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United States Patent (10) Patent No.: US 7,173,160 B2 Maesen Et Al

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United States Patent (10) Patent No.: US 7,173,160 B2 Maesen Et Al US007 173160B2 (12) United States Patent (10) Patent No.: US 7,173,160 B2 Maesen et al. (45) Date of Patent: Feb. 6, 2007 (54) PROCESSES FOR CONCENTRATING 5,306,851 A 4, 1994 Wu et al. HIGHER DAMONDOIDS 5,334,368 A 8, 1994 Becket al. 5,414,189 A 5/1995 Chen et al. (75) Inventors: Theo Maesen, Point Richmond, CA 5.439,860 A 8, 1995 Habib et al. (US); Robert M. Carlson, Petaluma, 5,468.372 A 11/1995 Seamans et al. CA (US); Jeremy E. Dahl, Palo Alto, 5,495,283 A 2f1996 Cowe CA (US); Shenggao Liu, Hercules, CA 5,498,812 A 3, 1996 Bradway et al. (US); Hye Kyung C. Timken, Albany, 5,925,235 A 7/1999 Habib CA (US); Waqar R. Qureshi, San 6,013,239 A 1/2000 Chen et al. - s 6,179,995 B1 1/2001 Cash et al. Francisco, CA (US) 6,534,437 B2 3/2003 Eijsbouts et al. 6,743,290 B2 6/2004 Dahl et al. (73) Assignee: stron U.S.A. Inc., San Ramon, CA 2002/0134301 A1 9, 2002 Dahl et al. 2002.0137976 A1 9, 2002 Dahl et al. (*) Notice: Subject to any disclaimer, the term of this S.E. A. 1939: R past l S; listed under 35 2002/0147373 A1 10, 2002 Dahl et al. .S.C. 154(b) by ayS. 2002/0177743 A1 11, 2002 Dahl et al. 2002fO1881 63 A1 12/2002 Dahl et al. (21) Appl. No.: 10/622,185 2002fO193648 A1 12/2002 Dahl et al. 2003/OO97032 A1 5/2003 Dahl et al. (22) Filed: Jul. 16, 2003 2003. O100808 A1 5.2003 Dahl et al. (65) Prior Publication Data US 2004/0054243 A1 Mar. 18, 2004 FOREIGN PATENT DOCUMENTS FR 1547516 11, 1968 Related U.S. Application Data WO OO 14811 A1 T 2000 (60) Provisional application No. 60/396.991, filed on Jul. WO OOf 41810 A1 7, 2000 18, 2002. WO OO 42124 A1 T 2000 s WO OO 42125 A1 T 2000 (51) Int. Cl WO OO 42126 A1 T 2000 we WO OO/42127 A1 T 2000 C. 12 3.08: WO OO 42128 A1 T 2000 C07C 7700 (2006.015 WO O1/45071 A2 6, 2001 CIOG 47/00 (2006.01) (52) U.S. Cl. ...................... 585/352:585/258; 585/800; OTHER PUBLICATIONS 208/142: 208/107; 208/108; 208/109; 208/110; 208/112:208/143; 208/144; 208/145; 208/49; International Search Report from PCT/US03/22527 mailed Dec. 2, 208/78; 208/111.01 Fort,2003. Jr., et al.,al. AdAdamantane. Consequences ofof theth Diamondoidoid (58) Field of so S. 107.16. fi. Structure, Chem. Rev 64, 277-300 (1964). 208/112 143. 49 144 78 145 111 of Sandia National Laboratories (2000), World's First Diamond See application file fors completes - s search. history.. www.Sandia.gov.Micromachines Created at Sandia, Press Release, (Feb. 22, 2000) (56) References Cited Lin, et al., Natural Occurrence of Tetramantane (CHs), Pentamantane (CH) and Hexamantane (CoH) in a Deep U.S. PATENT DOCUMENTS Petroleum Reservoir, Fuel 74, (10): 1512-1521 (1995). Dahl, et al., Diamondoid Hydrocarbons as Indicators of Natural Oil 3,852,207 A 12/1974 Stangeland et al. Cracking, Nature, 54-57 (1999). 4,347,121 A 8/1982 Mayer et al. 4,401,556 A 8, 1983 Bezman et al. (Continued) 4,534,852 A 8, 1985 Washecheck et al. 4,556,646 A 12/1985 Bezman Primary Examiner Elizabeth D. Wood 4,820,402 A 4/1989 Partridge et al. (74) Attorney, Agent, or Firm—Buchanan Ingersoll & 4,913,799 A 4, 1990 Gortsema et al. Rooney PC 4.956,747 A 9, 1990 Beer et al. 4.956,748 A 9, 1990 Yamamoto (57) ABSTRACT 4.956,749 A 9/1990 Chang 4,982,049 A 1/1991 Alexander et al. 5,019,665 A 5/1991 Partridge et al. Hydroprocessing such as hydrocracking is advantageously 5,059,567 A 10, 1991 Linsten et al. employed in processes for the recovery and purification of 5,073,530 A 12/1991 Bezman et al. higher diamondoids from petroleum feedstocks. Hydroc 5,080,776 A 1/1992 Partridge et al. racking and other hydroprocesses degrade nondiamondoid 5,114,563 A 5, 1992 Lok et al. contaminants. 5, 120,899 A 6, 1992 Chen et al. 5, 198,203 A 3/1993 Kresge et al. 5,246,689 A 9, 1993 Beck et al. 31 Claims, 10 Drawing Sheets US 7,173,160 B2 Page 2 OTHER PUBLICATIONS Handbook of Petroleum Refining Processes, Second Edition, Robert McKervey, Synthetic Approaches to Large Diamondoid Hydrocar A. Myers, Editor, McGraw Hill (1997) 7.1 “MAK bons, Tetrahedron 36, 971-992 (1980). Moderate—Pressure Hydrocracking” by M.C. Hunter, et al, no Chung et al., Recent Development in High-Energy Density Liquid month. Fuels, Energy and Fuels 13, 641-649 (1999). Handbook of Petroleum Refining Processes, Second Edition, Robert Balaban et al., Systematic Classification and Nomenclature of Diamond Hydrocarbons-I, Tetrahedron 34, 3599-3606 (1978). A. Myers, Editor, McGraw Hill (1997) 7.2 “Chevron Rollman et al. Adamantane for Petroleum with Zeolites, Abstracts, Isocracking-Hydrocracking for Superior Fuel and Lubes Produc 210" ACS National Meeting, Chicago, IL. Aug. 20-24, 1995 Fuel, tion” by Alan C. Bridge, no month. pp. 1012-1017. Wingert, G.C.-M.S. Analysis of Diamondoid Hydrocarbons in Handbook of Petroleum Refining Processes, Second Edition, Robert Smackover Petroleums, Fuel 71, 38 (Jan. 1992). A. Myers, Editor, McGraw Hill (1997) 7.3 “UOP Unicracking U.S. Appl. No. 10/012,545 “Compositions Comprising Process for Hydrocracking” by Mark Reno, no month. Tetramantanes and Processes for Their Separation', filed Dec. 12, Handbook of Petroleum Refining Proceeses, Second Edition, Robert 2001, Inventors Dahl, et al. Beck, J.S., et al., “A New Family of Mesoporous Molecular Sieves A. Myers, Editor, McGraw Hill (1997) 8.1 “Chevron RDS/VRDS Prepared with Liquid Crystal Templates'. J. Am. Chem. Soc. Hydrotreating” by David N. Brossard, no month. 114: 10834-10843 (1992), no month. Handbook of Petroleum Refining Processes, Second Edition, Robert Inoue, Yoshimasa, et al., “Improved Ni-Mo HDN Catalysts through Increased Dispersion and Intrinsic Activity of the Active Phase'. A. Myers, Editor, McGraw Hill (1997) 8.4 “UOP RCD Unionfining Science and Technology in Catalysis, Kodansha Ltd., Tokyo, Japan, Process” by Gregory J. Thompson, no month. pp. 415-418 (1998), no month. Kresge, et al., Nature 359:710 (1992), no month. U.S. Patent Feb. 6, 2007 Sheet 1 of 10 US 7,173,160 B2 Figure 1 100 Make-Up /16 Hydrogen 28 Product Gas - 38 Fresh Feed / 12 Recycle Fraction 1 10 -1 Gas / 26 24 Fraction 2 14N - / / Fraction 3 22 - Fraction 4 20 1. * 18 30 Fraction 5 U.S. Patent Feb. 6, 2007 Sheet 2 of 10 US 7,173,160 B2 Figure 2 /1 200 16 Make-UpHydrogen / Make-Up Hydrogen /50 --> Recycle 16 N Product Gas Fresh Feed -28 10 u-12 Sycle Fraction 1 42 / Fraction 2 32 40 14 Fraction 3 ( N Fraction 4 First-Stage Second-Stage Product N Product 64 U.S. Patent Feb. 6, 2007 Sheet 3 of 10 US 7,173,160 B2 Figure 3 /1 300 Make-Up Hyd 74 ake-Up Hydrogen / - 28 Product 1 Gas 16 10 Fresh Feed \ -2 -Ha Hydrocracking Recycle 16 Reactor Gas 4. Fraction 1 68 N. -12 42 / Fraction 2 / 14% 26 3 - 40Fraction 3 res N / - N 20 Fraction 4 / 18 34 Hydrotreating -72 M Reactor Here 30 -36 76 / / Fraction 5 Recycle U.S. Patent Feb. 6, 2007 Sheet 4 of 10 US 7,173,160 B2 Figure 4 400 Hydrogen 62 Feed - 22 40 20 30 U.S. Patent Feb. 6, 2007 Sheet S of 10 US 7,173,160 B2 Figure 5 T-2 2OOOOOO Feedstock for 16OOOOO HCR Reaction 12OOOOO Crude Oil Contaminant 8OOOOO 4OOOOO T-2 24OOOOO Light 2000000 Hydrocarbons Product of HCR Reaction at 800 F 16OOOOO Diamantane T-3 12OOOOO Triamantane Pentamantanes Crude Oil Contaminant - - - 5.00 1000 1500 2000 2500 3000 T-2 28OOOOO Light 2400000 Hydrocarbons Product of HCR 2OOOOOO Diamantane -1 Reaction at 850 of 16OOOOO Triannantane T-3 Pentamantanes& 12OOOOO Cyclohexamantane 1OOOOOO 8OOOOO / Hexamantanes & 6OOOOO Cycloheptamantanes 4OOOOO -1 2OOOOO 5.OO 1000 1500 T2000 2500 30, OO GCMS Time (min.) --> U.S. Patent Feb. 6, 2007 Sheet 6 of 10 US 7,173,160 B2 Figure 6 50 - 45 - 35 - we30 E. Feedstock igh 25 Fr 4 & 5 t (combined) 20 15 R Product HCR (a) 850 F IBP - 150 - 250 - 350 - 450 - 550 - 650 - 750 - 850 - 950 - 150 250 350 450 550 650 750 850 950 1050 Distillation Cuts (F) U.S. Patent Feb. 6, 2007 Sheet 7 of 10 US 7,173,160 B2 Figure 7 4.00 12 hours 3.50 g 3.00 3) 24 hours | 2.50 1 23 2.00 48 hours 108 hours Te 150 Starting -- tr 3. 1.00 O.50 O.OO T - - - - - OOO 5.00 10.00 15.00 20.00 25.00 3OOO Tetramantanes | Hydrocarbon U.S. Patent Feb. 6, 2007 Sheet 8 of 10 US 7,173,160 B2 Figure 8 Tetramantanes Hydrocarbon impurities 121) lo 500000 Ab FEED U 400000 300000 nC 200000 100000 O so too Tetramantanes (1(2)3 (121 1300000 O 11OOOOO Ab U 900000 PRODUCT da Hydrocarbon impurities 700000 C e 5OOOOO 3OOOOO 100000 ---- ol 6.00 700 s.00 g.o.o. 10.001100 T 1200 1300 T 1400 T. GCMS Time (min.) --> U.S. Patent Feb. 6, 2007 Sheet 9 of 10 US 7,173,160 B2 Figure 9 FEED PRODUCT U.S.
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