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(12) United States Patent Hallen e t a ] . US008366907B2 U S 8,366,907 B 2 Feb. 5 , 2013 (10) Patent N0.: (45) Date of Patent: (54) (75) (73) (21) (22) (65) (51) (52) (58) (56) DEOXYGENATION OF FATTY ACIDS FO R PREPARATION OF HYDROCARBONS Inventors: Richard T . Hallen, Richland, WA US); Karl O . Albrecht, Richland, WA US); Heather M . Brown, KenneWick, WA (US); James . White, Richland, WA (Us) Battelle Memorial nstitute, Richland, WA U S ) Assignee: Notice: Subject t o a n y disclaimer, the term o f h i s patent i s extended or adjusted under 35 U.S.C. 154(b) by 220 days. Appl. N0.: 12/848,887 Filed: Aug. 2 , 2010 Prior Publication Data US 012/0029250 A1 Feb. 2 , 2012 Int. C l . C10M 01/00 C10M177/00 (2006.01) C10G 71/00 (2006.01) U.S. C l . ........... . . 208/18; 208/63; 585/734; 585/737 Field of Classi?cation Search .................. . . 208/ 8 , 208/63; 585/734, 73 7 S e e application ? l e f o r complete search history. (2006.01) References Cited U.S. PATENT DOCUMENTS 1,953,232 A 4/1934 Jaeger 1,964,516 6/1934 Jaeger 2,816,905 A 12/1957 Gilbert e t a l . 2,816,906 A 12/1957 Gilbert e t a l . 2,902,512 A 9/1959 Verheyden etal. 3,391,191 A 7/1968 Velde 3,476,803 A 11/1969 Pine 3,530,198 A 9/1970 Fenton 3,632,822 A 1/1972 Conroy 3,660,491 A 5/1972 Thigpen e t a1 . 3,732,263 A 5/1973 Berman 3,856,876 A 12/1974 Burnett 3,962,035 A 6/1976 Antos 4,102,938 A 7/1978 R a o 4,262,157 A 4/1981 Horiet a 1 . 4,303,486 A 12/1981 Bardetal. 4,320,241 A 3/1982 FrankieWicZ 4,554,397 A 11/1985 Stern e t a l . 4,950,763 A 8/1990 Schommer t a l . A e t a 1 . 5,077,447 A 12/1991 Miller e t a l . 5,228,982 A 7/1993 Scouten e a . 5,233,109 A 8/1993 Chow 5,290,325 A 3/1994 Kanne t a 1 . 5,344,975 A 9/1994 Zeiler 5,364,949 A 11/1994 Neuss e t al . 5,412,120 A 5/1995 Fischeret a1 . 5,422,327 A 6/1995 Soledet a 1 . 6,187,903 B1 2/2001 Elsasseret a l . 6,864,398 B2 3/2005 O’Rear 6,946,567 B2 9/2005 Zhang t a1 . 7,001,964 B2 2/2006 Small 7,002,044 B2 2/2006 Erkey et a l . 7,229,481 B2 6/2007 Clarket a 1 . 7,459,597 B 2 12/2008 Koivusalmi e t a l . 7,491,858 B 2 2/2009 Murzin e t a 1 . 7,511,181 B 2 3/2009 Petri e t a l . 2004/0006912 A1 1/2004 Krull 2004/0074760 A1 4/2004 Portnoff e t a l . 2005/0272941 12/2005 Zhang t a 1 . 2006/0016723 A1 1/2006 Tang e t a l. 2006/0161032 A1 7/2006 Murzin e t a 1 . 2006/ 0207166 A1 9/2006 HerskoWitZ e t a l. 2006/0264684 A1 11/2006 Petri e t a l . 2007/0010682 A1 1/2007 Myllyoja e t a1 . 2007/0100166 A1 5/2007 Beavers et a1 . 2007/0131579 A1 6/2007 Koivusalmi e t a l . 2007/0135669 A1 6/2007 Koivusalmi e t a l . 2007/0244343 A1 10/2007 Brevoord e t a 1 . 2007/0281875 A1 12/2007 Scheibel e t al . 2008/0034645 A1 2/2008 Bressler 2008/0071125 A1 3/2008 L i 2008/0177114 A1 7/2008 Goossen e t al . 2008/0216391 A1 9/2008 Cortright e t a1 . (Continued) FOREIGN PATENT DOCUMENTS CA 1201080 2/1986 EP 0478075 4/1992 (Continued) OTHER PUBLICATI ONS A i, M . , “Activities for t h e decomposition o f formic acid a n d t h e acid-base properties of metal oxide catalysts,” Journal o f atalysis, 5 0 , (2), 291-300, 1977. A 1 M . , “The activity o f W03-based mixed-oxide catalysts: I. Acidic properties o f WO3-based catalysts a n d correlation with catalytic activity,” Journal ofCatalysis, 4 9 , (3), 305-312, 1977. A 1 M ., “The oxidation activity a n d acid-base properties o f SnO2 based binary catalysts : I. T h e SnOZiVZO5 system,” Journal o f Catalysis, 4 0 , (3), 318-326, 1975. A 1 , M .; Ikawa, T . , T h e acid-base properties o f MoO3iBi2O3iP2O5 catalysts a n d their correlation with catalytic activity nd selectivity. Journal ofCatalysis, 4 0 , (2), 203-211, 1975. (Continued) Primary Examiner * haWquia Young (74) Attorney, Agent, o r Firm * larquist Sparkman, LL P (57) ABSTRACT Embodiments of methods f o r making renewable diesel b y deoxygenating (decarboxylating/decarbonylating/dehydrat ing) fatty acids t o produce hydrocarbons are disclosed. Fatty acids are exposed o a catalyst selected from ) P t an d MO 3 n ZrO2 (M s W , Mo , o r a combination thereof), or b ) Pt/Ge o r P t / Sn on carbon, a nd t h e catalyst decarboxylates at least 1 0 % o f t h e fatty acids. I n particular embodiments, t h e catalyst consists essentially of0.7 W t % t a n d 1 2 W t % O3 , elative t o a mass o f catalyst, or the catalyst consists essentially o f a ) 5 Wt % t a n d ) 0.5 Wt % e r 0 . 5 W t % n , relative to amass o f catalyst. Deoxygenation i s performed Without added hydrogen and at less than 100 psi. Disclosed embodiments o f the catalysts deoxygenate a t least 1 0 % of atty acids in a fatty acid feed, a nd remain capable of deoxygenating fatty acids f o r at least 2 0 0 minutes t o more than 3 5 0 hours. 4 3 Claims, 31 Drawing Sheets
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( 1 2 ) United S t a t e s P a t e n tHallen e t a ] .
US008366907B2
U S 8 , 3 6 6 , 9 0 7 B2F e b . 5 , 2 0 1 3
( 1 0 ) Patent N 0 . :
( 4 5 ) Date o f P a t e n t :
( 5 4 )
( 7 5 )
( 7 3 )
( 2 1 )
( 2 2 )
( 6 5 )
( 5 1 )
( 5 2 )( 5 8 )
( 5 6 )
DEOXYGENATIONOFFATTYACIDS FOR
PREPARATIONOFHYDROCARBONS
I n v e n t o r s : R i c h a r d T . H a l l e n , R i c h l a n d , WA U S ) ;
K a r l O . A l b r e c h t , R i c h l a n d , WA U S ) ;
Heather M. Brown, K e n n e W i c k , WA
( U S ) ; James . W h i t e , R i c h l a n d , WA
( U s )
B a t t e l l e Memorial n s t i t u t e , R i c h l a n d ,
WA U S )
A s s i g n e e :
N o t i c e : S u b j e c t t o a n y d i s c l a i m e r , t h e t e r m o f h i sp a t e n t i s e x t e n d e d o r a d j u s t e d u n d e r 3 5
U . S . C . 1 5 4 ( b ) b y 2 2 0 d a y s .
A p p l . N 0 . : 1 2 / 8 4 8 , 8 8 7
F i l e d : A u g . 2 , 2 0 1 0
Prior P u b l i c a t i o n D at a
US 012/0029250 A1 F e b . 2 , 2012
I n t . C l .
C10M 01/00
C10M177/00 ( 2 0 0 6 . 0 1 )
C 1 0 G 7 1 / 0 0 ( 2 0 0 6 . 0 1 )
U.S. C l . . . . . . . . . . . . . . 208/18; 208/63; 585/ 734; 585/737
Field o f C l a s s i?ca t i o n Search . . . . . . . . . . . . . . . . . . . . 208/ 8 ,
2 0 8 / 6 3 ; 5 8 5 / 7 3 4 , 7 3 7S e e a p p l i c a t i o n ? l e f o r c o m p l e t e s e a r c h h i s t o r y .
( 2 0 0 6 . 0 1 )
References Cited
U . S . PATENTDOCUMENTS
1 , 9 5 3 , 2 3 2 A 4 / 1 9 3 4 J a e g e r
1 , 9 6 4 , 5 1 6 A 6 / 1 9 3 4 J a e g e r
2 , 8 1 6 , 9 0 5 A 1 2 / 1 9 5 7 G i l b e r t e t a l .
2 , 8 1 6 , 9 0 6 A 1 2 / 1 9 5 7 G i l b e r t e t a l .
2 , 9 0 2 , 5 1 2 A 9 / 1 9 5 9 V e r h e y d e n e t a l .3 , 3 9 1 , 1 9 1 A 7 / 1 9 6 8 V e l d e
3 , 4 7 6 , 8 0 3 A 1 1 / 1 9 6 9 P i n e
3 , 5 3 0 , 1 9 8 A 9 / 1 9 7 0 F e n t o n
3 , 6 3 2 , 8 2 2 A 1 / 1 9 7 2 C o n r o y
3 , 6 6 0 , 4 9 1 A 5 / 1 9 7 2 T h i g p e n e t a 1 .3 , 7 3 2 , 2 6 3 A 5 / 1 9 7 3 Ber m an
3 , 8 5 6 , 8 7 6 A 1 2 / 1 9 7 4 B u r n e t t
3 , 9 6 2 , 0 3 5 A 6 / 1 9 7 6 A n t o s
4 , 1 0 2 , 9 3 8 A 7 / 1 9 7 8 Rao
4 , 2 6 2 , 1 5 7 A 4 / 1 9 8 1 H o r i e t a 1 .
4 , 3 0 3 , 4 8 6 A 1 2 / 1 9 8 1 B a r d e t a l .
4 , 3 2 0 , 2 4 1 A 3 / 1 9 8 2 F r a n k i e W i c Z
4 , 5 5 4 , 3 9 7 A 1 1 / 1 9 8 5 S t e r n e t a l .
4 , 9 5 0 , 7 6 3 A 8 / 1 9 9 0 Sc h o m m er t a l .
4 , 9 9 2 , 6 0 5 A 2 / 1 9 9 1 C r a i g e t a 1 .5 , 0 7 7 , 4 4 7 A 1 2 / 1 9 9 1 M i l l e r e t a l .
5 , 2 2 8 , 9 8 2 A 7 / 1 9 9 3 S c o u t e n e t a l .
5 , 2 3 3 , 1 0 9 A 8 / 1 9 9 3 C h o w5 , 2 9 0 , 3 2 5 A 3 / 1 9 9 4 K a n n e t a 1 .
5 , 3 4 4 , 9 7 5 A 9 / 1 9 9 4 Z e i l e r
5 , 3 6 4 , 9 4 9 A 1 1 / 1 9 9 4 Neuss e t a l .
5 , 4 1 2 , 1 2 0 A 5 / 1 9 9 5 F i s c h e r e t a 1 .
5 , 4 2 2 , 3 2 7 A 6 / 1 9 9 5 S o l e d e t a 1 .
6 , 1 8 7 , 9 0 3 B1 2 / 2 0 0 1 E l s a s s e r e t a l .
6 , 8 6 4 , 3 9 8 B2 3 / 2 0 0 5 O’Rear
6 , 9 4 6 , 5 6 7 B2 9 / 2 0 0 5 Zhang t a 1 .7 , 0 0 1 , 9 6 4 B2 2 / 2 0 0 6 S m a l l
7 , 0 0 2 , 0 4 4 B2 2 / 2 0 0 6 E r k e y e t a l .
7 , 2 2 9 , 4 8 1 B2 6 / 2 0 0 7 C l a r k e t a 1 .
7 , 4 5 9 , 5 9 7 B2 1 2 / 2 0 0 8 K o i v u s a l m i e t a l .
7 , 4 9 1 , 8 5 8 B2 2 / 2 0 0 9 Murzin e t a 1 .
7 , 5 1 1 , 1 8 1 B2 3 / 2 0 0 9 P e t r i e t a l .2004/0006912 A1 1 / 2 0 0 4 K r u l l
2004/0074760 A1 4/2004 P o r t n o f f e t a l .
2 0 0 5 / 0 2 7 2 9 4 1 A1 1 2 / 2 0 0 5 Zh ang t a 1 .
2006/0016723 A1 1 / 2 0 0 6 Tang e t a l .
2006/0161032 A1 7 / 2 0 0 6 Murzin e t a 1 .
2 0 0 6 / 0207166 A1 9 / 2 0 0 6 HerskoWitZ e t a l .
2006/0264684 A1 1 1 / 2 0 0 6 P e t r i e t a l .
2007/0010682 A1 1 / 2 0 0 7 M y l l y o j a e t a 1 .
2007/0100166 A1 5 / 2 0 0 7 Beavers e t a 1 .
2007/0131579 A1 6 / 2 0 0 7 Koivusalmi e t a l .
2007/0135669 A1 6 / 2 0 0 7 Koivusalmi e t a l .
2007/0244343 A1 1 0 / 2 0 0 7 Brevoord e t a 1 .
2007/0281875 A1 1 2 / 2 0 0 7 S c h e i b e l e t a l .
2008/0034645 A1 2 / 2 0 0 8 B r e s s l e r
2008/0071125 A1 3 / 2 0 0 8 L i
2008/0177114 A1 7/2008 Goossen e t a l .
2 0 0 8 / 0 2 1 6 3 9 1 A1 9 / 2 0 0 8 C o r t r i g h t e t a 1 .
( C o n t i n u e d )
FOREIGNPATENTDOCUMENTS
CA 1201080 2/1986
EP 0478075 4/1992
( C o n t i n u e d )
OTHERPUBLICATIONS
A i, M . , “ A c t i v i t i e s f o r t h e d e c o m p o s i t i o n o f f o r m i c a c i d a n d t h e
a c i d - b a s e p r o p e r t i e s o f m e t a l o x i d e c a t a l y s t s , ” J o u r n a l o f a t a l y s i s ,
5 0 , ( 2 ) , 2 9 1 - 3 0 0 , 1 9 7 7 .A 1 , M . , “ T h e a c t i v i t y o f W 0 3 - b a s e d m i x e d - o x i d e c a t a l y s t s : I . A c i d i c
p r o p e r t i e s o f W O 3 - b a s e d c a t a l y s t s a n d c o r r e l a t i o n w i t h c a t a l y t i ca c t i v i t y , ” J o u r n a l o f C a t a l y s i s , 4 9 , ( 3 ) , 3 0 5 - 3 1 2 , 1 9 7 7 .A 1 , M . , “ T h e o x i d a t i o n a c t i v i t y a n d a c i d - b a s e p r o p e r t i e s o f S n O 2
b a s e d b i n a r y c a t a l y s t s : I . T h e S n O Z i V Z O 5 s y s t e m , ” J o u r n a l o f
C a t a l y s i s , 4 0 , ( 3 ) , 3 1 8 - 3 2 6 , 1 9 7 5 .A 1 , M . ; I k a w a , T . , T h e a c i d - b a s e p r o p e r t i e s o f MoO3iBi2O3iP2O5c a t a l y s t s a n d t h e i r c o r r e l a t i o n w i t h c a t a l y t i c a c t i v i t y a n d s e l e c t i v i t y .
J o u r n a l o f C a t a l y s i s , 4 0 , ( 2 ) , 2 0 3 - 2 1 1 , 1 9 7 5 .
( C o n t i n u e d )
Primary Examiner * haWquia You n g
( 7 4 ) A t t o r n e y , A g e n t , o r Firm * l a r q u i s t S p a r k m a n , LL P
( 5 7 ) A B S T R A C T
E m b o d i m e n t s o f m e t h o d s f o r making r e n e w a b l e d i e s e l b y
d e o x y g e n a t i n g ( d e c a r b o x y l a t i n g / d e c a r b o n y l a t i n g / d e h y d r a ti n g ) f a t t y a c i d s t o p r o d u c e h y d r o c a r b o n s a r e d i s c l o s e d . F a t t y
a c i d s a r e exposed o a c a t a l y s t s e l e c t e d from ) P t andMO3
nZrO2 (M s W , Mo , o r a c o m b i n a t i o n t h e r e o f ) , o r b ) P t / G e o r
P t / Sn on c a r b o n , a n d t h e c a t a l y s t d e c a r b o x y l a t e s a t l e a s t 1 0%
o f t h e f a t t y a c i d s . I n p a r t i c u l a r e m b o d i m e n t s , t h e c a t a l y s tc o n s i s t s e s s e n t i a l l y o f 0 . 7 W t % t and 1 2 Wt % O 3, e l a t i v e
t o a mass o f c a t a l y s t , o r t h e c a t a l y s t c o n s i s t s e s s e n t i a l l y o f a )
5 W t % t and ) 0 . 5 W t % e r 0 . 5 W t % n , r e l a t i v e t o a m a s s
o f c a t a l y s t . D e o x y g e n a t i o n i s p e r f o r m e d W i t h o u t a d d e d
h y d r o g e n a n d a t l e s s t h a n 1 0 0 p s i . D i s c l o s e d embodiments o f
t h e c a t a l y s t s d e o x y g e n a t e a t l e a s t 1 0% o f a t t y a c i d s i n a f a t t y
a c i d f e e d , a n d r e m a i n c a p a b l e o f d e o x y g e n a t i n g f a t t y a c i d sf o r a t l e a s t 200 minutes t o m o r e than 350 h o u r s .
4 3 C l a i m s , 3 1 Dr awing S h e e t s
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U S 8 , 3 6 6 , 9 0 7 B2P a g e 2
U S . PATENTDOCUMENTS
2008/0308457 A1 1 2 / 2 0 0 8 Dindiet l .
2008/0308458 A1 1 2 / 2 0 0 8 Dindiet l .
2008/0312346 A1 1 2 / 2 0 0 8 McCall e t a l .
2008/0312479 A1 1 2 / 2 0 0 8 McCall e t a l .
2008/0312480 A1 1 2 / 2 0 0 8 Dindiet l .
2009/0031617 A1 2/2009 O ’ R e ar2009/0041646 A1 2/2009 I k e d a e t a l .
2009/0062578 A1 3/2009 Koivusalmi e t a l .
2009/0069610 A1 3 / 2 0 0 9 R o b e r t s , IV e t a l .2009/0077867 A1 3/2009 Marker e t a l .
2009/0077868 A1 3 / 2 0 0 9 Brady t a l .
2009/0247799 A1 1 0 / 2 0 0 9 M y l l y o j a e t a l .
2009/0283442 A1 1 1 / 2 0 0 9 McCall e t a l .
2010/0076233 A1 3 / 2 0 1 0 C o r t r i g h t e t a l .
2010/0113848 A1 5 / 2 0 1 0 S t r e g e e t a l .
2010/0137663 A1 6/2010 C h e n t a l .
2010/0145117 A1 6/2010 S eam e s e t a l .
2010/0151535 A1 6/2010 F r a n k l i n e t a l .
FOREIGNPATENTDOCUMENTS
EP 1489157 1 2 / 2 0 0 4
EP 1681337 7/2006
EP 1741767 1 / 2 0 0 7
EP 1741768 1 / 2 0 0 7EP 1911735 4/2008
GB 1074265 7/1967
GB 1524781 9/1978
GB 2039943 8 / 1 9 8 0
W0 WO 003/082464 1 0 / 2 0 0 3
W0 WO 006/075057 7/2006
W0 WO 007/003708 1 / 2 0 0 7
W0 WO 007/068795 6/2007
W0 WO 007/068798 6/2007
W0 WO 007/068799 6/2007
W0 WO 007/068800 6 / 2 0 0 7
W0 WO 007/107337 9/2007
W0 WO 007/136873 1 1 / 2 0 0 7
W0 WO 008/029301 3/2008
W0 WO 008/040973 4/2008
W0 WO 008/103204 8 / 2 0 0 8
W0 WO 008/138861 1 1 / 2 0 0 8
W0 WO 008/157165 1 2 / 2 0 0 8
W0 WO 008/157465 1 2 / 2 0 0 8W0 WO 009/008893 1 / 2 0 0 9
W0 WO 009/011160 1 / 2 0 0 9
W0 WO 009/011639 1 / 2 0 0 9
W0 WO 009/025635 2/2009
W0 WO 009/025663 2/2009
W0 WO 009/035689 3/2009
WO W O20 10 /032748 3 / 2 0 1 0
W0 WO 010/043765 4/2010
WO W O20 10 /068904 6 / 2 0 1 0
OTHERPUBLICATIONS
A i , M . ; S u z u k i , S . , “ O x i d a t i o n a c t i v i t y a n d a c i d i t y o f MoO3iP2O5
c a t a l y s t s , ” J o u r n a l o f C a t a l y s i s , 3 0 , ( 3 ) , 3 6 2 - 3 7 1 , 1 9 7 3 .
A i z e n s h t a t , Z . ; M i l o s l a y s k y , I . ; H e l l e r - K a l l a i , L . , “ T h e e f f e c t o f
m o n t m o r i l l o n i t e on t h e t h e r m a l d e c o m p o s i t i o n o f f a t t y a c i d s u n d e r
“ b u l k ?ow” o n d i t i o n s , ” O r g a n i c G e o c h e m i s t r y 7 , ( 1 ) , 8 5 - 9 0 , 1 9 8 4 .
A l e n c a r , J . W . ; A l v e s , P . B . ; C r a v e i r o , A . A . , “ P y r o l y s i s o f t r o p i c a lv e g e t a b l e o i l s , ” J o u r n a l o f A g r i c u l t u r a l a n d F o o d C h e m i s t r y , 3 1 , ( 6 ) ,
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c a t a l y z e d a t t y a c i d d e c a r b o x y l a t i o n , ” r o c . I n t . C l a y C o n f , 3 9 9 4 0 9 ,1 9 7 5 .
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A d v . O r g . G e o c h e m . , P r o c . I n t . M e e t , 7 ” ’ , 1 5 7 - 7 1 , 1 9 7 7 .
A r a u j o , L . R . R . d . ; S c o ? e l d , C . F . ; P a s t u r a , N . M. R . ; G o n z a l e z , W.
d . A . , “ H 3 P O 4 / A l 2 O 3 c a t a l y s t s : c h a r a c t e r i z a t i o n a n d c a t a l y t i c e v a l u
a t i o n o f l e i c a c i d c o n v e r s i o n t o b i o f u e l s and i o l u b r i c a n t , ” M a t e r i a l s
R e s e a r c h , 9 , ( 2 ) , 1 8 1 - 1 8 4 , 2 0 0 6 .
B a c h a , J . D . ; K o c h i , J . K . , “ A l k e n e s f r o m a c i d s by o x i d a t i v e
d e c a r b o x y l a t i o n , ” T e t r a h e d r o n , 2 4 , ( 5 ) , 2 2 1 5 - 2 2 2 6 , 1 9 6 8 .
B e r n a s , A . ; K u m a r , N . ; M a k i - A r v e l a , P . ; K u l ’ k o v a , N . V . ; H o l m b o m ,
B . ; S a l m i , T . ; M u r z i n , D . Y . , “ I s o m e r i z a t i o n o f l i n o l e i c a c i d o v e r
s u p p o r t e d m e t a l c a t a l y s t s , ” A p p l i e d C a t a l y s i s A . ‘ G e n e r a l , 2 4 5 , ( 2 ) ,
2 5 7 - 2 7 5 , 2 0 0 3 .
B e s s o n , M . ; G a l l e z o t , P . , “ S e l e c t i v e o x i d a t i o n o f a l c o h o l s a n d
a l d e h y d e s o n m e t a l c a t a l y s t s , ” C a t a l y s i s T o d a y , 5 7 , ( 1 - 2 ) , 1 2 7 - 1 4 1 ,
2 0 0 0 .
B i l l a u d , F . ; D o m i n g u e z , V . ; B r o u t i n , P ; B u s s o n , C , “ P r o d u c t i o n o f
H y d r o c a r b o n s b y P y r o l y s i s o f M e t h y l E s t e r s f r o m R a p e s e e d O i l , ”
J o u r n a l o f t h e A m e r i c a n O i l C h e m i s t s S o c i e t y , 7 2 , ( 1 0 ) , 1 1 4 9 1 1 5 4 ,
1 9 9 5 .
B o o c o c k , D . G . B . ; K o n a r , S . K . ; G l a s e r , G . , “ T h e F o r m a t i o n o f
P e t r o d i e s e l by t h e P y r o l y s i s o f F a t t y A c i d M e t h y l E s t e r s o v e r A c t i
v a t e d A l u m i n a , ” P r o g r e s s i n T e r m o c h e m i c a l B i o m a s s C o n v e r s i o n ,
B r i d g w a t e r , A . V . , E d . B l a c k w e l l P u b l i s h i n g , 1 5 1 7 - 1 5 2 4 , 2 0 0 1 .
C e n t e n o , A . ; L a u r e n t , E . ; D e l m o n , B . , “ I n ? u e n c e o f t he S u p p o r t o f
CoMo u l ? d e C a t a l y s t s a n d o f t h e A d d i t i o n o f P o t a s s i u m a n d P l a t i
num n t h e C a t a l y t i c P e r f o r m a n c e s f o r t h e Hydrodeoxygenation o f
C a r b o n y l , C a r b o x y l , a n d G u a i a c o l - T y p e M o l e c u l e s , ” J o u r n a l o f
C a t a l y s i s , 1 5 4 , ( 2 ) , 2 8 8 - 2 9 8 , 1 9 9 5 .C o r m a , A . ; R e n z , M . ; S c h a v e r i e n , C , “ C o u p l i n g F a t t y A c i d s b y
K e t o n i c D e c a r b o x y l a t i o n U s i n g S o l i d C a t a l y s t s f o r t he D i r e c t P r o
d u c t i o n o f D i e s e l , L u b r i c a n t s , a n d C h e m i c a l s , ” C h e m S u s C h e m , 1 ,
( 8 - 9 ) , 7 3 9 - 7 4 1 , 2 0 0 8 .
d e Lange e t a l . “Deoxygenation o f b e n z o i c a c i d on m e t a l o x i d e s : 1 .
T h e s e l e c t i v e p a t h w a y t o b e n z a l d e h y d e , ” A p p l i e d C a t a l y s i s . ‘ G e n
e r a l , 2 2 0 ( 1 - 2 ) , 4 1 - 4 9 , 2 0 0 1 .
D o o l e y e t a l . , “ K e t o n e s f r o m a c i d c o n d e n s a t i on u s i n g s u p p o r t e d
C e O 2 c a t a l y s t s : E f f e c t o f a d d i t i v e s , ” A p p l i e d C a t a l y s i s A . ‘ G e n e r a l ,
3 2 0 , 1 2 2 - 1 3 3 , 2 0 0 7 .
D o s A n j o s e t a l . , “ C a t a l y t i c d e c o m p o s i t i o n o f e g e t a b l e o i l , ” A p p l i e d
C a t a l y s i s , 5 , ( 3 ) , 2 9 9 - 3 0 8 , 1 9 8 3 .Dury t a l . , “The d e o x y g e n a t i o n o f b e n z o i c a c i d a s a p r o b e r e a c t i o n
t o d e t e r m i n e t h e i m p a c t o f s u p e r ? c i a l oxygen v a c a n c i e s ( i s o l a t e d o r
t w i n ) o n t h e o x i d a t i o n p e r f o r m a n c e s o f Mo-based o x i d e c a t a l y s t s ”
C a t a l y s i s T o d a y , 1 1 7 , 4 6 - 5 2 , 2 0 0 6 .
Dury t a l . , “The i n ? u e n c e o f h e h y d r o g e n o r i g i n t t h e s u r f a c e o f Mo
s u b o x i d e d u r i n g t h e d e o x y g e n a t i o n o f c a r b o x y l i c a c i d , ” C a t a l y s i s
T o d a y , 1 1 2 , ( 1 - 4 ) , 1 3 0 - 1 3 3 , 2 0 0 6 .Dury t a l . , “ P r o b i n g t h e r e d u c t i o n s t a t e o f Mo x i d e c a t a l y s t s by he
d e o x y g e n a t i o n o f a r b o x y l i c a c i d , ” C a t a l y s i s T o d a y , 9 1 - 9 2 , 1 1 1 - 1 1 6 ,2 0 0 4 .
F e r r a r i e t a l . , “ I n ? u e n c e s o f t h e hydrogen s u l ? d e p a r t i a l p r e s s u r e an d
o f a n i t r o g e n comp oun d on t h e h y d r o d e o x y g e n a t i o n a c t i v i t y o f a
C o M o / c a r b o n c a t a l y s t , ” J o u r n a l o f C a t a l y s i s , 1 9 8 , ( 1 ) , 4 7 - 5 5 , 2 0 0 1 .
F o g l i a e t a l . , “ D e c a r b o n y l a t i o n D e h y d r a t i o n o f F a t t y A c i d s t oA l k e n e s i n t h e P r e s e n c e o f T r a n s i t i o n M e t a l C o m p l e x e s , ” J o u r n a l o f
t h e A m e r i c a n O i l C h e m i s t s ’ S o c i e t y , 5 3 ( 1 2 ) , 7 1 3 - 7 8 2 , 1 9 7 6 .
F u e t a l . , “ C a t a l y t i c h y d r o t h e r m a l d e o x y g e n a t i o n o f a l m i t i c a c i d , ”E n e r g y a n d E n v i r o n m e n t a l S c i e n c e , 3 ( 3 ) , 3 1 1 - 3 1 7 , 2 0 1 0 .
F u e t a l . , “ C a t a l y t i c d e c a r b o x y l a t i o n o f p e t r o l e u m a c i d s f r o m h i g h
a c i d c r u d e o i l s o v e r s o l i d a c i d c a t a l y s t s , ” E n e r g y & u e l s , 2 2 , ( 3 ) ,
1 9 2 3 - 1 9 2 9 , 2 0 0 8 .
G l i n s k i e t a l . , “ D e c a r b o x y l a t i v e c o u p l i ng o f h e p t a no i c a c i d . Manga
n e s e , c e r i u m an d i r c o n i u m o x i d e s a s c a t a l y s t s . ” A p p l i e d C a t a l y s i s A . ‘
G e n e r a l , 1 9 0 , ( 1 - 2 ) , 8 7 - 9 1 , 2 0 0 0 .G l i n s k i e t a l . , “ K e t o n e s f r o m m o n o c a r b o x y l i c a c i d s : C a t a l y t i c
k e t o n i z a t i o n o v e r o x id e s y s t e m s , ” A p p l i e d C a t a l y s i s A . ‘ G e n e r a l , 1 2 8 ,
( 2 ) , 2 0 9 - 2 1 7 , 1 9 9 5 .
Hey nen e t a l . , “The C a t a l y t i c D i m e r i z a t i o n o f O l e i c Acid i n a C o n
t i n u o u s F l o w R e a c t o r , ” F e t t e , S e i f e n , A n s t r i c h m i t t e l , ( 1 2 ) , 6 7 7 - 6 8 1 ,1 9 7 2 .
Hracho va e t a l . , “The e f f e c t o f mechanical t r e a t m e n t on t h e s t r u c t u r e
o f m o n t m o r i l l o n i t e , ” M a t e r i a l s L e t t e r s , 6 1 , ( 1 6 ) , 3 3 6 1 - 3 3 6 5 , 2 0 0 7 .
Idem t a l . , “ C a t a l y t i c c o n v e r s i o n o f c a n o l a i l t o f u e l s an d c h e m i c a l s :
R o l e s o f c a t a l y s t a c i d i t y , b a s i c i t y a n d s h a p e s e l e c t i v i t y o n p r o d u c t
d i s t r i b u t i o n , ” F u e l P r o c e s s i n g T e c h n o l o g y , 5 1 , ( 1 - 2 ) , 1 0 1 - 1 2 5 , 1 9 9 7 .J o h n s , “ C l a y M i n e r a l C a t a l y s i s a n d P e t r o l e u m G e n e r a t i o n , ” A n n u a l
R e v i e w o f E a r t h a n d P l a n e t a r y S c i e n c e s , 7 , ( 1 ) , 1 8 3 - 1 9 8 , 1 9 7 9 .K a l n e s e t a l . , “Green d i e s e l : a s e c o n d g e n e r a t i o n b i o f u e l , ” I n t e r n a
t i o n a l J o u r n a l o f C h e m i c a l R e a c t o r E n g i n e e r i n g , 5 , 1 0 p p . , 2 0 0 7 .
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K a t i k a n e n i e t a 1 , “ S t u d i e s o n t h e C a t a l y t i c C o n v e r s i o n o f Canola O i l
t o H y d r o c a r b o n s : I n ? u e n c e o f H y b r i d C a t a l y s t s a n d S t e a m , ” E n e r g y
& F u e l s , 9 , ( 4 ) , 5 9 9 - 6 0 9 , 1 9 9 5 .Khu rshid t a 1 . , “ E f f e c t s of Hy d r o en on Hep tane s o m e r i Z a t i o n O v e r
Z i r c o n i u m O x i d e Modi?ed w i t h T u n g s t e n O x i d e a n d P l a t i n u m , ”
A p p l i e d C a t a l y s i s A . ‘ G e n e r a l 3 6 2 , p p . 7 5 - 8 1 ; 2 0 0 9 .
K n o t h e , “ B i o d i e s e l a n d r e n e w a b l e i e s e l : A o m p a r i s o n , ” P r o g r e s s i n
E n e r g y a n d C o m b u s t i o n S c i e n c e , 2 6 , 3 6 4 - 3 7 3 , 2 0 1 0 .
Knothe e t a l . , “ B i o d i e s e l : T h e Us e o f V e g e t a b l e O i l s a n d T h e i r
D e r i v a t i v e s a s A l t e r n a t iv e D i e s e l F u e l s , ” F u e l s and Chemicals from
B i o m a s s , AC S y m p o s i u m S e r i e s , v o l . 6 6 6 , 1 7 2 - 2 0 8 , 1 9 9 7 .
Konar t a l . , “ F u e l s a n d c h e m i c a l s f r o m s e w a g e s l u d g e : 3 . H y d r o c a r
b o n l i q u i d s f r o m t h e c a t a l y t i c p y r o l y s i s o f s e w a g e s l u d g e l i p i d s o v e r
a c t i v a t e d a l u m i n a , ” F u e l , 7 3 , ( 5 ) , 6 4 2 - 6 4 6 , 1 9 9 4 .
K o s t e r e t a l . , “ A c t i v e s i t e s i n t h e c l a y c a t a l y s e d d i m e r i s a t i o n o f l e i c
a c i d , ” J o u r n a l o f M o l e c u l a r C a t a l y s i s A . ‘ C h e m i c a l , 1 3 4 , 1 5 9 - 1 6 9 ,
1 9 9 8 .
K roumova t a l . , “ A p p l i c a t i o n o f I m p r o v e d Methods o A s s e s s P a t h
w a y s f o r B i o s y n t h e s i s o f L o n g - a n d V e r y - L o n g - C h a i n F a t t y A c i d s , ”
J o u r n a l o f g r i c u l t u r a l a n d F o o d C h e m i s t r y , 4 5 , ( 1 2 ) , 4 7 0 1 - 4 7 0 5 ,
1 9 9 7 .
K u b i c k a t a l . , “ T r a n s f o r m a t i o n o f e g e t a b l e O i l s i n t o H y d r o c a r b o n s
o v e r M e s o p o r o u s - A l u m i n a - S u p p o r t e d C o M o C a t a l y s t s , ” T o p i c s i nC a t a l y s i s , 5 2 , ( 1 ) , 1 6 1 - 1 6 8 , 2 0 0 9 .
K u b i c k o v a e t a l . , “ H y d r o c a r b o n s f o r d i e s e l f u e l v i a d e c a r b o x y l a t i o n
o f v e g e t a b l e o i l s , ” C a t a l y s i s T o d a y , 1 0 6 , 1 9 7 - 2 0 0 , 2 0 0 5 .
K u m a r t a l . , “ E l e c t r o o r g a n i c s y n t h e s i s : A o v e l r o u t e o f g r e e n s y n
t h e s i s , ” J o u r n a l o f t h e I n d i a n C h e m i c a l o c i e t y , 8 6 ( 1 1 ) , 1 1 2 9 - 1 1 4 2 ,
2 0 0 9 .
K w a k , “ A p p l i c a t i o n s o f H e t e r o g e n e ou s C a t a l y t i c P r o c e s s e s t o t h e
E n v i r o n m e n t a l l y F r i e n d l y S y n t h e s i s o f F i n e C h e m i c a l s , ” C a t a l y s i s
S u r v e y s f r o m A s i a , 9 , ( 2 ) , 1 0 3 - 1 1 6 , 2 0 0 5 .L a s h d a f t a l . , “ P l a t i n u m c a t a l y s t s o n a l u m i n a a n d s i l i c a p r e p a r e d b y
g a s - a n d l i q u i d - p h a s e d e p o s i t i o n i n c i n n a m a l d e h y d e h y d r o g e n a t i o n , ”A p p l i e d C a t a l y s i s A . ‘ G e n e r a l , 2 7 6 , ( 1 - 2 ) , 1 2 9 - 1 3 7 , 2 0 0 4 .
L a u r e n t e t a l . , “ S t u d y o f t h e H y d r o d e o x y g e n a t i o n o f C a r b o n y l ,
C a r b o x y l i c a n d G u a i a c y l G r o u p s O v e r S u l ? d e d C oM o /Gam m a
A l 2 O 3 a n d N i M o / G a m m a - A l 2 O 3 C a t a l y s t s . 1 . C a t a l y t i c R e a c t i o n
S c h e m e s , ” A p p l i e d C a t a l y s i s A . ‘ G e n e r a l , 1 0 9 , ( 1 ) , 7 7 - 9 6 , 1 9 9 4 .L a u r e n t , “ S t u d y o f h e H y d r o d e o x y g e n a t i o n o f a r b o n y l , C a r b o x y l i c
a n d G u a i a c y l G r o u p s O v e r S u l ? d e d CoMo/Gamma-Al2O3 a n d
NiMo/Gamma-Al2O3 C a t a l y s t . 1 1 . I n ? u e n c e o f W a t e r , Am m o n i a n d
H y d r o g e n - S u l ? d e , ” A p p l i e d C a t a l y s i s A . ‘ G e n e r a l , 1 0 9 , ( 1 ) , 9 7 - 1 1 5 ,1 9 9 4 .
L e e e t a l . , “ D e c a r b o n y l a t i o n o f m e t h y l f o r m a t e o v e r h e t e r o g e ne o u s
c a t a l y s t s , ” A p p l i e d C a t a l y s i s A . ‘ G e n e r a l , 8 3 , 1 6 5 - 1 7 8 , 1 9 9 2 .
L e s t a r i e t a l . , “ T r a n s f o r m i n g T r i g l y c e r i d e s a n d F a t t y A c i d s i n t o
B i o f u e l s , ” C h e m S u s C h e m , 2 , ( 1 2 ) , 1 1 0 9 - 1 1 1 9 , 2 0 0 9 .
L e s t a r i e t a l . , “ C a t a l y t i c D e o x y g e n a t i o n o f S t e a r i c A c i d a n d P a l m i t i c
A c i d i n S e m i b a t c h M o d e , ” C a t a l y s i s L e t t e r s , 1 3 0 , ( 1 ) , 4 8 - 5 1 , 2 0 0 9 .
L e s t a r i e t a l . , “ C a t a l y t i c D e o x y g e n a t i o n o f S t e a r i c Acid n a C o n t i n u
o u s R e a c t o r o v e r a Mesoporous Carbon-Supported P d C a t a l y s t , ”
E n e r g y & u e l s , 2 3 , ( 8 ) , 3 8 4 2 - 3 8 4 5 , 2 0 0 9 .
L e s t a r i e t a l . , “ S y n t h e s i s o f B i o d i e s e l v i a D e o x y g e n a t i o n o f S t e a r i c
A c i d o v e r S u p p o r t e d P d / C C a t a l y s t , ” C a t a l y s i s L e t t e r s , 1 2 2 , ( 3 4 ) ,
2 4 7 - 2 5 1 , 2 0 0 8 .L e u n g e t a l . , “ P a t h w a y f o r t h e C a t a l y t i c C o n v e r s i o n o f C a r b o x y l i c
A c i d s t o H y d r o c a r b o n s o v e r A c t i v a t e d A l u m i n a , ” E n e r g y & u e l s , 9 ,
( 5 ) , 9 1 3 - 9 2 0 , 1 9 9 5 .
L e v a s s e u r , e t a l . , “ C a t a l y t i c W e t A i r O x i d a t i o n o f O l e i c Acid on
C e r i a - S u p p o r t e d P l a t i n u m C a t a l y s t . E f f e c t o f p H , ” R e a c t . K i n e t .
C a t a l . L e t t . , 8 7 , ( 2 ) , 2 6 9 - 2 7 9 , 2 0 0 6 .
L i e t a l . , “ C a t a l y t i c H y d r o t h e r m a l C o n v e r s i o n of T r i g l y c e r i d e s t o
N o n - e s t e r B i o f u e l s , ” E n e r g y F u e l s , 2 4 , 1 3 0 5 - 1 3 1 5 , 2 0 1 0 .
L i e t a l . , “ C a t a l y t i c d e c a r b o x y l a t i o n s o f f a t t y a c i d s i n i m m a t u r e o i l
s o u r c e r o c k s , ” S c i e n c e i n C h i n a , S e r i e s D . ‘ E a r t h S c i e n c e s , 4 6 , ( 1 2 ) ,
1 2 5 0 - 1 2 6 0 , 2 0 0 3 .
Lima t a l . , “ D i e s e l - l i k e f u e l o b t a i n e d b y p y r o l y s i s o f e g e t a b l e o i l s , ”
J o u r n a l o f A n a l y t i c a l a n d A p p l i e d y r o l y s i s , 7 1 , ( 2 ) , 9 8 7 - 9 9 6 , 2 0 0 4 .
L i u e t a l . , “ T r a n s i t i o n M e t a l - C a t a l y z e d N o n o x id a t i v e D e c a r b o x y l a
t i o n R e a c t i o n s , ” B i o c h e m i s t r y , 4 5 , ( 3 5 ) , 1 0 4 0 7 - 1 0 4 1 1 , 2 0 0 6 .
Maher e t a l . , “ P y r o l y t i c D e c a r b o x y l a t i o n a n d C r a c k i n g o f S t e a r i c
A c i d , ” I n d u s t r i a l & E n g i n e e r i n g C h e m i s t r y R e s e a r c h , 4 7 , ( 1 5 ) , 5 3 2 8
5 3 3 6 , 2 0 0 8 .
M a i e r e t a l . , “ H y d r o g e n o l y s i s G a s - P h a s e D e c a r b o x y l a t i o n o f
C a r b o x y l i c - A c i d s , ” C h e m i s c h e e r i c h t e - R e c u e i l , 1 1 5 , ( 2 ) , 8 0 8 - 8 1 2 ,
1 9 8 2 .
M a k i - A r v e l a e t a l . , “ C a t a l y t i c d e o x y g e n a t i o n o f a t t y a c i d s a n d t h e i r
d e r i v a t i v e s , ” E n e r g y & u e l s , 2 1 , ( 1 ) , 3 0 - 4 1 , 2 0 0 7 .
Maki-Arvela t a l . , “ C o n t i n u o u s d e c a r b o x y l a t i o n o f l a u r i c a c i d o v e r
P d / C c a t a l y s t , ” F u e l , 8 7 , ( 1 7 - 1 8 ) , 3 5 4 3 - 3 5 4 9 , 2 0 0 8 .
M a t s u b a r a e t a l . , “ P a l l a d i u m - c a t a l y z e d d e c a r b o x y l a t i o n a n d
d e c a r b o n y l a t i o n u n d e r h y d r o t h e r m a l c o n d i t i o n s : d e c a r b o x y l a t i v e
d e u t e r a t i o n , ” O r g a n i c L e t t e r s , 6 , ( 1 2 ) , 2 0 7 1 - 2 0 7 3 , 2 0 0 4 .
More e t a l . , “ P r e l i m i n a r y I n v e s t i g a t i o n s o f t he C a t a l y t i c
D e o x y g e n a t i o n o f F a t t y A c i d s ” AlChE A n n u a l M e e t i n g , S a n F r a n
c i s c o , CA, 2 p p . , 2 0 0 6 .
Morgan e t a l . , “ C o n v e r s i o n o f T r i g l y c e r i d e s t o H y d r o c a r b o n s O v e r
S u p p o r t e d M e t a l C a t a l y s t s , ” T o p i c s i n C a t a l y s i s , 5 3 , 8 2 0 - 8 2 9 , 2 0 1 0 .
N a e t a l . , “ H y d r o c a r b o n p r o d u c t i o n f r o m d e c a r b o x y l a t i o n o f f a t t y
a c i d w i t h o u t h y d r o g e n , ” C a t a l y s i s T o d a y , I n P r e s s , C o r r e c t e d P r o o f ,5 p p . , 2 0 0 9 .
N a i d j a e t a l . , “ O x i d a t i v e d e c a r b o x y l a t i o n o f i s o c i t r i c a c i d i n t he
p r e s e n c e o f m o n t m o r i l l o n i t e , ” C l a y M i n e r a l s , 2 5 , ( 1 ) , 2 7 - 3 7 , 1 9 9 0 .
N ak ano e t a l . , “Thermal A l t e r a t i o n o f O l e i c Acid in t h e P r e s e n c e o f
C l a y C a t a l y s t s w i t h C o - C a t a l y s t s , ” J o u r n a l o f t h e A m e r i c a n O il
C h e m i s t s S o c i e t y , 6 2 , ( 5 ) , 8 8 8 - 8 9 1 , 1 9 8 5 .
Negron-MendoZa e t a l . , “ S e l e c t i v e b l o c k i n g s i t e s i n t h e s t r u c t u r e
c l a y - n a n o m e t r i c m o n t m o r i l l o n i t e , ” N a n o s t r u c t u r e d M a t e r i a l s , 9 ,
( 1 - 8 ) , 2 0 9 - 2 1 2 , 1 9 9 7 .
N g e t a l . , “ C o n v e r s i o n o f P o l y e t h y l e n e t o T r a n s p o r t a t i o n F u e l s
t h r o u g h P y r o l y s i s a n d C a t a l y t i c C r a c k i n g , ” E n e r g y & u e l s , 9 , ( 5 ) ,
7 3 5 - 7 4 2 , 1 9 9 5 .
O o i e t a l . , “ C a t a l y t i c C o n v e r s i o n o f F a t t y A c i d s M i x t u r e t o L i q u i d
F u e l an d h e m i c a l s o v e r C o m p o s i t e M i c r o p o r o u s / M e s o p o r o u s C a t a
l y s t s , ” E n e r g y & u e l s , 1 9 , ( 3 ) , 7 3 6 - 7 4 3 , 2 0 0 5 .
P a r m o n , “ C a t a l y t i c t e c h n o l o g i e s f o r e n e r g y p r o d u c t i o n a n d r e c o v e r y
i n t h e f u t u r e , ” C a t a l y s i s T o d a y , 3 5 , ( 1 - 2 ) , 1 5 3 - 1 6 2 , 1 9 9 7 .
Pestman e t a l . , “ R e a c t i o n s o f C a r b o x y l i c A c i d s o n O x i d e s : 2 .
B i m o l e c u l a r R e a c t i o n o f A l i p h a t i c A c i d s t o K e t o n e s , ” J o u r n a l o fC a t a l y s i s , 1 6 8 , ( 2 ) , 2 6 5 - 2 7 2 , 1 9 9 7 .P in g e t a l . , “ H i g h l y d i s p e r s e d p a l l a d i u m n a n o p a r t i c l e s o n u l t r a - p or o u s s i l i c a m e s o c e l l u l a r foam f o r t h e c a t a l y t i c d e c a r b o x y l a t i o n o f
s t e a r i c a c i d , ” M i c r o p o r o u s a n d M e s o p o r o u s M a t e r i a l s , 1 3 2 , ( 1 - 2 ) ,1 7 4 - 1 8 0 , 2 0 1 0 .
R a j a d u r a i , “ P a t h w a y s f o r C a r b o x y l i c A c i d D e c o m p o s i t i o n o n T r a n
s i t i o n M e t a l O x i d e s , ” C a t a l y s i s R e v i e w s i S c i e n c e a n d E n g i n e e r i n g ,
3 6 , ( 3 ) , 3 8 5 - 4 0 3 , 1 9 9 4 .R e n Z , “ K e t o n i Z a t i o n o f C a r b o x y l i c A c i d s b y D e c a r b o x y l a t i o n :
M e c h a n i s m a n d S c o p e , ” E u r o p e a n J o u r n a l o f O r g a n i c C h e m i s t r y ,
2 0 0 5 ( 6 ) , 9 7 9 - 9 8 8 , 2 0 0 5 .
R o b e r t s e t a l . , “ O x i d a t i v e d e c a r b o x y l a t i o n o f r e t i n o i c a c i d i n
m i c r o s o m e s o f r a t l i v e r a n d k i d n e y . ” J L i p i d R e s . , 9 , ( 4 ) , 5 0 1 - 5 0 8 ,
1 9 6 8 .
S a k a t a e t a l . , “ R e d u c t i o n o f b e n Z o ic a c i d o n Ce O2 a n d , t h e e f f e c t o f
a d d i t i v e s , ” A p p l i e d C a t a l y s i s A . ‘ G e n e r a l , 1 6 6 , ( 1 ) , 1 7 3 - 1 8 4 , 1 9 9 8 .
S a k a t a t a 1 . , “ S e l e c t i v i t y P r o b l e m s in t h e C a t a l y t i c D e o x y g e n a t i o n o fB e n Z o i c A c i d , ” J o u r n a l o f C a t a l y s i s , 1 6 9 , ( 1 ) , 1 3 - 2 1 , 1 9 9 7 .
Schwab t a 1 . , “ D i e s e l F u e l from Thermal Decomposition o f Soybean
O i l , ” J o u r n a l o f t h e A m e r i c a n O i l C h e m i s t s S o c i e t y , 6 5 , ( 1 1 ) , 1 7 8 1
1 7 8 6 , 1 9 8 8 .
S e n o l e t a l . , “ H y d r o d e o x y g e n a t i o n o f m e t h y l e s t e r s o n s u l p h i d e d
NiMo/ g a m m a ] - A l 2 0 3 a n d C o M o / [ g a m m a ] - A l 2 O 3 c a t a l y s t s , ”
C a t a l y s i s T o d a y , 1 0 0 , ( 3 - 4 ) , 3 3 1 - 3 3 5 , 2 0 0 5 .
Shimoyama t a l . , “ C a t a l y t i c c o n v e r s i o n o f a t t y a c i d s t o p e t r o l e u m
l i k e p a r a f ? n s a n d t h e i r m a t u r a t i o n , ” N a t u r e ( L o n d o n ) P h y s i c a l S c i
e n c e , 2 3 2 , ( 3 3 ) , 1 4 0 - 1 4 4 , 1 9 7 1 .
Simacek e t a l . , “Hydroprocessed r a p e s e e d o i l a s a s o u r c e o f h y d r o
c a r b o n - b a s e d b i o d i e s e l , ” F u e l , 8 8 , ( 3 ) , 4 5 6 - 4 6 0 , 2 0 0 9 .
Simakova e t a l . , “ D e o x y g e n a t i o n o f p a l m i t i c a n d s t e a r i c a c i d o v e r
s u p p o r t e d P d c a t a l y s t s : E f f e c t o f m e t a l d i s p e r s i o n , ” A p p l i e d C a t a l y
s i s , A . ‘ G e n e r a l , 3 5 5 , ( 1 - 2 ) , 1 0 0 - 1 0 8 , 2 0 0 9 .
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U S 8 , 3 6 6 , 9 0 7 B2P a g e 4
S m i t h e t a l . , “ C a t a l y t i c u p g r a d i n g o f r i - g l y c e r i d e s a n d f a t t y a c i d s t o
t r a n s p o r t b i o f u e l s , ” E n e r g y & n v i r o n m e n t a l S c i e n c e , 2 , 2 6 2 - 2 7 1 ,
2 0 0 9 .
S n a r e e t a l . , “ C a t a l y t i c d e o X y g e n a t i o n o f n s a t u r a t e d r e n e w a b l e f e e d
s t o c k s f o r p r o d u c t i o n o f d i e s e l f u e l h y d r o c a r b o n s , ” F u e l , 8 7 , 9 3 3
9 4 5 , 2 0 0 8 .
S n a r e e t a l . , “ H e t e r o g e n e o u s c a t a l y t i c d e o X y g e n a t i o n o f s t e a r i c a c i d
f o r p r o d u c t i o n o f b i o d i e s e l , ” I n d u s t r i a l & n g i n e e r i n g C h e m i s t r y
R e s e a r c h , 4 5 , ( 1 6 ) , 5 7 0 8 - 5 7 1 5 , 2 0 0 6 .
S n a r e e t a l . , “ C o n t i n u o u s d e o X y g e n a t i o n o f e t h y l s t e a r a t e : a model
r e a c t i o n f o r p r o d u c t i o n o f d i e s e l f u e l h y d r o c a r b o n s , ” C h e m i c a l
I n d u s t r i e s , 1 1 5 , ( C a t a l y s i s o f O r g a n i c R e a c t i o n s ) , 4 1 5 - 4 2 5 , 2 0 0 7 .
S n a r e e t a l . , “ P r o d u c t i o n o f d i e s e l f u e l from e n e w a b l e f e e d s : K i n e t
i c s o f e t h y l s t e a r a t e d e c a r b o X y l a t i o n , ” C h e m i c a l E n g i n e e r i n g J o u r
n a l , 1 3 4 , ( 1 - 3 ) , 2 9 - 3 4 , 2 0 0 7 .
S o o k n o i e t a l . , “ D e o X y g e n a t i o n o f m e t h y l e s t e r s o v e r CsNaX,” ' .
C a t a l . , 2 5 8 , ( 1 ) , 1 9 9 - 2 0 9 , 2 0 0 8 .
S u g i y a m a , e t a l . , “ K e t o n e s f r o m c a r b o X y l i c a c i d s o v e r s u p p o r t e d
m a g n e s i u m o X i d e a n d r e l a t e d c a t a l y s t s , ” C a t a l y s i s L e t t e r s , 1 4 , 1 2 7
1 3 3 , 1 9 9 2 .
T a k e m u r a e t a l . , “ C a t a l y t i c d e c a r b o X y l a t i o n o f b e n Z o i c a c i d , ” I n d u s
t r i a l & n g i n e e r i n g C h e m i s t r y P r o d u c t R e s e a r c h and e v e l o p m e n t ,
2 4 , ( 2 ) , 2 1 3 - 1 5 , 1 9 8 5 .T o l v a n e n , e t a l . , “ T h e r m a l a n d c a t a l y t i c o l i g o m e r i s a t i o n o f f a t t y
a c i d s , ” A p p l i e d C a t a l y s i s A . ‘ G e n e r a l , 3 3 0 , 1 - 1 1 , 2 0 0 7 .
V i t o l o e t a l . , “ C a t a l y t i c u p g r a d i n g o f p y r o l y t i c o i l s o v e r HZSM - 5
Z e o l i t e : b e h a v i o u r o f h e c a t a l y s t When s e d i n r e p e a t e d u p g r a d i n g
r e g e n e r a t i n g c y c l e s , ” F u e l , 8 0 , 1 7 - 2 6 , 2 0 0 1 .
V o n g h i a e t a l . , “ P a t h w a y s f o r t h e D e o X y g e n a t i o n o f T r i g l y c e r i d e s t oA l i p h a t i c H y d r o c a r b o n s o v e r A c t i v a t e d A l u m i n a , ” E n e r g y F u e l s , 9 ,( 6 ) , 1 0 9 0 - 1 0 9 6 , 1 9 9 5 .
Vu t a 1 . , “ P l a t i n u m t u n g s t a t e d Z i r c o n i a i s o m e r i Z a t i o n c a t a l y s t s P a r t :
c h a r a c t e r i z a t i o n o f a c i d a n d m e t a l p r o p e r t i e s , ” J o u r n a l o f a t a l y s i s ,2 3 1 , 4 5 3 - 4 6 7 , 2 0 0 5.
Vu e t a l . , “ P l a t i n u m t u n g s t a t e d Z i r c o n ia i s o m e r i Z a t i o n c a t a l y s t s P a r tI I : E f f e c t o f p l a t i n u m an d t u n g s t e n l o a d i n g on t h e mechanism o f
i s o m e r i Z a t i o n o f n - h e X a n e : a k i n e t i c s t u d y , ” J o u r n a l o f C a t a l y s i s ,
2 3 1 , 4 6 8 - 4 7 9 , 2 0 0 5.W a t a n a b e e t a l . , “ D e c o m p o s i t i o n o f a l o n g c h a i n s a t u r a t e d f a t t y a c i d
W i t h s o m e a d d i t i v e s i n h o t c o m p r e s s e d W a t e r , ” Energy C o n v e r s i o n &
M a n a g e m e n t , 4 7 , 3 3 4 4 - 3 3 5 0 , 2 0 0 6 .W a t a n a b e e t a l . , “ C a t a l y t i c d e c a r b o X y l a t i o n o f a c e t i c a c i d W i t h
Z i r c o n i a c a t a l y s t i n s u p e r c r i t i c a l W a t e r , ” A p p l i e d C a t a l y s i s A . ‘ G e n
e r a l , 2 1 9 , ( 1 - 2 ) , 1 4 9 - 1 5 6 , 2 0 0 1 .Yok oyama e t a l . , “ N o v e l d i r e c t h y d r o g e n a t i o n p r o c e s s o f a r o m a t i c
c a r b o X y l i c a c i d s t o t h e c o r r e s p o n d i n g a l d e h y d e s W i t h Z i r c o n i a c a t a
l y s t , ” A p p l i e d C a t a l y s i s A . ‘ G e n e r a l , 8 8 , ( 2 ) , 1 4 9 - 1 6 1 , 1 9 9 2 .Zaher e t a l . , “ T h e r m a l l y D ec om po s ed C o t t o n s e e d O i l a s a D i e s e l
E n g i n e F u e l , ” E n e r g y S o u r c e s , 1 5 , 4 9 9 - 5 0 4 , 1 9 9 3 .Zhang t a l . , “ N a p h t h e n i c a c i d r e m o v a l f r o m c r u d e o i l t h r o u g h c a t a
l y t i c d e c a r b o X y l a t i o n o n m a g n e s i u m o x i d e , ” A p p l i e d C a t a l y s i s , A . ‘
G e n e r a l , 3 0 3 , ( 1 ) , 1 0 3 - 1 0 9 , 2 0 0 6 .
Zhang e t a l . , “ S k e l e t a l i s o m e r i Z a t i o n o f u n s a t u r a t e d f a t t y a c i d s : t he
r o l e o f m e s o p o r e s i n H B e t a Z e o l i t e s , ” C a t a l y s i s L e t t e r s , 1 1 5 , ( 3 - 4 ) ,
1 1 4 - 1 2 1 , 2 0 0 7 .
I n t e r n a t i o n a l S e a r c h R e p o r t a n d W r i t t e n O p i n i o n i s s u e d i n c o r r e
s p o n d i n g I n t e r n a t i o n a l A p p l i c a t i o n N o . P C T / U S 1 1 / 4 6 1 5 2 , d a t e d
D e c . 1 9 , 2 0 1 1 .
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