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(12) Patent Application Publication (10) Pub. No.: US 2017/0015614 A1 ORAZOV Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2017/0015614 A1 ORAZOV Et Al US 2017.0015614A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2017/0015614 A1 ORAZOV et al. (43) Pub. Date: Jan. 19, 2017 (54) PRODUCTION OF ALPHA-HYDROXY Publication Classification CARBOXYLIC AIDS AND ESTERS FROM (51) Int. Cl. HIGHER SUGARS USING TANDEMI C07C 67/00 (2006.01) CATALYST SYSTEMS C07C 51/00 (2006.01) (71) Applicant: CALIFORNLA INSTITUTE OF (52) U.S. Cl. TECHNOLOGY, PASADENA, CA CPC ............... C07C 67/00 (2013.01); C07C 51/00 (US) (2013.01) (72) Inventors: MARAT ORAZOV, PASADENA, CA (57) ABSTRACT (US); MARK E. DAVIS, PASADENA, The present disclosure is directed to methods and compo CA (US) sition used in the preparation of alpha-hydroxy carboxylic acids and esters from higher Sugars using a tandem catalyst (21) Appl. No.: 15/207,822 system comprising retro-aldol catalysts and Lewis acid catalysts. In some embodiments, these alpha-hydroxy car (22) Filed: Jul. 12, 2016 boxylic acids may be prepared from pentoses and hexoses. The retro-aldol and Lewis catalysts may be characterized by Related U.S. Application Data their respective ability to catalyze a 12-carbon shift reaction (60) Provisional application No. 62/194,069, filed on Jul. and a 1.2-hydride shift reaction on an aldose or ketose 17, 2015. substrate. Patent Application Publication Jan. 19, 2017. Sheet 1 of 13 US 2017/0015614 A1 FIG. 1 O O O- OH OH, -N-O -A GA O l OH O ...A FIG. 2 QH 2 r OH O s --s. O ro 2-hydroxy-3-biterrois acid OH Aidotetrose t - ". -- { f ^ gas Ho-2 O Obi Sycolaideyde 2,3-dihysioxytsiataxic acic 3- Q { Giyoxa KY, w Y. O gy{{ i &is Patent Application Publication Jan. 19, 2017. Sheet 2 of 13 US 2017/0015614 A1 FIG. 3 {- O io us -- e {} - Aicisexisse -----OH OH Ho r r > QH-OH Otis a OH OH s {SA Keithexose FIG. 4 in Qi; r . (3 exege.: r (3: 3-M-r35 ^2-'-- \ i Yol --s its O. : s 5-Hydroxymethylf rural Aitchexose Kettslexese Ns: . s s os -' s & fig a r -Nso -Ns' Oilw lu e't 2-C-(hydroxymetiyl)-aidepentose Gycelaidehyde Eihydroxyacetose i {s ig Y. m . -as-a- sity 1. x Y s f SYl "Y-2 wwry sevey R Pyruvaldehycie Aliyi sciate Adetetrose Glyceraldehyde theniacets A Ny C stadi Cs products | by-products Patent Application Publication Jan. 19, 2017. Sheet 3 of 13 US 2017/0015614 A1 FIG. 5 HO O O O O OH sm wner R R2 R. R. R R2 FIG. 6 C - '' h s' \ i C s t se Y. O Y s h {i : 'chiot t :-3- D-Fructose D-arameiose A/YA \\ s \/\/ / 2Yay.' W s' \ y x \\ C 2. s -: ^ s vy is a C-C- - i is ''/ s *- HCHC s HHC C}-l. at 0:8 -Sorbose D- agatose Psicose Patent Application Publication Jan. 19, 2017. Sheet 4 of 13 US 2017/0015614 A1 FIG. 8 fictose N kill. Ju scies: Starticiaci &xavaMaxxxxxaasaxxxxsar Patent Application Publication Jan. 19, 2017. Sheet 5 of 13 US 2017/0015614 A1 FIG. 9 Scase &actics: Fractity J - UU U. was www.swax'Yaa'ss M U VAwo- U FIG. 10 Secse Reacts Factioi Soisse Stasia: Patent Application Publication Jan. 19, 2017. Sheet 6 of 13 US 2017/0015614 A1 FIG. 11 Psicosef Bia; 3-O-hydroxytet:y-atticestesse Raascist assics: OA 2-C-hydroxymethy airiopertos: Psilasa Statixia. 5.4 5.2 ssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssss-xxx-xxxxx'sssssssssss-Xxxxx-x-xx-xx-xx-xxxx5.0 4.8 4.6 44 42 4.0 3.8 3.6 3.4 FIG. 12 agakose eactics Fascist -l -u. ------ & S& Stadiatri www.wyww. xxxxxww.xxxxwww.xxwww.www.www --M.-------M.--a-M' xywww. agatase Stacia: 9.65 9.55 4.95 4.is 4,0s. 3.95 3.85 3.75 3.65 3.5s 3.45 (ppt) Patent Application Publication Jan. 19, 2017. Sheet 7 of 13 US 2017/0015614 A1 FIG. 13 Siara: seiose See actii A. S. --- ra MW-ta.-- 3 x3- V Safe: sease Stassistic FIG. p : 3,5 N N waaaaaaaaaaaaaa. XXXAXWAXXXWWAXX'. a.k. Aaasa y Y-w ask-WkamskWsksaaxas-XaXmasa Aax&XMXaa-XXX-X p: s ,S sassssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssssss Patent Application Publication Jan. 19, 2017. Sheet 8 of 13 US 2017/0015614 A1 FIG. 15 --- wo--~ to SO, % SO, SO%. A. AO: i 30% is 2% 10% % : - O O 3C 4. St. Patent Application Publication Jan. 19, 2017. Sheet 9 of 13 US 2017/0015614 A1 FIG. 17 3% 70% 60% 50% 40% 30% 20% i --5 mg Mod, 0% : --20 mg Moo, --80 mg Moo, %, ........................arr war rrrr r < r n x < r n > Y r n w w arr warr w w arr r s rar r s a rrrr rrrr "........................................... { i 2O 3. &O S Time, h 70% 60% : s 40% is 0% --50 mg Sn-MF O% - N -100 mg Sr-MF -r-200 Big Sr-MF % ----------------------------------------------------------------------------------------------------------------- O 3. s Time, h Patent Application Publication Jan. 19, 2017. Sheet 10 of 13 US 2017/0015614 A1 FIG. 19 8% - 70% 80% St: . 4% 30% 20% : 10% - see a yi , P. r war as yt & F O% ----------------- ------------------------- ------------------------ s FIG. 20 O. : 80% 70% 60% -0-80 mg Mo03, iOO ng Sn-MF, F --80 mg MoQs, Ong Si-viri, F 40% - -- 0 mg MoOs, OO ng Sn-viFi, 3. % -- 80 mg Moos, O mg Sn-viri, GAfi A % - texx 0 mg Mo.Os, OO ring Sn-viri, GAfDA O%. , Patent Application Publication Jan. 19, 2017. Sheet 11 of 13 US 2017/0015614 A1 FIG. 21 re s s e s and s * ii. o alth a MOO2 O% her -3PMos2O4. % 2 30 4: O Time, h FIG. 22 88. --80 mg Moos & - -20 mg Ni(N,N,N',N'-Meen, Cl, 70% --2 mg NiN,N,N',N'-Meen),c, so to 200mg Torp. m e Six six w s 3: ar 23 & Patent Application Publication Jan. 19, 2017. Sheet 12 of 13 US 2017/0015614 A1 FIG. 23 93% ...; : . 80% : -0-80 mg MoC3, 50 mg Sn-Beta, F p 8. wn 80 mg Mo.O.s, 50 mg Sn-MF, F 60% : ---80 mg MoOs, 50 mg Sn-Beta, G - ), 50 mg Sn-Beta, DHA 30% 10% % FIG. 24 9% - 80% 70% A- w w a a a we w a a as a w w a i. 60% 50% 30% worritose 20% ow Psicose or rainaeiose 10% K. Sorose ---agatose % ye. ----------:------------- Patent Application Publication Jan. 19, 2017. Sheet 13 of 13 US 2017/0015614 A1 FIG. 25 80%, 70% is 60% --Ethanoi SO% --Methano 540% ----90 wt.% Ethanol, 10 wit% Water - ) . Water 30% O O....... ''''''''' 20% ---- as in a r er r * 1 stA 10% - O% ------------------------------------------------------------- ----------------------------------------------------- O O 30 40 SO Time, h FIG. 26 16 14 12 10 8 2 --Batch 50 mg at t = Oh) --Semibatch (50 mg at t = Oh and 50 mg atts: 20 h. O 18) 2O 3O 40 SO Time, h US 2017/0015614 A1 Jan. 19, 2017 PRODUCTION OF ALPHA-HYDROXY 0009. The carbohydrate feedstock includes any cellulosic CARBOXYLIC AIDS AND ESTERS FROM and hemicellulosic biomass material, either as-provided or HIGHER SUGARS USING TANDEMI partially or completely hydrolyzed to its constituent oligo-, CATALYST SYSTEMS di-, or monosaccharides. In preferred embodiments, the feedstock is characterized as comprising at least one pentose CROSS REFERENCE TO RELATED or hexose monosaccharide. In other embodiments, the car APPLICATIONS bohydrate feedstock is characterized as comprising at least one aldose or ketose monosaccharide. Glucose, mannose, 0001. This application claims the benefit of priority from fructose, and Xylose are only some of the materials useful in U.S. Patent Application No. 62/194,069, filed Jul. 17, 2015, these disclosed methods. the contents of which are incorporated by reference herein 0010. These first and second catalysts may be described for all purposes. either functionally or chemically, or in both functional and chemical terms, and all of Such descriptions are considered GOVERNMENT RIGHTS within the scope of the present disclosure. 0002 This invention was made with government support 0011. In some embodiments, the retro-aldol catalyst is under Grant No. DE-SC000 1004/T-108118 awarded by the described as a material capable of performing the 12-carbon Department of Energy. The government has certain rights in shift reaction on an aldose or ketose Substrate, i.e.: the invention. TECHNICAL FIELD HO O V OH 0003. This application is related to the formation of alpha-hydroxy carboxylic acids and esters and intermediates R R R. R. from higher Sugars. 0012 where R is a carbohydrate chain, and R is H or BACKGROUND CHOH. Such a capability may be independently observed 0004 Chemocatalytic routes for the production of C-hy in the absence of the second Lewis acid catalyst. In other droxy carboxylic acids (e.g. lactic acid, 2-hydroxy-3- embodiments, the first retro-aldol catalyst may also be butenoic acid, 2,4-dihydroxybutanoic acid, and glycolic described as capable of converting a pentose or hexose acid) from biomass-derived Sugars have been extensively monosaccharide to a diose, triose, or tetrose intermediate, studied in the recent years, as these acids, their esters, and with the elimination of glycolaldehyde or glyceraldehyde lactones have been recognized to hold large potential as (see, e.g., FIGS. 1-4). In still other embodiments, the first renewable, green platform chemicals for a number of indus retro-aldol catalyst is capable of effecting the 12-intramo tries (e.g. polymers, solvents, and fine chemicals). lecular carbon shift reaction of the pentose/hexose and is 0005 Considerable progress has been made on the pro also capable of effecting retro-aldol reactions to as to form duction of lactic acid and alkyl-lactates from trioses (glyc a dioseftriose?tetrose intermediate.
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