JP6914362B2 - トランスアルキル化プロセスおよびそれに使用される触媒組成物 - Google Patents
トランスアルキル化プロセスおよびそれに使用される触媒組成物 Download PDFInfo
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- JP6914362B2 JP6914362B2 JP2019560040A JP2019560040A JP6914362B2 JP 6914362 B2 JP6914362 B2 JP 6914362B2 JP 2019560040 A JP2019560040 A JP 2019560040A JP 2019560040 A JP2019560040 A JP 2019560040A JP 6914362 B2 JP6914362 B2 JP 6914362B2
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- Prior art keywords
- stream
- benzene
- transalkylation
- zeolite
- mcm
- Prior art date
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- 238000010555 transalkylation reaction Methods 0.000 title claims description 91
- 239000000203 mixture Substances 0.000 title claims description 87
- 238000000034 method Methods 0.000 title claims description 50
- 230000003197 catalytic effect Effects 0.000 title claims description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 128
- 239000003054 catalyst Substances 0.000 claims description 120
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 73
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 72
- 239000010457 zeolite Substances 0.000 claims description 65
- 238000005804 alkylation reaction Methods 0.000 claims description 57
- 150000001491 aromatic compounds Chemical class 0.000 claims description 54
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 54
- 229910021536 Zeolite Inorganic materials 0.000 claims description 49
- 230000029936 alkylation Effects 0.000 claims description 45
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 42
- 150000001555 benzenes Polymers 0.000 claims description 33
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical group CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 28
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 27
- 125000001997 phenyl group Polymers [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 229940100198 alkylating agent Drugs 0.000 claims description 26
- 239000002168 alkylating agent Substances 0.000 claims description 26
- 150000004951 benzene Polymers 0.000 claims description 26
- 239000007791 liquid phase Substances 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 22
- 239000002808 molecular sieve Substances 0.000 claims description 22
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 22
- 239000000377 silicon dioxide Substances 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 14
- 239000012535 impurity Substances 0.000 claims description 12
- 229910052680 mordenite Inorganic materials 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 8
- 150000002910 rare earth metals Chemical class 0.000 claims description 8
- 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 7
- 230000002152 alkylating effect Effects 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 claims description 2
- 239000012013 faujasite Substances 0.000 claims description 2
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 6
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- 230000002378 acidificating effect Effects 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
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- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- HILAULICMJUOLK-UHFFFAOYSA-N 1,3-diethyl-5-methylbenzene Chemical compound CCC1=CC(C)=CC(CC)=C1 HILAULICMJUOLK-UHFFFAOYSA-N 0.000 description 2
- AFZZYIJIWUTJFO-UHFFFAOYSA-N 1,3-diethylbenzene Chemical compound CCC1=CC=CC(CC)=C1 AFZZYIJIWUTJFO-UHFFFAOYSA-N 0.000 description 2
- DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 description 2
- MEMBJMDZWKVOTB-UHFFFAOYSA-N 1-ethyl-2,4-dimethylbenzene Chemical group CCC1=CC=C(C)C=C1C MEMBJMDZWKVOTB-UHFFFAOYSA-N 0.000 description 2
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- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- OGVRJXPGSVLDRD-UHFFFAOYSA-N 2,3-dimethylanthracene Chemical compound C1=CC=C2C=C(C=C(C(C)=C3)C)C3=CC2=C1 OGVRJXPGSVLDRD-UHFFFAOYSA-N 0.000 description 2
- GYMFBYTZOGMSQJ-UHFFFAOYSA-N 2-methylanthracene Chemical compound C1=CC=CC2=CC3=CC(C)=CC=C3C=C21 GYMFBYTZOGMSQJ-UHFFFAOYSA-N 0.000 description 2
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- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 2
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- BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
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- 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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- 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
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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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7038—MWW-type, e.g. MCM-22, ERB-1, ITQ-1, PSH-3 or SSZ-25
-
- 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
- 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
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- 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
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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
- C07C2529/08—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
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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
- C07C2529/70—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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- 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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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
ラブレス、ブレット、ティー;ビークマン、ジーン、ダブリュー;オリバリー、クリストファー、ジー;ウェイジェル、スコット、ジェイ;アイド、マシュー、エス;バウムラッカー、テリーサ、エー
関連出願の相互参照
本出願は2017年1月25日に出願された米国特許仮出願第62/450,122号および2017年3月20日に出願された欧州特許出願第17161741.8号の優先権およびその利益を主張し、これらの開示内容はその全体が参照によって組み入れられる。
技術分野
定義
(i)通常の一次結晶構成ブロックの「MWW骨格トポロジーを有する単位格子」から作られたモレキュラーシーブ。単位格子は原子の空間配置であり、それは3次元空間内に嵌め込まれて、Ch.Baerlocher、W.M.MeierおよびD.H.Olsonによる「ゼオライト骨格タイプのアトラス」(Elsevier社、第5版、2001年)に記載された結晶を記述する。
(ii)通常の二次構成ブロックから作られたモレキュラーシーブであって、この二次構成ブロックはそのようなMWW骨格タイプ単位格子の2次元嵌め込みであり、1個の単位格子の厚さ、好ましくは1個のc軸単位格子の厚さの単層を形成するもの。
(iii)通常の二次構成ブロックから作られたモレキュラーシーブであって、この二次構成ブロックは「1個以上の単位格子の厚さの層」であり、1個より多い単位格子の厚さの層はMWW骨格トポロジー単位格子の少なくとも2つの単層を積み重ね、詰め込みまたは結合することによって作られるもの。そのような二次構成ブロックの積み重ねは、規則的な様式、不規則な様式、ランダムの様式またはこれらの任意の組み合わせであることができる。および
(iv)任意の規則的なまたはランダムの、2次元または3次元のMWW骨格トポロジーを有する単位格子の組み合わせによって作られたモレキュラーシーブ。
プロセス
トランスアルキル化およびアルキル化条件
アルキル化されることが可能な芳香族化合物
アルキル化剤
ガード床
トランスアルキル化触媒組成物
当該FAU骨格構造は13X、低ナトリウム超安定Y(USY)、脱アルミニウムY(Deal Y)、超疎水性Y(UHP−Y)、希土類交換Y(REY)、希土類交換USY(RE−USY)およびこれらの混合物から成る群から選ばれ;
当該BEA*骨格構造を有する当該ゼオライトはベータゼオライトであり;
MOR骨格構造を有する当該ゼオライトは、モルデナイト、EMM−34、TEA−モルデナイトおよびこれらの混合物から成る群から選ばれ;
当該MWW骨格構造を有する当該ゼオライトはMCM−22ファミリー材料であり、当該MCM−22ファミリーのモレキュラーシーブは、MCM−22、PSH−3、SSZ−25、MCM−36、MCM−49、MCM−56、ERB−1、EMM−10、EMM−10−P、EMM−12、EMM−13、UZM−8、UZM−8HS、UZM−37、ITQ−1、ITQ−2、ITQ−30またはこれらの2種以上の組み合わせのいずれか1種であり;
当該トランスアルキル化触媒は30cm−1〜85cm−1の範囲内の外部表面積/体積比を有し;かつ
当該ゼオライトは当該トランスアルキル化触媒組成物の65重量%〜80重量%を占めている。
アルキル化触媒
触媒再生
[実施例]
USYゼオライトSi/Al 2 モル比がトランスアルキル化性能に及ぼす効果
実施例1および2の触媒調製
実施例1および2の触媒のトランスアルキル化性能評価
表1から分かるように、より低い温度の操業が同じDEB転化率および同じPEB処理量で達成される。あるいは、より高いPEB処理量が同じ温度および同じDEB転化率で達成される。
USYゼオライト触媒の粒子サイズおよび形状がトランスアルキル化触媒活性に及ぼす効果
実施例3〜6の触媒調製
*直径は最小値と交差して測定された。
実施例3〜6についての触媒活性の評価
Claims (10)
- 以下の工程を含むエチルベンゼンまたはクメンを製造するプロセス:
(a)トランスアルキル化触媒組成物を反応ゾーンに供給する工程であって、前記トランスアルキル化触媒が、FAU、BEA*、MOR、MWWおよびこれらの混合物から成る群から選ばれた骨格構造を有するゼオライトを含んでおり、前記ゼオライトのシリカ−アルミナモル比が10〜15の範囲内にあり、前記トランスアルキル化触媒組成物が40cm −1 〜80cm −1 の範囲内に外部表面積/体積比を有する押し出し成形物の形態をしている、工程;
(b)ポリアルキル化ベンゼンを含んでいる流れ、およびアルキル化されることが可能な芳香族化合物流れの一部を前記反応ゾーンに供給する工程であって、前記ポリアルキル化ベンゼン流れがジエチルベンゼンまたはジイソプロピルベンゼンを含んでおり、また前記アルキル化されることが可能な芳香族化合物流れがベンゼンを含んでいる、工程;
(c)前記ポリアルキル化ベンゼン流れと前記アルキル化されることが可能な芳香族化合物流れとを、少なくとも部分的な液相トランスアルキル化条件の下で前記トランスアルキル化触媒組成物の存在下に接触させ、前記アルキル化されることが可能な芳香族化合物をアルキル化してエチルベンゼンまたはクメンを含んでいるトランスアルキル化流出物流れを製造する工程であって、
前記少なくとも部分的な液相トランスアルキル化条件が、100℃〜200℃の温度および200kPa−a〜600kPa−aの圧力を含み、
前記トランスアルキル化触媒組成物の触媒活性が、前記ゼオライトを含んでおり25〜37の範囲内のシリカ−アルミナモル比を有する、より高いシリカ含有量のトランスアルキル化触媒組成物の触媒活性よりも、前記両触媒組成物が同等のトランスアルキル化条件の下で比較された場合に高い、工程;
(d)アルキル化剤を含んでいる流れ、および前記アルキル化されることが可能な芳香族化合物流れの別の部分を別の反応ゾーンに供給する工程;
(e)前記アルキル化されることが可能な芳香族化合物流れの前記別の部分と前記アルキル化剤を含んでいる流れとを、アルキル化条件の下でアルキル化触媒の存在下に接触させ、前記アルキル化されることが可能な芳香族化合物をアルキル化してモノアルキル化ベンゼンおよび前記ポリアルキル化ベンゼンを含んでいるアルキル化流出物を製造する工程であって、
前記アルキル化触媒がアルミノシリケートを含んでおり、前記アルミノシリケートが、MCM−22ファミリーのモレキュラーシーブ、フォージャサイト、モルデナイト、ベータゼオライトまたはこれらの2種以上の組み合わせのいずれか1種であり、
前記アルキル化条件が少なくとも部分的な液相条件であり、150℃〜300℃の温度、20000kPaまでの圧力および前記アルキル化剤の重量に基いて0.1時−1 〜30時−1のWHSVを含む、工程;
(f)前記アルキル化流出物を分けて、前記ポリアルキル化ベンゼン流れを回収する工程;
(g)前記ポリアルキル化ベンゼン流れの少なくとも一部を工程(b)に供給する工程;
(h)前記トランスアルキル化流出物流れを分けて、エチルベンゼン流れまたはクメン流れを回収する工程;および
(i)前記アルキル化流出物流れを分けて、エチルベンゼン流れまたはクメン流れを回収する工程。 - ベンゼンを含んでいる前記アルキル化されることが可能な芳香族化合物流れが、窒素含有不純物をさらに含んでいる未精製の流れである、請求項1に記載のプロセス。
- 前記未精製の流れを処理条件の下で処理材料と接触させて、前記窒素含有不純物の少なくとも一部を除去する工程をさらに含み、
前記処理条件が30℃〜200℃の温度、0.1時−1 〜200時−1の重量時空間速度(WHSV)および大気圧〜3000kPa−aの圧力を含み、
前記処理材料が、粘土、樹脂、活性アルミナ、モレキュラーシーブおよびこれらの組み合わせから成る群から選ばれ、前記モレキュラーシーブが、リンデX、リンデA、ベータゼオライト、フォージャサイト、Yゼオライト、超安定Y(USY)、脱アルミニウムY(DealY)、レアアースY(REY)、超疎水性Y(UHP−Y)、モルデナイト、TEA−モルデナイト、ZSM−3、ZSM−4、ZSM−14、ZSM−18、ZSM−20およびこれらの組み合わせから成る群から選ばれる、
請求項2に記載のプロセス。 - 前記モノアルキル化ベンゼンがエチルベンゼンであり、前記ポリアルキル化ベンゼンがポリエチルベンゼンであり、かつ前記アルキル化剤がエチレンである、または前記モノアルキル化ベンゼンがクメンであり、前記ポリアルキル化ベンゼンがポリイソプロピルベンゼンであり、かつ前記アルキル化剤がプロピレンである、請求項1〜3のいずれか1項に記載のプロセス。
- 前記トランスアルキル化触媒組成物の前記存在の下での前記ポリアルキル化ベンゼン流れの重量時空間速度が、25〜37の範囲内のシリカ−アルミナモル比を有する前記より高いシリカ含有量のトランスアルキル化触媒組成物の存在の下での重量時空間速度よりも、前記両触媒組成物が同等のトランスアルキル化条件の下で比較された場合に高い、請求項1〜4のいずれか1項に記載のプロセス。
- 前記FAU骨格構造を有する前記ゼオライトが、13X、低ナトリウム超安定Y(USY)、脱アルミニウムY(Deal Y)、超疎水性Y(UHP−Y)、希土類交換Y(REY)、希土類交換USY(RE−USY)およびこれらの混合物から成る群から選ばれる、請求項1〜5のいずれか1項に記載のプロセス。
- 前記BEA*骨格構造を有する前記ゼオライトが、ベータゼオライトである、請求項1〜6のいずれか1項に記載のプロセス。
- 前記MOR骨格構造を有する前記ゼオライトが、モルデナイト、EMM−34、TEA−モルデナイトおよびこれらの混合物から成る群から選ばれる、請求項1〜7のいずれか1項に記載のプロセス。
- 前記MWW骨格構造を有する前記ゼオライトが、MCM−22ファミリーのモレキュラーシーブまたはこれらの組み合わせである、請求項1〜8のいずれか1項に記載のプロセス。
- 前記MCM−22ファミリーのモレキュラーシーブが、MCM−22、PSH−3、SSZ−25、MCM−36、MCM−49、MCM−56、ERB−1、EMM−10、EMM−10−P、EMM−12、EMM−13、UZM−8、UZM−8HS、UZM−37、ITQ−1、ITQ−2、ITQ−30またはこれらの2種以上の組み合わせのいずれか1種である、請求項9に記載のプロセス。
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US11739274B2 (en) | 2019-08-20 | 2023-08-29 | Exxon Mobil Technology and Engineering Company | Metal-organic framework catalysts and their use thereof in catalytic cracking |
US20230286889A1 (en) * | 2020-09-30 | 2023-09-14 | Uop Llc | Transalkylation of alkylated phenols |
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RU2075467C1 (ru) * | 1990-12-17 | 1997-03-20 | Дзе Дау Кемикал Компани | Способ получения этилбензола или кумола |
US6936744B1 (en) * | 2000-07-19 | 2005-08-30 | Exxonmobil Chemical Patents, Inc. | Alkylaromatics production |
US20020042548A1 (en) * | 2001-07-11 | 2002-04-11 | Dandekar Ajit B. | Process for producing cumene |
RU2246474C1 (ru) * | 2003-11-24 | 2005-02-20 | Иванова Ирина Игоревна | Способ получения алкилированных полициклических ароматических углеводородов |
US6894201B1 (en) * | 2003-12-19 | 2005-05-17 | Uop Llc | Process and apparatus for the removal of nitrogen compounds from a fluid stream |
WO2006107452A1 (en) * | 2005-03-31 | 2006-10-12 | Exxonmobil Chemical Patents Inc. | A process of using a high activity catalyst for the transalkylation of aromatics |
SG10201607877SA (en) * | 2006-05-24 | 2016-11-29 | Exxonmobil Chemical Patents Inc | Monoalkylated aromatic compound production |
GB0806422D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
US20080171649A1 (en) * | 2007-01-12 | 2008-07-17 | Deng-Yang Jan | Modified Y-85 and LZ-210 Zeolites |
US7517825B2 (en) * | 2007-01-12 | 2009-04-14 | Uop Llc | Aromatic transalkylation using a LZ-210 zeolite |
US20080171902A1 (en) * | 2007-01-12 | 2008-07-17 | Deng-Yang Jan | Aromatic Transalkylation Using a Y-85 Zeolite |
JP2010515568A (ja) * | 2007-01-12 | 2010-05-13 | ユーオーピー エルエルシー | Y−85および修飾lz−210ゼオライト |
US7737314B2 (en) * | 2007-02-12 | 2010-06-15 | Exxonmobil Chemical Patents Inc. | Production of high purity ethylbenzene from non-extracted feed and non-extracted reformate useful therein |
US9365469B2 (en) * | 2011-09-14 | 2016-06-14 | Uop Llc | Process for transalkylating aromatic hydrocarbons |
WO2014182294A1 (en) * | 2013-05-08 | 2014-11-13 | Badger Licensing Llc | Aromatics alkylation process |
WO2014182434A1 (en) * | 2013-05-09 | 2014-11-13 | Exxonmobil Chemical Patents Inc. | Treatment of aromatic alkylation catalysts |
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EP3573942B1 (en) | 2021-12-01 |
CN110214131A (zh) | 2019-09-06 |
CA3049411C (en) | 2021-02-16 |
CN110214131B (zh) | 2022-08-09 |
JP2020505455A (ja) | 2020-02-20 |
EP3573942A1 (en) | 2019-12-04 |
ZA201904080B (en) | 2020-12-23 |
RU2753341C2 (ru) | 2021-08-13 |
RU2019126013A3 (ja) | 2021-02-26 |
ES2902875T3 (es) | 2022-03-30 |
CA3049411A1 (en) | 2018-08-02 |
US20200385322A1 (en) | 2020-12-10 |
KR102315640B1 (ko) | 2021-10-21 |
RU2019126013A (ru) | 2021-02-26 |
KR20190095465A (ko) | 2019-08-14 |
SG11201906175SA (en) | 2019-08-27 |
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