Paradigm shift in Chemical Engineering

education, processes and technology

Seperation of olefins/paraffins by using polymeric membranes

JAIMIN PANDYA

ABSTRACT

Propylene/propane via cryogenic distillation is extremely energy-intensive, and membrane separation may provide an
attractive alternative. In this paper, Propylene/propane separation performance using polymeric membranes is
summarized,and an experimental Propylene/Propane polymeric upper bound based on literature data is presented. A
theoretical prediction of the Propylene/Propane upper bound is also presented, and shows good agreement with the
experimental upper bound. Further, two ways to overcome the Propylene /propane upper bound, based on increasing the
sorption or diffusion selectivity, is also discussed, and a review on advanced membrane types such as facilitated transport
membranes,zeolite and metal organic framework based membranes, and carbon molecular sieve membranes is
presented.Of these, carbon membranes have shown the potential to surpass the polymeric Propylene/propane upper
bound performance.Furthermore, a convenient, potentially scalable method for tailoring the performance of carbon
membranes for Propylene/propane separation based on tuning the pyrolysis conditions has also been demonstrated.

C2H4 permeability for polymeric membrane materials, and the limit to

1. INTRODUCTION
Propylene is the second most important feedstock in the
petrochemical industrybehind ethylene . Major propylene
derivatives include plastics (polypropylene
PP),acrylonitrile, propylene oxide, cumene/phenol, oxo
alcohols, acrylic acids, isopropylalcohol, oligomers and
other chemicals, which enable the manufacture of other
chemical sand plastics. Propylene and propane are found in the low
and middle fractions of the distillation process, albeit in small amounts.
Large amounts are formed when gasoline is made by cracking or
reforming. The separation of these two has been relatively more difficult
than that of other gas pairs, mainly ascribed to their close thermodynamic
and physical properties. Ethylene/ethane (C2H4/C2H6) separations are
currently carriedout using energy intensive distillation operations,1,2
andhave long been identified as applications where low-energyseparation
replacements could provide very large (on theorder of 1012 Btu/y)
reductions in energy consumption.1,35
Alternative less energy-intensive separation technologies,such as
membranes, adsorption, absorption and extraction,have been important
areas of research, and the concept of hybrid systems has drawn significant
attention. The use of membranes has been the focal point of research as a
new means of olefin/paraffin separation due to its lower operating and
capital costs. In this article, a comprehensive review is presented for the
application of polymeric membranes in light olefin/paraffin separation
with example of propylene/propane separation. Conventionalpolymeric
membranes cannot achieve the productivity(permeability) and efficiency
(selectivity) combinationsrequired for C2H4/C2H6 separations.912 In
this regard,understanding the tradeoff between C2H4/C2H6 selectivity vs.
this tradeoff defined by hyper-rigid glassy polymers,can allow exploring
options for new high-performing membrane materials for C2H4/C2H6
separations.
1.1Theory and Background
Transport of gases through polymers occurs according to the
solution-diffusion theory .Gas molecules are introduced at
the high pressure upstream side of themembrane where they
sorb into the membrane. The amounts of sorption depend
on thematerial and the gas penetrants. Gas molecules then
diffuse through the membrane to thelower pressure side
where they then desorb. Thermodynamic equilibrium on either
side of the membrane is also considered during the
transport process. The permeability (productivity) of a membrane is
defined as the pressure and thickness normalized flux
NA l
PA= (1)
D
p
where p is the pressure difference across the membrane
between upstream anddownstream and l is the thickness of the
membrane and
Na is flux. The most common unit for permeation is Barrer
where 1 Barrer = 10-10 cc.(stp)/(cm2.sec.cmHg).

Permeability can further be represented as the product of a

thermodynamic sorption coefficient (_SA), and a kinetic diffusion
coefficient (DA).

Table 1.1: Thermodynamic properties of Propylene and Propane. PA=DASA (2)

Molecular Molecular Weight Boiling Point Critical Temp.
Formula (g/mol) (K) (K) For a selected gas pair, the separation factor or the selectivity (the
Propylene C 3 H6 42 226 365.2
Propane C3H8 44 230.4 369.9
E-mail address & contact detail of author to be provided
2

efficiency of a membrane) can be expressed as the ratio of the mole
fractions of the two gas penetrant components A and B in the
downstream and upstream yi and xi respectively,
Plasticization of membranes
Propylene and propane tend to plasticize glassy polymers even at a very
low pressure (p = 2 bar) [18]. Plasticization occurs as a result of swelling

in the polymer, leading to a result an upswing in the propylene or propane

.

( yA / yB ) permeability. Plasticization usually undermines the selectivity. It is

AB = (xA / xB )
believed that as the sorption uptake in dissolved mode increases leading

with a negligible downstream pressure compared to the upstream. to a significant swelling in the matrix This swelling causes an increase in

the fractional free volume (FFV) of the polymer. Due to this swelling, a
.For a particular gas pair penetration, respective permeabilities are
significant increase in segmental motion is observed. This is reflected by
the productivities of the particular gases and the selectivity is the
an upturn in the permeability-pressure plot for a particular gas pair and
efficiency of that gas pair.
both sorption and diffusion coefficients may deviate from the simple dual
SORPTION
mode expressions described earlier in such case. The upturn pressure is
The sorption in glassy polymers is represented by a dual mode model,
known as the plasticization pressure. Although the permeability increases
which accounts for penetrants in the normally densified and microvoid
for a plasticized membrane, the selectivity decreases significantly due to
regions of the polymer matrix. Specifically, the model accounts for the
the loss of diffusivity selectivity. In other words a plasticized membrane
differences in gas transport properties in both the idealized Henrys law
becomes less size selective. Figure-2.4 shows the response of a typical
and Langmuir domains of a glassy polymer The Langmuir concentration

CHA, for gas A, describes sorption in the microvoid or holes plasticized membrane. As shown in Figure-2.4, the permeability takes an

throughout the matrix, which are the packing defects in the non- upturn (propylene permeability is the red curve) and the selectivity

equilibrium glassy matrix. The sorption in glassy polymers is given by , decreases beyond the plasticization pressure. Propylene and propane,

both being condensable, tend to plasticize polymeric membranes in case

CA = CDA + CHA
of a condensable membrane, since the amount of sorbed gases is much
Where Cda is henry law expression and Cha is Langmuir expression.
higher, the swelling of a matrix occurs at much lower partial pressures.
DIFFUSION

Gas molecules diffuse through a dense polymer membrane by random

jumps from one position to the other. The schematic of diffusion is

shown in Figure below in which is the average length of random

diffusion jump.

Polymers for Propylene/Propane seperations

Polymers provide a range of desirable properties that are important for gas
The rate of diffusion for a particular gas molecule depends on the separation processes including low cost, high permeability, good

frequency and the length of the random diffusion jump. In polymers, this mechanical stability, and ease of processing. However, polymeric

is governed by the thermal fluctuations, which vary according to the membranes based on rubbery polymers have very low selectivity for

polymeric chain structures. In case of glassy polymers, the thermal olefin/paraffin (especially propylene/propane) separations. Tanaka et al.

volume fluctuation is low giving much higher diffusion selectivity. reported a selectivity of 1.7 for a polybutadiene membrane at 50 0C

permeation temperature [29]. Ito et al reported a propylene/propane

selectivity of 1.0 with silicone rubber membrane [30].

 propylene/propane separations exhibit plasticization at a very low

pressure (2-4 bar).As mentioned in the previous section, a successful

A polymer material with a high glass-transition temperature (Tg), high
melting point, and negligible crystallinity is generally preferred. Glassy systematic annealing approach has been taken in this research to
polymers (i.e., polymers below their Tg) have stiffer polymer backbones suppress plasticization .
and therefore force relatively larger molecules permeate the membrane
more slowly. To increase the membrane selectivity, either the diffusivity
or the solubility needs be enhanced. A rather general trade-off exists
between permeability and selectivity is known as a polymer upper bound
limit. Robeson, in 1991, defined the upper-bound of polymeric Polymer Material Selection and Synthesis
membranes for gas pairs such as O2/N2, CO2/CH4, H2/CH4, and others.
In 2001, Burns and Koros identified the upper bound for C3H6/C3H8 Polymeric materials studied in this work were synthesized in the
separation at 35C (Figure 2.7) [31]. The data were taken from a number
laboratory. The material selection process was based on the transport
of research studies and matched with a mathematical model. Table-2.1
C3H properties of the polyimide for propylene/propane separations. Previous
Temp Feed P C3H6 6/
Polym C3 researches have shown initial promising results with 6FDA-Durene
Author er (oC) Pressure (Barrer) H8
Staudt- 6FDA- polyimide and 6FDA-Durene/DABA co-polyimide polymer [1, 2] that
Bickel mPD 35 3.8 atm 0.13 10
and Koros were promising. Bulky CF3 groups of these monomers provide molecular
Staudt- 6FDA-
spacing, which is necessary to tune the selectivity of the polymer.
Bickel IpDA 35 3.8 atm 0.58 15
and Koros Moreover, this was also one of the highest performing polymers in the
Staudt- 6FDA-
Bickel 6FpDA 35 3.8 atm 0.89 16 upper-bound curve for propylene/propane separations [1]. Figure-3.1
and Koros
Matrimid shows the upper bound curve for this particular gas separation A
Burns and 35 2 atm 0.10 10
Koros polycondensation reaction method was used for the synthesis process. To

Burns and 6FDA- increase the molecular weight and the polydispersity index of the
33DMD 35 1.1 atm 0.15 13.2
Koros B polymer, synthesis conditions were modified.
6FDA-
The 6FDA-Durene polyimide, 6FDA-Durene/DABA (9/1) co-polyimide,
Tanaka et TrMPD
al. 50 2 atm 30 11 and 6FDA-Durene/DABA (7/3) co-polyimide were synthesized via a
(DAM)
Okamoto two-step chemical imidization in an NMP solution. For the preparation
[3 et 6FDA-
of polyamic acid, a designated molar ratio of Durene and DABA diamine
2] DDBT 50 2 atm 1.8 20
al. was dissolved in NMP under a nitrogen atmosphere and then an
[2 Tanaka 6FDA-
9] et al. DDBT 50 2 atm 0.76 27 equimolar of solid 6FDA was gradually added to the solution in a
shows a selected summary of pure polymer permeabilities and
moisture free flask with a magnetic stirring under a nitrogen atmosphere
selectivities for this particular gas pair [31].
A significant amount of research has been done on glassy polyimides at room temperature. The reason of adding solid 6FDA gradually is to
for propylene/propane separations [28-32]. Among all these, polyimides
based on 4,4-(hexafluorisopropylidene)dipthalic anhydride (6FDA) have suppress the reaction between water and 6FDA. Aromatic dianhydrides
exhibited the best performance. The upper bound is currently defined by
can react with water and other impurities in the amide solvents, but have
the 6FDA-based polymers prepared from the TrMPD (DAM) and DDBT.
The report showed an increase in selectivity with a decrease of a slower reaction rate relative to their reacting with diamines. Therefore,
temperature from 308K to 298K; however, as noted earlier strong gradually adding the solid 6FDA reduces its availability for competing
plasticization effects were seen at very low pressure for propylene at
reactions with water or other impurities, thus leads to a higher
lower temperature. In 50:50 propane/propylene mixed gas experiments,
conversion and molecular weight [1]. After reacted for 24 h, a high
the selectivity decreased with increasing feed pressure by as much as
molecular weight polyamic acid was formed. Then for the chemical
50% from ideal selectivity. Similarly most of the membranes for
4

imidization step, a mixture of acetic anhydride and triethylamine at 4:1 gas sorption experiments using a pressure decay method with un-

molar ratio was slowly added to the polyamic acid solution to perform annealed and annealed films have been discussed. These sorption

imidization for 24 h under nitrogen atmosphere. Finally, the co- experiments have been used to analyze the permeation data using the

polyimide was precipitated in methanol, filtered, washed and dried at dual-mode model. Mixed gas permeation results also have been explained

120 C in vacuum for 24 h. The schemes of co-polyimide synthesis and with dual mode and bulk flow transport models.

chemical structure of this co-polyimide are shown in figure using italics. Weights and measures should be expressed in SI units. All
non-standard abbreviations or symbols must be defined when first
mentioned, or a glossary provided.

Plasticization Suppression

High Test Temperature Effect On 6FDA-

6FpDA

6FDA-6FpDA films were solution casted with dichloromethane as the

solvent and dried at 1100C in a vacuum oven for ~20 hours. Initial
permeation tests were done at 350C and around 2 atm to compare our
results with previous works. Pure gas permeation test results are shown in
Table-5.2 with some of the previous results. The results in Table-5.2 are
in good agreement with that seen by Burns and Koros and Sejour and

: The synthetic scheme and chemical structure of co-polyimide

Temperatu PC3H
Pressure re 6

PERFORMANCE OF FOR 6FDA-Durene (Barr C3H6/C3

polyimide and 6FDA-Durene/DABA co- (psia) (0C) er) H8
polyimide This
PROPYLENE/PROPANESEPARATIONS Study 29.4 35 0.850.05 170.5
Sejour
The first part of this chapter describes the challenges faced by
and 29.4 35 0.92 16.4
previous researchers with 6FDA-6FpDA polyimide for Koros
propylene/propane
[3]
Burns
separations due to plasticization. A study on pure film annealing
and 29.4 35 0.89 16.0
temperature has been shown here to optimize and standardize further Koros
test conditions to avoid any anomalies. Plasticization suppression was
[2]
Koros [2, 3].
achieved by performing high temperature permeation on properly In this case a small decrease in permeability with an increased
annealed dense films made with high molecular weight polymer. A selectivity was observed. Polymer permeabilities and selectivities are
detailed analysis of pure gas and mixed gas results using different known to vary with the polymer synthesis and post drying conditions.
permeability models has been shown in this chapter. The annealing Since the results mentioned in this research are obtained with a

effects in terms of plasticization suppression, permeability and selectivity modified imidization approach, it was expected that the results might

have been discussed in detail. According to our best knowledge, this is be little different than seen by others. This difference in the

for the first time plasticization suppression for propylene/propane has permeability and selectivity is perfectly within the acceptable range

been reported with any polyimide dense film membrane. Results of pure and were reproducible. To test the reproducibility, at least three
permeation tests were performed with each gas at a particular

pressure. If the results were within 5-8% error range, it was

considered to be reproducible. Oxygen and nitrogen permeabilities

were also measured as benchmark gases. Table-5.3 shows these

4
results at 350C.
Pressurizati
Temper on Isotherm
Pressure ature PO2 3 Depressuriz
(Ba . ation Points
Conditi rrer 5
on (psia) (0C) ) O2/N2
17.0 4.2 3
Pure gas 29.4 35 0.6 0.4 2
.
5

High test temperature permeation tests were

performed after successfully reproducing propylene/propane 2

0 1
results at 35 C. As noted earlier, at this point, it was
.
hypothesized that permeation at elevated temperature (in this 5

case 700C) will delay the effect of plasticization. Figure-5.3 1

1 2 3
4 5
shows the propylene isotherm obtained with 700C permeation
0 0 0 0 60
test temperature. At high temperatures the solubility Press
ure
coefficient decreases, thereby decreasing the permeability (psia)
Figure-5.3: Propylene permeability isotherm at 700C. propylene
and hence suppressing plasticization, so it was expected that pressurization, propylene de-pressurization

performing permeation at a higher temperature would

. Annealing Effect On Pure Gas Permeation
suppress the plasticization to a higher pressure.Figure-5.3

clearly indicates that there is plasticization with propylene

Table-4 shows the result of this annealing effect on
even at 700C. This result was unexpected under these test
oxygen/nitrogen. The annealing effect is prominent with
conditions. Moreover in this case, the onset of plasticization
oxygen/nitrogen data in Table-5.4. Permeability of oxygen
is earlier than 3 atm (2.5 atm) as reported by Staudt-Bickel
decreased with increasing annealing temperature, whereas the
[1]. One of the main differences between these two
selectivity of oxygen/nitrogen increased.
experiments was the casted film drying temperature. While in
This phenomenon is typical for the annealing effect by which
Staudt-Bickels cast films were annealed above 200C for
polymer chains become more relaxed and hence more densified as
several hours, in this study the films were dried at 110C for
we increase the annealing treatment temperature. Based on these
several hours. To probe more into these results, a detailed

study of the post treatment conditions was conducted. results, it was decided to follow annealing temperature of

Annealing studies were performed in which exposure to >

2000C for 24 hr. was compared to 1100C and 1500C for

roughly an equivalent period.

6

temperature.

P C3H
C3
Pressur H6
6/C3

Temper Drying Test e (B H8

Pressure ature PO2 Conditi Tempe arr
Anneali er)
0 on rature
ng (atm) ( C) (Barrer) O2/N2 (psi)
Condition
(0C)
1.0 170.
0 0
17.01. 110 C 35 C 29.4 0.05 8
1100C 29.4 35 0 4.20.4 0.7 191.
2100C 350C 29.4 0.05 0
16.50.
1500C 29.4 35 8 4.50.2 2.21
1100C 700C 29.4 0.1 12.0
16.20. 0.96 13.0
2100C 29.4 35 4 4.70.4 2100C 700C 29.4 0.08 0.5
16.00. 4.80.
2200C 29.4 35 5 2 Similar trends were observed with propane permeation as well. 6FDA-

6FpDA did not plasticize up to 70 psi upstream pressure. The

This phenomenon is typical for the annealing effect by which
depressurization isotherm also suggested no indication of plasticization
polymer chains become more relaxed and hence more densified as we

increase the annealing treatment temperature. Based on these results, effect. This result suggests that suppression of plasticization was indeed

it was decided to follow annealing temperature of 210 0C for 18-20 achieved by annealing the films and performing permeation experiments

hours for all experiments onwards to maintain consistency. From this at 700C. While this is for the first time we observed plasticization

point, any film dried at 1100C will be referred to as un-annealed, suppression of propylene with 6FDA-6FpDA up to 70 psi upstream

and films dried at 2100C as annealed. Table-5.5 summarizes the pressure, as mentioned earlier, mixed gas composition experiments are

propylene/propane annealing results with different permeation test the real tests for plasticization suppression. The next section describes the
temperatures. In the case of propylene/propane separations also we results from mixed gas experiments.
saw a decrease in permeability and increase in selectivity after

annealing.

Figure-5.4 shows the successful plasticization suppression results

with annealed 6FDA-6FpDA films at the 700C test temperature. At

least three films from different casted films were tested for each

pressure point. The results were within 5% error range. After each

pressurization isotherm, depressurization points were also noted and

compared with the corresponding points. Unlike un-annealed films,

annealed films did not show any plasticization effect up to 70 psi

upstream pressure. Figure-5.5 shows the pressurization and

depressurization behavior of both propylene and propane at 70 0C test


MIXED MATRIX MEMBRANES WITH
6FDA-6FPDA AND ALPO-14
mixed matrix membranes were formed with 6FDA-6FpDA as the
polymer matrix and AlPO-14 as the molecular sieve material. AlPO-14
was chosen due to its success with PSA and VSA for propylene/propane
separations. AlPO-14 is a unique molecular sieve which is one
dimensional for propylene and almost excludes propane from entering the
interior cage. Permeation results with pure and mixed gases at 35 0C
showed very promising enhancements in both propylene permeability and
propylene/propane selectivity. According to our best knowledge, this is
the first time enhanced selectivity and permeability were achieved in a
mixed gas environment for this gas pair using the mixed matrix hybrid
material approach. The main observation we would like to highlight was
the excellent polymer-sieve matching. A 6FDA-6FpDA-AlPO-14
combination holds a bright future for large scale propylene/propane
separations.
Cross-linkable dual-layer hollow fiber
membranes comprising -Cyclodextrin
In this work cross-linkable co-polyimide dual layer hollow
fiber membranes with high gas separation performance for
CO2/CH4 and C3H6/C3H8 have been fabricated. The effects of
spinning and thermal treatment conditions on the gas
separation performance of these membranes were investigated.
Experimental results show that permeances decrease with
increasing take-up velocity. Before silicon rubber coating,
higher selectivities can be obtained by increasing take-up
velocity from 4 to 7.4 m/min. A further increase in take-up
velocity to 11.8 m/min results in lower selectivities due to
defect formation. On the other hand, after silicon rubber
coating, the CO2/CH4 and C3H6/C3H8 selectivities increase as
the take-up velocity increases. In addition, permeances increase
with a reduction in outer-layer dope flow rate due to the thinner
skin layer and lower transport resistance. However,
selectivities decrease when the outer-layer dope flow rate
decreases owing to defect formation.
For as-spun (i.e., pristine and without heat treatment) fibers,
the optimal spinning condition was found to have a take-up
velocity of 7.4 m/min with an outer layer dope flow rate of 0.5
ml/min. The resultant fiber shows a CO2/CH4 selectivity of
6.22 and 14.3 before and after silicon rubber coating,
respectively and also C3H6/C3H8 selectivity of 6.52 and 12.9
before and after silicon rubber coating, respectively.
Thermal treatment temperature plays a significant role on fiber
morphology. Fiber diameters shrunk after treatment. The 350
C treated fibers show higher permeances and lower
selectivities close to those of untreated fibers, while the 400 C
treated fibers show higher selectivities but lower permeances
due to the skin densification and a higher degree of cross-
linking. As a result, the silicon rubber coating has a less effect
on the 400 C treated fibers than the 350 C treated fibers.
For CO2/CH4 separation, without silicon rubber coating,
sample D-400-BSRC show the best CO2/CH4 separation with a
CO2 permeance of 130 GPU and a selectivity of 15.5. After
silicon rubber coating, sample C-400-ASRC shows the best
selectivity of 20 and a CO2 permeance of 82 GPU. For
C3H6/C3H8 separation, without silicon rubber coating, sample
D-400-BSRC show the best C3H6/C3H8 separation with a C3H6
permeance of 73 GPU and a selectivity of 10.5. After silicon
rubber coating, sample B-400-ASRC shows the best selectivity
of 15.3 and a C3H6 permeance of 29 GPU.
Thermal cross-linkable co-polyimide/ZIF-8
mixed matrix membranes
we aimed to synergistically combine the strengths of ZIF-8
and cross-linkable polyimide and to molecularly design
MMMs for natural gas purification and olefin/paraffin
separation. In this work three 6FDA-based cross-linkable co-
polyimide/ZIF-8 mixed matrix membranes with high gas
separation performance for CO2/CH4 and C3H6/C3H8 were
fabricated. The effects of ZIF-8 nano-particles and thermal
treatment conditions on gas separation performance of these
membranes have been investigated. The following conclusions
can be made. Experimental results show that permeability for
all gases increases rapidly with increasing ZIF-8 loading due
to the additional free volume provided by ZIF-8 particles and
increased distance among polymer chains. Ideal C3H6/C3H8
selectivity improves visibly with increasing ZIF-8 loading due
to the inherently high selectivity of ZIF-8 for C3H6/C3H8
separation. Similar to other works, the addition of ZIF nano-
particles into the polymer matrix mainly increases the
permeability (i.e., not selectivity) for CO2/CH4 separation
because of their small gas diameters and good interactions
with ZIF-8.
8

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