Synthetic polyester from algae oil

Article abstract of DOI:10.1002/anie.201403991

Current efforts to technically use microalgae focus on the generation of fuels with a molecular structure identical to crude oil based products. Here we suggest a different approach for the utilization of algae by translating the unique molecular structures of algae oil fatty acids into higher value chemical intermediates and materials. A crude extract from a microalga, the diatom Phaeodactylum tricornutum, was obtained as a multicomponent mixture containing amongst others unsaturated fatty acid (16:1, 18:1, and 20:5) phosphocholine triglycerides. Exposure of this crude algae oil to CO and methanol with the known catalyst precursor [{1,2-(tBu₂PCH₂) ₂C₆H₄}Pd(OTf)](OTf) resulted in isomerization/methoxycarbonylation of the unsaturated fatty acids into a mixture of linear 1,17- and 1,19-diesters in high purity (>99%). Polycondensation with a mixture of the corresponding diols yielded a novel mixed polyester-17/19.17/19 with an advantageously high melting and crystallization temperature. Algae as feedstock: Crude algae oil from the strain Phaeodactylum tricornutum was transformed into polycondensation-grade purity monomers and thus utilized as feedstock for the production of an algae oil based polyester.

Full text of DOI:10.1002/anie.201403991

Angewandte
Chemie
DOI: 10.1002/anie.201403991
Chemicals from Algae
Hot Paper
Synthetic Polyester from Algae Oil**
Philipp Roesle, Florian Stempfle, Sandra K. Hess, Julia Zimmerer, Carolina Rꢀo Bꢁrtulos,
Bernard Lepetit, Angelika Eckert, Peter G. Kroth,* and Stefan Mecking*
Dedicated to Professor Gerhart von Graevenitz on the occasion of his 70th birthday
Abstract: Current efforts to technically use microalgae focus
on the generation of fuels with a molecular structure identical
to crude oil based products. Here we suggest a different
approach for the utilization of algae by translating the unique
molecular structures of algae oil fatty acids into higher value
chemical intermediates and materials. A crude extract from
a microalga, the diatom Phaeodactylum tricornutum, was
obtained as a multicomponent mixture containing amongst
others unsaturated fatty acid (16:1, 18:1, and 20:5) phospho-
choline triglycerides. Exposure of this crude algae oil to CO
and methanol with the known catalyst precursor [{1,2-
(tBu2PCH2)2C6H4}Pd(OTf)](OTf) resulted in isomerization/
methoxycarbonylation of the unsaturated fatty acids into
a mixture of linear 1,17- and 1,19-diesters in high purity
(> 99%). Polycondensation with a mixture of the correspond-
ing diols yielded a novel mixed polyester-17/19.17/19 with an
advantageously high melting and crystallization temperature.
Considering this background, algae oils are currently
receiving much awareness. Microalgae can be cultivated in
brackish or seawater on non-arable land that is unapt for food
production. Furthermore, no costly nutrients like glucose or
peptones are required necessarily.[2] Rather, sunlight and CO2
may serve as energy source and raw material, respectively.
The relatively high division rates of individual algal strains
may result in a duplication of the biomass within 24 h.[3] At
the same time, the amount of fatty acids in microalgae can be
substantial with around 20–50% of the dry weight.[3,4]
While these advantages of algae oils are often and
increasingly highlighted,[5–7] the application of algae oils so
far is mostly restricted to the extraction of the naturally
occurring ingredients and their utilization as biofuels, pig-
ments, vitamins or for human and animal nutrition. A
prominent example are polyunsaturated w-3 fatty acids
used as food additives. On the other hand, efforts to use
algae oils industrially comprise deoxygenation, pyrolysis, or
even gasification to C1 building blocks and their subsequent
Fischer–Tropsch conversion to higher alkanes. All these
studies aim at using algae oil to generate hydrocarbons that
ideally cannot be differentiated from the corresponding
fractions, like jet fuel, based on crude oil.[8,9] However, the
production of algae is associated with an energy input which
currently still has a significant impact on the overall balance
of fuel generation. This supports the general perception that
generation of more valuable products than fuels for combus-
tion is worthwhile. Interestingly, algae do not only produce
a large amount of lipids, they are also a unique resource for
“unusual” classes of lipids and fatty acids differing from those
available from higher animals and plant organisms.[10] This
opens up unique opportunities for the production of chem-
icals from these oils, which may have a broader variety of
structures and which can also be tailored specifically for
sophisticated applications. Accordingly, we aim at translating
the unique feedstock structure of algae oil into otherwise
inaccessible products with useful properties rather than
mimicking crude oil-based structures. Here, in a pioneering
approach (Scheme 1), we demonstrate the conversion of
algae oil into difunctional molecules, which are novel mono-
mers for the preparation of polyesters.
T
he generation of energy, transportation fuels and chemicals
likewise today still strongly relies on fossil feedstocks.
However, the availability of fossil deposits is limited on the
long term, increasing environmental risks are associated with
the recovery of oil and gas from non-conventional sources,
and the net release of carbon dioxide upon combustion can
disadvantageously affect the global climate. Renewable
resources like biomass from land plants can contribute to
resolve these pressing problems, however, this approach
raises urgent issues such as consumption of land and irrigation
water, a competition with food production, inefficient yields
per time and area, and the associated logistics of harvesting
and collection.[1]
[*] M. Sc. P. Roesle,[+] M. Sc. F. Stempfle,[+] B. Sc. S. K. Hess,
B. Sc. J. Zimmerer, Prof. Dr. S. Mecking
Department of Chemistry, University of Konstanz
78464 Konstanz (Germany)
E-mail: stefan.mecking@uni-konstanz.de
Dr. C. Rꢀo Bꢁrtulos, Dr. B. Lepetit, A. Eckert, Prof. Dr. P. G. Kroth
Department of Biology, University of Konstanz
78464 Konstanz (Germany)
E-mail: peter.kroth@uni-konstanz.de
[+] These authors contributed equally to this work.
We chose the diatom Phaeodactylum tricornutum as
a source for lipids, because published data suggested this
strain to be very effective in the production of the desired
unsaturated fatty acids.[11,12] This species belongs to the group
of diatoms, ubiquitously present in aquatic and unicellular
microalgae, which are major players in the global carbon cycle
with an estimated share of up to 20% of total global carbon
[**] We thank Lars Bolk for SEC and DSC measurements. P.R. gratefully
acknowledges support from the Carl-Zeiss-Foundation by a gradu-
ate fellowship. The authors are grateful for support by the University
of Konstanz and by the Konstanz Research School Chemical
Biology.
Supporting information for this article is available on the WWW
under http://dx.doi.org/10.1002/anie.201403991.
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Figure 2. Light microscopical images of Phaeodactylum tricornutum
before (left) and after (right) treatment with ultrasound and acidic
hydrolysis. Insert in left image shows a single cell, the dark area being
a chloroplast (inset scale bar = 10 mm). The arrows indicate lipid
droplets in the intact cells (left) and released lipids after breaking the
cells (right).
Scheme 1. Approach to a,w-dicarboxylic acid intermediates and poly-
ester materials from algae oil.
fixation.[13,14] Furthermore the genomic information of this
alga is available[15] and genetic manipulation is feasible.[16]
In contrast to traditional plant oils,[17–19] algae do not
contain fatty acids primarily in the form of triacylglycerides,
but rather as diacylglycerides substituted with polar substitu-
ents such as galactosyl or phosphate groups on the third
hydroxy moiety of glycerol (Figure 1).[20] This feature is
about six weeks yielded 5.8 g of algae oil. These results
compare favorably with optimized yields reported from
established methods for lipid extraction.[21,22]
Fatty acids in the extracted algae oil were identified by gas
chromatography (GC) by comparison of retention times and
enrichment with genuine samples of the respective fatty acids
(Figure 3). 48.2% of monounsaturated fatty acids (37.0%
Figure 1. Fatty acids as they appear in plants (gray, top left) and algae
(black).
Figure 3. GC trace of crude algae oil extracted from Phaeodactylum
tricornutum (after transesterification to the methyl esters for analysis).
important, as direct extraction of fatty acids with hydrocarbon
solvents is thus not possible. Note, that also triacylglycerides
can be present, especially when the algae are in the stationary
growth phase for a longer period.
palmitoleic acid (16:1)[23] and 11.2% oleic acid (18:1)), 16.2%
of the multiple unsaturated fatty acid eicosapentaenoic acid
(20:5), and 35.0% of saturated fatty acids (23.4% palmitic
acid (16:0) and 11.6% myristic acid (14:0)) were identified.
However, not only fatty acids are present in the algae oil,
which was already suggested by its green color and evidenced
by gas chromatography (Figure 3) and 1H NMR spectroscopy
(Figure S6, Supporting Information, SI). Possible ingredients,
both ubiquitously present in algae, may be carotenoids or
chlorophylls.
A synthesis of polyesters via polycondensation requires
further conversion to difunctional molecules as monomers.
This requires catalysts compatible with the various compo-
nents of the crude algae oil. For example, the phosphate
moieties may block coordination sites detrimentally, partic-
Phaeodactylum tricornutum starts accumulating visible
lipid droplets in the late stationary phase (Figure 2, left). In
order to extract the fatty acids, different techniques were
tested, namely direct extraction with hydrocarbon solvent,
additional acidic hydrolysis to cleave ester functionalities, and
ultrasonication, homogenization, and microwave treatment to
destroy the cells. To release the lipid droplets from the cells
(Figure 2, left), hydrolysis and mechanical disintegration were
found to be crucial (Figure 2, right), and disintegration by
ultrasound was most favorable. Subsequent lipid extraction
from a 30 L algae culture being in the stationary phase for
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ularly for electrophilic cationic active species. Tetraalkyl
ammonium salts may alkylate phosphine ligands. The activity
of (neutral) ruthenium alkylidene metathesis catalysts was
reported to be decreased tremendously by phosphates, for
example.[24]
Against this background, the extracted algae oil (5.8 g)
was exposed to 20 bar CO pressure at 908C in methanol as
a reagent and solvent in a pressure reactor in the presence of
[(dtbpx)Pd(OTf)](OTf) (970 mmol; dtbpx = 1,2-bis((di-tert-
butylphosphino)methyl)benzene), a known catalyst precursor
for isomerizing methoxycarbonylation.[25–27] GC analysis of
the crude reaction mixture (Figure 4, top trace) clearly
dioleoyl-sn-glycero-3-phosphocholine as a substrate (sub-
strate double bonds/Pd = 125:1). A smooth conversion to
dimethyl nonadecane-1,19-dioate occurred (for details see
SI).
To achieve a substantial molecular weight by means of
classical step-growth polycondensation reactions, a very accu-
rate control of the stoichiometric ratio of functional groups is
necessary.[29] To this end, the appropriate amount of the diol
and the diester components, generated from the algae oil,
were calculated from the peak area percentage obtained from
the GC analyses (SI). Polycondensation catalyzed by titanium
alkoxides afforded a mixed linear long-chain polyester-17/
19.17/19[30] with a number average molecular weight of Mn =
4.0 ꢀ 104 gmolÀ1 as determined by both 1H NMR spectroscop-
ic analysis of the end groups and high temperature size
exclusion chromatography (SEC). The obtained material
showed a melting point of 998C (Tc = 758C, DHm = 136 JgÀ1,
Figure 5).
Figure 4. GC trace of the crude reaction mixture obtained from the
isomerizing methoxycarbonylation of algae oil (top, gray), and after
recrystallization from methanol and heptane (bottom, black).
Figure 5. DSC trace of the algae-derived polyester.
evidences that the monounsaturated fatty acids (16:1 and
18:1) are completely converted to the desired linear 1,17- and
1,19-diester, respectively. These diesters were assigned unam-
biguously by enrichment with genuine samples prepared
independently by methoxycarbonylation of pentadeca-1,14-
diene and methyl oleate, respectively (SI). The signal of
eicosapentaenoic acid also disappeared during the isomeriz-
ing methoxycarbonylation of the algae oil. Apparently,
eicosapentaenoic acid was not transformed to the 1,21-diester
as evidenced by hydrogenation of the reaction mixture and
enrichment with a genuine sample (for preparation of this
1,21-diester see the SI). Possible reaction pathways may be
multiple methoxycarbonylation or hydromethoxylation.[28]
Workup yielded 2.1 g of a mixture of 82% 1,17- and 18%
1,19-diester in polycondensation-grade purity (> 99%,
Figure 4, bottom trace). A part of this mixture was reduced
to the respective diols using LiAlH4. After recrystallization
from chloroform, a mixture of 85% 1,17- and 15% 1,19-diol
was obtained in polycondensation-grade purity (> 99%). The
ratio between the diols with different chain lengths was
slightly different from the ratio of its respective diesters,
presumably due to different solubility of the diols in the
recrystallization. However, this is not a problem for the
following polycondensation reaction (see below).
Other than known long-chain polyesters, the material
prepared here contains a mixture of repeat units with
different numbers of carbon atoms (C17 and C19). Such a less
regular spacing of the ester groups could hinder the formation
of sheets of ester groups and result in reduced order and
melting points.[31–33] However, no such adverse effect was
observed and the melting points are in line with neat model
polyesters-X.X prepared from the genuine samples for gas
chromatographic identification (X = 17: Tm = 998C; X = 21:
Tm = 1048C and X = 25: Tm = 1088C, see SI for details) and
reported data for other polyesters-X.X (X = 18: Tm = 958C[34]
and X = 19: Tm = 1038C[26]). These thermal properties com-
pare to typical thermoplastics, like low density polyethylene
(LDPE).
In summary, a utilization of algae oils for the generation of
higher value chemicals and polymer materials is an attractive
alternative to biofuel production. This requires appropriate
chemical conversions and catalysts compatible with algae oil.
In an exemplary approach (Scheme 1) we have synthesized
polyesters from crude lipids of the diatom Phaeodactylum
tricornutum. Our findings support the feasibility of the
generation of functional chemical intermediates by modern
catalytic methods from algae oil, as exemplified by the
preparation of dimethyl heptadecane-1,17-dioate and hepta-
The remarkable insensitivity of the catalyst towards the
multi-component mixture represented by crude algae oil was
further underlined by methoxycarbonylation of pure 1,2-
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decane-1,17-diol. These molecules are based on a C16 building
block (palmitoleic acid) which is a major component of algae
oils but not of traditional plant oils. a,w-Difunctional com-
pounds can be obtained in high purity, even enabling step-
growth polycondensation to a high molecular weight polyes-
ter. This novel polyester possesses an advantageously high
melting point as a result of the crystallizable linear segments
originating from the algae oil lipids.
Notably, the transition metal catalyzed methoxycarbony-
lation is possible on the crude algae extract. Neither the five-
fold unsaturated eicosapentaenoic acid nor other non-fatty
acid components of the algae (amongst others phosphocho-
lines, see Figure 1) shut down catalysis. While an optimization
of the work-up procedures for larger scale synthesis was not
a focus of this work, it can be noted that already at this stage
a complicated chromatographic workup of the catalysis
products is not necessary. Instead, a recrystallization was
sufficient, which can be readily scaled.
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A detailed investigation on different algae strains—
including genetic modification—for the production of fatty
acids, alternative extraction methods, and the conversion by
other synthetic methods are part of our ongoing research in
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Experimental Section
Detailed procedures and characterization of monomers and polymers
(including NMR spectra, GC-, SEC- and DSC-traces, and WAXS) are
given in the Supporting Information.
Growth of algae: Phaeodactylum tricornutum UTEX 646 was
obtained from the Culture Collection of Algae at the University of
Texas in Austin and grown in 10 L flasks in a modified f/2-
medium[35,36] (pH 7) with artificial half concentrated sea salts
(16.6 gLÀ1, tropic marine) and 0.09 mm MnCl2 at a light intensity of
35 mmolsÀ1 mÀ2 in a day/night rhythm of 16/8 h at 208C. Ambient air
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isomerizing methoxycarbonylation.
Isomerizing methoxycarbonylation: Crude algae oil (5.8 g) and
the catalyst precursor [(dtbpx)Pd(OTf)](OTf) (0.97 mmol), or 1,2-
dioleoyl-sn-glycero-3-phosphocholine (450 mg, 0.57 mmol) and the
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methanol. In a pressure reactor, the solution was pressurized with
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product mixture was analyzed by GC. Recrystallization yielded 2.1 g
and 320 mg of the desired linear diesters, respectively.
Polymerization of algae oil monomers: Stoichiometric amounts
of the algae oil-based linear diester and diol mixtures were mixed in
a mechanically stirred Schlenk tube. Titanium(IV) tetrabutoxide was
added as catalyst and the mixture was heated stepwise to 2008C under
reduced pressure to yield the algae oil-based polyester.
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Received: April 4, 2014
Published online: && &&, &&&&
Keywords: algae oil · catalysis · polyester · renewable resources
.
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Communications
Chemicals from Algae
P. Roesle, F. Stempfle, S. K. Hess,
J. Zimmerer, C. Rꢁo Bꢂrtulos, B. Lepetit,
A. Eckert, P. G. Kroth,*
S. Mecking*
&&&& — &&&&
Synthetic Polyester from Algae Oil
Algae as feedstock: Crude algae oil from
the strain Phaeodactylum tricornutum was
transformed into polycondensation-grade
purity monomers and thus utilized as
feedstock for the production of an algae
oil based polyester.
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Angew. Chem. Int. Ed. 2014, 53, 1 – 6
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