TABLE OF CONTENTS

LIST OF FIGURES

LIST OF TABLES

NOMENCLATURE
Symbol

Description

Units

H
E k
Ep
Q
W
Cp

Enthalpy
Kinetic Energy

J/kg
J/kg

Potential Energy
Heat
Work
Constant Volume Specific

J/kg
J/kg
J/kg
J/kg.K

Heat
Temperature change
Volumetric Flowrate
Height
Area
Time
Absolute Humidity

C
M/s
m
m
S
kg water/kg dry air

Density
Humid Volume
Discharge Coefficient
Specific Weight
Gravity
Temperature
Volume
Volume
Time

Kg/m
m3 humid air/kg dry air
0.63
N/m
m/s
degrees celcius
cubic metre
litre
second

T
V
( h )
A
t
( ha)

^
V
CD

g
C
M

1. EXECUTIVE SUMMARY
Nontechnical summary
Encapsulates reason for writing the plan
Tells reader what you want and why, upfront
0.5-1 p

2. LITERATURE REVIEW
10:45
N-nonanal Production

Nonanal is an alkyl aldehyide comprising of nine carbons and a double bonded

oxygen at the terminal. It is identified as a clear, brown liquid with a
characterisitically fruity odour. According to the Pub Chem: Open Chemistry
Database, its industrial uses include as intermediates, odor agents and processing
agents while consumer uses include toiletries, hygienic products, detergents, air
care prouducts and as lubricants. Although it can be found in several essential oils, it
is industrially produced by hydroformylation of 1-octene.
Essentially, hydroformylation is a catalytic conversion process from alkene olefins to
aldehydes. It was originally discovered by Otto Roelen of Ruhrchemie as oxp
synthesis (Frohling C.D., Kohlpaintner, C.W, Bohnen, H.W.). The processes takes
place in the presence of syngas and a transition metal catalyst, as shown in figure 1.
The reaction produces a desired n-product and the undesired iso-product.

Furthermore, Cobalt was the first industrial catalyst of choice but owing to the
requirement of severe processing conditions (i.e. pressure ranges of 200 350 bar),
the industry switched to the more expensive Rhodium catalyst. This allowed for a
simpler process in terms of milder reaction conditions, easier catalyst recovery,
higher yields and efficiency. This is all described by Unveren, H.H.
Today, the water soluble, rhodium catalyst is utilised in the majority of the worlds
hydroformylation process plants. However, as in the case with n-nonanal production,
1

heavier olefins with Carbon counts of around six and higher, are not readily soluble in
water. Thus, this process is not adequate for the processing of these large alkenes.
Currently, various reaction methods are being investigated and implemented on a
small scale such as the temperature dependent multicomponent solvent (TMS)
systems, biphasic flurous systems, ionic liquid systems and carbon dioxide expanded
liquid systems. In order to eventually industrialise the processes in a full-scale
manner, they will have to be competitive environmentally and more importantly,
economically.

Kinetics

The hydroformylation reaction for n-nonanl production is a homogenous, catalytic

reaction as described above. In order to determine the kinetics of this reaction, rate
data needs to be analaysed as described in chapter five of Fogler, H. S.
An exact mechanism has not entirely been agreed on at this stage with the rate
determining step being the variant among sources. However, a generally accepted
diagram of the rhodium-catalysed hydroformylation reaction can be found in various
research papers such as chapter four of Koeken. A.C. (Modelling of the kinetics of 1octene hydroformylation in supercritical carbon dioxide), sufficiently describes this,
allowing for the following reaction network to be established:
Figure 1.. REACTION MECHANISM
Table 1 annotates the symbols and species used within this network.
Table 1

Symb

Species

Formu

ol
A
B
D
E
F
G

Carbon Monoxide
Hydrogen
1-Octene
Octene-Isomers
N-nonanal
Iso-products

Comments

la
CO
H
Reactant
Desired Product
Branched
Aldehydes

H
Rh

N-Octane
Rhodium Complex

The following rate laws have been adapted from Koeken, A.C., as well as Deshpande
R.M. and Chaundhari R.V.. Equation 1 toEquation 3 described the heterogenous
hydroformylation steps, based on the Langmui-Hinshelwood models.

r 1,hf =

k 1,hf [ A ][ B ] [ D ][ Rh ] (1+ K 1, L [ L ] )

Equation 1

( 1+ K 1, A [ A ] ) ( 1+ K 1, D [ D ] )

r 2,hf =

k 2,hf [ A ][ B ] [ D ][ Rh ] (1+ K 2, L [ L ] )

( 1+ K 2, A [ A ] ) ( 1+ K 2,D [ D ] )

r 3,hf =

Equation 2

k 3, hf [ A ][ B ] [ E ][ Rh ]

Equation 3

( 1+ K 3, A [ A ] ) ( 1+ K 3, D [ E ] ) ( 1+ K 3,L [ L ] )

The isomerisation steps and the hydrogenations steps were approximated to be first
order as described by Equation 4Equation 5Equation 6 and Equation 7.

r 4,i =k 4, i [ D ] [Rh]

Equation 4

r 5,i=k 5,i [ E ] [Rh]

Equation 5

r 6,hg =k 4,i [ B] [ D ] [ Rh]

Equation 6

r 7,hg=k 4,i [ B ] [ E][Rh]

Equation 7

Next, the mol balances for each species is described using the design equation for a
batch reactor.

It is assumed..

d[A]
=r 1,hf r 2,hf r 3, hf
dt
d [B]
=r 1,hf r 2,hf r 3,hf r 1,hg r 2,hg
dt
d [D]
=r 1, hf r 2, hf r 3,hf r 1,i +r 2,i
dt
d [E ]
=r 2,hf r 3,hf +r 1,ir 2,i
dt
d [F ]
=+r 1,hf
dt
d [G]
=+ r 2,hf +r 3,hf
dt
d [H ]
=+ r 1,hg+ r 2,hg
dt
d [Rh]
=0
dt
d [L 1]
=0
dt

Equation 8
Equation 9
Equation 10
Equation 11
Equation 12
Equation 13
Equation 14
Equation 15
Equation 16

From Koeken, it is expected that the reaction order is . P.78

Materials and Solvents

Reactor Type
Operating Conditions
Cost Evaluation
Environmental Review

3. Conceptual Design
t(0) = 0
t(f) = 36000

4. REFERENCES
Cengel, Y. A., Cimbala, J. M. 2014. Fluid Mechanics: Fundamentals and
Applications. Singapore: Mc Graw Hill Education.
Felder, R., Rousseau, R. 2005. Elementary Principles of Chemical Processes. United
States of America: Wiley & Sons, Inc.
Pauloccui, A. 2002. Cooling Tower Analysis. University of Tennessee at Chattanooga.
United States of America.
Schwedler, M. 2014. Effect of Heat Rejection Load and Wet Bulb on Cooling Tower
Performance

National Center for Biotechnology Information. PubChem Compound Database;

CID=31289, https://pubchem.ncbi.nlm.nih.gov/compound/31289 (accessed Aug. 9,
2015).

Frohling, C. D.; Kohlpaintner, C. W.; Bohnen, H.-W., Carbon monoxide and

synthesis gas chemistry - hydroformylation (Oxo synthesis, Roelen reaction). In
Applied homogeneous catalysis with organometallic compounds, Cornils, B.;
Herrmann, W. A., Eds. Wiley-VCH: Weinheim, 2002; Vol. 1, pp 29-103.
Unveren. H.H. 2004. Hydroformylatino of long chaing olefins in microemulsion. University
of Berlin. Germany.
R. M. Deshpande, R. V. Chaudhari, Ind. Eng. Chem. Res. 1988, 27, 1996-2002.
Koeken, A.C. 2008. Homogeneously Catalysed Hydroformaltion in supercritical
carbon dioxide: kentics, thermodynamics and membrane reactor technology for
continuous operation. Technical University of Eindhoven.