CA1279308C - Methode de polymerisation du butene-1 - Google Patents

Methode de polymerisation du butene-1

Info

Publication number: CA1279308C
Authority: CA; Canada
Prior art keywords: component; catalyst system; butene; titanium; monomer
Prior art date: 1986-05-21
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

Application number

CA000512864A

Other languages

English (en)

Inventor

Robert Peter Nielsen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell USA Inc

Original Assignee

Shell Oil Co

Priority date (The priority date 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 date listed.)

1986-05-21

Filing date

1986-07-02

Publication date

1991-01-22

1986-07-02 Application filed by Shell Oil Co filed Critical Shell Oil Co

1991-01-22 Application granted granted Critical

1991-01-22 Publication of CA1279308C publication Critical patent/CA1279308C/fr

2008-01-22 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

230000000379 polymerizing effect Effects 0.000 title claims abstract description 12
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 title claims description 34
238000000034 method Methods 0.000 title claims description 20
239000010936 titanium Substances 0.000 claims abstract description 72
-1 hydride compounds Chemical class 0.000 claims abstract description 64
239000003054 catalyst Substances 0.000 claims abstract description 61
229910052719 titanium Inorganic materials 0.000 claims abstract description 35
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 24
239000003795 chemical substances by application Substances 0.000 claims abstract description 18
150000001875 compounds Chemical class 0.000 claims abstract description 15
239000011777 magnesium Substances 0.000 claims abstract description 10
229910052749 magnesium Inorganic materials 0.000 claims abstract description 10
125000003118 aryl group Chemical group 0.000 claims abstract description 9
150000002148 esters Chemical class 0.000 claims abstract description 8
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical group CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 30
238000006116 polymerization reaction Methods 0.000 claims description 26
MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims description 22
229920001748 polybutylene Polymers 0.000 claims description 21
239000000178 monomer Substances 0.000 claims description 20
HRAQMGWTPNOILP-UHFFFAOYSA-N 4-Ethoxy ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(OCC)C=C1 HRAQMGWTPNOILP-UHFFFAOYSA-N 0.000 claims description 6
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
229910052782 aluminium Inorganic materials 0.000 claims description 4
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 4
150000004678 hydrides Chemical class 0.000 claims description 4
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical group Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 3
SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 claims description 3
XPYQFIISZQCINN-QVXDJYSKSA-N 4-amino-1-[(2r,3e,4s,5r)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrate Chemical compound O.O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 XPYQFIISZQCINN-QVXDJYSKSA-N 0.000 claims description 2
239000002585 base Substances 0.000 claims description 2
150000005690 diesters Chemical class 0.000 claims description 2
229910001629 magnesium chloride Inorganic materials 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 2
CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 claims description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims 2
HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 claims 1
MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 claims 1
239000000306 component Substances 0.000 abstract 5
229920000642 polymer Polymers 0.000 description 25
230000000694 effects Effects 0.000 description 5
239000000460 chlorine Substances 0.000 description 4
ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 description 2
239000002879 Lewis base Substances 0.000 description 2
150000007527 lewis bases Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
JZJCVRDSZUSNNS-UHFFFAOYSA-N 4-ethyl-4-methoxycyclohexa-1,5-diene-1-carboxylic acid Chemical compound CCC1(OC)CC=C(C(O)=O)C=C1 JZJCVRDSZUSNNS-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229910021380 Manganese Chloride Inorganic materials 0.000 description 1
GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 1
CQGRLHBOVUGVEA-UHFFFAOYSA-N OOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOO CQGRLHBOVUGVEA-UHFFFAOYSA-N 0.000 description 1
101100004969 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CAT2 gene Proteins 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000003426 co-catalyst Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000011565 manganese chloride Substances 0.000 description 1
235000002867 manganese chloride Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000003801 milling Methods 0.000 description 1
125000005498 phthalate group Chemical group 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction 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
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
238000004260 weight control Methods 0.000 description 1

Landscapes

Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

CA000512864A 1986-05-21 1986-07-02 Methode de polymerisation du butene-1 Expired - Lifetime CA1279308C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US86532886A	1986-05-21	1986-05-21
US865,328		1986-05-21

Publications (1)

Publication Number	Publication Date
CA1279308C true CA1279308C (fr)	1991-01-22

Family

ID=25345258

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000512864A Expired - Lifetime CA1279308C (fr)	1986-05-21	1986-07-02	Methode de polymerisation du butene-1

Country Status (1)

Country	Link
CA (1)	CA1279308C (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111269341A (zh) *	2020-04-09	2020-06-12	青岛科技大学	一种合成高等规聚丁烯的催化剂及其制备方法

1986
- 1986-07-02 CA CA000512864A patent/CA1279308C/fr not_active Expired - Lifetime

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111269341A (zh) *	2020-04-09	2020-06-12	青岛科技大学	一种合成高等规聚丁烯的催化剂及其制备方法
CN111269341B (zh) *	2020-04-09	2023-03-21	青岛科技大学	一种合成高等规聚丁烯的催化剂及其制备方法

Legal Events

Date	Code	Title	Description
2003-01-22	MKLA	Lapsed

Publication	Publication Date	Title
US4927797A (en)	1990-05-22	Catalyst system for the polymerization of olefins
JP3640024B2 (ja)	2005-04-20	高引張強度の無定形１−ブテン／プロピレン共重合体
KR0138631B1 (ko)	1998-05-01	에틸렌 중합용 티타늄촉매성분, 에틸렌 중합촉매 및 그를 사용한 에틸렌중합방법
US5276115A (en)	1994-01-04	Mono-1-olefin polymerization in the presence of hydrogen and a cyclopentadienyl compound
US5214114A (en)	1993-05-25	Process for producing ethylene polymers
EP0823919A1 (fr)	1998-02-18	Procede et constituant catalyseur pour la copolymerisation et l'homopolymerisation d'olefines
US4621124A (en)	1986-11-04	Catalyst system for the polymerization of ethylene
US6339136B1 (en)	2002-01-15	Process for making propylene homo or copolymers
US5162465A (en)	1992-11-10	Preparation of homopolymers and copolymers of propene using a Ziegler-Natta catalyst system
AU638861B2 (en)	1993-07-08	Cocatalytic composition which is usable for the polymerisation of alpha-olefins
JPH0422924B2 (fr)	1992-04-20
US4308357A (en)	1981-12-29	Block copolymerization process and product
US4656151A (en)	1987-04-07	Intermetallic compound
GB2157302A (en)	1985-10-23	Copolymerization catalyst and process
GB2103628A (en)	1983-02-23	Block copolymerization process
WO2001004166A1 (fr)	2001-01-18	Procede de production de polypropylene
GB2131033A (en)	1984-06-13	Process for producing an ethylene copolymer
US5071928A (en)	1991-12-10	Process for polymerizing ethylene and copolymerizing ethylene with alpha-olefins and relevant catalyst
US5115054A (en)	1992-05-19	Catalysts containing poly(3-ethyl-1-hexene) and uses thereof
EP0565173B1 (fr)	1997-06-04	Procédé de préparation de polyoléfines à large distribution de poids moléculaire
EP0366204B1 (fr)	1994-02-23	Procédé de polymérisation d'alcènes et composition de catalyseur utilisée dans ce procédé
CA2023096C (fr)	1996-08-20	Catalyseur pour la polymerisation d'olefines; methode de preparation et utilisation dudit catalyseur
PH26188A (en)	1992-03-18	Solid alkene polymerization catalyst components and process for their preparation
US4349483A (en)	1982-09-14	Process for the preparation of aluminum trihydrocarbyls
EP0493070A2 (fr)	1992-07-01	Composition à base d'un copolymère éthylène-propylène