CA2439571A1 - Method and apparatus for the preparation of triptane and/or triptene - Google Patents
Method and apparatus for the preparation of triptane and/or triptene Download PDFInfo
- Publication number
- CA2439571A1 CA2439571A1 CA002439571A CA2439571A CA2439571A1 CA 2439571 A1 CA2439571 A1 CA 2439571A1 CA 002439571 A CA002439571 A CA 002439571A CA 2439571 A CA2439571 A CA 2439571A CA 2439571 A1 CA2439571 A1 CA 2439571A1
- Authority
- CA
- Canada
- Prior art keywords
- reactor
- reaction
- methanol
- catalyst
- product
- 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.)
- Abandoned
Links
- ZISSAWUMDACLOM-UHFFFAOYSA-N triptane Chemical compound CC(C)C(C)(C)C ZISSAWUMDACLOM-UHFFFAOYSA-N 0.000 title claims abstract description 152
- 238000000034 method Methods 0.000 title claims abstract description 108
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 title claims abstract description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 340
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims abstract description 200
- 238000006243 chemical reaction Methods 0.000 claims abstract description 137
- 239000003054 catalyst Substances 0.000 claims abstract description 90
- 239000007791 liquid phase Substances 0.000 claims abstract description 78
- -1 zinc halide Chemical class 0.000 claims abstract description 72
- 239000012071 phase Substances 0.000 claims abstract description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 66
- 239000011701 zinc Substances 0.000 claims abstract description 65
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 65
- 238000000926 separation method Methods 0.000 claims abstract description 63
- 239000007790 solid phase Substances 0.000 claims abstract description 18
- 238000010924 continuous production Methods 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- 230000000717 retained effect Effects 0.000 claims abstract description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 87
- 150000002430 hydrocarbons Chemical class 0.000 claims description 87
- 239000000047 product Substances 0.000 claims description 78
- 239000000203 mixture Substances 0.000 claims description 61
- 239000004215 Carbon black (E152) Substances 0.000 claims description 52
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 28
- 239000007795 chemical reaction product Substances 0.000 claims description 26
- 239000000376 reactant Substances 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 238000004821 distillation Methods 0.000 claims description 18
- 230000002209 hydrophobic effect Effects 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 238000010438 heat treatment Methods 0.000 claims description 15
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 14
- 238000005984 hydrogenation reaction Methods 0.000 claims description 14
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 claims description 8
- 150000005172 methylbenzenes Chemical class 0.000 claims description 8
- 238000011027 product recovery Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 7
- 150000001491 aromatic compounds Chemical class 0.000 claims description 6
- BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 3
- 239000003254 gasoline additive Substances 0.000 claims description 2
- 150000002390 heteroarenes Chemical class 0.000 claims description 2
- 239000012263 liquid product Substances 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- 229940102001 zinc bromide Drugs 0.000 claims 1
- 239000007788 liquid Substances 0.000 description 29
- 239000007789 gas Substances 0.000 description 24
- 239000002585 base Substances 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 230000035484 reaction time Effects 0.000 description 11
- 238000002156 mixing Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 239000001273 butane Substances 0.000 description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- OGQDIIKRQRZXJH-UHFFFAOYSA-N protriptyline hydrochloride Chemical group [Cl-].C1=CC2=CC=CC=C2C(CCC[NH2+]C)C2=CC=CC=C21 OGQDIIKRQRZXJH-UHFFFAOYSA-N 0.000 description 6
- 238000013019 agitation Methods 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 230000000737 periodic effect Effects 0.000 description 5
- 229910052707 ruthenium Inorganic materials 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000003751 zinc Chemical class 0.000 description 3
- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,4-dimethylpentane Chemical compound CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 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
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000011143 downstream manufacturing Methods 0.000 description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- WGECXQBGLLYSFP-UHFFFAOYSA-N (+-)-2,3-dimethyl-pentane Natural products CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 1
- NVOWAVFZSKWQPR-DYKTZABPSA-N (1r,3s,3ar,5s,8z,12r,12ar)-1,3,12-trihydroxy-3,8,12-trimethyl-5-propan-2-yl-1,2,3a,5,6,7,11,12a-octahydrocyclopenta[11]annulene-4,10-dione Chemical compound O=C1[C@H](C(C)C)CC\C(C)=C/C(=O)C[C@@](C)(O)[C@H]2[C@H](O)C[C@](C)(O)[C@@H]21 NVOWAVFZSKWQPR-DYKTZABPSA-N 0.000 description 1
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Natural products CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 1
- AEXMKKGTQYQZCS-UHFFFAOYSA-N 3,3-dimethylpentane Chemical compound CCC(C)(C)CC AEXMKKGTQYQZCS-UHFFFAOYSA-N 0.000 description 1
- 101150034533 ATIC gene Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- MHWMGZXEOTUNBI-UHFFFAOYSA-N C[Zn].[Zn] Chemical compound C[Zn].[Zn] MHWMGZXEOTUNBI-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical group CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BHHYHSUAOQUXJK-UHFFFAOYSA-L Zinc fluoride Inorganic materials F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- HNGXFQSHIPNFSC-UHFFFAOYSA-N iodomethane;methoxymethane Chemical compound IC.COC HNGXFQSHIPNFSC-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000012716 precipitator Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- 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
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/138—Compounds comprising a halogen and an alkaline earth metal, magnesium, beryllium, zinc, cadmium or mercury
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0105165A GB0105165D0 (en) | 2001-03-02 | 2001-03-02 | Preparation of hydrocarbons |
| GB0105165.5 | 2001-03-02 | ||
| GB0115740.3 | 2001-06-28 | ||
| GB0115740A GB0115740D0 (en) | 2001-06-28 | 2001-06-28 | Preparation of hydrocarbons |
| PCT/GB2002/000843 WO2002070440A1 (en) | 2001-03-02 | 2002-02-27 | Method and apparatus for the preparation of triptane and/or triptene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2439571A1 true CA2439571A1 (en) | 2002-09-12 |
Family
ID=26245774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002439571A Abandoned CA2439571A1 (en) | 2001-03-02 | 2002-02-27 | Method and apparatus for the preparation of triptane and/or triptene |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20040133055A1 (enExample) |
| EP (1) | EP1363866B1 (enExample) |
| JP (1) | JP2005501807A (enExample) |
| AT (1) | ATE392401T1 (enExample) |
| CA (1) | CA2439571A1 (enExample) |
| DE (1) | DE60226128T2 (enExample) |
| DK (1) | DK1363866T3 (enExample) |
| EG (1) | EG23438A (enExample) |
| ES (1) | ES2303853T3 (enExample) |
| NZ (1) | NZ527843A (enExample) |
| WO (1) | WO2002070440A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0320684D0 (en) * | 2003-09-03 | 2003-10-01 | Bp Chem Int Ltd | Process |
| EP1900714A1 (en) * | 2006-09-12 | 2008-03-19 | Bp Oil International Limited | Process for the production of hydrocarbons |
| WO2009064622A2 (en) * | 2007-11-13 | 2009-05-22 | California Institute Of Technology | Process for the production of a hydrocarbon |
| EP2060551A1 (en) | 2007-11-16 | 2009-05-20 | BP p.l.c. | Process for producing triptane |
| AU2008322792A1 (en) * | 2007-11-16 | 2009-05-22 | Bp P.L.C. | Process for producing triptane |
| EP2060550A1 (en) | 2007-11-16 | 2009-05-20 | BP p.l.c. | Process for producing triptane |
| US7825287B2 (en) * | 2008-03-28 | 2010-11-02 | The Regents Of The University Of California | Process for production of triptane and triptene |
| US20130102826A1 (en) * | 2011-05-24 | 2013-04-25 | James R. Lattner | Systems And Methods For Generating Alpha Olefin Oligomers |
| CN105399592B (zh) * | 2015-11-04 | 2017-05-10 | 鹤壁宝发能源科技股份有限公司 | 粗二甲醚联产混合烯烃、芳烃、液化气的系统及工艺 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2492984A (en) * | 1946-05-31 | 1950-01-03 | Houdry Process Corp | Organic reactions |
| US3363010A (en) * | 1961-08-02 | 1968-01-09 | Pullman Inc | Halogenation process |
| US3542886A (en) * | 1968-10-18 | 1970-11-24 | Sun Oil Co | Catalyst recycle |
| US3685962A (en) * | 1970-04-27 | 1972-08-22 | Shell Oil Co | Regeneration of metal halide catalyst |
| US3790469A (en) * | 1973-03-16 | 1974-02-05 | Shell Oil Co | Hydrocracking coal in molten zinc iodide |
| US3969427A (en) * | 1974-11-19 | 1976-07-13 | Mobil Oil Corporation | Conversion of alcohols and/or ethers to hydrocarbons |
| US4045461A (en) * | 1975-02-03 | 1977-08-30 | Shell Oil Company | High temperature methanation with molten salt-based catalyst systems |
| US3979332A (en) * | 1975-02-03 | 1976-09-07 | Shell Oil Company | High temperature methanation with molten salt-based catalyst systems |
| US4059647A (en) * | 1975-10-02 | 1977-11-22 | Shell Oil Company | Process for producing triptane by contacting methanol or dimethyl ether with zinc chloride |
| US4059646A (en) * | 1975-10-02 | 1977-11-22 | Shell Oil Company | Process for producing triptane by contacting methanol or dimethyl ether with zinc bromide |
| US4006177A (en) * | 1975-10-03 | 1977-02-01 | Shell Oil Company | Methanation catalyst recovery |
| US4126642A (en) * | 1977-11-14 | 1978-11-21 | Shell Oil Company | Conversion of butadiene (1,3) and methanol |
| US4126643A (en) * | 1977-11-14 | 1978-11-21 | Shell Oil Company | Butadiene (1,3) conversion |
| US4151214A (en) * | 1977-11-14 | 1979-04-24 | Shell Oil Company | Process for methylation of olefins |
| US4166189A (en) * | 1978-04-24 | 1979-08-28 | Shell Oil Company | Production of methyl esters by contacting methanol or dimethyl ether with carbon monoxide and zinc iodide |
| NL7902886A (nl) * | 1979-04-12 | 1980-10-14 | Shell Int Research | Werkwijze voor de bereiding van een koolwaterstof- mengsel. |
| GB8326556D0 (en) * | 1983-10-04 | 1983-11-02 | Ici Plc | Carbonate production |
-
2002
- 2002-02-27 DK DK02703706T patent/DK1363866T3/da active
- 2002-02-27 US US10/469,341 patent/US20040133055A1/en not_active Abandoned
- 2002-02-27 EP EP02703706A patent/EP1363866B1/en not_active Expired - Lifetime
- 2002-02-27 ES ES02703706T patent/ES2303853T3/es not_active Expired - Lifetime
- 2002-02-27 AT AT02703706T patent/ATE392401T1/de not_active IP Right Cessation
- 2002-02-27 NZ NZ527843A patent/NZ527843A/en unknown
- 2002-02-27 JP JP2002569765A patent/JP2005501807A/ja not_active Ceased
- 2002-02-27 WO PCT/GB2002/000843 patent/WO2002070440A1/en not_active Ceased
- 2002-02-27 DE DE60226128T patent/DE60226128T2/de not_active Expired - Fee Related
- 2002-02-27 CA CA002439571A patent/CA2439571A1/en not_active Abandoned
- 2002-03-02 EG EG20020226A patent/EG23438A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002070440A1 (en) | 2002-09-12 |
| US20040133055A1 (en) | 2004-07-08 |
| ATE392401T1 (de) | 2008-05-15 |
| EP1363866A1 (en) | 2003-11-26 |
| DE60226128T2 (de) | 2009-07-02 |
| NZ527843A (en) | 2005-08-26 |
| WO2002070440A8 (en) | 2002-11-14 |
| EG23438A (en) | 2005-08-24 |
| JP2005501807A (ja) | 2005-01-20 |
| DE60226128D1 (de) | 2008-05-29 |
| EP1363866B1 (en) | 2008-04-16 |
| ES2303853T3 (es) | 2008-09-01 |
| DK1363866T3 (da) | 2008-08-11 |
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| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |