Innovation in Next Generation Environmental Technologies: Benefits and Barriers

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Innovation in Next Generation Environmental
Technologies Benefits and Barriers
Center for Environmentally Responsible Solvents
and Processes Innovation Process Seminar
Series February 19, 2004
Parry M. Norling Visiting Fellow Chemical
Heritage Foundation Parry.norling_at_comcast.net
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Wall St. Journal-1992
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Wall St. Journal Front Page

• despite spending of more than 13 billion on
  chemical and related research over the past 10
  years, DuPonts 5,000 scientists and engineers
  were a technological black hole

4
More

• They sucked in money but, Company officials
  concede, didnt turn out a single all new
  blockbuster or even many innovations.
• The technology is great, but wheres the payoff?

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Another Nylon or Teflon (R)?
1938 Nylon, Teflon and Butacite
1940
1935 Better things for better living... through
chemistry
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Success Rate New Products
125 beginning projects .8
300 submitted ideas .3
3000 raw ideas .03
1.7 launches 60
9 Large developments 11
4 major developments 25
1 commercial success
Stevens and Burley Research-Technology Management
May-June 1997
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Innovation Not a Linear Process
Technology developments
Changes in the external environment
Market knowledge
Company strategies
Knowledge of customer needs
Scientific advances
IDEAS
OPPORTUNITY IDENTIFICATION
MARKET PENETRATION AND DEVELOPMENT
CONCEPT/ TECHNOLOGY DEVELOPMENT
SCREENING AND BUSINESS ANALYSIS
DEVELOPMENT AND COMMERCIALIZATION
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Innovation Not a Linear Process
Technology developments
Technology Intelligence
Changes in the external environment
Market knowledge
Company strategies
Knowledge of customer needs
Scientific advances
IDEAS
OPPORTUNITY IDENTIFICATION
MARKET PENETRATION AND DEVELOPMENT
CONCEPT/ TECHNOLOGY DEVELOPMENT
Technology Valuation and Creation of Benefits
SCREENING AND BUSINESS ANALYSIS
DEVELOPMENT AND COMMERCIALIZATION
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Innovation Not a Linear Process
Technology developments
Creativity Idea Generation Breakthroughs
Changes in the external environment
Market knowledge
Company strategies
Knowledge of customer needs
Scientific advances
IDEAS
Quality of the research
OPPORTUNITY IDENTIFICATION
MARKET PENETRATION AND DEVELOPMENT
CONCEPT/ TECHNOLOGY DEVELOPMENT
Knowledge Management important throughout the
entire process- critical in the recycle loops
SCREENING AND BUSINESS ANALYSIS
DEVELOPMENT AND COMMERCIALIZATION
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Some Successes
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Kevlar and Surlyn
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Development
Both started with a defined need
Surprising lab discovery YES YES Making the
discovery practical YES Developing a
manufacturing process YES DIFFICULT Overcoming
the process hurdles YES DIFFICULT Overcoming
the financial hurdles YES SOME Finding the
markets -- applications DIFFICULT EVOLVING Facing
the unexpected YES Facing death YES Makin
g it a success YES YES
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Kevlar The real story
A spacecraft that crashed 50 years ago contained
fibers that even razors could not cut through
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Discovery of Lyotropic Liquid Crystallinity
1965

• Stephanie Kwolek discovery processable high
  molecular weight para-aromatic polyamides
• Discovered that concentrated liquid crystalline
  solutions of such polymers could be spun from
  tetramethylurea

O
H
C
N
n
poly(benzamide)
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1,4B Not the Right Polymer!

• Difficult to purify
• Low concentrations
• Borderline fiber properties
• Superior product from paraphenylene diamine and
  terephthalic acid (PPD-T)?

Herbert Blades, Paul Morgan, Stephanie Kwolek,
John Griffing, Eugene Magat
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A major breakthrough by Herb Blades -- 1969

• Tried 100 sulfuric acid as spin solvent -- 10
  PPD-T -- little improvement in properties over
  1,4B
• Surprise poly(PPD-T) and sulfuric acid form a
  complex melting at 80 degrees C. which is stable
  at higher temperatures
• Used an air gap before coagulation

Morgan,Blades,Kwolek
Gave birth to Kevlar
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Strong Fibers from Liquid Crystals
H
N
O
C
C
N
O
n
H
Quench and remove solvent
Draw liquid Xtals into oriented fiber
Lyotropic solution
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Creating the Ultimate Fiber

• Traditional synthetic fibers get strength from
  drawing to align the polymer molecules
• Alignment is limited by molecular entanglement
• Kevlar fiber strength comes from aligning the
  molecules before forming the fiber
• Lyotropic crystals are oriented by liquid shear
  in the fiber forming process
• Rigid molecular chain is key to creating the
  Lyotropic phase
• Fiber is quenched to hold molecular orientation

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Scale-up

• Dealing with sulfuric acid
• Disposal of the spinning solution very pure
  gypsum (7 pounds for every pound of fiber)

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Scale-up a major surprise!

• Toxicity of the polymerization solvent
  Hexamethylphosphoramide 40 man-years of
  technical effort

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Demonstrate the market potential of Kevlar
Fortune Magazine Kevlar was a miracle in
search of a market

• Must justify 400MM investment
• Systems Engineering to develop the
  opportunities Ropes and cables, Aircraft
  composites
• Tire reinforcement a bust
• Considerable application development!!!!!!!!!!!!!!
  
• Commercialized in 1971
• By 1975 only 10 market segments -- 50
  applications
• Today -- more than 200 applications

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Kevlar - A Reality
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The Surlyn Story
Creation of the first ionomer
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Initial History
A tough transparent crystal clear polymer!

• Early 1960s Development of ethylene copolymers
  with functionality
• Desire to crosslink these polymers
• Preparation of sodium salt of ethylene/methacrylic
  acid copolymers -- as a control experiment

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Interchain ionic bonds create

• melt strength
• solid state toughness
• resistance to oils

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A customer?
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Late 1960s Time of Crisis

• Too many possible products- low sales
• Complex manufacturing process
• Market development was tough
• Product was losing money

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Surlyn on Golf Balls?
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Recognition
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More and more applications
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Three lessons

• Technology driven research switched eventually to
  market driven research
• Properties that customers came to value were
  quite different from what was first expected
• Dedication, commitment, and patience by many
  unique individuals allowed the product to survive

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Conclusions

• Technology was cleverly developed (good science)
• Developing the technology was not at all easy
• Technology initially sought markets
• Markets found unappreciated properties or needed
  much help in applying the technology
• Individuals exerted themselves to keep the
  products alive
• Surlyn and Kevlar are now premier products

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Failures
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Packaging Products Important Market

• Mylar PET film
• Surlyn Ionomer resins
• Bynel adhesives
• Clysar shrink wrap
• Elvax resins
• Nucrel acid copolymers
• PET bottle royalties
• nylon films and resins

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Growing packaging market

• Opportunitypolymer replacement for rigid
  packaging (glass and metal)-- strategic
• Need good oxygen and gas barrier properties
• Several candidates
• PVDC
• PET
• metalized plastics
• ethylene-vinyl alcohol polymer (EVOH) multilayer
  package

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EVOH is the Target

• Related to two DuPont Products Ethylene/vinyl
  acetate polymers and polyvinylalcohol
• Multilayer extrusion technology now available

ethylene vinyl acetate Elvax vinyl
resins
vinyl acetate polyvinyl acetate
Elvanol polyvinyl alcohol
Polyethylene or polypropylene, adhesive, EVOH,
adhesive, polyethylene or polypropylene
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But

• Kuraray and Nippon Gohsei have plants in Japan
• Kuraray forming joint venture (Evalca) to
  manufacture in United States
• Critical process patents held by the Japanese
• No competitive advantage

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Strategy

• Get to the market fast -- before Evalcas plant
  is on stream keep Nippon Gohsei from building
  more capacity
• Get competitive advantage in product or process
  innovation

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Issues

• Joint venture? Kuraray - no, Nippon Gohsei a
  possibility
• How to make developmental quantities to get into
  the market rapidly?
• 20MM for pilot plant?

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More Issues

• How to forecast a competitive advantage when your
  are me-too?
• How to develop a favorable economic case?

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Some decisions

• No Joint venture
• Develop batch semiworks to supply product for
  market development - not thorough basic data
• Seek breakthroughs in both process and product --
  prudent risk, process simplification, process
  modification to get product advantage.

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More Decisions

• Full speed ahead even though venture manager and
  business say it is not justified
• Commit to cutting 20 off investment
• Commit to making breakthroughs
• Commit to favorable market forecasts

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EVOH Process
Low pressure polymerization
E
Stripper
alcoholysis
VAc
VAc
precipitation
grinding
drying
extrusion
additives
EVOH for sale
four steps with new technology
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Piloting

• Semiworks as batch with no integration -- product
  from one step taken to the next
• Polymerization ran for 2 years, terminated during
  detailed engineering
• Stripping and alcoholysis 1300 scale
• Precipitation 1500 scale
• Reliance on process simulation

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Results

• 18 months to start up
• Could not get rate
• Could not get quality (color, gel...)
• Questions on operability
• Could not justify 30MM to make needed changes
• Nippon Gohsei now has the plant

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Today
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Some common lessons

• Compounding risks -- what is a prudent risk?
• Extent of piloting
• Resources
• Thorough understanding of the realistic business
  case
• When to go after the breakthrough technologies?
• Managing expectations

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Next Generation Environmental Technologies
Benefits and Barriers MR 1682-OSTP

Parry Norling, Robert Lempert, Susan Resetar,
Chris Pernin, and Sergej Mahnovski

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Innovation Not a Linear Process
Technology developments
Most examples taken here
Changes in the external environment
Market knowledge
Company strategies
Knowledge of customer needs
Scientific advances
IDEAS
OPPORTUNITY IDENTIFICATION
MARKET PENETRATION AND DEVELOPMENT
CONCEPT/ TECHNOLOGY DEVELOPMENT
SCREENING AND BUSINESS ANALYSIS
DEVELOPMENT AND COMMERCIALIZATION
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Benefits from NGETs

• Environmental Reduction in
• Toxics (TRI) (toxicity weighted index)
• Carcinogens- (specific chemicals removed from
  environment)
• Endocrine Disrupters- (Specific chemicals
  removed)
• Persistent materials- (quantity of specific
  chemicals)
• Greenhouse gases- (CO2, Nitrous oxide, methane,)
• Total waste generated- (total pounds), reduction
  of resources
• Damage to the eco-system- (specific materials)

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Benefits from NGETs

• Security
• Critical materials
• Quantities of stored hazardous materials
  terrorist targets
• Less energy energy efficiency
• Worker safety
• Performance/economics
• Quality, improved product performance
• New green markets
• Reduced manufacturing costs
• Reduced regulatory compliance costs

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Case studies

• Description of the chemistry and/or science and
  technology involved. Principles? Why can this be
  done now but not before?
• Sectors affected now and in the future
• Immediate benefits
• Long-range benefits

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Case studies

• Development/commercialization history What firms
  are currently developing and commercializing this
  technology? For what purpose? How successful?
• Incentives to adopt Were firms responding to
  existing or expected regulations? Did they see a
  competitive advantage? Any customer pressures? Is
  the technology proprietary?
• Barriers to adoption What have been the chief
  barriers holding back commercialization?
• Government role What has been the government
  role to date in the development and
  commercialization

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Case studies

• 1. Use of supercritical or liquid CO2 as solvent
• Surfactants enabling use of supercritical CO2 as
  solvent in dry cleaning and precision cleaning
  (chip manufacture)
• Production of fluoropolymers
• Decaffeination of coffee
• 2. A three step process replaced a six step
  process for manufacture of ibuprofen
• 3.Converting polymers to monomers for recycle
  PET and Nylon

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Bio-based processes

• Use of renewable feedstocks (biomass) in
  conventional chemical processes
• Fermentation using immobilized or free cells with
  renewable feedstocks involving a number of
  stepwise reactions
• Use of enzymes as biocatalysts single reaction
• Use of animals or green plants to process
  renewable feedstocks

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Case studies

• 4. Bio-based processes 47 including
• Use of genetically altered Echerichia coli to
  produce adipic acid, Catechol, and substitute for
  BHT
• 1,3 propanediol from glucose, polyester
  intermediate
• biopulping
• Enzymatic Production of acrylamide from
  acrylonitrile
• Production of Vitamin B-2
• Biocatalytic Production of 5-Cyanovaleramide.
• Removal of metals from mine water by biotreatment
• Conversion of waste biomass to animal feed,
  chemicals and fuels

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Substitution of Green Chemistry
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10
Take over time
5.0
?
f(new) f(old)
2.0
1.0
5
.2
.1
Fisher-Pry Technology adoption model
.05
.02
.01
2000 2010 2020 2030 2040 2040 2050 2060 2070
2080 2090
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Substitution of Bio-based Processes
Bio-based processes- substitution in industry
sectors (fraction of processes that gave
environmental benefits)
20
Pulp paper (100)
10
5.0
f(new) f(old)
2.0
Pharma/fine chemicals (50-75)
1.0
5
.2
.1
.05
Commodity chemicals (75-100)
.02
.01
2000 2010 2020 2030 2040 2040 2050 2060 2070
2080 2090
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Case studies

• 5. Pulp and paper processes
• Delignification and bleaching of pulp in paper
  manufacture without the use of chlorine or
  chlorine dioxide
• 6. Room temperature ionic liquids
• 7. Dimethyl carbonate
• 8. Process for Production of Cytovene potent
  antiviral agent
• 9. Production of Hydrogen Peroxide directly from
  Hydrogen and Oxygen in CO2
• 10. Advanced oil and gas exploration and
  production technologies
• 11. Various approaches to water purification
• 12. Capture of nitrous oxide in adipic acid
  manufacture to use in new phenol process

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Case studies

13. Wood Preservation 14. Production of
polyaspartic acid (PAA) 15. Sentricon Termite
Colony Elimination System 16. Inert anodes in
aluminum smelting 17.High yield melting of
aluminum 18. Elimination of Ozone-Depleting
Chemicals in the Printed Wire Board and
Electronic Assembly and Test Processes
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Surmounting Barriers

• Many barriers
• Success will require overcoming a number of
  barriers for NGETs

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Technical barriers

• Production of hydrogen peroxide directly from
  hydrogen and oxygen
• Biobased process for adipic acid
• Inert Anodes in Aluminum smelting
• Dimethyl carbonate
• Biobased process for 1,3 propanediol

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Benefits Inert anodes
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Infrastructure barriers

• Capture of Nitrous oxide from adipic acid
  manufacture to use in new phenol process
• New routes to vinyl acetate and ethyl acetate
• Synthesis of glyphosate

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Reuse of Nitrous Oxide
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Taking advantage of infrastructure needs

• Glyphosate
• Vinyl acetate and ethyl acetate

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Institutional Barriers

• New route to Ibuprofen
• Roundup Ready Soybeans, Corn, Cotton

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Market Barriers
Barriers in the marketplace

• Polylactides
• Supercritical carbon dioxide in dry cleaning
• Recycling PET and nylon to monomers
• TAML catalysts for oxidations with hydrogen
  peroxide
• Converting waste power carbon dioxide into algae
  and then organic feedstocks

Incentives to adopt
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Case studies
Production of polylactides
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Incentives to adopt

• Reluctance of the pulp and paper industry
• Not enough concern over global warming

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Some Conclusions

• Green chemistry-based processes are being
  commercialized at a somewhat increasing rate.
• The primary driving force is cost regulatory
  compliance is most often secondary.
• The benefits can be measured and documented.
• The potential environmental benefits are
  significant.
• .

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Some Conclusions

• But it will take years to reach these benefits at
  the present rate of commercialization.
• A number of actions are needed to overcome the
  barriers much advice from the management
  literature

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Overcoming technical barriers

• Developing the best ideas
• Discovery based planning attacking the critical
  assumptions
• Organizing the resources

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Overcoming infrastructure barriers

• Include issue in the research plan

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Overcoming the Institutional Barriers

• Some lessons from Paul Light
• Researchers must influence policy-makers

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Overcoming the Market Barriers

• Crossing the chasm
• Technology and Market Intelligence
• Knowing where you are on the Familiarity Matrix
• Governmental action

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Crossing the Chasm
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Technology or Product
New to world New to firm Familiar
Markets
Suicide square
Familiar New to firm New
to the world
Familiarity Matrix can be used to decide how to
collaborate
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Government Actions Affecting NGETs

• Funding RD
• Purchase/Procurement
• Tax incentives/disincentives
• Subsidies
• Regulations workplace, emissions, products
• Patent Law
• Industry consultations
• Voluntary programs
• Infrastructure support and development
• Education and training

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l
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Managing RD

• Provide a broad commercial base - leverage
  research across diverse business lines.
• Pick your problems with great care and judgment.
• Be patient - dont evaluate results after one
  year, but wait as long as five or six.
• Know when to quit a problem - done largely by
  intuition, but we prefer to call it intelligence.

Crawford Greenewalt 1950
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Additional Slides
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Bio-based processes performance/economics

• Amino acid market a green chemistry market
• Reduced manufacturing costs and reduced
  investment
• Reduced regulatory costs

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Bio-based processes long term benefits
The Committee on biobased Industrial Products of
the National Research Council Evaluation of
the environmental impacts of biobased industries
should be a research priority. These evaluations
should include environmental and energy audits of
the entire product life cycle rather than a
single manufacturing step or environmental
emission. Development of a biobased industry may
produce widespread environmental benefits, but
these implications are not well understood.
Production of agricultural and forest feedstocks
can have positive, negative, or neutral
consequences on wildlife, soil, air, and water
quality, but these effects depend on many
factors, such as previous use of land and crop
management practices. In specific instances
biobased processes are less polluting, and
biobased products are biodegradable. To ensure
that biobased products fulfill their promise of
environmental sustainability, life-cycle
assessments of biobased products should be a
research priority.
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Supercritical carbon dioxide

• Dry cleaning
• Decaffeination
• Polymerization of fluoropolymers

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Benefits of Supercritical Carbon Dioxide
drycleaning

.
Figure 1. Comparison of a Model Facility's
Emissions of PCE. (SCCO2 supercritical carbon
dioxide CA carbon adsorber RC refrigerated
condensor)
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Benefits Carbon Dioxide Decaffeination

• Elimination of methylene chloride

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Benefits carbon dioxide as polymerization solvent

• Elimination of CFCs

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Benefits from other cases

• Dimethyl carbonate
• PET and Nylon recycle

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Benefits from other cases

• Wood preservation
• Ibuprofen
• Hydrogen peroxide
• Sentricon

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Management Tools and Techniques Through the
Years
3rd/4th Generation Management.....
Learning Organization Knowledge Mgt.
Cycle-time Reduction
Empowerment
EVA
Pay-for-performance
Missions Visions
Portfolio Management
Excellence
Experience Curves
Core competencies
Disintermediation
COTs
Matrix Mgt.
Pecos River
Benchmarking
ROI
Org. Effectiveness
TQM
Platforms
Cost of Govt reg.
MBWA
Business Process Reengineering
MBO
Managerial grid
MBX
Intrapreneuring
HPWS
Theory X-Y
Balanced Scorecard
Theory Z
1960
1970
1980
1990
2000
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Benefits bio-based processes elimination of
toxics

• Intermediate for cephalosporin antibiotics
• N,N-dimethylaniline, trimethylchlorosilane,
  phosphorous pentachloride, methylene chloride,
  zinc salts
• Bioleaching and minerals bioxidation
• arsenic oxide, sulfur dioxide
• Metals bioremediation and recovery
• contaminated gypsum

95
Benefits bio-based processes elimination of
toxics

• Intermediate for cephalosporin antibiotics
• N,N-dimethylaniline, trimethylchlorosilane,
  phosphorous pentachloride, methylene chloride,
  zinc salts
• Bioleaching and minerals bioxidation
• arsenic oxide, sulfur dioxide
• Metals bioremediation and recovery
• contaminated gypsum

96
Bio-based processes elimination of carcinogens,
persistent materials

• Pulp bleaching with enzymes 16 reduction in
  carcinogens and 12 reduction in heavy metals
• Pulp bleaching in Japan 40 reduction of AOX

97
Bio-based processes- elimination of greenhouse
gas emissions

• Polylactic acid
• Powerhouse carbon dioxide to methane and acetic
  acid

98
Bio-based processes reduction in total waste

• Riboflavin
• air emissions- 50, water-66
• Cephalexin
• air and water-80
• 5-cyanovaleramide
• -126 metric tons of heavy metal catalyst waste

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Table 1. Summary of case studies.
Principles themes
 
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