Sustainable Chemistry and Pharmacy 12 (2019) 100144

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Sustainable Chemistry and Pharmacy

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Liquified dimethyl ether (DME): A green solvent for the extraction of hemp T
(Cannabis sativa L.) seed oil
Afraz Subratti, Lorale J. Lalgee, Nigel K. Jalsa∗
Department of Chemistry, The University of the West Indies, St. Augustine Campus, Trinidad and Tobago

A R T I C LE I N FO A B S T R A C T

Keywords: The remarkable nutritional value and health benefits of hemp seeds and their oil extract are well documented. In
Dimethyl ether this study, we explored the use of liquefied dimethyl ether (DME) as a method for obtaining hemp seed oil from
Green solvent hulled hemp seeds. The resulting yields were higher using this ether in comparison to conventional organic
Extraction solvents. The oil was acquired in high purity, with its fatty acid content characterized via 1H NMR analysis. The
Cannabis
process developed is simple to set up, cost effective, does not require using a rotary evaporator; and importantly,
allows for facile recovery of the DME without traces of solvent remaining in the crude.

1. Introduction effective in the treatment of glaucoma (Järvinen et al., 2002), cancer

Cannabis sativa L., commonly referred to as Hemp (or Marijuana,
depending upon the THC content), is an annual herbaceous plant be-
longing to the Cannabaceae family (Kymäläinen and Sjöberg, 2008;
Russo, 2007). Although indigenous to central Asia and the Indian
subcontinent, the plant strives in a variety of climates around the world;
and is typically cultivated for its edible seeds and bast fibre (Russo,
2007; Xiaoli et al., 2015). The dicotyledonous hemp seed is known for
being oil rich (Calloway and Laakkonen, 1996); whereas the cortex of
the plant produces one of the most durable/strong cellulosic natural
fibers (Cronier et al., 2005). Hemp is regarded as a ‘cash crop’ as it finds
a plethora of applications particularly in the medicinal and textile in-
dustry (Zanetti et al., 2013).
Throughout recorded history, hemp seeds and their oil extract have
been recognized for their exceptional nutritional value and health
benefits (Matthäus and Brühl, 2008; Small and Marcus, 2002). The seed
is known for being a rich natural source of several of the important
vitamins and minerals, as well as β-carotene (Small and Marcus, 2002).
The general composition of essential nutrients are: 20–30% carbohy-
drates, 20–35% proteins, 25–35% oil and ∼15% insoluble fibers
(Deferne and Pate, 1996; Mihoc et al., 2012). Almost 80% of the oil is
comprised of polyunsaturated fatty acids (PUFAs), being especially rich
in essential fatty acids (EFAs) such as α-linolenic acid (18: 3 ω-3) and
linoleic acid (18: 2 ω-6) (Mihoc et al., 2012). Present in the oil to a
lesser extent, but also factoring into the overall beneficial effects, are
terpenes and cannabinoids (Callaway, 2004). Apart from their nutri-
tional significance, hemp seeds and their oil extract have proven
(De Petrocellis et al., 2000), constipation (Cheng et al., 2011), high
blood pressure (Kunos et al., 2000) and cholesterol levels (Kunos et al.,
2000); as well as demonstrating immunomodulatory (Mustafa and
McKinnon, 1999), dermatological disease amelioration (Montserrat-de
la Paz et al., 2014), antioxidant (Chen et al., 2012) and antiaging effects
(Chen et al., 2012). In more recent times, the likelihood of hemp being
an energetic crop in the production of bioethanol and biodiesel has
been investigated (Ahmad et al., 2011).
Most commercially available hemp seed oil is produced via cold
pressing, due to its inexpensiveness in mass production (Anwar et al.,
2006). However, various other methodologies have also been devel-
oped for its production. These include the use of extraction solvents
such as ethanol (Bomgardner, 2018), n-hexane (Kostic et al., 2013), and
petroleum ether (Kostic et al., 2013); and techniques employing the use
of supercritical carbon dioxide (sCO2) (Da Porto et al., 2012a, 2012b),
or microwave assistance (Chang et al., 2017). Even though effective and
optimized in some cases, these existing methodologies still suffer from
several drawbacks (Kostica et al., 2014). Ethanol extracts chlorophyll
simultaneously which adds an additional step in obtaining the pure oil.
The typical solvents used are hazardous to humans and the environ-
ment (Szekely et al., 2014); and present a challenge for their complete
removal from the oil. The major issues with using olive oil is that it
requires heating and the extracts cannot be concentrated (Szekely et al.,
2014). The sCO2 and microwave techniques require the use of ex-
pensive equipment that may not be available in a typical laboratory
(Perrut, 2000).
Over the years tremendous efforts have been focused towards the

∗
Corresponding author.
E-mail address: nigel.jalsa@sta.uwi.edu (N.K. Jalsa).

https://doi.org/10.1016/j.scp.2019.100144
Received 6 January 2019; Received in revised form 5 April 2019; Accepted 6 April 2019
2352-5541/ © 2019 Elsevier B.V. All rights reserved.
A. Subratti, et al. Sustainable Chemistry and Pharmacy 12 (2019) 100144

Fig. 1. Experimental set-up for stirring (left) and continuous flow (right) extractions.

to similar fuels (Good et al., 1999). DME has also been utilized as an
aerosol propellant and serves as a synthetic building block to other
chemicals (Aguayo et al., 2007; Furukawa et al., 2016). Its ability to act
as an extraction solvent has been investigated in removing proteins and
pigments derived from vegetable tissues (Furukawa et al., 2016), es-
sential oils from citrus peels (Hoshino et al., 2014), and lipids from
biomass (Catchpole et al., 2010). Owing to the high miscibility of water
in DME, it facilitates a highly efficient dewatering process as demon-
strated with brown coal (Kanda and Makino, 2014) as well as from
blue-green microalgae (Kanda and Li, 2011; Kanda et al., 2012; Kanda
et al., 2013).
Most recently our group reported the use of DME as a reaction
solvent in the synthesis of O-alkyl trichloroacetimidates, for which ex-
cellent yields were obtained (Subratti et al., 2018). In this present study
we explored the ability of liquefied DME to act as green extraction
Fig. 2. Graph showing yields of oil extracted from unground and ground seeds. solvent in the production of hemp seed oil, on a laboratory scale level.
To the best of our knowledge this is the first report of DME being used
Table 1 to extract hemp seed oil. We utilized commercially available hemp
Percentage yield of hemp oil extracted. seeds and a simple economical laboratory set-up in our experiments.
Hemp Seed Percentage Yield (%)
2. Materials and methods
Duration of Extraction (minutes) Pet-ether n-Hexane
2.1. Materials
10 20 30 40 50

-Unground 13 19 24 25 25 17 19 The food-grade hulled hemp seed and commercially available hemp
Ground 16 24 29 31 31 23 26 seed oil were purchased from a popular international seller from
Canada. The DME was obtained from Caribbean Gas Chemical Limited;
and the other reagents from Sigma-Aldrich Ltd.
use of renewable energy sources, minimization of environmental pol- The following terminologies used throughout the manuscript are
lution, and combatting global warming. Dimethyl ether (DME) having a defined below:
high cetane number and favourable carbon/oxygen ratio emerged in
the spotlight as a cleaner, environmentally friendly, and high efficiency Unhulled seeds: seeds with the outer shell intact
ignition fuel (Semelsberger et al., 2006; Arcoumanis et al., 2008; Li and Hulled seeds: seeds with the outer shell removed
Makino, 2014). This simple ether is non-toxic, benign, can be derived Ground seeds: hulled seeds that were grounded to finer pieces
from biomaterial, easier to transport, and relatively cheap as compared Unground seeds: hulled seeds

Table 2
Percent fatty acid content in hemp oil determined from 1H NMR.
1
Fatty acid (ester) H NMR Spectra (Figs. 3–6) (δ ppm): integral value Reference glycerol signal Subtraction Percent fatty acid (%)

Linolenic A 0.98: 26.65 22.2 – 26.7

Linoleic B 2.74: 120.13 33.3 2 × 26.7 66.7
Oleic C 2.02: 105.33 16.7 26.7 + 66.7 11.9
Saturated D 2.28:115.64 33.3 26.7 + 66.7 + 11.9 10.3

2
A. Subratti, et al. Sustainable Chemistry and Pharmacy 12 (2019) 100144

Fig. 3. 1H NMR comparing the methyl hydrogens of the linolenic acid with the α hydrogens of the glycerol backbone.

Fig. 4. 1H NMR comparing the methylene hydrogens between two double bonds of the linoleic acid with the α hydrogens of the glycerol backbone.

Fig. 5. 1H NMR comparing the methylene α olefin hydrogens of all unsaturated fatty acids with the α hydrogens of the glycerol backbone.

Fig. 6. 1H NMR comparing the methylene α carbonyl hydrogens of all fatty with the α hydrogens of the glycerol backbone.

3
A. Subratti, et al.
Fig. 7. Appearance of extracted oil from hulled seeds using DME (left); and
commercially available oil via the cold pressing method (right).
Fig. 8. Graph showing percentage recovery of DME after 3 replicates.
2.2. Optimization
The DME was liquefied using dry ice pellets in combination with
acetone as previously described (Subratti et al., 2018). A dispensing
pressure of 8 psi was employed to minimize the loss of uncondensed
DME. The hemp seeds were weighed in a round bottom flask, into
which the DME was directly added. We investigated the mass of hemp
to volume of DME ratio that would allow for optimum extraction
without wastage of the solvent. Our results indicated that a ratio of 1 g:
15 mL was most effective as lower volumes resulted in reduced yields,
whereas higher volumes affected the yields only negligibly.
2.3. General procedure
To a 250 mL round bottom flask equipped with a magnetic stir bar,
10 g of the hemp seeds were added; and 150 mL of DME were dispensed
at a pressure of 8 psi. The contents of the flask were stirred at 400 rpm
while attached to the vacuum trap (Fig. 1). After the desired time of
extraction, the contents of the flask were rapidly filtered into a beaker
using a pre-cooled funnel fitted with a 350 grade Whatman filter paper.
The solvent was allowed to evaporate on the bench top at ambient
temperature and the mass of oil produced was weighed until constant
mass. For the extractions, both (i) unground hulled seeds as well as (ii)
hulled seeds that were ground with a mortar and pestle, were ex-
amined. The extractions were undertaken for various times in order to
compare yields as well as composition of the oil obtained (Fig. 2/
Table 1). Crucially, the DME was able to solvate the oil at low tem-
peratures. The oil extracts were analysed using 1H NMR spectroscopy.
This method relies on the fact that fatty acids undergo esterification to
triacylglycerol derivatives (Barison et al., 2010; Suwannakarn et al.,
4
Sustainable Chemistry and Pharmacy 12 (2019) 100144
2009).
3. Results/discussion
3.1. Percentage yield of oils
The mass of oil extracted increased linearly with time and a plateau
was seen after 40 min which corresponded to excellent yields of 25%
for the unground seeds and 31% for the ground (Fig. 2/Table 1).
We found that the fatty acid profiles of the oil were identical at the
various times shown in Table 1. A comparison of the yields to that from
two typical extracting solvents: petroleum ether (bp: 40–60 °C) and n-
hexane, was undertaken. The established conditions described for the
DME were employed for these solvents at an extraction time of 50 min
at room temperature. Interestingly, the yields obtained with DME were
higher than that for the other solvents used (confirmed using t-test at
the 95% confidence level). This trend was seen for both the ground and
unground seeds, with the former being notably higher that the latter, as
seen in the time-monitored DME extractions.
3.2. Apparatus set-up
We also investigated an alternative method for employing the DME
in a continuous-flow operation for extraction as compared to the stir-
ring method. In order to keep the set-up simple and affordable, we
employed a Liebig condenser as the extracting chamber as seen in
Fig. 1.
The hemp seeds (groundandunground) were stacked in the column
with a glass wool plug at the base, and water at 5 °C was allowed to flow
through the condenser. We found that the yields obtained were com-
parable to that of the stirring method for the unground seeds however it
requires almost twice the volume of solvent for elution. The yields
obtained from the ground seeds were significantly (> 10%) lower than
the stirring method. This was due to the reduced ability of the DME to
penetrate the ground seed packing owing to smaller particle size, under
the action of gravity. This method however does not require the use of a
magnetic stirrer, and eliminates the filtration step; features which may
make this approach amenable to, and attractive on, an industrial scale.
3.3. Oil analysis
The oil extracts were analysed using the method described by
Barison et al. which involves proton NMR spectroscopy (1H) (Barison
et al., 2010). The respective 1H NMR chemical shift assignments as it
relates to different types of protons along the fatty acid chains have
been previously reported (Fauhl et al., 2000; Nikolskaya and Hiltunen,
2018). Table 2 shows the analysis undertaken which utilizes the in-
tegral values from Figs. 3–6, and the methodology established by Bar-
ison (Barison et al., 2010).
Similar to literature values, the linolenic acid content was found to
be approximately 26.7% with the linoleic acid content being 66.7% and
the oleic acid having an abundance of 11.9% (Oomah et al., 2002;
Blade, 1998). The saturated fatty acid content was calculated to be
10.3% which is dominated by the presence of palmitic and stearic acid
(Aachary et al., 2016). This analysis was also performed on commer-
cially available oil extracts obtained by cold pressing, and the values
were similar.
3.4. Chlorophyll content: unshelled and shelled seeds
A common contaminant in hemp seed oil extracts is chlorophyll
which imparts a dark green colour to the oil. From Fig. 7, it can be seen
that chlorophyll content in the DME extract is less. Chlorophyll has
been shown to affect the stability of the oil, causing oxidative de-
gradation and rancidity (Matthäus and Brühl, 2008). This is a result of
using the hulled seeds for extraction as opposed to the cold pressing
A. Subratti, et al.
method that typically extracts from the unshelled seeds. The percentage
yield of oil per gram of unshelled seeds compared to our yield from the
hulled seeds (Kostic et al., 2013), suggests that negligible oil is present
in the shells. The difference in chlorophyll present in the hulled, and
unground seeds was estimated using the protocol described by Aachary
et al. (2016) and equation by Aladic et al. (2015) as shown below:
Concentrations (μg/mL) of chlorophyll a + b = 7.12 x
A663 + 16.80 x A640
The procedure involved dissolving the oil samples in absolute die-
thyl ether followed by thorough mixing using a vortex mixer and ex-
traction using ultrasound. The absorbance of the resulting solution was
measured using a Thermo Scientific Genesys 840–208100 UV/Vis
Spectrophotometer at 640 nm and 663 nm. The concentrations of
chlorophyll in the cold pressed oil was approximately 9 times higher
than that of the DME extract as shown below:
(μg/mL) of chlorophyll a + b in cold pressed unground seed =
(7.12 × 0.323) + (16.80 × 0.076) = 3.576
(μg/mL) of chlorophyll a + b in DME extract of hulled seed =
(7.12 × 0.014) + (16.80 × 0.018) = 0.402
(μg/mL) of chlorophyll a + b in DME extract of unhulled seed =
(7.12 × 0.094) + (16.80 × 0.065) = 1.761
This indicates that extraction using the hulled seeds results in a
lower chlorophyll contamination without compromising the yield of oil.
Also, comparingthe chlorophyll content of the DME extract using un-
hulled seeds (1.761 μg/mL) is still significantly less than that of the
commercially available cold pressed oil (3.576 μg/mL). 3.5 DME re-
covery.
As part of the green approach, we investigated the recyclability of
DME as an extraction solvent in this process. This involved the use of a
Dean-Stark apparatus as previously reported. (37) Fig. 8 illustrates our
results obtained after 3 repetitions. Approximately half of the volume of
DME used can be taken through another cycle of extraction. This is
observed after both the first and second recovery process. It is likely
that most of the DME is lost during the filtration step due to evaporation
as well as some remaining embedded in cellular debris. We expect that
on a industrial scale, the employment of suitable equipment will enable
near 100% recovery of the DME after each extraction cycle.
4. Conclusion
We have successfully demonstrated the ability of DME to extract
hemp seed oil. The yields obtained were notably higher than typical
extraction solvents used. The method is simple and affordable to em-
ploy in any laboratory, with potential application on a commercial
scale. Unlike most solvents, which require heat and reduced pressure to
be removed from extracts, DME evaporates rapidly at room tempera-
ture without any residual solvent left behind. The lack of applied heat
preserves the integrity of the oil. DME is also much safer to use than the
other organic solvents utilized for hemp seed oil extraction and ap-
proximately half of the volume used can be easily recycled.
Declarations of interest
None.
Acknowledgments
The authors thank The University of the West Indies, St. Augustine
Campus for funding this research; as well as Caribbean Gas Chemical
Limited (CGCL) for providing the DME cylinders.
Appendix A. Supplementary data
Supplementary data to this article can be found online at https://
5
Sustainable Chemistry and Pharmacy 12 (2019) 100144
doi.org/10.1016/j.scp.2019.100144.
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