CN101219988A - 一种4,4′-二取代基-2,2′-联吡啶的合成方法 - Google Patents
一种4,4′-二取代基-2,2′-联吡啶的合成方法 Download PDFInfo
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- CN101219988A CN101219988A CNA2008100562785A CN200810056278A CN101219988A CN 101219988 A CN101219988 A CN 101219988A CN A2008100562785 A CNA2008100562785 A CN A2008100562785A CN 200810056278 A CN200810056278 A CN 200810056278A CN 101219988 A CN101219988 A CN 101219988A
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- carbon atom
- dipyridyl
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- alkynyl
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- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 14
- 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 10
- 238000001816 cooling Methods 0.000 claims abstract description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000001953 recrystallisation Methods 0.000 claims abstract description 3
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
- 239000007789 gas Substances 0.000 claims description 18
- 239000000706 filtrate Substances 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 150000001721 carbon Chemical group 0.000 claims description 12
- 238000010189 synthetic method Methods 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000002244 precipitate Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 238000013019 agitation Methods 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- VJXRKZJMGVSXPX-UHFFFAOYSA-N 4-ethylpyridine Chemical compound CCC1=CC=NC=C1 VJXRKZJMGVSXPX-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 229910045601 alloy Inorganic materials 0.000 claims description 6
- 239000000956 alloy Substances 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 238000003828 vacuum filtration Methods 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 2
- 238000007664 blowing Methods 0.000 claims description 2
- 239000002041 carbon nanotube Substances 0.000 claims description 2
- 229910021393 carbon nanotube Inorganic materials 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- -1 gac Substances 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 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
- 238000002390 rotary evaporation Methods 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 13
- 238000010025 steaming Methods 0.000 abstract description 11
- 239000011261 inert gas Substances 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- NBPGPQJFYXNFKN-UHFFFAOYSA-N 4-methyl-2-(4-methylpyridin-2-yl)pyridine Chemical group CC1=CC=NC(C=2N=CC=C(C)C=2)=C1 NBPGPQJFYXNFKN-UHFFFAOYSA-N 0.000 description 11
- 238000010992 reflux Methods 0.000 description 7
- 239000010935 stainless steel Substances 0.000 description 7
- 229910001220 stainless steel Inorganic materials 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- GXZWAPVIGBCWCM-UHFFFAOYSA-N 4-(ethoxymethyl)pyridine Chemical compound CCOCC1=CC=NC=C1 GXZWAPVIGBCWCM-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000009834 vaporization Methods 0.000 description 3
- 230000008016 vaporization Effects 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- 206010019332 Heat exhaustion Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 229910021655 trace metal ion Inorganic materials 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Catalysts (AREA)
Abstract
Description
Claims (7)
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CN2008100562785A CN101219988B (zh) | 2008-01-16 | 2008-01-16 | 一种4,4′-二取代基-2,2′-联吡啶的合成方法 |
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CN2008100562785A CN101219988B (zh) | 2008-01-16 | 2008-01-16 | 一种4,4′-二取代基-2,2′-联吡啶的合成方法 |
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CN101219988A true CN101219988A (zh) | 2008-07-16 |
CN101219988B CN101219988B (zh) | 2010-12-15 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103664769A (zh) * | 2013-12-23 | 2014-03-26 | 北京师范大学 | 一种联吡啶衍生物或类似物的合成方法 |
CN105859610A (zh) * | 2016-04-22 | 2016-08-17 | 合肥工业大学 | 采用负载型双金属纳米催化剂的2,2’-联吡啶的合成方法 |
CN106800529A (zh) * | 2015-11-26 | 2017-06-06 | 中国科学院大连化学物理研究所 | 一种2,2′-联吡啶的制备方法 |
CN107935919A (zh) * | 2017-11-17 | 2018-04-20 | 南京红太阳生物化学有限责任公司 | 一种2,2’‑联吡啶及其衍生物的制备方法 |
CN116283738A (zh) * | 2023-03-15 | 2023-06-23 | 山东明化新材料有限公司 | 一种复合催化剂合成2,2’-联吡啶的方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1931841A (zh) * | 2006-10-11 | 2007-03-21 | 哈尔滨工业大学 | 一种4,4′-二甲基-2,2′-联吡啶的合成方法 |
-
2008
- 2008-01-16 CN CN2008100562785A patent/CN101219988B/zh not_active Expired - Fee Related
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103664769A (zh) * | 2013-12-23 | 2014-03-26 | 北京师范大学 | 一种联吡啶衍生物或类似物的合成方法 |
CN106800529A (zh) * | 2015-11-26 | 2017-06-06 | 中国科学院大连化学物理研究所 | 一种2,2′-联吡啶的制备方法 |
CN105859610A (zh) * | 2016-04-22 | 2016-08-17 | 合肥工业大学 | 采用负载型双金属纳米催化剂的2,2’-联吡啶的合成方法 |
WO2017181514A1 (zh) * | 2016-04-22 | 2017-10-26 | 安徽国星生物化学有限公司 | 采用负载型双金属纳米催化剂的2,2'-联吡啶的合成方法 |
CN107935919A (zh) * | 2017-11-17 | 2018-04-20 | 南京红太阳生物化学有限责任公司 | 一种2,2’‑联吡啶及其衍生物的制备方法 |
WO2019095613A1 (zh) * | 2017-11-17 | 2019-05-23 | 南京红太阳生物化学有限责任公司 | 一种2,2'-联吡啶及其衍生物的制备方法 |
CN107935919B (zh) * | 2017-11-17 | 2019-09-03 | 南京红太阳生物化学有限责任公司 | 一种2,2’-联吡啶及其衍生物的制备方法 |
GB2583216A (en) * | 2017-11-17 | 2020-10-21 | Nanjing Redsun Biochemistry Co Ltd | Method for preparing 2,2'-dipyridine and derivatives thereof |
US11014886B2 (en) | 2017-11-17 | 2021-05-25 | Nanjing Redsun Biochemistry Co., Ltd. | Method for preparing 2,2′-dipyridine and derivatives thereof |
GB2583216B (en) * | 2017-11-17 | 2022-08-10 | Nanjing Redsun Biochemistry Co Ltd | Method for preparing 2,2'-dipyridine and derivatives thereof |
CN116283738A (zh) * | 2023-03-15 | 2023-06-23 | 山东明化新材料有限公司 | 一种复合催化剂合成2,2’-联吡啶的方法 |
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CN101219988B (zh) | 2010-12-15 |
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