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Green Chemistry University Curriculum Webinar Amy S. Cannon, Ph.D. Executive Director Beyond Benign @Amy_Cannon Karolina Mellor, Ph.D Program Manager Center for Green Chemistry and Green Engineering at Yale

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Page 1: Green Chemistry University Curriculum Webinar

Green Chemistry University Curriculum Webinar

Amy S. Cannon, Ph.D.

Executive Director

Beyond Benign

@Amy_Cannon

Karolina Mellor, Ph.D

Program Manager

Center for Green Chemistry and Green

Engineering at Yale

Page 2: Green Chemistry University Curriculum Webinar

M a s s a c h u s e t t s - b a s e d

5 0 1 - c 3 n o n - p r o f i t

D e d i c a t e d t o g r e e n

c h e m i s t r y e d u c a t i o n

K - 1 2 & H i g h e r E d .

D e v e l o p c u r r i c u l u m

r e s o u r c e s c e n t e r e d

a r o u n d t h e p r i n c i p l e s

a n d p r a c t i c e s o f

g r e e n c h e m i s t r y

G r e e n C h e m i s t r y

C o m m i t m e n t

About Us

Natalie O’Neil, Ph.D.Program Manager

Higher Education

Beyond Benign

@natjoneil

C e n t e r a t Ya l e U n i v e r s i t y

C o m m i t t e d t o a d v a n c i n g

s c i e n c e , c a t a l y z i n g

i m p l e m e n t a t i o n ,

p r e p a r i n g t h e n e x t

g e n e r a t i o n , a n d r a i s i n g

a w a r e n e s s .

C e n t e r W e b s i t e

G l o b a l G r e e n C h e m i s t r y

W e b s i t e

M o l e c u l a r D e s i g n

R e s e a r c h N e t w o r k W e b s i t e

Page 3: Green Chemistry University Curriculum Webinar

Welcome to the Green Chemistry Commitment

Green Chemistry Education Webinar Series

Recording and supporting documents will be available:

https://www.beyondbenign.org/he-webinars/

Submit questions at any time during the webinar in the

Control/Chat box on the Control Panel

Natalie O’Neil, Ph.D.Program Manager

Higher Education

Beyond Benign

@natjoneil

Kimberly Chapman, B.A.Administrative Assistant

Center for Green Chemistry and

Green Engineering at Yale

Page 4: Green Chemistry University Curriculum Webinar

Join the conversation!

@beyondbenign @YaleGCGE#greenchemistry#GCCwebinars

https://www.facebook.com/beyondbenign/https://www.facebook.com/Center-for-Green-Chemistry-Green-Engineering-at-Yale-293818143965581/

Page 5: Green Chemistry University Curriculum Webinar

What is the GCC?

The Green Chemistry Commitment (GCC) is a consortium

program that unites the green chemistry community around shared

goals and a common vision to:

o expand the community of green chemists

o grow departmental resources

o share best practices in green chemistry education

o affect systemic and lasting change in chemistry education

https://www.beyondbenign.org/he-green-chemistry-commitment/

Page 6: Green Chemistry University Curriculum Webinar

Green Chemistry Swag

Page 7: Green Chemistry University Curriculum Webinar

Green Chemistry University Curriculum Webinar

Amy S. Cannon, Ph.D.

Executive Director

Beyond Benign

@Amy_Cannon

Karolina Mellor, Ph.D

Program Manager

Center for Green Chemistry and Green

Engineering at Yale

Page 8: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Center For Green Chemistry and Green Engineering at Yale

Page 9: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Global market for chemicals exceeded 3.5 trillion EUR in 2018.

While the chemical sales tripled in the last 15 years, OECD share decreased.

BRIICS countries (Brazil, Russia, India, Indonesia, China, and South Africa) increased from 13% to 28%.

Recent forecasts by American Chemical Council predict significant growth in chemical production in developing countries.

2018 World Chemical Sales -3.5 trillion EUR

Page 10: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Need for innovative approaches to reduce the use of hazardous chemicals throughout their industrial lifecycle in non-OECD countries

Holistic and wide-ranging action, innovation, and environmentally benign approaches with the goal of “zero waste”.

Leapfrogging to sustainability?

Build resilient infrastructure, promote sustainable industrialization, and foster innovation

Page 11: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

MISSION:To increase the general global awareness and capacities on deployable Green Chemistry approaches for the design of

products and processes that advance global environmental benefits throughout their life cycles.

THE GLOBAL GREEN CHEMISTRY INITIATIVE

Page 12: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

THE GLOBAL GREEN CHEMISTRY INITIATIVE: Participants

Page 13: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

UNIDO is the specialized agency of the United Nations that promotes industrial development for

poverty reduction, inclusive globalization and environmental sustainability

As of 1 April 2019, 170 Countries are Members of UNIDO Since the mid- 90s, UNIDO established a network of National Cleaner Production Centers (NCPCs).

+70 countries help businesses and governments to:

• Improve productive use of natural resources

• Minimize impact on nature

• Support communities & reduce risk (improve well-being of workers and communities)

Page 14: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

THE GLOBAL GREEN CHEMISTRY INITIATIVE

National Cleaner Production Center Network

Center for Green Chemistry & Green Engineering + Partners

Training, Awareness, Capacity, and Guidance

Target Audience

Government Industry NGOs Academia

Page 15: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

14Participating

Countries

750+ Participants

11International senior

green chemistry experts

Brazil*Colombia*Egypt*Serbia*South Africa*Sri Lanka*PeruUgandaGhanaRwanda EthiopiaFYR Macedonia Jordan Kenia

*Host Countries

Page 16: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Yale

George Washington

McGill Queens University

WBI

Philip Jessop

Green ChemisTreeFoundation

Nitesh Mehta

Nottingham University

Pete LicenceJohn WarnerAdelina Voutchova-Kostal

Audrey Moores C-J Li Tomislav Friscic

Paul Anastas

Philip Coish

Julie Zimmerman

Karolina Mellor

Amy Cannon

Beyond Benign

Page 17: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

1-Day Awareness Raising Workshops

5-Day Train-the-Facilitators Workshops

To strengthen national and regional Green Chemistry initiatives in partnering countries and to enable partners to become hubs for education and training in Green Chemistry

University CurriculumTo educate the new generation of chemists in Green Chemistry

Technology CompendiumA systematic review of current Green Chemistry technologies

Guidance DocumentA roadmap to Green Chemistry implementation for different stakeholders

PROJECT ACTIVITIES

https://www.global-green-chemistry-initiative.com

Page 18: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

• Introductory course for undergraduates.

• Collaborative effort with Beyond Benign.

• Released in the summer 2019 after revision from UNIDO, partnering countries universities, and green chemistry experts.

• Course is now implemented in 7 South African universities.

Yale-UNIDO University Curriculum

Page 19: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Yale-UNIDO University Curriculum- Overview

• It is still a chemistry course – There are atoms, molecules, chemical reactions, and long unpronounceable names!

• It is an environmental sustainability course focused on applying chemistry principles. There is a wide range of environmental and energy issues that are discussed.

• The course will place chemicals in the context of daily life and society.

• It is an analysis course. Students will learn how to use the tools of analysis to better understand and make science-based judgments about chemicals, materials, and products.

After this course students will be able to (i) analyze whether or not a chemical/chemical product is “green” and sustainable, and (ii) make recommendations on how chemicals and chemicals products can be improved to be greener.

Page 20: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

• Intended for faculty who are looking to include more green chemistry in their curriculum by changing:

Their entire course

Semester long course (27 lectures) with PowerPoint slides, readings, class exercises, homework assignments, 2 midterms, final exam, and answer keys.

Sections of their course

Bridging topics to energy, innovation, analytical chemistry, recycling, and biodegradation.

Or to include individual topics and examples or exercises

Can be used with organic, inorganic, and general chemistry curriculum.

• Diverse multimedia content that encourages team work and hands-on learning.

• Copyright free.

Yale-UNIDO University Curriculum-Structure

Page 21: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

How to use the course materials?

Intro to GC course

Supplement with a

Module

HW’s and Exams

Supplemental Resources

Introduce a Case Study

Page 22: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Topics

• Introduction and Principles [Lectures 1-3]

• Chemistry Intro [Lectures 4-7]• Molecules, drawing, nomenclature, stoichiometry and reactions, metrics

• Sustainability and Life Cycle assessment [Lectures 9-10]

• Renewable feedstocks [Lecture 12]

• Designing for recycling & degradation [Lecture 14]

• Catalysis, Solvents [Lectures 15-17]

• Energy [Lecture 19]

• Green Analytical Chemistry [Lecture 20]

• Intro to toxicology, chemical exposure and dose, molecular toxicology [Lectures 21-23]

• Designing future products with reduced toxicity [Lectures 24-26]

• Real-world case studies [Lecture 13]

Page 23: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

DescriptionOverview of lecture contents

Prior to Lecture

Readings

Topics to Cover in LectureDetailed topic list within lecture materials

Lesson Plan Contents

Videos

Page 24: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Class ExercisesListing of optional class exercises, including in-class discussions, hands-on activities or supplemental laboratory based exercises.

Page 25: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Center For Green Chemistry and Green Engineering at Yale

12 Principles of Green Chemistry

Lecture #3

Date:

Course #

Page 26: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

1. Waste Prevention2. Atom Economy3. Less Hazardous Chemical Synthesis. 4. Designing Safer Chemicals. 5. Safer Solvents and Auxiliaries. 6. Design for Energy Efficiency. 7. Use of Renewable Feedstocks. 8. Reduce Derivatives. 9. Catalysis. 10. Design for Degradation. 11. Real-time Analysis for Pollution Prevention. 12. Inherently Safer Chemistry for Accident Prevention.

Anastas, P. T.; Warner, J.C. Green Chemistry: Theory and Practice, Oxford University Press,1998

Outline: 12 Principles of Green Chemistry

Page 27: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Safer Solvents and Auxiliaries

The use of auxiliary substances (solvents, separation agents, etc.) should be made unnecessary whenever possible and, when used, innocuous.

Page 28: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Solvents account for the vast majority of mass wasted in syntheses and processes. Moreover, many conventional solvents are toxic, flammable, and/or corrosive.

Solvents volatility and solubility have contributed to air, water and land pollution, have increased the risk of worker exposure, and have led to serious accidents.

Recovery and reuse, when possible, is often associated with energy-intensive distillation and sometimes cross contamination. In an effort to address all those shortcomings, chemists have started to search for safer solutions.

Safer Solvents and Auxiliaries

Image: Adobe Stock

Page 29: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Problematic organic solvents

No Solvent Supercritical fluids

Water solvent Ionic liquids

Avoidance

Environmentally

benign and safe

Easily separable, safe

Zero

Volatility

Greener alternatives

Safer Solvents and Auxiliaries

Page 30: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Case study: Coffee decaffeination

Conventional method of coffee decaffeination:

• Coffee decaffeination was performed in a chlorinated organic solvent, dichloromethane (DCM), exposure to which can lead to headaches, mental confusion, nausea, vomiting, dizziness andfatigue.

• Coffee beans were heated with steam and then exposed to DCM for decaffeination.

Image: Wikimedia Commons, Coffee Mechanical Separator, Aquapulp

Safer Solvents and Auxiliaries

Page 31: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

• Soaking green coffee beans in water doubles their size, allowing the caffeine to dissolve into water inside the bean.

• Caffeine removal occurs in an extraction vessel (70 feet high,10 feet in diameter), suffused with carbon dioxide at roughly 90 °C and 250 atm. Caffeine diffuses into this scCO2. The beans enter at the top of the chamber and move toward the bottom over 5 hours.

• Decaffeinated beans at the bottom of the vessel are removed, dried and roasted.

• Recovery of dissolved caffeine occurs in an absorption chamber. A shower of water droplets leaches the caffeine out of the supercritical carbon dioxide. The caffeine in this aqueous extract is then often sold to soft-drink manufacturers and drug companies. The purified carbon dioxide is recirculated for further use.

Alternative method for coffee decaffeination:

Zosel, K. Practical Applications of Material Separation with Supercritical Gases. Angew. Chem., Int. Ed. 1978, 17, 702-709

Safer Solvents and Auxiliaries

Case study: Coffee decaffeination

Page 32: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

• Delicate biomedical materials such as vaccines and tissues are conventionally sterilized with ethylene oxide - a carcinogenic, mutagenic, toxic, and flammable gas - or with gamma radiation, which is lethal to all cells.

• Both methods damage the materials they are sterilizing.

• Ethylene oxide persists in tissue.

Case study: Medical sterilization

Conventional medical sterilization:

Image: Svetlana Pohovey, 359th Medical Group, U.S. Air Force photo/Staff Sgt. Kevin Iinuma

Safer Solvents and Auxiliaries

Page 33: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

• Development of a supercritical carbon dioxide (scCO2) based method for sterilization of biological material.

• NovaSterilis sterilization uses scCO2, peracetic acid, and small amounts of water at low temperatures and modest pressure to achieve rapid sterilization of sensitive biomaterials.

NovaSterilis Inc.

Alternative medical sterilization:

Safer Solvents and Auxiliaries

Case study: Medical sterilization

Page 34: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Case study: Replacing dichloromethane (DCM) in chromatography

Amgen’s Green Solvents for Chromatography in practice. If a compound suitably elutes in 5% DCM–MeOH, the bar chart predicts that 60% 3 : 1 EtOAc : EtOH in heptanes or 40% i-PrOH in heptanes would be a suitable starting point to evaluate greener solvent alternatives.

Amgen developed a guide to replace DCM with greener alternatives. DCM is known to be associated with respiratory and cardiovascular toxicity in humans, carcinogenicity, and genotoxicity.

The guide on the right compares the eluting power of different greener solvent mixtures with reference to DCM-Methanol.

Safer Solvents and Auxiliaries

Page 35: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Zoloft® is an anti-depressant and was once one of the best selling pharmaceuticals on the market.

Conventional sertraline synthesis:

• Synthesis was a three step process.

• Used 4 hazardous solvents (methylene chloride, tetrahydrofuran, toluene, and hexane).

Zoloft®

Case study: Manufacturing process for sertraline, the active ingredient in the popular drug Zoloft®

Safer Solvents and Auxiliaries

Page 36: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

• The process was streamlined to a single step that is carried out in ethanol, a much less toxic solvent.

• The new process is also catalytic, cutting down on starting materials by 60%, 45%, and 20% for the three components of the reaction.

• The combined steps eliminated 310,000 pounds of titanium tetrachloride, 220,000 pounds of 50% sodium hydroxide, 330,000 pounds of 35% hydrochloric acid waste, and 970,000 pounds of solid titanium dioxide waste per year.

Pfizer, Inc

Alternative sertraline synthesis:

Image: Wikimedia Commons, Author: Ragesoss

Safer Solvents and Auxiliaries

Case study: Manufacturing process for sertraline, the active ingredient in the popular drug Zoloft®

Page 37: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Topics

• Introduction and Principles [Lectures 1-3]

• Chemistry Intro [Lectures 4-7]• Molecules, drawing, nomenclature, stoichiometry and reactions, metrics

• Sustainability and Life Cycle assessment [Lectures 9-10]

• Renewable feedstocks [Lecture 12]

• Designing for recycling & degradation [Lecture 14]

• Catalysis, Solvents [Lectures 15-17]

• Energy [Lecture 19]

• Green Analytical Chemistry [Lecture 20]

• Intro to toxicology, chemical exposure and dose, molecular toxicology [Lectures 21-23]

• Designing future products with reduced toxicity [Lectures 24-26]

• Real-world case studies [Lecture 13]

Page 38: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

DescriptionOverview of lecture contents

Prior to Lecture

Readings

Lesson Plan Contents

Videos

Page 39: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Topics to Cover in LectureDetailed topic list within lecture materials

• Molecular Weight• What is it and how to calculate MW of

molecules/compounds.• Avogadro’s Number

• Why it’s important.• Explain to students its importance for

stoichiometry and other applications.• Molar Mass

• What is it?• Its applications in conversions.• Ensure students are comfortable with

the topic since it will be required for more detailed calculations.

Page 40: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Topics to Cover in LectureDetailed topic list within lecture materials

• Balancing Equations• Stoichiometry and Calculations• Reactions

• Addition, elimination, replacement, and combustion.

• Examples of organic named reactions.• Lab vs. Nature

• Explain how nature performs chemistry too. Discuss the ways nature performs chemistry and how Green Chemistry is striving to imitate nature.

• Green Chemistry Perspective• Discuss how Green Chemistry is changing

the way reactions are performed.• Solvents, reagents, novel reactors.• Biomimicry.

Page 41: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Class Exercise (optional)Detailed topic list within lecture materials

• Beyond Benign Reactions Lab• https://www.beyondbenign.org/lessons/reactions

-lab/

• Biomimicry Matching Game• https://www.beyondbenign.org/lessons/introducti

on-green-chemistry-biomimicry/

• Stoichiometry Challenge• https://www.beyondbenign.org/lessons/stoichiom

etry-challenge/

Page 42: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Class Exercise (optional)Detailed topic list within lecture materials

• Beyond Benign Reactions Lab• https://www.beyondbenign.org/lessons/reactions

-lab/

• Biomimicry Matching Game• https://www.beyondbenign.org/lessons/introducti

on-green-chemistry-biomimicry/

• Stoichiometry Challenge• https://www.beyondbenign.org/lessons/stoichiom

etry-challenge/

Page 43: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Class Exercise (optional)Detailed topic list within lecture materials

• Beyond Benign Reactions Lab• https://www.beyondbenign.org/lessons/reactions

-lab/

• Biomimicry Matching Game• https://www.beyondbenign.org/lessons/introducti

on-green-chemistry-biomimicry/

• Stoichiometry Challenge• https://www.beyondbenign.org/lessons/stoichiom

etry-challenge/

Supplementary MaterialsLab based activities demonstrating concepts

Page 44: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Center For Green Chemistry and Green Engineering at Yale

Stoichiometry and Reactions

Lecture #6

Date:

Course #

Page 45: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Outline

• Stoichiometry & Calculations

• Reactions

• Important Named Reactions

• Lab vs. Nature

• Green Chemistry in Perspective• Reagents, solvents, and reactors

• Biomimicry

Page 46: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Molar Mass

What is the mass in grams of 1 molecule of sucrose?

1 mol sucrose = 342.30 g sucrose

1 mol sucrose = 6.022 x 1023 molecules of sucrose

x1 mol sucrose

6.022 x 1023 molecules of sucrose342.30 g sucrose

1 mol sucrose

= 5.68 x 10-22 g/molecule

Avogadro'sNumber

Page 47: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

“1 mole of formaldehyde gas reacts with 1 mole of oxygen gas to form 1 mole of liquid water and 1 mole of carbon dioxide gas.”

What is implied…

“30 g H2CO reacts with 32 g O2 to form 18 g H2O and 44 g CO2”

H2CO (g) + O2 (g) H2O (l) + CO2 (g)

Writing and Balancing Equations

Page 48: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Stoichiometry of Chemical Reactions

You can use dimensional analysis…

Just like 1000 g = 1 kg

An amount of 6.48 mole of NH3 reacts with how many moles of O2?

5 mol O2 = 4 mol NH3

6.48 mol NH3 X 5 mol O2

4 mol NH3

= 8.10 mol O2

4 NH3 + 5 O2 4 NO + 6 H2O

Page 49: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Types of Reactions (Cont’d)

Elimination: Taking part of a molecule out• A ---> B + C or more

• Dehydrogenation

• Dehydroxylation

• Dehalogenation

O2 (not shown) was used as a reagent to abstract the –H’s from methanol, the reactant

Page 50: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Nature vs. Lab

Image Sources: Wikipedia Commons, Flickr, Pixabay

Page 51: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Nature vs. Lab

• Chemical transformations happen at ambient temperatures

• Minimal waste• Utilize water as a solvent

and reagent• Complex molecules

seamlessly • Domino and Cascade

reactions• Enzymes• High selectively

• Chemical transformations happen high temperatures and high pressure

• Varying amount of waste produced

• Utilize petroleum-based solvents

• Complex molecules take skills specialized catalysts

• Step-be-step synthesis• Precious metal catalysts• Moderate selectivity

Page 52: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Designing an Ideal Green Reaction

1. Generate no waste or by-product/Use waste sources• Always addition reaction? No.• Must consider the whole picture.

2. High yield and high rate

3. Earth abundant feedstock and catalyst

4. Energy efficient• Does not require high external energy input.• UV light driven.• Microwave assisted.

5. No solvent or environmentally benign solvent• Water• Recyclable organic solvent• scCO2

Page 53: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Biomimicry

Biomimicry is the science and art of emulating nature's best biological ideas to solve human problems.

Bios = lifeMimic = to copy or emulate

Page 54: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

“Pond scum may be a synonym for ‘primitive’, but the tiny organisms that compose it easily beat the human state of the art when it comes to capturing energy from the sun. Some purple bacteria answering to that unflattering description use light energy with almost 95% efficiency – more than four times that of the best man-made solar cells.”

- University of Southern California news release, August 22, 1994

Images: WikiCommons

Still More to Be Learned

Page 55: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Topics

• Introduction and Principles [Lectures 1-3]

• Chemistry Intro [Lectures 4-7]• Molecules, drawing, nomenclature, stoichiometry and reactions, metrics

• Sustainability and Life Cycle assessment [Lectures 9-10]

• Renewable feedstocks [Lecture 12]

• Designing for recycling & degradation [Lecture 14]

• Catalysis, Solvents [Lectures 15-17]

• Energy [Lecture 19]

• Green Analytical Chemistry [Lecture 20]

• Intro to toxicology, chemical exposure and dose, molecular toxicology [Lectures 21-23]

• Designing future products with reduced toxicity [Lectures 24-26]

• Real-world case studies [Lecture 13]

Page 56: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Center For Green Chemistry and Green Engineering at Yale

CatalysisDesigning future catalysts to be more benign

Lecture #15

Date:

Course #

Page 57: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Outline

• What is Catalysis?

• Why its important and improves performance

• Categories of Catalysis

• Homogeneous vs. Heterogeneous

• Greener Alternatives for Catalysis

• Current Trends for the Next Generation of Catalysts

• Additional applications for catalysts

Page 58: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

UNIDO Catalysis Video

https://www.youtube.com/watch?time_continue=3&v=p2_A3EBmawg

Page 59: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Learning Objectives

Explain why the incorporation of catalysts is key to Green Chemistry

Understand the difference between homogeneous, heterogeneous, and biocatalysis

Describe three examples of greener alternatives which use biphasic systems, biocatalysis, or photocatalysis

Page 60: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Catalysis Reaction Diagram

https://commons.wikimedia.org/wiki/File:Catalysis-_Reaction_progress.png

In general it’s more effective, safer, and sustainable to use catalysts than not!

Lowered activation energy!

Page 61: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Homogeneous vs. Heterogeneous

• Difficult separation

• Difficult to regenerate

• Expensive

• High reaction rates

• Less sensitive

• High selectivity

• Known mechanisms

Homogeneous Heterogeneous

• Easy separation

• Easy regeneration

• Cheap

• Lower rates

• Sensitive to more

• Lower selectivity

• Requires more energy

• Unique mechanisms

Page 62: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Designing a Green Catalyst

• Low toxicity

• Earth abundance

• Efficiency

- Rate and energy input

• Compatible with green solvent

• Longevity and Recyclability

• Ease of production

- Large volume and consistent in quality

• High selectivity for desired product(s)

http://www.rsc.org/chemistryworld/Issues/2011/January/CriticalThinking.asp

Not all catalysts are created equal. Chemists need to consider various factors when deciding on the catalyst.

Many metals which are used as catalysts are depleting

Page 63: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Topics

• Introduction and Principles [Lectures 1-3]

• Chemistry Intro [Lectures 4-7]• Molecules, drawing, nomenclature, stoichiometry and reactions, metrics

• Sustainability and Life Cycle assessment [Lectures 9-10]

• Renewable feedstocks [Lecture 12]

• Designing for recycling & degradation [Lecture 14]

• Catalysis, Solvents [Lectures 15-17]

• Energy [Lecture 19]

• Green Analytical Chemistry [Lecture 20]

• Intro to toxicology, chemical exposure and dose, molecular toxicology [Lectures 21-23]

• Designing future products with reduced toxicity [Lectures 24-26]

• Real-world case studies [Lecture 13]

Page 64: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Center For Green Chemistry and Green Engineering at Yale

Green Analytical Chemistry

Lecture #20

Date:

Course #

Page 65: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Outline

• What is Green Analytical Chemistry?

• Analytical Method Assessment

• Tools and Techniques for Assessing Greenness of Analytical Methods

• Sample Preparation

• Analytical Techniques and Methods

• Chromatography

• Spectroscopy

• Mass spectrometry

• Process Analytical Technology (PAT)

Page 66: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Green Analytical Chemistry

Sample Prep

• Solvent selection/use

• Green media and/or reagents

• Extraction/separation processes

• Reduction of scale

Instrumental Analysis

• Techniques:

• Chromatography

• Spectroscopy

• Etc.

• Method improvement

Real-time Analysis/PAT

• At-line

• On-line

• In-line

iStock photos: Standard license

“Green Analytical Chemistry” by Paul Ferguson and Douglas Raynie, in Green Techniques for Organic Synthesis and Medicinal Chemistry, 2nd Edition, Zhang, W. and Cue, B. W., Eds., Wiley, 2018, pp. 43-66

Page 67: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Topics

• Introduction and Principles [Lectures 1-3]

• Chemistry Intro [Lectures 4-7]• Molecules, drawing, nomenclature, stoichiometry and reactions, metrics

• Sustainability and Life Cycle assessment [Lectures 9-10]

• Renewable feedstocks [Lecture 12]

• Designing for recycling & degradation [Lecture 14]

• Catalysis, Solvents [Lectures 15-17]

• Energy [Lecture 19]

• Green Analytical Chemistry [Lecture 20]

• Intro to toxicology, chemical exposure and dose, molecular toxicology [Lectures 21-23]

• Designing future products with reduced toxicity [Lectures 24-26]

• Real-world case studies [Lecture 13]

Page 68: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Center For Green Chemistry and Green Engineering at Yale

Real-World Cases in Green Chemistry

Lecture # 13

Date:

Course #

Page 69: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Outline

• What are the Presidential Green Chemistry Challenge Awards?• Award Categories

• PGCCA Case Studies: • 2016: Newlight Technologies, AirCarbon: Greenhouse Gas Transformed into High-

Performance Thermoplastic• 2012: Buckman International, Inc.: Enzymes Reduce the Energy and Wood Fiber Required to

Manufacture High-Quality Paper and Paperboard• 2011: Professor Bruce H. Lipshutz, Towards Ending Our Dependence on Organic Solvents• 2008: SiGNa Chemistry, Inc.: New Stabilized Alkali Metals for Safer, Sustainable Syntheses• 2005: Archer Daniels Midland and Novozymes, NovaLipidTM: Low Trans Fats and Oils

Produced by Enzymatic Interesterification of Vegetable Oils Using Lipozyme®• 2002: Pfizer re-design of Sertraline (ZOLOFT®)• 1996: Dow Chemical Company Designing an Environmentally Safe Marine Antifoulant

Page 70: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Center For Green Chemistry and Green Engineering at Yale

Professor Bruce Lipshutz, University of California, Santa Barbara

Towards Ending our Dependence on Organic Solvents

2011 Presidential Green Chemistry Challenge Academic Award

Page 71: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Professor Bruce Lipshutz, University of California Santa Barbara Towards Ending Our Dependence on Organic Solvents

Most chemical manufacturing processes rely on organic solvents, which tend to be volatile, toxic, and flammable. Chemical manufacturers use billions of pounds of organic solvents each year, much of which becomes waste. Water itself cannot replace organic solvents as the medium for chemical reactions because many chemicals do not dissolve and do not react in water.

Professor Lipshutz has designed a safe surfactant that forms tiny droplets in water. Organic chemicals dissolve in these droplets and react efficiently, allowing water to replace organic solvents.

reactions take place here

Images curtesy of Professor Bruce Lipshutz

Page 72: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Professor Bruce Lipshutz, University of California Santa Barbara Towards Ending Our Dependence on Organic Solvents

New Nanomicelles as “Nanoreactors” in Water

Benign by design “designer” surfactants (available from Aldrich)

Images curtesy of Professor Bruce Lipshutz

Page 73: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Professor Bruce Lipshutz, University of California Santa Barbara Towards Ending Our Dependence on Organic Solvents

Applications of nanomicellar technologychemistry in water at RT

Images curtesy of Professor Bruce Lipshutz

Page 74: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

What is a micelle?

Micelle

Hydrophilic

Hydrophobic

Page 75: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Topics

• Introduction and Principles [Lectures 1-3]

• Chemistry Intro [Lectures 4-7]• Molecules, drawing, nomenclature, stoichiometry and reactions, metrics

• Sustainability and Life Cycle assessment [Lectures 9-10]

• Renewable feedstocks [Lecture 12]

• Designing for recycling & degradation [Lecture 14]

• Catalysis, Solvents [Lectures 15-17]

• Energy [Lecture 19]

• Green Analytical Chemistry [Lecture 20]

• Intro to toxicology, chemical exposure and dose, molecular toxicology [Lectures 21-23]

• Designing future products with reduced toxicity [Lectures 24-26]

• Real-world case studies [Lecture 13]

Lectures #8 and #18 In-class Exams!

Final Exam!

6 Homeworks!

Page 76: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

1. Molecules and Nomenclature

2. Stoichiometry and Reactions

3. Estimating Biodegradation of Organic Molecules

4. Solvent Substitution: CHEM21 Solvent Selection Guide

5. Chemical Exposure and Dose

6. Toxicology

Includes answer keys

Homeworks

Page 77: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

Exams

• Exam 1• 41 questions w/answer key

• Exam 2• 54 questions w/answer key

• Final Exam• 95 questions w/answer key

• Note to instructor: Below is a list of questions that are suitable for a exam. You may select any number of question that you may feel is best suited for your class. This serves a mere guide and any additional questions are welcome.

Page 78: Green Chemistry University Curriculum Webinar

Center For Green Chemistry and Green Engineering at Yale

How to use the course materials?

Intro to GC course

Supplement with a

Module

HW’s and Exams

Supplemental Resources

Introduce a Case Study

Page 79: Green Chemistry University Curriculum Webinar

Welcome to the Green Chemistry Commitment

Green Chemistry Education Webinar Series

Recording and supporting documents will be available:

https://www.beyondbenign.org/he-webinars/

Submit questions at any time during the webinar in the

Control/Chat box on the Control Panel

Natalie O’Neil, Ph.D.Program Manager

Higher Education

Beyond Benign

@natjoneil

Kimberly Chapman, B.A.Administrative Assistant

Center for Green Chemistry and

Green Engineering at Yale

Page 80: Green Chemistry University Curriculum Webinar

Join us for our next webinar!

Recordings, supporting documents and upcoming webinars (with registration links):

http://www.beyondbenign.org/he-webinars/

Sign-up for Beyond Benign’s quarterly newsletter and webinar announcements on our homepage:

www.beyondbenign.org

Sign-up for CGCGE Yale’s monthly newsletter:

https://mailchi.mp/4d1c7d89c531/greenchemistry

Thank you for joining us!

“ACS GCI Pharmaceutical RoundTable Tools Webinar”

November 20, 2019 @ 2:00 pm - 3:00 pm