JP5548258B2 - 副生物の形成を減少させた芳香族アルキル化方法 - Google Patents
副生物の形成を減少させた芳香族アルキル化方法 Download PDFInfo
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- 238000005804 alkylation reaction Methods 0.000 title description 59
- 125000003118 aryl group Chemical group 0.000 title description 57
- 239000006227 byproduct Substances 0.000 title description 27
- 230000015572 biosynthetic process Effects 0.000 title description 12
- 238000010555 transalkylation reaction Methods 0.000 claims description 153
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 147
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 118
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 68
- 239000010457 zeolite Substances 0.000 claims description 67
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 64
- 229910021536 Zeolite Inorganic materials 0.000 claims description 62
- 239000003054 catalyst Substances 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 46
- LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 claims description 43
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 claims description 43
- 238000004519 manufacturing process Methods 0.000 claims description 39
- 229930195733 hydrocarbon Natural products 0.000 claims description 33
- 150000002430 hydrocarbons Chemical class 0.000 claims description 32
- 230000008569 process Effects 0.000 claims description 32
- 239000004215 Carbon black (E152) Substances 0.000 claims description 30
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 20
- 238000000926 separation method Methods 0.000 claims description 13
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 claims description 11
- 239000000047 product Substances 0.000 description 47
- 230000029936 alkylation Effects 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 29
- 238000009835 boiling Methods 0.000 description 27
- 239000003795 chemical substances by application Substances 0.000 description 27
- 150000001491 aromatic compounds Chemical class 0.000 description 24
- 238000004821 distillation Methods 0.000 description 20
- 239000000758 substrate Substances 0.000 description 16
- 150000001336 alkenes Chemical class 0.000 description 11
- 238000011144 upstream manufacturing Methods 0.000 description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 10
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
- 239000002168 alkylating agent Substances 0.000 description 6
- 229940100198 alkylating agent Drugs 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Polymers 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- PEQXUXPSUIXZOB-UHFFFAOYSA-N 1,2-di(propan-2-yl)-3-propylbenzene Chemical compound C(C)(C)C=1C(=C(C=CC1)CCC)C(C)C PEQXUXPSUIXZOB-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- -1 acetylene hydrocarbons Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000004951 benzene Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012013 faujasite Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001997 phenyl group Polymers [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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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
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
- C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
- C07C6/126—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of more than one hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/067—C8H10 hydrocarbons
- C07C15/073—Ethylbenzene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/085—Isopropylbenzene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14833—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with metals or their inorganic compounds
- C07C7/1485—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with metals or their inorganic compounds oxides; hydroxides; salts
-
- 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
- C07C2521/04—Alumina
-
- 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
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- C07C2521/08—Silica
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Me2/nO:Al2O3:xSiO2:yH2O
(式中、Meはカチオンであり;nは該カチオンの原子価であり;xは5〜100値を有し;yは2〜10の値を有する)で表わすことのできる結晶質アルミノシリケートである。ゼオライトは、“D.W.Breck,Zeolite Molecular Sieves,John Wiley and Sons,ニューヨーク(1974)”などに詳細に説明されている。好適なゼオライトとしては、Y型ゼオライト、ベータ型ゼオライト、X型ゼオライト、モルデナイト、フォージャサイト、オメガ型ゼオライト、UZM−8、ZSM−5、PSH−3、MCM−22、MCM−36、MCM−49、およびMCM−56などがある。1種以上のタイプのゼオライトトランスアルキル化触媒を、異なるトランスアルキル化供給ストリームが送られる異なるトランスアルキル化反応ゾーンの触媒床に使用することができる。異なるゼオライトトランスアルキル化触媒の使用は、第1と第2のトランスアルキル化供給ストリーム(例えば、DIPBやTIPB等の異なるポリアルキル化芳香族化合物を高含量にて含む)を特定の反応ゾーン(あるいは反応環境)に適応させて副生物の形成を少なくするよう、本発明の1つの代表的な実施態様と関連している。
Claims (8)
- ジエチルベンゼン(DEB)とトリエチルベンゼン(TEB)を含む炭化水素供給ストリームをトランスアルキル化するための方法であって、
(a)ジエチルベンゼンを高含量にて含むトランスアルキル化供給ストリームと、トリエチルベンゼンを高含量にて含むトランスアルキル化供給ストリームとが得られるよう、該炭化水素供給ストリームを分けること;および
(b)ジエチルベンゼンを高含量にて含むトランスアルキル化供給ストリームと、トリエチルベンゼンを高含量にて含むトランスアルキル化供給ストリームとを異なるトランスアルキル化反応ゾーン中に通すこと;
を含む方法。 - 異なるトランスアルキル化反応ゾーンが共通の反応器内に存在する、請求項1に記載の方法。
- 異なるトランスアルキル化反応ゾーンが別個の反応器内に存在する、請求項1または2に記載の方法。
- 炭化水素供給ストリームが、エチルベンゼン製造プロセスにおける生成物分離セクションのプロセスストリームを含む、請求項1に記載の方法。
- ジイソプロピルベンゼン(DIPB)とトリイソプロピルベンゼン(TIPB)を含む炭化水素供給ストリームをトランスアルキル化するための方法であって、
(a)DIPBを高含量にて含むトランスアルキル化供給ストリームと、TIPBを高含量にて含むトランスアルキル化供給ストリームとが得られるよう、該炭化水素供給ストリームを分別すること;
(b)TIPBを高含量にて含むトランスアルキル化供給ストリームとベンゼンとを、第1と第2のゼオライト触媒床を含む第1のトランスアルキル化反応ゾーンに送ること;および
(c)DIPBを高含量にて含むトランスアルキル化供給ストリームを、第2のゼオライト触媒床を含む第2のトランスアルキル化反応ゾーンに送ること;
を含む方法。 - 第1のゼオライト触媒がY型ゼオライト、UZM−8ゼオライト、またはUZM−8とベータ型ゼオライトとの組み合わせ物を含み、第2のゼオライト触媒がベータ型ゼオライトを含む、請求項5に記載の方法。
- 炭化水素ストリームが、クメン製造プロセスにおける生成物分離セクションのプロセスストリームを含む、請求項5に記載の方法。
- ジイソプロピルベンゼン(DIPB)とトリイソプロピルベンゼン(TIPB)を含む炭化水素供給ストリームをトランスアルキル化するための方法であって、
(a)DIPBを高含量にて含むトランスアルキル化供給ストリームと、TIPBを高含量にて含むトランスアルキル化供給ストリームとが得られるよう、該炭化水素供給ストリームを分別すること;
(b)TIPBを高含量にて含むトランスアルキル化供給ストリームとベンゼンとを第1のトランスアルキル化反応器中にて反応させること;および
(c)DIPBを高含量にて含むトランスアルキル化供給ストリームとベンゼンとを第2のトランスアルキル化反応器中にて反応させること;
を含む方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/467,622 US9150469B2 (en) | 2009-05-18 | 2009-05-18 | Aromatic alkylation process with reduced byproduct formation |
US12/467,622 | 2009-05-18 | ||
PCT/US2010/032909 WO2010135062A2 (en) | 2009-05-18 | 2010-04-29 | Aromatic alkylation process with reduced byproduct formation |
Publications (2)
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JP2012527460A JP2012527460A (ja) | 2012-11-08 |
JP5548258B2 true JP5548258B2 (ja) | 2014-07-16 |
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JP2012511845A Active JP5548258B2 (ja) | 2009-05-18 | 2010-04-29 | 副生物の形成を減少させた芳香族アルキル化方法 |
Country Status (7)
Country | Link |
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US (1) | US9150469B2 (ja) |
JP (1) | JP5548258B2 (ja) |
KR (1) | KR101364357B1 (ja) |
CN (1) | CN102428058B (ja) |
SG (1) | SG175815A1 (ja) |
TW (1) | TWI465426B (ja) |
WO (1) | WO2010135062A2 (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
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SG190832A1 (en) * | 2010-11-17 | 2013-07-31 | China Petroleum & Chemical | A process for producing isopropyl benzene |
CN102304012B (zh) * | 2011-07-08 | 2013-12-18 | 中国石油化工股份有限公司 | 一种三异丙苯转位烷基化的工艺 |
US11578278B2 (en) | 2020-08-01 | 2023-02-14 | Honeywell International Inc. | Renewable transportation fuel process with thermal oxidation system |
US11780795B2 (en) | 2020-08-04 | 2023-10-10 | Honeywell International Inc. | Cumene-phenol complex with thermal oxidation system |
US11578020B2 (en) | 2020-08-04 | 2023-02-14 | Honeywell International Inc. | Naphtha complex with thermal oxidation system |
US11492306B2 (en) | 2020-09-30 | 2022-11-08 | Honeywell International Inc. | Alkylation process with thermal oxidation system |
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IT1127297B (it) * | 1979-12-19 | 1986-05-21 | Euteco Impianti Spa | Procedimento per la produzione di cumene |
IT1127296B (it) * | 1979-12-19 | 1986-05-21 | Euteco Impianti Spa | Procedimento perfezionato per la produzione di cumene |
JPS5740419A (en) * | 1980-08-22 | 1982-03-06 | Mitsui Petrochem Ind Ltd | Preparation of cumene |
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US7420098B2 (en) * | 2007-01-12 | 2008-09-02 | Uop Llc | Dual zone aromatic alkylation process |
WO2008097737A1 (en) * | 2007-02-09 | 2008-08-14 | Exxonmobil Chemical Patents Inc. A Corporation Of The State Of Delaware | Improved alkylaromatic production process |
US7683228B2 (en) * | 2007-02-12 | 2010-03-23 | Exxonmobil Chemical Patents Inc. | Production of high purity cumene from non-extracted feed and hydrocarbon composition useful therein |
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2009
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KR20120023743A (ko) | 2012-03-13 |
TW201105627A (en) | 2011-02-16 |
US20100292519A1 (en) | 2010-11-18 |
US9150469B2 (en) | 2015-10-06 |
KR101364357B1 (ko) | 2014-02-18 |
JP2012527460A (ja) | 2012-11-08 |
WO2010135062A3 (en) | 2011-03-24 |
SG175815A1 (en) | 2011-12-29 |
TWI465426B (zh) | 2014-12-21 |
WO2010135062A2 (en) | 2010-11-25 |
CN102428058B (zh) | 2015-12-16 |
CN102428058A (zh) | 2012-04-25 |
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