US3773845A - Catalytic conversion of saturated hydrocarbons to higher and lower molecular weight hydrocarbons - Google Patents
Catalytic conversion of saturated hydrocarbons to higher and lower molecular weight hydrocarbons Download PDFInfo
- Publication number
- US3773845A US3773845A US00003306A US3773845DA US3773845A US 3773845 A US3773845 A US 3773845A US 00003306 A US00003306 A US 00003306A US 3773845D A US3773845D A US 3773845DA US 3773845 A US3773845 A US 3773845A
- Authority
- US
- United States
- Prior art keywords
- hydrocarbons
- disproportionation
- olefins
- reaction zone
- saturated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229930195734 saturated hydrocarbon Natural products 0.000 title abstract description 49
- 230000003197 catalytic effect Effects 0.000 title abstract description 28
- 229930195733 hydrocarbon Natural products 0.000 title description 47
- 150000002430 hydrocarbons Chemical class 0.000 title description 47
- 238000006243 chemical reaction Methods 0.000 title description 42
- 238000007323 disproportionation reaction Methods 0.000 abstract description 61
- 150000001336 alkenes Chemical class 0.000 abstract description 59
- 238000000034 method Methods 0.000 abstract description 48
- 230000008569 process Effects 0.000 abstract description 46
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 23
- 229910052751 metal Inorganic materials 0.000 abstract description 16
- 239000002184 metal Substances 0.000 abstract description 16
- 239000003054 catalyst Substances 0.000 description 30
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 24
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000002245 particle Substances 0.000 description 13
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- 150000001335 aliphatic alkanes Chemical class 0.000 description 8
- 239000001294 propane Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 230000006872 improvement Effects 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 6
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical group [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 6
- 229910052721 tungsten Inorganic materials 0.000 description 6
- 239000010937 tungsten Substances 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 235000013844 butane Nutrition 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 150000002736 metal compounds Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- -1 gaseous Chemical class 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 150000001349 alkyl fluorides Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000006069 physical mixture Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000001833 catalytic reforming Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/652—Chromium, molybdenum or tungsten
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
- C07C6/10—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond in hydrocarbons containing no six-membered aromatic rings
Definitions
- disproportionation is used herein to mean the conversion of hydrocarbons to new hydrocarbons of both higher and lower molecular weight.
- pentane may be disproportionated according to the reaction:
- the relatively high olefin concentration in the product from the reaction zone when operated at 875 F. versus the relatively low olefin concentration when operating at the lower temperatures illustrates the advantage of operating the saturated hydrocarbon disproportionation zone in the presence of no more than about 5 weight percent olefins and preferably substantially less olefins, as, for example, less than 1 weight percent olefins.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US330670A | 1970-01-16 | 1970-01-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3773845A true US3773845A (en) | 1973-11-20 |
Family
ID=21705176
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00003306A Expired - Lifetime US3773845A (en) | 1970-01-16 | 1970-01-16 | Catalytic conversion of saturated hydrocarbons to higher and lower molecular weight hydrocarbons |
Country Status (8)
Country | Link |
---|---|
US (1) | US3773845A (enrdf_load_stackoverflow) |
JP (1) | JPS4921088B1 (enrdf_load_stackoverflow) |
BE (1) | BE761206A (enrdf_load_stackoverflow) |
CA (1) | CA956654A (enrdf_load_stackoverflow) |
DE (1) | DE2101740C3 (enrdf_load_stackoverflow) |
FR (1) | FR2075370A5 (enrdf_load_stackoverflow) |
GB (1) | GB1319373A (enrdf_load_stackoverflow) |
NL (1) | NL172535C (enrdf_load_stackoverflow) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3856876A (en) * | 1971-01-21 | 1974-12-24 | Chevron Res | Disproportionation of saturated hydrocarbons employing a catalyst that comprises platinum and tungsten |
US3864417A (en) * | 1970-01-16 | 1975-02-04 | Chevron Res | Saturated hydrocarbon disproportionation at low temperatures |
US3914330A (en) * | 1969-10-08 | 1975-10-21 | Chevron Res | Process of averaging saturated hydrocarbons with a catalytic mass comprising a catalytic component for alkane dehydrogenation and a catalytic component for olefin averaging |
US4754099A (en) * | 1987-05-27 | 1988-06-28 | Shell Oil Company | Disproportionation of olefins |
US4956516A (en) * | 1988-05-20 | 1990-09-11 | Shell Oil Company | Disproportionation of olefins |
US4962263A (en) * | 1988-05-20 | 1990-10-09 | Shell Oil Company | Disproportionation of olefins |
WO2001016059A1 (en) * | 1999-09-02 | 2001-03-08 | Chevron U.S.A. Inc. | Process for conversion of well gas by disproportionation to saleable products |
US6225359B1 (en) | 1999-12-21 | 2001-05-01 | Chevron U.S.A. Inc. | Process for conversion of natural gas and associated light hydrocarbons to salable products |
US6472441B1 (en) | 2000-07-24 | 2002-10-29 | Chevron U.S.A. Inc. | Methods for optimizing Fischer-Tropsch synthesis of hydrocarbons in the distillate fuel and/or lube base oil ranges |
US6566568B1 (en) | 2001-12-19 | 2003-05-20 | Chevron U.S.A. Inc. | Molecular averaging of light and heavy hydrocarbons |
US6566569B1 (en) | 2000-06-23 | 2003-05-20 | Chevron U.S.A. Inc. | Conversion of refinery C5 paraffins into C4 and C6 paraffins |
US6573416B1 (en) * | 1999-11-19 | 2003-06-03 | Conocophillips Company | Hydrocarbon disproportionation |
US6806087B2 (en) | 2000-08-14 | 2004-10-19 | Chevron U.S.A. Inc. | Use of microchannel reactors in combinatorial chemistry |
US20070060781A1 (en) * | 2005-07-08 | 2007-03-15 | Goldman Alan S | Dual catalyst system for alkane metathesis |
US9446998B2 (en) | 2013-01-18 | 2016-09-20 | Chevron U.S.A. Inc. | Paraffinic jet and diesel fuels and base oils from vegetable oils via a combination of hydrotreating, paraffin disproportionation and hydroisomerization |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS50155291A (enrdf_load_stackoverflow) * | 1974-06-05 | 1975-12-15 | ||
JPS51108659U (enrdf_load_stackoverflow) * | 1975-02-27 | 1976-08-31 | ||
JPS51114088U (enrdf_load_stackoverflow) * | 1975-03-12 | 1976-09-16 | ||
JPS5217084A (en) * | 1975-07-30 | 1977-02-08 | Takaaki Hayashi | Oil-water relay |
JPS5222996A (en) * | 1975-08-14 | 1977-02-21 | Hideho Nishimura | Oil-runoff detecting device attached to tanks, etc. |
JPS53136194U (enrdf_load_stackoverflow) * | 1977-04-03 | 1978-10-27 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3392212A (en) * | 1964-12-21 | 1968-07-09 | Standard Oil Co | Process for producing dimethylbutane from pentane |
US3446868A (en) * | 1967-01-03 | 1969-05-27 | Phillips Petroleum Co | Disproportionation of propane |
US3484499A (en) * | 1967-11-13 | 1969-12-16 | Universal Oil Prod Co | Catalytic disproportionation of paraffinic hydrocarbons |
CA924736A (en) * | 1968-04-18 | 1973-04-17 | Y. Chen Nai | Disproportionation of aliphatic compounds |
-
1970
- 1970-01-16 US US00003306A patent/US3773845A/en not_active Expired - Lifetime
- 1970-10-27 CA CA096,715A patent/CA956654A/en not_active Expired
- 1970-11-20 JP JP45102616A patent/JPS4921088B1/ja active Pending
-
1971
- 1971-01-04 BE BE761206A patent/BE761206A/xx not_active IP Right Cessation
- 1971-01-08 FR FR7100563A patent/FR2075370A5/fr not_active Expired
- 1971-01-15 GB GB219171A patent/GB1319373A/en not_active Expired
- 1971-01-15 NL NLAANVRAGE7100588,A patent/NL172535C/xx not_active IP Right Cessation
- 1971-01-15 DE DE2101740A patent/DE2101740C3/de not_active Expired
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3914330A (en) * | 1969-10-08 | 1975-10-21 | Chevron Res | Process of averaging saturated hydrocarbons with a catalytic mass comprising a catalytic component for alkane dehydrogenation and a catalytic component for olefin averaging |
US3864417A (en) * | 1970-01-16 | 1975-02-04 | Chevron Res | Saturated hydrocarbon disproportionation at low temperatures |
US3856876A (en) * | 1971-01-21 | 1974-12-24 | Chevron Res | Disproportionation of saturated hydrocarbons employing a catalyst that comprises platinum and tungsten |
US4754099A (en) * | 1987-05-27 | 1988-06-28 | Shell Oil Company | Disproportionation of olefins |
US4956516A (en) * | 1988-05-20 | 1990-09-11 | Shell Oil Company | Disproportionation of olefins |
US4962263A (en) * | 1988-05-20 | 1990-10-09 | Shell Oil Company | Disproportionation of olefins |
WO2001016059A1 (en) * | 1999-09-02 | 2001-03-08 | Chevron U.S.A. Inc. | Process for conversion of well gas by disproportionation to saleable products |
US6573416B1 (en) * | 1999-11-19 | 2003-06-03 | Conocophillips Company | Hydrocarbon disproportionation |
US6225359B1 (en) | 1999-12-21 | 2001-05-01 | Chevron U.S.A. Inc. | Process for conversion of natural gas and associated light hydrocarbons to salable products |
US6566569B1 (en) | 2000-06-23 | 2003-05-20 | Chevron U.S.A. Inc. | Conversion of refinery C5 paraffins into C4 and C6 paraffins |
US6472441B1 (en) | 2000-07-24 | 2002-10-29 | Chevron U.S.A. Inc. | Methods for optimizing Fischer-Tropsch synthesis of hydrocarbons in the distillate fuel and/or lube base oil ranges |
US6649662B2 (en) | 2000-07-24 | 2003-11-18 | Chevron U.S.A. Inc. | Methods for optimizing fischer-tropsch synthesis of hydrocarbons in the distillate fuel and/or lube base oil ranges |
US6806087B2 (en) | 2000-08-14 | 2004-10-19 | Chevron U.S.A. Inc. | Use of microchannel reactors in combinatorial chemistry |
US6566568B1 (en) | 2001-12-19 | 2003-05-20 | Chevron U.S.A. Inc. | Molecular averaging of light and heavy hydrocarbons |
US20070060781A1 (en) * | 2005-07-08 | 2007-03-15 | Goldman Alan S | Dual catalyst system for alkane metathesis |
US7902417B2 (en) | 2005-07-08 | 2011-03-08 | The University Of North Carolina At Chapel Hill | Dual catalyst system for alkane metathesis |
US9446998B2 (en) | 2013-01-18 | 2016-09-20 | Chevron U.S.A. Inc. | Paraffinic jet and diesel fuels and base oils from vegetable oils via a combination of hydrotreating, paraffin disproportionation and hydroisomerization |
Also Published As
Publication number | Publication date |
---|---|
DE2101740C3 (de) | 1982-04-29 |
GB1319373A (en) | 1973-06-06 |
FR2075370A5 (enrdf_load_stackoverflow) | 1971-10-08 |
NL7100588A (enrdf_load_stackoverflow) | 1971-07-20 |
DE2101740B2 (de) | 1980-10-02 |
NL172535B (nl) | 1983-04-18 |
CA956654A (en) | 1974-10-22 |
DE2101740A1 (enrdf_load_stackoverflow) | 1971-09-23 |
NL172535C (nl) | 1983-09-16 |
BE761206A (fr) | 1971-06-16 |
JPS4921088B1 (enrdf_load_stackoverflow) | 1974-05-29 |
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