Watching solid catalysts work - P.28 New analytical methods reveal hidden chemistry in the industrially critical materials - FTP Directory Listing

How The science
 chemistry behind ice
 is changing cream and
 the mattress other frozen
 business treats
 P.20 P.27
JULY 17, 2017

 Watching
solid catalysts
 work
 New analytical methods
 reveal hidden chemistry in the
 industrially critical materials
 P.28

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American Chemical Society

Contents VOLUME 95, NUMBER 29

 July 17, 2017

 Cover story

 Hunting for
 the hidden
 chemistry in
 solid catalysts
 Advances in analytical techniques
 uncover subtleties of these
 essential industrial catalysts
 Page 28

Quote of the week Features
“We in the 22 C&EN talks with
 Tracey Weissgerber,
chemical industry data visualization
did what we do crusader
 Mayo Clinic researcher explains
best. We figured why bar graphs are often the
out how to do it wrong choice for displaying data

efficiently and at 26 An introvert’s guide
a large scale.” to networking
 Looking for ways to help others
 —Will Koonce, Dow can ease the awkwardness of
 ChemicalPage 20 asking for help when job hunting

 27 Periodic graphics:
 20 To sleep, perchance The chemistry of
 on foam 24 For Hengrui, R&D frozen desserts
 Advances in polyurethane plans pan out A collaboration between C&EN
 chemistry are helping Ambitious program to launch and Andy Brunning, author
 revolutionize the mattress innovative drugs starts to pay off of the popular graphics blog
 industry for Chinese generics producer Compound Interest

Lines depict possible paths
 Departments ACS News
for molecules through a solid
catalyst.Scanning electron 2 Editorial 38 C&ENjobs 34 ACS Comment
microscopy composite image by 3 Reactions 40 Newscripts 35 Awards
Bert Weckhuysen/Utrecht U. 5 Concentrates 36 Obituaries
 CE NEA R 9 5 (29 ) 1–40 • ISSN 0009 -2347

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 I
 NEW YORK CITY: (212) 608-6306
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 CHICAGO: (917) 710-0924 Lisa M. Jarvis (Senior Correspondent).
 the upcoming ACS national meeting ed that a group of NASA scientists is now
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 SCIENCE/TECHNOLOGY/EDUCATION And second, the much anticipated total Now, this soil may be fake, but it is
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Celia Henry Arnaud (Senior Editor), Stuart A. Borman (Senior Correspondent), eclipse of the sun will happen on day two far more Earth abundant and cheaper
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 JOURNAL NEWS & COMMUNITY in this part of the world in decades. For it is going to go for millions of dollars.
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 ACS NEWS & SPECIAL FEATURES
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 Linda Wang (Senior Editor) Carolina, the eclipse will change daytime during his trip (which coincidentally took
 EDITORIAL PROJECTS EDITOR: Jessica Morrison
 skies into twilight for just a few minutes. place 48 years ago on July 20, the day
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 EDITING & PRODUCTION
 Kimberly R. Bryson, Assistant Managing Editor this looks like as if the moon took out a $2 million to $4 million.
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 with an estimated 81% obscuration of ward to the symposium and solar eclipse
 Robert Bryson, Creative Director the sun. during the national meeting here in D.C.
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­ ssociate), Yang H. Ku (Art Director), William A. Ludwig (Associate Designer)
A ACS is convening a symposium orga- the eclipse at the national meeting, you’ll
 DIGITAL PRODUCTION nized with NASA on Aug. 22–23. Under need more than just sunglasses to see it.
 Renee L. Zerby, Manager, Digital Production
 Luis A. Carrillo (Web Production Manager), Cesar Sosa
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 people.” North American skies.
 ADVISORY BOARD
Deborah Blum, Raychelle Burks, Jinwoo Cheon, Kendrew H. Colton, François-
 Speaking about Mars and space explo-
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Matthew Hartings, Christopher Hill, Peter Nagler, Anubhav Saxena, Dan Shine,
Michael Sofia, William Tolman, James C. Tung, Jill Venton, Helma Wennemers,
 ently there is such a thing as fake space
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 Published by the AMERICAN CHEMICAL SOCIETY “fake” craze would affect space science
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 too? And it turns out that we are not
 so good at making it. What I’m talking
 EDITORIAL BOARD: Nicole S. Sampson (Chair),
 ACS Board of Directors Chair Pat N. Confalone, about here is artificial soil—also called
 ACS President Allison A. Campbell, Cynthia J. Burrows, simulant—that replicates the surface of
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 planets, satellites, and asteroids. Scien-
 Copyright 2017, American Chemical Society
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 tists use it to test rovers or drills and in-
 Volume 95, Number 29 vestigate how rocks weather in space, for
 example. But existing simulants mimic Editor-in-chief
 only space dirt’s physical properties, not @BibianaCampos

 Views expressed on this page are those of the author and not necessarily those of ACS.

2 C&EN | CEN.ACS.ORG | JULY 17, 2017

Reactions
 board) approach to analytical tools.
 This reminds me of an unusual book,
 “The Golden Book of Chemistry Experi-
 ments” by R. Brent with charming illus-
 trations by H. Lazarus, which describes a
 chemical laboratory for teenagers using coat
 hangers for ring stands and test tube racks;
 old ink bottles for alcohol lamps; pickle jars
 for beakers; flashlight batteries for
 ▸ From the web age of a famous electrolysis; and homemade litmus,
 recurring theme starch-iodide, and turmeric test pa-
 from the artist pers. A balance was shown as being
 Re: Birds’ compasses M. C. Escher constructed from a tin can and string,
 A reader discusses bird navigation. (part of his series with coins used as weights. Chemicals
 cenm.ag/birdcompass on tessellation). were obtained from the laundry room
 A much apropos or neighborhood drugstore.
 In reference to the main competing bio- choice from the If “mom” were supportive, the
 physical hypothesis of magnetoreception MIT team for an Escherichia coli “painting.” kitchen table could be put into service as
 (biological precipitation of ferromagnetic David Bolliet a lab bench, although some experiments
 minerals like magnetite) Peter Hore states, Kalamazoo, Mich. were suggested as being conducted out-
 “Very little evidence has emerged over the doors. A hydrogen bomb was erroneously
 past 15 years that supports that as the ba- Combination drug therapy indicated as being possible by scaling up
 sis for a compass in birds.” the experiment for hydrogen generation. As
 Well, as one of the originators of the This is in response to “When two drugs one reviewer wrote: “Nothing bonds parent
 ferromagnetic hypothesis, I beg to differ. are better than one” (May 29, page 7). The and child as much as almost blowing up the
 It is not just birds, it is a large variety of concept [that] two or more plant constitu- garage together”!
 microorganisms and animals, including ents when administered together enhance The first edition came out in 1960 and a
 birds, that have this magnetic sense. The the desired therapeutic effect (scientific revised edition was published in 1963. The
 definitive test of a ferromagnetic receptor term, synergy) has been known for cen- book was banned almost immediately by the
 based on single-domain (SD, uniformly turies in the Indian Ayurvedic and tradi- U.S. government as being too hazardous for
 magnetized particles) is the pulse-remag- tional Chinese systems of medicine. While kids. No eye or hand protection is indicated
 netization experiment, in which you apply modern medical practice has been slow in for any experiment. Evidently only a few
 a brief, unidirectional magnetic pulse of recognizing merits of such combination hundred copies still exist and fall into the
 about a mS in duration, configured to ex- drug therapy, thanks to better understand- category of very pricey rare books. Boys and
 ceed the coercive force of the SD particles ing of its underlying principles through girls are both shown as budding chemists on
 and reverse the orientation of the magnetic computer-generated theoretical models nearly every page in a nod to gender equality.
 moment wrt to the crystal axis (typically, and newer analytical technologies, synergy Thanks to a benefactor, the complete
 a pulse few tens of mT is adequate). That research with anticancer plant products book with its over 200 experiments, many
 produces a permanent flip in magnetiza- and conventional drugs is now an active classics in the history of chemistry, is avail-
 tion direction, the same way information area for developing new cancer therapy. able as a free, downloadable PDF on Google.
 is coded on magnetic tape. Magnetotactic The benefits of synergism include in- Thomas F. Spande
 bacteria, exposed to such a pulse, reverse creasing the efficacy of therapeutic effect, Bethesda, Md.
 their magnetic swimming directions decreasing dosage without compromising
 passively. There are now over 16 peer-re- efficacy, mitigating or obliterating toxic Join the conversation.
 viewed papers in which this experiment side effects, and minimizing or delaying the
 facebook.com/CENews
 has been applied to animals, including induction of drug resistance. Recent exam-
 birds, all which show clear and lasting ef- ples: curcumin (a yellow diketo polyphenol) @cenmag
 fects of the pulse. Such a pulse would have from turmeric powder and betanin (a red
 no lasting effect on a quantum compass. anthocyanin glycoside) from red beetroot
 There may be interesting magnetic
 effects on chemical reactions, but the ev-
 acting synergistically when coadministered
 with standard cancer drugs, such as doxo-
 How to reach us
 idence that they are involved in magneto- rubicin and cisplatin. Further, they provide Chemical & Engineering News
 reception is frankly not convincing. adjuvant therapeutic remedy for the toxic Letters to the Editor
 side effects of these potent anticancer drugs ▸ Oure-mail address is edit.cen@acs.org.
 Joseph L. Kirschvink ▸ Our fax number is (202) 872-8727.
 (see our article, J. Complementary Integr.
 ▸ Letters to the editor Med. 2013, DOI: 10.1515/jcim-2013-0007).
 ▸ Comments can be left at cen.acs.org.
 ▸ Or you can send your letter to:
 G. Subba Rao C&EN Editor-in-Chief
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 Washington, DC 20036
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 should include the writer’s full name, address, and home
 visual reminder that science is an art. One telephone; letters and online comments may be edited
 striking element is, however, missing from I thoroughly enjoyed your interview with for purposes of clarity and space. Because of the heavy
 M. Torrice’s write-up: To illustrate their Manu Prakash (April 17, page 28) and a volume of mail received at C&EN, writers are limited to one
 findings, the researchers opted for an im- glimpse at his “make it yourself ” (of card- letter in a six-month period.

 JULY 17, 2017 | CEN.ACS.ORG | C&EN 3

Time flies
 and so do advances in energy research
with ACS Energy Letters

 Celebrating the 1st anniversary of the journal’s inaugural
issue with ENERGY EXPRESS — a new manuscript type that
 lets authors publish preliminary findings with great speed

 READ THE JOURNAL AND
 SUBMIT YOUR RESEARCH AT
 pubs.acs.org/acsenergylett

Concentrates
 ▸ Highlights
 Plants inspire strong, elastic graphene aerogels 7
 Dopamine transmits signals between immune cells 7
 New details on mercury’s route to the Arctic 9
 Malaria drug prevents Zika-related birth defects in mice 11
 Europe slams Merck KGaA for hiding info 14

 Chemistry news from the week FDA lowers bar for rare-disease drug approval
 Broad Institute jump-starts CRISPR patent pool
 Arkansas, Missouri ban dicamba herbicide
 14
 15
 19

 CANCER

 Treatment-resistant cancers
 have Achilles’ heel Cl
 N
 O NO2 ML210 is one of
 several compounds
 that inhibit GPX4, an
 Common vulnerability is druggable N N O enzyme that protects
 treatment-resistant
 pathway leading to iron-induced cell death cancer cells from cell
 death.
 Through mutations or changes in gene duced cell death in which iron
 expression patterns, some cancer cells catalyzes the formation of free Cl cell culture and mice experi-
 become resistant to common treatments radicals that kill the cells. ments, several GPX4 inhibitors
 such as radiation, chemotherapy, targeted In particular, the researchers found from the team’s compound library killed
 drug therapy, and immunotherapy. molecules that kill mesenchymal cancer treatment-resistant cancers, including
 A new study reports that these resistant cells by inhibiting a selenoenzyme called non-small cell lung cancer, pancreatic can-
 cancers do have a vulnerability: They glutathione peroxidase 4 (GPX4). Mesen- cer, prostate cancer, and melanoma.
 depend on an enzyme to protect them chymal cancer cells oxidize polyunsatu- Schreiber describes the work as “a
 from iron-produced free radicals (Nature rated lipids to form lipid peroxides. Iron chemical biology-based approach to un-
 2017, DOI: 10.1038/nature23007). The in the cells can react with the excess lipid derstanding resistance.” The study’s key
 work opens a potential new route to fight peroxides to produce lipid radicals that insights, he says, “were gained by seeing a
 cancer in people who currently lack good cause ferroptosis. To protect the cells bizarre pattern of sensitivity of 900 cancer
 treatment options because conventional from ferroptosis, GPX4 reduces the lipid cell lines to 500 selective small-molecule
 ones don’t work, say the researchers, led peroxides to lipid alcohols. probes.” To help cancer researchers find
 by Stuart L. Schreiber of Broad Institute GPX4 inhibitors block this protective other vulnerabilities in cancer cells and
 and Harvard University. pathway and use the cells’ susceptibility to accelerate therapeutic discoveries, the
 Often cancer cells become resistant to ferroptosis to let them kill themselves. In team has made its screening data and
 therapies because of genetic analysis tools freely available
 mutations. But the new study Schreiber (left) and Vasanthi S. Viswanathan, first author of the at an online resource called
 focused instead on mesen- new paper, in their Broad Institute lab. the Cancer Therapeutics Re-
 chymal cancer cells, which sponse Portal.
 gain resistance through Arjun Raj of the University
 changes in gene expression. of Pennsylvania, who has
 The researchers believe this studied treatment-resistant
 type of gene-expression cancers, calls the work very
 “plasticity” to be an initial important. “One of the most
 response of cancer cells to exciting findings is that
 treatment, after which the treatment-resistant cancer
 cells can go on to make muta- cells have some convergent
 tional changes as well. general principles that can
 The team screened a li- be exploited therapeutically,
 brary of small molecules to instead of the case-by-case,
 look for compounds that whack-a-mole approach that
C R E D I T: JO H N K. EATO N

 could break the cells’ armor. is currently dominant” for
 The screening experiments treating resistant cancers,
 revealed that the cells have he says. “Identifying the
 an unusually high susceptibil- GPX4 pathway raises many
 ity to ferroptosis, a recently exciting therapeutic possibili-
 discovered form of self-in- ties.”—STU BORMAN

 JULY 17, 2017 | CEN.ACS.ORG | C&EN 5

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Science Concentrates
 ELECTRONIC MATERIALS

 Strong graphene
 aerogels
 bounce back
 Plant-inspired materials are A graphene aerogel recovers after being squished by an object
 strong, elastic, and conductive more than 6,000 times its weight.

 Ultralight and exceptionally strong, strength, superelasticity, and conductivity graphene aerogel, 10 mm on a side, using
 graphene aerogels are attractive materials in an aerogel requires carefully designed, a specialized freezing technique for creat-
 for use as catalysts, electrodes, and flex- ordered structures, says Hao Bai of Zheji- ing structured porous materials that Bai
 ible electronics. But one property that’s ang University. He and his colleagues took helped develop in 2015 while at Lawrence
 needed for those applications has been inspiration from Thalia dealbata, an aquat- Berkeley National Laboratory. The method
 hard to impart to the materials: elastici- ic plant with strong and flexible stems that uses ice as a template to freeze a suspen-
 ty. Researchers have now overcome that allow the plant to withstand wild winds. sion of graphene oxide such that parallel
 hurdle by making a squishable graphene The stems are built out of concentric lay- graphene oxide sheets form, connected
 aerogel that mimics a bendable aquat- ers of 100- to 200-µm-diameter structural by bridges as in T. dealbata. Freeze-drying
 ic plant’s highly ordered inner porous tubes, connected to each other by thinner, and warming the sample transformed the
 structure (ACS Nano 2017, DOI: 10.1021/ 1-mm-long bridges that act like springs. material into graphene, producing the
 acsnano.7b01815). The researchers sought to replicate the aerogel.
 The new, conductive aerogel springs plant’s properties with a similar struc- In addition to being strong and elastic,
 back to its original shape after being ture in an aerogel. They made a cube of the material is highly conductive, consid-
 squeezed to half its size with an ering its low density, Bai notes.
 object more than 6,000 times its This is a clever, low-cost,
 weight. The aerogel retains 85% and scalable freezing process to
 of its original strength even after generate a new aerogel micro-
 being squeezed more than 1,000 structure, says Peter Pauzauskie
 times. In comparison, typical of the University of Washington.
 aerogels with random pore struc- The microstructure “would be
 tures that the researchers made very expensive and difficult to
 and tested lost more than half achieve” using other methods, in-
 their strength after just 10 com- cluding three-dimensional print-
 pression cycles. The ordered structure of a graphene aerogel (left) mimics ing, he says.—PRACHI PATEL,
 Combining low density, that of a strong, flexible aquatic plant stem (right). special to C&EN

 CHEMICAL COMMUNICATION

 Dopamine sends immune signals too
 Nerve cells often communicate chemical- or the spleen. Once there, activated T cells ing dopamine and related neurotransmit-
 ly. One cell releases packets of molecules and B cells “talk” to each other through ters in nerve cells.
 called neurotransmitters, which then influ- immunological synapses—similar to the In cell culture experiments, the team
 ence the behavior of another neuron. Dopa- structures used in nerve cell communica- found that human B cells exposed to dopa-
 mine is one such neurotransmitter known tion. The conversation between the cells mine move proteins important in immune
 to carry signals in brain circuits involved in further activates them, including trigger- responses to their surfaces. This triggers
 rewarding behavior and motor control. ing the B cells to mature and start produc- a feedback loop that helps strengthen the
 Now scientists report that dopamine ing antibodies to clear the infection. synapses between T cells and B cells and
C R E D I T: ACS NA N O ( B OT H )

 also ferries messages between immune Ilenia Papa and Carola G. Vinuesa of pushes the B cells to mature.
 cells outside the brain to promote an- the Australian National University and The findings, Papa says, could lead
 tibody production (Nature 2017, DOI: coworkers studied immune cells from hu- to strategies to enhance dopamine sig-
 10.1038/nature23013). man tonsils, spleens, and lymph nodes and naling to boost vaccination responses
 When a pathogen invades the body, determined that the T cells in the samples or to disrupt it to block the produc-
 immune cells that recognize the threat contained granules filled with dopamine. tion of autoantibodies in autoimmune
 become active and migrate to lymph nodes These granules are similar to those carry- diseases.—MICHAEL TORRICE

 JULY 17, 2017 | CEN.ACS.ORG | C&EN 7

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Science Concentrates
 POLLUTION

 New details on mercury’s
 route to the Arctic
 Most deposition of the toxic metal in the tundra
 is from gaseous elemental mercury, study finds Researchers monitored mercury levels
 at Toolik Field Station, northern Alaska,
 Mining operations, coal-fired plants, and to long-range transport, whereas Hg2+ in part with this meteorological tower
 other sources of mercury pollution world- is more reactive and shorter lived. The (foreground) and instrument hut.
 wide have led to the deposition of the neu- findings have implications for policies to
 rotoxic metal in the Arctic. The chemical reduce Hg pollution, which contaminates ditional amounts directly from the atmo-
 mechanism behind this deposition is not plants, fish, and mammals that native peo- sphere. The researchers also determined
 completely understood. ple rely on for food, in Arctic ecosystems. that Hg levels in Arctic soil are up to five
 Environmental scientists’ prevailing In the study, a team led by Daniel times as high as levels in temperate re-
 hypothesis is that Hg from anthropogenic Obrist of the University of Massachusetts, gions. This is likely because warmer tem-
 and natural sources travels through the Lowell, and the Desert Research Institute peratures tend to release Hg from plants
 atmosphere and collects in the Arctic pri- measured Hg levels in air, snow, plants, and soil and return it to the atmosphere.
 marily as Hg2+ that falls in rain and snow. and soil at Toolik Field Station in northern “To take concrete steps to reduce Hg
 A study now finds that the primary Alaska and other sites for two years. They accumulation, one must understand how
 source of the pollution is absorption of found that Hg0 accounted for about 70% the metal moves around in the environ-
 gaseous elemental mercury (Hg0) from the of total Hg deposition in the ecosystem, ment,” comments Hg biogeochemistry
 atmosphere, not Hg2+ from precipitation with Hg2+ only a minor contributor. expert Carl Lamborg of the University
 (Nature 2017, DOI: 10.1038/nature22997). The study shows that Hg0 accumulates of California, Santa Cruz. “This paper
 Hg0 is more stable and lasts longer in in the tundra all year but to a greater ex- addresses that, adding to our predictive
 the atmosphere, making it more subject tent in summer, when plants take up ad- capabilities.”—STU BORMAN

 SYNTHESIS

 Automating reaction discovery
 that vary in mass. So when the compounds
 Approach combines chemical design and react, they form products with unique
 informatics to find new chemical transformations differences in mass that are detected by
 GC/MS and identified by analysis with the
 When hunting for novel chemical reac- ent metal and ligand combination to each. macros.
 tions, the more transformations chemists They then used GC/MS to analyze their “By following these macros, the out-
 can do, the more likely they are to find results (C&EN, Sept. 12, 2011, page 10). comes of thousands of possible reactions
 something new. University of California, “The deconvolution of the GC/MS data of two or multiple reactants can be ana-
 Berkeley, chemists John F. Hartwig and to identify more than the major products lyzed in an automated fashion, and new
 Konstantin Troshin have come up with an was a stumbling block for the routine use reactions can be discovered,” Hartwig says.
 approach that lets reaction hunters run of this approach,” Hartwig says. So he and “This is a real breakthrough, since it
 75,000 possible reactions in just a matter Troshin went back to the drawing board. speeds up the time for analysis and allows
 of days using only a sealed 96-well plate, Their new method uses three pools its automation,” comments Frank Glorius,
 a gas chromatography/mass spectrometry of compounds. Each pool has molecules an expert on smart screening at the Univer-
 instrument, and an analytical suite of Mi- with the same types of functional groups: sity of Münster. He notes that Hartwig and
 crosoft Excel macros (Science 2017, DOI: an alkyne, a halide, and a boronic acid, Troshin even managed to use the method
 10.1126/science.aan1568). for example. The pools differ in that the to discover a previously unknown nick-
 The reaction discovery method F compounds also have inert substituents F el-catalyzed, three-component reaction
 updates an earlier approach taken (shown). “This paper will attract a lot
 OH
 by Hartwig’s lab, in of interest from chemists
C R E D I T: DA N I E L O BR I ST

 which the chemists Br B OCH3 from different disciplines,
 5% Ni(COD)
 OH 10% PPh 2
 loaded a combina- 3 leading to more activity
 + + H CO
 tion of 17 reactants F 3 in this challenging field
 into each well of a 3 equiv. 3 equiv. F of ‘smart screening,’ ”
 96-well plate and Glorius says.—BETHANY
 then added a differ- COD = cyclooctadiene, Ph = phenyl HALFORD
 F F
 JULY 17, 2017 | CEN.ACS.ORG | C&EN 9

Science Concentrates
CHEMICAL BONDING
▸▸ Dioxygen’s stability
lies in resonance
Oxygen as O2 is stable enough to be abun- Wrapping sulfur spheres in thin MoS2 flakes protects the material and
dant in the environment and is required for enables repeated lithiation reactions in batteries.
many forms of life. But from the standpoint
of theory, dioxygen’s stability is curious: ENERGY STORAGE
Its highest occupied molecular orbitals
contain two unpaired electrons, making it
a diradical. Instead of wafting around as
 MoS2 wrap protects
O2, the molecule should be busy abstract-
ing hydrogen atoms or forming oligomers;
isoelectronic sulfur, for example, is most
 lithium-sulfur batteries
stable as S8. The key to dioxygen’s reactivity A simple procedure for wrapping sulfur particles in thin sheets of molybdenum
lies in resonance. That finding comes from disulfide may offer a way to capitalize on the promise of high-performance
experimental and computational analysis lithium-sulfur batteries, according to a study (J. Am. Chem. Soc. 2017, DOI:
by Weston T. Borden of the University of 10.1021/jacs.7b05371). Lithium batteries made with sulfur, a low-cost and abun-
 dant element, have the potential to store five times as much energy by weight
 as conventional Li-ion batteries. But long-lasting Li-S batteries have remained
 elusive because of several materials and chemistry problems. For example,
 electrochemical reactions in these batteries form troublesome lithium poly-
 sulfides, which dissolve in the electrolyte solution, reducing the availability of
 energy-rich lithium. In addition, lithiation reactions lead to substantial swell-
 ing of the cathode, which can trigger cracking and failure of that electrode. In
 an attempt to bypass those problems, Wei Tang and Kian Ping Loh of National
 University of Singapore and coworkers reacted a polyvinylpyrrolidone suspen-
 sion of hollow sulfur particles with ultrathin MoS2 flakes, causing the flakes
 to tightly encapsulate the sulfur particles. The team made batteries fitted
 with cathodes prepared from the MoS2-S hybrid material and found that they
Resonance of O2’s π system stabilizes retained much of their high initial charge capacity even after 1,000 charging cy-
the molecule. cles. The researchers attribute the good performance to strong van der Waals
 forces between the MoS2 layers, which help prevent escape of lithium polysul-
North Texas, Roald Hoffmann of Cornell fides. They also found that wrinkles in the MoS2 wrap provide ample space to
University, and their colleagues (J. Am. accommodate swelling of the sulfur particles upon lithiation.—MITCH JACOBY
Chem. Soc. 2017, DOI: 10.1021/jacs.7b04232).
Confirming a 1931 proposal by Linus
Pauling, the researchers determined that
O2’s π bond can be thought of as a pair of bind to a partic-
two-center, three-electron bonds, with H H ular drug target.
resonance contributing a net stabilization N N Ru catalyst, Mg2+ N N However, these
energy of 418 kJ/mol. S2 is stabilized by only O O libraries gen-
about 213 kJ/mol. The consequence is that erally have not
trimerization of O2 is endothermic, while By adding magnesium ions, researchers been able to in-
S2 is exothermic. Meanwhile, O2’s σ bond can perform ring-closing metathesis clude ring compounds in the drug screen-

 C R E D I T: J . A M . C H EM . S O C. ( S U LFU R S P H ER ES , D I OXYG E N )
is relatively weak, so oxidation reactions reactions using a ruthenium catalyst on ing because transition-metal catalysts, es-
are ultimately exothermic when they do DNA-tagged molecules. sential for ring-closing reactions, can bind
occur.—JYLLIAN KEMSLEY to charged DNA backbones and cause the
 the diversity of DNA-encoded libraries strands to fall apart. Now, a team led by
 used by drug developers to rapidly screen Xiaojie Lu and Lijun Fan of GlaxoSmith-
MEDICINAL CHEMISTRY and identify promising drug candidates Kline has found that by protecting the
▸▸ Making ring (Bioconjugate Chem. 2017, DOI: 10.1021/
 acs.bioconjchem.7b00292). Building such
 DNA tags with magnesium ions, they can
 produce a variety of DNA-encoded het-
 libraries involves facilitating reactions be- erocycles and macrocycles using rutheni-
compounds for DNA- tween small molecules tagged with short, um-catalyzed ring-closing metathesis. The
encoded libraries unique DNA sequences to create myriad
 products, which are then tagged with ad-
 team hypothesizes that because the mag-
 nesium ions occupy all the DNA’s binding
 ditional unique DNA sequences. The DNA sites, the ruthenium catalyst is forced to
A simple tweak to a tool for making mac- serves as a sort of bar code to identify the react with the substrates instead of the
rocyclic compounds could help increase compounds in a library that successfully DNA.—XIAOZHI LIM, special to C&EN

10 C&EN | CEN.ACS.ORG | JULY 17, 2017

NANOMEDICINES
 INFECTIOUS DISEASE
 ▸▸ Antioxidant
 nanoparticles could Malaria drug prevents Zika-
 treat sepsis related birth defects in mice
 Sepsis occurs when the body’s immune Zika infection during pregnancy can cause devastating
 response to an infection spirals out of con- birth defects. Children born to mothers with Zika OH
 trol. The inflammatory signals designed can have abnormally small heads and brains HN N
 to kill bacteria and other invaders spread (a condition known as microcephaly),
 beyond the infection site and in the worst abnormal reflexes, epilepsy, as well as
 cases lead to organ failure and death. The problems with vision, hearing, and diges-
 only effective treatment for sepsis is anti- tion. Indira U. Mysorekar and coworkers Cl N
 biotics, but they target only the source of at Washington University School of Med- Hydroxychloroquine
 the infection, not its symptoms. To com- icine in St. Louis have discovered that in
 bat that inflammation, scientists at Seoul the placenta, Zika may be hijacking autophagy—cells’ process for removing
 National University, led by Seung-Hoon toxins and recycling damaged components to generate energy—thereby in-
 Lee and Taeghwan Hyeon, synthesized ce- fecting developing fetuses (J. Exp. Med. 2017, DOI: 10.1084/jem.20170957). The
 ria-zirconia nanoparticles to scavenge reac- researchers infected pregnant mice that were missing an essential autophagy
 tive oxygen species (ROS) that damage and gene and found they had significantly lower levels of detectable virus and less
 kill cells. The cerium ion Ce3+ mimics nat- placental and fetal damage compared with pregnant mice with the gene. They
 ural catalysts that remove superoxide and then looked to see how hydroxychloroquine, a malaria drug that inhibits au-
 hydroxyl radicals, so a high Ce3+:Ce4+ ratio tophagy, affects Zika-infected pregnant mice and their offspring. Nonmodifed
 mice given hydroxychloroquine also had less placental and fetal damage than
 untreated pregnant mice. This finding suggests that the drug, which is ap-
 proved by the U.S. Food & Drug Administration for use in pregnant women to
 treat malaria and certain autoimmune disorders, prevents Zika from crossing
 the placenta barrier. Mysorekar hopes the work will lead to similar studies in
 nonhuman primates and, after that, people.—BETHANY HALFORD

 ORIGINS OF LIFE ters from Fe2+ and organic thiols (Nat.
 ▸▸ Plausible prebiotic Chem. 2017, DOI: 10.1038/nchem.2817).
 The researchers used glutathione, a cys-
 teine-containing tripeptide, as a source of
 route to iron-sulfur sulfur to make a model system. UV light

 in the particles is Ceria-zirconia
 clusters identified liberates sulfide from the glutathione
 and oxidizes Fe2+ ions to Fe3+. The sulfide
 important for treat- nanoparticles and ferric ions then combine to form the
 ing inflammation. (red) target Iron-sulfur clusters are important co- clusters. Because glutathione might not
 Shifting to the +3 inflammation in factors required for the catalytic sites have existed on early Earth, the research-
 oxidation state is the intestine of a of various enzymes. Researchers have ers also tested other cysteine-containing
 energetically unfa- mouse with sepsis hypothesized that such clusters may have tripeptides and found that most of them
 vorable, however, (right) but do even been involved in the emergence of could stabilize Fe-S clusters. In addition,
 so the researchers not enter healthy biological catalysis on early Earth. Such they showed that formation of the clus-
 added Zr4+ ions to tissue (left, blue). a role would have required spontaneous ters is compatible with fatty acid vesicles
 the nanoparticles formation of these clusters from environ- used to model early, simple cells.—CELIA
 to stabilize the Ce3+:Ce4+ ratio and improve mental sources, so identifying a plausible ARNAUD
 their antioxidant capabilities over ceria-on- route has been a ma- h 
 ly nanoparticles (Angew. Chem. Int. Ed. jor goal in the field RS– HS–
 2017, DOI: 10.1002/anie.201704904). The of prebiotic chem- Fe2+ RS SR
 S
 team tested the ceria-zirconia nanoparti- istry. Now, Sheref Fe 3+ Fe3+
 cles in cell and animal models of inflam- S. Mansy of the SR SR RS S SR
 RS RS
C R E D I T: A NG EW. CH EM . I N T. ED.

 h 
 mation and sepsis and discovered that University of Trento Fe2+ Fe3+
 the nanoparticles targeted inflammation, and coworkers have RS SR RS SR
 reduced ROS, and prolonged the survival identified one such –
 RS = organic thiolate
 of mice with sepsis with only a single, low plausible route.
 dose. The authors note that the nanopar- They report that UV In this proposed mechanism for the prebiotic synthesis of
 ticles “have the potential as a therapeutic light can drive the iron-sulfur clusters, UV light releases sulfides from organic
 nanomedicine for treating ROS-related in- synthesis of [2Fe-2S] thiolates and oxidizes ferrous iron to ferric iron. The resulting
 flammatory diseases.”—EMMA HIOLSKI and [4Fe-4S] clus- complex forms iron-sulfur clusters.

 JULY 17, 2017 | CEN.ACS.ORG | C&EN 11

CHEMISTRY Do science, take

 IN PICTURES pictures, win money.
 Enter our photo contest at
 cen.chempics.org or e-mail
 cenchempics@acs.org.
 Selections from cen.chempics.org,
 where C&EN showcases the beauty of chemistry

 And now for some culture
 For this drawing, Cinae Collins didn’t use paints or
 pencils; she used three species of bacteria to recreate
 Vincent van Gogh’s “The Starry Night.” Collins, a senior
 at Homewood-Flossmoor High School in Illinois, drew
 the image on a plate of blue-dyed agar gel using swabs
 of cultures of Serratia marcescens, Micrococcus luteus,
 and Bacillus cereus. After about a day, in the places
 where she’d swabbed the bacteria, dark blue, yellow, and
 white spots and swirls—which are actually colonies of
 S. marcescens, M. luteus, and B. cereus, respectively—
 emerged, revealing her image.—MANNY MORONE

 Submitted by Kim Smith and Cinae Collins

 Gel crystals
 When growing crystals, often the slower
 you go, the bigger the crystals you get. High
 school student Will Paulien grew these
 crystals in his AP chemistry class from a
 Flinn Scientific kit called “Growing Crystals
 in Gels.” The gel slows down the chemical
 reactions by limiting diffusion between one
 reagent suspended in the gel and a second
 reagent, which is placed on top of the gel.
 This set shows crystals of, left to right,
 lead(II) iodide, metallic lead, and iron(III)
 chloride.—CRAIG BETTENHAUSEN

 Submitted by Will Paulien

12 C&EN | CEN.ACS.ORG | JULY 17, 2017

Immiscible rainbow
 It takes careful planning and technique to prepare this
 chemical rainbow. To learn about density and miscibility,
 freshmen chemistry students at Georgia Tech created
 this colorful demonstration by assembling layers of
 dyed solvents with different densities. They snapped a
 picture of the tube in front of the Atlanta skyline.
 The students used the following solvents, from top to
 bottom (least to most dense):
 ▸▸Ethyl acetate
 ▸▸Deionized water
 ▸▸1:1 ethyl acetate:dichlorobenzene
 ▸▸Dilute aqueous calcium chloride
 ▸▸Dichlorobenzene
 ▸▸Concentrated aqueous calcium chloride
 —CRAIG BETTENHAUSEN

 Submitted by Jennifer Hill

Squishing liquid crystals
 Classically, liquids are disordered
 and their molecules don’t organize
 into any particular structure. But
 some chemicals, such as this
 dibenzophenazine derivative, can
 form liquid crystals, in which the
molecules partially organize into larger
structures. In this case, the molecules
 are wide and flat enough to stack into
 columns. Vance Williams, a professor
 at Simon Fraser University, captured
 this image while looking at the
 liquid crystals under a polarized light
 microscope and squishing the sample
 under the coverslip. The pressure
disrupted the stacking of the columns,
 leading to these swirling structures.
 The rainbow of colors is the result of
 the polarized light traveling through
 the different orientations of the
 birefringent columns in the squished
 liquid crystal.—MANNY MORONE

 Submitted by Vance Williams

 JULY 17, 2017 | CEN.ACS.ORG | C&EN 13

Business Concentrates INSTRUMENTATION

 REGULATION Agilent buys into
 Europe reexamines Raman spectroscopy
 Merck’s Sigma buy Agilent Technologies has entered the Raman spectroscopy mar-
 ket with the acquisition of the British firm Cobalt Light Systems
 for about $52 million.
 European antitrust regulators have charged Merck KGaA Based in Oxfordshire, En-
 with holding back important information before complet- gland, Cobalt was formed in
 ing its late-2015 acquisition of lab chemicals maker Sig- 2008 as a spin-off from the
 ma-Aldrich for $17 billion. U.K. Science & Technology
 The lapse won’t scuttle the two-year-old deal that Facilities Council. Today it has
 formed the research chemicals powerhouse MilliporeSig- 52 employees and claims as cus-
 ma, but it could result in a fine of up to $165 million, equal tomers 20 of the 25 largest drug
 to 1% of Merck’s annual revenues. companies and more than 75
 In applying for approval of their merger, Merck and airports across Europe and Asia. Cobalt’s product line includes
 Sigma-Aldrich didn’t reveal information about newly devel- Cobalt’s products are bench- this handheld device.
 oped technology affecting “certain laboratory chemicals,” top and portable Raman spec-
 the European Commission says. Had regulators known trometers that allow identification of chemicals and materials
 about the technology, the commission says, they would without opening containers. Applications include materials
 have ordered it to be divested along with the manufactur- identification in pharmaceutical quality control and screening of
 ing assets and lab chemical brands that they required to be containers for explosives in airport security checks.
 sold for antitrust reasons. Honeywell bought the assets and Conventional spectroscopy is poor at detecting materials
 brands in October 2015. through sealed, nontransparent containers. With the acquisi-
 The commission didn’t disclose the technology, saying tion, Agilent gets Cobalt’s spatially offset Raman spectroscopy
 only that it “was closely linked to the divested business (SORS) technology. Invented by a group at the Science & Tech-
 and had the potential to substantially increase its sales.” nology Facilities Council that included Cobalt’s chief scientific
 A Merck spokesperson says the technology, not yet on officer, Pavel Matousek, SORS uses two or more measurements
 the market, involves a packaging innovation “which to obtain greater Raman contribution from the contents than the
 has several potential applications outside the divested container.
 portfolio.” A second Cobalt technology, transmission Raman spectroscopy
 Merck ultimately licensed the technology to Honeywell (TRS), is an alternative to conventional chemistry-based analyt-
 “free of charge” a year after the acquisition closed and after ical testing such as HPLC. TRS takes seconds per drug tablet or
 Honeywell told the commission of the disclosure lapse, the capsule and does not require preparative steps, the firm says.
 spokesperson says. Paul Loeffen, Cobalt’s CEO, says the combination of his firm’s
 Merck counters that it acted in good faith and “is con- patented technology with Agilent’s product-development know-
 fident this issue will be resolved in a satisfactory man- how, manufacturing skills, and customer base “will allow us to
 ner.”—MARC REISCH scale our operations to take advantage of this rapidly growing
 market.”­—MICHAEL MCCOY

REGULATION

FDA shifts on rare-disease drug approval
In a change of heart, the U.S. Food & Drug data. The company did not expect to com- calling for “slashing the restraints” on FDA.
Administration has told Amicus Thera- plete the study until 2019. Moreover, newly appointed FDA Com-
peutics it can seek approval for its Fabry Now, Amicus will file for regulatory missioner Scott Gottlieb has in the past
disease treatment migalastat. Shares of the approval in the U.S. in the fourth quarter, made clear he thinks the agency could be
rare-disease-focused biotech firm soared potentially putting the drug on more progressive in how it re-
by more than 25% on news of the regulato- the market in the second half of HO views drugs for rare diseases.
 NH
ry shift, which trims at least three years off 2018. FDA’s changed stance on Leerink Partners stock an-
 C R E D I T: CO BA LT LI G HT SYST E MS

 OH
the development time for the drug. migalastat, which is already ap- HO alyst Joseph P. Schwartz told
 Migalastat stabilizes the enzyme re- proved in the European Union, OH investors that he “cannot rule
sponsible for breaking down globotriaosyl- prompted much speculation out the political influence of
 Migalastat
ceramide (GL-3), a fatty substance that ac- from industry insiders. In a a new Administration (and
cumulates in the lysosomes of people with February address to Congress, President its inclination toward approving med-
Fabry disease. In November, FDA asked ­Donald J. Trump highlighted Amicus CEO icines for deadly afflictions) having an
the company to conduct a new study of John Crowley’s daughter Megan, who has influence” on the announcement.—LISA
the drug to collect more gastrointestinal Pompe disease, another rare disease, while JARVIS

14 C&EN | CEN.ACS.ORG | JULY 17, 2017

INTELLECTUAL PROPERTY
 ELECTRONIC MATERIALS

 Chemical Broad jump-starts
 makers CRISPR patent pool
 invest in chip Utility of one-stop patent shop
 hinges on wider participation
 materials Seeking to simplify the
 increasingly complex
 firms connected to its
 CRISPR/Cas9 inventors
 During Semicon West, a trade show patent landscape for Jennifer Doudna and
 for semiconductor manufacturing the gene-editing tech- Emmanuelle Charpen-
 materials and equipment held in nique CRISPR/Cas9, tier, now at the Max
 San Francisco July 11–13, multiple Broad Institute of MIT Planck Institute for In-
 chemical makers announced deals & Harvard has applied fection Biology. Those
 or investments intended to serve to place its patents into companies include
 makers of advanced computer chips. a new pool that would CRISPR Therapeutics,
 High-end cleaning was the sub- provide nonexclusive Caribou Biosciences,
 ject of two announcements. Versum licenses for commercial and ERS Genomics.
 Materials said it will pay $13 million users. In turn, those firms
 to acquire Dynaloy, an Eastman However, so far the sell licenses to other
 Chemical business that supplies for- University of California, companies.
 mulated cleaning products to semi- Berkeley, the other big For example, ERS
 conductor makers. Versum, which patent owner, has not Genomics granted Du-
 is Air Products’ former electronic signaled that it will Pont Pioneer an exclu-
 materials business, says Dynaloy participate in the pool. Broad Institute is a major sive license to its CRIS-
 will complement its existing surface Indeed, Broad and UC CRISPR/Cas9 patent owner. PR-Cas9 patents for ag-
 preparation and cleaning materials Berkeley have been riculture applications.
 business. engaged in a high-stakes patent fight since That means that other agriculture biotech
 Mitsubishi Gas Chemical said late last year. And Berkeley is waiting for a firms must work with Pioneer—a potential
 it will spend $60 million to build ruling on its CRISPR/Cas9 patent applica- competitor—to use the technology.
 plants in Oregon and Texas that tion by the U.S. Patent & Trademark Office. “We seriously consider all requests for
 produce ultrapure hydrogen perox- For biotechnology companies seeking sublicenses to the intellectual property
 ide, used in the electronics industry to use the gene-editing tool, a patent pool under DuPont Pioneer’s control, and
 for cleaning, etching, and abrading could be a one-stop shop providing access terms are tailored on a case-by-case basis,”
 semiconductor wafers. MGC already to multiple patents under one license. In- says Neal Gutterson, vice president of
 operates similar facilities in Arizona stead of granting exclusive rights, the pool R&D for DuPont Pioneer.
 and at four sites in Asia. would give licenses to all companies and Pioneer and other firms that control
 Cutting-edge materials for apply the same pricing scheme. CRISPR intellectual property say they
 next-generation chip circuitry got a But according to Jorge L. Contreras of ­favor wide use of CRISPR/Cas9 technol-
 lot of attention. The start-up com- the University of Utah College of Law, ogy, but they have not voiced support
 pany Inpria said it secured $23.5 mil- most applications using CRISPR might for a patent pool. Contreras suggests
 lion in series B funding from inves- need both Broad and Berkeley patents. that ­support for a pool may be limited to
 tors including Air Liquide, Applied “The most effective pools are the ones firms in gene-editing tool development,
 Materials, Intel, JSR, and Samsung. that have substantially all of the patent CRISPR reagents, or smaller applica-
 Inpria, one of C&EN’s 10 Start-ups holders there,” he says. tions such as animal health.—MELODY
 to Watch last year, said it will use Berkeley has already licensed patents to BOMGARDNER
 the money to scale up output of its
 tin oxide-based photoresists.
 Brewer Science and Arkema ex-
 tended a collaboration to develop BY THE NUMBERS Proportion of new car sales

 54%
 materials for directed self-assembly that will be electric vehicles (EVs) by
 of chip circuitry using high-χ block 2040, according to Bloomberg New
 copolymers. And the industrial gas- Energy Finance. The market analysis
 es maker Linde said it is expanding firm expects consumer adoption of
C R E D I T: A N TO N G RAS S L

 production of neon for use in deep EVs to accelerate between 2025
 ultraviolet lithography and xenon and 2030. The firm increased its
 for etch applications in three-di- forecast this year because of faster-
 mensional semiconductors.—MI- than-expected reductions in battery
 CHAEL MCCOY costs and new commitments from
 automakers.

 JULY 17, 2017 | CEN.ACS.ORG | C&EN 15

Business Concentrates
 SPECIALTY CHEMICALS
PETROCHEMICALS
▸▸ Total brings ethane Arkema invests in Asia
 French chemical maker Arkema will invest in three projects in Asia as part
to Antwerp cracker of a plan to drive up its share of sales from specialty chemicals to more than
 80% by 2023. The largest project will be a $350 million biobased nylon 11
The French oil company Total has upgrad- plant to be built at an undisclosed Asian location for applications including
ed one of two steam crackers at its site in automotive, three-dimensional printing, and consumer goods. The project
Antwerp, Belgium, to use ethane as a raw will increase the firm’s global capacity for nylon 11 by 50%. Arkema also plans
material. Ethane, butane, and naphtha to double its capacity for methyl mercaptan, an intermediate used in animal
are all now potential feedstocks for the feed, petrochemical, and refining applications, at its site in Kerteh, Malaysia.
 The new capacity is due to come onstream in 2020. In a third project, Arke-
 ma will increase capacity at its Sartomer photocure resins facility in Nansha,
 China, by 30%. Due to open in early 2019, the additional capacity will help
 meet Asian customer demand in electronics, 3-D printing, and ink-jet print-
 ing markets, Arkema says.—ALEX SCOTT

 its existing alkylation, sulfonation, and duce ethanol from refinery off-gases. The
 sulfation technologies. ATRP is based 35,000-metric-ton-per-year plant will be
 on the work of Krzysztof Matyjaszewski, installed at the Panipat refinery in Hary-
Total will ship plant, the company a professor of chemistry at Carnegie ana at a cost of about $55 million. Lanza-
ethane into its says. The upgrade is Mellon University who received a 2009 Tech’s microbes ferment waste carbon
Antwerp complex part of a $60 million Presidential Green Chemistry Challenge monoxide and dioxide into ethanol. The
from Norway. project that includes Award for developing the copper-mediat- firm operates two demonstration facilities
 adapting the site’s ed polymerization technique. ATRP CEO in China that make the fuel from steel mill
terminal to import up to 200,000 metric Patrick McCarthy, who started the firm 11 emissions.—MELODY BOMGARDNER
tons of ethane per year by ship from Nor- years ago, will remain with ATRP in Pitts-
way.—MICHAEL MCCOY burgh.—MARC REISCH
 AGRICULTURE
MERGERS & ACQUISITIONS WATER ▸▸ NewLeaf raises
▸▸ Italmatch buys ▸▸ Mitsubishi sets up $24 million for microbes
metal separation firm Myanmar venture NewLeaf Symbiotics raised $24 million
 in its third round of venture funding to
The Italian chemical maker Italmatch has Mitsubishi Chemical has formed a joint commercialize agricultural products based
acquired Magpie Polymers, a spin-off from venture with a local firm in Myanmar to on methylotrophic bacteria. Investors
Paris’s École Polytechnique that specializ- provide water treatment services in the included Monsanto Growth Ventures, Ot-
es in the recovery of precious metals from country. Wellthy, a Mitsubishi subsidiary, ter Capital, and Lewis & Clark Ventures.
industrial wastewater. Magpie’s filtration has been testing processing equipment NewLeaf ’s microbes convert methanol, a
process is based on a resin that selective- that can treat the highly turbid and salty waste product of plant metabolism, into
ly recovers metals, including palladium, river water available around Yangon, the nutrients that support plant growth, the
platinum, silver, and gold, that otherwise former capital of Myanmar. Mitsubishi company says. It plans to develop seed and
would be lost in wastewater from process- notes that Myanmar has an urgent need soil treatment applications. In addition,
es such as mining. Magpie claims its tech- for equipment that can produce safe NewLeaf will triple the size of its R&D
nology performs better than ion-exchange drinking water and treat sewage. The new and pilot facility in St. Louis.—MELODY
resins.—ALEX SCOTT venture will also provide water analysis BOMGARDNER
 services.—JEAN-FRANÇOIS TREMBLAY

POLYMERS PESTICIDES
 BIOFUELS
▸▸ Pilot Chemical buys ▸▸ BASF will launch
ATRP Solutions ▸▸ LanzaTech takes new malaria nets
 its process to India
 C R E D I T: TOTA L

Pilot Chemical has acquired the atom BASF is preparing to introduce mosquito
transfer radical polymerization specialist LanzaTech and India’s national oil com- nets that feature the pyrrole insecticide
ATRP Solutions. Cincinnati-based Pilot pany, Indian Oil, plan to build what they chlorfenapyr, which according to the
says the deal adds a new chemistry to say will be the world’s first facility to pro- company is the first completely new insec-

16 C&EN | CEN.ACS.ORG | JULY 17, 2017