JP6567037B2 - 線状αオレフィンを調製するための触媒組成物および方法 - Google Patents
線状αオレフィンを調製するための触媒組成物および方法 Download PDFInfo
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- JP6567037B2 JP6567037B2 JP2017502785A JP2017502785A JP6567037B2 JP 6567037 B2 JP6567037 B2 JP 6567037B2 JP 2017502785 A JP2017502785 A JP 2017502785A JP 2017502785 A JP2017502785 A JP 2017502785A JP 6567037 B2 JP6567037 B2 JP 6567037B2
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- catalyst
- olefin
- cocatalyst
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- 239000003054 catalyst Substances 0.000 title claims description 144
- 239000000203 mixture Substances 0.000 title claims description 120
- 239000004711 α-olefin Substances 0.000 title claims description 90
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 238000006384 oligomerization reaction Methods 0.000 claims description 66
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 57
- 150000001336 alkenes Chemical class 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 56
- 239000005977 Ethylene Substances 0.000 claims description 54
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 claims description 53
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 51
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 51
- 229910052726 zirconium Inorganic materials 0.000 claims description 32
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 21
- -1 zirconium carboxylate Chemical class 0.000 claims description 21
- 230000003197 catalytic effect Effects 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 17
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- 238000006243 chemical reaction Methods 0.000 claims description 14
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- 230000003606 oligomerizing effect Effects 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
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- FYNMXTGXYLXMCP-UHFFFAOYSA-J 2-methylpropanoate zirconium(4+) Chemical compound [Zr+4].CC(C)C([O-])=O.CC(C)C([O-])=O.CC(C)C([O-])=O.CC(C)C([O-])=O FYNMXTGXYLXMCP-UHFFFAOYSA-J 0.000 description 4
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- 125000003118 aryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
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- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
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- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
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- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
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- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
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- 125000001931 aliphatic group Chemical group 0.000 description 1
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
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- 230000002860 competitive effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
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- 150000002367 halogens Chemical group 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
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- C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
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Description
nC2H4→CH3−(CH2)m−CH=CH2
(式中、mは奇数である)
Claims (8)
- 触媒および共触媒を含むエチレンのオリゴマー化のための触媒組成物であって、前記触媒が、カルボン酸ジルコニウムを含み、前記共触媒が、エチルアルミニウムセスキクロリドおよびジエチルアルミニウムクロリドを含み、Al:Zrのモル比が35:1であり、前記共触媒が質量で3:1の比でエチルアルミニウムセスキクロリドおよびジエチルアルミニウムクロリドを含むことを特徴とする触媒組成物。
- オレフィン、溶媒および触媒組成物を反応器にフィードするステップと;
前記オレフィンを前記反応器中でオリゴマー化して、線状αオレフィンを含む反応生成物を生成させるステップ;
を含むオレフィンのオリゴマー化のための方法であって、
前記触媒組成物が触媒および共触媒を含み;
前記触媒が、カルボン酸ジルコニウムを含み、
前記共触媒が、エチルアルミニウムセスキクロリドおよびジエチルアルミニウムクロリドを含み、Al:Zrのモル比が35:1であり、前記共触媒が質量で3:1の比でエチルアルミニウムセスキクロリドおよびジエチルアルミニウムクロリドを含む、ことを特徴とする方法。 - 請求項2に記載の方法であって、前記オレフィンがエチレンであり、前記溶媒がトルエンであることを特徴とする方法。
- 請求項2〜3のいずれか1項に記載の方法であって、前記触媒組成物が、78℃で、オレフィンのオリゴマー化のために使用される異なる触媒組成物より10%高い触媒活性を有し、前記線状αオレフィン反応生成物が、オレフィンのオリゴマー化のために使用される異なる触媒組成物と比べて、78℃で、2%以上の線状性の増大を有するC8−C18画分を含み、前記異なる触媒組成物は前記カルボン酸ジルコニウム触媒及びエチルアルミニウムセスキクロリドを有する、ことを特徴とする方法。
- 少なくとも90%の平均線状性を有するC4〜C14画分を含む、線状αオレフィン組成物の製造方法であって、C4線状αオレフィンが少なくとも99%の線状性を有し、C6線状αオレフィンが少なくとも98%の線状性を有し、C8線状αオレフィンが少なくとも96%の線状性を有し、C10−C20線状αオレフィンが少なくとも80%の線状性を有し、前記線状αオレフィン組成物の製造方法は、前記オレフィン、溶媒、触媒組成物を反応器に供給することと、前記反応器中で前記オレフィンをオリゴマー化し、線状αオレフィンを含む反応生成物を形成することとを含むプロセスを有し、前記触媒組成物は、触媒と共触媒とを含み、前記触媒はカルボン酸ジルコニウムを含み、前記共触媒はエチルアルミニウムセスキクロリドおよびジエチルアルミニウムクロリドを含み、Al:Zrのモル比が35:1であり、前記共触媒が質量で3:1の比でエチルアルミニウムセスキクロリドおよびジエチルアルミニウムクロリドを含む、ことを特徴とする線状αオレフィン組成物の製造方法。
- ポリエチレン組成物の製造方法であって、前記ポリエチレンが、オレフィン、溶媒、触媒組成物を反応器に供給することと、前記反応器中で前記オレフィンをオリゴマー化し、線状αオレフィンを含む反応生成物を形成することとを含むプロセスによって作製された少なくとも1つの線状αオレフィンから誘導される工程を有し、前記触媒組成物は、触媒と共触媒とを含み、前記触媒はカルボン酸ジルコニウムを含み、前記共触媒はエチルアルミニウムセスキクロリドおよびジエチルアルミニウムクロリドを含み、Al:Zrのモル比が35:1であり、前記共触媒が質量で3:1の比でエチルアルミニウムセスキクロリドおよびジエチルアルミニウムクロリドを含む、ことを特徴とするポリエチレン組成物の製造方法。
- カルボン酸ジルコニウム触媒および少なくとも2つの共触媒組合せを含む触媒組成物を含む反応を有するオレフィンオリゴマー化の方法であって、78℃での前記触媒組成物の触媒活性が、前記カルボン酸ジルコニウム触媒および前記少なくとも2つの共触媒組合せのうちの1つの共触媒を含む触媒組成物と比べて92%増大しており、前記少なくとも2つの共触媒組合せがエチルアルミニウムセスキクロリドおよびジエチルアルミニウムクロリドを含み、Al:Zrのモル比が35:1であり、前記共触媒が質量で3:1の比でエチルアルミニウムセスキクロリドおよびジエチルアルミニウムクロリドを含み、前記オレフィンがエチレンであることを特徴とするオレフィンオリゴマー化の方法。
- C4、C6およびC8線状オレフィン画分を含む線状αオレフィン組成物をもたらす、カルボン酸ジルコニウム触媒および少なくとも2つの共触媒組合せを含み、前記共触媒はエチルアルミニウムセスキクロリドおよびジエチルアルミニウムクロリドを含み、Al:Zrのモル比が35:1であり、前記共触媒が質量で3:1の比でエチルアルミニウムセスキクロリドおよびジエチルアルミニウムクロリドを含む、触媒組成物を含む反応を有するオレフィンオリゴマー化の方法であって、前記C4画分の純度が少なくとも99%であり、前記C6画分の純度が少なくとも98%であり、前記C8画分の純度が少なくとも96%であることを特徴とするオレフィンオリゴマー化の方法。
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KR20170032377A (ko) * | 2014-07-18 | 2017-03-22 | 사빅 글로벌 테크놀러지스 비.브이. | 선형 알파 올레핀 제조용 촉매 조성물 및 제조방법 |
CN108778479A (zh) * | 2016-03-21 | 2018-11-09 | 沙特基础工业全球技术有限公司 | 用于处理低聚产物流的方法 |
CN110431125A (zh) | 2017-03-14 | 2019-11-08 | 沙特阿拉伯石油公司 | 乙烯低聚反应生成α-烯烃的方法 |
FR3099476B1 (fr) * | 2019-07-31 | 2021-07-30 | Ifp Energies Now | Procede d’oligomerisation mettant en œuvre un recycle du ciel gazeux |
KR102462535B1 (ko) * | 2019-10-17 | 2022-11-01 | 주식회사 엘지화학 | 올리고머 제조 장치 |
FR3112775B1 (fr) * | 2020-07-24 | 2022-07-01 | Ifp Energies Now | Procédé d’oligomérisation mettant en oeuvre un recycle du ciel gazeux |
WO2023036767A1 (en) * | 2021-09-08 | 2023-03-16 | Sabic Global Technologies B.V. | Method for flushing reactor |
EP4183486A1 (en) * | 2021-11-23 | 2023-05-24 | Indian Oil Corporation Limited | Process and catalyst composition for producing linear alpha olefins in high yield by ethylene oligomerization |
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SG11201700034WA (en) | 2017-02-27 |
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KR20170032377A (ko) | 2017-03-22 |
RU2662219C1 (ru) | 2018-07-25 |
US10626063B2 (en) | 2020-04-21 |
TWI620761B (zh) | 2018-04-11 |
CN106536044A (zh) | 2017-03-22 |
WO2016009360A1 (en) | 2016-01-21 |
ES2913079T3 (es) | 2022-05-31 |
CA2954472A1 (en) | 2016-01-21 |
MX2017000723A (es) | 2017-10-16 |
BR112017000901A2 (pt) | 2017-11-21 |
TW201619209A (zh) | 2016-06-01 |
US20170210680A1 (en) | 2017-07-27 |
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JP2017522180A (ja) | 2017-08-10 |
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