DE10013253A1 - Verfahren zur flexiblen Herstellung von Propen und Hexen - Google Patents
Verfahren zur flexiblen Herstellung von Propen und HexenInfo
- Publication number
- DE10013253A1 DE10013253A1 DE10013253A DE10013253A DE10013253A1 DE 10013253 A1 DE10013253 A1 DE 10013253A1 DE 10013253 A DE10013253 A DE 10013253A DE 10013253 A DE10013253 A DE 10013253A DE 10013253 A1 DE10013253 A1 DE 10013253A1
- Authority
- DE
- Germany
- Prior art keywords
- fraction
- isobutene
- butenes
- butene
- ethene
- 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- Withdrawn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
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title claims abstract description 94
- 239000003054 catalyst Substances 0.000 title claims abstract description 71
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 238000005649 metathesis reaction Methods 0.000 title claims abstract description 57
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 title claims abstract description 22
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 16
- 239000002184 metal Substances 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 title claims description 43
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract description 85
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims abstract description 63
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims abstract description 32
- 235000013844 butane Nutrition 0.000 claims abstract description 27
- 210000002196 fr. b Anatomy 0.000 claims abstract description 8
- 210000003918 fraction a Anatomy 0.000 claims abstract description 7
- 210000000540 fraction c Anatomy 0.000 claims abstract description 5
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims abstract description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 113
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 84
- 238000000034 method Methods 0.000 claims description 48
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims description 34
- 238000004821 distillation Methods 0.000 claims description 31
- 238000005984 hydrogenation reaction Methods 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 28
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 25
- 239000000047 product Substances 0.000 claims description 25
- 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
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000000926 separation method Methods 0.000 claims description 19
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- 229930195733 hydrocarbon Natural products 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- 238000004140 cleaning Methods 0.000 claims description 13
- 238000006266 etherification reaction Methods 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 12
- 238000000605 extraction Methods 0.000 claims description 12
- 239000007791 liquid phase Substances 0.000 claims description 12
- 239000012535 impurity 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
- 230000002378 acidificating effect Effects 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- 150000001993 dienes Chemical class 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 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
- 230000000737 periodic effect Effects 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
- 238000006317 isomerization reaction Methods 0.000 claims description 5
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 claims description 5
- 238000006116 polymerization reaction Methods 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
- 239000000969 carrier Substances 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
- 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
- 238000005192 partition Methods 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- 238000004064 recycling Methods 0.000 abstract description 3
- 239000005977 Ethylene Substances 0.000 description 18
- -1 C 4 hydrocarbons Chemical class 0.000 description 15
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- 150000002430 hydrocarbons Chemical class 0.000 description 11
- 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 9
- 150000001336 alkenes Chemical class 0.000 description 9
- 239000002808 molecular sieve Substances 0.000 description 9
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 238000005336 cracking Methods 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 241001481828 Glyptocephalus cynoglossus Species 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 150000001345 alkine derivatives Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229910052721 tungsten Inorganic materials 0.000 description 5
- 150000001298 alcohols Chemical class 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
- 238000010926 purge Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 4
- 239000010937 tungsten Substances 0.000 description 4
- 229920002367 Polyisobutene Polymers 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- 229910052750 molybdenum Inorganic materials 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
- 230000001681 protective effect Effects 0.000 description 3
- 238000005872 self-metathesis reaction Methods 0.000 description 3
- 229910052709 silver Inorganic materials 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
- QMMOXUPEWRXHJS-HWKANZROSA-N (e)-pent-2-ene Chemical compound CC\C=C\C QMMOXUPEWRXHJS-HWKANZROSA-N 0.000 description 2
- QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-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
- 239000002841 Lewis acid Substances 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
- 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
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000005865 alkene metathesis reaction Methods 0.000 description 2
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 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
- ZQDPJFUHLCOCRG-WAYWQWQTSA-N cis-3-hexene Chemical compound CC\C=C/CC ZQDPJFUHLCOCRG-WAYWQWQTSA-N 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 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
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 238000005470 impregnation 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
- 150000007517 lewis acids Chemical class 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
- 238000005457 optimization Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000066 reactive distillation Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- ZQDPJFUHLCOCRG-AATRIKPKSA-N trans-3-hexene Chemical compound CC\C=C\CC ZQDPJFUHLCOCRG-AATRIKPKSA-N 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
- 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 1
- HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 description 1
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 1
- 108700028369 Alleles Proteins 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
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 229910021536 Zeolite Inorganic materials 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
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 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
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 230000008859 change Effects 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
- 239000000571 coke Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 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
- 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
- 150000002170 ethers Chemical class 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
- 238000011049 filling 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
- 238000002955 isolation Methods 0.000 description 1
- 229910052746 lanthanum Inorganic materials 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
- 239000011733 molybdenum Substances 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
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000004014 plasticizer Substances 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
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 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
- 238000001228 spectrum 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
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003657 tungsten Chemical class 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
Classifications
-
- 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
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
- C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
- C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- 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
- C07C7/14875—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
- 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
- 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
- C07C7/167—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation for removal of compounds containing a triple carbon-to-carbon bond
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G70/00—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00
-
- 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
-
- 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
- C07C2521/12—Silica and alumina
-
- 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
-
- 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
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/42—Platinum
-
- 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
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
-
- 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
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/755—Nickel
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/40—Ethylene production
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10013253A DE10013253A1 (de) | 2000-03-17 | 2000-03-17 | Verfahren zur flexiblen Herstellung von Propen und Hexen |
| US09/803,147 US6580009B2 (en) | 2000-03-17 | 2001-03-12 | Flexible preparation of propene and hexene |
| EP01105437A EP1134271B1 (de) | 2000-03-17 | 2001-03-13 | Verfahren zur flexiblen Herstellung von Propen und Hexen |
| DE50115484T DE50115484D1 (de) | 2000-03-17 | 2001-03-13 | Verfahren zur flexiblen Herstellung von Propen und Hexen |
| ES01105437T ES2345317T3 (es) | 2000-03-17 | 2001-03-13 | Procedimiento para la obtencion flexible de propeno y de hexeno. |
| JP2001072595A JP4749577B2 (ja) | 2000-03-17 | 2001-03-14 | プロペンおよびヘキセンの弾力的な製造 |
| CNB011173947A CN1204096C (zh) | 2000-03-17 | 2001-03-17 | 丙烯和己烯的可变制备方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10013253A DE10013253A1 (de) | 2000-03-17 | 2000-03-17 | Verfahren zur flexiblen Herstellung von Propen und Hexen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10013253A1 true DE10013253A1 (de) | 2001-09-20 |
Family
ID=7635266
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10013253A Withdrawn DE10013253A1 (de) | 2000-03-17 | 2000-03-17 | Verfahren zur flexiblen Herstellung von Propen und Hexen |
| DE50115484T Expired - Lifetime DE50115484D1 (de) | 2000-03-17 | 2001-03-13 | Verfahren zur flexiblen Herstellung von Propen und Hexen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50115484T Expired - Lifetime DE50115484D1 (de) | 2000-03-17 | 2001-03-13 | Verfahren zur flexiblen Herstellung von Propen und Hexen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6580009B2 (enExample) |
| EP (1) | EP1134271B1 (enExample) |
| JP (1) | JP4749577B2 (enExample) |
| CN (1) | CN1204096C (enExample) |
| DE (2) | DE10013253A1 (enExample) |
| ES (1) | ES2345317T3 (enExample) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7923588B2 (en) | 2004-10-13 | 2011-04-12 | Basf Se | Process for preparing a C4-olefin mixture by selective hydrogenation and metathesis process for using this stream |
| US10052618B2 (en) | 2015-07-02 | 2018-08-21 | Saudi Arabian Oil Company | Dual catalyst system for propylene production |
| US10065906B2 (en) | 2015-07-02 | 2018-09-04 | Saudi Arabian Oil Company | Systems and methods for producing propylene |
| US10214466B2 (en) | 2015-07-02 | 2019-02-26 | Saudi Arabian Oil Company | Systems and methods for producing propylene |
| US10329225B2 (en) | 2017-01-20 | 2019-06-25 | Saudi Arabian Oil Company | Dual catalyst processes and systems for propylene production |
| US10550048B2 (en) | 2017-01-20 | 2020-02-04 | Saudi Arabian Oil Company | Multiple-stage catalyst system for self-metathesis with controlled isomerization and cracking |
| US10934231B2 (en) | 2017-01-20 | 2021-03-02 | Saudi Arabian Oil Company | Multiple-stage catalyst systems and processes for propene production |
| US10961171B2 (en) | 2018-10-10 | 2021-03-30 | Saudi Arabian Oil Company | Catalysts systems that include metal co-catalysts for the production of propylene |
| US11242299B2 (en) | 2018-10-10 | 2022-02-08 | Saudi Arabian Oil Company | Catalyst systems that include metal oxide co-catalysts for the production of propylene |
| US11311869B2 (en) | 2019-12-03 | 2022-04-26 | Saudi Arabian Oil Company | Methods of producing isomerization catalysts |
| US11339332B2 (en) | 2020-01-29 | 2022-05-24 | Saudi Arabian Oil Company | Systems and processes integrating fluidized catalytic cracking with metathesis for producing olefins |
| US11517892B2 (en) | 2019-12-03 | 2022-12-06 | Saudi Arabian Oil Company | Methods of producing isomerization catalysts |
| 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 |
| US11679378B2 (en) | 2021-02-25 | 2023-06-20 | Saudi Arabian Oil Company | Methods of producing isomerization catalysts |
| US11845705B2 (en) | 2021-08-17 | 2023-12-19 | Saudi Arabian Oil Company | Processes integrating hydrocarbon cracking with metathesis for producing propene |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10039995A1 (de) * | 2000-08-11 | 2002-02-21 | Basf Ag | Verfahren zur Herstellung von Alkylarylsulfonaten |
| EP1942090B1 (en) * | 2001-01-25 | 2013-10-23 | Lummus Technology Inc. | Process for the production of hexene-1 and ethylene |
| US20050124839A1 (en) * | 2001-06-13 | 2005-06-09 | Gartside Robert J. | Catalyst and process for the metathesis of ethylene and butene to produce propylene |
| US6777582B2 (en) * | 2002-03-07 | 2004-08-17 | Abb Lummus Global Inc. | Process for producing propylene and hexene from C4 olefin streams |
| US7214841B2 (en) * | 2003-07-15 | 2007-05-08 | Abb Lummus Global Inc. | Processing C4 olefin streams for the maximum production of propylene |
| ATE401292T1 (de) * | 2003-10-21 | 2008-08-15 | Basf Se | Verfahren zur kontinuierlichen herstellung von aldehyden |
| DE102004009805A1 (de) * | 2004-02-28 | 2005-09-15 | Basf Ag | Trägerkatalysator definierter Porenverteilung im Bereich der Mesoporen |
| FR2872510B1 (fr) * | 2004-07-02 | 2006-09-08 | Cpe Lyon Fcr | Procede de transformation d'ethylene en propylene |
| FR2872509B1 (fr) * | 2004-07-02 | 2006-09-22 | Cpe Lyon Fcr | Procede de metathese de composes comportant une double liaison olefinique, notamment d'olefines |
| JP4736392B2 (ja) * | 2004-10-14 | 2011-07-27 | 三菱化学株式会社 | アルデヒドの製造方法 |
| US20060129013A1 (en) * | 2004-12-09 | 2006-06-15 | Abazajian Armen N | Specific functionalization and scission of linear hydrocarbon chains |
| DE102005009596A1 (de) * | 2005-02-28 | 2006-08-31 | Basf Ag | Verfahren zur Metathese umfassend die Reinigung der Ausgangsstoffe |
| DE102005009665A1 (de) * | 2005-02-28 | 2006-08-31 | Basf Ag | Verfahren zur Herstellung von Propen aus 2-Buten- und Isobuten-reichen Feedströmen |
| CN101172926B (zh) * | 2006-11-02 | 2010-12-22 | 中国石油化工股份有限公司 | 丙烯的增产方法 |
| US20080154077A1 (en) * | 2006-12-21 | 2008-06-26 | Bozzano Andrea G | Oxygenate conversion to olefins with metathesis |
| US7528290B2 (en) * | 2006-12-28 | 2009-05-05 | Uop Llc | Apparatuses and methods for separating butene-1 from a mixed C4 feed |
| JP5255325B2 (ja) * | 2008-05-21 | 2013-08-07 | 旭化成ケミカルズ株式会社 | 粗プロパン及び／又は粗プロピレンの精製方法並びに精製装置 |
| BRPI0918014B1 (pt) | 2008-08-12 | 2018-05-08 | Lummus Technology Inc | "processo para a produção de propileno" |
| WO2010028267A2 (en) * | 2008-09-04 | 2010-03-11 | Lummus Technology Inc. | Olefin isomerization and metathesis catalyst |
| US7982086B2 (en) * | 2009-02-03 | 2011-07-19 | Catalytic Distillation Technologies | Deisobutenizer |
| US8258357B2 (en) * | 2009-03-25 | 2012-09-04 | Lummus Technology Inc. | Production of propylene from butane |
| US8586813B2 (en) * | 2009-07-21 | 2013-11-19 | Lummus Technology Inc. | Catalyst for metathesis of ethylene and 2-butene and/or double bond isomerization |
| US8440871B2 (en) * | 2010-03-30 | 2013-05-14 | Uop Llc | Tetramer production apparatus and process relating thereto |
| US8722950B2 (en) | 2010-04-26 | 2014-05-13 | Saudi Basic Industries Corporation | Process for producing propylene and aromatics from butenes by metathesis and aromatization |
| DE102011001587B4 (de) * | 2010-08-05 | 2016-12-29 | Flagsol Gmbh | Verfahren zum Aufbereiten eines Wärmeträgermediums eines solarthermischen Kraftwerks |
| US8674155B2 (en) * | 2010-12-22 | 2014-03-18 | Kellogg Brown & Root, Llc | Systems and methods for processing hydrocarbons |
| WO2013034689A1 (en) * | 2011-09-07 | 2013-03-14 | Shell Internationale Research Maatschappij B.V. | Process for preparing ethylene and/or propylene and an iso-olefin-depleted olefinic product |
| GB201116801D0 (en) | 2011-09-29 | 2011-11-09 | Johnson Matthey Plc | Purification process |
| SG11201501890YA (en) | 2012-09-14 | 2015-04-29 | Lummus Technology Inc | Propylene via metathesis with low or no ethylene |
| CN103772095B (zh) * | 2012-10-25 | 2015-09-09 | 中国石油化工股份有限公司 | 丁烯歧化制己烯的方法 |
| CA2907499C (en) | 2013-03-28 | 2018-01-23 | The Procter & Gamble Company | Cleaning compositions containing a polyetheramine, a soil release polymer, and a carboxymethylcellulose |
| CN104437525B (zh) * | 2013-09-24 | 2017-01-04 | 中国石油化工股份有限公司 | 歧化催化剂 |
| US9701913B2 (en) * | 2013-12-17 | 2017-07-11 | Uop Llc | Fluid catalytic cracking process including adsorption of hydrogen and a catalyst for the process |
| WO2015148361A1 (en) | 2014-03-27 | 2015-10-01 | The Procter & Gamble Company | Cleaning compositions containing a polyetheramine |
| JP6275864B2 (ja) | 2014-03-27 | 2018-02-07 | ザ プロクター アンド ギャンブル カンパニー | ポリエーテルアミンを含有する洗浄組成物 |
| WO2015187757A1 (en) | 2014-06-06 | 2015-12-10 | The Procter & Gamble Company | Detergent composition comprising polyalkyleneimine polymers |
| US9809782B2 (en) | 2014-08-27 | 2017-11-07 | The Procter & Gamble Company | Detergent composition comprising a cationic polymer and anionic/nonionic surfactant mixture |
| WO2016032991A1 (en) | 2014-08-27 | 2016-03-03 | The Procter & Gamble Company | Detergent composition comprising a cationic polymer |
| US9617501B2 (en) | 2014-08-27 | 2017-04-11 | The Procter & Gamble Company | Method of treating a fabric by washing with a detergent comprising an acrylamide/DADMAC cationic polymer |
| EP3186345A1 (en) | 2014-08-27 | 2017-07-05 | The Procter and Gamble Company | Detergent composition comprising a cationic polymer |
| US9850452B2 (en) | 2014-09-25 | 2017-12-26 | The Procter & Gamble Company | Fabric care compositions containing a polyetheramine |
| US10131594B2 (en) * | 2014-10-28 | 2018-11-20 | SMG Co., Ltd | Metathesis catalyst on mixed metal oxide-zeolite support and process for use thereof |
| CN112135809A (zh) * | 2018-05-18 | 2020-12-25 | 沙特基础工业全球技术有限公司 | 利用水合单元生产燃料添加剂的方法 |
| US12264123B2 (en) | 2019-03-08 | 2025-04-01 | Sabic Global Technologies B.V. | Method of producing a fuel additive |
| EP4139267A1 (en) | 2020-04-22 | 2023-03-01 | Lyondell Chemical Technology, L.P. | On-purpose propylene production from butenes |
| US11926587B2 (en) | 2020-09-15 | 2024-03-12 | Lyondell Chemical Technology, L.P. | Process for converting raffinate butenes to propylene |
| CA3228918A1 (en) | 2021-08-10 | 2023-02-16 | Nippon Shokubai Co., Ltd. | Polyalkylene-oxide-containing compound |
| CN118019722A (zh) * | 2021-08-20 | 2024-05-10 | 埃克森美孚化学专利公司 | C4/c5复分解成丙烯和1-己烯 |
| WO2025083637A1 (en) * | 2023-10-18 | 2025-04-24 | Sabic Global Technologies B.V. | Systems and methods for butene metathesis to produce propene and hex-1-ene |
| WO2025114973A1 (en) * | 2023-11-30 | 2025-06-05 | Sabic Global Technologies B.V. | Systems and methods for metathesis of mixed butene and butane feedstocks and recovery and recycle of reactive compounds |
| WO2025141045A1 (en) * | 2023-12-27 | 2025-07-03 | Sabic Global Technologies B.V. | Systems and methods for the production of propene with ethene being substantially absent as a co-feed |
| WO2025141047A1 (en) * | 2023-12-28 | 2025-07-03 | Sabic Global Technologies B.V. | Systems and methods for the production of propene using metathesis reactions |
| WO2025146438A1 (en) * | 2024-01-02 | 2025-07-10 | Sabic Global Technologies B.V. | Systems and methods of producing olefins products using alternate upstream and downstream separation processes at low-temperature metathesis conditions |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3775059D1 (de) * | 1983-03-10 | 1992-01-16 | Dow Chemical Co | Verfahren zur disproportionierung von alkenen. |
| US5057638A (en) | 1990-06-22 | 1991-10-15 | Chevron Research And Technology Company | Process for making 1-hexene from 1-butene |
| FR2733978B1 (fr) | 1995-05-11 | 1997-06-13 | Inst Francais Du Petrole | Procede et installation pour la conversion de coupes c4 et c5 olefiniques en ether et en propylene |
| DE59700957D1 (de) * | 1996-09-27 | 2000-02-10 | Basf Ag | Verfahren zur Herstellung von Propen |
| DE19746040A1 (de) * | 1997-10-17 | 1999-04-22 | Basf Ag | Verfahren zur Herstellung von Propen |
| DE19805716A1 (de) * | 1998-02-12 | 1999-08-19 | Basf Ag | Verfahren zur Herstellung von Propen und gegebenenfalls 1-Buten |
| DE19813720A1 (de) | 1998-03-27 | 1999-09-30 | Basf Ag | Verfahren zur Herstellung von Olefinen |
| DE19932060A1 (de) * | 1999-07-12 | 2001-01-18 | Basf Ag | Verfahren zur Herstellung von C¶5¶-/C¶6¶-Olefinen |
-
2000
- 2000-03-17 DE DE10013253A patent/DE10013253A1/de not_active Withdrawn
-
2001
- 2001-03-12 US US09/803,147 patent/US6580009B2/en not_active Expired - Lifetime
- 2001-03-13 EP EP01105437A patent/EP1134271B1/de not_active Expired - Lifetime
- 2001-03-13 DE DE50115484T patent/DE50115484D1/de not_active Expired - Lifetime
- 2001-03-13 ES ES01105437T patent/ES2345317T3/es not_active Expired - Lifetime
- 2001-03-14 JP JP2001072595A patent/JP4749577B2/ja not_active Expired - Fee Related
- 2001-03-17 CN CNB011173947A patent/CN1204096C/zh not_active Expired - Fee Related
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8362308B2 (en) | 2004-10-13 | 2013-01-29 | Basf Se | Process for preparing a C4-olefin mixture by selective hydrogenation and metathesis process for using this stream |
| US7923588B2 (en) | 2004-10-13 | 2011-04-12 | Basf Se | Process for preparing a C4-olefin mixture by selective hydrogenation and metathesis process for using this stream |
| US10583423B2 (en) | 2015-07-02 | 2020-03-10 | Saudi Arabian Oil Company | Dual catalyst system for propylene production |
| US10052618B2 (en) | 2015-07-02 | 2018-08-21 | Saudi Arabian Oil Company | Dual catalyst system for propylene production |
| US10065906B2 (en) | 2015-07-02 | 2018-09-04 | Saudi Arabian Oil Company | Systems and methods for producing propylene |
| US10214466B2 (en) | 2015-07-02 | 2019-02-26 | Saudi Arabian Oil Company | Systems and methods for producing propylene |
| US10532347B2 (en) | 2015-07-02 | 2020-01-14 | Saudi Arabian Oil Company | Dual catalyst system for propylene production |
| US10934231B2 (en) | 2017-01-20 | 2021-03-02 | Saudi Arabian Oil Company | Multiple-stage catalyst systems and processes for propene production |
| US11242297B2 (en) | 2017-01-20 | 2022-02-08 | Saudi Arabian Oil Company | Multiple-stage catalyst system for self-metathesis with controlled isomerization and cracking |
| US10919822B2 (en) | 2017-01-20 | 2021-02-16 | Saudi Arabian Oil Company | Dual catalyst processes and systems for propylene production |
| US10329225B2 (en) | 2017-01-20 | 2019-06-25 | Saudi Arabian Oil Company | Dual catalyst processes and systems for propylene production |
| US10550048B2 (en) | 2017-01-20 | 2020-02-04 | Saudi Arabian Oil Company | Multiple-stage catalyst system for self-metathesis with controlled isomerization and cracking |
| US11242300B2 (en) | 2018-10-10 | 2022-02-08 | Saudi Arabian Oil Company | Catalyst systems that include metal co-catalysts for the production of propylene |
| US11242299B2 (en) | 2018-10-10 | 2022-02-08 | Saudi Arabian Oil Company | Catalyst systems that include metal oxide co-catalysts for the production of propylene |
| US10961171B2 (en) | 2018-10-10 | 2021-03-30 | Saudi Arabian Oil Company | Catalysts systems that include metal co-catalysts for the production of propylene |
| US11311869B2 (en) | 2019-12-03 | 2022-04-26 | Saudi Arabian Oil Company | Methods of producing isomerization catalysts |
| US11517892B2 (en) | 2019-12-03 | 2022-12-06 | Saudi Arabian Oil Company | Methods of producing isomerization catalysts |
| 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 |
| US11939540B2 (en) | 2020-03-26 | 2024-03-26 | Saudi Arabian Oil Company | Systems and processes integrating steam cracking with dual catalyst metathesis for producing olefins |
| US11679378B2 (en) | 2021-02-25 | 2023-06-20 | Saudi Arabian Oil Company | Methods of producing isomerization catalysts |
| US11845705B2 (en) | 2021-08-17 | 2023-12-19 | Saudi Arabian Oil Company | Processes integrating hydrocarbon cracking with metathesis for producing propene |
Also Published As
| Publication number | Publication date |
|---|---|
| DE50115484D1 (de) | 2010-07-01 |
| CN1339426A (zh) | 2002-03-13 |
| EP1134271B1 (de) | 2010-05-19 |
| US6580009B2 (en) | 2003-06-17 |
| EP1134271A2 (de) | 2001-09-19 |
| JP2001302562A (ja) | 2001-10-31 |
| EP1134271A3 (de) | 2003-03-12 |
| US20020002317A1 (en) | 2002-01-03 |
| JP4749577B2 (ja) | 2011-08-17 |
| ES2345317T3 (es) | 2010-09-21 |
| CN1204096C (zh) | 2005-06-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1134271B1 (de) | Verfahren zur flexiblen Herstellung von Propen und Hexen | |
| EP1069101B1 (de) | Verfahren zur Herstellung von C5-/C6-Olefinen | |
| EP0945415B1 (de) | Verfahren zur Herstellung von Olefinen | |
| EP0915072B1 (de) | Verfahren zur Herstellung von Propen | |
| EP3218334B1 (de) | Verfahren zur herstellung von 1,3-butadien durch dehydrierung von n-butenen unter bereitstellung eines butane und 2-butene enthaltenden stoffstromes | |
| DE102004049940A1 (de) | Verfahren zur Herstellung eines C4-Olefin-Gemisches durch Selektivhydrierung und Metatheseverfahren zur Verwendung dieses Stroms | |
| EP3782970B1 (de) | Verfahren zur oligomerisierung von olefinen mit optimierter destillation | |
| EP1581485B1 (de) | Verfahren zur herstellung von alkylarylsulfonaten mittels modifizierter, dimerisierter olefine | |
| EP0124744B1 (de) | Hydrierkatalysator, Verfahren zu seiner Herstellung und seine Verwendung | |
| DE10206845A1 (de) | Modifiziertes Verfahren zur Herstellung von Tensidalkoholen und Tensidalkoholethern, die hergestellten Produkte und ihre Verwendung | |
| EP1856018A2 (de) | Verfahren zur herstellung von propen aus 2-buten- und isobuten-reichen feedströmen | |
| EP1784476B1 (de) | Verfahren zur herstellung von c5-aldehyden und propen aus einem 1-buten-und 2-buten-haltigen c4-strom | |
| EP3808720A1 (de) | Verfahren zur oligomerisierung von olefinen mit stoffströmen mit reduziertem olefingehalt | |
| WO2002016290A2 (de) | Verfahren zur synthese von terminalen olefinen mit enger molgewichtsverteilung | |
| EP3909940B1 (de) | Verfahren zur oligomerisierung von olefinen mit kontrolle des gehalts an oligomeren in den zu oligomerisierenden kohlenwasserstoffströmen | |
| EP2734489A1 (de) | Aufarbeitung olefinhaltiger c4-kohlenwasserstoffgemische | |
| DE10118634A1 (de) | Verfahren zur Herstellung von Olefinen | |
| MXPA00006839A (en) | Process for the preparation of c5-/c6-olefins | |
| DE10214442A1 (de) | Verfahren zur Herstellung von C¶6¶-Alkenen aus einem C¶4¶-Alkene enthaltenden Kohlenwasserstoffstrom | |
| DE10103309A1 (de) | Verfahren zur Herstellung höherer Alpha-Olefine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |