Stochastic Synthesis of Natural Organic Matternom/Papers/Stochastic.pdfStochastic Synthesis of...
Transcript of Stochastic Synthesis of Natural Organic Matternom/Papers/Stochastic.pdfStochastic Synthesis of...
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Stochastic Synthesis ofNatural Organic MatterSteve Cabaniss, UNMGreg Madey, Patricia Maurice, Yingping Huang, NDLaura Leff, Ola Olapade KSUBob Wetzel, UNCJerry Leenheer, Bob Wershaw USGS
Fall 2002
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What is NOM? Sources:• Plant and animal decay products
– Terrestrial- woody and herbaceous plants
– Aquatic- algae and macrophytes
• Structures– cellulose, lignins, tannins, cutin
– proteins, lipids, sugarsOOHOHOHOOHOHOOHOHOOOOHHOOHOHOHOOHOetc.
OOOHOHOHHOOHQuercetin
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What is NOM? Composition
45-55 Wt% Carbon
35-45 Wt% Oxygen
3-5 Wt% Hydrogen
1-4 Wt% Nitrogen
Traces P, S
MW 200-20,000 amu
Equiv. Wt. 200-400 amu
10-35% aromatic C
OOHOHOOHOOHOOHOOHOOHOOHOOOOHOOHOOOOHLeenheer, et al., 1998possible fu
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What is NOM?
A mixture of degradation and repolymerization productsfrom aquatic and terrestrial organismswhich is heterogeneous with respectto structure and reactivity.
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NOM + O2 H2O2
+ OH·
+ O2-
NOM Interactions with sunlight
Photosensitizer
Light attenuation
Fe(III)-NOM Fe(II) + NOM + CO2
+ etc.
Direct photoredox
Abs
Wavelength
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NOM Interactions with mineral surfacesHemi-micelleformation
Fe(II)
Fe(III)
Reductivedissolution
Adsorption Acid or complexingdissolution
Al
e-
Adsorbed NOM coatings impart negative charge and create a hydrophobic microenvironment
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NOM Interactions with microbes
Ingestion:Energy andNutrients
e- e-
Electron shuttle
Cu2+
Cu
Metal ion complexationand de-toxification
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NOM Interactions with pollutants+
Binding to dissolved NOM increases pollutant mobility
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NOM in water treatment
+ HOClCHCl3 + CHCl2Br + CCl3COOHand other chlorinated by-products
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Why study NOM?
Natural ecosystem functions Nutrition, buffering, light attenuation
Effects on pollutants Radionuclides, metals, organics
Water treatment DBP’s, membrane fouling, Fe solubility
Carbon cycling & climate change
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NOM Questions:
• How is NOMproduced &transformed in theenvironment?
• What is its structureand reactivity?
• Can we quantify NOMeffects on ecosystems& pollutants?
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Environmental Synthesis of Natural Organic Matter
NOMHumic substances& small organics
NOMHumic substances& small organics
CO2CO2
Cellulose
Lignins
Proteins
Cutins
Lipids
Tannins
O2
lightbacteriaH+, OH-
metalsfungi
O2
lightbacteriaH+, OH-
metalsfungi
O2
lightbacteriaH+, OH-
metalsfungi
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Simulating NOM SynthesisDeterministic Reaction Kinetics
For a pseudo-first order reaction
R = dC/dt =k’ CR = rate (change in molarity per unit time)
C = concentration (moles per liter)
k’ = pseudo-first order rate constant
(units of time-1)
Based on macroscopic concentrations
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Deterministic Reaction Kinetics:Solve a system of ODE’s
• Begin with initial Ci for each of Ncompounds, kj for each of M reactions
• Apply Runge-Kutta or predictor-correctormethods to calculate )Ci for each time step(use Stiff solvers as needed)
• Repeat for desired length of simulation,obtaining results as Ci versus time
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Problem w/ ODE approach:Size and Computation Time
• Assuming N > 200 (different molecules)
• Assume M = 20 x N (20 reactions permolecule)
• Total set of >4000 very stiff ODE’s isimpractical (transport eqns not included)
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Problem w/ODE Approach:Knowledge Base
• Structures of participating moleculesunknown
• Pertinent reactions unknown
• Rate constants kj unknown
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Simulating NOM SynthesisProbabilistic Reaction Kinetics
For a pseudo-first order reaction
P = k’ _tP = probability that a molecule will react
with a short time interval _t
k’ = pseudo-first order rate constant
units of time-1
Based on individual molecules
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Stochastic algorithm: Initialization
• Create initial pseudo-molecules (objects)– Composition (protein, lignin, cellulose, tannin)
– Location (top of soil column, stream input)
– Input function (batch mode, continuousaddition, pulsed addition)
• Create environment– specify pH, light, enzyme activity, bacterial
density, humidity, To, flow regime
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Stochastic Algorithm:Reaction Progress
• Chemical reaction: For each time-slice, eachpseudo-molecule– determine which reaction (if any) occurs– modify structure, reaction probabilities
• Transport: For each time-slice, each pseudo-molecule– Determine mobility– Modify location, reaction probabilities
• Repeat, warehousing ‘snapshots’ of pseudo-molecules and aggregate statistics
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Stochastic Algorithm:Advantages
• Computation time increases as # molecules,not # possible molecules
• Flexible integration with transport
• Product structures, properties not pre-determined
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Stochastic synthesis: Data model
Pseudo-Molecule
Elemental Functional StructuralComposition
CalculatedChemical Properties
and Reactivity
LocationOriginState
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Average Lignin Molecule:Oligomer of 40 coniferyl alcohol subunits
Numbers of atoms Numbers of functional groups400 Carbon 40 Total ring structures322 Hydrogen 40 Phenyl rings81 Oxygen 1 Alcohol
1 Phenol118 Ether linkages
OHOOH3COH3COOCH3Oetc.
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Model reactions transform structure
Ester Hydrolysis
Ester Condensation
Amide Hydrolysis
Dehydration
Microbial uptake
RCOORH or OH ROOH HOR OHH
OHHROHRHH RR
CO OO O y e
COO OO O O
NOMNOM
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Reaction Probabilities:P calculated from
Molecular structure
Environment (pH, light intensity, etc.)
Proximity of near molecules
State (adsorbed, micellar, etc.)
Length of time step, _t
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Example: Ester Hydrolysis
P = (# Esters) A e-Ea/RT (1 + b[H+] + c[OH-])
Where A = Arrhenius constant
Ea = activation energy
R = gas constant
T = temperature, Kelvins
b = acid catalyzed pathway
c = base catalyzed pathway
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Property prediction
EnvironmentalLight absorbanceMolecular weightAcid content & pKa BioavailabilityKow
Metal binding K
AnalyticalElemental %Titration curvesIR SpectraNMR spectra
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Property Calculation Methods
• Trivial- MW, elemental composition,Equivalent weight
• Simple QSAR- pKa, Kow
• Interesting– Bioavailability
– Light absorption
– Metal binding
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Presentation and Analysis
• Spatial mapping of molecules
• Results stored in Oracle database
• Remote query via WWW interface
• Standard graphs of reaction frequency,molecular properties versus time
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Trial: Can we convert lignin oligomer(MW ~6000) in “NOM” ?
Atmospheric O2 No light
Neutral pH No surfaces
Moderate enzyme activity No transport
27 months reaction time
OHOOH3COH3COOCH3Oetc.
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Num
ber
of M
olec
ules
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% Carbon
% Oxygen
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Mw
Mn
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% Carbon
% Oxygen
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Mw
Mn
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Lignin -> NOM conversion
• Elemental composition similar to wholewater NOM
• Average MW within range for aquaticNOM, soil NOM respectively
• Aromaticity lower than normal
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Stochastic synthesisPreliminary tests
•Chromatography-like NOM movement in soils and sub-surface
•Log-normal distribution of NOM molecular weights
•Rapid consumption of proteins
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Current development
• Expanding reaction set
• Determination of reaction probabilities
• Best method of spatial mapping– Discrete grid vs Continuous space
• Remote query capability
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Next Steps-
• Property prediction algorithms
• Data mining capabilities
• Comparison with lab and field results
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Stochastic Synthesis of NOM
NOMHumic substances& small organics
NOMHumic substances& small organics
CO2CO2
Cellulose
Lignins
Proteins
Cutins
Lipids
Tannins
O2
lightbacteriaH+, OH-
metalsfungi
O2
lightbacteriaH+, OH-
metalsfungi
O2
lightbacteriaH+, OH-
metalsfungi
Goal: A widely available, testable, mechanistic model of NOM evolution in the environment.
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Financial Support
NSF Division of Environmental Biology andInformation Technology Research Program
Collaborating Scientists
Steve Cabaniss (UNM) Greg Madey (ND)
Jerry Leenheer (USGS) Bob Wetzel (UNC)
Bob Wershaw (USGS) Patricia Maurice (ND)
Laura Leff (KSU)