CN101693211A - Transition metal catalyst and method for preparing picoline through adopting catalyst - Google Patents
Transition metal catalyst and method for preparing picoline through adopting catalyst Download PDFInfo
- Publication number
- CN101693211A CN101693211A CN 200910236478 CN200910236478A CN101693211A CN 101693211 A CN101693211 A CN 101693211A CN 200910236478 CN200910236478 CN 200910236478 CN 200910236478 A CN200910236478 A CN 200910236478A CN 101693211 A CN101693211 A CN 101693211A
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- CN
- China
- Prior art keywords
- catalyst
- picoline
- transition
- metal catalyst
- acetylene
- 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
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 72
- 229910052723 transition metal Inorganic materials 0.000 title claims abstract description 55
- 150000003624 transition metals Chemical class 0.000 title claims abstract description 54
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 73
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 25
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims abstract description 9
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims abstract description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 6
- -1 silicyl Chemical group 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical group [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 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000013078 crystal Substances 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000010183 spectrum analysis Methods 0.000 description 6
- 238000003828 vacuum filtration Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- NNSSHRACPMBEBC-UHFFFAOYSA-N sodium penta-1,3-diene Chemical compound [Na+].CC=CC=[CH-] NNSSHRACPMBEBC-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HHWFLQDBOJJRGU-UHFFFAOYSA-N Cl[SiH2]Cl.C(C)C=1C=CCC1 Chemical compound Cl[SiH2]Cl.C(C)C=1C=CCC1 HHWFLQDBOJJRGU-UHFFFAOYSA-N 0.000 description 1
- MDBWHBUZZKYRTQ-UHFFFAOYSA-N [SiH4].CC=1C=CCC1 Chemical class [SiH4].CC=1C=CCC1 MDBWHBUZZKYRTQ-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 1
- 229960003291 chlorphenamine Drugs 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000010977 jade Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- UDBORWKCIDLNIG-UHFFFAOYSA-N sodium;1h-inden-1-ide Chemical compound [Na+].C1=CC=C2[CH-]C=CC2=C1 UDBORWKCIDLNIG-UHFFFAOYSA-N 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
Transition-metal catalyst | The conversion ratio of acetonitrile (%) | The yield of 2-picoline (%) | |
Embodiment 8 | ??A1 | ??95.8 | ??91.6 |
Embodiment 9 | ??A2 | ??96.1 | ??92.1 |
Embodiment 10 | ??A3 | ??97.4 | ??93.5 |
Embodiment 11 | ??A4 | ??100 | ??95.9 |
Embodiment 12 | ??A5 | ??100 | ??98.4 |
Transition-metal catalyst | The conversion ratio of acetonitrile (%) | The yield of 2-picoline (%) | |
Embodiment 13 | ??A6 | ??99.5 | ??95.3 |
Embodiment 14 | ??A7 | ??72.8 | ??56.2 |
Comparative Examples 2 | ??D1 | ??68.1 | ??48.9 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200910236478 CN101693211B (en) | 2009-10-22 | 2009-10-22 | Transition metal catalyst and method for preparing picoline through adopting catalyst |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200910236478 CN101693211B (en) | 2009-10-22 | 2009-10-22 | Transition metal catalyst and method for preparing picoline through adopting catalyst |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101693211A true CN101693211A (en) | 2010-04-14 |
CN101693211B CN101693211B (en) | 2013-04-10 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN 200910236478 Active CN101693211B (en) | 2009-10-22 | 2009-10-22 | Transition metal catalyst and method for preparing picoline through adopting catalyst |
Country Status (1)
Country | Link |
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CN (1) | CN101693211B (en) |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005023892A1 (en) * | 2003-09-11 | 2005-03-17 | Basell Polyolefine Gmbh | Multistep process for preparing heterophasic propylene copolymers |
CN101108821B (en) * | 2007-08-15 | 2011-04-27 | 新乡市恒基化工有限公司 | Method of manufacturing 2-picoline |
-
2009
- 2009-10-22 CN CN 200910236478 patent/CN101693211B/en active Active
Also Published As
Publication number | Publication date |
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CN101693211B (en) | 2013-04-10 |
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Owner name: BEIJING NUTRICHEM INTERNATIONAL CO., LTD. Free format text: FORMER OWNER: BEIJING YINGTAI JIAHE SCIENCE AND TECHNOLOGY CO., LTD. Effective date: 20100928 |
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Effective date of registration: 20100928 Address after: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Applicant after: Nutrichem International Co., Ltd. Address before: 100085, Beijing, Haidian District on the road to open 5, Zhongguancun biological medicine Park 3 Applicant before: Nutrichem Laboratory Co., Ltd. Effective date of registration: 20100928 Address after: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Applicant after: Nutrichem International Co., Ltd. Address before: 100085, Beijing, Haidian District on the road to open 5, Zhongguancun biological medicine Park 3 Applicant before: Nutrichem Laboratory Co., Ltd. |
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Address after: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Applicant after: Nutrichem Co., Ltd. Address before: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Applicant before: Nutrichem International Co., Ltd. Address after: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Applicant after: Nutrichem Co., Ltd. Address before: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Applicant before: Nutrichem International Co., Ltd. |
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Address after: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Patentee after: BEIJING NUTRICHEM COMPANY LIMITED Address before: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Patentee before: Nutrichem Co., Ltd. Address after: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Patentee after: BEIJING NUTRICHEM COMPANY LIMITED Address before: 100192 Beijing, Haidian District West Road, No. 66, building D-1 Patentee before: Nutrichem Co., Ltd. |
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Effective date of registration: 20200515 Address after: 102206 floor 1-2, Zone D, building 1, No. 27, life Garden Road, science and Technology Park, Changping District, Beijing Patentee after: BEIJING YINGTAIJIAHE ANALYSIS TECHNOLOGY Co.,Ltd. Address before: 100192, building D-1, No. 66 Xiao Dong Road, Beijing, Haidian District Patentee before: BEIJING NUTRICHEM Co.,Ltd. |