Chemical Engineering July 2014 - 11

Edited by Gerald Ondrey
July 2014
Platform for reactive monomers enables short cure times for coatings
T
Chemilian
H
R1
H
R2
R1
H
Forza
H
H
Cross-linker
L
O
Diethyl malonate
feed
* Existing
petrochemical
feedstock
* Emerging
biobased
feedstock
Reactor
vessel 1
Proprietary
intermediate
Formaldehyde
Chemilian
with the diethyl ester of malonic acid,
which reacts with formaldehyde under
controlled conditions to yield a proprietary
intermediate species. The intermediate
then reacts with a specially designed
heterogeneous catalyst system to make
the monomer. A critical component of the
process is the set of compounds added
to the reaction mixture to stabilize the
monomer product, including species that
prevent premature polymerization of the
monomer by both the anionic- and freeradical-polymerization
routes.
In addition to altering the chemical
groups on the alkene, Sirrus also tailors
the stabilization package to the demands
EC Corp. (Tokyo, Japan; www.nec.
com) has developed a two-stage,
heterogeneous synthesis for making a
high-functionality bioplastic (70 wt.%
plant content) from non-edible plant
cellulose. The new bioplastic is said to
have excellent thermo-plasticity (275
MFR), heat resistance (140°C glass
transition temperature) and water
resistance, properties that make it
suitable for durable products, such
of a particular application, Uhrig says.
The company now produces two related
alkene monomers - one with a crosslinker
(known as Forza) and one without
(known as Chemilian) - that can be combined
to achieve the desired properties of
hardness, optical clarity, temperature resistance
and others.
Uhrig says the company currently manufactures
35-40 kg/wk of monomer for
testing by potential users. Sirrus is in talks
with multiple original equipment manufacturers
(OEMs) in the automotive industry,
as well as with chemical suppliers, to form
manufacturing partnerships surrounding
the production of monomer for various
coating applications. In the future, Sirrus
may establish its own manufacturing facility
and explore the use of the monomers in
a much wider range of applications.
Oil-water separation
a complex formed by combining
maleic anhydride
copolymers with a cationic
fluorosurfactant can separate
oil from water when coated on
a wire mesh. researchers at
Durham university (u.K.; durham.ac.uk)
devised a method
of preparing the complex in a
single step. This may render
it more readily produced at
industrial scales compared to
previous efforts, the researchers
say. in the complex,
fluorinated alkyl chains orient
toward the air-solid interface
to form a low-surface-energy
film. This orientation localizes
(Continues on p. 16)
A new route to a cellulose-based bioplastic
N
Reactor
vessel 2
Distillation
tower
O
O
O
Recycle
O
O
Purge
H
R2
he potential usefulness of 1,1-di-substituted
alkenes for making performance
polymers has been recognized for some
time, but commercialization has been
elusive because of the reactive nature of
the monomers. Startup company Sirrus
Inc. (Loveland, Ohio; www.sirruschemistry.com)
has developed technology to stabilize
monomers in this chemical class,
as well as the intermediates that precede
them, enabling their use in coatings and
other applications.
Coating products resulting from the
anionic polymerization of 1,1-di-substituted
alkenes have several significant
advantages, explains Sirrus CEO Jeff
Uhrig, including rapid curing times at
ambient temperatures, which can dramatically
reduce energy consumption.
And by tailoring the chemical structure
of the monomers (diagram, top), we are
able to generate products with a range
of performance properties using a single
chemistry platform, Uhrig says.
The Sirrus process (flowsheet) starts
as electronic devices. The company
plans to mass-produce the bioplastic
during 2016.
To make the biopolymer, swollen
gel-like cellulose materials are first
reacted with modified cardanol (longchain
components derived from the
agricultural byproduct, cashew-nut
shells) and acetic acid (short-chain
component) at temperature of 100°C
or less to make a resin. The resin can
Note: For more information, circle the 3-digit number
on p. 68, or use the website designation.
be easily recovered by solid-liquid
separation methods, such as precipitation
and filtration. Unlike conventional
homogeneous processes, NEC's
process does not require a solvent for
recovering the product resin. As a result,
the overall process uses 90% less
solvent than conventional methods,
says the company. Energy requirements
are said to be one tenth those
needed by alternative routes.
ChemiCal engineering www.Che.Com July 2014 11
http://www.sirruschemis http://www.try.com http://ham.ac.uk http://www.nec http://www.Che.Com
Chemical Engineering July 2014

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