JP4607113B2 - イソブテン含有の物質流中の酸素含有及び/又は窒素含有の化合物の含量の減少 - Google Patents
イソブテン含有の物質流中の酸素含有及び/又は窒素含有の化合物の含量の減少 Download PDFInfo
- Publication number
- JP4607113B2 JP4607113B2 JP2006529825A JP2006529825A JP4607113B2 JP 4607113 B2 JP4607113 B2 JP 4607113B2 JP 2006529825 A JP2006529825 A JP 2006529825A JP 2006529825 A JP2006529825 A JP 2006529825A JP 4607113 B2 JP4607113 B2 JP 4607113B2
- Authority
- JP
- Japan
- Prior art keywords
- zeolite
- isobutene
- material stream
- nitrogen
- oxygen
- 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.)
- Expired - Lifetime
Links
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims abstract description 77
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims abstract description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 239000001301 oxygen Substances 0.000 title claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 title claims abstract description 18
- 239000000463 material Substances 0.000 title claims description 33
- 239000010457 zeolite Substances 0.000 claims abstract description 57
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 47
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000011148 porous material Substances 0.000 claims abstract description 18
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000002685 polymerization catalyst Substances 0.000 claims description 4
- 229910015900 BF3 Inorganic materials 0.000 claims description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910001424 calcium ion Inorganic materials 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910001415 sodium ion Inorganic materials 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 239000007788 liquid Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001179 sorption measurement Methods 0.000 description 9
- DFVOXRAAHOJJBN-UHFFFAOYSA-N 6-methylhept-1-ene Chemical compound CC(C)CCCC=C DFVOXRAAHOJJBN-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 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
- HNFSPSWQNZVCTB-UHFFFAOYSA-N 2-methyl-2-propan-2-yloxypropane Chemical compound CC(C)OC(C)(C)C HNFSPSWQNZVCTB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- -1 acetaldehyde, ketones Chemical class 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 101100057159 Caenorhabditis elegans atg-13 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 229910004283 SiO 4 Inorganic materials 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 235000013844 butane Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000011159 matrix material Substances 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
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000547 structure data Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
- C07C7/13—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers by molecular-sieve technique
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/08—Alkenes with four carbon atoms
- C07C11/09—Isobutene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Gas Separation By Absorption (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
Description
2(T−283K)/10K・I/v≦500min
好ましくは
2(T−283K)/10K・I/v≦350min
に従う。
本発明は次の例に詳細に説明される。
特定の濃度の酸素含有及び窒素含有の不純物を有するイソブテン含有の炭化水素を、ゼオライトで充填されたカラムに導通させた。引き続いて酸素含有もしくは窒素含有の不純物の濃度及びイソオクテン類含量を測定した。結果は次の表中にまとめられており、その際に全ての百分率の記載は質量%であり、かつ全てのppm−記載は質量ppmである(GC−分析により測定)。表中で次の省略形が使用される:MTBE=メチル−t−ブチルエーテル;IPTBE=イソプロピル−t−ブチルエーテル;IBTBE=イソブチル−t−ブチルエーテル。
Claims (7)
- イソブテンポリマーを製造する方法において、
a.物質流を液相中で温度T[単位:K]で及び線速度v[単位:cm/min]で0.3〜1.5nmの平均孔径の酸不含ゼオライトの固定床に導通させることによって少なくとも20質量%のイソブテン含量を有する物質流中の酸素含有及び/又は窒素含有の化合物の含量を減少させ、その際に固定床が物質流の流動方向において長さI[単位:cm]を有し、かつT、v及びIが方程式
2(T−283K)/10K・I/v≦350minに従い、ここでTが−25〜20℃の範囲内であり、かつvが0.5〜35cm/minの範囲内であり、
b.物質流を、三フッ化ホウ素−ベースの重合触媒を使用するイソブテンポリマーの製造に使用する
ことを特徴とする、イソブテンポリマーを製造する方法。 - 物質流がイソブテンとは異なる炭化水素をさらに含有する、請求項1記載の方法。
- 物質流がハロゲン化炭化水素をさらに含有する、請求項1記載の方法。
- ゼオライトが電荷補償のためのナトリウムイオン及び/又はカルシウムイオンを含有する、請求項1から3までのいずれか1項記載の方法。
- ゼオライトがゼオライトA、ゼオライトL、ゼオライトX及びゼオライトYの中から選択されている、請求項1から4までのいずれか1項記載の方法。
- 物質流をゼオライト処理の前に乾燥させる、請求項1から5までのいずれか1項記載の方法。
- 物質流を、物質流の流動方向に対して流れの上方へ0.3〜0.4nmの平均孔径を有するゼオライト及び流れの下方へ少なくとも0.5nmの平均孔径を有するゼオライトを含んでいる固定床に導通させる、請求項1から6までのいずれか1項記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10322153A DE10322153A1 (de) | 2003-05-16 | 2003-05-16 | Verringerung des Gehalts an sauerstoffhaltigen und/oder stickstoffhaltigen Verbindungen in isobutenhaltigen Stoffströmen |
PCT/EP2004/005200 WO2004101477A2 (de) | 2003-05-16 | 2004-05-14 | Verringerung des gehalts an sauerstoffhaltigen und/oder stickstoffhaltigen verbindungen in isobutenhaltigen stoffströmen |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007508254A JP2007508254A (ja) | 2007-04-05 |
JP4607113B2 true JP4607113B2 (ja) | 2011-01-05 |
Family
ID=33394684
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006529825A Expired - Lifetime JP4607113B2 (ja) | 2003-05-16 | 2004-05-14 | イソブテン含有の物質流中の酸素含有及び/又は窒素含有の化合物の含量の減少 |
Country Status (8)
Country | Link |
---|---|
US (1) | US7399404B2 (ja) |
EP (1) | EP1626945B1 (ja) |
JP (1) | JP4607113B2 (ja) |
KR (1) | KR101090578B1 (ja) |
CN (1) | CN100337999C (ja) |
AT (1) | ATE404512T1 (ja) |
DE (2) | DE10322153A1 (ja) |
WO (1) | WO2004101477A2 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090023882A1 (en) * | 2006-02-23 | 2009-01-22 | Basf Se | Process for preparation of polyisobutylene whose content of terminal double bonds is more than 50% from an industrial c4 hydrocarbon stream comprising 1-butene, 2-butene and isobutene |
FR3074802B1 (fr) * | 2017-12-13 | 2019-12-06 | IFP Energies Nouvelles | Procede d'elimination simultanee d'isobutanal et d'acetone de charges olefiniques par adsorption sur un materiau zeolithique |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU1011624A1 (ru) | 1981-12-11 | 1983-04-15 | Грозненский Ордена Трудового Красного Знамени Нефтяной Институт Им.Акад.М.Д.Миллионщикова | Способ очистки изобутилена от карбонильных соединений |
CA2003404C (en) * | 1988-11-22 | 2002-03-12 | John J. Cikut | Minimizing deactivation of ether synthesis catalyst |
US5120881A (en) * | 1988-11-22 | 1992-06-09 | Exxon Chemical Patents Inc | Removal of nitrogenous components of a hydrocarbon feedstream |
US5292990A (en) * | 1988-12-07 | 1994-03-08 | Exxon Research & Engineering Co. | Zeolite composition for use in olefinic separations |
DE3914817C2 (de) * | 1989-05-05 | 1995-09-07 | Huels Chemische Werke Ag | Verfahren zur Oligomerisierung von Olefinen |
US5245107A (en) * | 1991-06-18 | 1993-09-14 | Uop | Liquid phase adsorption process |
BE1006694A5 (fr) | 1991-06-22 | 1994-11-22 | Basf Ag | Procede de preparation de polyisobutenes extremement reactifs. |
DE69127473T2 (de) | 1991-11-18 | 1998-02-19 | Amoco Corp | Bf3-tertiäre etheratkomplexe zur isobuthylen-polymerisation |
US5271835A (en) * | 1992-05-15 | 1993-12-21 | Uop | Process for removal of trace polar contaminants from light olefin streams |
DE4226302A1 (de) | 1992-08-08 | 1994-02-10 | Basf Ag | Verfahren zur Abtrennung von Acetaldeyhd von Kohlenwasserstoffen |
US5427689A (en) * | 1994-10-17 | 1995-06-27 | Phillips Petroleum Company | Separation of polar substances from hydrocarbons |
US6632766B2 (en) * | 2000-12-08 | 2003-10-14 | Uop Llc | Composite adsorbents for purifying hydrocarbon streams |
-
2003
- 2003-05-16 DE DE10322153A patent/DE10322153A1/de not_active Withdrawn
-
2004
- 2004-05-14 CN CNB2004800134621A patent/CN100337999C/zh not_active Expired - Lifetime
- 2004-05-14 US US10/556,091 patent/US7399404B2/en active Active
- 2004-05-14 KR KR1020057021484A patent/KR101090578B1/ko active IP Right Grant
- 2004-05-14 JP JP2006529825A patent/JP4607113B2/ja not_active Expired - Lifetime
- 2004-05-14 EP EP04739206A patent/EP1626945B1/de not_active Expired - Lifetime
- 2004-05-14 DE DE502004007844T patent/DE502004007844D1/de not_active Expired - Lifetime
- 2004-05-14 WO PCT/EP2004/005200 patent/WO2004101477A2/de active IP Right Grant
- 2004-05-14 AT AT04739206T patent/ATE404512T1/de not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
WO2004101477A3 (de) | 2005-01-06 |
DE10322153A1 (de) | 2004-12-02 |
CN100337999C (zh) | 2007-09-19 |
WO2004101477A2 (de) | 2004-11-25 |
DE502004007844D1 (de) | 2008-09-25 |
EP1626945A2 (de) | 2006-02-22 |
KR20060009328A (ko) | 2006-01-31 |
CN1791566A (zh) | 2006-06-21 |
EP1626945B1 (de) | 2008-08-13 |
ATE404512T1 (de) | 2008-08-15 |
US20070106107A1 (en) | 2007-05-10 |
JP2007508254A (ja) | 2007-04-05 |
KR101090578B1 (ko) | 2011-12-08 |
US7399404B2 (en) | 2008-07-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2303819B1 (fr) | PROCEDE DE PURIFICATION DE 2,3,3,3-TETRAFLUORO-1-PROPENE (HF01234yf) | |
KR101343652B1 (ko) | 1-부텐, 2-부텐 및 이소부텐을 포함하는 공업용 c4 탄화수소 스트림으로부터 말단 이중 결합의 함량이 50% 초과인 폴리이소부틸렌을 제조하는 방법 | |
DE60307908T2 (de) | Verfahren zur Reinigung von Hexafluor-1,3-Butadien | |
US20100228071A1 (en) | Adsorbents for Purification of C2-C3 Olefins | |
US6111162A (en) | Process for removing oxygenated contaminants from hydrocarbon streams | |
US11214530B2 (en) | Method for the separation of C4 olefin mixtures | |
EP2158021A1 (en) | Process for reducing carbon monoxide in olefin-containing hydrocarbon feedstocks | |
JP6835061B2 (ja) | ヘキサフルオロブタジエンの精製方法 | |
US3969223A (en) | Olefin separation process | |
JPS5858387B2 (ja) | アルケンノコツカクイセイカホウ | |
JP4607113B2 (ja) | イソブテン含有の物質流中の酸素含有及び/又は窒素含有の化合物の含量の減少 | |
US3888939A (en) | Process for separating olefins by adsorption | |
JP2542394B2 (ja) | ヘキサフロロプロピレンの精製方法 | |
JPH0323566B2 (ja) | ||
CN114713209B (zh) | 一种氟化物改性吸附剂及六氟-1,3-丁二烯粗品的纯化方法 | |
US4036744A (en) | Olefin separation process | |
US4250270A (en) | Solution polymerization with molecular sieve purification of recycled solvent | |
EP3085681B1 (en) | Method for purifying hydrofluorocarbon compound | |
SU1011624A1 (ru) | Способ очистки изобутилена от карбонильных соединений | |
WO1997027165A1 (fr) | Processus de purification de fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether | |
KR20180126376A (ko) | 모사 이동층 자일렌 분리 공정, 및 파라자일렌-풍부 공급물을 처리하는 유닛에 최적화된 작동 조건 | |
KR100725003B1 (ko) | 디에틸벤젠 이성질체 혼합물로부터 1,2-디에틸벤젠을분리하는 방법 | |
JP4083423B2 (ja) | 有機溶剤の精製方法 | |
KR20030069482A (ko) | 디에틸벤젠 이성질체 혼합물로부터 1,4-디에틸벤젠 및1,3-디에틸벤젠을 분리하는 방법 | |
CN117425639A (zh) | 用于产生三氟乙烯以及再循环氯三氟乙烯料流的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20090611 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090618 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20090916 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20090928 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20091016 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20100910 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20101006 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4607113 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131015 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |