Us 8388829

7/29/2019 Us 8388829

1/56

US008388829B2

( 1 2 ) Ulllted States Patent ( 1 0 ) P a t e n t N 0 . : U S 8 , 3 8 8 , 8 2 9 B2H a l l e n e t a l . ( 4 5 ) Date o f P a t e n t : Mar. 5 , 2013

( 5 4 ) DEOXYGENATION OF FATTYACIDS FOR 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 .PREPARATIONOFHYDROCARBONS 6 , 8 6 4 , 3 9 8 B2 3 / 2 0 0 5 ORear6 , 9 4 6 , 5 6 7 B2 9 / 2 0 0 5 Zhang t a l .

. . _ 7,001,964 B2 2/2006 Small( 7 5 ) I n v e n t o r s : Richard . H a l l e n , R l c h l a n d , WA U S ) , 7 , 0 0 2 , 0 4 4 B 2 200% E r k e y e t a 1 Karl 0- A l b r e c h t , R l c h l a n d , WA U s ) ; 7 , 2 2 9 , 4 8 1 B2 6 / 2 0 0 7 C l a r k e t a l .Heather M. Brown, K e n n e W i c k , WA 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 .( U S ) ; James . W h i t e , R i c h l a n d , WA 7 , 4 9 1 , 8 5 8 B 2 2 / 2 0 0 9 M u r z l n e t a l(US) 7 , 5 1 1 , 1 8 1 B2 3 / 2 0 0 9 P e t r r e t a l .

7,967,973 B2 6/2011 Myllyoja e t a l . . . . . . . . . . . . . . . . . 208/642004/0006912 A1 1 / 2 0 0 4 K r ' u l l( 7 3 ) A s s i g n e e : B a t t e l l e Memorial I n s t i t u t e , R i c h l a n d , 2 0 0 4 / 0 0 7 4 7 6 0 A1 4 / 2 0 0 4 p o l - t n o f f e t a l WA US ) 2 0 0 5 / 0 2 7 2 9 4 1 A1 1 2 / 2 0 0 5 Zhang t a l .2 0 0 6 / 0 0 1 6 7 2 3 A1 1 / 2 0 0 6 T a n g c t a l .

( * ) 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 s g u f z k l n e l t a l t l' ' ers 0W1 c ap a t e n t 1 s extended o r a d j u s t e d under 35 2 0 0 6 / 0 2 6 4 6 8 4 A1 110006 P e t r i e t a 1

U - S - C - 1 5 4 ( 1 ) ) by 0 d a y s - 2 0 0 7 / 0 0 1 0 6 8 2 A1 1 / 2 0 0 7 M y l l y o j a e t a l .2007/0100166 A1 5 / 2 0 0 7 Beavers e t a l .

( 2 1 ) A p p l . N o . : 1 3 / 6 2 0 , 2 6 8 2 0 0 7 / 0 1 3 1 5 7 9 A1 6 / 2 0 0 7 K o i v u s a l m i e t a l .2007/0135669 A1 6 / 2 0 0 7 Koivusalmi e t a l .~ . 2007/0244343 A1 1 0/ 2007 Brevoord t a l.( 2 2 ) F 1 l e d . S e p . 1 4 , 2 0 1 2 ( C o n t i n u e d )( 6 5 ) P r i o r P u b l i c a t i o n Data

FOREIGNPATENTDOCUMENTSUS 013/0008080 A1 J a n . 1 0 , 2013 CA 1201080 2/1986EP 0478075 4/1992R e l a t e d US. A p p l i c a t i o n Data ( C o n t i n u e d )

3 . A i , M . , A c t i v i t i e s f o r t h e decomposition of f o r m i c a c i d and t h e( 5 1 ) [ 1 1 1 ; CL 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 ,

C10M 0 1 / 0 0 ( 2 0 0 6 . 0 1 ) 5 0 , ( 2 ) , 2 9 1 - 3 0 0 , 1 9 7 7C10M 7 7 / 0 0 (200601) A i , 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 cC10G 7 1 / 0 0 ( 2 0 0 6 0 1 ) p r o p e r t r 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 r o n W 1 t h c a t a l y t r c_ _ _ a c t r v r t y , Journal ofCatalysls, 49, ( 3 ) , 305-312, 1977.( 5 2 ) US. l . . . . . . . 2 0 8 / 1 8 , 2 0 8 / 6 3 , 5 8 5 / 7 3 4 , 5 8 5 / 7 3 7 A i , 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 m e s o f S n O 2 _

( 5 8 ) F i e l d of Classi?cation Search . . . . . . . . . . . . . . . . . . 585/734, b a s e d b i n a r y c a t a l y s t s ; I , Th e S H O Z i V Z O 5 S y s t e m , J o u r n a l of

( 5 6 )5 8 5 / 7 3 7

S 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 .Referenc es Cited

U . S . PATENTDOCUMENTS1 , 9 5 3 , 2 3 2 A 4 / 1 9 3 4 J a e g e r1 , 9 6 4 , 5 1 6 A 6 / 1 9 3 4 J a e g e r2 , 8 1 6 , 9 0 5 A 1 2 / 1 9 5 7 G i l b e r t e t a 1 .2 , 8 1 6 , 9 0 6 A 1 2 / 1 9 5 7 G i l b e r t e t a 1 .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 e3 , 4 7 6 , 8 0 3 A 1 1 / 1 9 6 9 P i n e3 , 5 3 0 , 1 9 8 A 9 / 1 9 7 0 F e n t o n3 , 6 3 2 , 8 2 2 A 1 / 1 9 7 2 C o n r o y3 , 6 6 0 , 4 9 1 A 5 / 1 9 7 2 T h i g p e n e t a l .3 , 7 3 2 , 2 6 3 A 5 / 1 9 7 3 Berman3 , 8 5 6 , 8 7 6 A 1 2 / 1 9 7 4 B u r n e t t3 , 9 6 2 , 0 3 5 A 6 / 1 9 7 6 A n t o s4 , 1 0 2 , 9 3 8 A 7 / 1 9 7 8 R ao4 , 2 6 2 , 1 5 7 A 4 / 1 9 8 1 H o r i e t a l .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 Z4 , 5 5 4 , 3 9 7 A 1 1 / 1 9 8 5 S t e r n e t a 1 .4 , 9 5 0 , 7 6 3 A 8 / 1 9 9 0 S c h o m m e r t a l .4 , 9 9 2 , 6 0 5 A 2 / 1 9 9 1 C r a i g e t a l .5 , 0 7 7 , 4 4 7 A 1 2 / 1 9 9 1 M i l l e r e t a 1 .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 Chow5 , 2 9 0 , 3 2 5 A 3 / 1 9 9 4 Kanne t a l .5 , 3 4 4 , 9 7 5 A 9 / 1 9 9 4 Z e i l e r5 , 3 6 4 , 9 4 9 A 1 1 / 1 9 9 4 Neuss 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 l .5 , 4 2 2 , 3 2 7 A 6 / 1 9 9 5 S o l e d e t a l .

C a t a l y s i s , 4 0 , ( 3 ) , 3 1 8 - 3 2 6 , 1 9 7 5 .A i , 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 .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 MoO3iP2O5c 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 .

( C o n t i n u e d )Primary Examiner* haWquia Young( 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 , LLP( 5 7 ) ABS T R ACTE 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 yd 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 ya c i d s a r e e x p o s e d t o a c a t a l y s t s e l e c t e d from ) P t and M03 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 rP t / Sn on 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 Wt % t and 1 2 Wt % 03, e l a t i v et 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 Wt % t and ) 0 . 5 Wt % e r 0 . 5 Wt % n , r e l a t i v e t o amasso 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 dh 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 ft 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 ya 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 .

1 6 C l a i m s , 3 1 Drawing S h e e t s

7/29/2019 Us 8388829

2/56

US 8 , 3 8 8 , 8 2 9 B2P a g e 2

US . PATENTDOCUMENTS2007/0281875 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 r2008/0071125 A1 3 / 2 0 0 8 L i2008/0177114 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 l .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 ORear2009/0041646 A1 2/2009 I k e d a e t a l .2009/0062578 A1 3 / 2 0 0 9 Koivusalmiet l .2009/0069610 A1 3 / 2 0 0 9 R o b e r t s , IV 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 .2 0 1 0 / 0 1 1 3 8 4 8 A1 5 / 2 0 1 0 S t r e g e e t a l .2010/0137663 A1 6/2010 Chen t a l .2010/0145117 A1 6 / 2 0 1 0 Seames e t a l .2010/0151535 A1 6 / 2 0 1 0 F r a n k l i n e t a l .

FOREIGNPATENTDOCUMENTSEP 1489157 1 2 / 2 0 0 4EP 1681337 7/2006EP 1741767 1 / 2 0 0 7EP 1741768 1 / 2 0 0 7EP 1911735 4/2008GB 1074265 7/1967GB 1524781 9/1978GB 2039943 8 / 1 9 8 0W0 W0 3/082464 1 0 / 2 0 0 3W0 WO 006/075057 7 / 2 0 0 6W0 WO 007/003708 1 / 2 0 0 7W0 WO 007/068795 6/2007W0 WO 007/068798 6/2007W0 WO 007/068799 6/2007W0 WO 007/068800 6/2007W0 WO 007/107337 9/2007W0 WO 007/136873 1 1 / 2 0 0 7W0 WO 008/029301 3/2008W0 WO 008/040973 4/2008W0 WO 008/103204 8 / 2 0 0 8W0 WO 008/138861 1 1 / 2 0 0 8W0 WO 008/157165 1 2 / 2 0 0 8W0 WO 008/157465 1 2 / 2 0 0 8W0 WO 009/008893 1 / 2 0 0 9W0 WO 009/011160 1 / 2 0 0 9W0 WO 009/011639 1 / 2 0 0 9W0 WO 009/025635 2/2009W0 WO 009/025663 2/2009W0 WO 009/035689 3/2009WO WO2010/032748 3 / 2 0 1 0W0 WO 010/043765 4/2010WO WO2010/068904 6 / 2 0 1 0

OTHERPUBLICATIONSA i z e n s h t a t , Z . ; M i l o s l a v 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 fm o n t r n 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 ) ,1 2 6 8 - 1 2 7 0 , 1 9 8 3 .A l m o n , W . R . ; J o h n s , W . D . , P e t r o l e u m f o r m i n g r e a c t i o n s : c l a yc a t a l y z e d f a t t y a c i d d e c a r b o x y l a t i o n , P r o c . I n t . C l a y C o n f , 3 9 9 4 0 9 ,1 9 7 5 .A l m o n , W. R . ; J o h n s , W. D . , P e t r o l e u m f o r m i n g r e a c t i o n s : t h em e c h a n i s m a n d r a t e o f c l a y c a t a l y z e d f a t t y a c i d d e c a r b o x y l a t i o n , 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. . ; 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 ua t i o n o f o 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 sR 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 ed 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 rs 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 da 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 fH 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 fP e t r o d i e s e l by 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 iv 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 h e S u p p o r t o fCoMo 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 inum 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 fC 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 fC 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 yK 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 h e D i r e c t P r od 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 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 A . G e ne 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 o n u s i n g s u p p o r t e dC 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 dC 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 nt 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 rt 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 a t t h e s u r f a c e o f Mos 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 sT 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 h ed e o x y g e n a t i o n of 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 ando f a n i t r o g e n compound 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 aC 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 ft 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 of p 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 ha 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 n g o f h e p t a n o i c a c i d . Mangan e s e , c e r i u m and 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 ck e t o n i z a t i o n o v e r o x i d e s y s t e m s , A p p l ie 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 .Heynen 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 n a Co nt 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 .Hrachova t a l . , The e f f e c t o f mechanical t r e a t m e n t on h e s t r u c t u r eo f m o n t m o r i l l on 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 o i l t o f u e l s and 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 td 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 lR 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 at 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 .

7/29/2019 Us 8388829

3/56

US 8 , 3 8 8 , 8 2 9 B2P a g e 3

K a t i k a n e n i e t a 1 , S t u d i e s on 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 lt 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 .Khurshid t a 1 , E f f e c t s of Hydro en on Heptane s o m e r i Z a t i o n O v e rZ 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 , pp . 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 d i e s e l : A o m p a r i s on , P r o g r e s s i nE 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 .K n o t h e 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 and T h e i rD 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 fromB 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 rb 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 ra 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 ca 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 .Kroumova 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 hw 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 V e g e t a b le O i l s i n t o H y d r o c a r b o n so 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 CoMo 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 no 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 .Kumar 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 nt 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 S 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 o u s C a t a l y t i c P r o c e s s e s t o t h eE 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 sS 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 byg 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 CoMo/GammaA 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 nS 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 C a r b o n y l , C a r b o x y l i ca 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 dNiMo/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 , Ammonia n dH 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 n e o u sc 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 oB 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 of S t e a r i c A c i d a n d P a l m i t i cA 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 uo u s R e a c t o r o v e r a Mesoporous Carbon-Supported Pd 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 cA 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 cA 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 Wet A i r O x i d a t i o n o f O l e i c Acid onC e r i a - S u p po 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 oN 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 ls 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 i d a t i v e D e c a r b o x y l at 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 cA 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 85 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 io n o fC a r b o x y l i c - A c i d s , C h e m i s c h e B 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 of a t t y a c i d s a n d t h e i rd 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 rP 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 dd 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 ed 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 h e C a t a l y t i cD 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 nc i s c o , CA, 2 p p . , 2 0 0 6 .Morgan t 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 H y d r o c a r b o n s O v e rS u p po 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 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 ya 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 h ep 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 .Nakano 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 fC 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 ilC 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 ec 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 of 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 st 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 dF u e l and 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 al 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 yi 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 on 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 i n 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 fs 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 ns 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 nm 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 i c a c i d o n CeO2 a n d , t h e e f f e c t o fa 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 e 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 .Sc h w ab t a 1 , D i e s e l F u e l from Thermal Decomposition o f SoybeanO 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 11 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 dNiMo/ 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 f a t t y a c i d s t o p e t r o l e u ml 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 ie n c e , 2 3 2 , ( 3 3 ) , 1 4 0 - 1 4 4 , 1 9 7 1 .Simacek 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 oc 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 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 rs 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 ys 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 .

7/29/2019 Us 8388829

4/56

US 8 , 3 8 8 , 8 2 9 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 ot 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 ds 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 39 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 df 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 yR 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 modelr 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 lI 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 ti 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 rn 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 po r t e dm 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 71 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 st 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 ya 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 H ZS M - 5Z 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 gr 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 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 la t i n u m and t u n g s t e n l o a d i n g on t h e mechanism o fi 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 dW i t h some 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 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 hZ 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 ne r a l , 2 1 9 , ( 1 - 2 ) , 1 4 9 - 1 5 6 , 2 0 0 1 .Yokoyama 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 cc 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 al 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 Decom pos ed C o t t o n s e e d O i l a s a D i e s e lE 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 al 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 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 h er 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 es 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 dD e c . 1 9 , 2 0 1 1 .* c i t e d b y examiner

7/29/2019 Us 8388829

5/56

US. Patent M a r . 5 , 2 0 1 3 S h e e t 1 0 f 3 1 US , 3 8 8 , 8 2 9 B2

rEd o ?. 0 m. 0 md n. 0 md md wd mQ N6 H. 0 m w w k m m v l o@ . 0g. 0 mg m w L g i m i w i i a y i g3. 0M@. 0 a0

0N

0

0

om

0Q

0 . 3

0

o 8

0

o m

0

e d

0 . 0 m

M 3 2 3 82 25 0. 8

3 2 3 8

0 . 0 3

5 . 8 3 5 8 8 3u .2 m .

p | a g A aueaapeluad luaojad

7/29/2019 Us 8388829

6/56

7/29/2019 Us 8388829

7/56


5 3 60 g0 8

v

N ;

E z c w w i8 5 12 5. 00 . 0

0 . 00 . 000U:1. 0. 0. 01 0 ; .

E0b m t m

7/29/2019 Us 8388829

8/56


o m

m m

0 Nww

0 . 0od. 0d6. ?P

m O > >6b a t m

u o g s m m o g spmspeed

7/29/2019 Us 8388829

9/56

7/29/2019 Us 8388829

10/56


0@ _ n _: 2 2> c o u:. .m0 :2 ;8. 828>w m l m o g ?5 3 %m3 9 MW- m r - w , $ q w u q q i o z"N Q E Z NuIM. 23 mmi g

0 . 00 . 0 . . 0 m. 0 md wp | a g A aueaapeluad

7/29/2019 Us 8388829

11/56

7/29/2019 Us 8388829

12/56

7/29/2019 Us 8388829

13/56


: o E m o n E o u2 3 84v

ov./vv /M y8 ./ 8%%%%84 8%a /%%a v //, . /4 %%8%%

J

1 %% ,0% ,% , .% ,0 % ,0%4 4w o%o /Qa c% ,4/ 9

_ O

.LHwN_

n .. 8 2 8 .W$ > o u w m2 2 0Om2 >8 6 . 5 %m2 3 2 6 s

mMm5WWiOMmmn

. . . .. . . .- 8 - 1 - 92

L .. . . . . .Sm c E m o b mu

7/29/2019 Us 8388829

14/56

US. Patent M a r . 5 , 2 0 1 3 S h e e t 1 0 0 f 3 1 US , 3 8 8 , 8 2 9 B2

7/29/2019 Us 8388829

15/56

7/29/2019 Us 8388829

16/56

7/29/2019 Us 8388829

17/56

Mar. , 2 0 1 3 S h e e t 1 3 0 f 3 1 US , 3 8 8 , 8 2 9 B 2S. P a t e n t

m w. U _ n _E E F E Fm. #mi n .aMO

._}c1 1 1 .. . .%. ;

w_$ 3 3 0 3 3 ;NM2 2 2 22 , :W E E Q E M5 6 E w

.w_w

o wm wl

5 3

m :

2 U

b m m v p0m . Q Qn _2

2 2 2 2 0 . ;v i i ?

7/29/2019 Us 8388829

18/56

US. Patent M a r . 5 , 2 0 1 3 S h e e t 1 4 0 f 3 1 US , 3 8 8 , 8 2 9 B2

2 0 4 5 5 2 23 6 9 5w p m c w w > x o w a

H8R U O N H( 5 W 4 S S E w ) P I Q M

7/29/2019 Us 8388829

19/56

7/29/2019 Us 8388829

20/56

7/29/2019 Us 8388829

21/56

7/29/2019 Us 8388829

22/56

7/29/2019 Us 8388829

23/56

7/29/2019 Us 8388829

24/56

7/29/2019 Us 8388829

25/56

7/29/2019 Us 8388829

26/56

7/29/2019 Us 8388829

27/56

7/29/2019 Us 8388829

28/56

7/29/2019 Us 8388829

29/56

7/29/2019 Us 8388829

30/56

7/29/2019 Us 8388829

31/56

7/29/2019 Us 8388829

32/56

7/29/2019 Us 8388829

33/56

7/29/2019 Us 8388829

34/56

7/29/2019 Us 8388829

35/56

7/29/2019 Us 8388829

36/56

7/29/2019 Us 8388829

37/56

7/29/2019 Us 8388829

38/56

7/29/2019 Us 8388829

39/56

7/29/2019 Us 8388829

40/56

7/29/2019 Us 8388829

41/56

7/29/2019 Us 8388829

42/56

7/29/2019 Us 8388829

43/56

7/29/2019 Us 8388829

44/56

7/29/2019 Us 8388829

45/56

7/29/2019 Us 8388829

46/56

7/29/2019 Us 8388829

47/56

7/29/2019 Us 8388829

48/56

7/29/2019 Us 8388829

49/56

7/29/2019 Us 8388829

50/56

7/29/2019 Us 8388829

51/56

7/29/2019 Us 8388829

52/56

7/29/2019 Us 8388829

53/56

7/29/2019 Us 8388829

54/56

7/29/2019 Us 8388829

55/56

7/29/2019 Us 8388829

56/56

Documents

Us 8388829