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(12) United States Patent (10) Patent No.: US 9,139,501 B2 Gastaldo Et Al

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(12) United States Patent (10) Patent No.: US 9,139,501 B2 Gastaldo Et Al US0091395O1B2 (12) United States Patent (10) Patent No.: US 9,139,501 B2 Gastaldo et al. (45) Date of Patent: Sep. 22, 2015 (54) CONTINUOUS PROCESS FOR CONVERSION 2010/0304439 A1 12/2010 Medoff OF LIGNIN TO USEFUL COMPOUNDS 2010/0304440 A1 12/2010 Medoff 2012/0172579 A1 7/2012 Qiao et al. (71) Applicant: Chemtex Italia, S.p.A., Tortona (IT) 2013/0313472 A1* 11/2013 Torre et al. ............... 252/183.11 9 AV evez Kes (72) Inventors: Dan Gastaldo, Middleburg Heights, OH FOREIGN PATENT DOCUMENTS (US); Steven Ryba, Wadsworth, OH WO 2011/061400 A1 5, 2011 (US); Aaron Murray, Chardon, OH WO 2011, 117705 A2 9, 2011 (US); Guliz Arf Elliott, Northfield WO 2012, 174429 A1 12/2012 Center, OH (US) WO 2013/01 1206 A1 1/2013 OTHER PUBLICATIONS (73) Assignee: Biochemtex, S.p.A., Tortona (AL) (IT) “KOV piston pumps with ball valves for high-pressure slurry pump (*) Notice: Subject to any disclaimer, the term of this ing”. Putzmeister, Jan. 1, 2010, pp. 47-1. patent is extended or adjusted under 35 Parveen Kumar et al., “Methods for Pretreatment of Lignocellulosic Biomass for Efficient Hydrolysis and Biofuel Production', Industrial U.S.C. 154(b) by 0 days. & Engineering Chemistry Research, Apr. 15, 2009, pp. 3713-3729, vol. 48, No. 8, American Chemical Society, US. (21) Appl. No.: 13/775,230 Xingyu Wang et al., “Exploiting H-transfer reactions with RANEY Ni for upgrade of phenolic and aromatic biorefinery feeds under (22) Filed: Feb. 24, 2013 unusual, low-severity conditions'. Energy & Environmental Science, Jan. 1, 2012, p. 8244, vol. 5, No. 8. (65) Prior Publication Data Kirk D.F. et al., “Gravity Concentration', Kirk-Othmer Encyclope dia of Chemical Technology, Jan. 1, 1980, pp. 1-29, vol. 12, John US 2014/OO9683O A1 Apr. 10, 2014 Wiley & Sons, New York, U.S. DeJongh & RPPRIJSJA, “Pump Design”, Arakis, Mar. 1, 2004, pp. Related U.S. Application Data 1-45. Monavariet al., “The influence of Solid/liquid separation techniques (60) Provisional application No. 61/603.217, filed on Feb. on the Sugar yield in two-step dilute acid hydrolysis of Softwood 24, 2012, provisional application No. 61/719,486, followed by enzymatic hydrolysis'. Biotechnology for Biofuels, filed on Oct. 28, 2012, provisional application No. Mar, 16, 2009, pp. 1-9, 2:6. 61/751,919, filed on Jan. 13, 2013, provisional Kantarci et al., “Bubble column reactors'. Process Biochemistry, Epists. No l CS 'E,s sth f “Valves2005, pp. for 2263-2283, Slurry Transport vol. 40, ElsevierEngineered Ltd. Solutions for the Mining proV1S1onal appl1cauon No. s , Illed on Feb. and Minerals Industry”, MOGAS Severe Service Ball Valves, Jun. 15, 2013. 2011, pp. 1-20. Fernando et al., “Lignin recovery from spent liquors from ethanol (51) Int. Cl. water fractionation of Sugar cane bagasse'. Cellulose Chemistry and CSK 3/04 (2006.01) Technology, 2010, pp. 311-318, vol. 44, No. 9. C07C37/54 (2006.01) Huber, George W. “Synthesis of Transportation Fuels from Biomass: F5D I/00 (2006.01) Chemistry, Catalysts, and Engineering”, Jan. 2006, pp. 4044-4098, CD7C4I/OI (2006.01) University of Massachusetts—Amherst. (52) U.S. Cl. * cited b CPC ................. C07C37/54 (2013.01); C07C4I/01 cited by examiner (2013.01); F15D '93939, G Primary Examiner — Mark Shibuya (58) Field of Classification Search Assistant Examiner - Sonya Wright CPC CO8K 5/04 (74) Attorney, Agent, or Firm — Edwin A. Sisson, Attorney USPC .......................................................... 524/170 at Law, LLC See application file for complete search history. (57) ABSTRACT 56 References Cited This specificationp discloses an onerationalp continuous ppro cess to convert lignin as found in ligno-cellulosic biomass U.S. PATENT DOCUMENTS before or after converting at least some of the carbohydrates. 1,628, 190 A 5/1927 Raney The continuous process has been demonstrated to create a 2,146,655 A 2f1939 Sherrard et al. slurry comprised of lignin, raise the slurry comprised of lig 2,813,090 A 11, 1957 Ba11 nin to ultra-high pressure, deoxygenate the lignin in alignin 2.947,739 A 8, 1960 Gaslini et al. conversion reactor over a catalyst which is not a fixed bed 4.420,644 A 12/1983 Huibers et al. without producing char. The conversion products of the car 7,960,598 B2 6/2011 Spilker et al. 8,735,544 B1 5, 2014 Prevost et al. bohydrates or lignin can be further processed into polyester 2009/0098617 A1 4/2009 Burke et al. intermediates for use in polyester preforms and bottles. 2009,0192268 A1 7/2009 Talkowski 2010.0137665 A1 6, 2010 Chen 20 Claims, 9 Drawing Sheets U.S. Patent Sep. 22 2015 Sheet 1 of 9 US 9, 139,501 B2 X1 008 |EdO?X-18º95 ! unºr, U.S. Patent Sep. 22, 2015 Sheet 2 of 9 US 9,139,501 B2 X1804UO|SJ0\u00 008 Z*OIH |EdO?X-188503 U.S. Patent Sep. 22 2015 Sheet 3 of 9 US 9,139 501 B2 |EdO?X-18803 £"OHH U.S. Patent Sep. 22, 2015 Sheet 4 of 9 US 9,139,501 B2 80 FIG. 4 U.S. Patent Sep. 22, 2015 Sheet 5 Of 9 US 9,139,501 B2 %06 %08 uOSuedSIO ele|duo) hueojed U.S. Patent Sep. 22, 2015 Sheet 6 of 9 US 9,139,501 B2 U.S. Patent Sep. 22, 2015 Sheet 7 Of 9 US 9,139,501 B2 U.S. Patent Sep. 22, 2015 Sheet 8 of 9 US 9,139,501 B2 520 SSSSSSSSSSN 1530 50 FIGURE 8 U.S. Patent Sep. 22, 2015 Sheet 9 Of 9 US 9,139,501 B2 u f O US 9,139,501 B2 1. 2 CONTINUOUS PROCESS FOR CONVERSION tinuous process. For example, the disclosure states that “m OF LIGNIN TO USEFUL COMPOUNDS aterials of a continuous process must be capable of being transported from a low pressure source into the reaction Zone, PRIORITY AND CROSS REFERENCES and products must be capable of being transported from the reaction Zone to the product recovery Zone. Depending upon This application claims the priority of U.S. Provisional the mode of operation, residual solids, if any, must be capable Patent Application No. 61/603.217 filed 24 Feb. 2012, U.S. of being removed from the reaction Zone.” This discloses the Provisional Patent Application No. 61/719,486 filed 28 Oct. intuitively obvious requirement to operate a continuous pro 2012, U.S. Provisional Patent Application No. 61/751,919 cess but the statement fails to teach one of ordinary skill how filed 13 Jan. 2013, U.S. Provisional Patent Application No. 10 to achieve those requirements. Nowhere in the application is 61/764,611 filed 14 Feb. 2013, U.S. Provisional Patent Appli this essential problem discussed or solved. In fact, during the cation No. 61/765,402 filed 15 Feb. 2013, and WIPO Appli cation No. PCT/US2013/027393 the teachings of all of which discussion of FIG. 2 of the publication, the temperature and are incorporated in their entirety. pressure conditions are discussed without any disclosure as to 15 how the slurry can be raised to the listed pressure of 1800 BACKGROUND psig, or even 200 psig. When considering the transport prob lem, which, as of 2006, has existed since the oil embargo of The conversion of lignin in batch processes using hydrogen 1973, a disclosure telling one of ordinary skill that transport and catalysts is known. For example, Boocock, D. G. Bet al. of materials is critical can hardly be considered enabling. “The Production of Synthetic Organic Liquids from Wood These series of applications also disclose to keep the water Using a Modified Nickel Catalyst’ discloses exposing air in the reaction Zone in the liquid phase. In the batch autoclave dried poplar to hydrogen and Raney Nickel in a batch auto this occurs due to the sealed nature. However, it fails to clave at 340° C. to 350° C. for 1 or 2 h to produce “oil disclose how this is done, or even if it can be done, in a products’. However, according to Boococket al., “the use of continuous process. Raney nickel has now been abandoned in favour of nickel 25 In order to avoid the problems of pumping and charging as from nickel salts . noted, but not solved, in the above applications and publica The use of catalysts to recover lignin is also known. ZakZ tions, dissolution of the lignin is proposed. WO 2011/117705 eski, Pieter C. etal; “The Catalytic Valorization of Lignin for relies upon dissolving the lignin so that the material can be the Production of Renewable Chemicals”, 2010 is a compre charged as a liquid taking full advantage of the check valve hensive review of catalytic efforts to convert lignin. 30 and high pressure liquid charging systems. In fact, according While many have proposed theoretical continuous pro cesses, the inventors are not aware of any disclosure which is to WO 2011/117705, “the only limit is that the lignin fed to enabling beyond a theoretical basis. For example, converting the hydrogenolysis reaction is well dissolved, at the feeding Solid lignin presents significant handling problems as docu temperature, in said solvent.” mented in PNNL-16079, September 2006. 35 There exists therefore the need for a properly enabling "High-pressure feeding systems for biomass slurries have disclosure of how to continuously convert lignin which been recognized as a process development issue at least includes the handling, charging, and essential conditions for as long as the modern biomass conversion systems have the process to be carried out. These conditions and steps are been under development since the Arab oil embargo of believed both novel and inventive and for the first time experi 1973.
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