CA2586326A1 - Fabrication d'hydrocarbures superieurs a partir du methane, via l'acide sulfonique de methane, le sulfene et d'autres voies - Google Patents

Fabrication d'hydrocarbures superieurs a partir du methane, via l'acide sulfonique de methane, le sulfene et d'autres voies Download PDF

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Publication number: CA2586326A1
Authority: CA; Canada
Prior art keywords: sulfene; msa; methane; reaction; catalysts
Prior art date: 2003-11-05
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.): Abandoned

Application number

CA002586326A

Other languages

English (en)

Inventor

Alan K. Richards

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

2003-11-05

Filing date

2004-11-05

Publication date

2005-05-19

2003-11-05 Priority claimed from PCT/US2003/035396 external-priority patent/WO2004041399A2/fr

2004-06-21 Priority claimed from PCT/US2004/019977 external-priority patent/WO2005069751A2/fr

2004-11-05 Application filed by Individual filed Critical Individual

2005-05-19 Publication of CA2586326A1 publication Critical patent/CA2586326A1/fr

Status Abandoned legal-status Critical Current

Links

LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 title claims abstract description 154
238000004519 manufacturing process Methods 0.000 title claims abstract description 34
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 title claims description 391
229940098779 methanesulfonic acid Drugs 0.000 title claims description 197
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title abstract description 169
230000037361 pathway Effects 0.000 title abstract description 74
150000002430 hydrocarbons Chemical class 0.000 title abstract description 28
229930195733 hydrocarbon Natural products 0.000 title abstract description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 92
239000007788 liquid Substances 0.000 claims description 73
150000001875 compounds Chemical class 0.000 claims description 72
238000000034 method Methods 0.000 claims description 72
-1 methyl-methanesulfonate ester Chemical class 0.000 claims description 58
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 50
230000015572 biosynthetic process Effects 0.000 claims description 32
239000005977 Ethylene Substances 0.000 claims description 30
150000001336 alkenes Chemical class 0.000 claims description 28
239000003795 chemical substances by application Substances 0.000 claims description 16
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 15
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 15
150000001335 aliphatic alkanes Chemical class 0.000 claims description 14
238000012546 transfer Methods 0.000 claims description 14
239000000446 fuel Substances 0.000 claims description 12
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 7
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 claims description 4
239000012024 dehydrating agents‎ Substances 0.000 claims 3
239000012048 reactive intermediate Substances 0.000 claims 2
239000002253 acid Substances 0.000 abstract description 21
238000006243 chemical reaction Methods 0.000 description 137
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 120
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 100
239000003054 catalyst Substances 0.000 description 95
239000000463 material Substances 0.000 description 64
239000007789 gas Substances 0.000 description 55
150000003254 radicals Chemical class 0.000 description 41
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
230000003197 catalytic effect Effects 0.000 description 37
125000004435 hydrogen atom Chemical group [H]* 0.000 description 37
238000012545 processing Methods 0.000 description 35
239000000543 intermediate Substances 0.000 description 32
150000008064 anhydrides Chemical class 0.000 description 31
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239000007787 solid Substances 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
239000003153 chemical reaction reagent Substances 0.000 description 24
239000000047 product Substances 0.000 description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 description 23
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 21
238000005755 formation reaction Methods 0.000 description 21
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
229910052799 carbon Inorganic materials 0.000 description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 18
229910021536 Zeolite Inorganic materials 0.000 description 17
239000003999 initiator Substances 0.000 description 17
229920000642 polymer Polymers 0.000 description 17
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 16
238000013459 approach Methods 0.000 description 15
125000004430 oxygen atom Chemical group O* 0.000 description 15
239000004215 Carbon black (E152) Substances 0.000 description 13
125000004429 atom Chemical group 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
238000006555 catalytic reaction Methods 0.000 description 12
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
239000002699 waste material Substances 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 11
150000001721 carbon Chemical group 0.000 description 11
229910002092 carbon dioxide Inorganic materials 0.000 description 11
238000010438 heat treatment Methods 0.000 description 11
238000005336 cracking Methods 0.000 description 10
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 10
150000002500 ions Chemical class 0.000 description 10
229910052760 oxygen Inorganic materials 0.000 description 10
239000001301 oxygen Substances 0.000 description 10
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238000012360 testing method Methods 0.000 description 10
238000011144 upstream manufacturing Methods 0.000 description 10
241000269350 Anura Species 0.000 description 9
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
238000005094 computer simulation Methods 0.000 description 9
238000006297 dehydration reaction Methods 0.000 description 9
230000001976 improved effect Effects 0.000 description 9
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
239000006227 byproduct Substances 0.000 description 8
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
230000002378 acidificating effect Effects 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
230000004888 barrier function Effects 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
238000003780 insertion Methods 0.000 description 7
230000037431 insertion Effects 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
AVFBYUADVDVJQL-UHFFFAOYSA-N phosphoric acid;trioxotungsten;hydrate Chemical compound O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O AVFBYUADVDVJQL-UHFFFAOYSA-N 0.000 description 7
125000004434 sulfur atom Chemical group 0.000 description 7
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000001569 carbon dioxide Substances 0.000 description 6
230000018044 dehydration Effects 0.000 description 6
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229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
230000003647 oxidation Effects 0.000 description 6
230000003389 potentiating effect Effects 0.000 description 6
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
239000010703 silicon Substances 0.000 description 6
239000000758 substrate Substances 0.000 description 6
229910052720 vanadium Inorganic materials 0.000 description 6
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
230000003466 anti-cipated effect Effects 0.000 description 5
238000009835 boiling Methods 0.000 description 5
238000012993 chemical processing Methods 0.000 description 5
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239000003502 gasoline Substances 0.000 description 5
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HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 5
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239000011148 porous material Substances 0.000 description 5
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239000011593 sulfur Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
229910006069 SO3H Inorganic materials 0.000 description 4
230000001588 bifunctional effect Effects 0.000 description 4
150000001924 cycloalkanes Chemical class 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
150000002561 ketenes Chemical class 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000002243 precursor Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000012552 review Methods 0.000 description 4
238000001179 sorption measurement Methods 0.000 description 4
241000894007 species Species 0.000 description 4
150000003464 sulfur compounds Chemical class 0.000 description 4
230000008093 supporting effect Effects 0.000 description 4
230000007704 transition Effects 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
238000005727 Friedel-Crafts reaction Methods 0.000 description 3
101150101537 Olah gene Proteins 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
BBCNJOQVGLSOGV-UHFFFAOYSA-N [O].[Si].[S] Chemical compound [O].[Si].[S] BBCNJOQVGLSOGV-UHFFFAOYSA-N 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
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229910000071 diazene Inorganic materials 0.000 description 3
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125000005842 heteroatom Chemical group 0.000 description 3
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239000002808 molecular sieve Substances 0.000 description 3
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URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
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238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/868—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains sulfur as hetero-atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
- C07C1/322—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom the hetero-atom being a sulfur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/20—C2-C4 olefins
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/22—Higher olefins
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/40—Ethylene production

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA002586326A 2003-11-05 2004-11-05 Fabrication d'hydrocarbures superieurs a partir du methane, via l'acide sulfonique de methane, le sulfene et d'autres voies Abandoned CA2586326A1 (fr)

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
USPCT/US03/35396		2003-11-05
PCT/US2003/035396 WO2004041399A2 (fr)	2002-11-05	2003-11-05	Conversion anhydre de methane et d'autres alcanes legers en methanol et d'autres derives au moyen de trajets de radicaux et de reactions en chaine produisant un minimum de dechets
US56267504P	2004-04-15	2004-04-15
US60/562,675		2004-04-15
PCT/US2004/019977 WO2005069751A2 (fr)	2003-06-21	2004-06-21	Traitement anhydre de methane en acide methanesulfonique, methanol, et autres composes
USPCT/US04/19977		2004-06-21
PCT/US2004/036831 WO2005044789A1 (fr)	2003-11-05	2004-11-05	Fabrication d'hydrocarbures superieurs a partir du methane, via l'acide sulfonique de methane, le sulfene, et d'autres voies

Publications (1)

Publication Number	Publication Date
CA2586326A1 true CA2586326A1 (fr)	2005-05-19

Family

ID=34577497

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002586326A Abandoned CA2586326A1 (fr)	2003-11-05	2004-11-05	Fabrication d'hydrocarbures superieurs a partir du methane, via l'acide sulfonique de methane, le sulfene et d'autres voies

Country Status (6)

Country	Link
EP (1)	EP1720831A4 (fr)
CA (1)	CA2586326A1 (fr)
MX (1)	MXPA06005141A (fr)
NO (1)	NO20062578L (fr)
OA (1)	OA13283A (fr)
WO (1)	WO2005044789A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20070282151A1 (en) *	2006-05-19	2007-12-06	Richards Alan K	Manufacture of higher hydrocarbons from methane, via methanesulfonic acid, sulfene, and other pathways
FR3077817B1 (fr) *	2018-02-14	2020-02-28	Arkema France	Procede de synthese industrielle en continu d'acide alcane-sulfonique

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2553576A (en) *	1947-03-26	1951-05-22	Houdry Process Corp	Production of organic compounds from methane sulfonic acid
US5292947A (en) *	1992-09-28	1994-03-08	Eastman Kodak Company	Process for preparing alkylsulfonic anhydrides

2004
- 2004-11-05 MX MXPA06005141A patent/MXPA06005141A/es active IP Right Grant
- 2004-11-05 WO PCT/US2004/036831 patent/WO2005044789A1/fr active Application Filing
- 2004-11-05 EP EP04810350A patent/EP1720831A4/fr not_active Withdrawn
- 2004-11-05 CA CA002586326A patent/CA2586326A1/fr not_active Abandoned
- 2004-11-05 OA OA1200600148A patent/OA13283A/en unknown
2006
- 2006-06-02 NO NO20062578A patent/NO20062578L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
MXPA06005141A (es)	2007-01-26
EP1720831A1 (fr)	2006-11-15
OA13283A (en)	2007-01-31
EP1720831A4 (fr)	2010-04-07
WO2005044789A1 (fr)	2005-05-19
NO20062578L (no)	2006-06-02

Publication	Publication Date	Title
US20070282151A1 (en)	2007-12-06	Manufacture of higher hydrocarbons from methane, via methanesulfonic acid, sulfene, and other pathways
US7282603B2 (en)	2007-10-16	Anhydrous processing of methane into methane-sulfonic acid, methanol, and other compounds
US20080161591A1 (en)	2008-07-03	Anhydrous processing of methane into methane-sulfonic acid, methanol, and other compounds
Kosinov et al.	2020	Reactivity, selectivity, and stability of zeolite‐based catalysts for methane dehydroaromatization
Zhang et al.	2020	Applications of zeolites to C1 chemistry: recent advances, challenges, and opportunities
JP5051924B2 (ja)	2012-10-17	メタン転換製造プロセス
CA2136626C (fr)	2000-10-03	Production d'olefines de grande purete
CA2504707C (fr)	2019-07-09	Conversion anhydre de methane et d'autres alcanes legers en methanol et d'autres derives au moyen de trajets de radicaux et de reactions en chaine produisant un minimum de dechets
WO2008157044A1 (fr)	2008-12-24	Procédés de production d'hydrocarbures supérieurs à partir de méthane
Corral Valero et al.	2013	Cobalt catalyzed Fischer–Tropsch synthesis: perspectives opened by first principles calculations
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