THOMUTLULUTTUS009822321B2 (12 ) United States Patent ( 10 ) Patent No. : US 9 ,822 , 321 B2 Rantanen -Kolehmainen et al. ( 45 ) Date of Patent : Nov . 21 , 2017 ( 54 ) GASOLINE COMPOSITIONS AND METHOD ( 56 ) References Cited OF PRODUCING THE SAME U . S . PATENT DOCUMENTS ( 71 ) Applicant : NESTE OIL OYJ, Espoo (FI ) 4 ,398 , 921 A 8 / 1983 Rifkin et al. ( 72 ) Inventors : Leena Rantanen -Kolehmainen , Porvoo 6 , 113 , 661 A 9 /2000 Germanaud et al. (FI ) ; Päivi Aakko - Saksa , Porvoo (FI ) ( Continued ) ( 73 ) Assignee : NESTE OYJ, Espoo (FI ) FOREIGN PATENT DOCUMENTS DE 102010017818 AL 8 / 2011 ( * ) Notice : Subject to any disclaimer, the term of this EP 1 900 794 A2 3 /2008 patent is extended or adjusted under 35 (Continued ) U . S . C . 154 ( b ) by 91 days. OTHER PUBLICATIONS (21 ) Appl. No. : 14 /572 , 860 Bielansky P et al : “ Catalytic cracking of rapeseed oil to high octane gasoline and olefins” , Chemical Engineering and Processing, ( 22 ) Filed : Dec . 17 , 2014 Elsevier Seuoia , Lausanne, CH , vol . 49 , No. 8 , Aug . 1 , 2010 . (65 65 ) Prior Publication Data ( Continued ) US 2015 / 0144087 A1 May 28, 2015 Primary Examiner — Long T Tran (74 ) Attorney, Agent, or Firm — Buchanan Ingersoll & ( 30 ) Foreign Application Priority Data Rooney PC (57 ) ABSTRACT Sep . 11, 2011 (FI ) .. .. 20110300 Gasoline fuel and method of making and using it . The fuel comprises from 5 to 20 vol. - % paraffinic hydrocarbons ( 51) Int. Ci. originating from biological oils, fats , or derivatives or com CIOL 10 / 02 (2006 . 01) binations thereof. Further, it comprises oxygenates , such as F02B 43 /02 ( 2006 . 01 ) ethanol present in a concentration of about 5 to 15 vol .- % ; (Continued ) or iso - butanol present in a concentration of 5 to 20 vol. - % , ( 52 ) U .S . CI. preferably about 10 to 17 vol. - % ; or ETBE present in a ??? . .. .. .. .. CIOL 10 / 02 ( 2013 .01 ) ; C10G 3 / 52 concentration of 7 to 25 vol. - % , preferably about 15 to 22 (2013 . 01 ) ; C10G 45 / 58 ( 2013 .01 ) ; C10G vol. - % . The bioenergy content of the gasoline is at least 14 47 /00 ( 2013 .01 ) ; Energy equivalent percentage (Eeg - % ) calculated based on (Continued ) the heating values given in the European Renewable Energy (58 ) Field of Classification Search Directive 2009 /28 / EC . By means of the invention , fuels with CPC .. .. YO2P 30 / 20 ; YO2P 30 /42 ; YO2P 30 / 446 ; a high bioenergy content are provided which can be used in C10G 2300 / 1011 ; C10G 1 / 002 ; conventional gasoline - fuelled automotive engines. (Continued ) 4 Claims, 3 Drawing Sheets European test at - 7 °C 0 . 020 - European test at - 7 °C MPF * MPFI AFSI 0 .018 A FSI OFFV O 0 .016 OFFV A A 0 . 014 AAAA Euro 5 limit at - 7 °C 0 . 012 A HC(g/km) PM(g/km) 0. 010 0 . 008 O Euro 5 limit at O 0. 006 nomai temp. 0 . 004 0 0. 5 A 00 og modno 0 . 002 0 ,0 17 Euro 5 limit at normal temp- - . - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 0 .000 0 .0 2 . 0 4 . 0 6 .0 8 .0 10 . 0 12 .0 14 . 0 0 .00 0 . 02 0 . 04 0 . 06 0 .08 0 . 10 0 . 12 CO ( g / km ) NOx ( g / km ) US 9 ,822 , 321 B2 Page 2 ( 51 ) Int. Cl. 2010 /0077655 A1 4 /2010 Bauldreay et al . CIOL 1 / 185 ( 2006 .01 ) 2010 / 0131247 A15 / 2010 Carpenter et al. 2010 / 0275509 A1 11/ 2010 Sakuma et al. C10L 1 / 182 ( 2006 .01 ) 2011 /0015459 AL 1 / 2011 Aalto et al . CIOL 1/ 06 ( 2006 .01 ) 2011 / 0076732 A 3 / 2011 Dumenil et al . C10G 45 / 58 ( 2006 . 01 ) 2011/ 0126449 A1 * 6 / 2011 Xu . .. CIOL 1 / 1616 C10G 47 / 00 ( 2006 .01 ) 44 / 308 C10G 65 / 12 ( 2006 . 01 ) 2011/ 0138681 A1 6 / 2011 Ramirez Corredores et al . 2012/ 0151828 A1* 6 / 2012 Kalnes . .. .. .. CIOL 1/ 00 C10G 3 / 00 ( 2006 . 01 ) 44 /308 CI0G 69/ 02 ( 2006 .01 ) 2012 /0152801 A1 * 6 /2012 Bozzano .. .. .. .. .. CIOG 2 /30 CIOL 1 / 10 ( 2006 . 01 ) 208 / 17 C10L 10 / 10 ( 2006 . 01 ) ( 52 ) U . S . CI. FOREIGN PATENT DOCUMENTS CPC C10G 65 / 12 ( 2013 .01 ) ; C10G 69 / 02 ( 2013 .01 ) ; C10L 1 / 06 ( 2013 .01 ) ; C10L 1 / 10 EP 2177587 AL 4 /2010 EP 2290035 A1 3 / 2011 ( 2013 .01 ) ; CIOL 1 / 182 ( 2013 . 01 ) ; CIOL JP A - 2007 - 270039 10 / 2007 1 / 1852 (2013 . 01 ) ; CIOL 10 / 10 (2013 .01 ) ; WO WO 2004022674 AL 3 / 2004 F02B 43 / 02 ( 2013 .01 ) ; CIOG 2300 / 1011 ( 2013 . 01 ) ; CIOG 2300 / 1014 ( 2013 .01 ) ; CIOG OTHER PUBLICATIONS 2300 / 1018 ( 2013 . 01 ) ; CIOG 2300 / 305 ( 2013 .01 ) ; C10G 2400 / 02 ( 2013 .01 ) ; CIOL Tian H et al: “ Alternative Processing Technology for Converting 1 / 1824 ( 2013 .01 ) ; CIOL 2200 / 0469 ( 2013 . 01 ) ; Vegetable Oils and Animal Fats to Clean Fuels and Light Olefins ” , CIOL 2270 /023 ( 2013 .01 ) ; CIOL 2290 / 24 Chinese Journal of Chemical Engineering, Chemical Industry Press, ( 2013. 01 ) ; YO2P 30 / 20 ( 2015 . 11) Beijing , Beijing, CN , vol . 16 , No. 3 , Jun . 1 , 2008 . Mar. 10 , 2017 Communication of a Notice of Opposition issued by (58 ) Field of Classification Search European Patent Office in European Application No . 12183842 . 9 . CPC .. .. .. .. .. C10G 2400 /02 ; C10G 47 /00 ; C10G Aakko - Saksa et al. , “ Biogasoline Options Possibilities for 2300 / 1018 ; C10G 50 /00 ; C10G 65 / 12 ; Achieving High Bio - share and Compatibility with Conventional C10G 2400 /30 ; C10G 3 /00 ; C10G 3 /44 ; Cars , " SAE International, Sep . 11, 2011 (cited in Mar . 10 , 2017 EP C10G 2400 /20 ; C10L 1 /04 ; CIOL Communication of a Notice of Opposition and Mar. 10 , 2017 Finnish opposition ). 2270 / 023 ; CIOL 2270 /02 ; CIOL 1 / 1802 ; “ Biogasoline Options — Possibilities for Achieving High Bio - share C10L 1 / 1817 ; YO2E 50 / 14 ; YO2E 50 / 32 ; and Compatibility with Conventional Cars, ” Extract from https : / / FO2B 43 / 02 www .researchgate . net / publication /276116883 _ Biogasoline _ Op USPC 123 / 1 A , 1 R tions _ - _ Possiblities _ for_ Achieving _ High _ Bio - share _ and _ See application file for complete search history . 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C10G 65 / 16 Wikipedia entry for “ Soybean oil, ” https :/ / en .wikipedia .org / wiki/ 208 / 134 Soybean _ oil ( cited in Mar. 10 , 2017 EP Communication of a Notice 7 , 854 ,774 B2 12 / 2010 Renninger et al. of Opposition ) 8 , 329 , 970 B2 * 12 / 2012 Harlin .. C07C 1 /2078 Apr. 27, 2017 Submission in Opposition Proceedings filed in 44 /605 European Patent Office in European Application No . 12183842 . 9 . 2003/ 0093943 A1 5 / 2003 Jordan EU directive 2009 /30 / EC of the European Parliament and of the 2003 / 0167679 AL 9 / 2003 Jordan Council of Apr. 23 , 2009 , Official Journal of the European Union , 2004 /0107634 A1 * 6 / 2004 Binions .. .. .. .. .. CIOL 1 /023 May 6 , 2009 , L140 / 88 -L140 / 113 ( cited in Apr. 27 , 2017 EP Sub 44 /359 mission in Opposition Proceedings ) . 2005 /0210739 A1 * 9 / 2005 Esen .. .. .. CIOL 1 /026 Hannu Aatola et al. , “ Hydrotreated Vegetable Oil (HVO ) as a 44 /605 Renewable Diesel Fuel : Trade - off between NOx, Particulate Emis 2006 /0101712 A15 / 2006 Burnett et al. sion , and Fuel Consumption of a Heavy Duty Engine ,” SAE 2006 / 0122442 A1 * 6 / 2006 Kohler CIOL 1 / 08 International, 2008 , http :/ /www .biofuelstp .eu /downloads / SAE _ 585 / 14 Study _ Hydrotreated _ Vegetable _ Oil _ HVO _ as _ a _ Renewable _ 2007 /0204505 A1 * 9 / 2007 Abou -Nemeh .. .. C10L 1 / 14 Diesel _ Fuel .pdf ( cited in Apr. 27 , 2017 EP Submission in Oppo 44 /333 sition Proceedings ) . 2008 / 0000149 AL 1 / 2008 Aradi 2008 /0066377 A1 * 3 / 2008 Cunningham . .. CIOL 1 / 14 Hong Yuan , “ ETBE as an additive in gasoline : advantages and 44 /385 disadvantages, ” Master of Science Thesis , Environmental Science 2008/ 0202020 AL 8 / 2008 Narayan et al. Programme, Linkopings universitet, 2006 ( cited in Apr. 27, 2017 EP 2008/ 0302001 AL 12 / 2008 Koivusalmi et al. 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