JP6453359B2 - 低温での固体イオン交換による金属交換されたメタロアルミノホスフェートの製造方法 - Google Patents
低温での固体イオン交換による金属交換されたメタロアルミノホスフェートの製造方法 Download PDFInfo
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- JP6453359B2 JP6453359B2 JP2016561361A JP2016561361A JP6453359B2 JP 6453359 B2 JP6453359 B2 JP 6453359B2 JP 2016561361 A JP2016561361 A JP 2016561361A JP 2016561361 A JP2016561361 A JP 2016561361A JP 6453359 B2 JP6453359 B2 JP 6453359B2
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- metal
- metalloaluminophosphate
- exchanged
- starting materials
- sapo
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- 238000000034 method Methods 0.000 title claims description 51
- 238000005342 ion exchange Methods 0.000 title claims description 19
- 230000008569 process Effects 0.000 title claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 44
- 239000000463 material Substances 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 34
- 239000012298 atmosphere Substances 0.000 claims description 24
- 239000010949 copper Substances 0.000 claims description 24
- 229910052751 metal Inorganic materials 0.000 claims description 23
- 239000002184 metal Substances 0.000 claims description 23
- 229910021529 ammonia Inorganic materials 0.000 claims description 22
- 239000007789 gas Substances 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 21
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
- 239000007858 starting material Substances 0.000 claims description 17
- 150000002736 metal compounds Chemical class 0.000 claims description 14
- 239000003638 chemical reducing agent Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 229910052742 iron Inorganic materials 0.000 claims description 9
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 9
- 150000002500 ions Chemical class 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 150000002739 metals Chemical class 0.000 claims description 6
- 239000012229 microporous material Substances 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 239000011135 tin Substances 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 230000001747 exhibiting effect Effects 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 16
- 229910021536 Zeolite Inorganic materials 0.000 description 7
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 7
- 229910044991 metal oxide Inorganic materials 0.000 description 7
- 150000004706 metal oxides Chemical class 0.000 description 7
- 239000010457 zeolite Substances 0.000 description 7
- 229910052802 copper Inorganic materials 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- -1 H + Chemical class 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 229910001463 metal phosphate Inorganic materials 0.000 description 3
- 239000006069 physical mixture Substances 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910001960 metal nitrate Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 241000989363 Stenolophus comma Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F01—MACHINES OR ENGINES IN GENERAL; ENGINE PLANTS IN GENERAL; STEAM ENGINES
- F01N—GAS-FLOW SILENCERS OR EXHAUST APPARATUS FOR MACHINES OR ENGINES IN GENERAL; GAS-FLOW SILENCERS OR EXHAUST APPARATUS FOR INTERNAL COMBUSTION ENGINES
- F01N3/00—Exhaust or silencing apparatus having means for purifying, rendering innocuous, or otherwise treating exhaust
- F01N3/08—Exhaust or silencing apparatus having means for purifying, rendering innocuous, or otherwise treating exhaust for rendering innocuous
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- F01N3/18—Exhaust or silencing apparatus having means for purifying, rendering innocuous, or otherwise treating exhaust for rendering innocuous by thermal or catalytic conversion of noxious components of exhaust characterised by methods of operation; Control
- F01N3/20—Exhaust or silencing apparatus having means for purifying, rendering innocuous, or otherwise treating exhaust for rendering innocuous by thermal or catalytic conversion of noxious components of exhaust characterised by methods of operation; Control specially adapted for catalytic conversion ; Methods of operation or control of catalytic converters
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Description
a)イオン交換能を示す一種又は二種以上のメタロアルミノホスフェート出発材料、及び
b)一種又は二種以上の金属化合物
を含有する乾燥混合物を提供する工程;
アンモニアを含有するガス雰囲気中で、該金属化合物のイオン及び結晶性マイクロポラス材料のイオンの固体イオン交換を開始させ、かつ、遂行するのに十分な温度及び時間、該混合物を加熱する工程;及び
金属交換されたマイクロポラスのメタロアルミノホスフェート材料又は金属交換されたマイクロポラスのメタロアルミノホスフェート材料を含有する混合物を得る工程、を含む固体イオン交換法を提供する。
本発明の特徴は次の通りである。
1. 金属交換された結晶性マイクロポラスのメタロアルミノホスフェート又は金属交換された結晶性マイクロポラスのメタロアルミノホスフェートを含有する混合物の製造方法であって、
a)イオン交換能を示す一種又は二種以上のメタロアルミノホスフェート出発材料、及びb)一種又は二種以上の金属化合物
を含有する乾燥混合物を提供する工程;
アンモニアを含有するガス雰囲気中で、該金属化合物のイオン及び該結晶性マイクロポラスの材料のイオンの固体イオン交換を開始させ、かつ、遂行するのに十分な温度、かつ、時間該混合物を加熱する工程;及び
金属交換された結晶性マイクロポラスのメタロアルミノホスフェート材料又は金属交換された結晶性マイクロポラスのメタロアルミノホスフェート材料を含有する混合物を得る工程、
を含む上記の方法。
2. 前記一種又は二種以上のメタロアルミノホスフェート出発材料が、ケイ素、チタン、スズ、亜鉛、マグネシウム、マンガン、コバルト又は鉄の群から選択される一種又は二種以上の金属を含有する、上記の特徴1に記載の方法。
3. 前記一種又は二種以上のメタロアルミノホスフェート出発材料が、CHA、AEI、AFI、AEL、AST、AFR、AFO及びFAUのフレームワークコードを有する、上記の特徴1又は2に記載の方法。
4. 前記一種又は二種以上のメタロアルミノホスフェート出発材料が、SAPO−34、SAPO−44、SAPO−18又はそれらの組合せの群から選択される、上記の特徴1〜3のいずれか一つに記載の方法。
5. 前記一種又は二種以上のマイクロポラスのメタロアルミノホスフェート出発材料が、H + 又はNH 4 + の形態にある、上記の特徴1〜4のいずれか一つに記載の方法。
6. 前記一種又は二種以上のマイクロポラスの金属のホスフェート出発材料が、有機構造指向剤を含有する、上記の特徴1〜5のいずれか一つに記載の方法。
7. 前記乾燥混合物中の前記一種又は二種以上の金属化合物が、金属酸化物、金属硝酸塩、金属ホスフェート、金属硫酸塩、金属シュウ酸塩、金属酢酸塩又はそれらの組合せの群から選択される、上記の特徴1〜6のいずれか一つに記載の方法。
8. 前記一種又は二種以上の金属化合物中の金属が、Fe、Co、Cuの群から選択される、上記の特徴1〜7のいずれか一つに記載の方法。
9. 前記一種又は二種以上の金属化合物が、Fe及び/又はCuの酸化物からなる、上記の特徴1〜7のいずれか一つに記載の方法。
10. 前記一種又は二種以上の金属化合物が、酸化Cu(I)及び/又は酸化Cu(II)である、上記の特徴1〜9のいずれか一つに記載の方法。
11. 前記雰囲気中のアンモニアの含有量が、1〜5000体積ppmである、上記の特徴1〜10のいずれか一つに記載の方法。
12. 酸素が10体積%以下の量で前記雰囲気中に含有されている、上記の特徴1〜11のいずれか一つに記載の方法。
13. 前記ガス雰囲気が、5体積%水以下を含有している、上記の特徴1〜12のいずれか一つに記載の方法。
14. 前記混合物が、アンモニアを含有する前記ガス雰囲気中で300℃未満の温度に加熱される、上記の特徴1〜13のいずれかひとつに記載の方法。
15. 前記混合物が、アンモニアを含有する前記ガス雰囲気中で100℃〜250℃の温度に加熱される、上記の特徴1〜14のいずれか一つに記載の方法。
16. 上記の特徴1〜15のいずれか一つに記載の方法によって得られる金属交換されたマイクロポラスのメタロアルミノホスフェート材料又は金属交換されたマイクロポラスのメタロアルミノホスフェート材料の混合物。
17. 上記の特徴1〜15のいずれか一つに記載の方法によって得られた金属交換された結晶性マイクロポラスのメタロアルミノホスフェート材料又は金属交換された結晶性マイクロポラスのメタロアルミノホスフェート材料の混合物を含む触媒に排ガスを接触させることを含む、還元剤による選択的接触還元によって該排ガスから窒素酸化物を除去する方法。
18. 前記還元剤がアンモニア又はそれの前駆体である、上記の特徴17に記載の方法。
19. 前記還元剤が炭化水素を含む、上記の特徴17に記載の方法。
CuOとH−SAPO−34材料とを、12.5重量%CuOの含有量になるように混合することによって触媒を製造した。該触媒の試料を、石英のU字管リアクターに投入して、N2中に500ppmNH3を含有する雰囲気中で10時間かけて250℃に加熱した。その加熱後、触媒を160℃に冷却し、そしてN2中に500ppmのNO、533ppmのNH3、5体積%のH2O、10体積%のO2を含有するガス混合物に曝した。その後、その温度を、180、200及び220℃に段階的に高め、そして材料のSCR活性に関する記録として、2700NL/触媒1g時間の空間速度でNOの変換率を測定した。
比較のために、CuOとH−SAPO−34材料とを、12.5重量%CuOの含有量になるように混合して、実施例1に記載した触媒と同様の触媒を製造した。触媒の試料を、石英のU字管リアクターに投入して、純粋なN2雰囲気中で10時間かけて250℃に加熱した。その加熱後、触媒を160℃に冷却し、そしてN2中500ppmのNO、533ppmのNH3、5体積%のH2O、10体積%のO2のガス混合物に曝した。その後、その温度を、180、200及び220℃に段階的に高め、そして材料のSCR活性に関する記録として、2700NL/触媒1g時間の空間速度でNOの変換率を測定した。
この実施例は、SCRに活性の金属交換されたメタロアルミノホスフェート触媒が、Cu2Oを用いる本発明の方法によって300℃未満で製造できることを示す。10重量%のCu2OとH−SAPO−34ゼオライトとの乾燥混合物を乳鉢中で粉砕することによって製造した。この混合物の試料を、石英のU字管リアクターに投入して、窒素中、100〜250℃の所定の温度に加熱した。所望の温度に到達後、500ppmのNH3をそのガス流に5時間かけて添加した。この処理の後、窒素中で160℃に冷却し、そしてその粉末混合物を、N2中に500ppmのNO、533ppmのNH3、5体積%のH2O、10体積%のO2を含有するガス雰囲気に曝し、そして、材料のSCR活性に関する記録として、2700Nl/触媒1g時間の空間速度でNOxの変換率を測定することによって、得られた材料の触媒活性を測定した。次いで、反応温度を180及び200℃に高め、そしてそれぞれの温度におけるNOx変換率を同じ条件下で測定した。
Claims (12)
- 金属交換された結晶性マイクロポラスのメタロアルミノホスフェート又は金属交換された結晶性マイクロポラスのメタロアルミノホスフェートを含有する混合物の製造方法であって、
a)イオン交換能を示す一種又は二種以上のメタロアルミノホスフェート出発材料、及びb)一種又は二種以上の金属化合物
を含有する乾燥混合物を提供する工程;
アンモニアを含有するガス雰囲気中で、該金属化合物のイオン及び該結晶性マイクロポラスの材料のイオンの固体イオン交換を開始させ、かつ、遂行するのに100℃〜250℃の温度で、かつ、十分な時間該混合物を加熱する工程;及び
金属交換された結晶性マイクロポラスのメタロアルミノホスフェート材料又は金属交換された結晶性マイクロポラスのメタロアルミノホスフェート材料を含有する混合物を得る工程、
を含み、
前記一種又は二種以上の金属化合物が、酸化Cu(I)及び/又は酸化Cu(II)である上記の方法。 - 前記一種又は二種以上のメタロアルミノホスフェート出発材料が、ケイ素、チタン、スズ、亜鉛、マグネシウム、マンガン、コバルト又は鉄の群から選択される一種又は二種以上の金属を含有する、請求項1に記載の方法。
- 前記一種又は二種以上のメタロアルミノホスフェート出発材料が、CHA、AEI、AFI、AEL、AST、AFR、AFO及びFAUの群から選択されるフレームワークコードを有する、請求項1又は2に記載の方法。
- 前記一種又は二種以上のメタロアルミノホスフェート出発材料が、SAPO−34、SAPO−44、SAPO−18又はそれらの組合せの群から選択される、請求項1〜3のいずれか一つに記載の方法。
- 前記一種又は二種以上のマイクロポラスのメタロアルミノホスフェート出発材料が、H+又はNH4 +の形態にある、請求項1〜4のいずれか一つに記載の方法。
- 前記一種又は二種以上のマイクロポラスのメタロアルミノホスフェート出発材料が、有機構造指向剤を含有する、請求項1〜5のいずれか一つに記載の方法。
- 前記雰囲気中のアンモニアの含有量が、1〜5000体積ppmである、請求項1〜6のいずれか一つに記載の方法。
- 酸素が10体積%以下の量で前記雰囲気中に含有されている、請求項1〜7のいずれか一つに記載の方法。
- 前記ガス雰囲気が、5体積%以下の水を含有している、請求項1〜8のいずれか一つに記載の方法。
- 請求項1〜9のいずれか一つに記載の方法によって得られた金属交換された結晶性マイクロポラスのメタロアルミノホスフェート材料又は金属交換された結晶性マイクロポラスのメタロアルミノホスフェート材料の混合物を含む触媒に排ガスを接触させることを含む、還元剤による選択的接触還元によって該排ガスから窒素酸化物を除去する方法。
- 前記還元剤がアンモニア又はそれの前駆体である、請求項10に記載の方法。
- 前記還元剤が炭化水素を含む、請求項10に記載の方法。
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EP2463028A1 (en) * | 2010-12-11 | 2012-06-13 | Umicore Ag & Co. Kg | Process for the production of metal doped zeolites and zeotypes and application of same to the catalytic removal of nitrogen oxides |
US8956992B2 (en) | 2011-10-27 | 2015-02-17 | GM Global Technology Operations LLC | SCR catalysts preparation methods |
EP3129139B1 (en) * | 2014-04-07 | 2020-07-29 | Haldor Topsøe A/S | Method for producing metal exchanged zeolites by solid-state ion exchange at low temperatures |
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US20170113212A1 (en) | 2017-04-27 |
RU2016143401A3 (ja) | 2018-06-05 |
KR20160142326A (ko) | 2016-12-12 |
EP3129141A1 (en) | 2017-02-15 |
EP3129141B1 (en) | 2020-04-15 |
US9914114B2 (en) | 2018-03-13 |
WO2015154827A1 (en) | 2015-10-15 |
ZA201606133B (en) | 2019-02-27 |
CN106132541B (zh) | 2019-05-10 |
RU2016143401A (ru) | 2018-05-07 |
CA2945102C (en) | 2020-07-21 |
KR102226089B1 (ko) | 2021-03-11 |
CA2945102A1 (en) | 2015-10-15 |
RU2672095C2 (ru) | 2018-11-12 |
BR112016021428A2 (pt) | 2018-06-26 |
JP2017512744A (ja) | 2017-05-25 |
BR112016021428B1 (pt) | 2022-03-03 |
CN106132541A (zh) | 2016-11-16 |
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