US010294500B2 (12 ) United States Patent ( 10 ) Patent No. : US 10 ,294 , 500 B2 Sato et al. (45 ) Date of Patent: * May 21, 2019 ( 54 ) METHOD FOR PRODUCING (58 ) Field of Classification Search METHACRYLIC ACID AND /OR ESTER None THEREOF See application file for complete search history . (71 ) Applicant: Mitsubishi Chemical Corporation , ( 56 ) References Cited Tokyo ( JP ) U . S . PATENT DOCUMENTS (72 ) Inventors: Eiji Sato , Kanagawa ( JP ) ; Michiko 8 ,241 , 877 B2 * 8 /2012 Burgard C12P 7 / 40 Yamazaki, Kanagawa ( JP ) ; Eiji 435 / 136 Nakajima, Kanagawa ( JP ) ; Fujio Yu , 8 , 501, 455 B2 8 / 2013 Gokarn et al. Kanagawa ( JP ); Toshio Fujita , 203014881 8 / 2003 DiCosimo et al. 2004 / 0076982 Al 4 / 2004 Gokarn et al . Kanagawa (JP ) ; Wataru Mizunashi, 2007 / 0184524 Al 8 / 2007 Gokarn et al . Kanagawa ( JP ) 2008 / 0076167 A1 3 / 2008 Gokarn et al. 2009 /0053783 Al 2 /2009 Gokarn et al . (73 ) Assignee : Mitsubishi Chemical Corporation , 2009 /0130729 A1 * 5 / 2009 Symes .. .. 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Date : Mar. 13 , 2014 OTHER PUBLICATIONS Office Action dated Jun . 28 , 2016 in Japanese Patent Application (65 ) Prior Publication Data No . 2013 -546110 . US 2015 /0191756 A1 Jul. 9 , 2015 Edwige J . F . Souleyre, et al ., " An alcohol acyl transferase from apple (cv . Royal Gala ) , MPAAT1 , produces esters involved in apple ( 30 ) Foreign Application Priority Data fruit flavor ” , FEBS Journal, vol. 272, No . 12 , 2005 , pp . 3132 -3144 . Sep . 10 , 2012 ( JP ) 2012 - 198840 (Continued ) Sep . 10 , 2012 ( JP ) . 2012 - 198841 Primary Examiner — Suzanne M Noakes Jan . 31 , 2013 ( JP ) 2013 -016947 ( 74 ) Attorney , Agent, or Firm — Oblon , McClelland , Jul. 30 , 2013 ( JP ) . .. .. 2013 - 157306 Aug . 1 , 2013 ( JP ) 2013 - 160300 Maier & Neustadt, L .L . P . Aug . 1 , 2013 ( JP ) .. .. .. .. 2013 - 160301 (57 ) ABSTRACT Aug . 20 , 2013 ( JP ) . .. .. .. .. .. 2013 - 170404 To provide a method for directly and efficiently producing ( 51 ) Int. Cl. methacrylic acid in a single step from renewable raw mate C12P 7 /62 ( 2006 .01 ) rials and / or biomass arising from the utilization of the C12N 9 / 10 ( 2006 . 01 ) renewable raw materials . Further provided is a method for C12N 9 /00 ( 2006 . 01 ) producing methacrylic acid using microbes having the abil C07C 57 / 04 ( 2006 . 01 ) ity to produce methacrylic acid , from renewable raw mate C07C 69 /54 ( 2006 . 01 ) rials and / or biomass arising from the utilization of the C12P 7740 ( 2006 . 01 ) renewable raw materials , as a carbon source and / or energy C12N 9 / 02 ( 2006 .01 ) source . The method for producing methacrylic acid enables (52 ) U . S . CI. methacrylic acid to be safely and easily produced from CPC . .. C12P 7762 ( 2013 .01 ) ; C07C 57 /04 biomass , without using petroleum - derived raw materials , by ( 2013 . 01 ) ; C07C 69 / 54 (2013 .01 ) ; C12N 9 /001 utilizing microbes having the ability to produce methacrylic ( 2013 .01 ) ; C12N 9 / 1029 (2013 . 01) ; C12P 7 /40 acid . (2013 .01 ) ; C12Y 103 /99 (2013 .01 ) ; C12Y 103 / 99003 (2013 . 01) ; C12Y 203 /01084 5 Claims, 7 Drawing Sheets ( 2013 .01 ) Specification includes a Sequence Listing . US 10 ,294 ,500 B2 Page 2 References Cited Database UniProt [ online ] , Accession No . G2UBR1, Definition : ( 56 ) Probable acyl - CoA dehydrogenase, http : // www . uniprot . org / uniprot / GRUBR1, Nov . 16 , 2011 uploaded [retrieved Nov . 27 , 2013 ], pp . FOREIGN PATENT DOCUMENTS 1 - 3 Database UniProt [online ], Accession No . 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