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Simulated Distillation for Biofuel Analysis

Article  in  Energy & Fuels · December 2009

DOI: 10.1021/ef901295s


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Sigurd Schober
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Energy Fuels 2010, 24, 2086–2090 : DOI:10.1021/ef901295s
Published on Web 12/30/2009

Simulated Distillation for Biofuel Analysis

Christine Bachler, Sigurd Schober, and Martin Mittelbach*
Institute of Chemistry, University of Graz, Austria

Received November 4, 2009. Revised Manuscript Received November 26, 2009

Simulated distillation (SimDis) is a gas chromatographic method and has evolved into an indispensable
tool in petroleum industries to determine the distillation behavior of different petroleum products and to
ensure fuel quality. In contrast to classic physical distillation, SimDis exhibits a range of advantages that
include comparatively very small sample amounts and the possibility of automation, which are of great
importance in fields of research and in the development of novel fuels. Within this work we could show that
SimDis can also be used to characterize not only boiling behaviors of fossil fuels, but also alternative fuels
as different kinds of biodiesel. Analysis of different kinds of biodiesel and biodiesel blends, as presented in
our work, shows that shorter chain fatty acid methyl esters, as can be found in coconut oil, can significantly
change the distillation characteristic to a more favorable distillation curve, which resembles a fossil diesel
fuels boiling behavior. The second part of our work shows that there is a good correlation between data
obtained using SimDis and conventional distillation, also in case of biodiesel. SimDis therefore can easily
be used to classifiy novel biofuels, for example, also bidodiesel made of algae or novel oilseed, regarding
boiling characteristics and quality.

Introduction engine operability, start of the motors, and in the stage of

preheating.10 Recently, the distillation curve is also of main
Although biodiesel nowadays is considered an equal alter-
interest in development of diesel fuel surrogates to ensure
native to fossil diesel fuel,1 there are not only differences in
good engine performance and minimization of pollutants.11,12
chemical composition but also in physical properties. The
For this reason, distillation recoveries at certain temperatures
fatty acid composition of the biodiesel, for example, affects
are defined within the European Standard EN 59013 for fossil
some critical parameters such as cetane number, cold flow
diesel fuel. Unlike mandatory distillation characteristics for
properties, or oxidation stability2 as well as distillation char-
diesel fuel, there is no European standard for distillation
acteristics, which are of main interest in this study. It is already
behavior of biodiesel. However, the United States prescribe
known that biodiesel basically consists of methyl esters of C16
that 90% of a biodiesel or biodiesel blend must be recovered at
and C18 fatty acids with similar boiling points.3 Biodiesel
a maximum temperature of 360 °C according to D 675114 as
therefore exhibits a narrow boiling range around 350 °C with
assurance for the lack of high-boiling compounds. However,
initial boiling points at 300 °C.4 In contrast, fossil diesel
by distillation of biodiesel at atmospheric pressure one faces
additionally contains lower boiling compounds, resulting
the problem that pyrolysis occurs. This results in an unex-
in a steadily increasing boiling behavior starting at 200 °C.
pected decrease of the boiling curve, characterized by a
Generally, high-boiling compounds are connected to engine
decrease of boiling temperature for the last third of the
deposits, increase of exhaust gases, and higher cetane num-
sample, actually characterized by high boiling points.15 To
bers,5-7 whereas a high amount of volatile compounds can
overcome the problem of pyrolysis, distillation can be carried
reduce the flash point of the fuel.8,9 Further, there is a need to
out at reduced pressure as described in ASTM D1160.16
ensure a certain boiling behavior of the diesel fuel due to
Nevertheless, this method as well as other procedures based
on classic physical distillation suffer from poor reproducibility
*To whom correspondence should be addressed. E-mail: martin. and are time-consuming and laborious.17 Another nega- Telephone: þ43 316 380-5353. Fax: þ43 316
380 9840.
tive aspect of a physical distillation process is the lack of
(1) Luque, R.; Herrero-Davila, L.; Campelo, J. M.; Clark, J. H.;
Hidalgo, J. M.; Luna, D.; Marinas, J. M.; Romero, A. A. Energy (10) Encinar, J. M.; Gonzalez, J. F.; Rodriguez-Reinares, A. Ind. Eng.
Environ. Sci. 2008, 1, 542–564. Chem. Res. 2005, 44, 5491–5499.
(2) Ramos Maria, J.; Fernandez Carmen, M.; Casas, A.; Rodriguez, (11) Smith, B. L.; Ott, L. S.; Bruno, T. J. Environ. Sci. Technol. 2008,
L.; Perez, A. Bioresour. Technol. 2009, 100, 261–8. 42, 7682–7689.
(3) Krop, H. B.; van Velzen, M. J. M.; Parsons, J. R.; Govers, H. A. J. (12) Semenov, V. G. Chem. Technol. Fuels Oils 2003, 39, 192–196.
J. Am. Oil Chem. Soc. 1997, 74, 309–315. (13) Kraftstoffe f€
ur Kraftfahrzeuge - Dieselkraftstoff - Anforderun-
(4) Sarma, A. K.; Konwer, D.; Bordoloi, P. K. Energy Fuels 2005, 19, gen and Pr€ufverfahren; Deutsche Fassung EN 590:2009.
656–657. (14) ASTM D6751 - 09 Standard Specification for Biodiesel Fuel Blend
(5) Karonis, D.; Lois, E.; Stournas, S.; Zannikos, F. Energy Fuels Stock (B100) for Middle Distillate Fuels; American Society for Testing and
1998, 12, 230–238. Materials: West Conshohocken, PA.
(6) Karonis, D.; Lois, E.; Zannikos, F.; Alexandridis, A.; Sarimveis, (15) Wenzel, G.; Lammers, P. S. J. Agric. Food Chem. 1997, 45, 4748–
H. Energy Fuels 2003, 17, 1259–1265. 4752.
(7) Bajpai, D.; Tyagi, V. K. J. Oleo. Sci. 2006, 55, 487–502. (16) ASTM D1160 - 06 Standard Test Method for Distillation of
(8) Sjogren, M.; Li, H.; Rannug, U.; Westerholm, R. Fuel 1995, 74, Petroleum Products at Reduced Pressure; American Society for Testing
983–9. and Materials: West Conshohocken, PA.
(9) Mittelbach M.; Remschmiedt C. Biodiesel: The Comprehensive (17) Blomberg, J.; Schoenmakers, P. J.; Brinkman, U. A. T.
Handbook; Boersedruck GmbH: Vienna, 2004. J. Chromatogr. A. 2002, 972, 137–73.

r 2009 American Chemical Society 2086

Energy Fuels 2010, 24, 2086–2090 : DOI:10.1021/ef901295s Bachler et al.

automation; Although one run takes about 40 min in the case Table 1. Fatty Acid Composition of RME and CME in Percent,
of both methods, simulated and physical, the method of Including Methyl Esters at Least Counting 2% (m/m)
choice would be simulated distillation if a series of samples fatty acid RME CME
needs to be analyzed due to high need of manpower for
C8:0 3.5
cleaning of the vacuum apparatus after each run and for C10:0 3.5
control of the whole procedure. Further, rather large sample C12:0 46.3
amounts are needed,18 which might be a problem in research C14:0 15.8
and development laboratories, if new kinds of fuels are only C16:0 7.1 9.0
C18:0 2.2 15.1
available in small volumes. To overcome all those problems, C18:1 58.4 6.1
Eggerston et al.19 first proposed to use a gas chromatographic C18:2 21.4
method to simulate a distillation process. Nowadays simu- C18:3 7.5
lated distillation (SimDis) is a well-established method in
RME is very popular within the European Union. On the
petroleum industry where the knowledge of boiling ranges
other hand, CME seems to be a promising kind of biodiesel;
of crudes and various products is important to determine
First, it contains a high amount of lower-boiling point fatty
quality and to control or optimize different processes in a
acid methyl esters, similar to palmkernel oil,25 indicating that
refinery. Simulated distillation is based on elution of a series
it exhibits a rather wide distillation curve similar to fossil diesel
of n-alkanes introduced into a GC system. Equipped with a
fuel. Second, it is of major interest in the Philippines and
nonpolar column and by linearly raising the oven tempera-
Malaysia, where environmental temperatures are higher and
ture, the alkanes separate in order of increasing boiling points.
therefore cold temperature problems, for example, fuel filter
Simply because the boiling points of all n-alkanes are precisely
or injection line blocking,26-28 can be neglected.
known from literature, a chromatogram received under iden-
Although data obtained via simulated distillation are in
tical conditions can then be divided into boiling ranges and
excellent agreement with actual distillation procedures in the
mimic the physical distillation process. Standardized SimDis
case of petroleum products,18 a comparison of distillation
methods for fossil diesel fuels compromise ASTM D 288720 or
recoveries for a biodiesel sample, as integrated in this work, is
EN 15199-1,21 whereas pure biodiesel or biodiesel blends can
of great interest. The reason is based on the nature of biofuels;
be analyzed according to ASTM D 7398,22 generally covering
In contrast to fossil fuels, which consist of hydrocarbons,
a boiling range from 100 to 615 °C. Although SimDis nowa-
alternative fuels differ in chemical composition. So, especially
days is well established, there is hardly any data on biodiesel
in fields of research and development, the amenities of simu-
distillation characteristics available. Sarma et al.4 performed
lated distillation simplify the procedure to obtain distillation
simulated distillation to analyze a biodiesel made of Koroch
characteristics of novel kinds of fuel, for example, made of
seed oil, characterized by 95% of the sample distilled between
algae oil or new species of oilseed, where sample amounts are
219 and 372 °C (with IBP and FBP at 219 and 430 °C,
small-sized and fast methods are of great importance. As a
respectively). However, a multitude of distillation curves for
consequence of the general trend to create lower-boiling fuels
biodiesel samples still seem to be generated by using classical
in order to reduce emissions, simulated distillation is an
distillation methods, simply because a vacuum distillation
efficient tool for fuel modeling.
apparatus is not always available. A classic distillation pro-
cedure at atmospheric pressure (ASTM D8623), for example,
Experimental Section
was used to test diesel fuel containing 1 and 5 vol % CME
(coconut oil methyl ester), indicating no big differences in Specification of the Fossil Diesel Fuel and Biodiesel Sam-
boiling behavior in contrast to a pure diesel fuel.24 ples. Biodiesel, made of rapeseed oil and obtained from BDV
In this work a comparison of boiling ranges of different (Biodiesel Vienna, Austria), and the coconut oil methyl ester
biodiesel samples and biodiesel blends, obtained by simulated (CME) were prepared according to standard procedures29
distillation, will be shown. It has to be mentioned that there and distilled for further purification. Both biodiesel samples
is hardly any data available, especially in case of widely used were then characterized according to EN 14214.30 The
biodiesel blends that can enormously change in fatty acid results are shown in Tables 1 and 2.
composition. Diesel blends containing certain amounts of The petroleum diesel fuel is a so-called BP ultimate diesel
rapeseed oil methyl esters (RME) were measured, because meeting EN 59013 and contains no FAME. The specification
of this diesel fuel is available via the BP homepage.31
Solvents. The carbon disulfide used for dilution of the
(18) Schwartz, H. E.; Brownlee, R. G.; Boduszynski, M. M.; Su, F.
Anal. Chem. 1987, 59, 1393–401. samples and for preparation of the calibration mixture was
(19) Eggertsen, F. T.; Groennings, S.; Holst, J. J. Anal. Chem. 1960, purchased from Fluka (puriss. p.a., g99,9%). According to
32, 904–9. the scope of the method, cyclohexane can also be used as
(20) ASTM D2887 - 08 Standard Test Method for Boiling Range
Distribution of Petroleum Fractions by Gas Chromatography; American solvent to avoid the use of carbon disulfide in larger volumes.
Society for Testing and Materials: West Conshohocken, PA.
(21) Petroleum Products - Determination of boiling range distribution by
gas chromatography method - Part 1: Middle distillates and lubricating base (25) Dale, A. P.; Meara, M. L. J. Sci. Food Agric. 1955, 6, 166–70.
oils; German version EN 15199-1:2006; CEN: Brussels, Belgium, 2006. (26) Tan, R. R.; Culaba, A. B.; Purvis, M. R. I. Biomass Bioenergy
(22) ASTM D7398 - 07 Standard Test Method for Boiling Range 2004, 26, 579–585.
Distribution of Fatty Acid Methyl Esters (FAME) in the Boiling Range (27) Machacon, H. T. C.; Matsumoto, Y.; Ohkawara, C.; Shiga, S.;
from 100 to 615C by Gas Chromatography; American Society for Testing Karasawa, T.; Nakamura, H. JSAE Rev. 2001, 22, 349–355.
and Materials: West Conshohocken, PA. (28) Kalam, M. A.; Husnawan, M.; Masjuki, H. H. Renew. Energy
(23) ASTM D86 - 09e1 Standard Test Method for Distillation of 2003, 28, 2405–2415.
Petroleum Products at Atmospheric Pressure; American Society for Test- (29) Mittelbach, M.; Koncar, M. Process for Preparing Fatty Acid
ing and Materials: West Conshohocken, PA. Alkyl Esters. Int. Patent Appl. WO/1995/002661, 1994.
(24) National Renewable Energy Laboratory Analysis of Coconut- (30) Kraftstoffe f€
ur Kraftfahrzeuge - Fetts€aure-Methylester (FAME)
Derived Biodiesel and Conventional Diesel Fuel Samples from the Philip- f€
ur Dieselmotoren - Anforderungen and Pr€ ufverfahren.
pines; 2006; (31) BP Global; (Accessed July 17, 2009).
Energy Fuels 2010, 24, 2086–2090 : DOI:10.1021/ef901295s Bachler et al.

Table 2. Physical and Chemical Properties According to EN 14214 C18 acids and by comparison with normal boiling points
presented by Yuan et al.,32 the results were meeting our
prospects. As a second biodiesel sample we chose CME to
ester content [% m/m] 97.4 99.7
density15°C [kg/m3] 883 872
demonstrate the benefits of lower boiling point methyl esters
viscosity40°C [mm2/s] 4.51 3.07 on distillation characteristics. The distillation curve of CME
flash point [°C] 130 120 is very similar to the fossil diesel fuels boiling curve due to the
oxidation stability, 110 °C [h] 10 40 fact that methyl esters of medium chain fatty acids have a
sulfur content [mg/kg] 6 significantly lowered boiling point compared to C18 methyl
cetane number 54
water content [mg/kg] 181 63 esters. Notably, the boiling region compromising 40-75%
total contamination [mg/kg] 9 4 distillation recovery for CME and petroleum-derived diesel
copper strip corrosion (3 h at 50 °C) 1 fuel is characterized by boiling points with a maximum
acid value [mg KOH/g] 0.31 0.13 difference of 10 °C. Further CME exhibits also higher boiling
iodine value [g/100 g] 107 7
methanol content [%(m/m)] 0.09 0.1
point methyl esters elevating the boiling curve. However,
monoglyceride content [%(m/m)] 0.51 <0.001 greater parts of the CME seem to boil within a narrow
diglyceride content [%(m/m)] 0.19 <0.001 temperature range, resulting in a stairway-like distillation
triglyceride content [%(m/m)] 0.01 <0.001 characteristic. Regarding minor distillation recoveries of
free glycerol [%(m/m)] <0.01 0.01 CME, the boiling curve is evaluated compared to the fossil
total glycerol [%(m/m)] 0.16 0.01
Group I metals (Na, K) [mg/kg] <0.2/<0.4 diesel fuels boiling: At 256 °C only 5% of the CME sample
Group II metals (Ca, Mg) [mg/kg] <0.4/< 0.1 can be vaporized whereas nearly 40% of the fossil diesel fuel
phosphorus content [mg/kg] 10 is distilled at the same temperature. However, biodiesel made
of rapeseed oil does not even start to boil at that temperature
The calibration standard was prepared by adding 10 μL of
and shows a boiling point 76 °C higher than CME and even
boiling point calibration sample No. 1, purchased from
136 °C higher than fossil diesel fuel for 5% distillation
Agilent Technologies, to 7 mL of carbon disulfide.
recovery. At 10% distillation recovery the difference be-
Equipment. GC HP 6890 System with a HP 7683 Series
tween the boiling temperature of RME and fossil diesel fuel
Injector. Column: Agilent DB-HT-SIMDIS (5.0 m, 0.53
nearly reaches 150 °C. Although the boiling curve of RME
mm, 0.15 μm). Vakuum distillation apparatus, Herzog
stays elevated, CME otherwise also shows decreased boiling
HDV 632
regions when compared with the fossil fuel. Having a look at
Methods. The simulated distillation used is based on EN
the CME and RME boiling behavior, one can notice that
15199-1. For all of our samples a calibration mixture was
there is an assimilation of the curves at increasing distillation
prepared without the use of polywax, as described in the
recoveries with maximum value of 94 °C at 10% and a
method, due to the fact that the obtained boiling points
minimum difference of 10 °C at 90% distilled off. Consider-
did not exceed 522 °C, representing the boiling point of
ing the U.S. Standard D 6751, the critical value of 90%
tetracontane, the highest boiling alkane of the calibration
distillation recovery at a maximum temperature of 360 °C
can also be met.
Parameters for a conventional distillation under reduced
In the course of our investigations, B10 diesel fuel samples,
pressure using a Herzog HDV 632 distillation apparatus are
containing 10 % m/m of RME or CME, were analyzed using
as follows: volume: 226, 5 mL; temerature at start: 60 °C;
SimDis to refer to a supposable maximum share for biodiesel
distillation rate: 7 mL/min; heating rate: 7 K/min; pressure:
within the European Union. B20 diesel fuel samples where
67 mbar; K-Factor: 12.
generated, as a 20% share is a possible target regarding
Software. SimDis Expert 8.0, Separation Systems.
the US market. Both, B10 and B20 samples show a similar
Results and Discussion boiling behavior compared to petroleum-derived diesel fuel,
which is characterized by a steadily increasing distillation
Distillation Characteristics of Fossil Diesel Fuel and curve (refer Figure 2).
Different Biodiesel Samples. Initially, two kinds biodiesel Until reaching 40% distillation recovery all of the four
(RME and CME), which obviously differ in their fatty acid samples hardly differ in the boiling behavior. Mainly, the
composition, were analyzed according to EN14214 (refer to distillation curve of B10 and B20 containing CME (C10,
Tables 1 and 2). C20) resemble the diesel fuel curve, having a maximum
Afterward, these two biodiesel samples as well as a fossil temperature difference of 14 and 18 °C at 30% distilled off.
diesel fuel (DF) where further characterized using simulated However, great parts of those two samples, approximately
distillation in order to obtain the corresponding boiling 80%, show minimal temperature differences, especially for
behaviors. The resulting distillation curve is obtained by higher boiling parts. The B10 and B20 samples containing
plotting the distillation recoveries against the corresponding RME (R10, R20) are characterized by higher boiling parts
boiling temperatures. As can be seen in Figure 1, the fossil compared to C10, C20, and pure fossil diesel fuel. For R10
diesel fuel shows a steadily increasing boiling behavior meet- and R20 the average temperature difference to fossil diesel
ing EN 590. The boiling behavior of pure RME on the other fuel is about 15 and 20 °C. Nevertheless, R10 shows extre-
hand is characterized by the absence of volatile compounds mely decreased boiling points for lower distillation recov-
resulting in a boiling point more than a boiling curve. eries compared to pure RME. Temperature differences
Considering the distillation recoveries obtained by simu- therefore lie between 41 and 139 °C for both samples until
lated distillation, one can point out that a huge amount of the reaching the 60% distillation recovery mark. At 90% dis-
RME, particularly 80%, boils within 353 and 360 °C. tilled off the temperature difference for R10 and R20 reaches
Assuming that RME primarily consists of methyl esters of a minimum value, 5 and 2 °C, respectively. Considering that
B20 curves, either RME or CME blends, show similar
(32) Yuan, W.; Hansen, A. C.; Zhang, Q. Fuel 2005, 84, 943–950. boiling characteristics, R20 can be preferred to C20 blends
Energy Fuels 2010, 24, 2086–2090 : DOI:10.1021/ef901295s Bachler et al.

Figure 1. Distillation characteristics of fossil diesel fuel and biodiesel made of rapeseed and coconut oil obtained via simulated distillation.

Figure 2. Distillation characteristics of pure fossil diesel fuel (DK), as well as B10 and B20 blends via simulated distillation.

Table 3. CFPP of Pure Biodiesel and Biodiesel Blends even if the scope of the method advises not to use oxygen-
RME CME R10 R20 C10 C20
containing compounds as esters. Starting with distillation
recoveries up to 10%, higher boiling points are obtained with
CFPP [°C] -11 4 -31 -25 -14 -9
conventional vacuum distillation using a Herzog HDV 632
distillation apparatus, as can be seen in Figure 4.
due to the unfavorable cold properties of CME (Table 3).
The region covering 10-90% distillation recoveries, thus
Additionally, RME is more readily available in moderate
climate areas such as in European countries, whereas coco- representing the main part of the sample, shows minor
nut palms grow in tropical areas. temperature differences between 5 and 7 °C. However,
The boiling behavior of two RME samples containing 10 boiling points during that stage start to tend toward elevated
and 20% CME (CR10, CR20) show decreased curves com- data if simulated distillation is used. Finally, the boiling
pared to pure RME and, of course, are elevated when point for 95% distilled shows a maximum in temperature
compared with pure CME (refer to Figure 3). difference with 22 °C. Considering that with simulated
Starting at 5% distillation recovery the boiling points of distillation higher boiling points are created, there can be
the CR samples hardly differ. At 10% distilled off the CR some problems to meet the 90% point mandatory for
mixtures differ most with a significantly higher boiling point biodiesel blends within D 6751, but in the case of our
for CR10. Up to higher distillation recoveries the boiling RME sample the limit is not exceeded. However, simulated
curves of the RME/CME-blends assimilate more and more distillation is an important tool to illustrate the influence of
and start to adapt the pure RME’s boiling curve. Hence, novel fuel surrogates or components within a very short time
temperature differences lie within a small range (3-11 °C) and using generally available laboratory equipment.
for greater parts (30-90% distillation recoveries). Then, the Further, it has to be pointed out that the overall distillation
boiling points at 95% distilled off exhibit a big difference for characteristic is similar to the curve of a physical distillation.
both CR blends again. The IBP (initial boiling point), representing 0.5% distillation
Comparison Simulated and Conventional Distillation. recovery, is 18 °C higher if measured with a vacuum distilla-
Further comparison of simulated and physical distillation tion apparatus. There is no value for FBP (final boiling
was performed by overlapping the associated boiling points point) representing 99.5% distilled off, due to the fact that
and distillation recoveries for the RME sample. This part of the distillation broke up after cracking of the distillation
the work is also very important, because a comparison of residue, definitely a negative aspect of using a conventional
data obtained via those two methods had not been published vacuum apparatus. According to temperature differences
before. However, it is of great importance to manifest obtained by comparing the two methods, further improve-
simulated distillation as a promising tool for fuel analysis ment is needed to adjust higher boiling points in case of
Energy Fuels 2010, 24, 2086–2090 : DOI:10.1021/ef901295s Bachler et al.

Figure 3. Boiling behavior of RME and fossil diesel fuel compared to RME/CME blends via simulated distillation.

Figure 4. Distillation characteristics for RME obtained via simulated (“RME, SimDis”) and conventional, physical distillation (“RME,
simulated distillation. This would imply at least the use of of pure CME as fuel is not favorable in most European
a different method that in fact will not be in accordance to the countries due to bad cold properties. However, by mixing
presented one. CME with RME or diesel fuel the CFPP value can be
decreased to adequate values (see Table 3) even for moderate
climates by maintaining a boiling behavior that still shows
As many other kinds of biodiesel, RME shows a narrow ideal characteristics. A certain amount of lower boiling point
boiling range at temperatures around 350 °C due to the fact methyl esters therefore always needs to be selected by con-
of rather high boiling point components, namely fatty acid sideration of the resulting cold properties of the fuel. Accord-
methyl esters of chain length C16 to C18. In contrast to many ingly, fuel blends containing 10% CME seem to represent a
kinds of feedstock for biodiesel production, coconut oil also good “solution”. Further it could be shown that simulated
contains fatty acids of lower boiling point and therefore CME distillation is a powerful tool in analysis, development, and of
shows a reduced boiling behavior. CME in fact exhibits a course in improvement of different kinds of fuels by using
distillation characteristic resembling a fossil diesel fuel boiling widely available laboratory equipment for reduced time and
behavior. By mixing RME with CME or fossil diesel fuel, the non-negligible potential for automation. In contrast to con-
boiling behavior can be changed, resulting in favorable stea- ventional distillation methods, especially in fields of research,
dily increasing distillation characteristics as lower as well as large amounts of samples as well as costly vacuum distillation
higher boiling point compounds are present. However, the use equipment are needed.


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