JP7416824B2 - エチルベンゼン脱水素触媒活性を維持するためのシステム及びプロセス - Google Patents
エチルベンゼン脱水素触媒活性を維持するためのシステム及びプロセス Download PDFInfo
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- JP7416824B2 JP7416824B2 JP2021561914A JP2021561914A JP7416824B2 JP 7416824 B2 JP7416824 B2 JP 7416824B2 JP 2021561914 A JP2021561914 A JP 2021561914A JP 2021561914 A JP2021561914 A JP 2021561914A JP 7416824 B2 JP7416824 B2 JP 7416824B2
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- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 title claims description 128
- 239000003054 catalyst Substances 0.000 title claims description 55
- 238000000034 method Methods 0.000 title claims description 52
- 238000006356 dehydrogenation reaction Methods 0.000 title claims description 36
- 230000000694 effects Effects 0.000 title claims description 18
- 239000007788 liquid Substances 0.000 claims description 97
- 238000002347 injection Methods 0.000 claims description 84
- 239000007924 injection Substances 0.000 claims description 84
- 239000000243 solution Substances 0.000 claims description 60
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 50
- 229910052700 potassium Inorganic materials 0.000 claims description 44
- 239000011591 potassium Substances 0.000 claims description 43
- 229910052783 alkali metal Inorganic materials 0.000 claims description 40
- 150000001340 alkali metals Chemical class 0.000 claims description 39
- 238000011144 upstream manufacturing Methods 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 17
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 16
- 239000003513 alkali Substances 0.000 claims description 14
- 239000002245 particle Substances 0.000 claims description 11
- 239000011261 inert gas Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000007921 spray Substances 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 4
- 230000008016 vaporization Effects 0.000 claims description 4
- 239000002826 coolant Substances 0.000 claims description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 37
- 150000001875 compounds Chemical class 0.000 description 11
- -1 alkyl aromatic hydrocarbons Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 159000000001 potassium salts Chemical class 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 150000004996 alkyl benzenes Chemical class 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 238000009413 insulation Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 6
- 239000000155 melt Substances 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 150000003112 potassium compounds Chemical class 0.000 description 4
- 230000008929 regeneration Effects 0.000 description 4
- 238000011069 regeneration method Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910001338 liquidmetal Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000010793 Steam injection (oil industry) Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali- or alkaline earth metals
-
- 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
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/321—Catalytic processes
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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
- B01J14/00—Chemical processes in general for reacting liquids with liquids; Apparatus specially adapted therefor
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
- B01J23/04—Alkali metals
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/90—Regeneration or reactivation
- B01J23/94—Regeneration or reactivation of catalysts comprising metals, oxides or hydroxides of the iron group metals or copper
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- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/008—Details of the reactor or of the particulate material; Processes to increase or to retard the rate of reaction
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
- C07C5/333—Catalytic processes
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00796—Details of the reactor or of the particulate material
- B01J2208/00893—Feeding means for the reactants
- B01J2208/00902—Nozzle-type feeding elements
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- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C2523/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36 with alkali- or alkaline earth metals or beryllium
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
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Description
Claims (17)
- エチルベンゼンを脱水素化するためのプロセスであって、
蒸気ストリーム及びエチルベンゼンストリームを混合してエチルベンゼン/蒸気フィード混合物を形成する工程、
上記エチルベンゼン/蒸気フィード混合物を、アルカリ金属促進触媒を含む脱水素反応器に供給して、上記エチルベンゼンの一部をスチレンに変換する工程、
上記蒸気ストリーム、上記エチルベンゼンストリーム、又は上記エチルベンゼン/蒸気フィード混合物のうち少なくとも1種を含むフィードストリームに、アルカリ金属液、アルカリ金属化合物液、又はアルカリ金属を含む溶液から選択される液体を注入する工程であって、該液体は、上記脱水素反応器の上流で上記フィードストリーム中に気化及び分散する工程、
注入の上流の地点から注入ノズルまで上記液体を液体状態に維持する工程、及び、
上記注入ノズルを通して上記液体の注入と純水ストリームの注入とを交互に行う工程
を含むプロセス。 - 上記アルカリ金属促進触媒がカリウム促進触媒を含む、請求項1に記載のプロセス。
- 上記アルカリ金属を含む溶液が、水中に0.02~0.5重量%のアルカリ金属を含む、請求項1に記載のプロセス。
- 上記注入工程が、
上記注入ノズルを通して上記液体を分散させて、上記フィードストリーム中に分散した液体の小滴を形成する工程、及び
上記液体を上記フィードストリーム中に蒸発させる工程
を含む、請求項1に記載のプロセス。 - 上記分散小滴の初期粒径が75ミクロン以下である、請求項4に記載のプロセス。
- 上記注入ノズルが、上記フィードストリーム内の中央に設置されている、請求項4に記載のプロセス。
- 上記フィードストリームの周囲に配置され、かつ上記フィードストリームの中央に向かって上記フィードと並流で噴霧するよう構成された2つ以上の注入ノズルを通して上記液体を分散させる工程を含む、請求項4に記載のプロセス。
- 上記注入工程が、上記液体を不活性ガスで微粒化する工程を含む、請求項4に記載のプロセス。
- 上記蒸発工程が、上記分散小滴を上記フィードストリーム中に約10mの距離内で蒸発させる工程を含む、請求項4に記載のプロセス。
- エチルベンゼン脱水素反応器において触媒活性を維持するためのシステムであって、
アルカリ金属、アルカリ金属化合物液、及びアルカリ金属を含む溶液のうち少なくとも1種から選択される液体アルカリフィードを液体状態に維持するよう構成された液体アルカリフィード、
蒸気ストリーム、エチルベンゼンフィードストリーム、及びエチルベンゼン/蒸気フィードストリームから選択されるプロセスフィードストリームに上記液体アルカリフィードを液体として注入してアルカリ含有フィードを形成するための注入ノズル、
上記注入ノズルに流体的に接続された水フィードストリーム、
上記液体アルカリフィード及び上記水フィードストリームを上記注入ノズルに交互に供給するよう構成された制御システム、及び、
アルカリ金属促進触媒を含み、かつ上記アルカリ含有フィード又は上記アルカリ含有フィードを含む混合物を受け入れるための入口を有する脱水素反応器
を含むシステム。 - 上記液体アルカリフィードが、上記注入ノズルの上流で上記液体アルカリフィードを液体として維持するために蒸気トレース、断熱、又は冷却材トレースされている、請求項10に記載のシステム。
- 上記注入ノズルが、上記プロセスフィードストリームの軸中心に近接して設置されている、請求項10に記載のシステム。
- 上記プロセスフィードストリームの周囲に設置された2つ以上の注入ノズルを含む、請求項10に記載のシステム。
- 上記ノズルが、上記液体アルカリフィードを、初期粒径が75ミクロン以下である小滴の形態で分散させるよう構成されている、請求項10に記載のシステム。
- 上記注入ノズルに流体的に接続された不活性ガスフィードストリームをさらに含む、請求項10に記載のシステム。
- 上記注入ノズルが、上記脱水素反応器から上流へ約5m~10m離れて主エチルベンゼン/蒸気フィードストリーム中に配置されている、請求項10に記載のシステム。
- 上記注入ノズルが、液体小滴の噴霧を上記プロセスフィードストリームの中央部内に維持するよう構成されている、請求項10に記載のシステム。
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US5358698A (en) * | 1991-02-26 | 1994-10-25 | Fina Technology, Inc. | Apparatus for dehydrogenation of ethylbenzene to styrene |
US5461179A (en) * | 1993-07-07 | 1995-10-24 | Raytheon Engineers & Constructors, Inc. | Regeneration and stabilization of dehydrogenation catalysts |
US5739071A (en) | 1993-07-07 | 1998-04-14 | Raytheon Engineers & Constructors, Inc. | Method and apparatus for regeneratinig and stabilizing dehydrogenation catalysts |
US6936743B2 (en) | 2002-09-05 | 2005-08-30 | Fina Technology, Inc. | Method for extending catalyst life in processes for preparing vinyl aromatic hydrocarbons |
US20060183953A1 (en) | 2005-02-15 | 2006-08-17 | Fina Technology, Inc. | Method and apparatus for addition of aqueous solutions to high temperature processes |
US20060224029A1 (en) | 2005-03-29 | 2006-10-05 | Fina Technology, Inc. | Method of extending catalyst life in vinyl aromatic hydrocarbon formation |
EP2000450A1 (en) * | 2007-06-05 | 2008-12-10 | Total Petrochemicals France | Regeneration and stabilization of dehydrogenation catalyst |
US8648007B2 (en) | 2008-04-22 | 2014-02-11 | Fina Technology, Inc. | Vaporization and transportation of alkali metal salts |
US7964765B2 (en) * | 2008-06-14 | 2011-06-21 | Lummus Technology Inc. | Styrene monomer process based on oxidative dehydrogenation of ethylbenzene using CO2 as a soft oxidant |
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US10961169B2 (en) * | 2019-04-18 | 2021-03-30 | Lummus Technology Llc | Systems and processes for maintaining ethylbenzene dehydration catalyst activity |
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