JP6374994B2 - キシレンの製造方法 - Google Patents
キシレンの製造方法 Download PDFInfo
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- JP6374994B2 JP6374994B2 JP2016575967A JP2016575967A JP6374994B2 JP 6374994 B2 JP6374994 B2 JP 6374994B2 JP 2016575967 A JP2016575967 A JP 2016575967A JP 2016575967 A JP2016575967 A JP 2016575967A JP 6374994 B2 JP6374994 B2 JP 6374994B2
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- xylene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
- C07C2/864—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an alcohol
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
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- 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
- C07C15/06—Toluene
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- 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
- C07C15/08—Xylenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/08—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
- C07C4/12—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2729—Changing the branching point of an open chain or the point of substitution on a ring
- C07C5/2732—Catalytic processes
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
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- 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
- C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
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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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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Description
モリニエ、マイケル;アンドリュース、ジェフリー エル;ベンダー、ティモシー ピー;ティンガー、ロバート ジー;スタンリー、デニス ジェイ;およびワグナー、ジョージ ジェイ
関連出願の相互参照
本出願は、2014年6月30日に出願された米国特許仮出願第62/018,726号および2014年8月6日に出願された欧州特許出願第14180052.4号の優先権および利益を主張し、これらすべての内容は参照によってその全体が組み込まれる。関連する出願は、2014年6月30日に出願された米国特許仮出願第62/018,724号(整理番号:2014EM155)および に出願された米国特許出願第 号(整理番号:2015EM128)である。
技術分野
Claims (10)
- パラキシレンを製造する方法であって、
(a1)C6+芳香族炭化水素を含む供給原料流を、少なくともトルエン含有流、C8芳香族炭化水素含有流およびC9+芳香族炭化水素含有流に分離する工程、
(b1)前記トルエン含有流の少なくとも一部を、トルエンをキシレンに転化してメチル化された流出物流を製造するのに有効な条件の下でメチル化剤と接触させる工程、
(c1)前記C8芳香族炭化水素含有流および前記メチル化された流出物流からパラキシレンを回収して、少なくとも1つのパラキシレンに乏しい流を製造する工程、
(d1)前記少なくとも1つのパラキシレンに乏しい流の少なくとも一部を、前記パラキシレンに乏しい流中のキシレンを異性化して異性化された流を製造するのに有効な液相条件の下でキシレン異性化触媒と接触させる工程、
(e1)前記異性化された流の少なくとも一部を(c1)にリサイクルする工程、
(f1)前記C9+ 芳香族炭化水素含有流の少なくとも一部を、C9+芳香族炭化水素をC8−芳香族炭化水素に転化してトランスアルキル化された流を製造するのに有効な条件の下でトランスアルキル化触媒と接触させる工程、および
(g1)前記トランスアルキル化された流の少なくとも一部を(b1)にリサイクルする工程
を含む、方法。 - (a1)に記載の供給原料流が、改質油流からC5−炭化水素を除くことによって製造されたC6+芳香族および脂肪族炭化水素の混合物を含む、請求項1に記載の方法。
- 分離工程(a1)がベンゼン含有流も製造する、請求項1または請求項2に記載の方法。
- 前記ベンゼン含有流の一部が、接触工程(f1)に供給されてメチル基と環との比が最適化される、請求項3に記載の方法。
- 前記ベンゼン含有流の少なくとも一部が接触工程(b1)に供給される、請求項3に記載の方法。
- 接触工程(b1)が、120℃の温度および60トール(8kPa)の2,2−ジメチルブタンの圧力で測定されたときに2,2−ジメチルブタンについての約0.1〜15秒−1の拡散パラメーターを有する多孔性結晶質物質を含む触媒の存在下に実施される、請求項1に記載の方法。
- (h1)前記少なくとも1つのパラキシレンに乏しい流の少なくとも一部を、前記パラキシレンに乏しい流中のキシレンを異性化しかつエチルベンゼンを脱アルキル化しまたは異性化して異性化されたかつエチルベンゼンに乏しい流を製造するのに有効な気相条件の下でキシレン異性化触媒と接触させる工程、および
(i1)前記異性化されたかつエチルベンゼンに乏しい流の少なくとも一部を(c1)にリサイクルする工程
をさらに含む、請求項1に記載の方法。 - 前記気相条件が、前記パラキシレンに乏しい流中のエチルベンゼンを脱アルキル化して副生成トルエン流を製造するのに有効であり、前記副生成トルエン流を接触工程(b1)に供給することをさらに含む、請求項7に記載の方法。
- 前記トランスアルキル化された流中のC 7−芳香族炭化水素の少なくとも一部が、接触工程(b1)および/または接触工程(f1)にリサイクルされる、請求項1に記載の方法。
- (k1)前記メチル化された流出物流から未転化のトルエンを回収する工程、および
(l1)前記未転化のトルエンを接触工程(b1)に供給する工程
をさらに含む、請求項1に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201462018726P | 2014-06-30 | 2014-06-30 | |
US62/018,726 | 2014-06-30 | ||
EP14180052.4 | 2014-08-06 | ||
EP14180052 | 2014-08-06 | ||
PCT/US2015/035103 WO2016003613A2 (en) | 2014-06-30 | 2015-06-10 | Process for the production of xylenes |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2017521413A JP2017521413A (ja) | 2017-08-03 |
JP6374994B2 true JP6374994B2 (ja) | 2018-08-15 |
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ID=51265624
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016575967A Expired - Fee Related JP6374994B2 (ja) | 2014-06-30 | 2015-06-10 | キシレンの製造方法 |
Country Status (3)
Country | Link |
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JP (1) | JP6374994B2 (ja) |
KR (1) | KR101917491B1 (ja) |
CN (1) | CN106488897B (ja) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
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US10577293B2 (en) * | 2017-04-19 | 2020-03-03 | Uop Llc | Process and apparatus for improved para-xylene yield in an aromatic complex |
FR3068966B1 (fr) * | 2017-07-12 | 2019-06-28 | IFP Energies Nouvelles | Nouveau schema de production de benzene a partir de reformat sans colonne de toluene |
FR3072885B1 (fr) * | 2017-10-27 | 2019-11-15 | IFP Energies Nouvelles | Nouveau systeme de distribution par panneaux meridiens pour un procede de separation en lit mobile simule utilisant n-colonnes en serie |
US11401222B2 (en) * | 2017-12-05 | 2022-08-02 | Ineos Us Chemicals Company | Method for recovery of paraxylene with reduced crystallization load |
WO2019112769A1 (en) * | 2017-12-05 | 2019-06-13 | Exxonmobil Chemical Patents Inc. | Xylene production processes and systems |
FR3090633B1 (fr) * | 2018-12-19 | 2021-01-01 | Ifp Energies Now | Couplage unité d’extraction d’aromatiques substitués en méthyles et unité d'hydrogénolyse d'alkyle-aromatiques |
US11767280B2 (en) | 2019-02-04 | 2023-09-26 | China Petroleum & Chemical Corporation | Process for making phenol and xylenes |
US11643375B2 (en) * | 2019-03-28 | 2023-05-09 | Exxonmobil Chemical Patents Inc. | Processes for converting benzene and/or toluene via methylation |
JP7262612B2 (ja) * | 2019-03-29 | 2023-04-21 | エクソンモービル ケミカル パテンツ インコーポレイテッド | 新規ゼオライト、その製造方法、及び芳香族炭化水素の変換におけるその使用 |
US20200354293A1 (en) | 2019-05-10 | 2020-11-12 | Uop Llc | Process and apparatus for dual feed para-xylene separation |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
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US4053388A (en) * | 1976-12-06 | 1977-10-11 | Moore-Mccormack Energy, Inc. | Process for preparing aromatics from naphtha |
US7148391B1 (en) * | 2002-11-14 | 2006-12-12 | Exxonmobil Chemical Patents Inc. | Heavy aromatics processing |
CN1216020C (zh) * | 2002-12-11 | 2005-08-24 | 中国石油化工股份有限公司 | 苯与碳九芳烃烷基转移方法 |
US7371912B2 (en) * | 2005-06-15 | 2008-05-13 | Uop Llc | Process for making xylene isomer using a deheptanizer with a side draw recycle |
US7405335B1 (en) * | 2005-06-30 | 2008-07-29 | Uop Llc | Integrated process for producing xylenes and high purity benzene |
SG189261A1 (en) * | 2010-10-29 | 2013-05-31 | Exxonmobil Chem Patents Inc | Process for the production of paraxylene |
WO2012078373A2 (en) * | 2010-12-10 | 2012-06-14 | Exxonmobil Chemical Patents Inc. | Method and apparatus for obtaining aromatics from diverse feedstock |
US8937205B2 (en) * | 2012-05-07 | 2015-01-20 | Exxonmobil Chemical Patents Inc. | Process for the production of xylenes |
CN104718180A (zh) * | 2012-10-09 | 2015-06-17 | 埃克森美孚化学专利公司 | 对二甲苯制造中的吹扫料流 |
BR112015008035A2 (pt) * | 2012-10-10 | 2017-07-04 | Gtc Technology Us Llc | processos e sistemas para obtenção de aromáticos a parti de craqueamento catalítico de hidrocarbonetos |
-
2015
- 2015-06-10 KR KR1020167036976A patent/KR101917491B1/ko active IP Right Grant
- 2015-06-10 JP JP2016575967A patent/JP6374994B2/ja not_active Expired - Fee Related
- 2015-06-10 CN CN201580031827.1A patent/CN106488897B/zh active Active
Also Published As
Publication number | Publication date |
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KR20170013947A (ko) | 2017-02-07 |
JP2017521413A (ja) | 2017-08-03 |
CN106488897A (zh) | 2017-03-08 |
CN106488897B (zh) | 2020-04-24 |
KR101917491B1 (ko) | 2018-11-09 |
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