.
(3) 2EH Distillation Process
The major reactions of Aldol Condensation are as follows.
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Butyraldol
Butyraldol Ethyl Propyl Acrolein (EPA)
The major reactions of hydrogenation of EPA to 2EH are as follows
2-Ethylhexanal
2-Ethylhexanal 2-Ethylhexanol (2EH)
3.3 NBA Section
In this section, Normal-Butanol (NBA) is produced from NBD and hydrogen gas.
This section consists of the following two process.
(1) NBD Hydrogenation
(2) NBA Distillation
The major reaction of hydrogenation of NBD to NBA is as follow.
CH3CH2CH2CHO + H2 CH3CH2CH2CH2OH
NBD Normal-butanol (NBA)
3.4 IBA Section
In this section, Iso-Butanol (IBA) is produced from IBD and hydrogen gas.
This section consists of the following two process.
(1) IBD Hydrogenation
(2) IBA Distillation
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The major reaction of IBD Hydrogenation of IBD to IBA is as follow.
CH3CH2CH3 + H2 CH3CH2CH3
CHO CH2OH
IBD Iso-butanol (IBA)
4. Mitsubishi Chemical Phosphite Process
4.1 General
Mitsubishi Chemical Corporation (MCC) has developed a new rhodium-bisphosphite (A4N3)
catalyst for the hydroformylation of propylene (PPY), which shows three times higher
catalytic activity than that of the current catalyst based on the rhodium-triphenylphosphine
(TPP) and also has extremely high linear-selectivity and high thermal stability.
4.2 Features of the New Oxo Catalyst
(1) High N/I Ratio
The new bisphosphite ligand, A4N3, increases the N/I ratio remarkably. MCC’s Oxo
catalyst shows the highest linear-selectivity of all of the PPY-hydroformylation processes.
(2) High Thermal Stability
As the A4N3 also has high thermal stability by the introduction of methyl groups in the
bridging biphenol unit, the catalyst can be used at high temperature.
4.3 Application to Other Olefins
(1) Hydroformylation of 2-Butene
2-butene can be hydroformylated to linear valeric aldehyde by using the rhodium-A4N3
catalyst. The catalyst can be applied to the hydroformylation of Rffinate-2.
(2) Hydroformylation of 1-Octene
MCC’s bisphosphite catalysts show the best linear selectivity among all of the well-known
linear-selective catalysts.
For further details, please visit our homepage at:
http://www.mcc-license.com/
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