vishakhapatnam, india february 2017 - industrial green ... conference...is in galvanizing steel for...

ACS Green Chemistry Institute®

Green Chemistry and Engineering: Enabling

greater business value for an environmentally

responsible Pharma supply chain

American Chemical Society

David J. C. Constable, Ph.D.

Science Director, ACS Green Chemistry Institute®

Vishakhapatnam, India

February 2017

ACS Green Chemistry Institute®American Chemical Society

Asking the Right Questions is Imperative

Avoid “the perfect uselessness of

knowing the answer to the wrong

question”

The Left Hand of Darkness

Ursula K. LeGuin

1969


Sustainability Risks are Real

THE BIG DRIVERSHow do you view the world?

• Plenty of resources vs. finite and diminishing resources?

• Room for lots more people vs. too many people?

• The environment will take care of itself vs. the environment is stressed?

• Life as I know it will continue on just as it always has vs. disruptive change?



Engaging you to reimagine chemistry and engineering for a sustainable future.


We believe sustainable and green

chemistry innovation holds the key to

solving most environmental and human

health issues facing our world today.

• Advancing Science

• Advocating for Education

• Accelerating Industry


Why Reimagine Chemistry?

• The global chemistry enterprise as currently

operated is completely unsustainable:

– Feedstocks – What we start with

– Chemicals

– Chemistries How we put things together

– Processes

– Products

Chemists and chemical engineers are

uniquely equipped to do something about

making the world more sustainable



Outsourcing is typically driven by cost, need for flexibility, increasing

capabilities of CMOs. For companies producing chemical APIs, 46%

outsource more than half of their needs.


A few (of many) Sustainability Risks

• New products

• Price controls

• Pandemics

• Access to medicines

• Animal testing

• Clinical trial results

transparency

• Product Safety

• Counterfeiting

• Generics

• Bioprospecting

• Diseases of the developing

world

• Preferential pricing

• Informed Consent

• Sales practices

• Energy

• Genetic testing

• Climate Change

• Pharmaceuticals in the

Environment

• Etc.


Policy Issues – Governmental, Industrial, Societal

• Green vs. Sustainable

• Regulation (Toxic Use Reduction) vs. Technology

(Innovation)

• Mandatory vs. Voluntary

• Federal vs. State (v. International)

• Banning certain chemical use vs. alternatives

development

• Burden of Proof and changes in chemicals testing

(toxicology)

American Chemical Society 8


Supply of Critical Elements is not Sustainable

50% of all Zn is

used to

galvanize steel

for corrosion

resistance; 5-50

years of Zn are

left at current

rate of

consumption

Global production of

Sn = 140 tonnes; if

current consumption

continues, 5-50

years of Sn are left

Rh is one of the rarest

elements in the Earth’s

crust accounting for

0.0002 parts per million;

only 5-50 years of Rh

are left.


PGM

supply of many “technology metals” is price-inelastic:

• Increased demand can only be met by primary production if demand for

major metal rises accordingly

• Short term demand surges lead to price peaks (see Ir, Ru, In)

• Effective recycling important for supply security

Metal families – most precious and specialty

metals are coupled to major metals production


• 23rd most abundant element in the Earth’s

crust

• Makes up an average of 65 grams for every

ton of the Earth’s crust

• Commercially exploitable reserves exceed

100 million tons

• Chemically used in a variety of chemistries

and as a catalyst in the form of zinc oxide

• One of the most common uses (50%) of zinc

is in galvanizing steel for corrosion

resistance

• Estimated 5-50 years Zinc left if

consumption continues at current rate

Zinc Dwindling Supply of a Useful Metal


Tin Has Many Important Uses

Uses:

• Coatings for metals as component in corrosion inhibition, protective

oxide layer that prevents further oxidation

• Historically used in formulations of marine anti-foulants

• Used in a number of catalyst systems

• Component in solder for electronics

Abundance

• Global production of tin is more than 140 tonnes per year

– Reserves are approximately 4 million tonnes.

– An estimated 130 tonnes of tin concentrates are produced each

year.

• If current consumption continues, 5-50 years of Tin are left


Example by-product element: indium (demand)

Uses of indium

Thin films: transparent and conductive coatings of indium tin oxide (ITO) for

- liquid crystal displays (50% of In use!)

- flat panel displays

- touch screens

- photovoltaic cells

- smart windows

- …


Source: Ch. Hagelueken

(Umicore)

Demand is rising sharply

Recycling challenge: Very small quantities per unit, but many units


Rhodium is Not Abundant• Found mainly in South Africa (60%) and Russia. Also found in

the state of Montana, U.S.A.

• The annual world production of rhodium is around 16 tonnes a

year with an estimated reserve of 3 tonnes

• It is one of the rarest elements in the Earth’s crust as it accounts

for only 0.0002 parts per million

• If this element is used at the rate it is consumed now, only 5-50

years of rhodium are left

• 82.7% of Rhodium used as a catalytic converter for cars and

used extensively in many catalytic reactions

• Finish for jewelry, mirrors, and search lights as it is highly

reflective; manufacture of nitric acid; hydrogenation of organic

compounds; alloying agent for hardening and improving the

corrosion resistance of platinum and palladium


The Socio-Economic Cost Of Mining Pt Group Metals Is High

“South African platinum miners must

return to work Monday, despite 34

strikers killed by police”ASSOCIATED PRESS AND REUTERS | Aug 19, 2012 11:51 AM ET

“The world's second-largest platinum miner,

Johannesburg-listed Impala Platinum Holdings

Ltd., fired more than 17,000 striking workers in

February, sending the price to a year-to-date

high over $1,600 an ounce. The 12-month high

is around $1,900 an ounce.”

By 24/7 Wall St.

Posted 8:33AM 08/17/12

http://news.nationalpost.com/author/associatedpressnp/

http://news.nationalpost.com/author/reutersnp/

http://www.dailyfinance.com/writers/24-7-wall-st/


Cheap Phosphorus Won’t be Available Forever

Endangered Species: Should Cheap Phosphorus

Be First On an Elemental 'Red List?'

ScienceDaily (Oct. 13, 2011) — Should the periodic

table bear a warning label in the 21st century or be

revised with a lesson about elemental supply and

demand?http://www.sciencedaily.com/releases/2011/10/111014104948.htm

James Elser,

Elena Bennett.

Phosphorus cycle:

A broken

biogeochemical

cycle.

Nature, 2011;

478 (7367): 29

DOI:10.1038/478029a

http://phosphorusfutures.net/

http://www.sciencedaily.com/releases/2011/10/111014104948.htm

http://dx.doi.org/10.1038/478029a

http://phosphorusfutures.net/


A Few Challenges Facing the

Batch Chemical Industries


There are Large Challenges

• Some traditional sticking points:

– Infrastructure

– Double Death Valley

– In ground capital

– Economics / financial analysis

– Current business climate

– Societal / Organizational

– Bigger SD / CSR issues dominate senior executive agendas

– Educational system

– Resistance to change and risk aversion

– Maintaining status quo


Chemists Use Old Chemistries

A random selection of 100 chemistries in a review of named reactions:

54% before World War 1

74% before World War 2

91% before 1975

9% during the 1980’s

Wurtz, Charles Adolphe

Born: Wolfisheim, 1817

Died: Paris, 1884

Williamson,

Alexander William

Born: London, 1824

Died: Hindhead, 1904

Grignard, François Auguste

Born: Cherbourg, 1871

Died: Lyon, 1935


Chemical Technology Hasn’t Changed Much

• Batch reactor

• Distillations

• Crystallisation

“The difficulty lies, not in the new ideas, but in escaping the old

ones, which ramify, for those brought up as most of us have

been, into every corner of our minds.”

- John Maynard Keynes

Bronze age

e.g., Dutch gin was

imported before the

English industry for

distilled spirits took over

in the 18th century

Salt crystallisation during

bronze age


Current Batch Chemical Process Development is Complicated

• Large portfolios

• Significant route modifications or complete

substitution

• Incremental optimisation of chemical

processes

• Focus on yield, quality, CoG and number of

steps


Reasons We Use the Chemical Building Blocks We Use

Because they:

– Ensure thermodynamically and kinetically favorable

reactions

– Result in the highest yields

– React in predictable ways

– Are “easily” obtained (lowest cost)

– Generally don’t require sophisticated reactors or technology

in the laboratory

But….


These Chemical Building Blocks have a few Sustainability Risks

• Feedstocks

• Process efficiencies

• Missing Data

• High-hazard materials

• High risk process chemistries

• Inappropriate engineering or process controls

• Human and Environmental Exposures

• Legislation/regulations


Thinking About Design

“Design is a signal of

intention”“Cradle to Cradle”

William McDonough

2002


Sustainability Needs to be Designed into Products and Processes

• If we want to make the biggest impacts to products,

services and costs, we have to start from the ground up.

• If we want to build sustainability into the design of

products and services we have to think differently about

the what and how of R&D.

• Increasing demands and decreasing budgets are likely to

mean greater reliance on easily accessible company-

wide tools that provide early assessments and highlight

sustainability issues.

• Implementing more sustainable practices requires

patience and persistence.


Finding the Right Balance is Challenging

Commercial

Focus on

Speed to

Market

Sustainable process

design early when

costs are lower

Attrition


Simplified*, Principles of Green Chemistry and Engineering

• Maximize resource efficiency

• Eliminate and minimize hazards and

pollution

• Design systems holistically and using

life cycle thinking*See: Green Chemistry and Engineering: A Practical Design Approach. Jimenez-

Gonzalez C, Constable DJC. John Wiley and Sons. 2011, p 35- 37.

http://www.amazon.com/Green-Chemistry-Engineering-Practical-Approach/dp/0470170875

…. but remember that Principles aren’t metrics!


ACS Green Chemistry Institute®American Chemical SocietyAmerican Chemical Society


Innovation is Essential



A Change Model Supporting Innovation

Things could

Be better

I can see

what might

be done

I need a

convincing

demo

The budgetary hurdle

This is the

way I do

things

My best people

can deliver

I know when to

do this

I have the

skill base to

do regularly

Effort

Innovation progress


The Market for Green Chemistry is Expanding

The green chemistry market will grow from $2.8 billion in

2011 to $98.5 billion in 2020.


Innovations are Needed EverywhereThe laboratory

• Development laboratories are full of batch equipment.

They need to contain:

- Plug-and-play continuous equipment

- Infrastructure to feed, monitor, control, acquire data

from continuous devices

- Ubiquitous property and kinetic measurement

capability

The chemist and the engineer

• Whole process thinking is needed

• New skill sets need to emerge with new ways of

processing:

- Existing “batch” skill sets are effective but restricted

- Early and effective communication between chemist

and engineer is essential to identify process options

- Increased pressure on quantitative skills – newer

process equipment designs are less forgiving

• New ways of developing and optimising processes

are needed

Business processes

• Valuing process robustness and quality

• Valuing EHS benefits in DfM

• Planning development activities to allow for working faster

• Taking a portfolio vs. product perspective

• Innovation implies more technical decisions to be taken earlier

Other Resources

• Money/Investment to change!

• Equipment, Time and Information availability

• Software / modelling tools

• Complexity


Success Stories in Sustainable Innovation


CASE 1: DOW & BASFPGCCA Winners for Greener Synthetic PathwaysHydrogen Peroxide to Propylene Oxide Process


Sustainable Polymers and Composites: Optimal Design

• Among the top 30 largest-

volume chemical

intermediates produced in

the world

• Annual worldwide demand

is estimated to be over 14

billion pounds

• Key raw material for PU,

propylene glycols, glycol

ethers, etc.

U.S. EPA

http://www2.epa.gov/green-chemistry/2010-greener-synthetic-pathways-award


Impact of HPPO Process

• This new route to make propylene oxide with hydrogen peroxide

(Solvay’s advanced anthroquinone autooxidation process) that eliminates most of the

waste and greatly reduces water and energy use compared to

traditional technologies

• Wastewater reduced up to 80%

• Energy use reduced by 35%

• Production facilities are up to 25 % cheaper to build

Process Precursors IntermediateCoproducts/Recycle

t/t PO

PCH POCl2, H2O HOCl, PCH ≥ 2 t Chloride salts

≥ 40 t H2O

SM PO Ethylbenzene EB-hydroperoxide ≥ 2.2 t Styrene

MTBE PO Isobutane t-Butylhydroperoxide ≥ 2.4 t t-Butanol

Cumene PO Cumene Cumene-hydroperoxide ≈ 1.5 t Cumyl-alcohol

HPPO H2, O2 H2O2 ≥ 0.3 t H2O

DOI: 10.3303/CET1021096

http://www.aidic.it/cet/10/21/096.pdf

http://www.aidic.it/cet/10/21/096.pdf


CASE 2: ELEVANCE RENEWABLE SCIENCES, INC.

PGCCA Winner in the Small Business Category


Proprietary Metathesis Technology

A

methyl oleate

C

ethylene

Elevance Proprietary Catalyst

D

B

Catalyst

C

9-decenoic acid methyl ester

D

1-decene

A

B

A

C

methyl oleate

methyl oleate

D

Catalyst

B

C

9-octadecenedioic acid methyl ester

A

D

9-octadecene

B


Elevance Advantage: Superior Process

Feedstock Options

Soy oil

Palm oil

Canola oil

Corn oil

Jatropha

Algae

Tallow

Mustard oil

Nobel Prize-Winning Technology

Co-Reactants

Metathesis

ERS proprietary biorefinery process

Existing Biodiesel

Asset

Distillation

Transesterification

Standard Chemical

Unit Operations

DerivatizationSeparations

Alcohol

‘Drop In’ and

and Specialty Products

Glycerol

Distillation

Hydrolysis/Hydrogenation

Specialty Chemicals

Olefins

Oleochemicals


ImpactEconomic Benefits

• Elevance’s biorefinery results in lower production costs, energy consumption, and

capital expenditures than petrochemical refineries

• Elevance addresses a market of $176 billion in the specialty chemicals industry

Platform Market Segment Addressable Market Size

Consumer Ingredients

& Intermediates

Detergents and cleaners $20 billion

Personal care products $6 billion

Performance waxes $5 billion

Lubricants & AdditivesLubricant base oils $17 billion

Lubricant and fuel additives $12 billion

Engineered Polymers

& Coatings

Specialty polyamides, polyesters, and polyols $25 billion

Epoxies and polyurethanes $58 billion

Coatings and cross linking agents for coatings $33 billion

• Consumer Impact Example: Detergents

o Elevance’s specialty chemicals enable detergents that have more concentrated

formulations and improved solvency (better cleaning) while working in cold

water (reduced energy costs)


CASE 3: MYRIANTCommercializing Bio-Based Chemicals


Bio-Succinic Acid “Drops-In” to Chemical Manufacturing to Replace Petroleum

• High Value

• Proven Chemistry/Scale

• High Performing

• Cost Competitive

• Better Environmental Footprint

• Extensive IP

$7.5BSuccinic Acid

Market

SAC Replacement

BDO

PBS

Serving Immediate Demand in Multiple Application Markets

MyriantBio-Succinic Acid

Molecule


Myriant’s Bio-Succinic Acid Value Proposition

• Bio-succinic Acid Process Has Low Greenhouse Gas Emissions

94% less than petrochemical succinic acid*93% less than petrochemical adipic acid*

• Renewable Feedstocks are Cheaper and Less Volatile Than Petroleum

• Efficient Fermentation and Downstream Processes Optimize Production Costs

• Feedstock can be sorghum (non-food) based or corn based

• Drop-in Replacement Anywhere Succinic Acid is Currently Being Used

• Replaces petroleum based chemicals in Urethane, Plasticizer, Coatings and Polymer Applications


CASE 4: RICHARD WOOL, University of Delaware

2013 PGCCA Winner in Academic Category



New biobased materials substitutes for toxic substances used to make high-

performance materials, like adhesives, composites, and foams

Fatty acids

Triglycerides Lignin

Chicken feathersU.S. EPA

http://www2.epa.gov/green-chemistry/2013-academic-award



• Twinkling Fractal Theory

(TFT) to predict the

functional properties of a

material based on its

molecular properties

• Evaluates the potential

toxicity of the materials

using the U.S. EPA’s EPI

SuiteTM software

U.S. EPA

• Impact: requires less H2O, energy, & toxic waste vs.

traditional technologies

• Commercialization: Dixie Chemical & Crey Bioresins

http://www2.epa.gov/green-chemistry/2013-academic-award


ACS GCI Industrial Roundtables

Catalyzing the integration of sustainable and green chemistry and engineering in the global chemistry enterprise.


We convene companies from across the world to focus on the science

of sustainable and green chemistry and its implementation.

• Pharmaceutical

• Formulators

• Chemical Manufacturers

• Hydraulic Fracturing

• BioTechnology Leadership

ACS Green Chemistry Institute®American Chemical Society 50

Roundtable Member Companies

http://www.google.com/imgres?imgurl=http://biotechjobs.forceite.com/wp-content/uploads/2010/07/amgen_logo.jpg&imgrefurl=http://biotechjobs.forceite.com/&h=148&w=602&sz=27&tbnid=h4NGFTGHIUnQWM:&tbnh=33&tbnw=135&prev=/images?q=amgen+logo&zoom=1&q=amgen+logo&usg=__2HK-fWUklEZd5aw0UMPYG_d-Fsw=&sa=X&ei=elChTMCoAsL38AbJ4JD0Dw&ved=0CBwQ9QEwAw

http://www.google.com/imgres?imgurl=http://biotechjobs.forceite.com/wp-content/uploads/2010/07/amgen_logo.jpg&imgrefurl=http://biotechjobs.forceite.com/&h=148&w=602&sz=27&tbnid=h4NGFTGHIUnQWM:&tbnh=33&tbnw=135&prev=/images?q=amgen+logo&zoom=1&q=amgen+logo&usg=__2HK-fWUklEZd5aw0UMPYG_d-Fsw=&sa=X&ei=elChTMCoAsL38AbJ4JD0Dw&ved=0CBwQ9QEwAw

http://www.codexis.com/

http://www.codexis.com/

http://en.wikipedia.org/wiki/Image:SC_Johnson_Logo.png

http://en.wikipedia.org/wiki/Image:SC_Johnson_Logo.png

http://www.virox.com/default.aspx

http://www.virox.com/default.aspx


Conclusions• There’s a lot going on in green and sustainable chemistry in the

United States (and the rest of the world)!

• While there is a lot of “sustainable” and “green chemistry” policy

and legislation, it is not addressing fundamental drivers of

challenges and is mired in uncertainty and controversy

• Sustainable and Green chemistry is more than just hazard and

pollution reduction. Should think about sustainable resource

consumption, incorporating systems and life cycle thinking.

• Innovation is key to making chemistry greener and more

sustainable

• Early design that incorporates sustainable and green chemistry

and engineering principles is imperative to achieve the most

cost effective gains

• There are many examples of success despite negative

perceptions associated with sustainable and green chemistry


Making Our Way to a Sustainable Tomorrow



Questions?

David J. C. Constable

[email protected]

What’s Your Green Chemistry? TM

We want to hear your story. Contact [email protected]

mailto:[email protected]

vishakhapatnam, india february 2017 - industrial green ... conference...is in galvanizing steel for...

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