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(12) Patent Application Publication (10) Pub. No.: US 2014/0335578 A1 SAN Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2014/0335578 A1 SAN Et Al US 20140335578A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0335578 A1 SAN et al. (43) Pub. Date: Nov. 13, 2014 (54) INTEGRATED BIODIESEL PROCESS Publication Classification (71) Applicant: William Marsh Rice University, (51) Int. Cl. Houston, TX (US) CI2P 7/64 (2006.01) (52) U.S. Cl. (72) Inventors: Ka-Yiu SAN, Houston, TX (US); Hui CPC ...................................... CI2P 7/649 (2013.01) WU, Houston, TX (US) USPC ........................................ 435/134:435/252.3 (73) Assignee: William Marsh Rice University, Houston, TX (US) (57) ABSTRACT (21) Appl. No.: 14/266,942 (22) Filed: May 1, 2014 Methods of using9. crude glyglvcerol to make fattvy acids are O O provided, as well as integrated methods of converting glyc Related U.S. Application Data erol waste from biodiesel production into more biodiesel. (60) Provisional application No. 61/820,929, filed on May Bacteria and other microbes engineered to produce free fatty 8, 2013. acids from glycerol are also provided. Patent Application Publication Nov. 13, 2014 Sheet 1 of 7 US 2014/0335578 A1 FIGURE A-B A 8. 3. 8 : 3. 3. 3883: 3838 23: 3:38 83: x:33:38:8 * 888 &38e gigge:8: 883: 383 8:::::::::::::::: Patent Application Publication Nov. 13, 2014 Sheet 2 of 7 US 2014/0335578 A1 Methanol & catalyst Biodiesel Trans esterification Sold to market Oil or Fats Glycerin As feedstock for other products, such as ethanol, PHA etc Metharo & catalyst Sold to market Trans- Biodiesel esterification Oil or Fats O Free fatty : Fermentation acids Carbon source (biomass feedstock) FIGURE 2 Patent Application Publication Nov. 13, 2014 Sheet 3 of 7 US 2014/0335578 A1 GwceroyC gaf gfor OHAP Glycerol is . Y. Y a s w w w . - gok R PEP NAD" + ATP as NADP'+H" + ADP AA Pyruvate --> Acetate NADH + NADP'-ANADPH + NAD": udha ; : Acety c.1 NADPH + NAD" --> NADH + NADP' l N.ADP, HCO, P. AFP -- Citrate 3-Ketoacyl-ACP NAOP AA CoA.S. ACP-SH CO+ACP Funarate CA sociate Malonyl-ACP Y. NADP cycle l - Acyl-ACP Fatty acid 3-D-Hydroxyacyl-ACP Succinate alpha-ketoglutarate CPS - NAD(P)" elongation ( Succinyl-CoA Free atty acids NAD(P)H Enoyl-ACP H.O FIGURE 3 Patent Application Publication Nov. 13, 2014 Sheet 4 of 7 US 2014/0335578 A1 Patent Application Publication Nov. 13, 2014 Sheet 5 of 7 US 2014/0335578 A1 i. : * s ags x Patent Application Publication Nov. 13, 2014 Sheet 6 of 7 US 2014/0335578 A1 US 2014/0335578 A1 Nov. 13, 2014 INTEGRATED BODESEL PROCESS 0007. A variety of oils and fats can be used to produce biodiesel. These include: PRIOR RELATED APPLICATIONS 0008 Virgin oil feedstock rapeseed and soybean oils 0001. This application claims priority to 61/820,929, are most commonly used, soybean oil accounting for titled INTEGRATED BIODIESEL PROCESS and filed May about half of U.S. production. It also can be obtained 8, 2013, and which is expressly incorporated by reference from Pongamia, field pennycress, jatropha and other herein for all purposes. crops such as mustard, jojoba, flax, Sunflower, palm oil, coconut, hemp, and the like. FEDERALLY SPONSORED RESEARCH 0009 Waste vegetable oil (WVO). STATEMENT 0.010 Animal fats including tallow, lard, yellow grease, chicken fat, and the by-products of the production of 0002. Not applicable. omega-3 fatty acids from fish oil. 0011 Algae, which can be grown using waste materials REFERENCE TO MICROFICHEAPPENDIX Such as sewage and without displacing land currently 0003) Not applicable. used for food production. 0012 Oil from halophytes, such as Salicornia bigelovii, FIELD OF THE DISCLOSURE which can be grown using saltwater in coastal areas where conventional crops cannot be grown, with yields 0004 Large quantities of glycerol are being produced in equal to the yields of soybeans and other oilseeds grown biodiesel manufacturing processes as waste. The current using freshwater irrigation. invention makes use of this glycerol to produce free fatty 0013 Sewage Sludge The sewage-to-biofuel field is acids, which can be used to produce more biodiesel without attracting interest from major companies like Waste producing added glycerol as a waste product. Management and startups like InfoSpi, which are bet ting that renewable sewage biodiesel can become com BACKGROUND OF THE DISCLOSURE petitive with petroleum diesel on price. 0005 Biodiesel is an oil- or fat-based diesel fuel consist 0014. As shown in reaction (I) above, glycerol is the major ing of long-chain alkyl esters. The National Biodiesel Board byproduct produced during the production of biodiesel from also has a technical definition of biodiesel as a mono-alkyl fat or oil. Indeed, about one pound glycerol is formed per ester. Biodiesel is typically made by chemically reacting lip every 10 pounds of biodiesel produced and global produc ids (e.g., vegetable oil or animal fat (tallow)) with an alcohol tions levels have long topped two million cubic meters of to produce fatty acid esters according to reaction (1), wherein glycerol annually (FIG. 1) resulting in a 67% price decrease triglycerides (1) are reacted with an alcohol Such as ethanol in US glycerol due to the market glut. Therefore, there is (2) to give ethyl esters of fatty acids (3) and glycerol (4): increasing interest in developing uses for the excess glyc erol—now considered a waste product rather than a valuable chemical. (I) 0015 Crude glycerol, however, is not very pure, contain ing methanol, salts, Soaps and water as the main contami nants. Concentration and presence of each contaminant will vary drastically from one industry to another, due to a variety 1N - RI of parameters, including oil source and reaction conditions. OCR O For instance, glycerol can vary from 92% to 65% in crude glycerol samples, and water can vary from 6-26%. The pres OCR22 + 3 V 1No ul R2 it ence of Such impurities in crude glycerol samples can nega OCR OH O tively impact any conversion process of this waste product. 0016 Various studies have been reported to convert waste 1 2 ul glycerol into more valuable products Such as ethanol, Succi 1No R3 nate and polyhydroxybutyrate (PHB), omega-3 polyunsatu 3 rated fatty acids, 1.3 propanediol (PDO). However, such OH methods usually require transport of crude glycerol to another facility where the conversion can take place, thus increasing costs and reducing efficiencies (see FIG. 2A). Furthermore, OH the impurities present in crude glycerol have complicated Such methods. 0017 Thus, what is needed in the art is a method of using OH the vast amounts of crude glycerol being produced annually, 4 preferably a cost efficient method that can be integrated with existing biodiesel production. 0006 Biodiesel is used in standard diesel engines and is thus distinct from the vegetable and waste oils used to fuel SUMMARY OF THE DISCLOSURE converted diesel engines. It can be used alone, or blended with 0018 Our approach for converting crude glycerol waste petrodiesel. Biodiesel can also be used as a low carbon alter product into a valuable commodity is to biologically convert native to heating oil. As such it has been an important com the glycerol into free fatty acids that can be used directly as a ponent in global efforts to reduce petroleum consumption, feedstock to produce more biodiesel (FIG. 2B). The appeal of and move towards Sustainable energy production models. this scheme is that biodiesel is the only major product, mak US 2014/0335578 A1 Nov. 13, 2014 ing the integrated biodiesel production process more effi regulatory sequences or removing repressors. However, over cient. Of course, the free fatty acids can also be sold to the expressing the gene by inclusion on selectable plasmids that market, or used as feedstocks for other chemical synthesis exist in hundreds of copies in the cell may be preferred due to reactions, as desired. its simplicity, although permanent modifications to the 0019. The steps involved in implementing the process are: genome may be preferred in the long term for stability rea 0020, 1) Engineering a microbial strain to efficiently con SOS. vert glycerol to free fatty acids. 0031. Other fatty acyl ACP thioesterases include Umbel 0021 2) Assembling a bioreactor to grow the engineered lularia Californica (GenBank #AAC49001), Cinnamomum strain to process the glycerol from a biodiesel plant. Prefer camphora (GenBank #Q39473), Umbellularia Californica ably, the reactor is at the same facility as the biodiesel pro (GenBank #Q41635), Myristica fragrams (GenBank duction facility, thus glycerol is separated from the biodiesel #AAB71729), Myristica fragrams (GenBank #AAB71730), and/or fatty acids, and fed directly to the bioreactor. Elaeisguineensis (GenBank #ABD83939), Elaeisguineensis 0022 3) Free fatty acids can be removed from the biore (GenBank #AAD42220), Populus tomentosa (GenBank actor, and fed back into the system for biodiesel production, #ABC47311), Arabidopsis thaliana (GenBank #NP or a separate reactor can convert the fatty acids to biodiesel, 172327), Arabidopsis thaliana (GenBank #CAA85387), which is then combined with biodiesel from the remaining Arabidopsis thaliana (GenBank #CAA85388), Gossypium part of the facility. Alternatively, the fatty acids can be sold as hirsutum (GenBank #Q9SQI3), Cuphea lanceolata (Gen is, or used for the synthesis of other derivatives, and the like. Bank iCAA54060), Cuphea hookeriana (GenBank 0023 The advantages of using the current system of pro #AAC72882), Cuphea calophylla subsp. mesostemon (Gen ducing free fatty acid from glycerol include: Bank #ABB71581), Cuphea lanceolata (GenBank 0024. It recycles the glycerol byproduct to form more #CAC19933), Elaeis guineensis (GenBank #AAL15645), biodiesel, which is a highly desirable product. Cuphea hookeriana (GenBank iQ39513), Gossypium hirsu 0025. Only a single product is produced, and therefore tum (GenBank #AAD01982), Vitis vinifera (GenBank the method allows implementation of a more efficient #CAN81819), Garcinia mangOStana (GenBank business model. #AAB51525), Brassica juncea (GenBank #ABI18986), 0026.
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