Carbohydrates in Sustainable Development I

211 Pages·2010·3.435 MB·English

by  Siegfried Peters, Thomas Rose, Matthias Moser (auth.), Amélia P. Rauter, Pierre Vogel, Yves Queneau (eds.)

294
Topics in Current Chemistry
Editorial Board:
A. de Meijere K.N. Houk C.A. Hunter H. Kessler
l l l
J.-M. Lehn S.V. Ley M. Olivucci J. Thiem B.M. Trost
l l l l
M. Venturi P. Vogel H. Wong H. Yamamoto
l l l
Topics in Current Chemistry
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Carbohydrates in Sustainable
Development I
Renewable Resources for Chemistry
and Biotechnology
Volume Editors:
Ame´lia P. Rauter (cid:1) Pierre Vogel (cid:1) Yves Queneau
With Contributions by
I.Andre´ (cid:1)C.M.S.Anjo(cid:1)T.Benvegnu(cid:1)S.M.Cardoso(cid:1)M.A.Coimbra(cid:1)
F. DiRenzo(cid:1) A.P.Duarte(cid:1) B.Estrine (cid:1) J.A.Figueiredo(cid:1)
J.M.Garc´ıaFerna´ndez(cid:1) E.Guibal (cid:1) N.Hoffmann (cid:1) M.I. Ismael(cid:1)
J.A. Lopes-da-Silva (cid:1) F.Martel(cid:1) P.Monsan (cid:1) S.Morel (cid:1) M.Moser(cid:1)
C.Ortiz Mellet (cid:1) S.Peters(cid:1) R.Plantier-Royon(cid:1) C. Portella(cid:1)
G.Potocki-Ve´rone`se (cid:1) F.Quignard (cid:1) M.Remaud-Sime´on(cid:1) T. Rose(cid:1)
J.-F. Sassi
Editors
Prof.Dr.Ame´liaP.Rauter Prof.Dr.PierreVogel
UniversidadedeLisboa LaboratoryofGlycochemistryand
Fac.Cieˆncias AsymmetricSynthesis(LGSA)
Depto.Qu´ımicaeBioqu´ımica SwissInstituteofTechnology(EPFL)
CentrodeQu´ımicaeBioqu´ımica CH1015Lausanne
Ed.C85Piso Switzerland
CampoGrande pierre.vogel@epfl.ch
1749-016Lisboa
Portugal
[email protected]
Prof.Dr.YvesQueneau
InstitutdeChimieetBiochimie
Mole´culairesetSupramole´culaires
UMR5246CNRS–Universite´deLyon
LaboratoiredeChimieOrganique
INSALyon,Baˆt.J.Verne
69621Villeurbanne
France
[email protected]
ISSN0340-1022 e-ISSN1436-5049
ISBN978-3-642-14836-1 e-ISBN978-3-642-14837-8
DOI10.1007/978-3-642-14837-8
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Volume Editor
Prof.Dr.Ame´liaP.Rauter Prof.Dr.PierreVogel
UniversidadedeLisboa LaboratoryofGlycochemistryand
Fac.Cieˆncias AsymmetricSynthesis(LGSA)
Depto.Qu´ımicaeBioqu´ımica SwissInstituteofTechnology(EPFL)
CentrodeQu´ımicaeBioqu´ımica CH1015Lausanne
Ed.C85Piso Switzerland
CampoGrande pierre.vogel@epfl.ch
1749-016Lisboa
Portugal
[email protected]
Prof.Dr.YvesQueneau
InstitutdeChimieetBiochimie
Mole´culairesetSupramole´culaires
UMR5246CNRS–Universite´deLyon
LaboratoiredeChimieOrganique
INSALyon,Baˆt.J.Verne
69621Villeurbanne
France
[email protected]
Editorial Board
Prof.Dr.ArmindeMeijere Prof.Dr.Jean-MarieLehn
Institutfu¨rOrganischeChemie ISIS
derGeorg-August-Universita¨t 8,alle´eGaspardMonge
Tammanstr.2 BP70028
37077Go¨ttingen,Germany 67083StrasbourgCedex,France
[email protected] [email protected]
Prof.Dr.KendallN.Houk Prof.Dr.StevenV.Ley
UniversityofCalifornia UniversityChemicalLaboratory
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[email protected] [email protected]
Prof.Dr.ChristopherA.Hunter Prof.Dr.MassimoOlivucci
DepartmentofChemistry Universita`diSiena
UniversityofSheffield DipartimentodiChimica
SheffieldS37HF,UnitedKingdom ViaADeGasperi2
c.hunter@sheffield.ac.uk 53100Siena,Italy
[email protected]
vi EditorialBoard
Prof.Dr.HorstKessler Prof.Dr.JoachimThiem
Institutfu¨rOrganischeChemie Institutfu¨rOrganischeChemie
TUMu¨nchen Universita¨tHamburg
Lichtenbergstraße4 Martin-Luther-King-Platz6
86747Garching,Germany 20146Hamburg,Germany
[email protected] [email protected]
Prof.Dr.BarryM.Trost Prof.Dr.HenryWong
DepartmentofChemistry TheChineseUniversityofHongKong
StanfordUniversity UniversityScienceCentre
Stanford,CA94305-5080,USA DepartmentofChemistry
[email protected] Shatin,NewTerritories
[email protected]
Prof.Dr.MargheritaVenturi
Prof.Dr.HisashiYamamoto
DipartimentodiChimica
Universita`diBologna ArthurHollyComptonDistinguished
viaSelmi2 Professor
40126Bologna,Italy DepartmentofChemistry
[email protected] TheUniversityofChicago
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pierre.vogel@epfl.ch
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Preface
Globalwarmingandtheincreasingdemandforrawmaterialsmakethetransitiontoa
sustainableeraofenergyandmaterialsanecessity.Thedevelopmentofnewchemical
processesforintermediatesnotbasedoncoalandoilisbecomingessential[1].Our
economic system is currently built onfinite resources,for which we will sooner or
later need a substitute. Biomass is considered one of the possible alternatives to
develop inthenearfuture,which could contributeinthe immediate toincreasethe
lifetime of available fossil forms of carbon. The term “biomass” means any plant-
derived organic matter available on a renewable basis, including energy crops and
trees,agriculturalfoodand feedcrops,agriculturalcropwastesand residues, wood
waste and residues, aquatic plants, animal waste,municipal waste,and other waste
materials [2].Biomassresources can beusedtoproduce anarray ofenergy-related
products including electricity, liquid,solid, and gaseous fuels, heat, chemicals, and
other materials of high-added value. Biomass renewable energy is also considered
relatively“sustainable,”sincetherelatedenvironmentalandsocialimpactisnormally
more benign than that of fossil or nuclear fuels. However, large areas of land are
necessary to grow energy crops, which introduce some concerns about the impact
of using land for this purpose when it should first be used to produce food. Only
theleft-oversandwastesfromagricultureshouldbeexploitedasafuelsourceforthe
manufacture of carbon-based materials (e.g., commodities so much needed by our
civilization such as cloths, detergents, paints, pesticides, herbicides, vehicles, and
drugs). This observation should stimulate the use of solar energy and sea water to
produce electricity and water suitable to irrigate desert land for food and more
biomass production. Such projects would provide work for many people in poor
regionsoftheworld.
Combustion of biomass and biomass-derived fuels can produce air pollution;
how serious this impact is will depend on how carefully the resource is managed.
Today, a wide variety of production and conversion methods exist, each with
different environmental impacts. However,renewable energysourcescan becon-
sidered sustainable in the sense that they cannot come to an end, although often,
as is the case of biomass, they require an “intelligent” management (adequate
use of water and readily degradable pesticides) if they are to be used sustainably.
ix
x Preface
Byintegratingtheproductionofhigher-valuechemicalsintofuelsproduction,the
overall efficiency of all energy-related products will be improved, thus matching
thegoalsofecologicalrestorationandeconomicdevelopment(foradiscussionof
this topic, see http://www.nrel.gov/biomass/biorefinery.html) [3]. Producing fuels
andchemicalsfrombiomassisnotanewconcept.Vegetableoil,cellulose(wood),
ethanol,methanol,andmanyotherbiomass-basedchemicalshavebeeninusesince
more than two centuries to make solvents, paints, adhesives, synthetic cloths and
so on. By the late 1960s, when petrochemicals began to dominate the market,
many of these bio-derived products were displaced by petroleum derivatives.
The energy crisis of the 1970s generated a renewed interest in the synthesis of
fuels and materials from bioresources, but this interest decreased immediately in
the subsequent decade as the oil price abated. Presently, economic, geopolitical,
and environmental concerns are responsible for the renewed interest in biomass
exploitation.Inaddition,itisnoteworthythatnewadvancesinbiotechnologyand
chemicalprocesseshavesignificantlyreducedthecostsofproducingbiochemicals;
manybiochemicalscanalreadycompeteeconomicallywithpetrochemicals.When
environmentalbenefitsareconsidered,biochemicalsmayhaveevenlowerproduc-
tion,handling,useandriskmanagementcoststhantheirpetroleum-basedcounter-
parts.Today,biomasscansubstitutepetroleumfeedstocksintheproductionofmost
fuels and chemicals. Nevertheless, different processes must be developed; fossil
fuelsarehydrocarbons,i.e.,variouscombinationsofcarbonandhydrogen;biomass
componentsaremainlycarbohydrates,i.e.,variouscombinationsofcarbon,hydro-
gen,andoxygen.Theshiftfrompetroleumhydrocarbonstooxygenatedbio-based
feedstocks may create new opportunities in the chemical and biochemical indus-
tries. Important building blocks may be produced from sugars and these can be
transformed into new families of useful molecules [4]. The presence of oxygen
makesitmorechallengingtosynthesizesomeproductsandeasiertoprepareothers;
consideringthewiderangeoftypesofbiomassshouldmakeitpossibletomakenew
andvaluableproductsnotmadefrompetrochemicals.However,toavoidrecreating
the environmental problems arising from many of the processes in use today, it is
essential that the use of renewable biomass is complemented by the application of
green chemicalprocessesandtechnologiestogenerateenvironmentallycompatible
products based ongreen and sustainable supplychains. Currently, there is growing
internationalinterestinthedevelopmentofsaferalternativestoproblematicchemi-
cals,materials,andproducts.Forexample,acentralgoaloftheEuropeanCommuni-
ty,asexpressedbythenewregulationonRegistration,Evaluation,andAuthorization
of Chemicals (REACH), is the substitution of problematic chemicals with safer
alternatives (http://www.reachcentrum.org). Clean technology concerns the reduc-
tionofwastefromanindustrialchemicalprocesstoaminimum,anditrequiresthe
rethinkingandredesignofmanycurrentchemicalprocesses.
The two books, Vols. 294 and 295, are based on the lectures presented at the
Carbohydrates as Organic Raw Materials (CORM) V conference held in Lisbon
(January20–23,2009),organizedandchairedbyAme´liaPilarRauter(Universityof
Lisboa)andYvesQueneau(UniversityofLyon,INSALyon),withthecollaboration
ofFriederLichtenthaler(TechnischeUniversita¨tDarmstadt)asHonoraryChairman,
whohasalsostartedthesemeetingsin1990.Aseriesofconferencestookplaceuntil