CN1269343A - Catalytic oxidation process of alkane and naphthene hydrocarbon - Google Patents
Catalytic oxidation process of alkane and naphthene hydrocarbon Download PDFInfo
- Publication number
- CN1269343A CN1269343A CN 00113225 CN00113225A CN1269343A CN 1269343 A CN1269343 A CN 1269343A CN 00113225 CN00113225 CN 00113225 CN 00113225 A CN00113225 A CN 00113225A CN 1269343 A CN1269343 A CN 1269343A
- Authority
- CN
- China
- Prior art keywords
- metalloporphyrin
- catalyst
- alkane
- hydrocarbon
- catalyzer
- Prior art date
- 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.)
- Granted
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- 230000003647 oxidation Effects 0.000 title claims abstract description 19
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 19
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 11
- -1 naphthene hydrocarbon Chemical class 0.000 title claims abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 15
- 229930195733 hydrocarbon Natural products 0.000 title claims description 15
- 150000001335 aliphatic alkanes Chemical class 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 150000004032 porphyrins Chemical class 0.000 claims abstract description 11
- 229910052751 metal Inorganic materials 0.000 claims abstract description 9
- 239000002184 metal Substances 0.000 claims abstract description 9
- 239000003426 co-catalyst Substances 0.000 claims abstract description 5
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229920000858 Cyclodextrin Polymers 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 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
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 4
- 150000002602 lanthanoids Chemical class 0.000 claims description 4
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 4
- 239000004800 polyvinyl chloride Substances 0.000 claims description 4
- 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 4
- 239000004113 Sepiolite Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052624 sepiolite Inorganic materials 0.000 claims description 3
- 235000019355 sepiolite Nutrition 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- DUKURNFHYQXCJG-UHFFFAOYSA-N Lewis A pentasaccharide Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(C)=O)C(OC2C(C(OC3C(OC(O)C(O)C3O)CO)OC(CO)C2O)O)OC1CO DUKURNFHYQXCJG-UHFFFAOYSA-N 0.000 claims description 2
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims description 2
- 239000004793 Polystyrene 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
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 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
- 239000008103 glucose Substances 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 229950006780 n-acetylglucosamine Drugs 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
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 150000005838 radical anions Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 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
- 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
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 26
- 238000006555 catalytic reaction Methods 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 230000005587 bubbling Effects 0.000 description 3
- HTSABYAWKQAHBT-UHFFFAOYSA-N 3-methylcyclohexanol Chemical compound CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- NDVWOBYBJYUSMF-UHFFFAOYSA-N 2-methylcyclohexan-1-ol Chemical compound CC1CCCCC1O NDVWOBYBJYUSMF-UHFFFAOYSA-N 0.000 description 1
- KDPMIBMNNGCWTF-UHFFFAOYSA-N C(CCC)O.CC1(CC(C(=O)O)=CC=C1)C(=O)O Chemical group C(CCC)O.CC1(CC(C(=O)O)=CC=C1)C(=O)O KDPMIBMNNGCWTF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 00113225 CN1116258C (en) | 2000-01-17 | 2000-01-17 | Catalytic oxidation process of alkane and naphthene hydrocarbon |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 00113225 CN1116258C (en) | 2000-01-17 | 2000-01-17 | Catalytic oxidation process of alkane and naphthene hydrocarbon |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1269343A true CN1269343A (en) | 2000-10-11 |
CN1116258C CN1116258C (en) | 2003-07-30 |
Family
ID=4583031
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 00113225 Expired - Fee Related CN1116258C (en) | 2000-01-17 | 2000-01-17 | Catalytic oxidation process of alkane and naphthene hydrocarbon |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1116258C (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006036642A (en) * | 2004-07-22 | 2006-02-09 | Sumitomo Chemical Co Ltd | Method for producing cycloalkanol and/or cycloalkanone |
CN100379715C (en) * | 2006-04-11 | 2008-04-09 | 湖南大学 | Process for preparation of carboxylic acid esters |
CN100402477C (en) * | 2003-03-14 | 2008-07-16 | 湖南大学 | Method for catalytic conversion of alkyl cyclohexanol and alkyl cyclohexanone from air oxidized alkyl cyclohexane |
CN103922903A (en) * | 2014-04-01 | 2014-07-16 | 湖南大学 | Method for catalytically oxidizing alkane and cycloparaffin by use of conjugated polymetalloporphyrin |
CN106391123A (en) * | 2016-08-17 | 2017-02-15 | 巨化集团技术中心 | A catalyst used for cyclohexane catalytic oxidation and a using method thereof |
CN109833912A (en) * | 2019-03-21 | 2019-06-04 | 南京工业大学 | Metalloporphyrin-loaded titanium silicalite molecular sieve novel catalyst and synthesis method thereof |
CN110526801A (en) * | 2019-08-28 | 2019-12-03 | 浙江工业大学 | Method for oxidizing cycloalkane by cobalt (II) porphyrin/copper (II) porphyrin salt concerted catalysis |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103254060B (en) * | 2013-04-16 | 2015-04-15 | 衢州群颖化学科技有限公司 | Method for preparing adipic acid through co-catalytic oxidation of six-carbon oxygenated compound and cyclohexane |
-
2000
- 2000-01-17 CN CN 00113225 patent/CN1116258C/en not_active Expired - Fee Related
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100402477C (en) * | 2003-03-14 | 2008-07-16 | 湖南大学 | Method for catalytic conversion of alkyl cyclohexanol and alkyl cyclohexanone from air oxidized alkyl cyclohexane |
JP2006036642A (en) * | 2004-07-22 | 2006-02-09 | Sumitomo Chemical Co Ltd | Method for producing cycloalkanol and/or cycloalkanone |
US7632942B2 (en) | 2004-07-22 | 2009-12-15 | Sumitomo Chemical Company, Limited | Process for producing cycloalkanol and/or cycloalkanone |
CN1740127B (en) * | 2004-07-22 | 2012-01-04 | 住友化学株式会社 | Process for producing cycloalkanol and/or cycloalkanone |
CN100379715C (en) * | 2006-04-11 | 2008-04-09 | 湖南大学 | Process for preparation of carboxylic acid esters |
CN103922903A (en) * | 2014-04-01 | 2014-07-16 | 湖南大学 | Method for catalytically oxidizing alkane and cycloparaffin by use of conjugated polymetalloporphyrin |
CN103922903B (en) * | 2014-04-01 | 2016-03-30 | 湖南大学 | By the method for conjugated polymers catalysis of metalloporphyrin oxidation of alkanes and naphthenic hydrocarbon |
CN106391123A (en) * | 2016-08-17 | 2017-02-15 | 巨化集团技术中心 | A catalyst used for cyclohexane catalytic oxidation and a using method thereof |
CN106391123B (en) * | 2016-08-17 | 2019-03-29 | 巨化集团技术中心 | A kind of catalyst and its application method for catalytic oxidation of cyclohexane |
CN109833912A (en) * | 2019-03-21 | 2019-06-04 | 南京工业大学 | Metalloporphyrin-loaded titanium silicalite molecular sieve novel catalyst and synthesis method thereof |
CN110526801A (en) * | 2019-08-28 | 2019-12-03 | 浙江工业大学 | Method for oxidizing cycloalkane by cobalt (II) porphyrin/copper (II) porphyrin salt concerted catalysis |
Also Published As
Publication number | Publication date |
---|---|
CN1116258C (en) | 2003-07-30 |
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Legal Events
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SE01 | Entry into force of request for substantive examination | ||
C06 | Publication | ||
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C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: HUNAN UNIVERSITY Free format text: FORMER OWNER: GUO CANCHENG Effective date: 20040430 |
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C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20040430 Address after: 410082 Mount Yuelu, Hunan, Changsha Patentee after: Hunan University Address before: 410082 School of chemistry and chemical engineering, Hunan University, Changsha, Hunan Patentee before: Guo Cancheng |
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C17 | Cessation of patent right | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20030730 Termination date: 20100117 |