JP2011522899A - 気体アルカンを液体炭化水素へと変換するためのプロセス - Google Patents
気体アルカンを液体炭化水素へと変換するためのプロセス Download PDFInfo
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- JP2011522899A JP2011522899A JP2011513716A JP2011513716A JP2011522899A JP 2011522899 A JP2011522899 A JP 2011522899A JP 2011513716 A JP2011513716 A JP 2011513716A JP 2011513716 A JP2011513716 A JP 2011513716A JP 2011522899 A JP2011522899 A JP 2011522899A
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- Prior art keywords
- bromine
- catalyst
- reactor
- bromide
- metal
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 266
- 150000001335 aliphatic alkanes Chemical class 0.000 title claims abstract description 231
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 159
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 152
- 230000008569 process Effects 0.000 title claims abstract description 105
- 239000007788 liquid Substances 0.000 title description 32
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 457
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 303
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 221
- 239000003054 catalyst Substances 0.000 claims abstract description 203
- 239000000203 mixture Substances 0.000 claims abstract description 167
- 150000001347 alkyl bromides Chemical class 0.000 claims abstract description 109
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000007789 gas Substances 0.000 claims description 196
- 238000006243 chemical reaction Methods 0.000 claims description 171
- 229910052751 metal Inorganic materials 0.000 claims description 108
- 239000002184 metal Substances 0.000 claims description 105
- 150000004706 metal oxides Chemical class 0.000 claims description 69
- 239000004215 Carbon black (E152) Substances 0.000 claims description 64
- 229910044991 metal oxide Inorganic materials 0.000 claims description 61
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 50
- 150000003842 bromide salts Chemical class 0.000 claims description 47
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 34
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 31
- 239000010949 copper Substances 0.000 claims description 27
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 24
- 239000011777 magnesium Substances 0.000 claims description 24
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 22
- 229910052742 iron Inorganic materials 0.000 claims description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
- 239000011575 calcium Substances 0.000 claims description 21
- 229910052749 magnesium Inorganic materials 0.000 claims description 21
- 239000003345 natural gas Substances 0.000 claims description 21
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 20
- -1 VIB metals Chemical class 0.000 claims description 20
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 19
- 229910052759 nickel Inorganic materials 0.000 claims description 19
- 229910052791 calcium Inorganic materials 0.000 claims description 18
- 229910052802 copper Inorganic materials 0.000 claims description 18
- 238000012545 processing Methods 0.000 claims description 17
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 16
- 229910052697 platinum Inorganic materials 0.000 claims description 16
- 229910052719 titanium Inorganic materials 0.000 claims description 15
- 239000010936 titanium Substances 0.000 claims description 15
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- 229910052725 zinc Inorganic materials 0.000 claims description 15
- 239000011701 zinc Substances 0.000 claims description 15
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- 150000002739 metals Chemical class 0.000 claims description 14
- 229910052750 molybdenum Inorganic materials 0.000 claims description 14
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- 239000011651 chromium Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 11
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 11
- 229910052804 chromium Inorganic materials 0.000 claims description 11
- 229910017052 cobalt Inorganic materials 0.000 claims description 11
- 239000010941 cobalt Substances 0.000 claims description 11
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 11
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- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 10
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 239000011733 molybdenum Substances 0.000 claims description 10
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- 229910001507 metal halide Inorganic materials 0.000 claims description 9
- 150000005309 metal halides Chemical group 0.000 claims description 9
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 9
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- 239000011572 manganese Substances 0.000 claims description 8
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 7
- 230000002441 reversible effect Effects 0.000 claims description 7
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 7
- 239000010937 tungsten Substances 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052741 iridium Inorganic materials 0.000 claims description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052748 manganese Inorganic materials 0.000 claims description 6
- 229910052762 osmium Inorganic materials 0.000 claims description 6
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052703 rhodium Inorganic materials 0.000 claims description 6
- 239000010948 rhodium Substances 0.000 claims description 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 239000004332 silver Substances 0.000 claims description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000003949 liquefied natural gas Substances 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052758 niobium Inorganic materials 0.000 claims description 4
- 239000010944 silver (metal) Substances 0.000 claims description 4
- 229910052715 tantalum Inorganic materials 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- 239000003245 coal Substances 0.000 claims description 3
- 239000011275 tar sand Substances 0.000 claims description 3
- 239000002028 Biomass Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- NMJORVOYSJLJGU-UHFFFAOYSA-N methane clathrate Chemical compound C.C.C.C.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O NMJORVOYSJLJGU-UHFFFAOYSA-N 0.000 claims description 2
- 239000005416 organic matter Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract description 203
- 238000005893 bromination reaction Methods 0.000 abstract description 168
- 230000031709 bromination Effects 0.000 abstract description 136
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract description 91
- 150000001336 alkenes Chemical class 0.000 abstract description 58
- 229910001509 metal bromide Inorganic materials 0.000 description 114
- 239000007787 solid Substances 0.000 description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 70
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 58
- 239000001301 oxygen Substances 0.000 description 58
- 229910052760 oxygen Inorganic materials 0.000 description 58
- 230000015572 biosynthetic process Effects 0.000 description 47
- 239000000047 product Substances 0.000 description 43
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 42
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- 238000004519 manufacturing process Methods 0.000 description 33
- 229910052799 carbon Inorganic materials 0.000 description 31
- 230000003197 catalytic effect Effects 0.000 description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 30
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 29
- 230000002829 reductive effect Effects 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 238000010586 diagram Methods 0.000 description 28
- 239000012071 phase Substances 0.000 description 28
- 229940102396 methyl bromide Drugs 0.000 description 26
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 23
- 239000001569 carbon dioxide Substances 0.000 description 21
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- 238000007254 oxidation reaction Methods 0.000 description 19
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 18
- 238000011027 product recovery Methods 0.000 description 18
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 14
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- 239000002245 particle Substances 0.000 description 13
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- 239000003502 gasoline Substances 0.000 description 12
- 229910000000 metal hydroxide Inorganic materials 0.000 description 12
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- 239000000376 reactant Substances 0.000 description 12
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- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 8
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
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- 239000008346 aqueous phase Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
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- 150000001649 bromium compounds Chemical class 0.000 description 4
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- 238000001991 steam methane reforming Methods 0.000 description 4
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
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- 229910021575 Iron(II) bromide Inorganic materials 0.000 description 1
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- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
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- WMOHXRDWCVHXGS-UHFFFAOYSA-N [La].[Ce] Chemical compound [La].[Ce] WMOHXRDWCVHXGS-UHFFFAOYSA-N 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
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- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
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- 150000001768 cations Chemical class 0.000 description 1
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- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- MOOUSOJAOQPDEH-UHFFFAOYSA-K cerium(iii) bromide Chemical compound [Br-].[Br-].[Br-].[Ce+3] MOOUSOJAOQPDEH-UHFFFAOYSA-K 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
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- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
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- 238000010304 firing Methods 0.000 description 1
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- 238000007710 freezing Methods 0.000 description 1
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- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
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- 231100001261 hazardous Toxicity 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000008676 import Effects 0.000 description 1
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- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 239000012968 metallocene catalyst Substances 0.000 description 1
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
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- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
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- 239000011148 porous material Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
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Abstract
【選択図】図16
Description
本願は、2008年6月13日に出願された同時係属の、「Processes for Converting Gaseous Alkanes to Liquid Hydrocarbons」と題された米国特許出願第12/138,877号の一部継続出願であり、この米国特許出願第12/138,877号は、2008年4月30日に出願された同時継続の、「Process for Converting Gaseous Alkanes to Olefins」と題された米国特許出願第12/112,926号の一部継続出願であり、米国特許出願第12/112,926号は、2005年10月19日に出願された「Process for Converting Gaseous Alkanes to Olefins and Liquid Hydrocarbons」と題された米国特許出願第11/254,438号の継続出願であり、米国特許出願第11/254,438号は、2008年3月25日に発行され、「Process for Converting Gaseous Alkanes to Liquid Hydrocarbons」と題された米国特許第7,348,464号の一部継続出願であり、米国特許第7,348,464号は、2007年7月17日に発行され、「Process for Converting Gaseous Alkanes to Liquid Hydrocarbons」と題された米国特許第7,244,867号の一部継続出願である。
本発明は、低分子量アルカンを、燃料としてまたは燃料もしくは潤滑油および燃料添加剤などの化学物質の製造におけるモノマーおよび中間体として有用である可能性があるオレフィン、高分子量炭化水素またはその混合物に変換する方法に関し、より詳細には、1つまたは複数の実施形態において、低分子量アルカンを含むガスを臭素と反応させて、後の工程段階で耐えることができるレベルまで多臭素化種の生成を効果的に減少させるように臭化アルキルおよび臭化水素酸を生成させる方法に関する。
前述および他の目的を達成するため、また具体化され、本明細書で広く記述した本発明の目的に従って、本発明の1つの特徴は、臭化アルキルを含む臭素化生成物を生成するのに十分な第1の温度で、臭素をメタンを含む気体アルカンと接触させ、触媒の存在下で、臭化アルキル中に存在する多臭素化アルカンの少なくとも一部を一臭素化アルカンに変換するのに十分な第2の温度で、臭化アルキルをメタンの一部と反応させることを含む方法である。
気相臭素化反応のフリーラジカルメカニズムのため、ジブロモメタンおよび多少のトリブロモメタンならびに他の臭化アルキルも生成する。しかし、本発明の方法によるこの反応は、第1の反応器30で用いるアルカン対臭素比のため、臭化メチルへの比較的に高度な選択性でしばしば起こる。例えば、メタンの臭素化の場合、約6:1のメタン対臭素比が、滞留時間、温度および乱流混合などの反応条件によって、一ハロゲン化臭化メチルへの選択性を平均約88%に増加させると考えられる。これらの条件では、多少のジブロモメタンおよび検出可能限度に近い極めて少量のトリブロモメタンも臭素化反応において生成する可能性がある。2.6対1というより低いメタン対臭素比を用いる場合、一ハロゲン化臭化メチルへの選択性は、他の反応条件によって約65〜75%の範囲に低下する可能性がある。約2.5対1よりかなり低いメタン対臭素比では、臭化メチルへの許容できない低い選択性が発生し、さらに、望ましくないジブロモメタン、トリブロモメタンおよび炭素すすのかなりの生成が認められる。一ハロゲン化臭化メチルへのそのような選択性を達成するのに必要な第1の反応器30中の反応物の滞留時間は、比較的短く、断熱反応条件下では1〜5秒と短くてよい。エタン、プロパンおよびブタンなどのより高級なアルカンも臭素化することができ、結果として臭化エチル、臭化プロピルおよび臭化ブチルなどの一および多臭素化種が生ずる。さらに、いくつかの実施形態において、第1の反応器30に供給される乾燥臭素蒸気は、実質的に水を含まなくてよい。出願人は、少なくともいくつかの事例において、第1の反応器30中の臭素化段階から実質的にすべての水蒸気を排除することによって望ましくない二酸化炭素の生成が実質的になくなると思われるため、これが好ましい可能性があることを発見した。これが臭化アルキルへのアルカン臭素化の選択性を増加させる可能性があり、それにより、アルカンからの二酸化炭素の生成で発生する大量の廃熱がおそらくなくなる。
2)3HBr(g)+H2O=3H(+a)+3Br(−a)+H2O
3)3H(+a)+3Br(−a)+Fe(OH)3=Fe(+3a)+3Br(−a)+3H2O
管路19を経て第3の反応器16の出口から蒸気として出てくる元素状臭素および水および残存酸素または窒素(空気を酸化剤として用いる場合)を冷却器20で約0℃〜約70℃の範囲の温度およびほぼ環境大気圧から5バールまでの範囲の圧力で冷却して、臭素および水を凝縮させ、3相分離器22に通す。3相分離器22において、液体の水は、約3重量%程度の臭素に対する限られた溶解度を有するので、凝縮するさらなる臭素は、独立したより高密度の液体臭素相を形成する。しかし、液体臭素相は、0.1%未満程度の水に対する著しくより低い溶解度を有する。したがって、実質的に乾燥した臭素蒸気は、液体臭素および水を凝縮させ、単純な物理的分離によって水を傾斜し、その後、液体臭素を再蒸発させることによって容易に得ることができる。
気相臭素化反応のフリーラジカルメカニズムにより、ジブロモメタンおよび多少のトリブロモメタンならびに他の臭化アルキルも生成される。しかし、本発明の方法によるこの反応は、第1の反応器130で用いるアルカン対臭素比のため、臭化メチルへの比較的に高度な選択性でしばしば起こる。例えば、メタンの臭素化の場合、約6:1のメタン対臭素比が、滞留時間、温度および乱流混合などの反応条件によって、一ハロゲン化臭化メチルへの選択性を平均約88%に増加させると考えられる。これらの条件では、多少のジブロモメタンおよび検出可能限度に近い極めて少量のトリブロモメタンも臭素化反応において生成する可能性がある。約2.6対1というより低いメタン対臭素比を用いる場合、一ハロゲン化臭化メチルへの選択性は、他の反応条件によって約65〜75%の範囲に低下する可能性がある。約2.5対1よりかなり低いメタン対臭素比では、臭化メチルへの許容できない低い選択性が発生し、さらに、望ましくないジブロモメタン、トリブロモメタンおよび炭素すすのかなりの生成が認められる可能性がある。一ハロゲン化臭化メチルへのそのような選択性を達成するのに必要な第1の反応器130中の反応物の滞留時間は、比較的短く、断熱反応条件下では1〜5秒と短くてよい。エタン、プロパンおよびブタンなどのより高級なアルカンも臭素化することができ、結果として臭化エチル、臭化プロピルおよび臭化ブチルなどの一および多臭素化種が生ずる。さらに、いくつかの実施形態において、第1の反応器130に供給される乾燥臭素蒸気は、実質的に水を含まなくてよい。出願人は、少なくともいくつかの事例において、第1の反応器130中の臭素化段階から実質的にすべての水蒸気を排除することによって望ましくない二酸化炭素の生成が実質的になくなると思われるため、これが好ましい可能性があることを発見した。これが臭化アルキルへのアルカン臭素化の選択性を増加させる可能性があり、それにより、アルカンからの二酸化炭素の生成で発生する大量の廃熱がおそらくなくなる。
2)3HBr(g)+H2O=3H(+a)+3Br(−a)+H2O
3)3H(+a)+3Br(−a)+Fe(OH)3=Fe(+3a)+3Br(−a)+3H2O
金属臭化物が、不活性担体上に担持されたCu(II)Br2であり、水が主として蒸気として存在するより高い温度およびより低い圧力条件で作用する場合、反応は以下のとおりであると考えられる。
2)2Cu(I)Br+O2(g)=Br2(g)+2Cu(II)O
3)2HBr(g)+Cu(II)O=Cu(II)Br2+H2O(g)
第3の反応器117の出口から蒸気として出てくる元素状臭素および水および残存酸素または窒素(空気または酸素富化空気を酸化剤として用いる場合)を管路127を経て輸送し、交換器141の二次側および冷却器120で約0℃〜約70℃の範囲の温度に冷却して、臭素および水を凝縮させ、3相分離器122に通す。3相分離器122において、液体の水は、約3重量%程度の臭素に対する限られた溶解度を有するので、凝縮するさらなる臭素は、独立したより高密度の液体臭素相を形成する。しかし、液体臭素相は、0.1%未満程度の水に対する著しくより低い溶解度を有する。したがって、実質的に乾燥した臭素蒸気は、液体臭素および水を凝縮させ、単純な物理的分離によって水を傾斜し、その後、液体臭素を再蒸発させることによって容易に得ることができる。HBrは、水相中の臭素の混和性を増大させ、十分に高濃度では、単一3元液相を生じさせるので、凝縮した液体臭素および水中の有意な残存HBrを避けるように、HBrのほぼ完全な反応をもたらす条件で操作することが重要である。
気相臭素化反応のフリーラジカルメカニズムのため、ジブロモメタンおよび多少のトリブロモメタンならびに他の臭化アルキルも生成する。しかし、本発明の方法によるこの反応は、第1の反応器230で用いるアルカン対臭素比のため、臭化メチルへの比較的に高度な選択性でしばしば起こる。例えば、メタンの臭素化の場合、約6:1のメタン対臭素比が、滞留時間、温度および乱流混合などの反応条件によって、一ハロゲン化臭化メチルへの選択性を平均約80%に増加させると考えられる。これらの条件では、多少のジブロモメタンおよび検出可能限度に近い極めて少量のトリブロモメタンも臭素化反応において生成する可能性がある。約2.6対1というより低いメタン対臭素比を用いる場合、一ハロゲン化臭化メチルへの選択性は、他の反応条件によって約65〜75%の範囲に低下する可能性がある。約2.5対1よりかなり低いメタン対臭素比では、臭化メチルへの許容できない低い選択性が発生し、さらに、望ましくないジブロモメタン、トリブロモメタンおよび炭素すすのかなりの生成が認められる可能性がある。一ハロゲン化臭化メチルへのそのような選択性を達成するのに必要な第1の反応器230中の反応物の滞留時間は、比較的短く、断熱反応条件下では1〜5秒と短くてよい。エタン、プロパンおよびブタンなどのより高級なアルカンも臭素化することができ、結果として臭化エチル、臭化プロピルおよび臭化ブチルなどの一および多臭素化種が生ずる。さらに、いくつかの実施形態において、第1の反応器230に供給される乾燥臭素蒸気は、実質的に水を含まなくてよい。出願人は、少なくともいくつかの事例において、第1の反応器230中の臭素化段階から実質的にすべての水蒸気を排除することによって望ましくない二酸化炭素の生成が実質的になくなると思われるため、これが好ましい可能性があることを発見した。これが臭化アルキルへのアルカン臭素化の選択性を増加させ、それにより、アルカンからの二酸化炭素の生成で発生する大量の廃熱がおそらくなくなる可能性がある。
この反応によって生ずる水蒸気は、高分子炭化水素とともに管路244、218および216で開放弁219を経て熱交換器220に輸送し、熱交換器内で混合物が約0℃〜約70℃の範囲の温度に冷却する。この冷却した混合物を脱水装置250に送って、ガス流から実質的にすべての水を除去する。次いで、脱水装置250から管路253を経て水を除去する。オレフィン、高分子量炭化水素またはその混合物を含む乾燥ガス流を管路251を経て生成物回収ユニット252にさらに通して、オレフィン、C5+画分またはその混合物を液体生成物として管路254に回収する。当業者に公知であるような天然ガスまたは精製ガス流を処理し、オレフィン系炭化水素を回収するのに用いられるような、固層乾燥剤吸着の後の例えば、冷凍凝縮、低温膨張または循環吸収油または他の溶媒などの脱水および液体回収の従来の方法を本発明の実施において用いることができる。生成物回収ユニット252からの残存蒸気流出物は、工程用の燃料として用いることができるパージ流257と圧縮機258により圧縮されるリサイクル残存蒸気とに分割する。圧縮機258から放出されたリサイクル残存蒸気は、2つの画分に分割する。供給原料ガスの容積の少なくとも1.5倍に等しい第1の画分を、管路262を経て輸送し、管路225で運ばれる液体臭素および供給原料ガスと合わせて、熱交換器226に通して、液体臭素を蒸発させ、上述のような方法で第1の反応器230に供給する。管路262から管路263を経て抜き出す第2の画分を、変換率対選択性を最大にし、炭素の沈着に起因する触媒の不活性化の速度を最小にするために、反応器234への臭化アルキル濃度を希釈し、好ましくは約300℃〜約450℃の範囲の選択される操作温度に反応器234を維持するように反応熱を吸収するのに十分な率で制御弁260により調節する。したがって、リサイクル蒸気流出物によってもたらされる希釈は、第2の反応器234における温度を調節することに加えて、第1の反応器230における臭素化の選択性が制御されることを可能にする。
このように、実質的にHBrを含まない乾燥臭素蒸気が生成し、それにより、液体臭素から水および臭化水素を後に分離する必要がなくなる。反応器246は、600℃以下、より好ましくは約300℃〜約500℃で稼動させる。得られた臭素蒸気は、反応器246から管路247、弁248および管路242を経て熱交換器または冷却器221に輸送し、臭素を液体に凝縮させる。液体臭素を管路242を経て分離器222に輸送し、ポンプ224などの適切な手段により、液体臭素を管路225を経て除去し、管路225を経て熱交換器226および第1の反応器230に輸送する。残存空気または未反応酸素は、分離器222から管路227を経て、当業者により選択されるような適切な溶媒または適切な固体吸着剤を含むベンチュリスクラビングシステムなどのスクラビングユニット223に輸送し、残りの臭素を捕捉する。捕捉された臭素は、加熱または他の適切な手段によりスクラビング溶媒または吸着剤から脱離させ、そのように回収された臭素を管路212を経て管路225に輸送する。スクラビング済みの空気または酸素を、管路229を経て排出する。このように、窒素および他の実質的に非反応性成分は、本発明のシステムから除去され、それにより、当工程の炭化水素を含む部分に入ることが可能でない。また、周囲の環境への臭素の損失も避けられる。
このように、臭素を反応器320中で第2の金属臭化物、すなわち、2M2Brn+1として保存されるが、残存空気または酸素を含む得られた蒸気は、反応器320から管路324、弁326および管路318を経て排出される。
さらに、約200℃以上の温度で、ガス流に含まれる低分子量アルカンは、以下の一般反応(M2は金属を表す)により、酸化状態の固体金属臭化物の加熱された層上で反応して、気体臭化アルキル、臭化水素酸蒸気および還元状態の固体金属臭化物を生成する。
ガス流の温度およびしたがって酸化原子価状態の固相金属臭化物の層312の温度を制御することにより、第2の容器または反応器310中で臭素が遊離し、低分子量アルカンが臭素化される程度を制御することができる。低分子量アルカンが酸化状態の固体金属臭化物の加熱層上で反応して気体臭化アルキルを生成する正確なメカニズムは完全には理解されていないが、臭素化が金属臭化物の担体の固体表面上で起こり、それにより、反応が低温、例えば約200℃〜約300℃で進行することが可能になり、それにより、フリーラジカル気相臭素化が抑制され、多臭素化アルカンの生成が最小限になるということが出願人の確信である。
気相臭素化反応のフリーラジカルメカニズムのため、ジブロモメタンおよび多少のトリブロモメタンならびに他の臭化アルキルも生成され得る。用いるアルカン対臭素比のため、臭素化反応における臭素化は、臭化メチルへの比較的に高度な選択性でしばしば起こる。例えば、メタンの臭素化の場合、約6:1のメタン対臭素比が、滞留時間、温度および乱流混合などの反応条件によって、一ハロゲン化臭化メチルへの選択性を平均約88%に増加させると考えられる。これらの条件では、多少のジブロモメタンおよび検出可能限度に近い極めて少量のトリブロモメタンも臭素化反応において生成する可能性がある。約2.6対1というより低いメタン対臭素比を用いる場合、一ハロゲン化臭化メチルへの選択性は、他の反応条件によって約65〜75%の範囲に低下する可能性がある。約2.5対1よりかなり低いメタン対臭素比では、臭化メチルへの許容できない低い選択性が発生し、さらに、望ましくないジブロモメタン、トリブロモメタンおよび炭素すすのかなりの生成が認められる可能性がある。臭素化反応器で用いる比較的に高いメタン対臭素比は、臭素が臭素化反応器で実質的に消費されることも保証するものであり、それにより、元素状臭素が存在するため、本発明の方法の後の段階におけるフリーラジカル臭素化の後の発生を効果的に抑制するものである。一ハロゲン化臭化メチルへのそのような選択性を達成するのに必要な臭素化反応器中の反応物の滞留時間は、比較的短く、断熱反応条件下では1〜5秒と短くてよい。エタン、プロパンおよびブタンなどのより高級なアルカンも臭素化することができ、結果として臭化エチル、臭化プロピルおよび臭化ブチルなどの一および多臭素化種が生ずる。さらに、いくつかの実施形態において、臭素化反応器に供給される乾燥臭素蒸気は、実質的に水を含まなくてよい。出願人は、少なくともいくつかの事例において、臭素化段階から実質的にすべての水蒸気を排除することによって望ましくない二酸化炭素の生成が実質的になくなると思われるため、これが好ましい可能性があることを発見した。これが臭化アルキルへのアルカン臭素化の選択性を増加させ、それにより、アルカンからの二酸化炭素の生成で発生する大量の廃熱がおそらくなくなる可能性がある。
この反応は触媒なしに熱的に進行し得るが、そのような熱反応は、シフト反応器内の受け入れ難いほど長い滞留時間を必要とし、一臭素化アルカンへの十分な変換率を達成しないと判断された。したがって、シフト反応器は、VIII族金属、VIB族金属、IB族金属、アルミニウム、亜鉛、バナジウム、マグネシウム、カルシウム、チタン、イットリウム、ランタンまたはセリウムおよびそれらの混合物から選択される適切な触媒の層を含むことが好ましい。VIII族金属は、鉄、コバルト、ニッケル、白金、パラジウム、ロジウム、ルテニウム、イリジウム、オスミウムまたはそれらの2つ以上の混合物などである。VIB族金属は、タングステン、モリブデンまたはクロムなどである。IB族金属は、銅または銀などである。好ましくは、本発明のこの実施形態で用いるVIII族金属は、白金、パラジウム、ロジウム、ルテニウム、イリジウム、オスミウムまたはそれらの2つ以上の混合物から選択される貴金属であり、より好ましくはVIII族金属は、白金である。最も好ましくは、VIII族金属は、金属臭化物、金属酸化物または非化学量論的金属オキシ臭化物として用いられる鉄である。好ましくは、VIB族金属は、モリブデンまたはタングステンである。好ましくは、IB族金属は、金属臭化物、金属酸化物または金属オキシ臭化物として用いられる銅である。本発明の方法に用いられるような複数の熱的に可逆性の臭化物塩を形成する可能性がある上記の適切な金属触媒の非限定的な例は、鉄、モリブデン、タングステン、銅、バナジウム、クロムまたはそれらの2つ以上の混合物である。本発明の方法に用いられるような単一臭化物塩を形成する可能性がある上記の適切な触媒の非限定的な例は、コバルト、ニッケル、銀、亜鉛、マグネシウム、カルシウム、チタン、アルミニウム、ランタン、セリウムまたはそれらの2つ以上の混合物である。複数の熱的に可逆性の臭化物塩または単一臭化物塩を形成するこれらの金属は、シフト反応器において用いられる条件下では臭化水素酸との反応により臭化物塩に変換されるため、シフト反応器中で臭化物として存在し、機能すると思われるので、本発明の方法に最初に臭化物塩または酸化物として用いることができる。多臭素化アルカンの熱分解およびクラッキングを抑制するために比較的低い酸性度を有し、担体上の多臭素化アルカンの吸着を抑制するために比較的低い表面積を有するように、適切な担体が選択される。シフト反応器中で触媒とともに用いる適切な担体の非限定的な例は、好ましくは約50m2/g未満の比表面積を有する、シリカ、チタニア、ジルコニアまたは低表面積アルミナである。
この反応は触媒なしに熱的に進行し得るが、そのような熱反応は、シフト反応器410内の受け入れ難いほど長い滞留時間を必要とし、十分な変換を達成しないと判断され、したがって、シフト反応器410は、図10について上で述べたように選択した適切な触媒の層412を含むことが好ましい。シフト反応器410中で触媒を用いる場合、約250℃〜約570℃、より好ましくは約300℃〜約400℃で反応器を操作することが好ましい。熱交換器404は、この範囲内の所望の点へのシフト反応器410への熱投入量に応じて操作することができる。一臭素化アルカンと二または三臭素化アルカンとの著しく高い比率を含むシフト反応器410からの流出物は、管路231を経て抜き出し、第2の反応器234に流入する前に熱交換器232で約150℃〜450℃の範囲の温度に部分的に冷却する。第2の反応器234中で、臭化アルキルを適切な触媒の固定層233上で約250℃〜約500℃の範囲の温度および約1バール〜30バールの範囲の圧力で発熱的に反応させて、高分子量炭化水素およびさらなる臭化水素の混合物を得ることができる。本発明のこの実施形態において、反応器240および246は、図4および5に関して上述したようにサイクル式に操作することができ、反応器310および320は、図7および8に関して上述したようにサイクル式に操作することができる。
臭化アルキル、臭化水素、未反応臭素(bromne)および未反応アルカン(主としてメタン)を含む供給原料ガスの得られた混合物は、熱臭素化反応器から除去し、触媒シフト反応器に輸送することができる。触媒シフト反応器へのこの供給原料の温度は、約350℃〜約570℃、より好ましくは500℃〜約570℃、最も好ましくは530℃〜約570℃の範囲であってよい。熱臭素化反応は発熱的であるので、熱臭素化反応器に導入する供給原料ガスおよび臭素は、当業者に明らかなように、熱臭素化反応器の反応器操作条件を考慮して、熱臭素化反応器からの流出物が触媒シフト反応器に導入するための所望の範囲内にあることを保証するために、約300℃〜約500℃の範囲内の温度に加熱することができる。あるいは、熱臭素化反応器からの流出物混合物は、当業者に明らかな適切な手段により、触媒シフト反応器に用いる触媒と接触する前に約350℃〜約570℃の範囲内の温度に加熱または冷却することができる。
熱および触媒両反応器中の高温のため、元素状臭素は本質的に完全に変換される可能性がある。触媒シフト反応器に用いる触媒は、臭素(触媒表面上のジブロモメタンの解離吸着により供給される)とメタンとの選択的触媒反応により臭化メチルを生成するジブロモメタンとメタンとの選択的反応を促進すると考えられる。
臭化アルキル、臭化水素、未反応臭素および未反応アルカン(主としてメタン)を含む供給原料ガスの得られた混合物は、触媒シフト反応帯に流入する。
熱および触媒両反応器中の高温のため、臭素は本質的に完全に変換される。触媒シフト反応器に用いる触媒は、臭素(触媒表面上のジブロモメタンの解離吸着により供給される)とメタンとの選択的触媒反応により臭化メチルを生成するジブロモメタンとメタンとの選択的反応を促進すると考えられる。
未反応臭素、臭化アルキル、臭化水素、および未反応アルカン(主としてメタン)を含む供給原料ガスの得られた混合物は、その後、冷却し、分留塔に輸送することができ、分留塔中で多臭素化アルカン、例えば、二および三臭素化アルカンをこの混合物から除去する。そのような多臭素化アルカンを含む分留塔底液を、液中の重質の多臭素化アルカンから残存軽質モノブロモメタンをストリッピングする液の留分を蒸発させる、分留塔リボイラーに通す。これらの蒸気は、分留塔にリサイクルされる。次いで多臭素化アルカンを主としてメタンを含む供給原料ガスと合わせ、蒸発させ、約450℃〜約500℃の温度に予熱し、触媒シフト反応器に導入して、この反応器中で多臭素化アルカンをメタンと反応させて、主として一臭素化アルカンおよび臭化水素をさらに生成させる。臭化アルキルおよび臭化水素は、図1〜9に例示し、上で詳細に述べた本発明の方法の実施形態により、さらに処理するために触媒シフト反応器から合成反応器などに輸送することができる。分留塔内で多臭素化アルカンから分離された分留塔オーバーヘッド蒸気中の成分は、冷却器に送られてもよく、冷却器中で残存多臭素化アルカンが凝縮し、分留塔に還流されてもよい。主として臭化アルキルおよび臭化水素を含む残りの流れも図1〜9に例示し、上で詳細に述べた本発明の方法の実施形態により、さらに処理するために合成反応器などに輸送することができる。
熱および触媒両反応器中の高温のため、臭素は本質的に完全に変換される。触媒シフト反応器に用いる触媒は、臭素(触媒表面上のジブロモメタンの解離吸着により供給される)とメタンとの選択的触媒反応により臭化メチルを生成するジブロモメタンとメタンとの選択的反応を促進すると考えられる。
種々の混合物比率のメタンおよび蒸発臭素の混合物を、電熱素子を用いて3帯域において外部加熱されている非充填管型反応器を通して上方に垂直に流す。上部(出口)帯域は約494℃の平均温度に維持し、中間帯域は約450℃の平均温度に維持し、入口(予熱)帯域は約150℃〜約300℃の範囲にわたる種々の温度で操作する。反応滞留時間は、約2.0〜4.5秒の範囲であった。図14に示すように、臭素化反応器に導入したメタンと臭素とのモル比を2.5以上に増加させると、約70%の一臭素化選択性の有意な増加がもたらされる。約5のメタンと臭素とのモル比では、一臭素化選択性は平均約80%であるが、約10のメタンと臭素とのモル比では、一臭素化選択性は80%を超える。図15にさらに示すように、2.5以上のメタンと臭素との比でのこの高い一臭素化選択性は、4.8の比では約3.25秒、約5.2の比では約2秒という短い滞留時間で達成される。約2.5の好ましい最小比を下回る約2.1の低いメタンと臭素との比で測定したデータポイントの例の組では、反応器流出物中のCH3Br濃度は平均約16.8モル%であり、CH2Br2濃度は平均約6.8モル%であり、HBr濃度は好ましくないほど高く、平均約33.7モル%である。約2.5の好ましい最小比を少し上回る約2.6のメタンと臭素との比では、反応器流出物中のCH3Br濃度は平均約15.4モル%であり、CH2Br2濃度は平均約5モル%であり、HBr濃度は平均約26.4モル%である。約4.8のより好ましいメタンと臭素との比では、反応器流出物中のCH3Br濃度は平均約10.7モル%であり、CH2Br2濃度は平均約3.1モル%であり、HBr濃度は平均約16.8モル%である。
外部加熱式開管型(公称直径3/8インチ)実験室規模熱臭素化反応器(R−1a)を、本発明により約490℃および約650°h−1のGHSVで操作する公称直径1インチの触媒シフト反応器(R−1b)と直列で上流で操作する。メタン、臭素および窒素の流量は、第1の開管型熱臭素化反応器に対して3:1または2:1の標的供給原料CH4:Br2比に制御する。2つの標的CH4:Br2供給原料比混合物のそれぞれについて、第1の開管型熱臭素化反応器を加熱し(底部入口から425℃、450℃および470℃の上部出口までの3つの帯域温度プロファイルを有する)、開管型熱反応器中の熱気相フリーラジカル臭素化反応を開始させる。触媒シフト反応器の入口および出口ガスの試料の組成を、2種の標的メタン−臭素混合物について下の表に示す。熱臭素化を触媒シフト反応器の上流で開始させる場合、触媒シフト反応器への供給原料は、モノブロモメタン(MeBrまたはCH3Br)への比較的低い選択性およびジブロモメタン(DBMまたはCH2Br2)への比較的高い選択性を有するにもかかわらず、熱臭素化反応器中で生成したCH2Br2が触媒シフト反応器中の触媒上で過剰の未反応アルカン(メタン)と反応して、CH2Br2をCH3Brに変換し、モノブロモメタンのへ高い最終出口選択性が得られる(表1および2における結果を参照)。
外部加熱式実験室規模触媒シフト反応器(公称直径1インチ)を本発明により約490℃および約650h−1のGHSVで操作する。メタン、臭素および窒素の流量は、3:1の標的供給原料CH4:Br2比に制御し、第1の開管型熱臭素化反応器(R−1a)において約175℃に予熱し、触媒シフト反応器(R−1b)に供給する。
外部加熱式実験室規模触媒シフト反応器(公称直径1インチ)を本発明により種々の温度で、約650h−1のGHSVで操作する。メタン、臭素および窒素の流量は、3:1の標的供給原料CH4:Br2比に制御し、第1の開管型熱臭素化反応器(R−1a)において約175℃に予熱し、最初に490℃で操作する触媒シフト反応器(R−1b)に供給し、約125時間の期間にわたって安定化させる。プロットからわかるように、炭素効率はほぼ100%であり、490℃の初期操作温度でのCH3Br(MeBr)選択性は約80%である。約140時間において、触媒シフト反応器(R−1b)の温度は510℃に上昇し、これによりCH3Br選択性が約85%に増加し、ほぼ100%の炭素効率が維持されている。約155時間において、触媒シフト反応器(R−1b)の温度は520℃に上昇し、これによりCH3Br選択性が約88%に増加し、ほぼ100%の炭素効率が維持されている。約188時間において、触媒シフト反応器(R−1b)の温度は530℃に上昇し、これによりCH3Br選択性が約90%に増加し、ほぼ100%の炭素効率が維持されている。その後、約200時間後には、触媒シフト反応器(R−1b)の温度は約10℃きざみで上昇し、これによりCH3Br選択性が徐々に約570℃での約93%の最大値まで増加し、ほぼ100%の炭素効率が維持されている。約220時間後には、触媒シフト反応器(R−1b)の温度は580℃に上昇し、これによりCH3Br選択性のさらなる増加はもたらされないが、炭素効率のかなりの低下が認められ、好ましい触媒上の効率のよい反応のための最適温度は約580℃未満であることがわかる。
Claims (82)
- 少なくとも約2.5:1のメタン対臭素モル比で臭素を気相アルカンと接触させて、臭化アルキルを含む臭素化生成物を生成させる段階、および
前記臭化アルキルを触媒の存在下でC2+炭化水素と反応させて、該臭化アルキル中に存在する二臭素化アルカンおよび三臭素化アルカンの少なくとも一部を一臭素化アルカンに変換する段階、
を含む、方法。 - 前記メタン対臭素モル比が少なくとも約4:1である、請求項1に記載の方法。
- 前記メタン対臭素モル比が少なくとも約6:1である、請求項2に記載の方法。
- 前記C2+炭化水素が、エタン、プロパン、ブタン、ペンタンまたはその混合物である、請求項1に記載の方法。
- 前記触媒が、VIII族金属、VIB族金属、IB族金属、アルミニウム、亜鉛、バナジウム、マグネシウム、カルシウム、チタンおよびそれらの混合物からなる群から選択される、請求項1に記載の方法。
- 前記触媒が、鉄、コバルト、ニッケル、白金、パラジウム、ロジウム、ルテニウム、イリジウム、オスミウムおよびそれらの混合物からなる群から選択されるVIII族金属である、請求項5に記載の方法。
- 前記VIII族金属が白金である、請求項6に記載の方法。
- 前記触媒が、複数の熱的に可逆性の臭化物塩を形成する金属であり、鉄、モリブデン、タングステン、銅、バナジウム、クロムおよびそれらの混合物からなる群から選択される、請求項5に記載の方法。
- 前記触媒が、単一臭化物塩を形成する金属であり、コバルト、ニッケル、銀、亜鉛、マグネシウム、カルシウム、チタン、アルミニウムおよびそれらの混合物からなる群から選択される、請求項5に記載の方法。
- 前記触媒が担体上に分散している、請求項5に記載の方法。
- 前記担体がシリカである、請求項10に記載の方法。
- 前記気体アルカンが少なくとも90モル%のメタンを含む、請求項1に記載の方法。
- 前記C2+炭化水素を、前記接触させる段階の前に前記気体アルカンから除去する、請求項1に記載の方法。
- 低分子量アルカンからC2+アルカンを除去して、少なくとも約90モル%のメタンを含む供給原料ガスを得る段階、
該供給原料ガスを少なくとも約2.5:1のメタン対臭素モル比で臭素と反応させて、臭化アルキルを含む臭素化生成物を生成させる段階、および
該臭化アルキルを触媒の存在下でC2+炭化水素と反応させて、前記臭化アルキル中に存在する二臭素化アルカンおよび三臭素化アルカンの少なくとも一部を一臭素化アルカンに変換する段階、
を含む、方法。 - 前記臭化アルキルと反応させる前記C2+炭化水素が、前記低分子量アルカンから除去されたC2+アルカンの少なくとも一部である、請求項14に記載の方法。
- 前記メタン対臭素モル比が少なくとも約4:1である、請求項15に記載の方法。
- 前記メタン対臭素モル比が少なくとも約6:1である、請求項16に記載の方法。
- 前記C2+炭化水素が、エタン、プロパン、ブタン、ペンタンまたはその混合物である、請求項14に記載の方法。
- 前記触媒が、VIII族金属、VIB族金属、IB族金属、アルミニウム、亜鉛、バナジウム、マグネシウム、カルシウム、チタンおよびそれらの混合物からなる群から選択される、請求項14に記載の方法。
- 前記触媒が、鉄、コバルト、ニッケル、白金、パラジウム、ロジウム、ルテニウム、イリジウム、オスミウムおよびそれらの混合物からなる群から選択されるVIII族金属である、請求項19に記載の方法。
- 前記VIII族金属が白金である、請求項20に記載の方法。
- 前記触媒が、複数の熱的に可逆性の臭化物塩を形成する金属であり、鉄、モリブデン、タングステン、銅、バナジウム、クロムおよびそれらの混合物からなる群から選択される、請求項19に記載の方法。
- 前記触媒が、単一臭化物塩を形成する金属であり、コバルト、ニッケル、銀、亜鉛、マグネシウム、カルシウム、チタン、アルミニウムおよびそれらの混合物からなる群から選択される、請求項19に記載の方法。
- 前記触媒が担体上に分散している、請求項19に記載の方法。
- 前記担体がシリカである、請求項24に記載の方法。
- 臭素を第1の反応器中で約5秒未満の滞留時間で気体アルカンと反応させて、臭化アルキルを含む臭素化生成物を生成させる段階、および
該臭化アルキルを第2の反応器中で触媒の存在下でC2+炭化水素と反応させて、該臭化アルキル中に存在する二臭素化アルカンおよび三臭素化アルカンの少なくとも一部を一臭素化アルカンに変換する段階、
を含む、方法。 - 前記気体アルカンが少なくとも90モル%のメタンを含む、請求項26に記載の方法。
- 前記臭素と前記気体アルカンとを前記第1の反応器中で少なくとも約2.5:1のメタン対臭素モル比で反応させる、請求項27に記載の方法。
- 前記第2の反応器中の前記滞留時間が約5秒未満である、請求項28に記載の方法。
- 前記メタン対臭素モル比が少なくとも約4:1である、請求項28に記載の方法。
- 前記メタン対臭素モル比が少なくとも約6:1である、請求項28に記載の方法。
- 前記C2+炭化水素が、エタン、プロパン、ブタン、ペンタンまたはその混合物である、請求項26に記載の方法。
- 前記触媒が、VIII族金属、VIB族金属、IB族金属、アルミニウム、亜鉛、バナジウム、マグネシウム、カルシウム、チタンおよびそれらの混合物からなる群から選択される、請求項26に記載の方法。
- 前記触媒が、鉄、コバルト、ニッケル、白金、パラジウム、ロジウム、ルテニウム、イリジウム、オスミウムおよびそれらの混合物からなる群から選択されるVIII族金属である、請求項33に記載の方法。
- 前記VIII族金属が白金である、請求項34に記載の方法。
- 前記触媒が、複数の熱的に可逆性の臭化物塩を形成する金属であり、鉄、モリブデン、タングステン、銅、バナジウム、クロムおよびそれらの混合物からなる群から選択される、請求項33に記載の方法。
- 前記触媒が、単一臭化物塩を形成する金属であり、コバルト、ニッケル、銀、亜鉛、マグネシウム、カルシウム、チタン、アルミニウムおよびそれらの混合物からなる群から選択される、請求項33に記載の方法。
- 前記触媒が担体上に分散している、請求項33に記載の方法。
- 少なくとも90モル%のメタンを含む低分子量アルカンを炭化水素生成物から除去する段階、
該低分子量アルカンを少なくとも約2.5:1のメタン対臭素モル比で臭素と反応させて、臭化アルキルを含む臭素化生成物を生成させる段階、
該臭化アルキルを第1の触媒の存在下でC2+炭化水素と反応させて、該臭化アルキル中に存在する二臭素化アルカンおよび三臭素化アルカンの少なくとも一部を一臭素化アルカンに変換する段階、および
反応後の該臭化アルキルを第2の触媒の存在下で該C2+炭化水素と反応させて、該炭化水素生成物を生成させる段階、
を含む、方法。 - 前記低分子量アルカンを前記炭化水素生成物から除去した後に、前記C2+炭化水素を前記炭化水素生成物から除去する段階
をさらに含む、請求項39に記載の方法。 - 前記炭化水素生成物から除去されたC2+炭化水素を、前記臭化アルキルと反応させる前記段階に送る、請求項40に記載の方法。
- 前記メタン対臭素モル比が少なくとも約4:1である、請求項39に記載の方法。
- 前記メタン対臭素モル比が少なくとも約6:1である、請求項39に記載の方法。
- 前記C2+炭化水素が、エタン、プロパン、ブタン、ペンタンまたはその混合物である、請求項39に記載の方法。
- 前記第1の触媒が、VIII族金属、VIB族金属、IB族金属、アルミニウム、亜鉛、バナジウム、マグネシウム、カルシウム、チタンおよびそれらの混合物からなる群から選択される、請求項39に記載の方法。
- 前記第1の触媒が、鉄、コバルト、ニッケル、白金、パラジウム、ロジウム、ルテニウム、イリジウム、オスミウムおよびそれらの混合物からなる群から選択されるVIII族金属である、請求項45に記載の方法。
- 前記VIII族金属が白金である、請求項46に記載の方法。
- 前記第1の触媒が、複数の熱的に可逆性の臭化物塩を形成する金属であり、鉄、モリブデン、タングステン、銅、バナジウム、クロムおよびそれらの混合物からなる群から選択される、請求項45に記載の方法。
- 前記触媒が、単一臭化物塩を形成する金属であり、コバルト、ニッケル、銀、亜鉛、マグネシウム、カルシウム、チタン、アルミニウムおよびそれらの混合物からなる群から選択される、請求項45に記載の方法。
- 前記第1の触媒が担体上に分散している、請求項45に記載の方法。
- 前記第2の触媒が結晶性アルミノケイ酸塩触媒である、請求項39に記載の方法。
- 前記臭素化生成物が約30モル%未満の臭化水素酸をさらに含む、請求項1に記載の方法。
- 前記臭素化生成物が約30モル%未満の臭化水素酸をさらに含む、請求項14に記載の方法。
- 前記臭素化生成物が約30モル%未満の臭化水素酸をさらに含む、請求項26に記載の方法。
- 前記臭素化生成物が約30モル%未満の臭化水素酸をさらに含む、請求項39に記載の方法。
- 臭素を、臭化アルキルを含む臭素化生成物を生成するのに十分な第1の温度で、メタンを含む気体アルカンと反応させる段階、
該臭化アルキルを、触媒の存在下で、該臭化アルキル中に存在する多臭素化アルカンの少なくとも一部を一臭素化アルカンに変換するのに十分な第2の温度で、該メタンの一部と反応させる段階、
を含む、方法。 - 接触段階における前記メタン対臭素モル比が、約1.25:1を超えるが、7:1未満である、請求項56に記載の方法。
- 接触段階における前記メタン対臭素モル比が、約1.5:1を超えるが、4:1未満である、請求項57に記載の方法。
- 接触段階における前記メタン対臭素モル比が、約1.67:1を超えるが、3:1未満である、請求項58に記載の方法。
- 前記第1の温度が約300℃〜約600℃である、請求項56に記載の方法。
- 前記第2の温度が約350℃〜約570℃である、請求項56に記載の方法。
- 前記第2の温度が約500℃〜約570℃である、請求項61に記載の方法。
- 前記第2の温度が約530℃〜約570℃である、請求項62に記載の方法。
- 前記触媒が金属ハロゲン化物、金属オキシハロゲン化物またはその混合物である、請求項56に記載の方法。
- 前記金属がFe、Mo、La、Ce、W、Cr、Co、Ni、Cu、Ag、Zn、Mn、V、Nb、Ta、Ti、Y、Zr、Mg、Caまたはその混合物から選択される、請求項64に記載の方法。
- 前記ハロゲン化物がBr、ClおよびFから選択される、請求項64に記載の方法。
- 前記触媒が最初に金属酸化物として用いられるが、金属ハロゲン化物または金属オキシハロゲン化物に変換される、請求項56に記載の方法。
- 接触および反応段階が別々の反応器中で実施される、請求項56に記載の方法。
- 接触および反応段階が1つの反応器中で実施される、請求項56に記載の方法。
- 前記気体アルカンが少なくとも90モル%のメタンを含む、請求項56に記載の方法。
- 前記気体アルカンが約0.1モル%〜約10モル%のC2+炭化水素を含む、請求項56に記載の方法。
- 前記気体アルカンが約0.2モル%未満のC3+炭化水素を含む、請求項56に記載の方法。
- 前記気体アルカンが、天然ガス、炭床メタン、再ガス化液化天然ガス、ガスハイドレートおよび/またはクラスレート由来のガス、有機物またはバイオマスの嫌気的分解により得られるガス、タールサンドの処理で得られるガス、合成により生成される天然ガスまたはアルカン、あるいはこれらの源の混合物を源とするものである、請求項56に記載の方法。
- 前記気体アルカンが合成により生成されるアルカンを源とするものである、請求項56に記載の方法。
- 前記気体アルカンが合成により生成される天然ガスを源とするものである、請求項56に記載の方法。
- 前記気体アルカンがタールサンドの処理で得られるガスを源とするものである、請求項56に記載の方法。
- 前記臭化アルキル中に存在する多臭素化アルカンの少なくとも一部の一臭素化アルカンへの変換の後に前記臭化アルキルを第2の触媒の存在下で反応させて、臭化アルキルを生成させる段階
をさらに含む、請求項56に記載の方法。 - 臭素を、メタンを含む気体アルカンと接触させる段階、
該臭素と該気体アルカンとを、臭化アルキルを含む臭素化生成物を生成するのに十分な第1の温度で反応させる段階、および
該臭化アルキルを、触媒の存在下で、該臭化アルキルに存在する多臭素化アルカンの少なくとも一部を一臭素化アルカンに変換するのに十分な第2の温度で、該メタンの一部と反応させる段階
を含む方法。 - 前記臭素の少なくとも一部を前記気体アルカンとの接触時に蒸発させる、請求項78に記載の方法。
- 前記臭素および前記気体アルカンを、前記臭素と前記気体アルカンとを反応させる前記段階の前に、前記臭素の少なくとも一部を蒸発させるのに十分な温度に加熱する、請求項78に記載の方法。
- 前記臭素の少なくとも一部を、前記臭素と前記気体アルカンとを反応させる前記段階中に蒸発させる、請求項78に記載の方法。
- 供給原料ガスを前処理して、少なくとも90モル%のメタンを含む気体アルカンを得る段階、
臭素を、臭化アルキルを含む臭素化生成物を生成するのに十分な第1の温度で、該気体アルカンと反応させる段階、および
該臭化アルキルを、触媒の存在下で、該臭化アルキルに存在する多臭素化アルカンの少なくとも一部を一臭素化アルカンに変換するのに十分な第2の温度で、該メタンの一部と反応させる段階
を含む方法。
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CO6331460A2 (es) | 2011-10-20 |
AU2009257326A1 (en) | 2009-12-17 |
ZA201100099B (en) | 2012-05-01 |
BRPI0915356A2 (pt) | 2015-10-27 |
AR073342A1 (es) | 2010-11-03 |
KR20110030570A (ko) | 2011-03-23 |
AP2011005529A0 (en) | 2011-02-28 |
ECSP10010731A (es) | 2011-01-31 |
NZ589710A (en) | 2012-08-31 |
CA2726528A1 (en) | 2009-12-17 |
MX2010012314A (es) | 2010-12-02 |
US20090247796A1 (en) | 2009-10-01 |
WO2009152403A1 (en) | 2009-12-17 |
US8173851B2 (en) | 2012-05-08 |
EP2300398A1 (en) | 2011-03-30 |
CN102056867A (zh) | 2011-05-11 |
PE20110129A1 (es) | 2011-03-04 |
EA201170021A1 (ru) | 2011-06-30 |
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