CN104555977A - 一种富勒醇的制备方法 - Google Patents
一种富勒醇的制备方法 Download PDFInfo
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- CN104555977A CN104555977A CN201410763239.4A CN201410763239A CN104555977A CN 104555977 A CN104555977 A CN 104555977A CN 201410763239 A CN201410763239 A CN 201410763239A CN 104555977 A CN104555977 A CN 104555977A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 36
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003960 organic solvent Substances 0.000 claims abstract description 27
- 239000002904 solvent Substances 0.000 claims abstract description 23
- 229910003472 fullerene Inorganic materials 0.000 claims abstract description 18
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 104
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 55
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 230000000640 hydroxylating effect Effects 0.000 claims description 19
- 239000008346 aqueous phase Substances 0.000 claims description 18
- 239000003513 alkali Substances 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 13
- 238000000502 dialysis Methods 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 10
- 235000021050 feed intake Nutrition 0.000 claims description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 238000011084 recovery Methods 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 7
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 238000011160 research Methods 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 claims description 3
- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 claims description 2
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical group CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012047 saturated solution Substances 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 4
- 230000033444 hydroxylation Effects 0.000 abstract description 4
- 238000005805 hydroxylation reaction Methods 0.000 abstract description 4
- 239000007787 solid Substances 0.000 abstract description 3
- 230000005298 paramagnetic effect Effects 0.000 abstract description 2
- 238000009987 spinning Methods 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract 1
- 239000005416 organic matter Substances 0.000 abstract 1
- 238000007670 refining Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 24
- 229910052799 carbon Inorganic materials 0.000 description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- 238000005516 engineering process Methods 0.000 description 13
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 238000002186 photoelectron spectrum Methods 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 3
- 239000002086 nanomaterial Substances 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- APQSQLNWAIULLK-UHFFFAOYSA-N 1,4-dimethylnaphthalene Chemical compound C1=CC=C2C(C)=CC=C(C)C2=C1 APQSQLNWAIULLK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 230000002292 Radical scavenging effect Effects 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000012163 sequencing technique Methods 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000005967 1,4-Dimethylnaphthalene Substances 0.000 description 1
- ZNWLFTSPNBLXGL-UHFFFAOYSA-N 4-(1,4-dioxaspiro[4.5]decan-8-yl)cyclohexan-1-one Chemical group C1CC(=O)CCC1C1CCC2(OCCO2)CC1 ZNWLFTSPNBLXGL-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000000026 X-ray photoelectron spectrum Methods 0.000 description 1
- OBOXTJCIIVUZEN-UHFFFAOYSA-N [C].[O] Chemical compound [C].[O] OBOXTJCIIVUZEN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000012675 alcoholic extract Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000002717 carbon nanostructure Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000007337 electrophilic addition reaction Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000007760 free radical scavenging Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 150000004715 keto acids Chemical group 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002539 nanocarrier Substances 0.000 description 1
- 239000002071 nanotube Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000447 pesticide residue Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000005837 radical ions Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 238000010671 solid-state reaction Methods 0.000 description 1
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- 238000001308 synthesis method Methods 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
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- 239000002699 waste material Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108203088A (zh) * | 2016-12-16 | 2018-06-26 | 北京福纳康生物技术有限公司 | 一种高水溶性富勒醇及其制备方法 |
CN109331189A (zh) * | 2018-09-07 | 2019-02-15 | 河南农业大学 | 一种顺磁性钆基金属富勒醇的制备方法 |
CN110292583A (zh) * | 2019-06-28 | 2019-10-01 | 中国科学院高能物理研究所 | 富勒醇及其组合物在制备抗血栓药物中的应用 |
CN111355132A (zh) * | 2018-12-21 | 2020-06-30 | 汉能移动能源控股集团有限公司 | 富勒醇负离子释放头及其制备方法和负离子发生电极 |
US10961414B2 (en) | 2018-07-23 | 2021-03-30 | Samsung Electronics Co., Ltd. | Polishing slurry, method of manufacturing the same, and method of manufacturing semiconductor device |
CN113772658A (zh) * | 2021-10-18 | 2021-12-10 | 厦门福纳新材料科技有限公司 | 一种富勒醇抗辐射防护剂 |
CN113926487A (zh) * | 2021-09-14 | 2022-01-14 | 杭州师范大学 | 一种富勒醇/钯纳米复合光催化剂及其制备方法、应用 |
CN114602447A (zh) * | 2022-03-28 | 2022-06-10 | 杭州师范大学 | 富勒醇/金纳米颗粒复合光催化剂的制备方法 |
CN114713194A (zh) * | 2022-04-27 | 2022-07-08 | 昆明理工大学 | 一种利用海螵蛸生物炭去除水体中富勒醇的方法 |
CN115463094A (zh) * | 2021-06-10 | 2022-12-13 | 北京微著新材科技有限公司 | 一种口服放疗防护剂及其制备方法和应用 |
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JPH0748302A (ja) * | 1993-07-30 | 1995-02-21 | Tokyo Gas Co Ltd | フラロールの合成方法 |
CN1316411A (zh) * | 2001-03-14 | 2001-10-10 | 陈滇宝 | 一种制备富勒醇的新方法 |
CN1483670A (zh) * | 2002-09-17 | 2004-03-24 | 中国科学院化学研究所 | 一种富勒醇的制备方法 |
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2014
- 2014-12-11 CN CN201410763239.4A patent/CN104555977B/zh active Active
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JPH0748302A (ja) * | 1993-07-30 | 1995-02-21 | Tokyo Gas Co Ltd | フラロールの合成方法 |
CN1316411A (zh) * | 2001-03-14 | 2001-10-10 | 陈滇宝 | 一种制备富勒醇的新方法 |
CN1483670A (zh) * | 2002-09-17 | 2004-03-24 | 中国科学院化学研究所 | 一种富勒醇的制备方法 |
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JING LI ET AL.: "C60 Fullerol Formation catalysed by Quaternary Ammonium Hydroxides", 《JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS》 * |
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Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108203088A (zh) * | 2016-12-16 | 2018-06-26 | 北京福纳康生物技术有限公司 | 一种高水溶性富勒醇及其制备方法 |
US10961414B2 (en) | 2018-07-23 | 2021-03-30 | Samsung Electronics Co., Ltd. | Polishing slurry, method of manufacturing the same, and method of manufacturing semiconductor device |
CN109331189A (zh) * | 2018-09-07 | 2019-02-15 | 河南农业大学 | 一种顺磁性钆基金属富勒醇的制备方法 |
CN109331189B (zh) * | 2018-09-07 | 2021-06-18 | 河南农业大学 | 一种顺磁性钆基金属富勒醇的制备方法 |
CN111355132A (zh) * | 2018-12-21 | 2020-06-30 | 汉能移动能源控股集团有限公司 | 富勒醇负离子释放头及其制备方法和负离子发生电极 |
CN110292583B (zh) * | 2019-06-28 | 2020-06-16 | 中国科学院高能物理研究所 | 富勒醇及其组合物在制备抗血栓药物中的应用 |
CN110292583A (zh) * | 2019-06-28 | 2019-10-01 | 中国科学院高能物理研究所 | 富勒醇及其组合物在制备抗血栓药物中的应用 |
CN115463094A (zh) * | 2021-06-10 | 2022-12-13 | 北京微著新材科技有限公司 | 一种口服放疗防护剂及其制备方法和应用 |
CN113926487A (zh) * | 2021-09-14 | 2022-01-14 | 杭州师范大学 | 一种富勒醇/钯纳米复合光催化剂及其制备方法、应用 |
CN113772658A (zh) * | 2021-10-18 | 2021-12-10 | 厦门福纳新材料科技有限公司 | 一种富勒醇抗辐射防护剂 |
CN114602447A (zh) * | 2022-03-28 | 2022-06-10 | 杭州师范大学 | 富勒醇/金纳米颗粒复合光催化剂的制备方法 |
CN114713194A (zh) * | 2022-04-27 | 2022-07-08 | 昆明理工大学 | 一种利用海螵蛸生物炭去除水体中富勒醇的方法 |
CN114713194B (zh) * | 2022-04-27 | 2023-11-14 | 昆明理工大学 | 一种利用海螵蛸生物炭去除水体中富勒醇的方法 |
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