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WO 2016/057676 Al 14 April 2016 (14.04.2016) P O P C T

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WO 2016/057676 Al 14 April 2016 (14.04.2016) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2016/057676 Al 14 April 2016 (14.04.2016) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C07D 307/56 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/US20 15/054504 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, 7 October 2015 (07. 10.2015) KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, (25) Filing Language: English PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, (26) Publication Language: English SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: 62/061,828 October 2014 (09. 10.2014) US (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (71) Applicant: BP CORPORATION NORTH AMERICA GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, INC. [US/US]; 501 Westlake Park Boulevard, Houston, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TX 77079 (US). TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (72) Inventors: ADAMIAN, Victor, A.; 150 W . Warrenville LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, Road, Mc 200- lw, Naperville, IL 60563 (US). BINDER, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, Joseph, B.; 150 W. Warrenville Road, Mc 200- lw, GW, KM, ML, MR, NE, SN, TD, TG). Naperville, IL 60563 (US). SHEA, Ryan; 150 W. Warren ville Road, Mc 200- lw, Naperville, IL 60563 (US). Published: (74) Agent: FUZAIL, Kalim; BP America Inc., 150 W. War — with international search report (Art. 21(3)) renville Road, MC 200- 1W, Naperville, IL 60563 (US). (54) Title: USE OF CARBOXYLIC ACIDS IN THE PRODUCTION OF 2,5-FURANDICARBOXYLIC ACID FIG. o 0 80 i SO- K! ?o ! 7 - 80 © 0-80 - D ft 3 4 2 · s 10 0 Water {v ! } © v (57) Abstract: Methods for providing effective, efficient and convenient ways of producing 2-5-furandicarboxylic acid are presen o ted. In addition, compositions of 2-5-furandicarboxylic acid including 2-5-furandicarboxylic acid, and at toast one byproduct are preserved, in some aspects, 4-deoxy-S-dehydroglucaric acid is dehydrated to obtain the 2-5-furandicarboxylic acid, A solvents cata o lyst, and/or reactant may he combined with the 4-deoxy-S-dehydroglucaric acid to produce a reaction product Including the 2-5- furandicarboxylic acid. In some arrangements, the reaction product may additionally include water and/or byproducts. USE 0 ? A X ¥ ! N THE PRODUCTION ,S F U A M D IC AC:O> S EF E E (¾0 0 J This application claims benefit of provisional application Serial No, filed. October % 2014, and llt 4 of. ¾r x>x !i Adds in the Production : ¾ ¾» Acid " which s hereby incorporated herein by reference in ts entirety BACKGROUND .0002] 2 5 &ra diear oxyl e acid (FDCA)- and FDCA esters a recognized potential intermediates n numerous chemical fields. For instance, FDCA is idendfied a prospective precursor in the prod ctlo of plasties, fuel, polymer aterials p arnn tiea s agricultural chemicals and enhancers of comestibles, others. Moreover, FDCAs ar highlighted by the U.S. Department of Energ as a priority chemical for developing future m SUMMARY Th following presents a simplified in order to provide a basic understanding of some aspects of i disclosure. The summary is not an extensive overview of the di io rre. t is neither intended to identify key or c dea! elements of the diseiosare nor to delineate the scope of the disclosure. The following summar presents some concepts of the disclosure in. a simplified for as a prelude to description below, [0004] Aspects of the disclosure provide effective, efficient, an convenient ways of prod r n g 2 S rand carbo yite acid (FDCA), In particular, certain aspects of th disclosure provide techniques for dehydrating 4 de x -S dehy rogluear e acid (DDG) to obtai FDCA, The dehydration reaction proceeds by combining one or .more catalysts and/or one or m r solvents with a DDG starling material I some instances, the catalyst a act as a dehydrating agent and may interact with hydroxy! poops on t h DDG thereby encouraging elimination reactions to form FDCA, The catalyst and/or solvents may assist the dehydration reaction thereby producing increased yields of FDCA. [ 05] n a . first embodiment, a method of producing .FDCA includes t g g DD into contact with a solvent in the presence of a catalyst ie,g. combining DDG, a solvent, and a catalyst in a reactor), wherein the catalyst s selected from the group consisting of a bromide sa t, a ydrob ie ¾ elemental br la ,. c o ami. allowing D.DO to to produce DCA y water. t I other embodiments a method of producing FDCA includes bringing DD int contact a solvent i th presence of catalyst (e,g. s combining DG, a and a catalyst n a reactor) wherein th catalyst is selected fc a the group consisting of a ahde salt, a I drohah acid, elemental on, and combinations thereof, and allowi DDG to react t produce FDCA, any byproducts, and water, | I 7| I another embodiment a method of producing FDCA includes bringing DDG into contact with acidic solvent n th presence of water, and allowing DDG, the acidic solvent, and water t react with each other produce FDCA, any bypro cts, and water. n some embodiments, a method of producing FDCA Includes bringing DDG into contact w th a carboxylic aeid and allowing DDG an the eatboxyiic acid to react with each other to produce FDCA. any byproducts, and water. [ \ These features, along wi t n oth rs are discussed n greater detail below B BF D PT OF THE DRAWINGS The present disclosure s illustrated by way of example and not limited n t e accompanying figures n which ke fe numerals indicate similar elements and which; P J FIG. I Illustrates graph that depicts th benefit of using water with an acidic solvent according to one or more embodiments DETAILED DESCRIPTION 2| Various examples, aspects, and embo ments of the subject matter disclosed here are possible and will be apparent to the person of ordinary skill n the art, given the benefit of this disclosure. In this disclosure reference to eer m exemplary embodiments" or aspects (and similar phrases) eans that those embodiments or aspects are merely non-limiting examples of the subject matter and tha there likely are other alternative e bodim o s or aspects which are not excluded. Unless otherwise indicated o unless otherwise clear from the context in which t is described, alternative elements or features the d and examples belo and in the Summary above are interchangeable with each other. An element described in one example may be interchanged or subst uted for one or n corresponding elements described in another example, Similarly, optional o n n esse i ai features disclosed connection with a particular end i ent o example hould be understood to be disclosed for use i a other embodiment of the disclosed subject matter. More generally, the elements of the examples should be understood to be disclosed generally fo use with oilier aspects and of e products a d methods disclosed herein. A reference to a component o Ingredient being operative, i.e., able to perform o e or more fractions, tasks and/or operations or t e like, Is intended to that it can perform the expressly recited n e ion s), task(s) and/or perailou s ia at least certain em odi err s and may wel be operat e t perform also one or ore other fo neti , tasks and r operations. While th s disclosure Includes specific examples, including presently preferred modes or embodiments, those skilled in the art will appreciate thai there are numerous variations and modifications: within th spirit and scope of the Invention as set forth. di appe de claims. Bach word and phrase used in the claims i intended to include al ts dictionary meanings consistent with ts usage in th disclosure aud/ t with its technical and industry usag n ay relevant technology area. Indefinite articles, such as "a," and and the definite article " " and other such words and phrases are used i the claims in the usual a d traditional way in patents , to mean "at least " or "on or more." The word "comprising" is use in the claims to have its traditional, open-ended meaning, that is, to ea that the product or process defined by d e claim may optionally also have additional features, elements, steps, etc beyond those expressly recited. e dr reaction of o F CA [ )0 14 The present invention s directed to ,S d subs tuted furans (which ay include, e.g., FDCA) b the dehydration of oxidized sugar products (which ma include, e.g., DDG), In accordance with some aspects of fo invention, th dehydration methods produce higher yields and/or higher purit 2,5 di tiiuted furans than previously known dehydra tion reactions.
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