JP5204765B2 - オレフィンを共二量化するための方法 - Google Patents
オレフィンを共二量化するための方法 Download PDFInfo
- Publication number
- JP5204765B2 JP5204765B2 JP2009513687A JP2009513687A JP5204765B2 JP 5204765 B2 JP5204765 B2 JP 5204765B2 JP 2009513687 A JP2009513687 A JP 2009513687A JP 2009513687 A JP2009513687 A JP 2009513687A JP 5204765 B2 JP5204765 B2 JP 5204765B2
- Authority
- JP
- Japan
- Prior art keywords
- olefin
- olefins
- catalyst
- oligomerization
- reaction
- 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.)
- Expired - Fee Related
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- 150000001336 alkenes Chemical class 0.000 title claims description 273
- 238000000034 method Methods 0.000 title claims description 71
- 230000008569 process Effects 0.000 title claims description 40
- 238000006471 dimerization reaction Methods 0.000 title claims description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 205
- 239000000203 mixture Substances 0.000 claims description 103
- 239000003054 catalyst Substances 0.000 claims description 94
- 238000006243 chemical reaction Methods 0.000 claims description 81
- 238000006384 oligomerization reaction Methods 0.000 claims description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 48
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 239000007795 chemical reaction product Substances 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 23
- 229910052759 nickel Inorganic materials 0.000 claims description 22
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 21
- 229930195733 hydrocarbon Natural products 0.000 claims description 21
- 150000002430 hydrocarbons Chemical class 0.000 claims description 21
- 239000010457 zeolite Substances 0.000 claims description 21
- 239000000539 dimer Substances 0.000 claims description 19
- 239000000047 product Substances 0.000 claims description 19
- 238000007037 hydroformylation reaction Methods 0.000 claims description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims description 17
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- 238000005984 hydrogenation reaction Methods 0.000 claims description 16
- 150000004760 silicates Chemical class 0.000 claims description 16
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 15
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 14
- KXYDGGNWZUHESZ-UHFFFAOYSA-N 4-(2,2,4-trimethyl-3h-chromen-4-yl)phenol Chemical compound C12=CC=CC=C2OC(C)(C)CC1(C)C1=CC=C(O)C=C1 KXYDGGNWZUHESZ-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 239000011148 porous material Substances 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 5
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- 238000005336 cracking Methods 0.000 claims description 3
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- WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 claims description 3
- UPSVYNDQEVZTMB-UHFFFAOYSA-N 2-methyl-1,3,5-trinitrobenzene;1,3,5,7-tetranitro-1,3,5,7-tetrazocane Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O.[O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UPSVYNDQEVZTMB-UHFFFAOYSA-N 0.000 claims 1
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- 125000004429 atom Chemical group 0.000 description 5
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- 238000004231 fluid catalytic cracking Methods 0.000 description 5
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- 239000002736 nonionic surfactant Substances 0.000 description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
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- 239000007848 Bronsted acid Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- 230000001476 alcoholic effect Effects 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
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- 238000006356 dehydrogenation reaction Methods 0.000 description 4
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- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
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- YNWSXIWHOSSPCO-UHFFFAOYSA-N rhodium(2+) Chemical class [Rh+2] YNWSXIWHOSSPCO-UHFFFAOYSA-N 0.000 description 1
- ITDJKCJYYAQMRO-UHFFFAOYSA-L rhodium(2+);diacetate Chemical compound [Rh+2].CC([O-])=O.CC([O-])=O ITDJKCJYYAQMRO-UHFFFAOYSA-L 0.000 description 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
- VXNYVYJABGOSBX-UHFFFAOYSA-N rhodium(3+);trinitrate Chemical compound [Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VXNYVYJABGOSBX-UHFFFAOYSA-N 0.000 description 1
- YWFDDXXMOPZFFM-UHFFFAOYSA-H rhodium(3+);trisulfate Chemical compound [Rh+3].[Rh+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O YWFDDXXMOPZFFM-UHFFFAOYSA-H 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229910000275 saponite Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical class C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
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- 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
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- C07C2/12—Catalytic processes with crystalline alumino-silicates or with catalysts comprising molecular sieves
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
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- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
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- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Description
a)ブテンフラクションに対して5質量%未満のイソブテンを含む、ブテンを含むC4の炭化水素流を、高められた温度でニッケルを含む不均一触媒と接触させ、
b)反応混合物からC12オレフィンフラクションを単離し、
c)C12オレフィンフラクションを一酸化炭素および水素との反応によってコバルト触媒の存在下、ヒドロホルミル化し、かつ
d)水素化する、
C13アルコール混合物の製造方法を記載している。
a)基本的にCnオレフィンから成る第1のオレフィン供給原料を調製し、かつ基本的にCmオレフィンから成る第2のオレフィン供給原料を調製し[式中、nとmは相互に独立して2〜12の互いに2つの異なる整数を表す]、かつ
b)第1の、および第2のオレフィン供給原料を、オレフィンオリゴマー化不均一触媒を用いて反応させる、
オレフィンを共二量化するための方法である。
0.5〜5質量%のイソブタン、
5〜30質量%のn−ブタン、
20〜40質量%のトランス−2−ブテン、
10〜20質量%のシス−2−ブテン、
25〜55質量%の1−ブテン、
0.5〜5質量%のイソブテン、
ならびにその都度最大1質量%の範囲にある微量ガス(Spurengas)、例えば1,3−ブタジエン、プロペン、プロパン、シクロプロパン、プロパジエン、メチルシクロプロパン、ビニルアセチレン、ペンテン、ペンタンなどである。
ブタン 26質量%、
i−ブテン 1質量%、
1−ブテン 26質量%、
トランス−2−ブテン 31質量%、
シス−2−ブテン 16質量%
オレフィンの多い第1の炭化水素混合物中にジオレフィンまたはアルキンが存在する場合、これらをオリゴマー化の前に好適には200質量ppm未満に混合物自体から除去することができる。それらを好ましくは選択的な水素化、例えばEP−81041、およびDE−1568542に記載の選択的な水素化によって、特に好ましくは選択的な水素化によって100質量ppm未満の残分、とりわけ10質量ppmの残分になるまで除去する。
ISO指数=(20x−6)/(3x+3)x=CH3プロトンと、CH2/CHプロトンとの比
好適にはオレフィン共二量体は、12の炭素原子を有するアルケンを、主にまたは完全に含む混合物である。好適にはこの際オレフィン共二量体は、全オレフィン含分に対して少なくとも70質量%の、特に好ましくは少なくとも85質量%、とりわけ少なくとも95質量%、特に少なくとも95質量%の、12の炭素原子を有するアルケンを含む。
a)基本的にCmオレフィンから成る第1のオレフィン供給原料を調製し、かつ基本的にCnオレフィンから成る第2のオレフィン供給原料を調製し[式中、nとmは相互に独立して、2〜12の互いに異なる2つの整数である]、
b)第1と第2のオレフィン供給原料を第1の反応帯域に供給し、かつオレフィンオリゴマー化不均一触媒を用いてオリゴマー化に供し、
c)第1の反応帯域の搬出物から、Cn+mオレフィン共二量体が濃縮された流れを分離し、
d)Cn+mオレフィン共二量体が濃縮された流れを第2の反応帯域に供給し、かつヒドロホルミル化触媒の存在下、一酸化炭素および水素との反応に供し、かつ
e)水素化する、
アルコールの製造方法である。
a)基本的にCnオレフィンから成る第1のオレフィン供給原料を調製し、かつ基本的にC2nオレフィンから成る第2のオレフィン供給原料を調製し[式中、nは2〜6の整数である]、
b)第1と第2のオレフィン供給原料を第1の反応帯域に供給し、かつオレフィンオリゴマー化不均一触媒を用いてオリゴマー化に供し、
c)第1の反応帯域の搬出物から、C3nオレフィン共二量体が濃縮された流れを分離し、
d)C3nオレフィン共二量体が濃縮された流れを第2の反応帯域に供給し、かつヒドロホルミル化触媒の存在下、一酸化炭素および水素との反応に供し、かつ
e)水素化する、
7〜19の炭素原子を有するアルコールの製造方法である。
工程d)におけるヒドロホルミル化のための適切な触媒は公知であり、かつ一般的には周期表の第VIIIの副族の元素の塩または錯化合物を含む。好適には、コバルト、ルテニウム、イリジウム、ロジウム、ニッケル、パラジウム、および白金から選択される第VIIIの副族の金属である。本発明による方法のために、好ましくは塩、およびとりわけロジウムの、またはコバルトの錯化合物を使用する。
水素化のために、ヒドロホルミル化の際に得られる反応混合物を水素化触媒の存在下、水素と反応させる。
(i)アルコキシ化、
(ii)グリコシド化、
(iii)硫酸化、
(iv)リン酸化、
(v)アルコキシ化、および以降の硫酸化、または
(vi)アルコキシ化、および以降のリン酸化、
に供することによって得られる、官能基化されたアルコール混合物に関する。
の化合物と、これらの混合物とから選択されている。
実施例1(本発明によるもの)
油で加熱したダブルジャケット型管式反応器(Doppelmantelrohrreaktor)(内径=6mm、全長=70cm)を、8mlの触媒砕片(直径1〜1.6mm)で満たした。触媒としては酸化アルミニウム(ベーマイト)によって結合剤として成形されたH−β−ゼオライト(SiO2:Al2O3のモル比24)を使用した。活性化を18時間、250℃で窒素流中で行った。この反応は25barの圧力下で行った。フィードとして、64質量%のC8オレフィンと、36質量%のC4オレフィンとの混合物12g/hを計量添加した。ISO指数1.08のC8オレフィンは、ブテン二量化に由来し、かつ主成分として3−メチルヘプテンを含んでいた。C4オレフィンの組成は次のようであった:1−ブテン(37%)、2−ブテン(42%)、イソ−ブテン(2%)、イソ−ブタン(3%)、n−ブタン(16%)。フィード流に対して付加的に、反応器に76g/hの循環流を貫流させた。
Claims (17)
- オレフィンを共二量化するための方法であって、
a)C nオレフィンを含む第1のオレフィン供給原料を調製し、かつISO指数として測定して0〜1.8の範囲のオレフィンの分枝度を有し、かつニッケル含有オリゴマー化触媒の存在下、ラフィネートIIの二量化によって得られる、C mオレフィンを含む第2のオレフィン供給原料を調製し[式中、nとmは相互に独立して2〜12の2つの互いに異なる整数を表す]、かつ
b)第1の、および第2のオレフィン供給原料を、触媒の全質量に対してニッケル含分が最大で1質量%のオレフィンオリゴマー化不均一触媒を用いて反応させる、オレフィンを共二量化するための方法。 - 工程a)においてC nオレフィンを含む第1の供給原料を調製し、かつC 2nオレフィンを含む第2の供給原料を調製する[式中、nは2〜6の整数を表す]、請求項1に記載の方法。
- nが4である、請求項2に記載の方法。
- 第1のオレフィン供給原料が、オレフィンの全含分に対して最高20質量%の分枝状のオレフィンの割合を有する、請求項1から3までのいずれか1項に記載の方法。
- 第1のオレフィン供給原料として、クラッキング法から得られる、工業的に利用できるオレフィン含有炭化水素混合物を使用する、請求項1から4までのいずれか1項に記載の方法。
- 第1のオレフィン供給原料としてラフィネートIIを使用する、請求項5に記載の方法。
- 第2のオレフィン供給原料が、ISO指数として測定して、0.5〜1.5の範囲のオレフィンの分枝度を有する、請求項1から6までのいずれか1項に記載の方法。
- 第2のオレフィン供給原料がダイマーゾル法、またはオクトール法によって得られる、請求項1から7までのいずれか1項に記載の方法。
- オレフィン供給原料の反応を工程b)において連続的に行う、請求項1から8までのいずれか1項に記載の方法。
- 工程b)からの反応生成物を、第1の部分流と第2の部分流とに分離し、第1の部分流を後処理に供して共二量化生成物を含むフラクションが得られ、かつ第2の部分流を工程a)に返送する、請求項1から9までのいずれか1項に記載の方法。
- CmオレフィンとCnオレフィンとのモル比が、工程b)に供給されるオレフィンに対して0.25:1〜4:1の範囲にある、請求項1から10までのいずれか1項に記載の方法。
- 工程b)において第1と第2のオレフィン供給原料を、層状ケイ酸塩ベースの、および/または立体網目状ケイ酸塩ベースのオレフィンオリゴマー化不均一触媒を用いて反応させる、請求項1から11までのいずれか1項に記載の方法。
- 工程b)で使用されるオリゴマー化触媒の層状ケイ酸塩、および/または立体網目状ケイ酸塩が、少なくとも50質量%の結晶割合を有する、請求項12に記載の方法。
- 工程b)で使用されるオリゴマー化触媒が、少なくとも0.5nmの平均細孔直径を有する少なくとも1の多孔性ケイ酸塩を含む、請求項12または13に記載の方法。
- 工程b)で使用されるオリゴマー化触媒が、少なくとも1種のゼオライトを含むか、または1種のゼオライトから成る、請求項12から14までのいずれか1項に記載の方法。
- アルコールの製造方法であって、
a)C mオレフィンから成る第1のオレフィン供給原料を調製し、かつISO指数として測定して0〜1.8の範囲のオレフィンの分枝度を有し、かつニッケル含有オリゴマー化触媒の存在下、ラフィネートIIの二量化によって得られる、C nオレフィンから成る第2のオレフィン供給原料を調製し[式中、nとmは相互に独立して、2〜12の互いに異なる2つの整数である]、
b)第1と第2のオレフィン供給原料を第1の反応帯域に供給し、かつ触媒の全質量に対してニッケル含分が最大で1質量%のオレフィンオリゴマー化不均一触媒を用いてオリゴマー化に供し、
c)第1の反応帯域の搬出物から、Cn+mオレフィン共二量体が濃縮された流れを分離し、
d)Cn+mオレフィン共二量体が濃縮された流れを第2の反応帯域に供給し、かつヒドロホルミル化触媒の存在下、一酸化炭素および水素との反応に供し、かつ
e)水素化する、
アルコールの製造方法。 - 7〜19の炭素原子を有するアルコールの製造方法であって、
a)C nオレフィンから成る第1のオレフィン供給原料を調製し、かつISO指数として測定して0〜1.8の範囲のオレフィンの分枝度を有し、かつニッケル含有オリゴマー化触媒の存在下、ラフィネートIIの二量化によって得られる、C 2nオレフィンから成る第2のオレフィン供給原料を調製し[式中、nは2〜6の整数である]、
b)第1と第2のオレフィン供給原料を第1の反応帯域に供給し、かつ触媒の全質量に対してニッケル含分が最大で1質量%のオレフィンオリゴマー化不均一触媒を用いてオリゴマー化に供し、
c)第1の反応帯域の搬出物から、C3nオレフィン共二量体が濃縮された流れを分離し、
d)C3nオレフィン共二量体が濃縮された流れを第2の反応帯域に供給し、かつヒドロホルミル化触媒の存在下、一酸化炭素および水素との反応に供し、かつ
e)水素化する、
7〜19の炭素原子を有するアルコールの製造方法。
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