JP5175104B2 - ポリオレフィン系合成油の調製方法 - Google Patents
ポリオレフィン系合成油の調製方法 Download PDFInfo
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- JP5175104B2 JP5175104B2 JP2007548125A JP2007548125A JP5175104B2 JP 5175104 B2 JP5175104 B2 JP 5175104B2 JP 2007548125 A JP2007548125 A JP 2007548125A JP 2007548125 A JP2007548125 A JP 2007548125A JP 5175104 B2 JP5175104 B2 JP 5175104B2
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- oligomerization
- olefin
- temperature
- rcl
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- 238000000034 method Methods 0.000 title claims abstract description 125
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- 238000006384 oligomerization reaction Methods 0.000 claims abstract description 102
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- 150000001336 alkenes Chemical class 0.000 claims abstract description 69
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 59
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 47
- 239000000203 mixture Substances 0.000 claims abstract description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 36
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 35
- 230000009471 action Effects 0.000 claims abstract description 33
- 238000006298 dechlorination reaction Methods 0.000 claims abstract description 30
- 125000002091 cationic group Chemical group 0.000 claims abstract description 25
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000004711 α-olefin Substances 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
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- 238000006467 substitution reaction Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- VQOXUMQBYILCKR-UHFFFAOYSA-N tridecaene Natural products CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G50/00—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
-
- 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G19/00—Refining hydrocarbon oils in the absence of hydrogen, by alkaline treatment
- C10G19/073—Refining hydrocarbon oils in the absence of hydrogen, by alkaline treatment with solid alkaline material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/04—Metals, or metals deposited on a carrier
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G50/00—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
- C10G50/02—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation of hydrocarbon oils for lubricating purposes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
-
- 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
- C07C2527/10—Chlorides
- C07C2527/11—Hydrogen chloride
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1003—Waste materials
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1088—Olefins
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1096—Aromatics or polyaromatics
Description
− 触媒調製手順が複雑で多数の操作を含むこと(AlCl3の昇華及び粉砕、錯体の調製)。
− これらの方法で得られた触媒が、粘ちょうで、くっつきやすい物質であり、オレフィンへの溶解性が低いこと、反応器の冷却した壁に強く付着するため、オリゴマー化の完了時に反応器からの排出が困難であること。
− オリゴマー化中に使用可能な触媒の活性が低いこと、体積比容量が大きい金属混合反応器を使用する必要が生じるといった要因。
− 得られる生成物について計算したときに、AlX3に関する消費係数が高いこと。
RnAlX3-n+R’X⇔[R’+(RnAlX4-n)-]⇔R’++(RnAlX4-n)-
2Al(O)+3(CH3)3CCl→2[(CH3)3C]1.5AlCl1.5 (1)
[(CH3)3C]1.5AlCl1.5+(CH3)3CCl→(CH3)3C+{[(CH3)3C]1.5AlCl2.5}- (2)
(3):R−(C10H20)nC10H20 +AlCl4 -(AC)→R−(C10H20)nC10H20Cl+AlCl3
(4):RCl+(C2H5)3Al→{R+[(C2H5)3AlCl]-}→RH+C2H4+(C2H5)3AlCl (4)
KOH+C4H9OH→C4H9OK+H2O
C4H9OK+RCl→KCl+C4H9OR
R−(C10H20)x-1−C10H21Cl→HCl+R−(C10H20)x-1−C10H20(=)
1.解重合器は定常状態温度条件に10〜20分で達する。
2.特定温度条件に達した状態で、高分子量オリゴデセンの熱解重合は一定速度で進行する。
3.解重合速度、解重合生成物の収率、及び高分子量オリゴデセンの目標生成物への変換率は、温度が340℃から360度に上昇するにつれて単調増加する。
4.観察可能な解重合活性化エネルギーは27.5kcal/molと等しい(lgA=9.9073)。
5.高分子量オリゴデセンの解重合生成物への変換率は360℃で70%以上であり、その解重合生成物は、繰り返し分離するための塔を対象とした3mmHg以下の蒸留器内の残留圧力及びその温度にて解重合器から留去される。
6.解重合生成物は、内部(ビニレン)二重結合及びビニリデン二重結合を有する分子と一緒に、ビニル二重結合を有する多数の分子(約30モル%)を含有する点だけではなく、物理化学特性においてもデセン−1のオリゴマー化生成物とは異なる(表9、10)。
7.高分子量オリゴオレフィンの熱解重合は化学吸熱過程を示す。高分子量オリゴデセン1000kgを1時間で解重合するためには、合計容量が116kWのヒーターを設けなければならない。
熱供給−116kW/時間
熱消費−高分子量オリゴデセンの加熱(最高360℃) 30kW/時間
360℃での解重合の吸熱反応 33kW/時間
得られた生成物の蒸発 28kW/時間
蓄熱 11kW/時間
熱損失 14kW/時間
− 温度330〜360℃、残留圧力1.0mmHgにて、熱解重合法に使用する高分子量オリゴデセンは、高い変換率で低分子量生成物の混合物に再処理可能である。
− 熱解重合の高分子量生成物の混合物から、真空蒸留法を用いることにより、PAO−2、PAO−4及びPAO−6に近似する留分組成及び粘度特性に関する生成物の留分を分離可能である。
− 分離した留分の固化温度は、初期オリゴマー化物から分離したPAO−2、PAO−4及びPAO−6の固化温度を超えているが、粘度特性に関して相当する鉱物油の非混合(noncompounded)留分の固化温度を大幅に下回る。
Claims (8)
- 炭素原子を3〜14個含有するオレフィンのオリゴマー化によるポリオレフィン系合成油の調製方法であって、オレフィン原料及びカチオン性触媒系の成分溶液を調整し、直鎖α−オレフィンを異性化し、カチオン性アルミニウム含有触媒系の作用下で該オレフィン原料をオリゴマー化し、使用済み触媒をオリゴマー化物から分離し、該オリゴマー化物を留分に分離して、その分離した留分を水素化する工程を含み、オリゴマー化工程及び/又は使用済み触媒を該オリゴマー化物から分離する工程の直後に、該オリゴマー化物に存在するモノ塩素含有オリゴマーの脱塩素化工程を行い、該オリゴマー化物を留分に分離する工程の後で、かつ分離した留分を水素化する工程の前に、該オリゴマー化物を留分に分離する工程で蒸留器底分として分離した高分子量生成物を解重合する工程を行い、
炭素原子を3〜14個含有するオレフィンの前記オリゴマー化を、オリゴマー化可能な前記オレフィンとそのオリゴマー化生成物との混合物中で、又はオリゴマー化可能な前記オレフィンとそのオリゴマー化生成物及び芳香族炭化水素との混合物中で、触媒系Al(O)−HCl−(CH3)3CClの作用下、温度110〜180℃、Al(O)濃度0.02〜0.08g−原子/L、HCl/Al(O)モル比0.002〜0.06、及びRCl/Al(O)モル比1.0〜4.0で行い、該Al(O)が、粒径1〜100μmの粉末状アルミニウムであり、
使用する前記炭素原子を3〜14個含有するオレフィンが、炭素原子を4〜14個含有する、直鎖又は分岐のα−オレフィンと、イソオレフィン及び二重結合が分子内転位したオレフィン(「内部」オレフィン)との混合物で表され、その成分比が、α−オレフィン 0.5〜99.0質量%;イソオレフィン 0.5〜5.0質量%;「内部」オレフィン 残部であって合計100質量%であり、
前記オリゴマー化物から分離したオリゴ−オレフィンの留分の前記水素化を、未修飾のパラジウム−アルミナ担持触媒について計算したときに無水水酸化ナトリウムを30〜100質量%用いて修飾したパラジウム−アルミナ担持触媒の作用下、温度200〜250℃、水素圧力20気圧にて行うことを特徴とする方法。 - 前記オリゴマー化工程の直後に、オリゴマー化物に存在するモノ塩素含有オリゴマー(RCl)の前記脱塩素化を、粒径が1〜100μmの粉末状金属アルミニウムであるAl(O)を用い、Al(O)/RClモル比0.5〜2.0として、温度110〜180℃で30〜180分行うことを特徴とする、請求項1に記載の方法。
- 前記オリゴマー化工程の直後に、オリゴマー化物に存在するモノ塩素含有オリゴマー(RCl)の前記脱塩素化を、トリエチルアルミニウム(TEA)を用い、TEA/RClのモル比を0.5〜2.0として、温度95〜150℃で30〜180分行うことを特徴とする、請求項1に記載の方法。
- 使用済み触媒の前記分離工程の直後に、オリゴマー化物に存在するモノ塩素含有オリゴマー(RCl)の前記脱塩素化を、水酸化カリウム及び/又は水酸化ナトリウム(MOH)のアルコール溶液を用い、MOH/RClのモル比を1.1〜2.0として、温度120〜160℃で30〜240分行うことを特徴とする、請求項1又は2のいずれかに記載の方法。
- 使用済み触媒の前記分離工程の直後に、オリゴマー化物に存在するモノ塩素含有オリゴマー(RCl)の前記脱塩素化を、窒素、二酸化炭素、メタン又は過熱した水蒸気を用いて抜けていく塩化水素を吹き出しながら、温度280〜350℃、圧力1〜2barで30〜180分、そのオリゴマーを熱脱塩化水素化することによって行うことを特徴とする、請求項1又は2のいずれかに記載の方法。
- オリゴマー化物に存在するモノ塩素含有オリゴマー(RCl)の前記脱塩素化を、乾燥アルカリ金属水酸化物(MOH)の存在下、MOH/RClのモル比を1.1〜2.0として行うことを特徴とする、請求項1又は2のいずれかに記載の方法。
- 前記乾燥アルカリ金属水酸化物が、前記使用済み触媒のないオリゴマー化物とアルカリ金属水酸化物の5〜40%水溶液との混合物を温度100〜200℃に加熱して水を蒸留することによって、前記オリゴマー化物中に直接得られることを特徴とする、請求項6に記載の方法。
- 前記オリゴマー化物を留分に分離する工程で蒸留器底分の状態で分離した高分子量生成物の前記解重合を、解重合反応器からの生成物を連続的に除去しながら、温度330〜360℃、圧力1.0〜10.0mmHgで30〜120分、該高分子量生成物を加熱して行うことを特徴とする、請求項1に記載の方法。
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US5210362A (en) * | 1989-06-07 | 1993-05-11 | The Lubrizol Corporation | Alpha-olefin polymers |
US5196635A (en) * | 1991-05-13 | 1993-03-23 | Ethyl Corporation | Oligomerization of alpha-olefin |
US5550307A (en) * | 1994-03-24 | 1996-08-27 | Chevron Chemical Company | Increased dimer yield of olefin oligomers through catalyst modifications |
US5602085A (en) * | 1994-10-07 | 1997-02-11 | Mobil Oil Corporation | Multi-phase lubricant |
US5859303A (en) * | 1995-12-18 | 1999-01-12 | Phillips Petroleum Company | Olefin production |
US6096933A (en) * | 1996-02-01 | 2000-08-01 | Phillips Petroleum Company | Hydrocarbon hydrogenation and catalyst therefor |
US6106699A (en) * | 1997-04-29 | 2000-08-22 | Probex | Process for de-chlorinating and de-fouling oil |
RU2212935C2 (ru) * | 2001-04-05 | 2003-09-27 | Институт проблем химической физики РАН | Каталитическая система для катионной олигомеризации индивидуальных или смесей линейных олефинов |
-
2004
- 2004-12-22 RU RU2004137372/04A patent/RU2287552C2/ru active
-
2005
- 2005-12-21 US US11/792,908 patent/US20090054713A1/en not_active Abandoned
- 2005-12-21 KR KR1020077014080A patent/KR20070088724A/ko not_active Application Discontinuation
- 2005-12-21 UA UAA200707027A patent/UA84505C2/ru unknown
- 2005-12-21 CN CN2005800442646A patent/CN101087866B/zh not_active Expired - Fee Related
- 2005-12-21 MX MX2007007542A patent/MX2007007542A/es unknown
- 2005-12-21 WO PCT/RU2005/000655 patent/WO2006071135A1/en active Application Filing
- 2005-12-21 JP JP2007548125A patent/JP5175104B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
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RU2287552C2 (ru) | 2006-11-20 |
JP2008525568A (ja) | 2008-07-17 |
CN101087866A (zh) | 2007-12-12 |
RU2004137372A (ru) | 2006-06-10 |
MX2007007542A (es) | 2007-11-15 |
US20090054713A1 (en) | 2009-02-26 |
UA84505C2 (ru) | 2008-10-27 |
WO2006071135A1 (en) | 2006-07-06 |
CN101087866B (zh) | 2012-02-15 |
KR20070088724A (ko) | 2007-08-29 |
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