DE19932060A1 - Verfahren zur Herstellung von C¶5¶-/C¶6¶-Olefinen - Google Patents
Verfahren zur Herstellung von C¶5¶-/C¶6¶-OlefinenInfo
- Publication number
- DE19932060A1 DE19932060A1 DE19932060A DE19932060A DE19932060A1 DE 19932060 A1 DE19932060 A1 DE 19932060A1 DE 19932060 A DE19932060 A DE 19932060A DE 19932060 A DE19932060 A DE 19932060A DE 19932060 A1 DE19932060 A1 DE 19932060A1
- Authority
- DE
- Germany
- Prior art keywords
- isobutene
- butene
- olefins
- metathesis
- catalyst
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 40
- 230000008569 process Effects 0.000 title claims abstract description 24
- 150000001336 alkenes Chemical class 0.000 title description 11
- 238000004519 manufacturing process Methods 0.000 title description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 127
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract description 76
- 239000003054 catalyst Substances 0.000 claims abstract description 72
- 238000005649 metathesis reaction Methods 0.000 claims abstract description 53
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims abstract description 51
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims abstract description 35
- 235000013844 butane Nutrition 0.000 claims abstract description 30
- 238000004821 distillation Methods 0.000 claims abstract description 25
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 229910052751 metal Inorganic materials 0.000 claims abstract description 16
- 239000002184 metal Substances 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims abstract description 12
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000000737 periodic effect Effects 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 claims abstract description 5
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims abstract description 5
- 210000003918 fraction a Anatomy 0.000 claims abstract description 4
- 210000002196 fr. b Anatomy 0.000 claims abstract description 3
- 210000000540 fraction c Anatomy 0.000 claims abstract description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 83
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 238000005984 hydrogenation reaction Methods 0.000 claims description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 23
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 17
- 238000000926 separation method Methods 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000006266 etherification reaction Methods 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 238000004140 cleaning Methods 0.000 claims description 12
- 238000000605 extraction Methods 0.000 claims description 12
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 239000007791 liquid phase Substances 0.000 claims description 11
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 10
- 239000012535 impurity Substances 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- 238000005336 cracking Methods 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001993 dienes Chemical class 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003377 acid catalyst Substances 0.000 claims description 5
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 claims description 5
- 229910003449 rhenium oxide Inorganic materials 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- 230000007306 turnover Effects 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 239000001273 butane Substances 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 3
- 238000006384 oligomerization reaction Methods 0.000 claims description 3
- 150000003623 transition metal compounds Chemical class 0.000 claims description 3
- 239000000499 gel Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 28
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 22
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 20
- -1 C 4 hydrocarbons Chemical class 0.000 description 14
- 239000007789 gas Substances 0.000 description 11
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 8
- 239000002808 molecular sieve Substances 0.000 description 8
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 6
- 150000001345 alkine derivatives Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000004064 recycling Methods 0.000 description 5
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 5
- 229910052721 tungsten Inorganic materials 0.000 description 5
- 239000010937 tungsten Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 4
- 238000005686 cross metathesis reaction Methods 0.000 description 4
- 238000000895 extractive distillation Methods 0.000 description 4
- 239000002815 homogeneous catalyst Substances 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- 229910052750 molybdenum Inorganic materials 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002638 heterogeneous catalyst Substances 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 239000002574 poison Substances 0.000 description 3
- 231100000614 poison Toxicity 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000000066 reactive distillation Methods 0.000 description 3
- 229910052702 rhenium Inorganic materials 0.000 description 3
- 238000005872 self-metathesis reaction Methods 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 2
- UPOMCDPCTBJJDA-UHFFFAOYSA-N 2-methyl-1-[(2-methylpropan-2-yl)oxy]propane Chemical compound CC(C)COC(C)(C)C UPOMCDPCTBJJDA-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000000475 acetylene derivatives Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000005865 alkene metathesis reaction Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 229910052745 lead Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 description 1
- 108700028369 Alleles Proteins 0.000 description 1
- 241000819038 Chichester Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 241001481828 Glyptocephalus cynoglossus Species 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- LFKIGTZUWPXSIH-UHFFFAOYSA-N but-1-ene;2-methylprop-1-ene Chemical compound CCC=C.CC(C)=C LFKIGTZUWPXSIH-UHFFFAOYSA-N 0.000 description 1
- HHEMIMSLFVBJMH-UHFFFAOYSA-N but-1-yne Chemical compound C#CCC.C(C)C#C HHEMIMSLFVBJMH-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000012041 precatalyst Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003657 tungsten Chemical class 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14875—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds
- C07C7/14891—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/10—Alkenes with five carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/107—Alkenes with six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- C07C2521/08—Silica
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/32—Manganese, technetium or rhenium
- C07C2523/36—Rhenium
-
- 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
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19932060A DE19932060A1 (de) | 1999-07-12 | 1999-07-12 | Verfahren zur Herstellung von C¶5¶-/C¶6¶-Olefinen |
| US09/610,942 US6538168B1 (en) | 1999-07-12 | 2000-07-06 | Preparation of C5-/C6-olefins |
| ES00114104T ES2208187T3 (es) | 1999-07-12 | 2000-07-10 | Procedimiento para la produccion de olefinas con 5/6 atomos de carbono. |
| JP2000207761A JP2001072612A (ja) | 1999-07-12 | 2000-07-10 | Ｃ５−／ｃ６−オレフィンの製造方法 |
| DE50003881T DE50003881D1 (de) | 1999-07-12 | 2000-07-10 | Verfahren zur Herstellung von C5-/C6-Olefinen |
| EP00114104A EP1069101B1 (de) | 1999-07-12 | 2000-07-10 | Verfahren zur Herstellung von C5-/C6-Olefinen |
| MYPI20003176 MY127059A (en) | 1999-07-12 | 2000-07-11 | Process for the preparation of c5-/c6-olefins. |
| CA002313850A CA2313850C (en) | 1999-07-12 | 2000-07-11 | Preparation of c5-/c6 olefins |
| TW089113771A TW527336B (en) | 1999-07-12 | 2000-07-11 | Process for preparing C5-/C6-olefins |
| CNB001262742A CN1213972C (zh) | 1999-07-12 | 2000-07-12 | C5－/c6－烯烃的制备 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19932060A DE19932060A1 (de) | 1999-07-12 | 1999-07-12 | Verfahren zur Herstellung von C¶5¶-/C¶6¶-Olefinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19932060A1 true DE19932060A1 (de) | 2001-01-18 |
Family
ID=7914225
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19932060A Withdrawn DE19932060A1 (de) | 1999-07-12 | 1999-07-12 | Verfahren zur Herstellung von C¶5¶-/C¶6¶-Olefinen |
| DE50003881T Expired - Fee Related DE50003881D1 (de) | 1999-07-12 | 2000-07-10 | Verfahren zur Herstellung von C5-/C6-Olefinen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50003881T Expired - Fee Related DE50003881D1 (de) | 1999-07-12 | 2000-07-10 | Verfahren zur Herstellung von C5-/C6-Olefinen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6538168B1 (enExample) |
| EP (1) | EP1069101B1 (enExample) |
| JP (1) | JP2001072612A (enExample) |
| CN (1) | CN1213972C (enExample) |
| CA (1) | CA2313850C (enExample) |
| DE (2) | DE19932060A1 (enExample) |
| ES (1) | ES2208187T3 (enExample) |
| MY (1) | MY127059A (enExample) |
| TW (1) | TW527336B (enExample) |
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| EP1134271A3 (de) * | 2000-03-17 | 2003-03-12 | Basf Aktiengesellschaft | Verfahren zur flexiblen Herstellung von Propen und Hexen |
| US7652183B2 (en) | 2003-04-15 | 2010-01-26 | Basf Aktiengesellschaft | Method for producing alkyl aromatic compounds |
| DE102009026581A1 (de) | 2009-05-29 | 2010-12-02 | Evonik Oxeno Gmbh | Katalysator für die Herstellung von 3-Methylbut-1-en aus 3-Methylbutan-1-ol |
| DE102009026585A1 (de) | 2009-05-29 | 2010-12-02 | Evonik Oxeno Gmbh | Herstellung von 3-Methylbut-1-en durch Dehydratisierung von 3-Methylbutan-1-ol |
| DE102012215757A1 (de) * | 2012-09-05 | 2014-03-06 | Evonik Industries Ag | Verfahren zur Herstellung von linearen Butenen aus Methanol |
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| DE10143160A1 (de) * | 2001-09-04 | 2003-03-20 | Basf Ag | Verfahren zur Herstellung von Propen durch Metathese von C4-bis C9-Olefinen |
| DE10206845A1 (de) * | 2002-02-19 | 2003-08-28 | Basf Ag | Modifiziertes Verfahren zur Herstellung von Tensidalkoholen und Tensidalkoholethern, die hergestellten Produkte und ihre Verwendung |
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| RU2254318C1 (ru) * | 2003-12-30 | 2005-06-20 | Мартиросян Артур Георгиевич | Способ очистки альфа-олефинов, способ очистки гексена-i и установка для его осуществления |
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| US20060129013A1 (en) * | 2004-12-09 | 2006-06-15 | Abazajian Armen N | Specific functionalization and scission of linear hydrocarbon chains |
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| US11339332B2 (en) | 2020-01-29 | 2022-05-24 | Saudi Arabian Oil Company | Systems and processes integrating fluidized catalytic cracking with metathesis for producing olefins |
| US11572516B2 (en) | 2020-03-26 | 2023-02-07 | Saudi Arabian Oil Company | Systems and processes integrating steam cracking with dual catalyst metathesis for producing olefins |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3590096A (en) * | 1968-04-18 | 1971-06-29 | Phillips Petroleum Co | Conversion of isobutene to isoamylene |
| US3595920A (en) | 1969-05-05 | 1971-07-27 | Gulf Research Development Co | Process for converting an olefin to a product containing higher and lower olefins |
| BE755254A (fr) | 1969-08-25 | 1971-02-01 | Gulf Research & Dev Cy | Procede pour transformer une olefine metathese |
| US5057638A (en) | 1990-06-22 | 1991-10-15 | Chevron Research And Technology Company | Process for making 1-hexene from 1-butene |
| JPH05103995A (ja) * | 1991-10-17 | 1993-04-27 | Maruzen Petrochem Co Ltd | オレフインの不均化触媒およびその触媒を用いたオレフインの不均化方法 |
| DE19746040A1 (de) | 1997-10-17 | 1999-04-22 | Basf Ag | Verfahren zur Herstellung von Propen |
| DE19813720A1 (de) | 1998-03-27 | 1999-09-30 | Basf Ag | Verfahren zur Herstellung von Olefinen |
-
1999
- 1999-07-12 DE DE19932060A patent/DE19932060A1/de not_active Withdrawn
-
2000
- 2000-07-06 US US09/610,942 patent/US6538168B1/en not_active Expired - Fee Related
- 2000-07-10 ES ES00114104T patent/ES2208187T3/es not_active Expired - Lifetime
- 2000-07-10 DE DE50003881T patent/DE50003881D1/de not_active Expired - Fee Related
- 2000-07-10 JP JP2000207761A patent/JP2001072612A/ja not_active Withdrawn
- 2000-07-10 EP EP00114104A patent/EP1069101B1/de not_active Expired - Lifetime
- 2000-07-11 CA CA002313850A patent/CA2313850C/en not_active Expired - Fee Related
- 2000-07-11 MY MYPI20003176 patent/MY127059A/en unknown
- 2000-07-11 TW TW089113771A patent/TW527336B/zh not_active IP Right Cessation
- 2000-07-12 CN CNB001262742A patent/CN1213972C/zh not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1134271A3 (de) * | 2000-03-17 | 2003-03-12 | Basf Aktiengesellschaft | Verfahren zur flexiblen Herstellung von Propen und Hexen |
| US6580009B2 (en) | 2000-03-17 | 2003-06-17 | Basf Aktiengesellschaft | Flexible preparation of propene and hexene |
| US7652183B2 (en) | 2003-04-15 | 2010-01-26 | Basf Aktiengesellschaft | Method for producing alkyl aromatic compounds |
| DE102009026581A1 (de) | 2009-05-29 | 2010-12-02 | Evonik Oxeno Gmbh | Katalysator für die Herstellung von 3-Methylbut-1-en aus 3-Methylbutan-1-ol |
| DE102009026585A1 (de) | 2009-05-29 | 2010-12-02 | Evonik Oxeno Gmbh | Herstellung von 3-Methylbut-1-en durch Dehydratisierung von 3-Methylbutan-1-ol |
| DE102012215757A1 (de) * | 2012-09-05 | 2014-03-06 | Evonik Industries Ag | Verfahren zur Herstellung von linearen Butenen aus Methanol |
Also Published As
| Publication number | Publication date |
|---|---|
| TW527336B (en) | 2003-04-11 |
| JP2001072612A (ja) | 2001-03-21 |
| EP1069101B1 (de) | 2003-10-01 |
| EP1069101A1 (de) | 2001-01-17 |
| DE50003881D1 (de) | 2003-11-06 |
| CN1213972C (zh) | 2005-08-10 |
| ES2208187T3 (es) | 2004-06-16 |
| MY127059A (en) | 2006-11-30 |
| US6538168B1 (en) | 2003-03-25 |
| CA2313850A1 (en) | 2001-01-12 |
| CN1285338A (zh) | 2001-02-28 |
| CA2313850C (en) | 2008-06-03 |
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