JP5539229B2 - 直鎖状アルファオレフィンを調製する方法 - Google Patents
直鎖状アルファオレフィンを調製する方法 Download PDFInfo
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- JP5539229B2 JP5539229B2 JP2010544609A JP2010544609A JP5539229B2 JP 5539229 B2 JP5539229 B2 JP 5539229B2 JP 2010544609 A JP2010544609 A JP 2010544609A JP 2010544609 A JP2010544609 A JP 2010544609A JP 5539229 B2 JP5539229 B2 JP 5539229B2
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- 239000004711 α-olefin Substances 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 150000001412 amines Chemical class 0.000 claims description 59
- 239000003054 catalyst Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 23
- 238000006384 oligomerization reaction Methods 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 18
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 17
- 239000005977 Ethylene Substances 0.000 claims description 17
- 239000003518 caustics Substances 0.000 claims description 10
- 230000009849 deactivation Effects 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- -1 cyclic amine Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000001179 sorption measurement Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 239000002815 homogeneous catalyst Substances 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 150000003754 zirconium Chemical class 0.000 claims description 3
- 229910007926 ZrCl Inorganic materials 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000003606 oligomerizing effect Effects 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- CTOUNSPKBGUFNA-UHFFFAOYSA-N 3-ethylheptan-1-amine Chemical compound CCCCC(CC)CCN CTOUNSPKBGUFNA-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical group CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
- FYNMXTGXYLXMCP-UHFFFAOYSA-J 2-methylpropanoate zirconium(4+) Chemical group [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 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 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
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/30—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
-
- 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
- C07C2531/025—Sulfonic acids
-
- 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
- C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- 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
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Inorganic Chemistry (AREA)
Description
(i) オリゴマー化反応装置にエチレン、溶媒および触媒を供給し、
(ii) この反応装置内でエチレンをオリゴマー化させ、
(iii) 反応装置から反応装置出口配管系を通じて、溶媒、直鎖状アルファオレフィン、エチレン、および触媒を含む反応装置出口流を取り出し、
(iv) この反応装置出口流を触媒失活および除去工程に移し、
(v) この反応装置出口流から触媒を除去する
各工程を有してなり、
少なくとも1種類の有機アミンがオリゴマー化反応装置および/または反応装置出口配管系に加えられることを特徴とする方法により達成される。
Claims (11)
- 溶媒および均一系触媒の存在下でのエチレンのオリゴマー化により直鎖状アルファオレフィン(LAO)を調製する方法であって、
(i) オリゴマー化反応装置にエチレン、溶媒および触媒を供給し、
(ii) 前記反応装置内でエチレンをオリゴマー化させ、
(iii) 前記反応装置から反応装置出口配管系を通じて、溶媒、直鎖状アルファオレフィン、エチレン、および触媒を含む反応装置出口流を取り出し、
(iv) 前記反応装置出口流を触媒失活および除去工程に移し、
(v) 前記反応装置出口流から前記触媒を除去する、
各工程を有してなり、
少なくとも1種類の有機アミンが前記反応装置出口配管系に加えられ、前記有機アミンが、蒸留、抽出または吸着により、前記反応装置出口流から除去され、除去された前記有機アミンが、前記反応装置出口配管系に再循環され、前記有機アミンが直鎖状アルファオレフィンを含有する有機相中に可溶性であり、前記有機アミンが水中または水と苛性アルカリの混合物中に不溶性であるかまたは低い溶解度を有し、前記触媒が苛性アルカリにより失活される、
ことを特徴とする方法。 - 前記アミンが連続的に加えられることを特徴とする請求項1記載の方法。
- 前記有機アミンが第一級、第二級、第三級または環状アミンであることを特徴とする請求項1または2記載の方法。
- 除去された前記有機アミンが、前記溶媒と一緒に、前記反応装置出口配管系に再循環されることを特徴とする請求項1から3いずれか1項記載の方法。
- 加えられた前記アミンが溶媒中に溶解していることを特徴とする請求項1から4いずれか1項記載の方法。
- 前記アミンが、前記反応装置出口配管系内で、混合装置により、前記反応装置出口流と混合されることを特徴とする請求項1から5いずれか1項記載の方法。
- 前記アミンが、使用される前記溶媒の沸点よりも20℃以下しか違わない沸点を有することを特徴とする請求項1から6いずれか1項記載の方法。
- 前記触媒が有機酸のジルコニウム塩および少なくとも1種類の有機アルミニウム化合物を含むことを特徴とする請求項1から7いずれか1項記載の方法。
- 前記ジルコニウム塩が式ZrCl4-mXmを有し、ここで、X=OCORまたはOSO3R’、RおよびR’が独立して、アルキル、アルケンまたはフェニルであり、0<m<4であることを特徴とする請求項8記載の方法。
- 前記有機アミンが、塩化物に対して0.1から2.0モル当量の量で加えられることを特徴とする請求項9記載の方法。
- 前記少なくとも1種類のアルミニウム化合物が、一般式R1nAl3-nまたはAl2Y3R1 3を有し、ここで、R1は、1から20の炭素原子を有するアルキル基を表し、YはCl、BrまたはIを表し、nは1<n<2の範囲内に任意の数であることを特徴とする請求項8から10いずれか1項記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08001677.7 | 2008-01-30 | ||
EP08001677 | 2008-01-30 | ||
PCT/EP2009/000030 WO2009095147A1 (en) | 2008-01-30 | 2009-01-07 | Method for preparing linear alpha-olefins |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2011510939A JP2011510939A (ja) | 2011-04-07 |
JP2011510939A5 JP2011510939A5 (ja) | 2012-01-05 |
JP5539229B2 true JP5539229B2 (ja) | 2014-07-02 |
Family
ID=39473285
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010544609A Active JP5539229B2 (ja) | 2008-01-30 | 2009-01-07 | 直鎖状アルファオレフィンを調製する方法 |
Country Status (15)
Country | Link |
---|---|
US (1) | US9593055B2 (ja) |
EP (1) | EP2234945B1 (ja) |
JP (1) | JP5539229B2 (ja) |
KR (1) | KR101545369B1 (ja) |
CN (2) | CN105753622B (ja) |
BR (1) | BRPI0907001B1 (ja) |
CA (1) | CA2711093C (ja) |
ES (1) | ES2520091T3 (ja) |
MX (1) | MX2010008426A (ja) |
MY (1) | MY156865A (ja) |
RU (1) | RU2469014C2 (ja) |
SG (1) | SG187514A1 (ja) |
TW (1) | TWI422558B (ja) |
WO (1) | WO2009095147A1 (ja) |
ZA (1) | ZA201004482B (ja) |
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RU2469014C2 (ru) | 2008-01-30 | 2012-12-10 | Линде Аг | Способ получения линейных альфа-олефинов |
ES2439261T3 (es) * | 2009-07-24 | 2014-01-22 | Linde Ag | Procedimiento de preparación de alfa-olefinas lineales |
EP2455359B1 (en) | 2010-11-23 | 2013-03-27 | Linde AG | Method for purification of a hydrocarbon stream olefin and amine |
EP2581358B1 (en) | 2011-10-10 | 2017-07-12 | Saudi Basic Industries Corporation | Method for removal of organic amines from hydrocarbon streams |
EP2738152B1 (en) * | 2012-11-28 | 2019-05-01 | Saudi Basic Industries Corporation | Method for removal and recovery of organic amines from a hydrocarbon stream |
JP2017503027A (ja) * | 2014-01-20 | 2017-01-26 | サウディ ベーシック インダストリーズ コーポレイション | アミンから、直鎖アルファ−オレフィン(lao)を含む炭化水素流を精製する方法及び装置系 |
CA2971693C (en) * | 2014-12-23 | 2019-09-24 | Public Joint Stock Company "Sibur Holding" | Methods of precipitating polymer and deactivated organometallic catalyst in an olefin oligomerization reaction |
KR101679515B1 (ko) | 2015-02-12 | 2016-11-24 | 주식회사 엘지화학 | 올리고머화 촉매계의 제조방법 및 이에 의해 제조된 올리고머화 촉매계 |
WO2016129845A1 (ko) * | 2015-02-12 | 2016-08-18 | 주식회사 엘지화학 | 비활성화제 및 이를 이용한 올레핀 올리고머화의 부산물 저감 방법 |
KR101761395B1 (ko) | 2015-04-15 | 2017-07-25 | 주식회사 엘지화학 | 리간드 화합물, 올리고머화 촉매계 및 이를 이용한 올레핀 올리고머화 방법 |
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US10519077B2 (en) | 2015-09-18 | 2019-12-31 | Chevron Phillips Chemical Company Lp | Ethylene oligomerization/trimerization/tetramerization reactor |
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FR3061175B1 (fr) * | 2016-12-22 | 2020-07-31 | Ifp Energies Now | Procede de neutralisation d'un systeme catalytique de dimerisation d'olefines contenant au moins un derive halogene. |
EP3558905A1 (en) * | 2016-12-22 | 2019-10-30 | SABIC Global Technologies B.V. | Methods of producing linear alpha olefins |
US20200055800A1 (en) * | 2017-05-09 | 2020-02-20 | Exxonmobil Chemical Patents Inc. | Linear Alpha Olefin Process Using Solvent Flash Drum for Olefin Separation |
CN110621704A (zh) * | 2017-05-09 | 2019-12-27 | 埃克森美孚化学专利公司 | 使用低聚反应器中温度控制的线性α-烯烃方法 |
WO2018208376A1 (en) * | 2017-05-09 | 2018-11-15 | Exxonmobil Chemical Patents Inc. | Linear alpha olefin process using catalyst deactivation with high product purity |
KR102334363B1 (ko) | 2017-09-29 | 2021-12-02 | 에스케이이노베이션 주식회사 | 올레핀의 올리고머화 방법 |
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-
2009
- 2009-01-07 RU RU2010136280/04A patent/RU2469014C2/ru not_active IP Right Cessation
- 2009-01-07 CA CA2711093A patent/CA2711093C/en active Active
- 2009-01-07 WO PCT/EP2009/000030 patent/WO2009095147A1/en active Application Filing
- 2009-01-07 BR BRPI0907001-0A patent/BRPI0907001B1/pt not_active IP Right Cessation
- 2009-01-07 KR KR1020107016520A patent/KR101545369B1/ko active IP Right Grant
- 2009-01-07 MY MYPI2010003554A patent/MY156865A/en unknown
- 2009-01-07 ES ES09705284.9T patent/ES2520091T3/es active Active
- 2009-01-07 US US12/735,585 patent/US9593055B2/en active Active
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ZA201004482B (en) | 2011-09-28 |
MX2010008426A (es) | 2011-02-22 |
CA2711093A1 (en) | 2009-08-06 |
KR20100113534A (ko) | 2010-10-21 |
SG187514A1 (en) | 2013-02-28 |
TW200940479A (en) | 2009-10-01 |
BRPI0907001B1 (pt) | 2018-04-03 |
ES2520091T3 (es) | 2014-11-11 |
WO2009095147A1 (en) | 2009-08-06 |
JP2011510939A (ja) | 2011-04-07 |
CN105753622A (zh) | 2016-07-13 |
TWI422558B (zh) | 2014-01-11 |
EP2234945A1 (en) | 2010-10-06 |
CN105753622B (zh) | 2019-01-29 |
MY156865A (en) | 2016-04-15 |
CN101932541A (zh) | 2010-12-29 |
RU2469014C2 (ru) | 2012-12-10 |
US20110046429A1 (en) | 2011-02-24 |
EP2234945B1 (en) | 2014-08-20 |
KR101545369B1 (ko) | 2015-08-18 |
US9593055B2 (en) | 2017-03-14 |
RU2010136280A (ru) | 2012-03-10 |
BRPI0907001A2 (pt) | 2015-07-07 |
CA2711093C (en) | 2013-05-21 |
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