JP4667365B2 - アルキルベンゼンの製造プロセス - Google Patents
アルキルベンゼンの製造プロセス Download PDFInfo
- Publication number
- JP4667365B2 JP4667365B2 JP2006503850A JP2006503850A JP4667365B2 JP 4667365 B2 JP4667365 B2 JP 4667365B2 JP 2006503850 A JP2006503850 A JP 2006503850A JP 2006503850 A JP2006503850 A JP 2006503850A JP 4667365 B2 JP4667365 B2 JP 4667365B2
- Authority
- JP
- Japan
- Prior art keywords
- stream
- benzene
- effluent
- alkylation
- alkylbenzene
- 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
Links
- 150000004996 alkyl benzenes Chemical class 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 159
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical group CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 68
- 238000005804 alkylation reaction Methods 0.000 claims description 41
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 40
- 239000005977 Ethylene Substances 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 28
- 239000010457 zeolite Substances 0.000 claims description 27
- 229910021536 Zeolite Inorganic materials 0.000 claims description 26
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 26
- 230000029936 alkylation Effects 0.000 claims description 24
- 150000001336 alkenes Chemical class 0.000 claims description 23
- 239000006096 absorbing agent Substances 0.000 claims description 21
- 238000004821 distillation Methods 0.000 claims description 20
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 18
- 239000008161 low-grade oil Substances 0.000 claims description 15
- 239000003921 oil Substances 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 13
- 238000010555 transalkylation reaction Methods 0.000 claims description 13
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910052680 mordenite Inorganic materials 0.000 claims description 4
- 239000011959 amorphous silica alumina Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 description 17
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 239000007789 gas Substances 0.000 description 9
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 5
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- -1 aluminum halides Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- FEWANSQOXSIFOK-UHFFFAOYSA-N 1,2,3,4-tetraethylbenzene Chemical compound CCC1=CC=C(CC)C(CC)=C1CC FEWANSQOXSIFOK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 description 1
- BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical compound C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
Images
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
- C07C2/54—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
- 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
- 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
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/12—Silica and alumina
-
- 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
- C07C2529/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
-
- 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
- C07C2529/60—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the type L
-
- 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
-
- 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
- Y02P20/10—Process efficiency
-
- 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
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)
Description
(b)塔頂流出物流を、ベンゼンを含有する液体部分と未変換のオレフィンを含有する蒸気部分とに分離し、
(c)少なくとも一部のベンゼンとポリアルキルベンゼンとをアルキルベンゼンに変換するトランスアルキル化反応条件下で、トランスアルキル化区域に塔頂流出物流の液体部分とポリアルキルベンゼン流とを導入し、
(d)塔頂流出物流の蒸気部分中の未変換のオレフィンの大部分を、ベンゼンとアルキルベンゼンとを含有する芳香族化合物流中に吸収し、
(e)前記吸収したオレフィンと前記芳香族化合物流の少なくとも一部のベンゼンとをアルキルベンゼンに変換する第二のアルキル化反応条件下で、第二のアルキル化触媒を含有する第二のアルキル化反応区域に、前記吸収したオレフィンを含有する前記芳香族化合物流を導入する、ステップを含む。プロセスは、エチルベンゼンを生成する目的に特に適しており、従来のシステムよりも必要な触媒がはるかに少なく、それと同時により高い総エチレン変換率を達成する。
蓄積装置ドラム113からの凝縮されていない蒸気は、熱交換器116中で加熱され、エチレン、ベンゼン、およびエタン、メタン、水素などの不活性ガスを含有する蒸気流は、ライン117を介して、芳香族化合物の回収のための排気吸収器130へと送られる。
Claims (20)
- アルキルベンゼンの製造方法であって、
a)アルキルベンゼンを含有する流出物と第一のアルキル化塔頂流出物流とを生成する第一のアルキル化反応条件下で、第一のアルキル化触媒存在下の第一のアルキル化反応区域にベンゼンとオレフィン供給物とを導入し、
b)第一のアルキル化塔頂流出物流を、ベンゼンを含有する液体部分と未変換のオレフィンを含有する蒸気部分とに分離し、
c)第一のアルキル化塔頂流出物流の蒸気部分中の未変換のオレフィンの一部を、吸収区域中でベンゼンとアルキルベンゼンとを含有する芳香族化合物低品位油流中に吸収して、オレフィンを含有する高品位油流を生成し、
d)芳香族化合物低品位油流を生成する第二のアルキル化反応条件下で、第二のアルキル化触媒を含有する第二のアルキル化反応区域に前記高品位油流を導入し、芳香族化合物低品位油流の少なくとも一部を前記吸収区域へ循環して戻す、
各ステップを含むことを特徴とするアルキルベンゼンの製造方法。 - 少なくとも一部のベンゼンとポリアルキルベンゼンとをアルキルベンゼンに変換するトランスアルキル化反応条件下で、トランスアルキル化触媒存在下のトランスアルキル化区域に、第一のアルキル化塔頂流出物流の液体部分とポリアルキルベンゼン流とを導入するステップをさらに含むことを特徴とする請求項1記載の方法。
- 前記オレフィンはエチレンであり、前記アルキルベンゼンはエチルベンゼンであり、前記ポリアルキルベンゼンはポリエチルベンゼンであることを特徴とする請求項2に記載の方法。
- 前記第一のアルキル化反応条件は、2067kPa(300psig)から3790kPa(550psig)の圧力、185℃から240℃の温度、および2.0から3.5の範囲のフェニル:エチル比を含むことを特徴とする請求項3記載の方法。
- 前記第一のアルキル化反応区域は、触媒蒸留装置からなることを特徴とする請求項4に記載の方法。
- 前記吸収区域は、未反応ガスとベンゼンとを含有する吸収器塔頂流出物蒸気流を生成し、この吸収器塔頂流出物蒸気流は、洗浄器へと移され、そこで吸収器塔頂流出物蒸気流は、ポリエチレンベンゼンを含有する流れと接触し、洗浄器は、トランスアルキル化反応区域へと循環されるポリエチルベンゼンを含有する洗浄器底部流出物を生成することを特徴とする請求項3に記載の方法。
- 前記第一のアルキル化反応区域からのエチルベンゼン含有流出物は、ベンゼンを含有する第一の蒸留塔頂流出物流と、エチルベンゼンを含有する第一の蒸留底流とを生成する第一の蒸留装置へと移され、この第一の蒸留塔頂流出物流の一部は、第二のアルキル化反応区域からの芳香族化合物低品位油流へと循環されることを特徴とする請求項6に記載の方法。
- 前記第一の蒸留底流は、エチルベンゼンを含有する第二の蒸留塔頂流出物流と、ポリエチルベンゼンを含有する第二の蒸留底流とを生成する第二の蒸留装置へと移されることを特徴とする請求項7に記載の方法。
- 前記第二の蒸留底流は、ポリエチルベンゼンを含有する第三の蒸留塔頂流出物流を生成する第三の蒸留装置へと移され、この第三の蒸留塔頂流出物は、洗浄器へと循環されて戻されることを特徴とする請求項8に記載の方法。
- 前記吸収区域は充填カラムからなることを特徴とする請求項1に記載の方法。
- 前記吸収区域は精留用の棚板が設置されたトレイカラムからなることを特徴とする請求項1に記載の方法。
- 前記第一のアルキル化触媒は、ゼオライトX、ゼオライトY、ゼオライトL、TMAオフレタイト、モルデナイト、アモルファスシリカ−アルミナ、ゼオライトBEA、ゼオライトMWW、およびMFI型ゼオライト触媒から成る群より選択される材料からなることを特徴とする請求項3に記載の方法。
- 前記第二のアルキル化触媒は、ゼオライトX、ゼオライトY、ゼオライトL、TMAオフレタイト、モルデナイト、アモルファスシリカ−アルミナ、ゼオライトBEA、ゼオライトMWW、およびMFI型ゼオライト触媒からなる群より選択される材料からなることを特徴とする請求項3に記載の方法。
- (a)オレフィンでベンゼンをアルキル化しかつアルキルベンゼンとベンゼンとを含有する流出物と塔頂流出物流とを生成する第一のアルキル化装置と、
(b)第一のアルキル化装置からの塔頂流出物流を、蒸気流と液体流とに分離する凝縮装置と、
(c)第一のアルキル化装置の塔頂流出物からの液体流を、ポリアルキルベンゼンを含有する流れと接触させて、アルキルベンゼンとベンゼンとを含有するトランスアルキル化装置流出物を生成するトランスアルキル化装置と、
(d)第一のアルキル化装置の塔頂流出物からの蒸気流を、ベンゼンとアルキルベンゼンとを含有する低品位油流と接触させて、ベンゼンと、アルキルベンゼンと、未変換のオレフィンとを含有する高品位油流を生成する吸収器と、
(e)前記未変換のオレフィンと、高品位油流中の少なくとも一部のベンゼンとを変換して低品位油流を生成し、この低品位油流の少なくとも一部を前記吸収器へ循環して戻す第二のアルキル化装置と、
を備えることを特徴とするアルキルベンゼン生成のための装置。 - 前記第一のアルキル化装置は、触媒蒸留装置からなることを特徴とする請求項14に記載の装置。
- 前記吸収器は充填カラムからなることを特徴とする請求項14に記載の装置。
- 前記吸収器は精留用の棚板が設置されたトレイカラムからなることを特徴とする請求項14に記載の装置。
- 前記吸収器からの蒸気塔頂流出物流を、ポリアルキルベンゼンを含有する流れと接触させる洗浄器をさらに備えることを特徴とする請求項14に記載の装置。
- ベンゼンとアルキルベンゼンとを、第一のアルキル化装置の流出物から分離する蒸留装置をさらに備えることを特徴とする請求項14に記載の装置。
- 前記第二のアルキル化装置からの低品位油流と前記吸収器からの高品位油流との間で熱を伝達させるための熱伝達装置をさらに備えることを特徴とする請求項14に記載の装置。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/372,449 US7074978B2 (en) | 2003-02-25 | 2003-02-25 | Process for the production of alkylbenzene |
PCT/US2004/005540 WO2004076387A2 (en) | 2003-02-25 | 2004-02-24 | Process for the production of alkylbenzene |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006518762A JP2006518762A (ja) | 2006-08-17 |
JP4667365B2 true JP4667365B2 (ja) | 2011-04-13 |
Family
ID=32868528
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006503850A Expired - Fee Related JP4667365B2 (ja) | 2003-02-25 | 2004-02-24 | アルキルベンゼンの製造プロセス |
Country Status (12)
Country | Link |
---|---|
US (2) | US7074978B2 (ja) |
EP (1) | EP1606234B1 (ja) |
JP (1) | JP4667365B2 (ja) |
KR (1) | KR101016880B1 (ja) |
CN (1) | CN100465141C (ja) |
AU (2) | AU2004215343B2 (ja) |
BR (1) | BRPI0407706B1 (ja) |
CA (1) | CA2516648C (ja) |
MX (1) | MXPA05008417A (ja) |
RU (1) | RU2298541C2 (ja) |
WO (1) | WO2004076387A2 (ja) |
ZA (1) | ZA200506798B (ja) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7074978B2 (en) * | 2003-02-25 | 2006-07-11 | Abb Lummus Global Inc. | Process for the production of alkylbenzene |
US7071369B2 (en) * | 2003-06-10 | 2006-07-04 | Abb Lummus Global Inc. | Process for the production of alkylbenzene with ethane stripping |
US7259282B2 (en) | 2003-09-08 | 2007-08-21 | Abb Lummus Global Inc. | Process for production of ethylbenzene from dilute ethylene streams |
US6977319B2 (en) * | 2004-03-12 | 2005-12-20 | Chevron Oronite Company Llc | Alkylated aromatic compositions, zeolite catalyst compositions and processes for making the same |
US7622622B1 (en) | 2004-06-21 | 2009-11-24 | Uop Llc | Process for the high yield production of monoalkylaromatics |
BRPI0607696B1 (pt) * | 2005-02-28 | 2015-06-30 | Exxonmobil Res & Eng Co | Método para produzir um produto de faixa de ebulição da gasolina |
US7476774B2 (en) * | 2005-02-28 | 2009-01-13 | Exxonmobil Research And Engineering Company | Liquid phase aromatics alkylation process |
US7632974B2 (en) * | 2006-07-19 | 2009-12-15 | Lammus Technology Inc. | Alkylation process for increased conversion and reduced catalyst use |
US8278494B2 (en) * | 2007-06-27 | 2012-10-02 | H R D Corporation | Method of making linear alkylbenzenes |
US8304584B2 (en) | 2007-06-27 | 2012-11-06 | H R D Corporation | Method of making alkylene glycols |
US7491856B2 (en) | 2007-06-27 | 2009-02-17 | H R D Corporation | Method of making alkylene glycols |
US8101810B2 (en) * | 2008-08-20 | 2012-01-24 | Catalytic Distillation Technologies | Reformate benzene reduction via alkylation |
US20100204964A1 (en) * | 2009-02-09 | 2010-08-12 | Utah State University | Lidar-assisted multi-image matching for 3-d model and sensor pose refinement |
WO2011046547A1 (en) * | 2009-10-14 | 2011-04-21 | Uop Llc | Process for the high yield production of monoalkylaromatics |
US8414851B2 (en) | 2010-06-11 | 2013-04-09 | Uop Llc | Apparatus for the reduction of gasoline benzene content by alkylation with dilute ethylene |
US8895793B2 (en) | 2010-06-11 | 2014-11-25 | Uop Llc | Process for the reduction of gasoline benzene content by alkylation with dilute ethylene |
US20120031096A1 (en) * | 2010-08-09 | 2012-02-09 | Uop Llc | Low Grade Heat Recovery from Process Streams for Power Generation |
US20120289677A1 (en) * | 2011-05-11 | 2012-11-15 | Uop, Llc | Process for alkylating benzene |
US8889937B2 (en) | 2011-06-09 | 2014-11-18 | Uop Llc | Process for producing one or more alkylated aromatics |
RU2484898C2 (ru) * | 2011-07-07 | 2013-06-20 | Федеральное государственное бюджетное учреждение науки Ордена Трудового Красного Знамени Институт нефтехимического синтеза им. А.В. Топчиева Российской академии наук (ИНХС РАН) | Способ повышения времени стабильной работы катализатора в реакции гидроалкилирования бензола ацетоном с получением кумола и способ получения кумола гидроалкилированием бензола ацетоном |
CN102503760A (zh) * | 2011-10-11 | 2012-06-20 | 中国石油化工股份有限公司 | 一种延长乙苯工艺中烷基化催化剂再生周期的装置和方法 |
CN103664484B (zh) * | 2012-09-05 | 2016-04-06 | 中国石油化工股份有限公司 | 苯与乙烯气相烃化制乙苯的方法 |
RU2514948C1 (ru) * | 2013-05-16 | 2014-05-10 | ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ БЮДЖЕТНОЕ УЧРЕЖДЕНИЕ НАУКИ ИНСТИТУТ ОРГАНИЧЕСКОЙ ХИМИИ им. Н.Д. ЗЕЛИНСКОГО РОССИЙСКОЙ АКАДЕМИИ НАУК (ИОХ РАН) | Катализатор для получения этилбензола из бензола и этана и способ получения этилбензола с его использованием |
CN104860790B (zh) * | 2015-05-26 | 2016-08-24 | 天津大学 | 利用炼厂干气变压吸附回收的乙烯制乙苯的装置及方法 |
CN105622308A (zh) * | 2016-01-06 | 2016-06-01 | 江苏常青树新材料科技有限公司 | 一步法同时合成甲乙苯和二乙苯的方法 |
US11034632B2 (en) | 2016-09-15 | 2021-06-15 | Lummus Technology Llc | Ethane recovery process and alkylation process with ethane recovery |
CN107827692B (zh) * | 2017-04-28 | 2021-06-29 | 常州瑞华化工工程技术股份有限公司 | 一种用高浓度乙烯气生产乙苯的方法 |
KR102397644B1 (ko) * | 2017-06-16 | 2022-05-13 | 에스케이이노베이션 주식회사 | 유동층접촉분해 오프-가스와 벤젠의 알킬화 생성물로부터 에틸벤젠을 회수하는 방법 |
CN110093182A (zh) * | 2019-04-18 | 2019-08-06 | 江苏中能化学科技股份有限公司 | 一种烷基苯类导热油及其制备方法 |
CN114717022B (zh) * | 2021-01-04 | 2023-07-14 | 中国石油化工股份有限公司 | 一种环保型芳烃橡胶填充油及其制备方法和装置 |
CN115353439A (zh) * | 2022-07-21 | 2022-11-18 | 中石化广州工程有限公司 | 含乙烯干气液相法生产乙苯的工艺及装置 |
CN115304445A (zh) * | 2022-07-21 | 2022-11-08 | 中石化广州工程有限公司 | 含乙烯干气液相法制乙苯的工艺及装置 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03178935A (ja) * | 1989-11-28 | 1991-08-02 | Inst Fr Petrole | 天然ガスからのアルキル芳香族炭化水素の製造方法 |
WO1995032166A1 (en) * | 1994-05-23 | 1995-11-30 | Chemical Research & Licensing Company | Alkylation of organic aromatic compounds |
JP2003503378A (ja) * | 1999-06-29 | 2003-01-28 | セラニーズ・インターナショナル・コーポレーション | エチレン回収システム |
Family Cites Families (61)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3077491A (en) * | 1959-10-26 | 1963-02-12 | Fmc Corp | Preparation of triarylphosphates |
US3205277A (en) * | 1962-12-21 | 1965-09-07 | Universal Oil Prod Co | Alkylation-transalkylation process |
US3200164A (en) * | 1964-09-08 | 1965-08-10 | Universal Oil Prod Co | Alkylation-transalkylation process |
US3428701A (en) * | 1968-03-01 | 1969-02-18 | Universal Oil Prod Co | Alkylation-transalkylation process |
US3843739A (en) * | 1971-04-09 | 1974-10-22 | Gulf Research Development Co | Process for transalkylating diethyl benzene |
US4008290A (en) * | 1975-03-10 | 1977-02-15 | Uop Inc. | Cumene production |
DE2511674C3 (de) * | 1975-03-18 | 1978-12-21 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Herstellung von Äthylbenzol durch dehydrierende Aromatisierung |
US4316997A (en) * | 1976-02-23 | 1982-02-23 | Varen Technology | Alkylation process and apparatus useful therein |
US4083886A (en) * | 1976-03-29 | 1978-04-11 | Uop Inc. | Transalkylation of alkylaromatic hydrocarbons |
US4051191A (en) * | 1977-01-03 | 1977-09-27 | Uop Inc. | Solid phosphoric acid catalyzed alkylation of aromatic hydrocarbons |
US4169111A (en) * | 1978-02-02 | 1979-09-25 | Union Oil Company Of California | Manufacture of ethylbenzene |
US4215011A (en) * | 1979-02-21 | 1980-07-29 | Chemical Research And Licensing Company | Catalyst system for separating isobutene from C4 streams |
US4242530A (en) * | 1978-07-27 | 1980-12-30 | Chemical Research & Licensing Company | Process for separating isobutene from C4 streams |
US4302356A (en) * | 1978-07-27 | 1981-11-24 | Chemical Research & Licensing Co. | Process for separating isobutene from C4 streams |
US4232177A (en) * | 1979-02-21 | 1980-11-04 | Chemical Research & Licensing Company | Catalytic distillation process |
US4250052A (en) * | 1978-09-08 | 1981-02-10 | Chemical Research & Licensing Company | Catalyst structure and a process for its preparation |
US4469908A (en) * | 1978-12-14 | 1984-09-04 | Mobil Oil Corporation | Alkylation of aromatic hydrocarbons |
US4307254A (en) * | 1979-02-21 | 1981-12-22 | Chemical Research & Licensing Company | Catalytic distillation process |
US4423254A (en) * | 1980-03-14 | 1983-12-27 | Pcuk Produits Chimiques Ugine Kuhlmann | Superacid catalyzed preparation of resorcinol from meta-isopropylphenol |
US4459426A (en) * | 1980-04-25 | 1984-07-10 | Union Oil Company Of California | Liquid-phase alkylation and transalkylation process |
US4371714A (en) * | 1980-12-30 | 1983-02-01 | Mobil Oil Corporation | Preparation of 4-alkylanisoles and phenols |
US4443559A (en) * | 1981-09-30 | 1984-04-17 | Chemical Research & Licensing Company | Catalytic distillation structure |
US4570027A (en) * | 1984-04-27 | 1986-02-11 | Exxon Research And Engineering Co. | Alkylation of aromatic molecules using a silica-alumina catalyst derived from zeolite |
US4540831A (en) * | 1984-05-17 | 1985-09-10 | Uop Inc. | Mixed-phase hydrocarbon conversion process employing total overhead condenser |
US4587370A (en) * | 1985-06-05 | 1986-05-06 | Uop Inc. | Aromatic hydrocarbon alkylation process product recovery method |
US4735929A (en) * | 1985-09-03 | 1988-04-05 | Uop Inc. | Catalytic composition for the isomerization of paraffinic hydrocarbons |
US4695665A (en) * | 1986-07-02 | 1987-09-22 | Uop Inc. | Process for alkylation of hydrocarbons |
US4857666A (en) * | 1987-09-11 | 1989-08-15 | Uop | Alkylation/transalkylation process |
US4849569A (en) * | 1987-11-16 | 1989-07-18 | Chemical Research & Licensing Company | Alkylation of organic aromatic compounds |
US4891458A (en) * | 1987-12-17 | 1990-01-02 | Innes Robert A | Liquid phase alkylation or transalkylation process using zeolite beta |
US5003119A (en) * | 1988-05-09 | 1991-03-26 | Lummus Crest, Inc. | Manufacture of alkylbenzenes |
EP0424393B1 (en) * | 1988-05-09 | 1995-08-09 | Abb Lummus Global Inc. | Manufacture of alkylbenzenes |
US4922053A (en) * | 1989-05-24 | 1990-05-01 | Fina Technology, Inc. | Process for ethylbenzene production |
US5030786A (en) * | 1989-06-23 | 1991-07-09 | Fina Technology, Inc. | Liquid phase aromatic conversion process |
US5334795A (en) * | 1990-06-28 | 1994-08-02 | Mobil Oil Corp. | Production of ethylbenzene |
IT1247108B (it) * | 1991-02-28 | 1994-12-12 | Snam Progetti | Procedimento integrato per la produzione di iso-butene ed eteri alchil-ter-butilici. |
CH686357A5 (fr) * | 1991-05-06 | 1996-03-15 | Bobst Sa | Dispositif de lecture d'une marque imprimée sur un élément en plaque ou en bande. |
US5118894A (en) * | 1991-07-18 | 1992-06-02 | Mobil Oil Corporation | Production of ethylbenzene |
US5177285A (en) * | 1991-12-23 | 1993-01-05 | Uop | Process for wet aromatic alkylation and dry aromatic transalkylation |
US5336821A (en) * | 1993-05-06 | 1994-08-09 | Uop | Alkylation process with reactor effluent heat recovery |
CA2172207A1 (en) | 1995-03-21 | 1996-09-22 | Mark Edward Kuchenmeister | Transalkylation of polyalkylaromatic hydrocarbons |
US5602290A (en) * | 1995-05-30 | 1997-02-11 | Raytheon Engineers & Constructors, Inc. | Pretreatment of dilute ethylene feedstocks for ethylbenzene production |
US5847251A (en) * | 1996-02-12 | 1998-12-08 | Catalytic Distillation Technologies | Multibed transalkylator and process |
US5856607A (en) * | 1996-05-03 | 1999-01-05 | Amoco Corporation | Process for production of ethylbenzene frome dilute ethylene streams |
US5723710A (en) * | 1996-07-12 | 1998-03-03 | Uop | Zeolite beta and its use in aromatic alkylation |
US6060632A (en) * | 1996-07-19 | 2000-05-09 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing ethylbenzene |
US5998684A (en) * | 1996-12-19 | 1999-12-07 | Uop Llc | Recovery process for wet aromatic alkylation and dry aromatic transalkylation |
US6096935A (en) * | 1998-07-28 | 2000-08-01 | Uop Llc | Production of alkyl aromatics by passing transalkylation effluent to alkylation zone |
US20020182124A1 (en) * | 1997-10-14 | 2002-12-05 | William M. Woodard | Olefin production process |
US5902917A (en) * | 1997-11-26 | 1999-05-11 | Mobil Oil Corporation | Alkylaromatics production |
US6252126B1 (en) * | 1998-06-19 | 2001-06-26 | David Netzer | Method for producing ethylbenzene |
US5977423A (en) * | 1998-06-19 | 1999-11-02 | Netzer; David | Mixed phase ethylation process for producing ethylbenzene |
US6281399B1 (en) * | 1998-07-28 | 2001-08-28 | Uop Llc | Production of isopropyl aromatics by passing portions of transalkylation effluent to a multi-bed alkylation zone |
CN1170795C (zh) * | 1999-04-09 | 2004-10-13 | 中国石油天然气集团公司 | 一种稀乙烯和/或丙烯制乙苯和/或异丙苯方法 |
CN1237036C (zh) * | 2000-02-02 | 2006-01-18 | 陶氏环球技术公司 | 用于生产链烯基取代的芳香族化合物的综合方法 |
US6486371B1 (en) * | 2000-11-28 | 2002-11-26 | Fina Technology, Inc. | Multistage reaction system with interstage sparger systems |
US6376729B1 (en) * | 2000-12-04 | 2002-04-23 | Fina Technology, Inc. | Multi-phase alkylation process |
US6417420B1 (en) * | 2001-02-26 | 2002-07-09 | Uop Llc | Alkylaromatic process with removal of aromatic byproducts using efficient distillation |
US6995295B2 (en) * | 2002-09-23 | 2006-02-07 | Exxonmobil Chemical Patents Inc. | Alkylaromatics production |
US7074978B2 (en) * | 2003-02-25 | 2006-07-11 | Abb Lummus Global Inc. | Process for the production of alkylbenzene |
US7071369B2 (en) * | 2003-06-10 | 2006-07-04 | Abb Lummus Global Inc. | Process for the production of alkylbenzene with ethane stripping |
-
2003
- 2003-02-25 US US10/372,449 patent/US7074978B2/en active Active
-
2004
- 2004-02-24 AU AU2004215343A patent/AU2004215343B2/en not_active Ceased
- 2004-02-24 BR BRPI0407706-7A patent/BRPI0407706B1/pt not_active IP Right Cessation
- 2004-02-24 CA CA2516648A patent/CA2516648C/en not_active Expired - Fee Related
- 2004-02-24 KR KR1020057015697A patent/KR101016880B1/ko active IP Right Grant
- 2004-02-24 CN CNB2004800051421A patent/CN100465141C/zh not_active Expired - Lifetime
- 2004-02-24 WO PCT/US2004/005540 patent/WO2004076387A2/en active Application Filing
- 2004-02-24 EP EP04714203A patent/EP1606234B1/en not_active Expired - Fee Related
- 2004-02-24 RU RU2005129711/04A patent/RU2298541C2/ru not_active IP Right Cessation
- 2004-02-24 JP JP2006503850A patent/JP4667365B2/ja not_active Expired - Fee Related
- 2004-02-24 MX MXPA05008417A patent/MXPA05008417A/es active IP Right Grant
-
2005
- 2005-08-24 ZA ZA200506798A patent/ZA200506798B/en unknown
-
2006
- 2006-06-08 US US11/449,548 patent/US7524467B2/en not_active Expired - Lifetime
-
2009
- 2009-12-11 AU AU2009248464A patent/AU2009248464B2/en not_active Ceased
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03178935A (ja) * | 1989-11-28 | 1991-08-02 | Inst Fr Petrole | 天然ガスからのアルキル芳香族炭化水素の製造方法 |
WO1995032166A1 (en) * | 1994-05-23 | 1995-11-30 | Chemical Research & Licensing Company | Alkylation of organic aromatic compounds |
JP2003503378A (ja) * | 1999-06-29 | 2003-01-28 | セラニーズ・インターナショナル・コーポレーション | エチレン回収システム |
Also Published As
Publication number | Publication date |
---|---|
BRPI0407706A (pt) | 2006-02-14 |
CA2516648A1 (en) | 2004-09-10 |
CA2516648C (en) | 2012-05-01 |
US20060229479A1 (en) | 2006-10-12 |
EP1606234A2 (en) | 2005-12-21 |
RU2005129711A (ru) | 2006-03-20 |
ZA200506798B (en) | 2006-05-31 |
AU2004215343A1 (en) | 2004-09-10 |
JP2006518762A (ja) | 2006-08-17 |
BRPI0407706B1 (pt) | 2014-04-15 |
AU2004215343B2 (en) | 2010-01-07 |
KR20050106042A (ko) | 2005-11-08 |
US20040167371A1 (en) | 2004-08-26 |
KR101016880B1 (ko) | 2011-02-22 |
RU2298541C2 (ru) | 2007-05-10 |
CN1753851A (zh) | 2006-03-29 |
AU2009248464A1 (en) | 2010-01-07 |
MXPA05008417A (es) | 2005-10-19 |
CN100465141C (zh) | 2009-03-04 |
US7074978B2 (en) | 2006-07-11 |
AU2009248464B2 (en) | 2011-08-25 |
EP1606234B1 (en) | 2012-04-11 |
WO2004076387A2 (en) | 2004-09-10 |
US7524467B2 (en) | 2009-04-28 |
WO2004076387A3 (en) | 2004-10-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4667365B2 (ja) | アルキルベンゼンの製造プロセス | |
US7517506B2 (en) | Process for the production of alkylbenzene with ethane stripping | |
ZA200506862B (en) | Process for the production of alkylaromatics | |
KR102223242B1 (ko) | 에탄 회수 공정 및 에탄 회수를 수반하는 알킬화 공정 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20090727 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100316 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20100615 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20100712 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100715 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100824 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20101118 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20101214 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20110111 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140121 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4667365 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |