CN1405131A - 金属卟啉催化空气氧化环己烷的方法 - Google Patents
金属卟啉催化空气氧化环己烷的方法 Download PDFInfo
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- CN1405131A CN1405131A CN 02139709 CN02139709A CN1405131A CN 1405131 A CN1405131 A CN 1405131A CN 02139709 CN02139709 CN 02139709 CN 02139709 A CN02139709 A CN 02139709A CN 1405131 A CN1405131 A CN 1405131A
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- metalloporphyrin
- catalyst
- air
- cyclohexane
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 230000003647 oxidation Effects 0.000 title claims abstract description 25
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 17
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 229910052751 metal Inorganic materials 0.000 claims abstract description 14
- 239000002184 metal Substances 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 150000004032 porphyrins Chemical class 0.000 claims abstract description 12
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 7
- -1 transition metal salt Chemical class 0.000 claims abstract description 7
- 239000003426 co-catalyst Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000003147 glycosyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 4
- 239000004800 polyvinyl chloride Substances 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 229920000858 Cyclodextrin Polymers 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 239000004113 Sepiolite Substances 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910021536 Zeolite Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052624 sepiolite Inorganic materials 0.000 claims description 2
- 235000019355 sepiolite Nutrition 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 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 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000003624 transition metals Chemical group 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract description 19
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract description 13
- 102000004190 Enzymes Human genes 0.000 abstract description 2
- 108090000790 Enzymes Proteins 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 1
- 238000007210 heterogeneous catalysis Methods 0.000 abstract 1
- 238000007172 homogeneous catalysis Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- NVJHHSJKESILSZ-UHFFFAOYSA-N [Co].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound [Co].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 NVJHHSJKESILSZ-UHFFFAOYSA-N 0.000 description 1
- JQRLYSGCPHSLJI-UHFFFAOYSA-N [Fe].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound [Fe].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JQRLYSGCPHSLJI-UHFFFAOYSA-N 0.000 description 1
- RFNGIZVFDKCRMZ-UHFFFAOYSA-N [Sb].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound [Sb].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RFNGIZVFDKCRMZ-UHFFFAOYSA-N 0.000 description 1
- SINKQSZYJSQJHN-UHFFFAOYSA-N [Sn].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound [Sn].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 SINKQSZYJSQJHN-UHFFFAOYSA-N 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
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CNB021397090A CN1191218C (zh) | 2002-10-29 | 2002-10-29 | 金属卟啉催化空气氧化环己烷的方法 |
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Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006036642A (ja) * | 2004-07-22 | 2006-02-09 | Sumitomo Chemical Co Ltd | シクロアルカノール及び/又はシクロアルカノンの製造方法 |
CN100393680C (zh) * | 2006-05-22 | 2008-06-11 | 湖南大学 | 环己烷空气氧化制备环己醇、环己酮和己二酸的工艺及设备 |
CN101870703A (zh) * | 2010-03-05 | 2010-10-27 | 南京理工大学 | 联二硫丙基卟啉及其金属络合物、制备方法和应用 |
CN102391238A (zh) * | 2011-09-28 | 2012-03-28 | 江苏飞翔化工股份有限公司 | 一种催化环己酮氧化制备ε-己内酯的方法 |
CN101367709B (zh) * | 2008-09-22 | 2012-04-25 | 广西大学 | 超细a1ooh固载金属卟啉催化空气氧化环己烷的方法 |
CN103755521A (zh) * | 2014-01-26 | 2014-04-30 | 沅江华龙催化科技有限公司 | 基于气液固多相反应分离同步反应器利用空气氧化环己烷生产ka油的方法 |
CN106000468A (zh) * | 2016-06-01 | 2016-10-12 | 中山大学惠州研究院 | 一种金属卟啉-无机晶体复合微球及其制备方法 |
CN109876857A (zh) * | 2019-03-21 | 2019-06-14 | 南京工业大学 | 一种利用金属卟啉负载的钛硅分子筛在微通道中催化丙烯环氧化的方法 |
CN110526801A (zh) * | 2019-08-28 | 2019-12-03 | 浙江工业大学 | 卟啉钴(ii)/铜(ii)盐协同催化氧化环烷烃的方法 |
CN110563555A (zh) * | 2019-08-28 | 2019-12-13 | 浙江工业大学 | 一种卟啉钴(ii)/锌(ii)盐协同催化氧化环烷烃的方法 |
CN110918122A (zh) * | 2019-11-26 | 2020-03-27 | 浙江工业大学 | 一种非均相铜卟啉及其制备方法和应用 |
CN111943810A (zh) * | 2020-08-29 | 2020-11-17 | 浙江工业大学 | 一种限域性金属卟啉锰(II)/Cu(II)盐协同催化氧化环烷烃的方法 |
CN111995506A (zh) * | 2020-08-31 | 2020-11-27 | 浙江工业大学 | 一种限域性金属卟啉锰(II)/Zn(II)盐协同催化氧化环烷烃的方法 |
CN112094179A (zh) * | 2020-08-31 | 2020-12-18 | 浙江工业大学 | 一种双金属卟啉MOFs PCN-224(Co&Cu)催化氧化环烷烃的方法 |
CN113769781A (zh) * | 2020-06-10 | 2021-12-10 | 北京化工大学 | 一种含共价有机框架聚合物材料催化剂及其制备方法和应用以及一种催化氧化烷烃的方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100445255C (zh) * | 2007-04-21 | 2008-12-24 | 中国科学院新疆理化技术研究所 | 席夫碱-卟啉金属化合物催化氧化六碳环化合物的方法 |
-
2002
- 2002-10-29 CN CNB021397090A patent/CN1191218C/zh not_active Expired - Fee Related
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006036642A (ja) * | 2004-07-22 | 2006-02-09 | Sumitomo Chemical Co Ltd | シクロアルカノール及び/又はシクロアルカノンの製造方法 |
SG119369A1 (en) * | 2004-07-22 | 2006-02-28 | Sumitomo Chemical Co | Process for producing cycloalkanol and/or cycloalkanone |
CN100393680C (zh) * | 2006-05-22 | 2008-06-11 | 湖南大学 | 环己烷空气氧化制备环己醇、环己酮和己二酸的工艺及设备 |
CN101367709B (zh) * | 2008-09-22 | 2012-04-25 | 广西大学 | 超细a1ooh固载金属卟啉催化空气氧化环己烷的方法 |
CN101870703A (zh) * | 2010-03-05 | 2010-10-27 | 南京理工大学 | 联二硫丙基卟啉及其金属络合物、制备方法和应用 |
CN101870703B (zh) * | 2010-03-05 | 2012-05-23 | 南京理工大学 | 联二硫丙基卟啉及其金属络合物、制备方法和应用 |
CN102391238A (zh) * | 2011-09-28 | 2012-03-28 | 江苏飞翔化工股份有限公司 | 一种催化环己酮氧化制备ε-己内酯的方法 |
CN102391238B (zh) * | 2011-09-28 | 2013-07-03 | 江苏飞翔化工股份有限公司 | 一种催化环己酮氧化制备ε-己内酯的方法 |
CN103755521A (zh) * | 2014-01-26 | 2014-04-30 | 沅江华龙催化科技有限公司 | 基于气液固多相反应分离同步反应器利用空气氧化环己烷生产ka油的方法 |
CN103755521B (zh) * | 2014-01-26 | 2015-02-18 | 沅江华龙催化科技有限公司 | 基于气液固多相反应分离同步反应器利用空气氧化环己烷生产ka油的方法 |
CN106000468A (zh) * | 2016-06-01 | 2016-10-12 | 中山大学惠州研究院 | 一种金属卟啉-无机晶体复合微球及其制备方法 |
CN106000468B (zh) * | 2016-06-01 | 2019-04-19 | 中山大学惠州研究院 | 一种金属卟啉-无机晶体复合微球及其制备方法 |
CN109876857A (zh) * | 2019-03-21 | 2019-06-14 | 南京工业大学 | 一种利用金属卟啉负载的钛硅分子筛在微通道中催化丙烯环氧化的方法 |
CN110526801A (zh) * | 2019-08-28 | 2019-12-03 | 浙江工业大学 | 卟啉钴(ii)/铜(ii)盐协同催化氧化环烷烃的方法 |
CN110563555A (zh) * | 2019-08-28 | 2019-12-13 | 浙江工业大学 | 一种卟啉钴(ii)/锌(ii)盐协同催化氧化环烷烃的方法 |
CN110918122A (zh) * | 2019-11-26 | 2020-03-27 | 浙江工业大学 | 一种非均相铜卟啉及其制备方法和应用 |
CN113769781A (zh) * | 2020-06-10 | 2021-12-10 | 北京化工大学 | 一种含共价有机框架聚合物材料催化剂及其制备方法和应用以及一种催化氧化烷烃的方法 |
CN111943810A (zh) * | 2020-08-29 | 2020-11-17 | 浙江工业大学 | 一种限域性金属卟啉锰(II)/Cu(II)盐协同催化氧化环烷烃的方法 |
CN111995506A (zh) * | 2020-08-31 | 2020-11-27 | 浙江工业大学 | 一种限域性金属卟啉锰(II)/Zn(II)盐协同催化氧化环烷烃的方法 |
CN112094179A (zh) * | 2020-08-31 | 2020-12-18 | 浙江工业大学 | 一种双金属卟啉MOFs PCN-224(Co&Cu)催化氧化环烷烃的方法 |
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