JPH07501044A - イソブチレン重合のためのbf↓3・第三エーテレート錯体 - Google Patents
イソブチレン重合のためのbf↓3・第三エーテレート錯体Info
- Publication number
- JPH07501044A JPH07501044A JP4506151A JP50615192A JPH07501044A JP H07501044 A JPH07501044 A JP H07501044A JP 4506151 A JP4506151 A JP 4506151A JP 50615192 A JP50615192 A JP 50615192A JP H07501044 A JPH07501044 A JP H07501044A
- Authority
- JP
- Japan
- Prior art keywords
- ether
- boron trifluoride
- complex
- butyl
- trifluoride etherate
- 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.)
- Granted
Links
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title abstract description 44
- 238000006116 polymerization reaction Methods 0.000 title description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 82
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical class FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims abstract description 31
- 125000001033 ether group Chemical group 0.000 claims abstract description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 7
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 83
- 229910015900 BF3 Inorganic materials 0.000 claims description 74
- 229920001083 polybutene Polymers 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 27
- 125000001183 hydrocarbyl group Chemical class 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 239000007795 chemical reaction product Substances 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- 239000003245 coal Substances 0.000 claims 1
- UHCUDTULHJDIKR-UHFFFAOYSA-N tert-butylboron Chemical group [B]C(C)(C)C UHCUDTULHJDIKR-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 29
- 239000003054 catalyst Substances 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 27
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000007789 gas Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 150000001336 alkenes Chemical class 0.000 description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 10
- 150000002170 ethers Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000008901 benefit Effects 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 8
- -1 Polypropylene Polymers 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000000977 initiatory effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 230000008707 rearrangement Effects 0.000 description 5
- JJNQHLLBFBGKEL-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]butane Chemical compound CCCCOC(C)(C)C JJNQHLLBFBGKEL-UHFFFAOYSA-N 0.000 description 4
- HNFSPSWQNZVCTB-UHFFFAOYSA-N 2-methyl-2-propan-2-yloxypropane Chemical compound CC(C)OC(C)(C)C HNFSPSWQNZVCTB-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000001282 iso-butane Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 241000894007 species Species 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000001612 separation test Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical class 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002816 fuel additive Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- TZEUDSUHMOPLQM-UHFFFAOYSA-N (2-methylpropan-2-yl)oxycyclohexane Chemical compound CC(C)(C)OC1CCCCC1 TZEUDSUHMOPLQM-UHFFFAOYSA-N 0.000 description 1
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- BWRSHLROMAZEBM-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]pentane Chemical compound CCCCCOC(C)(C)C BWRSHLROMAZEBM-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical group CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical group [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 description 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- URRHKOYTHDCSDA-UHFFFAOYSA-N 2,5,8,11-tetramethyldodec-2-ene Chemical group CC(C)CCC(C)CCC(C)CC=C(C)C URRHKOYTHDCSDA-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- FITVQUMLGWRKKG-UHFFFAOYSA-N 2-methyl-2-propoxypropane Chemical compound CCCOC(C)(C)C FITVQUMLGWRKKG-UHFFFAOYSA-N 0.000 description 1
- JWIOTWYGCKFGDG-UHFFFAOYSA-N 3-methyl-1-[(2-methylpropan-2-yl)oxy]butane Chemical compound CC(C)CCOC(C)(C)C JWIOTWYGCKFGDG-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241000276489 Merlangius merlangus Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 241000384512 Trachichthyidae Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical class 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BVBRZOLXXOIMQG-UHFFFAOYSA-N fluoroborane Chemical compound FB BVBRZOLXXOIMQG-UHFFFAOYSA-N 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JBXYCUKPDAAYAS-UHFFFAOYSA-N methanol;trifluoroborane Chemical compound OC.FB(F)F JBXYCUKPDAAYAS-UHFFFAOYSA-N 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 229920001959 vinylidene polymer Polymers 0.000 description 1
Classifications
-
- 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
- C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C2/20—Acids of halogen; Salts thereof ; Complexes thereof with organic compounds
-
- 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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/08—Butenes
- C08F110/10—Isobutene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
- C07C2527/1213—Boron fluoride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
Description
Claims (27)
- 1.錯体のエーテルが、エーテル酸素に結合した少なくとも1つの第三炭素を有 する三フッ化硼素エーテレート錯体。
- 2.エーテルが一般式: ▲数式、化学式、表等があります▼ [式中、R1はC1−C20ヒドロカルビル又はハロ置換ヒドロカルビルであり 、R2、R3、及びR4は同じか又は異なり、−CH2R′、−CH=R′′、 及び−C≡R′′′(R′、R′′、及びR′′′は同じか又は異なり、C1− C20ヒドロカルビル又はハロ置換ヒドロカルビルである)から成る群より選択 される]を有する請求項1記載の三フッ化硼素エーテレート錯体。
- 3.R2、R3、及びR4がメチルである請求項2記載の三フッ化硼素エーテレ ート錯体。
- 4.R1を、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、 及び第三ブチルから成る群より選択する請求項3記載の三フッ化硼素エーテレー ト錯体。
- 5.Rlがメチルである請求項4記載の三フッ化硼素エーテレート錯体。
- 6.R1がブチルである請求項4記載の三フッ化硼素エーテレート錯体。
- 7.R1がイソプロピルである請求項4記載の三フッ化硼素エーテレート錯体。
- 8.安定な三フッ化硼素エーテレート錯体を得るのに適当な条件下で、エーテル 酸素に結合した少なくとも1つの第三炭素を有するエーテルを、三フッ化硼素と 反応させることによって得られる三フッ化硼素エーテレート組成物。
- 9.エーテルが一般式: ▲数式、化学式、表等があります▼ [式中、R1はC1−C20ヒドロカルビル又はハロ置換ヒドロカルビルであり 、R2、R3、及びR4は同じか又は異なり、−CH2R′、−CH=R′′、 及び−C≡R′′′(R′、R′′、及びR′′′は同じか又は異なり、C1− C20ヒドロカルビル又はハロ置換ヒドロカルビルである)から成る群より選択 される]を有する請求項8記載の三フッ化硼素エーテレート組成物。
- 10.R2、R3、及びR4がメチル;Rがメチル、エチル、プロピル、イソプ ロピル、ブチル、イソブチル、及び第三ブチルであり、約0.8:1−3:1の モル比で、エーテルと三フッ化硼素とを反応させることによって得られる請求項 9記載の三フッ化硼素エーテレート錯体。
- 11.割合が、少なくとも約1:1である請求項10記載の三フッ化硼素エーテ レート錯体。
- 12.R1がメチルである請求項10記載の三フッ化硼素エーテレート錯体。
- 13.R1がノルマルブチルである請求項10記載の三フッ化硼素エーテレート 錯体。
- 14.R1がイソプロピルである請求項10記載の三フッ化硼素エーテレート錯 体。
- 15.R1が第三ブチルである請求項10記載の三フッ化硼素エーテレート錯体 。
- 16.供給原料を、エーテルがエーテル酸素に桔合した少なくとも1つの第三炭 素を有する三フッ化硼素エーテレート錯体と接触させる工程を含む、1−オレフ ィン又はそれらの混合物を含む供給原料を重合させるための方法。
- 17.少なくとも約80%のビニリデン含有率を有するポリブテンが得られる請 求項16記載の方法。
- 18.三フッ化硼素エーテレートが、一般式:▲数式、化学式、表等があります ▼ [式中、R1はC1−C20ヒドロカルビル又はハロ置換ヒドロカルビルであり 、R2、R3、及びR4は同じか又は異なり、−CH2R′、−CH=R′′、 及び−C≡R′′′(R′、R′′、及びR′′′は同じか又は異なり、C1− C20ヒドロカルビル又はハロ置換ヒドロカルビルである)から成る群より選択 される]を有する請求項16記載の方法。
- 19.R2、R3、及びR4がメチルである請求項18記載の方法。
- 20.R1を、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル 、及び第三ブチルから成る群より選択する請求項19記載の方法。
- 21.R1がメチルである請求項20記載の方法。
- 22.エーテレートが、少なくとも約1:1のモル比で反応させたエーテルと三 フッ化硼素との反応生成物である請求項21記載の方法。
- 23.R1がブチルである請求項20記載の方法。
- 24.エーテレートが、少なくとも約1:1のモル比で反応させたエーテルと三 フッ化硼素との反応生成物である請求項23記載の方法。
- 25.R1がイソプロピルである請求項20記載の方法。
- 26.エーテレートが、少なくとも約1:1のモル比で反応させたエーテルと三 フッ化硼素との反応生成物である請求項25記載の方法。
- 27.少なくとも約80%のビニリデン含有率を有するポリブテンが製造される 請求項19記載の方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US1991/008640 WO1993010063A1 (en) | 1991-11-18 | 1991-11-18 | Bf3-tertiary etherate complexes for isobutylene polymerization |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH07501044A true JPH07501044A (ja) | 1995-02-02 |
JP3119452B2 JP3119452B2 (ja) | 2000-12-18 |
Family
ID=22225973
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP04506151A Expired - Fee Related JP3119452B2 (ja) | 1991-11-18 | 1991-11-18 | イソブチレン重合のためのbf▲下3▼・第三エーテレート錯体 |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0646103B1 (ja) |
JP (1) | JP3119452B2 (ja) |
AT (1) | ATE157338T1 (ja) |
DE (1) | DE69127473T2 (ja) |
WO (1) | WO1993010063A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2022514281A (ja) * | 2018-12-17 | 2022-02-10 | アランセオ・シンガポール・プライヴェート・リミテッド | ターシャリーエーテルを用いてイソオレフィンポリマーを生成する方法 |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19520078A1 (de) * | 1995-06-07 | 1996-12-12 | Basf Ag | Verfahren zur Herstellung von niedermolekularem, hochreaktivem Polyisobuten |
US5821205A (en) | 1995-12-01 | 1998-10-13 | Chevron Chemical Company | Polyalkylene succinimides and post-treated derivatives thereof |
US6407186B1 (en) | 1997-12-12 | 2002-06-18 | Basf Aktiengesellschaft | Method for producing low-molecular, highly reactive polyisobutylene |
DE19825334A1 (de) * | 1998-06-05 | 1999-12-09 | Basf Ag | Verfahren zur Herstellung hochreaktiver Polyisobutene |
AU7123700A (en) | 1999-09-16 | 2001-04-17 | Texas Petrochemicals Lp | Process for preparing polyolefin products |
US6562913B1 (en) | 1999-09-16 | 2003-05-13 | Texas Petrochemicals Lp | Process for producing high vinylidene polyisobutylene |
US6884858B2 (en) | 1999-10-19 | 2005-04-26 | Texas Petrochemicals Lp | Process for preparing polyolefin products |
US6858188B2 (en) | 2003-05-09 | 2005-02-22 | Texas Petrochemicals, Lp | Apparatus for preparing polyolefin products and methodology for using the same |
US7037999B2 (en) | 2001-03-28 | 2006-05-02 | Texas Petrochemicals Lp | Mid-range vinylidene content polyisobutylene polymer product and process for producing the same |
HUP0301859A3 (en) | 2000-11-17 | 2005-03-29 | Basf Ag | Method for deactivating and recovering boron trifluoride when producing polyisobutenes |
DE10243576A1 (de) | 2002-09-19 | 2004-04-01 | Basf Ag | Verfahren zur Herstellung von Polyisobuten |
DE10303212A1 (de) | 2003-01-24 | 2004-08-05 | Basf Ag | Verfahren zur Herstellung von Polyisobuten |
DE10322153A1 (de) | 2003-05-16 | 2004-12-02 | Basf Ag | Verringerung des Gehalts an sauerstoffhaltigen und/oder stickstoffhaltigen Verbindungen in isobutenhaltigen Stoffströmen |
US8063154B2 (en) * | 2008-06-24 | 2011-11-22 | The University Of Southern Mississippi | Preparation of exo-olefin terminated polyolefins via quenching with alkoxysilanes or ethers |
US8859473B2 (en) | 2008-12-22 | 2014-10-14 | Chevron Oronite Company Llc | Post-treated additive composition and method of making the same |
US20100298507A1 (en) | 2009-05-19 | 2010-11-25 | Menschig Klaus R | Polyisobutylene Production Process With Improved Efficiencies And/Or For Forming Products Having Improved Characteristics And Polyisobutylene Products Produced Thereby |
MY185746A (en) | 2013-07-17 | 2021-06-03 | Basf Se | High-reactivity polyisobutylene having a high content of vinylidene double bonds in the side chains |
US10066035B2 (en) | 2015-12-07 | 2018-09-04 | Bridgestone Corporation | Catalyst systems and methods for preparation of 1,4-polybutadiene rubber |
CA3122590A1 (en) | 2018-12-21 | 2020-06-25 | Arlanxeo Singapore Pte. Ltd. | Continuous process for producing halogenated isoolefin copolymer |
WO2020132742A1 (en) | 2018-12-27 | 2020-07-02 | ARLANXEO Canada Inc. | Process for producing chlorinated butyl rubber |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA576759A (en) * | 1959-05-26 | Esso Research And Engineering Company | Dimerization of olefins | |
BE413964A (ja) * | 1935-02-27 | |||
US2559062A (en) * | 1945-11-27 | 1951-07-03 | Standard Oil Dev Co | Friedel-crafts metal halide-ether complexes as polymerization catalysts |
US2780664A (en) * | 1952-10-16 | 1957-02-05 | Exxon Research Engineering Co | Hydrocarbon drying oil |
GB804070A (en) * | 1957-05-17 | 1958-11-05 | Exxon Research Engineering Co | Dimerization of polypropylenes |
CA1070335A (en) * | 1974-09-16 | 1980-01-22 | Robert A. Osborn | Hydrocarbon-derived resins of piperylene and methyl branched tertiary olefin hydrocarbons |
US4189547A (en) * | 1974-09-16 | 1980-02-19 | The Goodyear Tire & Rubber Company | Hydrocarbon-derived resins of piperylene and methyl branched tertiary olefin hydrocarbons blended with other hydrocarbon resins |
GB8329082D0 (en) * | 1983-11-01 | 1983-12-07 | Bp Chem Int Ltd | Low molecular weight polymers of 1-olefins |
CA1338520C (en) * | 1986-08-25 | 1996-08-13 | Joseph P. Kennedy | Living polymerization of olefins to end-functionalized polymers |
US4849572A (en) * | 1987-12-22 | 1989-07-18 | Exxon Chemical Patents Inc. | Process for preparing polybutenes having enhanced reactivity using boron trifluoride catalysts (PT-647) |
US4859572A (en) * | 1988-05-02 | 1989-08-22 | Eastman Kodak Company | Dye sensitized photographic imaging system |
-
1991
- 1991-11-18 JP JP04506151A patent/JP3119452B2/ja not_active Expired - Fee Related
- 1991-11-18 DE DE69127473T patent/DE69127473T2/de not_active Expired - Lifetime
- 1991-11-18 AT AT92906260T patent/ATE157338T1/de not_active IP Right Cessation
- 1991-11-18 WO PCT/US1991/008640 patent/WO1993010063A1/en active IP Right Grant
- 1991-11-18 EP EP92906260A patent/EP0646103B1/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2022514281A (ja) * | 2018-12-17 | 2022-02-10 | アランセオ・シンガポール・プライヴェート・リミテッド | ターシャリーエーテルを用いてイソオレフィンポリマーを生成する方法 |
Also Published As
Publication number | Publication date |
---|---|
EP0646103B1 (en) | 1997-08-27 |
DE69127473D1 (en) | 1997-10-02 |
ATE157338T1 (de) | 1997-09-15 |
DE69127473T2 (de) | 1998-02-19 |
JP3119452B2 (ja) | 2000-12-18 |
WO1993010063A1 (en) | 1993-05-27 |
EP0646103A4 (en) | 1995-08-09 |
EP0646103A1 (en) | 1995-04-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH07501044A (ja) | イソブチレン重合のためのbf↓3・第三エーテレート錯体 | |
US5068490A (en) | BF3-tertiary etherate complexes for isobutylene polymerization | |
US5304615A (en) | Preparation of butene polymers using an ionic liquid | |
US5382739A (en) | Lubricating oils | |
SA90100129B1 (ar) | بلمرة كاتيونية للاوليفينات الاولية | |
CA2859545C (en) | Polymerization initiating system and method to produce highly reactive olefin functional polymers | |
WO2008142295A1 (fr) | Procédé d'oligomérisation des oléfines utilisant une composition catalytique comprenant un complexe organométallique contenant un ligand phenoxy fonctionnalisé par un hétéro-atome | |
US4041098A (en) | Method for the oligomerization of alpha-olefins | |
JP6594572B2 (ja) | 高反応性オレフィン機能性ポリマーを形成するための方法 | |
JP7078953B2 (ja) | 高反応性オレフィン機能性ポリマーを作製するための重合開始系および方法 | |
EP1081165B1 (en) | Method of dehalogenating hydrocarbon containing carbon-carbon double bond | |
US4855526A (en) | Process for preparing ethylene-higher olefin copolymer oils with Ziegler-Natta catalyst in mixed aliphatic-aromatic solvent | |
JP2019007007A (ja) | 重合開始系および極めて反応性の高いオレフィン官能性ポリマーの製造方法 | |
US4642410A (en) | Catalytic poly alpha-olefin process | |
US4594469A (en) | Method for the oligomerization of alpha-olefins | |
US4334113A (en) | Synthetic hydrocarbon oligomers | |
US10829573B1 (en) | Method for forming highly reactive olefin functional polymers | |
US2551638A (en) | Production of lubricating oils by condensation of olefinic hydrocarbons | |
JP7378344B2 (ja) | 高反応性ポリブテンの製造方法 | |
EP0556965A1 (en) | Poly(iso)butenes | |
US3474157A (en) | Polymerized ethylene pour point depressants from alkanol modified catalysts | |
CS272398B1 (en) | Method of poly-n-butene oils production | |
US3641191A (en) | Method for reduction of polymer formation in a process for converting ethylene to alpha olefins | |
US4339350A (en) | Catalyst prepared from tungsten hexafluoride and water | |
KR20220012206A (ko) | 고반응성 폴리이소부틸렌을 제조하기 위한 중합 촉매 시스템 및 제조방법 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
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 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20081013 Year of fee payment: 8 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091013 Year of fee payment: 9 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091013 Year of fee payment: 9 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101013 Year of fee payment: 10 |
|
LAPS | Cancellation because of no payment of annual fees |