FI121426B - Process för framställning av polyolefiner - Google Patents
Process för framställning av polyolefiner Download PDFInfo
- Publication number
- FI121426B FI121426B FI20065405A FI20065405A FI121426B FI 121426 B FI121426 B FI 121426B FI 20065405 A FI20065405 A FI 20065405A FI 20065405 A FI20065405 A FI 20065405A FI 121426 B FI121426 B FI 121426B
- Authority
- FI
- Finland
- Prior art keywords
- catalyst
- distillation column
- process according
- reactor
- dimerization
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 76
- 229920000098 polyolefin Polymers 0.000 title description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 126
- 238000004821 distillation Methods 0.000 claims abstract description 96
- 238000006471 dimerization reaction Methods 0.000 claims abstract description 70
- 230000003197 catalytic effect Effects 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 230000002378 acidificating effect Effects 0.000 claims abstract description 17
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 15
- 239000007787 solid Substances 0.000 claims abstract description 14
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 claims description 41
- 150000001336 alkenes Chemical class 0.000 claims description 31
- 239000002199 base oil Substances 0.000 claims description 26
- 238000005984 hydrogenation reaction Methods 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 14
- 239000010457 zeolite Substances 0.000 claims description 13
- 229910052782 aluminium Inorganic materials 0.000 claims description 12
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 12
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
- 229910021536 Zeolite Inorganic materials 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000002808 molecular sieve Substances 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- -1 aluminum silicates Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 description 72
- 238000006243 chemical reaction Methods 0.000 description 53
- 239000000178 monomer Substances 0.000 description 46
- 239000000539 dimer Substances 0.000 description 39
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 21
- 239000002585 base Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000006384 oligomerization reaction Methods 0.000 description 10
- 230000008929 regeneration Effects 0.000 description 10
- 238000011069 regeneration method Methods 0.000 description 10
- 239000013638 trimer Substances 0.000 description 10
- 238000004064 recycling Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000005336 cracking Methods 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- JLQFVGYYVXALAG-CFEVTAHFSA-N yasmin 28 Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.C([C@]12[C@H]3C[C@H]3[C@H]3[C@H]4[C@@H]([C@]5(CCC(=O)C=C5[C@@H]5C[C@@H]54)C)CC[C@@]31C)CC(=O)O2 JLQFVGYYVXALAG-CFEVTAHFSA-N 0.000 description 5
- 239000004711 α-olefin Substances 0.000 description 5
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 229920013639 polyalphaolefin Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000011973 solid acid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000013335 mesoporous material Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KUQIWULJSBTNPX-HWKANZROSA-N (e)-octadec-2-ene Chemical compound CCCCCCCCCCCCCCC\C=C\C KUQIWULJSBTNPX-HWKANZROSA-N 0.000 description 1
- OBDUMNZXAIUUTH-HWKANZROSA-N (e)-tetradec-2-ene Chemical compound CCCCCCCCCCC\C=C\C OBDUMNZXAIUUTH-HWKANZROSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910003294 NiMo Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/005—Mixtures of molecular sieves comprising at least one molecular sieve which is not an aluminosilicate zeolite, e.g. from groups B01J29/03 - B01J29/049 or B01J29/82 - B01J29/89
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J29/00—Catalysts comprising molecular sieves
- B01J29/03—Catalysts comprising molecular sieves not having base-exchange properties
- B01J29/0308—Mesoporous materials not having base exchange properties, e.g. Si-MCM-41
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/041—Mesoporous materials having base exchange properties, e.g. Si/Al-MCM-41
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/084—Y-type faujasite
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7007—Zeolite Beta
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/80—Mixtures of different zeolites
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/90—Regeneration or reactivation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/04—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst
- B01J38/12—Treating with free oxygen-containing gas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/12—Catalytic processes with crystalline alumino-silicates or with catalysts comprising molecular sieves
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/01—Processes of polymerisation characterised by special features of the polymerisation apparatus used
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
-
- 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
- C10G50/00—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1011—Biomass
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1088—Olefins
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/40—Characteristics of the process deviating from typical ways of processing
- C10G2300/4087—Catalytic distillation
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- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/40—Characteristics of the process deviating from typical ways of processing
- C10G2300/44—Solvents
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/10—Lubricating oil
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- 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
- Y02P20/10—Process efficiency
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- 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
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- 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
- Y02P20/584—Recycling of catalysts
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
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- Crystallography & Structural Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Catalysts (AREA)
Claims (15)
1. Process för framställning av polyo le finer, kännetecknad därav, att en inmatning, som omfattar en n-olefin eller en blandning av n-olefiner och väljs bland C8-C30 nolefiner, dimeriseras i närvaro av en fast sur katalysator pä sädant sätt, att inmatningen leds tili en katalytisk destillator, som omfattar antingen a) en kombination av en 10 destillationskolonn och en reaktor, vilken kombination omfattar minst en katalysatorbädd, eller b) en destillationskolonn, tili vilken är anslutna en eller flera sidoreaktorer, som omfattar minst ett katalysatorskikt och katalysator omfattar ett fast surt katalysatormaterial, vars mesoporyta är över 100 m2/g, 15 aluminiumhalten är 0,2-30 vikt-%, mängden sura punkter är 50 - 500 pmol/g och som väljs bland sura amorfa aluminiumsilikater, dealuminerade Yzeo liter och mesoporösa molekylsiktar, i vilka har inbäddats zcolit, dcn orcagcradc n-olcfincn tas ut frän dcn övrc dclcn av destillationskolonnen eller kombinationen av destillationskolonn 20 och reaktor som ett sidoflöde, som förenas med inmatningen, och den frän dimeriseringen erhällna reaktionsprodukten hydreras.
2. Process enligt patentkravet 1, kännetecknad därav, att inmatningen omfattar minst en n-olefin, som väljs bland 1-deken, blandningar av 25 dekener, 1-dodeken, blandningar av dodekener, 1-hexadeken, blandningar av hexadekener, 1-teradeken, 1-oktadeken, blandningar av oktadekener, l-C2o-C22-olefiner och blandningar av dessa.
3. Process enligt patentkravet 1 eller 2, kännetecknad därav, att 30 katalysatormaterialets mesoporyta är över 300 m2/g.
4. Process enligt nägot av patentkraven 1-3, kännetecknad därav, att katalysatormaterialet är ett amorft aluminiumsilikat, vars mesoporyta är over 300 m2/g.
5. Process enligt nägot av patentkraven 1 - 4, kännetecknad därav, att katalysatormaterial är mesoporös molekylsikt, i vilken har inbäddats zeolit, och zeoliten är ZSM-5, beta-zeolit eller MCM-22 och den mesoporösa molekylsikten är MCM-41, som har en regelbunden molekylstruktur. 10
6. Process enligt nägot av patentkraven 1-5, kännetecknad därav, att en del av sidoflödet avlägsnas frän den övre delen av destillationskolonnen eller kombinationen av destillationskolonn och reaktor. 15
7. Process enligt nägot av patentkraven 1-6, kännetecknad därav, att i inmatningen tillsätts ett lösningsmedel eller en blandning av lösningsmcdcl valda bland kolvätcn.
8. Process enligt nägot av patentkraven 1 - 7, kännetecknad därav, att en torkning genornförs pä inmatningen.
9. Process enligt nägot av patentkraven 1-8, kännetecknad därav, att dimeriseringen genomförs vid en temperatur av 25-200 °C, 25 fördelaktigt 50-150 °C, och vid ett tryck pä 0,001 mbar - 50 bar, fördelaktigt 0,5 mbar - 30 bar. 1 Process enligt nägot av patentkraven 1-9, kännetecknad därav, att hydreringen genomförs vid ett tryck pä 5-100 bar, fördelaktigt vid 30 ett tryck pä 10-70 bar, och vid en temperatur av 100-400 °C, fördelaktigt vid en temperatur av 150-250 °C, i närvaro av en hydreringskatalysator.
11. Process enligt nägot av patentkraven 1-10, kännetecknad därav, 5 att inmatningen omfattar 1-deken.
12. Process enligt nägot av patentkraven 1-11, kännetecknad därav, att inmatningen omfattar 1-hexadeken.
13. Process enligt nägot av patentkraven 1 - 12, kännetecknad därav, att inmatningen omfattar olefiner av bioursprung, vilka är framställda av biologiska räämnen.
14. Process enligt nägot av patentkraven 1-13, kännetecknad därav, 15 att destination genomförs efter dimeriseringen eller efter hydreringen eller efter vardera.
15. Process enligt nägot av patentkraven 1-14, kännetecknad därav, att en basolja eller en basoljekomponent framställs med processen. 20
16. Användning av en anläggning, som omfattar 1) en altemativ tork för en inmatning, 2) en katalytisk destillator, som omfattar antingen a) en kombination av en destillationskolonn och en reaktor, vilken kombination omfattar minst en katalysatorbädd omfattande en fast och 25 sur katalysator, eller b) en destillationskolonn, tili vilken är anslutna en eller flera sidoreaktorer, som omfattar minst en katalysatorbädd omfattande en fast och sur katalysator, 3) en hydreringsreaktor, och en altemativ destillationskolonn efter den katalytiska destillatom och/eller hydreringsreaktom, i en process enligt nägot av patentkraven 30 1-15.
Priority Applications (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI20065405A FI121426B (sv) | 2006-06-14 | 2006-06-14 | Process för framställning av polyolefiner |
BRPI0713262A BRPI0713262B1 (pt) | 2006-06-14 | 2007-06-14 | processo para a produção de oligômeros de olefina |
KR1020097000726A KR101166477B1 (ko) | 2006-06-14 | 2007-06-14 | 올레핀 소중합체 제조 방법 |
EP07788742.0A EP2029701B2 (en) | 2006-06-14 | 2007-06-14 | Process for the manufacture of olefin oligomers |
RU2009100932/04A RU2437920C2 (ru) | 2006-06-14 | 2007-06-14 | Способ получения олефиновых олигомеров |
CA2654940A CA2654940C (en) | 2006-06-14 | 2007-06-14 | Process for the manufacture of olefin oligomers |
MYPI20085055A MY150103A (en) | 2006-06-14 | 2007-06-14 | Process for the manufacture of olefin oligomers |
MX2008015844A MX2008015844A (es) | 2006-06-14 | 2007-06-14 | Proceso para la manufactura de oligomeros de olefinas. |
AU2007259108A AU2007259108B2 (en) | 2006-06-14 | 2007-06-14 | Process for the manufacture of olefin oligomers |
PCT/FI2007/050357 WO2007144474A1 (en) | 2006-06-14 | 2007-06-14 | Process for the manufacture of olefin oligomers |
JP2009514830A JP2009539945A (ja) | 2006-06-14 | 2007-06-14 | オレフィンオリゴマーの製造方法 |
CN2007800268475A CN101490218B (zh) | 2006-06-14 | 2007-06-14 | 制备烯烃低聚物的方法 |
IL195733A IL195733A (en) | 2006-06-14 | 2008-12-04 | Procedure for the production of carbon-saturated oligomers |
ZA200810485A ZA200810485B (en) | 2006-06-14 | 2008-12-10 | Process for the manufacture of olefin oligomers |
JP2013175655A JP5715207B2 (ja) | 2006-06-14 | 2013-08-27 | オレフィンオリゴマーの製造方法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FI20065405 | 2006-06-14 | ||
FI20065405A FI121426B (sv) | 2006-06-14 | 2006-06-14 | Process för framställning av polyolefiner |
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FI20065405A0 FI20065405A0 (sv) | 2006-06-14 |
FI20065405A FI20065405A (sv) | 2007-12-15 |
FI121426B true FI121426B (sv) | 2010-11-15 |
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FI20065405A FI121426B (sv) | 2006-06-14 | 2006-06-14 | Process för framställning av polyolefiner |
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EP (1) | EP2029701B2 (sv) |
JP (2) | JP2009539945A (sv) |
KR (1) | KR101166477B1 (sv) |
CN (1) | CN101490218B (sv) |
AU (1) | AU2007259108B2 (sv) |
BR (1) | BRPI0713262B1 (sv) |
CA (1) | CA2654940C (sv) |
FI (1) | FI121426B (sv) |
IL (1) | IL195733A (sv) |
MX (1) | MX2008015844A (sv) |
MY (1) | MY150103A (sv) |
RU (1) | RU2437920C2 (sv) |
WO (1) | WO2007144474A1 (sv) |
ZA (1) | ZA200810485B (sv) |
Families Citing this family (7)
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CN103282331A (zh) * | 2011-01-13 | 2013-09-04 | 出光兴产株式会社 | 烯烃低聚物混合物的制造方法 |
RU2570650C1 (ru) * | 2015-02-26 | 2015-12-10 | Открытое акционерное общество "Нефтяная компания "Роснефть" | Способ получения олигомеров альфа-олефина c6, c8 или c10 |
CN109020774A (zh) * | 2018-10-23 | 2018-12-18 | 浙江捷达科技有限公司 | 一种十八烷的正构烷烃制备方法 |
CN113365965A (zh) * | 2019-01-31 | 2021-09-07 | 巴斯夫欧洲公司 | 用于烯烃二聚的催化法 |
SG10202004243TA (en) * | 2019-05-14 | 2020-12-30 | Evonik Operations Gmbh | Process for the oligomerization of olefins with control of the oligomer content in the hydrocarbon streams to be oligomerized |
US20220289644A1 (en) * | 2019-08-09 | 2022-09-15 | Exxonmobil Chemical Patents Inc. | Processes for producing poly alpha olefins and apparatuses therefor |
FI129793B (sv) | 2021-06-15 | 2022-08-31 | Neste Oyj | Förfarande och anordning för framställning av polyalfaolefiner |
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US3702886A (en) | 1969-10-10 | 1972-11-14 | Mobil Oil Corp | Crystalline zeolite zsm-5 and method of preparing the same |
US5053569A (en) * | 1990-03-28 | 1991-10-01 | Texaco Chemical Company | Process for oligomerizing olefins to prepare base stocks for synthetic lubricants |
WO1993000165A1 (en) * | 1991-06-21 | 1993-01-07 | Mobil Oil Corporation | Olefin oligomerization process |
FI96852C (sv) * | 1992-12-10 | 1996-09-10 | Neste Oy | Förfarande och anläggning för oligomerisering av olefiner |
US6284104B1 (en) * | 1999-03-04 | 2001-09-04 | Catalytic Distillation Technologies | Apparatus and process for hydrogenations |
US6274783B1 (en) * | 2000-03-20 | 2001-08-14 | Catalytic Distillation Technologies | Catalytic distillation process for the production of C8 alkanes |
US6703356B1 (en) * | 2000-03-23 | 2004-03-09 | Exxonmobil Research And Engineering Company | Synthetic hydrocarbon fluids |
DE10015002A1 (de) | 2000-03-25 | 2001-09-27 | Basf Ag | Verfahren zur Herstellung von Oligomeren |
US6518473B2 (en) * | 2001-01-11 | 2003-02-11 | Chevron U.S.A. Inc. | Dimerizing olefins to make lube base stocks |
US6734328B1 (en) * | 2002-11-08 | 2004-05-11 | Catalytic Distillation Technologies | Process for the selective hydrogenation of alkynes |
US7329788B2 (en) * | 2003-12-22 | 2008-02-12 | Neste Oil Oyj | Process for producing gasoline components |
HUE061093T2 (hu) | 2004-12-28 | 2023-05-28 | Neste Oyj | Eljárás katalitikus anyagok elõállítására |
US8299312B2 (en) * | 2005-10-28 | 2012-10-30 | Neste Oil Oyj | Process for dimerizing olefins |
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Publication number | Publication date |
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ZA200810485B (en) | 2009-10-28 |
EP2029701B2 (en) | 2021-10-20 |
MY150103A (en) | 2013-11-29 |
AU2007259108A1 (en) | 2007-12-21 |
BRPI0713262B1 (pt) | 2018-11-13 |
MX2008015844A (es) | 2009-01-12 |
CN101490218A (zh) | 2009-07-22 |
WO2007144474A1 (en) | 2007-12-21 |
FI20065405A0 (sv) | 2006-06-14 |
AU2007259108B2 (en) | 2011-03-24 |
IL195733A (en) | 2013-03-24 |
EP2029701A4 (en) | 2011-11-16 |
KR20090031901A (ko) | 2009-03-30 |
RU2437920C2 (ru) | 2011-12-27 |
KR101166477B1 (ko) | 2012-07-23 |
RU2009100932A (ru) | 2010-07-20 |
EP2029701A1 (en) | 2009-03-04 |
IL195733A0 (en) | 2009-09-01 |
JP2014001229A (ja) | 2014-01-09 |
CN101490218B (zh) | 2013-03-27 |
FI20065405A (sv) | 2007-12-15 |
JP2009539945A (ja) | 2009-11-19 |
BRPI0713262A2 (pt) | 2012-04-10 |
CA2654940A1 (en) | 2007-12-21 |
CA2654940C (en) | 2012-04-17 |
EP2029701B1 (en) | 2015-08-05 |
JP5715207B2 (ja) | 2015-05-07 |
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