CN101723877B - 吡啶碱催化加氢制备哌啶类化合物的方法 - Google Patents
吡啶碱催化加氢制备哌啶类化合物的方法 Download PDFInfo
- Publication number
- CN101723877B CN101723877B CN2009102343289A CN200910234328A CN101723877B CN 101723877 B CN101723877 B CN 101723877B CN 2009102343289 A CN2009102343289 A CN 2009102343289A CN 200910234328 A CN200910234328 A CN 200910234328A CN 101723877 B CN101723877 B CN 101723877B
- Authority
- CN
- China
- Prior art keywords
- nickel
- catalytic hydrogenation
- piperidines
- pyridine
- pyridine base
- 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.)
- Active
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 77
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 18
- -1 piperidines compound Chemical class 0.000 title claims abstract description 13
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 50
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 17
- 239000005995 Aluminium silicate Substances 0.000 claims abstract description 13
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 claims abstract description 13
- 235000012211 aluminium silicate Nutrition 0.000 claims abstract description 13
- 229910000323 aluminium silicate Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000003053 piperidines Chemical class 0.000 claims description 26
- 150000002815 nickel Chemical class 0.000 claims description 19
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 17
- 238000011068 loading method Methods 0.000 abstract description 8
- 239000006227 byproduct Substances 0.000 abstract description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 5
- 238000009835 boiling Methods 0.000 abstract description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 229910052681 coesite Inorganic materials 0.000 abstract 1
- 229910052593 corundum Inorganic materials 0.000 abstract 1
- 229910052906 cristobalite Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 229910052682 stishovite Inorganic materials 0.000 abstract 1
- 229910052905 tridymite Inorganic materials 0.000 abstract 1
- 229910001845 yogo sapphire Inorganic materials 0.000 abstract 1
- 230000009466 transformation Effects 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-Lutidine Substances CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 11
- 239000007868 Raney catalyst Substances 0.000 description 8
- 229910000564 Raney nickel Inorganic materials 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 6
- MFEIKQPHQINPRI-UHFFFAOYSA-N 3-Ethylpyridine Chemical compound CCC1=CC=CN=C1 MFEIKQPHQINPRI-UHFFFAOYSA-N 0.000 description 6
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 6
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical class CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 5
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 4
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229910052707 ruthenium Inorganic materials 0.000 description 4
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 3
- VJXRKZJMGVSXPX-UHFFFAOYSA-N 4-ethylpyridine Chemical compound CCC1=CC=NC=C1 VJXRKZJMGVSXPX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 238000004904 shortening Methods 0.000 description 3
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- QBBKKFZGCDJDQK-UHFFFAOYSA-N 2-ethylpiperidine Chemical compound CCC1CCCCN1 QBBKKFZGCDJDQK-UHFFFAOYSA-N 0.000 description 2
- YLUDSYGJHAQGOD-UHFFFAOYSA-N 3-ethylpiperidine Chemical compound CCC1CCCNC1 YLUDSYGJHAQGOD-UHFFFAOYSA-N 0.000 description 2
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 description 2
- PUACTIIESPYWSI-UHFFFAOYSA-N 3-propan-2-ylpyridine Chemical compound CC(C)C1=CC=CN=C1 PUACTIIESPYWSI-UHFFFAOYSA-N 0.000 description 2
- KNCHDRLWPAKSII-UHFFFAOYSA-N 4-ethyl-2-methylpyridine Chemical compound CCC1=CC=NC(C)=C1 KNCHDRLWPAKSII-UHFFFAOYSA-N 0.000 description 2
- KWHPWBXOLZTZMJ-UHFFFAOYSA-N 4-ethylpiperidine Chemical compound CCC1CCNCC1 KWHPWBXOLZTZMJ-UHFFFAOYSA-N 0.000 description 2
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000010970 precious metal Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- QWCDTIOGQKLNHC-UHFFFAOYSA-N 2,3,5-trimethylpiperidine Chemical compound CC1CNC(C)C(C)C1 QWCDTIOGQKLNHC-UHFFFAOYSA-N 0.000 description 1
- SSYMEDLFSXCTDQ-UHFFFAOYSA-N 2,3,5-trimethylpyridine Chemical compound CC1=C=NC(C)=C(C)[CH]1 SSYMEDLFSXCTDQ-UHFFFAOYSA-N 0.000 description 1
- DRLFSUDDXLQHJT-UHFFFAOYSA-N 2,3-dimethylpiperidine Chemical compound CC1CCCNC1C DRLFSUDDXLQHJT-UHFFFAOYSA-N 0.000 description 1
- QOZOFODNIBQPGN-UHFFFAOYSA-N 2,4-dimethylpiperidine Chemical compound CC1CCNC(C)C1 QOZOFODNIBQPGN-UHFFFAOYSA-N 0.000 description 1
- ICBFNPPCXPMCBP-UHFFFAOYSA-N 2,5-dimethylpiperidine Chemical compound CC1CCC(C)NC1 ICBFNPPCXPMCBP-UHFFFAOYSA-N 0.000 description 1
- SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- PFYPDUUXDADWKC-UHFFFAOYSA-N 2-propan-2-ylpyridine Chemical compound CC(C)C1=CC=CC=N1 PFYPDUUXDADWKC-UHFFFAOYSA-N 0.000 description 1
- YNKUJUOSWZNSJW-UHFFFAOYSA-N 3,4-dimethylpiperidine Chemical compound CC1CCNCC1C YNKUJUOSWZNSJW-UHFFFAOYSA-N 0.000 description 1
- IDWRJRPUIXRFRX-UHFFFAOYSA-N 3,5-dimethylpiperidine Chemical compound CC1CNCC(C)C1 IDWRJRPUIXRFRX-UHFFFAOYSA-N 0.000 description 1
- DEXCGKLNLMGYEG-UHFFFAOYSA-N 3-ethyl-2-methylpiperidine Chemical compound CCC1CCCNC1C DEXCGKLNLMGYEG-UHFFFAOYSA-N 0.000 description 1
- ZZKDGABMFBCSRP-UHFFFAOYSA-N 3-ethyl-2-methylpyridine Chemical compound CCC1=CC=CN=C1C ZZKDGABMFBCSRP-UHFFFAOYSA-N 0.000 description 1
- OGQRYSIZUFPQLJ-UHFFFAOYSA-N 4-ethyl-2-methylpiperidine Chemical compound CCC1CCNC(C)C1 OGQRYSIZUFPQLJ-UHFFFAOYSA-N 0.000 description 1
- XDOCILGWSIZBKG-UHFFFAOYSA-N 4-ethyl-3-methylpiperidine Chemical compound CCC1CCNCC1C XDOCILGWSIZBKG-UHFFFAOYSA-N 0.000 description 1
- NJQZTGGQYUUYKS-UHFFFAOYSA-N 4-ethyl-3-methylpyridine Chemical compound CCC1=CC=NC=C1C NJQZTGGQYUUYKS-UHFFFAOYSA-N 0.000 description 1
- FRGXNJWEDDQLFH-UHFFFAOYSA-N 4-propan-2-ylpyridine Chemical compound CC(C)C1=CC=NC=C1 FRGXNJWEDDQLFH-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- AOPCKOPZYFFEDA-UHFFFAOYSA-N nickel(2+);dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O AOPCKOPZYFFEDA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Catalysts (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009102343289A CN101723877B (zh) | 2009-11-24 | 2009-11-24 | 吡啶碱催化加氢制备哌啶类化合物的方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009102343289A CN101723877B (zh) | 2009-11-24 | 2009-11-24 | 吡啶碱催化加氢制备哌啶类化合物的方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101723877A CN101723877A (zh) | 2010-06-09 |
CN101723877B true CN101723877B (zh) | 2011-10-05 |
Family
ID=42445505
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2009102343289A Active CN101723877B (zh) | 2009-11-24 | 2009-11-24 | 吡啶碱催化加氢制备哌啶类化合物的方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101723877B (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105985300B (zh) * | 2015-02-09 | 2019-09-06 | 山东昆达生物科技有限公司 | 一种哌啶的连续生产方法 |
GB201810449D0 (en) * | 2018-06-26 | 2018-08-08 | Johnson Matthey Plc | Hydrogenation process |
CN113264867A (zh) * | 2021-06-08 | 2021-08-17 | 安徽星宇化工有限公司 | 一种顺式2,6-二甲基哌啶的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1198155A (zh) * | 1996-07-22 | 1998-11-04 | 广荣化学工业株式会社 | 哌啶的制备方法 |
CN1322715A (zh) * | 2000-05-08 | 2001-11-21 | 拜尔公司 | 哌啶化合物的制备方法 |
-
2009
- 2009-11-24 CN CN2009102343289A patent/CN101723877B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1198155A (zh) * | 1996-07-22 | 1998-11-04 | 广荣化学工业株式会社 | 哌啶的制备方法 |
CN1322715A (zh) * | 2000-05-08 | 2001-11-21 | 拜尔公司 | 哌啶化合物的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN101723877A (zh) | 2010-06-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN106365995B (zh) | 一种乙酸甲酯的生产方法 | |
CN101613274B (zh) | 一种二甲醚羰基化制备乙酸甲酯的方法 | |
CN103785408B (zh) | 一种草酸二甲酯加氢制备乙醇酸甲酯的催化剂及合成方法 | |
CN105130746A (zh) | 一种呋喃衍生物选择氢解制戊二醇的方法 | |
CN108620127B (zh) | 一种四氢糠醇氢解制1,5-戊二醇的催化剂及制备方法及其应用 | |
CN105921166A (zh) | 一种用于烷烃催化脱氢的介孔分子筛催化剂及其制备方法和应用 | |
CN110961110B (zh) | 催化剂及其在2,3,6-三氯吡啶加氢脱氯中的用途 | |
CN104998659A (zh) | 一种用于催化糠醛或糠醇重排加氢制备环戊醇的催化剂及其制备方法和应用方法 | |
CN105399705B (zh) | 一种利用氢转移反应制备糠醇的方法 | |
CN103864549B (zh) | 一种制备二苯甲酮类化合物的方法 | |
CN115709072B (zh) | 一种催化甲醇羰基化制乙酸的催化剂及其制备方法与应用 | |
CN101723877B (zh) | 吡啶碱催化加氢制备哌啶类化合物的方法 | |
CN113996337A (zh) | 一种催化高碳氢比合成气制乙酸的催化剂及其制备方法与应用 | |
CN106582666B (zh) | γ-戊内酯加氢催化剂、制备方法及用于制备1,4-戊二醇和2-甲基四氢呋喃的方法 | |
CN102863335B (zh) | 一种丁二酸二酯的制备方法 | |
CN102580754A (zh) | 一种合成醋酸甲酯的催化剂及制法和应用 | |
CN109574798A (zh) | 一种合成气直接生产乙醇的方法 | |
CN106268806A (zh) | 一种甲醇羰基化的催化剂及其制备和应用 | |
CN106518619B (zh) | 一种醋酸酯加氢制备乙醇的方法 | |
CN106518657B (zh) | 一种通过甲醇羰基化制备乙酸的方法 | |
CN103848720B (zh) | 一种制备乙二醇的方法 | |
CN110252408A (zh) | 一种具有CUS的MOF-808(Zr)组装纳米金属催化剂、制备及应用 | |
WO2017012244A1 (zh) | 一种低级脂肪羧酸烷基酯的生产方法 | |
CN101314134A (zh) | 由合成气直接制备二甲醚的双功能催化剂的制备方法 | |
CN111036198A (zh) | 双壳核壳结构金属催化剂及其制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: NANJING RED SUN BIOCHEMICAL CO., LTD. Free format text: FORMER OWNER: NANJING FIRST PESTICIDE GROUP CO., LTD. Effective date: 20110921 |
|
C41 | Transfer of patent application or patent right or utility model | ||
COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 211300 NANJING, JIANGSU PROVINCE TO: 210047 NANJING, JIANGSU PROVINCE |
|
TA01 | Transfer of patent application right |
Effective date of registration: 20110921 Address after: 210047 Nanjing Chemical Industrial Park, Jiangsu aromatic South Road, No. 168 Applicant after: Nanjing Red Sun Biological Chemical Co., Ltd. Address before: 211300 Pagoda Road 269, Gaochun County, Jiangsu, Nanjing Applicant before: Nanjing First Pesticide Group Co., Ltd. |
|
TR01 | Transfer of patent right |
Effective date of registration: 20180517 Address after: 210047 No. 168 aromatics South Road, Nanjing chemical industry park, Jiangsu Co-patentee after: Nanjing Redsun Co., Ltd. Patentee after: Nanjing Red Sun Biological Chemical Co., Ltd. Address before: 210047 No. 168 aromatics South Road, Nanjing chemical industry park, Jiangsu Patentee before: Nanjing Red Sun Biological Chemical Co., Ltd. |
|
TR01 | Transfer of patent right |