CN104477933A - 一种硅烷化改性分子筛的制备方法 - Google Patents
一种硅烷化改性分子筛的制备方法 Download PDFInfo
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- CN104477933A CN104477933A CN201410707091.2A CN201410707091A CN104477933A CN 104477933 A CN104477933 A CN 104477933A CN 201410707091 A CN201410707091 A CN 201410707091A CN 104477933 A CN104477933 A CN 104477933A
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- Prior art keywords
- molecular sieve
- silylating reagent
- preparation
- silanization
- acid
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- 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.)
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical class [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 title claims abstract description 143
- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 160
- 239000002808 molecular sieve Substances 0.000 claims abstract description 139
- 238000000034 method Methods 0.000 claims abstract description 71
- 238000002444 silanisation Methods 0.000 claims abstract description 53
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000003960 organic solvent Substances 0.000 claims abstract description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
- 238000001035 drying Methods 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 32
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- 238000002203 pretreatment Methods 0.000 claims description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 21
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 18
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 17
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 claims description 16
- 239000005051 trimethylchlorosilane Substances 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 13
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 12
- 230000008859 change Effects 0.000 claims description 12
- 239000005046 Chlorosilane Substances 0.000 claims description 11
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims description 11
- 150000007524 organic acids Chemical class 0.000 claims description 10
- 150000007530 organic bases Chemical class 0.000 claims description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 9
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 9
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 claims description 9
- 235000006408 oxalic acid Nutrition 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 5
- GJWAPAVRQYYSTK-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)amino]-dimethylsilicon Chemical compound C[Si](C)N[Si](C)C GJWAPAVRQYYSTK-UHFFFAOYSA-N 0.000 claims description 5
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 claims description 5
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims description 5
- 229940095064 tartrate Drugs 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 claims description 4
- MHRNQQUEUYMEEH-UHFFFAOYSA-N [[[ethyl(dimethyl)silyl]amino]-dimethylsilyl]ethane Chemical compound CC[Si](C)(C)N[Si](C)(C)CC MHRNQQUEUYMEEH-UHFFFAOYSA-N 0.000 claims description 4
- KWYZNESIGBQHJK-UHFFFAOYSA-N chloro-dimethyl-phenylsilane Chemical compound C[Si](C)(Cl)C1=CC=CC=C1 KWYZNESIGBQHJK-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 239000005055 methyl trichlorosilane Substances 0.000 claims description 4
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000001384 succinic acid Substances 0.000 claims description 4
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 2
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 1
- 239000011148 porous material Substances 0.000 abstract description 11
- 238000012986 modification Methods 0.000 abstract description 9
- 230000004048 modification Effects 0.000 abstract description 8
- 238000005406 washing Methods 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract description 2
- 230000001681 protective effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- 238000001179 sorption measurement Methods 0.000 description 55
- 230000003068 static effect Effects 0.000 description 49
- 230000000052 comparative effect Effects 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000000274 adsorptive effect Effects 0.000 description 8
- 230000002209 hydrophobic effect Effects 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 150000003857 carboxamides Chemical class 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 229960004132 diethyl ether Drugs 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000006884 silylation reaction Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910002808 Si–O–Si Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- IKXDEFIEGAVNOZ-UHFFFAOYSA-N [SiH4].[C] Chemical group [SiH4].[C] IKXDEFIEGAVNOZ-UHFFFAOYSA-N 0.000 description 1
- UGACIEPFGXRWCH-UHFFFAOYSA-N [Si].[Ti] Chemical compound [Si].[Ti] UGACIEPFGXRWCH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000005260 alpha ray Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000003837 high-temperature calcination Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000007781 pre-processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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Abstract
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Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105289517A (zh) * | 2015-12-10 | 2016-02-03 | 北京化工大学 | 一种适用于海水淡化的吸附材料及其制备方法 |
CN107519837A (zh) * | 2017-08-31 | 2017-12-29 | 长沙埃比林环保科技有限公司 | 一种微波制备废水重金属吸附材料的方法 |
CN107792862A (zh) * | 2017-10-25 | 2018-03-13 | 马鞍山拓锐金属表面技术有限公司 | 一种分子筛型重金属固化剂的制备方法 |
CN108002403A (zh) * | 2017-12-13 | 2018-05-08 | 卓悦环保新材料(上海)有限公司 | 一种cha分子筛的合成方法 |
CN110184120A (zh) * | 2019-05-20 | 2019-08-30 | 李科成 | 一种食用油脱酸用处理颗粒的制备方法 |
CN110627081A (zh) * | 2018-06-25 | 2019-12-31 | 中国石油化工股份有限公司 | 一种氨基功能化sba分子筛的制备方法及其应用 |
CN110627090A (zh) * | 2018-06-25 | 2019-12-31 | 中国石油化工股份有限公司 | 一种巯基功能化sba分子筛的制备方法及其应用 |
CN111004820A (zh) * | 2019-12-22 | 2020-04-14 | 河南金丹乳酸科技股份有限公司 | 发酵生产乳酸用中和剂的制备方法 |
US10647586B2 (en) | 2018-01-03 | 2020-05-12 | Petrochina Company Limited | Amphiphilic molecular sieve containing lipophilic group on the outside and hydrophilic group on the inside and production method thereof |
US10759667B2 (en) | 2018-01-03 | 2020-09-01 | Petrochina Company Limited | Amphiphilic molecular sieve containing hydrophilic group on the outside and lipophilic group on the inside and production method threof |
CN111960432A (zh) * | 2020-08-20 | 2020-11-20 | 株洲市陕研新材料装备技术研究院有限公司 | 一种分子筛的制备方法、分子筛及纳米多孔能量吸收材料 |
CN113304786A (zh) * | 2020-02-27 | 2021-08-27 | 中国石油化工股份有限公司 | 含有二氯二甲基硅烷改性全硅介孔材料的催化裂化助剂及其制备方法和应用 |
CN113318718A (zh) * | 2020-02-28 | 2021-08-31 | 中国石油化工股份有限公司 | 含有二氯二甲基硅烷改性棒状介孔材料的碳四烯烃裂解增产丙烯催化剂及其制备方法和应用 |
CN114853027A (zh) * | 2022-05-05 | 2022-08-05 | 山东华鲁恒升化工股份有限公司 | 多孔钛硅分子筛、改性钛硅分子筛、改性分子筛及其制备方法和应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103787351A (zh) * | 2014-01-27 | 2014-05-14 | 华东师范大学 | 一种具有不同拓扑结构的微孔沸石分子筛的制备方法 |
-
2014
- 2014-11-27 CN CN201410707091.2A patent/CN104477933B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103787351A (zh) * | 2014-01-27 | 2014-05-14 | 华东师范大学 | 一种具有不同拓扑结构的微孔沸石分子筛的制备方法 |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105289517A (zh) * | 2015-12-10 | 2016-02-03 | 北京化工大学 | 一种适用于海水淡化的吸附材料及其制备方法 |
CN107519837A (zh) * | 2017-08-31 | 2017-12-29 | 长沙埃比林环保科技有限公司 | 一种微波制备废水重金属吸附材料的方法 |
CN107792862A (zh) * | 2017-10-25 | 2018-03-13 | 马鞍山拓锐金属表面技术有限公司 | 一种分子筛型重金属固化剂的制备方法 |
CN108002403A (zh) * | 2017-12-13 | 2018-05-08 | 卓悦环保新材料(上海)有限公司 | 一种cha分子筛的合成方法 |
US10647586B2 (en) | 2018-01-03 | 2020-05-12 | Petrochina Company Limited | Amphiphilic molecular sieve containing lipophilic group on the outside and hydrophilic group on the inside and production method thereof |
US10759667B2 (en) | 2018-01-03 | 2020-09-01 | Petrochina Company Limited | Amphiphilic molecular sieve containing hydrophilic group on the outside and lipophilic group on the inside and production method threof |
CN110627081A (zh) * | 2018-06-25 | 2019-12-31 | 中国石油化工股份有限公司 | 一种氨基功能化sba分子筛的制备方法及其应用 |
CN110627090A (zh) * | 2018-06-25 | 2019-12-31 | 中国石油化工股份有限公司 | 一种巯基功能化sba分子筛的制备方法及其应用 |
CN110184120A (zh) * | 2019-05-20 | 2019-08-30 | 李科成 | 一种食用油脱酸用处理颗粒的制备方法 |
CN111004820A (zh) * | 2019-12-22 | 2020-04-14 | 河南金丹乳酸科技股份有限公司 | 发酵生产乳酸用中和剂的制备方法 |
CN113304786A (zh) * | 2020-02-27 | 2021-08-27 | 中国石油化工股份有限公司 | 含有二氯二甲基硅烷改性全硅介孔材料的催化裂化助剂及其制备方法和应用 |
CN113304786B (zh) * | 2020-02-27 | 2023-05-30 | 中国石油化工股份有限公司 | 含有二氯二甲基硅烷改性全硅介孔材料的催化裂化助剂及其制备方法和应用 |
CN113318718A (zh) * | 2020-02-28 | 2021-08-31 | 中国石油化工股份有限公司 | 含有二氯二甲基硅烷改性棒状介孔材料的碳四烯烃裂解增产丙烯催化剂及其制备方法和应用 |
CN113318718B (zh) * | 2020-02-28 | 2023-05-09 | 中国石油化工股份有限公司 | 含有二氯二甲基硅烷改性棒状介孔材料的碳四烯烃裂解增产丙烯催化剂及其制备方法和应用 |
CN111960432A (zh) * | 2020-08-20 | 2020-11-20 | 株洲市陕研新材料装备技术研究院有限公司 | 一种分子筛的制备方法、分子筛及纳米多孔能量吸收材料 |
CN114853027A (zh) * | 2022-05-05 | 2022-08-05 | 山东华鲁恒升化工股份有限公司 | 多孔钛硅分子筛、改性钛硅分子筛、改性分子筛及其制备方法和应用 |
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