Biofuels! Processes and products

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1 Biofuels! Processes and products Part 1: First Generation Biofuels CHEG 614/814 3/24/2015 Tyler Josephson

2 Biofuels: Processes and Products 1. What is fuel? 2. What is biomass? 3. Current biofuel technologies 1. Ethanol (corn and cellulosic) 2. Biodiesel 3. Green Diesel 4. Next-generation biofuel technologies 1. Gasification 2. Pyrolysis 3. Liquid-phase processing 4. Algae-based fuels

3 Fuel Chemistry ctane and cetane number both measure how easily fuel will ignite spontaneously Branching and oxygen stabilize free radicals, preventing pre-ignition Good for gasoline, bad for diesel Isooctane: 100 octane Hexadecane: 100 cetane Fuel Energy Density Specific Energy ctane Cetane (MJ/L) (MJ/kg) Number Number Gasoline Diesel Ethanol Biodiesel

4 Motivations for Biofuels ca Environmental Reduce C 2 emissions Political Energy independence Economic Add value to agricultural products and waste Peak il il is fossil resource, and it is becoming depleted and scarce

5 Motivations for Biofuels Now Environmental Reduce C 2 emissions Political Energy independence Economic Add value to agricultural products and waste Peak il US boom in shale gas and shale oil has changed the picture il is fossil resource, and it is becoming depleted and scarce

6 End of Peak il? In the 1950s, Hubbert predicted US peak oil production in about 1970, but new drilling technology has changed the picture with shale oil However, oil is still a fossil resource June 2004 "US Crude il Production versus Hubbert Curve" by RockyMtnGuy - _Curve.png#/media/File:US_Crude_il_Production_versus_Hubbert_Curve.png

7 The Ideal Biocycle 2 Ragauskas et al., Sci. 311, 484 (2006) A closed/neutral carbon path Biomass is the only source of renewable fixed carbon C 2 is also possible carbon source, but requires energy input

8 Biomass Aspen Trees 4 H CH 2 H H ß 1 R 4 CH 2 R 1 CH 2 H ß 4 R R R ß 4 R 1 CH 2 H 1 ß Lignin (24%) H H 1 a CH 2 H H Hemicellulose (21%) Xylan, Galactan, Arabinan, Mannan) Cellulose (45%) glucan Extractives (9.5%) Uronic & acetyl acids H H CH 2 H H H CH 2 H H H CH 2 H H H CH 2 H Ash (0.5%) Yellow - Ca, Mg, K Myrcene Limonene -Terpinene ß H p-cymene Terpinolene a-terpineol

9 Diversity of Biomass Composition Ash Uronic Acids Extractives Lignin Hemicellulose Cellulose / Algin Corn Grain Corn Stover Cane Cane Bagasse Pine Aspen

10 Structure of Plant Material

11 Cellulose: (C 6 H 10 5 ) n A polysaccharide consisting of a linear chain of several β(1 4) linked of D-glucose units Linear strands with extensive H-bonds between them, leading to a highly stable, semi-crystalline structure that is resistant to degradation Most common organic compound on Earth About 33 percent of all plant matter is cellulose Cellulose content of cotton is 90% (n= ) and that of wood is 50% (n=800-10,000) For industrial use, cellulose is mainly obtained from wood pulp and cotton. Mainly used to produce cardboard and paper Breakdown: cellulolysis Enzymes break down cellulose into smaller polysaccharides called cellodextrins or completely into glucose units; this is a hydrolysis reaction

12 Hemicellulose Comprised of several sugars in addition to glucose, including especially xylose, but also mannose, galactose, rhamnose, arabinose Forms shorter chains - around 200 sugar units as opposed to 7,000-15,000 glucose molecules in the average cellulose polymer Is branched, whereas cellulose is unbranched Is easier to break down than cellulose

13 Lignin Lignin is a large, cross-linked, racemic macromolecule with large molecular mass It is relatively hydrophobic and aromatic Difficult to break down with enzymes Paracoumaryl alcohol Coniferyl alcohol Sinapyl alcohol Lignin

14 Carbohydrates Glycerol C 3 H 8 3 or C 3 (H 2 ) 3 H 2 Boiling Point ~ 300 C α-d-(+)-glucose C 6 H 12 6 or C 6 (H 2 ) 6 α Starch (C 6 H 10 5 monomers) α(1-4) linkage (starches) highly branched coiled Cellulose (C 6 H 10 5 monomers) β(1-4) linkage (cellulose) no branching linear (crystalline & amorphous) H H CH 2 H H H CH 2 H H H CH 2 H H H CH 2 H

15 Comparison of biomass molecules to crude and refinery molecules Many functional groups Easier to convert them into oxygenated molecules (alcohols, ketones, aldehydes, acids) Thermally unstable (~ o C) Low volatility Need new catalysts to remove some of the functional groups D-Glucose C 6 H 12 6 or C 6 (H 2 ) 6

16 Sourcing Petroleum Products from Biomass Building Blocks Biomass Crude il Fuels, Solvents, Polymers, Dyes, Adhesives [1] Top Value-Added Chemicals from Biomass, PNNL

17 Biofuels in the U.S. Diverse set of biofuel alternatives In 2013, corn ethanol fuel: 13 billion gallons/year In 2013, biodiesel fuel: 1.3 billion gallons/year , 4 cellulosic ethanol plants installed with total capacity of ~0.1 billion gallons/year Federal policies propel R&D 1 $0.54/gallon tax credit for corn ethanol expired in 2011 $1.00/gallon tax credit for biodiesel until at least 2016 $1.01/gallon tax credit for cellulosic ethanol until at least BG of renewable fuel by 2012 (Energy Policy Act) 36 BG of renewable fuel by 2022 (Renewable Fuel Standard) DE goals by Replace 30% of transportation fuel with biofuels and 25% of organic chemicals from biomass 1 Ethanol Producer Magazine, Ragauskas et al., Sci. 311, 484 (2006)

18 Ethanol Corn and cellulosic

19

20 Current and future ethanol production Today s bioethanol plant process relies largely on Fermentation of starch from corn in the U.S. Fermentation of sugar cane in Brazil Need to move toward corn stovers, trees, and other low-cost agricultural and municipal waste materials Typically have higher amounts of cellulose and hemicellulose Efficient, cost-effective depolymerization is key 4 commercial cellulosic ethanol plants operating in 2014

21 Greenhouse gas (GHG) emissions 1 There is no clear consensus on the net energy cycle and benefits of using biofuels Co-products must be considered in analysis Databases not as accurate yet? Corn ethanol reduces petroleum use by ~95% on an energetic basis (at the expense of coal and NG) and reduces GHG emissions only by ~13%. Cellulosic ethanol offers large reductions in GHG Ethanol Today Cellulose 1 Farrell et al. Science 311, 506 (2006)

22 Evaluation metrics: Energy input and GHG 1 1 Farrell et al. Science 311(27), 506 (2006) Ship Nebraska corn to a lignite-powered ethanol plant in North Dacota Ethanol from food produces nearly the same GHGs as crude and has similar energy intensity but shifts from crude to NG and coal utilization! Cellulosic ethanol reduces crude oil need and GHG emissions substantially

23 Debate on emissions, energy gain, etc. Use of U.S. Croplands for Biofuels Increases Greenhouse Gases Through Emissions from Land Use Change Most prior studies have found that substituting biofuels for gasoline will reduce greenhouse gases because biofuels sequester carbon through the growth of the feedstock. These analyses have failed to count the carbon emissions that occur as farmers worldwide respond to higher prices and convert forest and grassland to new cropland to replace the grain (or cropland) diverted to biofuels. Using a worldwide agricultural model to estimate emissions from land use change, we found that cornbased ethanol, instead of producing a 20% savings, nearly doubles greenhouse emissions over 30 years and increases greenhouse gases for 167 years. Biofuels from switchgrass, if grown on U.S. corn lands, increase emissions by 50%. This result raises concerns about large biofuel mandates and highlights the value of using waste products.

24 Biodiesel

25 Keys Facts on Biodiesel Fuel containing 20% biodiesel is labeled B20, while pure biodiesel is referred to as B100 It has better lubricity and more complete combustion Viscosity can be an issue: B100 can gel at low temperatures, so not recommended for cold weather Transesterification is the process of exchanging the alkoxy group of an ester with another alcohol. These reactions are often catalyzed by an acid or a base

26 Triglycerides and FFA Found in plant oils and animal fat Glycerol esterified with three fatty acids If fatty acids are present without glycerol, they are called free fatty acids (FFA) Triglyceride Example Free Fatty Acid Example

27 Chemistry of Biodiesel Source: Gerpen, J. V. (2005). "Biodiesel Processing and Production." Fuel Processing Technology 86:

28 Biodiesel Production ils from plants or animals are expensive Sometimes, price of biodiesel < price of soybean oil Today, soybean oil is $2.30/gal and diesel fuel is $2.86/gal Use of waste oils is a great way forward, but waste oils have high content of FFA

29 Side Reactions: Soap! Transesterification can be catalyzed by base or acid Base catalysts are faster, but watch out for soap! Free fatty acids must be removed first by esterification using acid catalyst

30 Revised Process: Handling FFA BIG potential for heterogeneous catalyst development No separation of homogeneous catalyst, no saponification reaction

31 Glycerol 100 tons of triglyceride and 10 tons of methanol will make ~100 tons of biodiesel and 10 tons of glycerol A worldwide glut of glycerin created as a by-product of manufacturing biodiesel fuel is precipitating the shutdown of traditional glycerin plants and the opening of other plants that use glycerin as a raw material. C&EN News, 2/6/2006 Active area of research efficient processes to upgrade glycerol Glycerol Acrolein Glycerin acetate Propylene glycol Acrylic Acid

32 Green Diesel

33 Key Facts on Green Diesel Green diesel is a true hydrocarbon NT a methyl Identical or superior combustion properties to petro diesel Hydrogenation of oils produces alkanes Not as big as biodiesel yet, but being actively developed by Honeywell UP, Valero, ConocoPhillips Green jet fuel also produced Boeing tested flight

34 Chemistry of Green Diesel Decarboxylation and decarbonylation reduce H 2 consumption, but also reduce carbon yield dia/image7_w.jpg

35 UP Green Diesel Process Propane and light ends are either fuel or source of hydrogen

36 Perspective from il Companies Co-processing in existing refineries Simultaneous hydrogen generation Production of high value products Examples from UP s slides: Biorefineries/Presentation-05.pdf

37 Courtesy of T. Marker (Team leader)

38

39

40 Regular diesel has cetane of ~45-55

41 Biofuels: Processes and Products 1. What is fuel? 2. What is biomass? 3. Current biofuel technologies 1. Ethanol (corn and cellulosic) 2. Biodiesel 3. Green Diesel 4. Next-generation biofuel technologies 1. Gasification 2. Pyrolysis 3. Liquid-phase processing 4. Algae-based fuels

Abstract Process Economics Program Report 251 BIODIESEL PRODUCTION (November 2004)

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