JP6383778B2 - 非対称型ホスホニウムハロアルミナートイオン液体組成物 - Google Patents
非対称型ホスホニウムハロアルミナートイオン液体組成物 Download PDFInfo
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- JP6383778B2 JP6383778B2 JP2016500135A JP2016500135A JP6383778B2 JP 6383778 B2 JP6383778 B2 JP 6383778B2 JP 2016500135 A JP2016500135 A JP 2016500135A JP 2016500135 A JP2016500135 A JP 2016500135A JP 6383778 B2 JP6383778 B2 JP 6383778B2
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- Prior art keywords
- phosphonium
- ionic liquid
- formula
- tributyl
- catalyst
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- 239000002608 ionic liquid Substances 0.000 title claims description 102
- 239000000203 mixture Substances 0.000 title claims description 26
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 title claims description 23
- 239000003054 catalyst Substances 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 33
- 150000001336 alkenes Chemical class 0.000 claims description 30
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 19
- -1 phosphonium halo aluminate Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000005496 phosphonium group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- SNDRYHUSDCHSDJ-UHFFFAOYSA-N tributyl(dodecyl)phosphanium Chemical compound CCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC SNDRYHUSDCHSDJ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000007848 Bronsted acid Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- XWHWBFXGBNURIG-UHFFFAOYSA-N tributyl(pentyl)phosphanium Chemical compound CCCCC[P+](CCCC)(CCCC)CCCC XWHWBFXGBNURIG-UHFFFAOYSA-N 0.000 claims description 4
- KEBKZOUZLSSLHC-UHFFFAOYSA-N CCCCC(CCCC)(CCCC)CCCCCPCC Chemical compound CCCCC(CCCC)(CCCC)CCCCCPCC KEBKZOUZLSSLHC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- FWMRXUQEHGGAAC-UHFFFAOYSA-N hexyl(tripropyl)phosphanium Chemical group CCCCCC[P+](CCC)(CCC)CCC FWMRXUQEHGGAAC-UHFFFAOYSA-N 0.000 claims description 3
- VTFBDXOWNVTUKP-UHFFFAOYSA-N tributyl(hexyl)phosphanium Chemical compound CCCCCC[P+](CCCC)(CCCC)CCCC VTFBDXOWNVTUKP-UHFFFAOYSA-N 0.000 claims description 3
- KEHGIVWHHBDQAD-UHFFFAOYSA-N tributyl(octyl)phosphanium Chemical compound CCCCCCCC[P+](CCCC)(CCCC)CCCC KEHGIVWHHBDQAD-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- DCSBKXBAWZANHE-UHFFFAOYSA-N tributyl(decyl)phosphanium Chemical compound CCCCCCCCCC[P+](CCCC)(CCCC)CCCC DCSBKXBAWZANHE-UHFFFAOYSA-N 0.000 claims description 2
- MXQNBWIDSTWEKZ-UHFFFAOYSA-N tributyl(heptyl)phosphanium Chemical compound CCCCCCC[P+](CCCC)(CCCC)CCCC MXQNBWIDSTWEKZ-UHFFFAOYSA-N 0.000 claims description 2
- GXSTVCYVFSWJJI-UHFFFAOYSA-N tributyl(nonyl)phosphanium Chemical compound CCCCCCCCC[P+](CCCC)(CCCC)CCCC GXSTVCYVFSWJJI-UHFFFAOYSA-N 0.000 claims description 2
- PLUQXIYZFYXLOJ-UHFFFAOYSA-N tributyl(undecyl)phosphanium Chemical compound CCCCCCCCCCC[P+](CCCC)(CCCC)CCCC PLUQXIYZFYXLOJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 description 36
- 230000029936 alkylation Effects 0.000 description 30
- 239000000460 chlorine Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 230000008901 benefit Effects 0.000 description 6
- 150000002367 halogens Chemical group 0.000 description 6
- 239000001282 iso-butane Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000001449 anionic compounds Chemical class 0.000 description 3
- XHIHMDHAPXMAQK-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F XHIHMDHAPXMAQK-UHFFFAOYSA-N 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002892 organic cations Chemical class 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- XKFPGUWSSPXXMF-UHFFFAOYSA-N tributyl(methyl)phosphanium Chemical compound CCCC[P+](C)(CCCC)CCCC XKFPGUWSSPXXMF-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- REACWASHYHDPSQ-UHFFFAOYSA-N 1-butylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1 REACWASHYHDPSQ-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- PQYJRMFWJJONBO-UHFFFAOYSA-N Tris(2,3-dibromopropyl) phosphate Chemical compound BrCC(Br)COP(=O)(OCC(Br)CBr)OCC(Br)CBr PQYJRMFWJJONBO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 238000003442 catalytic alkylation reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229960004830 cetylpyridinium Drugs 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- ISSCHPHYBDRMCW-UHFFFAOYSA-N ethyl(hexyl)phosphane Chemical compound CCCCCCPCC ISSCHPHYBDRMCW-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 239000011829 room temperature ionic liquid solvent Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- UJHVZVXYELCZLX-UHFFFAOYSA-M tributyl(dodecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC UJHVZVXYELCZLX-UHFFFAOYSA-M 0.000 description 1
- YCBRTSYWJMECAH-UHFFFAOYSA-N tributyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC YCBRTSYWJMECAH-UHFFFAOYSA-N 0.000 description 1
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
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Description
式中、
R1〜R3は同じか、または異なり、それぞれはヒドロカルビルから選択され;
R4はR1〜R3とは異なり、ヒドロカルビルから選択され;
Xはハロゲンである。
対して耐性のある触媒は利点を提供する。対照的に、アルキル化に使用される固体触媒は、一般に水があることによって急速に失活する。イオン液体は、HFのような触媒よりも腐食性が低く、不揮発性であるなどの他の液体アルキル化触媒より優れたいくつかの利点もある。
式中、
R1〜R3は同じか、または異なり、それぞれはC1〜C8ヒドロカルビルから選択され;
R4はR1〜R3とは異なり、C1〜C15ヒドロカルビルから選択され;
Xはハロゲンである。
ただし、条件として、式(I)に従った四級ホスホニウムハロアルミナート化合物は、化合物トリブチルベンジルホスホニウム−Al2Cl7を含まない。
イソパラフィンは、イオン液体触媒の存在下、反応条件において反応してアルキレートを生成する。本イオン液体触媒は、HCl、HBr、HI及びそれらの混合物からなる群から選択されるブレンステッド酸共触媒を加えたホスホニウムベースのハロアルミナートイオン液体である。
くは、20℃から70℃の範囲であってもよい。圧力は、大気圧から8000kPaの範囲、好ましくは、反応物を液相に保つのに十分な圧力であってもよい。反応物の容器中での滞留時間は、数秒から数時間、好ましくは、0.5分から60分の範囲である。反応によって生じた熱は、当業者に知られている任意の手段を使用して除去されてもよい。反応器出口において、炭化水素相は、密度差に基づく重力沈降によって、または当業者に既知のその他の分離技術によってイオン液体相から分離される。その後、炭化水素は、蒸留によって分離され、変換されなかった開始イソパラフィンは、反応器に再循環させられる。
ートを生成するためのイオン液体触媒を含む。イソパラフィンは、パラフィンを含んでもよく、4から10個の炭素原子を有し、オレフィンは、2から10個の炭素原子を有する。一部の実施形態において、イオン液体触媒は、式(I)に従った四級ホスホニウムハロアルミナート化合物を含み、式中、R1、R2、R3及びR4は、4から12個の間の炭素原子を有するアルキル基であり、Xは群F、Cl、Br、Iのハロゲン及びそれらの混合物である。
トリブチルドデシルホスホニウムクロロアルミナートは、不活性雰囲気中で無水トリブチルドデシルホスホニウムクロリドをゆっくりと添加する2モルの無水塩化アルミニウムと混合することによって調製される室温イオン液体である。混合の数時間後に、淡黄色の液体が得られる。得られた酸性のILをイソブタンの2−ブテンによるアルキル化に触媒として使用した。
イソブタンの2−ブテンによるアルキル化を300ccの連続的撹拌式オートクレーブ中で行った。水分への曝露を避けるために8グラムのトリブチルドデシルホスホニウム(TBDDP)−Al2Cl7イオン液体及び80グラムのイソブタンを、グローブボックス中のオートクレーブに充填した。そのオートクレーブを、その後、窒素を使用して500psigに圧力をかけた。撹拌を1900rpmで開始した。8グラムのオレフィン原材料(10%のn−ペンタントレーサーを添加した2−ブテン原材料)を、その後、目標のi/oモル比の10:1に達するまで、0.5gオレフィン/g IL/hrのオレフィン空間速度でオートクレーブに充填した。撹拌を止め、イオン液体及び炭化水素相を30秒間沈降させた。(実際の分離はほぼ同時に起った)。その炭化水素相を、その後、GCにより分析した。この実施例に関しては、オートクレーブの温度を25℃に維持した。
一連のさまざまなホスホニウムクロロアルミナートイオン液体触媒を用いて、25℃(表2)、38℃(表3)及び50℃(表4)において実施例2の手順を繰り返した。Pベースのイオン液体とNベースのイオン液体の間の性能差を示すために、4つのイミダゾリウムまたはピリジニウムイオン液体を含めた。イオン液体は以下のものとした:A−トリブチルドデシルホスホニウム−Al2Cl7、B−トリブチルデシルホスホニウム−Al2Cl7、C−トリブチルオクチルホスホニウム−Al2Cl7、D−トリブチルヘキシルホスホニウム−Al2Cl7 E−トリブチルペンチルホスホニウム−Al2Cl7、F−トリブチルメチルホスホニウム−Al2Cl7、G−トリプロピルヘキシルホスホニウム−Al2Cl7、H−ブチルメチルイミダゾリウム−Al2Cl7、I−オクチルメチルイミダゾリウム−Al2Cl7、J−ブチルピリジニウム−Al2Cl7及びK−ヘキサデシルピリジニウム−Al2Cl7。
Claims (21)
- R1〜R3は同じである、請求項1に記載の式(I)に従った化合物。
- R 1 〜R 3 のそれぞれはブチルである、請求項1から2のいずれか一項に記載の式(I)に従った化合物。
- R 4 はC 5 〜C 8 アルキルである、請求項1から3のいずれか一項に記載の式(I)に従った化合物。
- R 4 はペンチルまたはヘキシルである、請求項4に記載の式(I)に従った化合物。
- 前記四級ホスホニウムハロアルミナートは、トリプロピルヘキシルホスホニウム−Al 2 X 7 ;トリブチルペンチルホスホニウム−Al 2 X 7 ;トリブチルヘキシルホスホニウム−Al 2 X 7 ;トリブチルヘプチルホスホニウム−Al 2 X 7 ;トリブチルオクチルホスホニウム−Al 2 X 7 ;トリブチルノニルホスホニウム−Al 2 X 7 ;トリブチルデシルホスホニウム−Al 2 X 7 ;トリブチルウンデシルホスホニウム−Al 2 X 7 ;及びトリブチルドデシルホスホニウム−Al 2 X 7 からなる群から選択される、請求項1に記載の式(I)に従った化合物。
- 前記四級ホスホニウムハロアルミナートは、トリブチルペンチルホスホニウム−Al 2 X 7 である、請求項6に記載の式(I)に従った化合物。
- 前記四級ホスホニウムハロアルミナートは、トリブチルヘキシルホスホニウム−Al 2 X 7 である、請求項6に記載の式(I)に従った化合物。
- 前記四級ホスホニウムハロアルミナートは、トリ−n−ブチルヘキシルホスホニウム−Al 2 X 7 である、請求項6または請求項8に記載の式(I)に従った化合物。
- 前記四級ホスホニウムハロアルミナートは、トリブチルヘプチルホスホニウム−Al 2 X 7 である、請求項6に記載の式(I)に従った化合物。
- 前記四級ホスホニウムハロアルミナートは、トリブチルオクチルホスホニウム−Al 2 X 7 である、請求項6に記載の式(I)に従った化合物。
- 前記四級ホスホニウムハロアルミナートは、トリブチルドデシルホスホニウム−Al 2 X 7 である、請求項6に記載の式(I)に従った化合物。
- XはClである、請求項1から12のいずれか一項に記載の式(I)に従った化合物。
- 請求項1から13のいずれか一項に記載の1つまたは複数の四級ホスホニウムハロアルミナート化合物を含むイオン液体組成物。
- オレフィンとイソパラフィンを反応させてアルキレートを生成するためのイオン液体触媒であって、前記触媒は、i)請求項1から13のいずれか一項に記載の四級ホスホニウムハロアルミナート化合物あるいはii)請求項14に記載のイオン液体組成物を含む、前記イオン液体触媒。
- 前記触媒は、20℃の温度において少なくとも50cStの初期動粘性率を有する、請求項15に記載のイオン液体触媒。
- 前記触媒は、50℃の温度において少なくとも20cStの初期動粘性率を有する、請求項15に記載のイオン液体触媒。
- 前記ホスホニウムハロアルミナート化合物のHR 4 の大気圧における沸点は、HR 1 の大気圧における沸点よりも少なくとも30℃高い、請求項15から17のいずれか一項に記載のイオン液体触媒。
- 共触媒をさらに含み、前記イオン液体触媒は前記共触媒と混合される、請求項15から18のいずれか一項に記載のイオン液体触媒。
- 前記共触媒は、HCl、HBr、HI及びそれらの混合物からなる群から選択されるブレンステッド酸である、請求項19に記載のイオン液体触媒。
- 前記ブレンステッド酸共触媒はHClである、請求項20に記載のイオン液体触媒。
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JP2016512496A (ja) | 2016-04-28 |
WO2014093485A1 (en) | 2014-06-19 |
CA2892533A1 (en) | 2014-06-19 |
SA515361041B1 (ar) | 2018-07-08 |
IL238821A0 (en) | 2015-06-30 |
US20140173775A1 (en) | 2014-06-19 |
US20140173781A1 (en) | 2014-06-19 |
CN104968790A (zh) | 2015-10-07 |
IL238608A0 (en) | 2015-06-30 |
RU2015127989A (ru) | 2017-01-19 |
WO2014143324A1 (en) | 2014-09-18 |
WO2014143304A1 (en) | 2014-09-18 |
AU2013359340A1 (en) | 2015-04-09 |
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