14 Rubber & Plastics News ● November 1, 2010 ww.rubbernews.com

Technical

BioIsoprene for use in renewable alternativesExecutive summary

Rubber is a critical and strategic industrial raw material for manufacturing awide variety of products, ranging from medical devices and personal protectiveequipment to aircraft tires.

Presently, nearly all major manufacturers of rubber goods are dependent oneither imported natural rubber from Hevea brasiliensis (i.e., the Brazilian rub-ber tree) or petroleum-based synthetic polymers as feedstocks.

Unfortunately, neither material is obtainable from domestic U.S. sources inquantities sufficient to meet anticipated future demand.

In 2008, Goodyear and Genencor, a division of Danisco A/S, announced a pro-gram to co-develop BioIsoprene-brand material as a revolutionary bio-based al-ternative to the petroleum-derived chemical compound isoprene.

BioIsoprene can be used for the production of synthetic elastomers and rub-ber, which in turn are alternatives to natural rubber.

The development of BioIsoprene could make the tire and rubber industry lessdependent on oil-derived products, such as synthetic rubber made from petrole-um-derived isoprene or butadiene.

This paper provides an overview of current efforts to develop BioIsoprene,ranging from the early motivations for developing BioIsoprene to the most re-cent technical accomplishments.

By Frank J. Feher,Goodyear

Marguerite Cervin, Anthony Calabria, Gregg Whited

and Andrei MiasnikovGenencor International Inc.

About 10 million metric tons (20 bil-lion pounds) of natural rubber are pro-duced annually,1 most of which is collect-ed from trees in relatively undevelopedcountries within several hundred milesof the equator.

About half of the global natural rub-ber supply is used to make tires, whichon average contain approximately equalamounts of natural rubber and petrole-um-derived synthetic rubber.

As the economies in Asia have grownrapidly, both demand for natural rubberand its price have increased dramatically.

In fact, the supply and price issues as-

sociated with both natural rubber andpetroleum-derived synthetic rubberhave become eerily similar to those ob-served for oil: supply is inherently limit-ed, demand is growing rapidly, andnearly all of the material must be im-ported from a relatively small number ofcountries with potentially unreliablesupplies.

Industries dependent on inexpensiveimported natural rubber also face threeadditional threats with potentially cata-strophic consequences.

The first is accidental or intentionalintroduction of South American leafblight into the growing region responsi-ble for more than 90 percent of theworld’s rubber supply.

This fungus was a major problem inBrazil’s rubber-growing regions andcould rapidly devastate Asia’s rubbertrees,2 which are all derived from thesame species (Hevea brasiliensis).

The other two threats stem from thefact that most rubber is collected by rel-atively poor people in underdevelopedcountries.

If these countries undergo substantialeconomic development, there might befewer incentives for people to collectrubber and strong incentives to plantmuch more productive crops, such asfood or palm oil for fuel.

If on the other hand these countriesremain underdeveloped and there is aflu pandemic, it seems possible basedon earlier flu pandemics3 that rubber-producing countries might suffer dis-proportionately greater than devel-oped countries and that the naturalrubber supply chain might be greatlydisrupted.

All of these issues seemed to convergein 2006 as the global economies werebooming, oil prices were climbing to-ward $150 a barrel, natural rubberprices were more than $1 per pound,geopolitical tensions were rising, andAsia was struggling to prevent thespread of a flu virus similar to the oneresponsible for killing an estimated 50million to 100 million people in 1918.

It was against this backdrop thatGoodyear launched its most ambitiouseffort since WWII to develop dependablesources of rubber from domestic U.S.feedstocks.

As outlined below, this effort seeks toleverage recent advances in industrialbiotechnology to produce large amountsof synthetic polyisoprene from the

same biorefinery feedstocks being de-veloped for large-scale production ofbiofuels, such as bioethanol, biobutanoland biodiesel.

Approaches for replacing NRDuring and since WWII, research

done to develop alternatives to Heveanatural rubber identified three promis-ing domestic U.S. sources for rubber:

1. Cultivation of rubber from guayulelatex (Parthenium argentatum)4

2. Cultivation of rubber from roots ofthe Russian dandelion (Taraxacum kok-saghyz)5

3. Production of synthetic polymersfrom petroleum-derived monomers,6 es-pecially isoprene, butadiene andstyrene.

The first two sources are noteworthybecause both were: (a) explored exten-sively by the U.S. during the 1940s; (b)shown to be useful for tire applicationswhen Hevea rubber is not available; (c)abandoned in favor of Hevea rubber andsynthetic rubber after WWII; and (d) re-cently reintroduced as modern replace-ments for imported Hevea rubber.

The third approach—synthetic poly-mers from petroleum-derived mono-mers—ultimately prevailed as the mostattractive alternative to Hevea rubberbecause its appeal was irresistible dur-ing the golden age of petrochemical re-search, when U.S. supplies of petroleumwere plentiful and energy was inexpen-sive.

At the time, polymer chemists had lit-tle appreciation for what they didn’tknow about the structure of natural rub-ber7 and they had not yet realized that itwould be extremely difficult (impossi-ble?) to make a true natural rubber re-placement based solely on polymers orcopolymers of hydrocarbon monomers.

Nevertheless, early investments insynthetic polymer research paid big div-idends by providing commercially viableroutes to several large-volume syntheticrubbers that are now widely used in thetire industry, including styrene-butadi-ene rubber and synthetic cis-polyiso-prene (synthetic PI).

Of all of these synthetic rubbers, syn-thetic PI (e.g., Natsyn) has propertiesthat are most similar to natural rubberbecause its chemical composition andstructure are most similar to naturalrubber.7

Unfortunately, the isoprene monomerrequired to make synthetic PI has al-ways been scarce relative to the amount

of natural rubber used in tires, eventhough synthetic PI would be a suitablereplacement for natural rubber formany applications.

More recently, advances in molecularbiochemistry and industrial biotechnolo-gy present two other tantalizing possi-bilities for developing useful materialsto replace Hevea rubber.

The first involves production of naturalrubber via genetically-modified plants ormicro-organisms containing the key rub-ber-producing enzymes found in Heveabrasiliensis.

Although it has be argued that thisapproach would not be economically vi-able for microbial fermentation,8 extrap-olation of Metabolix’s technology9 forproducing high-grade thermoplasticpolyesters in plants clearly suggeststhat it might be possible to produce com-parable particles of cis-PI in geneticallyengineered plants.

The second possibility is to producesynthetic rubber from monomers (e.g.,isoprene, butadiene, styrene) derivedfrom industrial fermentation of the samefeedstocks being considered for fermen-tation-based production of biofuels.

Although, in principle, it should bepossible to develop large-scale replace-ments for Hevea rubber based on all of

Table I. Two known biochemical pathways for producing isoprene.

TECHNICAL NOTEBOOKEdited by Harold Herzlichh

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Technicalthe approaches described above, eachof these approaches presents a num-ber of unique technical and businessrisks.

In the case of guayule, Russian dande-lion and other crop-based approaches,there are many obvious challenges asso-ciated with developing an integratedsupply chain for growing, harvestingand processing large volumes of plant-based feedstocks into finished rubber.

These kinds of challenges require co-ordinated action by a large number ofpeople and agencies, and they are noto-riously difficult to overcome without tru-ly compelling business cases or aggres-sive government support.

The USDA is working with companies(e.g., Yulex Corp.) to lay the foundationfor domestic production of rubber crops,but it still is likely to take many years be-fore large amounts of domestic rubberwould become available for tire produc-tion.

There also are considerable technicalrisks associated with developing Heveareplacements based on rubber-produc-ing crops or micro-organisms.

First and foremost, there are big dif-ferences between natural rubbers de-rived from different sources.7

Are any of these materials suitable asa replacement for Hevea rubber in to-day’s applications? And if the perform-ance of these materials is not on par withHevea rubber, what options are avail-able for closing any performance gaps?

Would it be easy to re-engineer aplant or microorganism to provide moredesirable rubber properties, such as tearstrength or rate of strain crystalliza-tion?

Could this be done quickly and cost-ef-fectively without compromising the moredesirable characteristics of the plant ormicro-organism, especially the rubberyield and the cost to produce rubber?

While it’s true that it never has beeneasier to engineer crops or micro-organ-isms, it is equally true that the demandsplaced on the performance of naturalrubber are much higher than they werein the 1940s and ’50s.

Cost-effectively producing rubberfrom plants or micro-organisms is onlyhalf the battle.

Any large-volume replacement for He-vea rubber must have properties suffi-ciently similar to Hevea rubber to allowits use without compromising perform-ance.

The BioIsoprene optionAs Goodyear was evaluating options

for developing alternatives to importednatural rubber, the U.S. announced itsintention to aggressively fund develop-ment of technology for producingethanol from cellulosic materials.

In fact, the stated U.S. goal was tomake cellulosic ethanol “practical andcompetitive within six years,” or by2012.10

This announcement, which occurredduring President Bush’s 2006 State ofthe Union address, seemed reminiscentof President Kennedy’s earlier challengeto put a man on the moon by the end ofthe 1960s.11

The challenge was Herculean, and thegovernment clearly was willing to spendthe resources necessary to attract andmobilize the talent required to deliversuch an ambitious goal.

As we contemplated the significanceand likely impact of the U.S. effort to ac-celerate commercialization of cellulosicethanol technology, we realized that thefeedstocks being considered for biofuelproduction might be attractive for pro-ducing monomers for synthetic rubber.

In particular, we wondered whether itmight be possible to produce “cellulosicisoprene” via industrial fermentation ofsugars derived from cellulose.

If this was true and bioethanol indeedcould be made inexpensively via indus-trial fermentation, it seemed reasonablethat production of “bioisoprene” alsomight be commercially viable on a scalelarge enough to make enough syntheticpolyisoprene to replace substantialquantities of natural rubber in tires.

Our concept for replacing Hevea rub-ber with synthetic PI derived fromBioIsoprene quickly gained momentumas we examined the known literature.

We already were aware that isopreneis a naturally occurring hydrocarbonproduced by a broad range of plants andanimals,12 so we knew that biochemicalpathways existed for producing it.

We soon learned that there are, infact, two known pathways for producingisoprene: the MVA (i.e., mevalonic acid)pathway13 and the DXP (i.e., deoxy-xylu-lose phosphate) pathway.14 (See TableI) .

Glucose can be metabolized to inter-mediates in both pathways,15 and bothpathways produce isoprene from thesame intermediate (DMAPP).

It also was known from labeling ex-

periments with 13C-glucose that all car-bon atoms in isoprene are derived fromglucose.16

Collectively, all of these results sup-ported our concept for developing alarge-scale replacement for Hevea rub-ber based on synthetic polyisoprene de-rived from BioIsoprene.

In light of Goodyear’s extensive histo-ry as a major producer of both petrole-um-based isoprene and synthetic poly-isoprene, a BioIsoprene-based approachfor replacing natural rubber is very at-tractive.

Most importantly, Goodyear has ex-tensive experience with both isopreneand synthetic polyisoprene.

In addition to knowing how to producepolymer-grade isoprene and numeroussynthetic polyisoprene rubbers, it knowswell the extent to which Hevea rubbercan be replaced by synthetic polyiso-prene in a broad range of tire applica-tions.

Goodyear does not have the technicalexpertise to develop a process for pro-ducing isoprene via industrial fermen-tation; however, it has an excellent un-derstanding of the business andtechnical risks associated with develop-ing a large-scale replacement for natu-ral rubber based on synthetic polyiso-prene.

BioIsoprene clearly represented agreat opportunity to develop a domes-tic, non-petroleum-based alternative toimported rubber, if Goodyear couldfind the right technology partner to de-velop the industrial fermentationprocess.

DevelopmentAfter evaluating a number of poten-

tial technology partners, Goodyearagreed to join forces with Genencor, aDanisco division, to pursue joint devel-opment of BioIsoprene.

Genencor was particularly attractivebecause of its U.S. leadership in indus-trial biotechnology, track record for com-mercial successes, and focus on totalprocess development.

It also had strong R&D programs withbroad core competencies in industrialbiotechnology.

With Genencor leading efforts to pro-duce BioIsoprene via fermentation andGoodyear leading efforts to recover andpurify BioIsoprene, the collaborationquickly gained momentum.

For example, multiple strains of iso-prene-producing micro-organisms wereproduced by incorporating genes fromisoprene-producing plants into micro-or-ganisms that were genetically engi-neered to produce large amounts of themetabolic intermediates required forisoprene biosynthesis.

Similarly, numerous methods wereevaluated for recovering BioIsoprenefrom fermentation off-gases, and de-tailed analyses of impurity profiles wereperformed to develop methods for pro-ducing isoprene samples suitable forpolymerization.

In short order, the strain develop-ment teams were producing BioIso-prene at levels well-above those previ-ously reported in the literature,17 therecovery team was regularly isolatingsynthetically useful quantities ofBioIsoprene, and the purification andpolymerization team was demonstrat-ing that it could make polyisopreneanalogous to commercially availablesynthetic rubber.

Since that time and in spite of chal-lenging economic circumstances, Goody-ear and Genencor have made steadyprogress toward developing an integrat-ed process to manufacture BioIsoprene.

Large-scale industrialization could beready as soon as 2013, with Genencorleading commercial development.

A closer look Development of an integrated

process for producing, recovering andpurifying BioIsoprene presents manychallenges, but none is greater thanthat posed by engineering micro-organ-isms to produce commodity hydrocar-

The authorFrank J. Feher is a senior re-

search and development associateat Goodyear’s Global Tire Materi-als unit, where he conceived theidea for developing a large-volumereplacement for natural rubberbased on BioIsoprene.

He began working at Goodyearin late 2002 as a senior scientistand internal consultant for devel-opment of new technology withinGoodyear’s former Chemical Divi-sion. Before Goodyear, Feherspent 17 years as a chemistry pro-fessor at the University of Califor-nia, Irvine.

He can be reached at frank_fe-her@goodyear.com.

Fig. 1. Schematic outlining construction of an engineered micro-organism using re-combinant DNA techniques. In this case, the isoprene synthase gene in a geneti-cally modified yeast plasmid is replaced by a synthetic Kudzu isoprene synthasegene.

See BioIsoprene, page 16

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Technical

bons with a cost structure competitivewith existing petroleum-based hydro-carbons.

This can only be accomplished by ag-gressively engineering robust micro-or-ganisms to maximize flow of carbonthrough the isoprene-producing path-ways.

Specific details about how this can beaccomplished are provided in reference18 and the references cited therein.

In general terms, the process for engi-neering isoprene-producing micro-or-ganisms can be understood by referringto Table I and Fig. 1.

Table I illustrates the two known bio-chemical pathways for producing iso-prene. Either can function in isoprene-producing cells and microorganisms.

For micro-organisms naturally usingthe MVA pathway for isoprenoid biosyn-thesis, the steps leading from Acetyl-CoAto isoprene are identical, but the enzymesresponsible for catalyzing these reactionsoften have slightly different structures.

These differences do not change theoverall mechanism for producing iso-prene, but they often influence the rela-tive rates of the individual reactions inthe mechanism.

This allows other reactions to competemore favorably for the intermediatesgenerated by the MVA pathway, whichin turn provides a means for differentorganisms to use similar biochemical re-actions to produce very different mix-tures of biological molecules.

All of the information required for anorganism to make its enzymes neededfor catalyzing the MVA pathway is en-coded in its genes.

If an organism makes little or no iso-prene via the MVA pathway, this is ei-ther because the organism’s genes lackcodes for one or more of the enzymes re-quired to produce isoprene, or becausethe enzymes created from these codesare poor catalysts for one or more reac-tions leading to isoprene.

The key to engineering a useful micro-organism for production of BioIsopreneis to incorporate genes from more effi-cient isoprene-producing organisms intoa robust host that is capable of main-taining its own survival while generat-ing large amounts of isoprene. If neces-sary, it is even possible to incorporatesynthetic genes to influence the rate ofexpression of an enzyme or modify genesto influence the rate or specificity of thereactions.

An example of genetically engineeringmicro-organisms can be gleaned fromFig. 1. In this figure the diagram repre-sents a plasmid which contains geneticinformation that allows it to replicate inmicro-organisms.

The diagram in the upper right repre-sents a synthetic kudzu ispS gene se-quence. The ispS gene encodes the Iso-

prene synthase, the enzyme required toproduce isoprene from DMAPP. ThisispS gene is cloned into the plasmid andintroduced into micro-organisms.

Because all micro-organisms produceDMAPP, the introduction of the ispSgene now allows them to produce iso-prene.

Similar strategies can be used to mixand match genetic material from abroad range of micro-organisms that caneither produce isoprene or support pro-duction of isoprene.

Prior to Genencor’s work, previous ef-forts to produce isoprene via fermenta-tion produced only very small amountsof isoprene.17

As a result of Genencor’s work, thissituation has changed dramatically.

This is best illustrated by Fig. 2,which corresponds to the data in Figs.78A, 78B and 78D in reference 18.

This figure contains data from a glu-cose-fed fermentation performed at 34°Cin a 15-L bioreactor with geneticallymodified E. coli cells containing genesfrom other organisms, including the iso-prene synthase gene from P. alba (i.e.,the white poplar tree).

Fig. 2 shows the cell density profilewithin the bioreactor, which exponen-tially increases during the growth phaseand is followed by a stationary phase.

The isoprene titer increased over thecourse of the fermentation to a maxi-mum value of 33.2 g/L at 40 h (and 48.6g/L at 59 h). Finally, the total amount ofisoprene produced by the fermentationis shown, which was 281 g after 40hours and 451 g after 59 hours (Fig. 2).

These now dated results convincinglyshow that it indeed is possible to engi-neer microorganisms for production ofBioIsoprene.

Since these experiments were first de-scribed, the state-of-the-art has contin-ued to advance. Goodyear and Genencornow are on track to have an integratedprocess ready to manufacture BioIso-prene on an industrial scale as early as2013.

ConclusionThe development of BioIsoprene repre-

sents a major achievement for industrialbiotechnology because it has the poten-tial to provide enormous quantities of abasic hydrocarbon that, in principle, canbe used as a feedstock for a large numberof value-added products. One of theseproducts is synthetic cis-polyisoprene,which for decades has been recognized asa suitable replacement for natural rub-ber in many applications.

The BioIsoprene process being pio-neered by Goodyear and Genencor final-ly offers the very real possibility for ob-taining the quantities of low-costisoprene needed to produce a meaning-ful large-volume alternative to Heveanatural rubber.

AcknowledgementsThis project would not have been pos-

sible without support and collaboration

from a large number of talented peoplefrom Goodyear and Genencor.

We are especially grateful for the con-tributions made by the early project team.For Goodyear, this team included AaronPuhala, Len Sikora, Erin Webster, MegNoethen, Tim Sabo, Tang Wong, StephanRodewald, Dave Zanzig, David Benko,Jesse Roeck and Bill Hopkins, who enthu-siastically served as Goodyear’s execu-tive-level champion during the project’scritical embryonic stage. For Genencor,this team included Karl Sanford and RichLaDuca.

References1. International Rubber Study Group, Rubber In-dustry Report 2009, Vol. 8, No. 10-12, April-June2009.2. Davis, Wade. The Rubber Industry’s BiologicalNightmare. Fortune Magazine, August 4, 1997.3. Barry, J. M. 1918 Revisited: Lessons and Sugges-tions for Further Inquiry. In The Threat of PandemicInfluenza: Are We Ready? Workshop Summary; Na-tional Academies Press: Washington., DC, 2005; p 58.4. (a) Bonner, J. History of Natural Rubber. InGuayule Natural Rubber, Whitworth, J. W.; White-head, E. E.; Eds.; GAMC/USDA-CSRS: Tucson,Ariz., 1991, pp. 1–16. (b) Cornish, K., Schloman, W.W., Encyclopedia of Polymer Science and Technolo-gy, Wiley: New York, 2004; Vol. 11, 670-698. 5. (a) Waley, W. G.; Bowen, J. S. Russian Dandelion(Kok-Saghyz): An Emergency Source of NaturalRubber, USDA Misc Pub. No. 618, June 1947. (b)Van Beilen, J. B.; Poirier, Y. Establishment of NewCrops for the Production of Natural Rubber. Crit.Rev. Biotechnol., 2007, 27, 217-231.6. Mark, J. E.; Erman, B.; Eirich, F. R. Science andTechnology of Rubber, 2nd Ed., Academic Press:New York, 1994.7. (a) Tanaka, Y.; Sakdapipanich, J. T. ChemicalStructure and Occurrence of Natural Polyisoprenes.Biopolymers 2001, 2, 1-25. (b) Tarachiwin, L.; Tana-

ka, Y.; Sakdapipanich, J. T. Structure and Origin ofLong-Chain Branching and Gel in Natural Rubber.KGK, Kautschuk Gummi Kunststoffe 2005, 58, 115-22. (in English)8. Mooibroek, H.; Cornish, K. Alternate Sources ofNatural Rubber. Appl. Microbiol. Biotechnol. 2000,53, 355-65.9. Bohmert, K.; Peoples, O. P.; Snell, K. D. Metabol-ic Engineering: Plastids as Bioreactors. In Molecu-lar Biology and Biotechnology of Plant Organelles;Daniell, H., Chase, C. D., Eds.; Kluwer AcademicPublishing: Netherlands, 2004, p 559-585.10. President G. W. Bush, State of the Union Ad-dress, January 31, 2006 (http://www.npr.org/tem-plates/story/story.php?storyId=5181905)11. President J. F. Kennedy, Speech to Congress, May25, 1961 (http://history1900s.about.com/od/1960s/a/jfk-moon.htm)12. Sharkey, T. D.; Yeh, S. Isoprene Emission fromPlants. Annu. Rev. Plant Physiol. Plant Mol. Biol.2001, 52, 407-36.13. Bramley, P. M. Isoprenoid Metabolism. In PlantBiochemistry; Dey, P. M., Harborne, J. B., Eds.;Academic Press: New York, 1997; pp 417-438.14. (a) Sharkey, T. D.; Yeh, S.; Wiberley, A. E.; Fal-bel, T. G.; Gong, D.; Fernandex, D. E. Evolution ofthe Isoprene Biosynthetic Pathway in Kudzu. PlantPhysiology 2005, 137, 700-712. (b) Lange, B. M.; Ru-jan, T.; Martin, W.; Croteau, R. Isoprenoid Biosyn-thesis: The Evolution of Two Ancient and DistinctPathways Across Genomes. Proc. Nat. Acad. Sci.2000, 97, 13172-7.15. Vogt, D. J., Vogt, J. G. Biochemistry, 3rd Ed.;Wiley: New York, 2004; Chapter 17.16. Wagner, W. P.; Helmig, D.; Fall, R. IsopreneBiosynthesis in Bacillus subtilis via the Methylerythri-tol Phosphate Pathway. J. Nat. Prod. 2000, 63, 37-40 17. (a) Miller, B; Oschiniski, C.; Zimmer, W. FirstIsolation of an Isoprene Synthase Gene from Poplarand Successful Expression of the Gene in Es-cherichia coli. Planta 2001, 213, 483-487. (b) Fall, R.R.; Kuzma, J.; Nemecek-Marshall, US Patent5,849,970, Dec. 15, 1998.18. Cervin, M. A.; Whited, G. M.; Chotani, G. K.;Valle, F.; Fioresi, C.; Sanford, K. J.; McAuliffe, J. C.;Feher, F. J.; Puhala, A. S.; Miasnikov, A.; Aldor, I. S.US Patent Appl. US2009/0203102 A1, Aug. 13, 2009.

Fig. 2. Time course data of E. coli cells expressing heterologous MVA pathway andisoprene synthase genes and grown in a 15-L, glucose fed-batch bioreactor at34°C. The black diamonds show the isoprene titer profile over the course of the cellculture. The black squares show the total isoprene produced during the fermenta-tion. The open circles show the cell density profile within the bioreactor as meas-ured by optical density at a 550 nm wavelength.

BioIsopreneContinued from page 15

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