CN101619050B - 催化5-羟甲基糠醛制备2,5-二甲酰基呋喃的方法 - Google Patents
催化5-羟甲基糠醛制备2,5-二甲酰基呋喃的方法 Download PDFInfo
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- CN101619050B CN101619050B CN200810012159XA CN200810012159A CN101619050B CN 101619050 B CN101619050 B CN 101619050B CN 200810012159X A CN200810012159X A CN 200810012159XA CN 200810012159 A CN200810012159 A CN 200810012159A CN 101619050 B CN101619050 B CN 101619050B
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- hydroxymethyl furfural
- oxygen
- oxyradical
- nitrite
- catalyst system
- Prior art date
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- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 title claims abstract description 40
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 21
- PXJJKVNIMAZHCB-UHFFFAOYSA-N 2,5-diformylfuran Chemical compound O=CC1=CC=C(C=O)O1 PXJJKVNIMAZHCB-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 39
- 239000001301 oxygen Substances 0.000 claims abstract description 39
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 37
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 230000003647 oxidation Effects 0.000 claims abstract description 17
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 17
- 238000000926 separation method Methods 0.000 claims abstract description 14
- 230000001590 oxidative effect Effects 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract 2
- 229910001935 vanadium oxide Inorganic materials 0.000 claims abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
- 239000007787 solid Substances 0.000 claims description 33
- 238000003756 stirring Methods 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical group [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 13
- 238000010792 warming Methods 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 11
- 238000001291 vacuum drying Methods 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 235000010288 sodium nitrite Nutrition 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- IBYSTTGVDIFUAY-UHFFFAOYSA-N vanadium monoxide Chemical compound [V]=O IBYSTTGVDIFUAY-UHFFFAOYSA-N 0.000 claims description 5
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 claims description 4
- LJYCJDQBTIMDPJ-UHFFFAOYSA-N [P]=O.[V] Chemical compound [P]=O.[V] LJYCJDQBTIMDPJ-UHFFFAOYSA-N 0.000 claims description 4
- 235000010289 potassium nitrite Nutrition 0.000 claims description 4
- 239000004304 potassium nitrite Substances 0.000 claims description 4
- -1 at 50-120 °C Chemical compound 0.000 claims description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- IDNHOWMYUQKKTI-UHFFFAOYSA-M lithium nitrite Chemical compound [Li+].[O-]N=O IDNHOWMYUQKKTI-UHFFFAOYSA-M 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 8
- 239000006227 byproduct Substances 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 abstract 1
- 150000002826 nitrites Chemical class 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 230000009466 transformation Effects 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 230000000153 supplemental effect Effects 0.000 description 8
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 229910001882 dioxygen Inorganic materials 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
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CN200810012159XA CN101619050B (zh) | 2008-07-04 | 2008-07-04 | 催化5-羟甲基糠醛制备2,5-二甲酰基呋喃的方法 |
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CN200810012159XA CN101619050B (zh) | 2008-07-04 | 2008-07-04 | 催化5-羟甲基糠醛制备2,5-二甲酰基呋喃的方法 |
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CN101619050A CN101619050A (zh) | 2010-01-06 |
CN101619050B true CN101619050B (zh) | 2011-06-22 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103739573A (zh) * | 2014-02-11 | 2014-04-23 | 厦门大学 | 催化转化生物质葡萄糖制备2,5-二甲酰基呋喃的方法 |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102010030991A1 (de) | 2010-07-06 | 2012-01-12 | Evonik Degussa Gmbh | Verfahren zur Herstellung von 2,5-Diformylfuran und seiner Derivate |
CN102827368B (zh) * | 2011-06-16 | 2014-04-23 | 中国科学院大连化学物理研究所 | 一种生物质基有机聚合物多孔材料及其合成方法 |
CN102827336B (zh) * | 2011-06-16 | 2013-11-06 | 中国科学院大连化学物理研究所 | 一种生物质基酚醛树脂及其制备方法 |
FR2984889B1 (fr) * | 2011-12-22 | 2017-02-24 | Roquette Freres | Procede ameliore d'oxydation selective du 5-hydromethyl furaldehyde |
WO2014121513A1 (en) * | 2013-02-08 | 2014-08-14 | Rhodia Operations | Oxydation of alcohol compounds via mesostructured vpo catalysts |
CN105753821B (zh) * | 2014-12-17 | 2018-11-02 | 中国科学院宁波材料技术与工程研究所 | 一种2,5-呋喃二甲酸的制备方法 |
CN104529957B (zh) * | 2014-12-26 | 2016-04-13 | 中国科学技术大学先进技术研究院 | 一种2,5-呋喃二甲酸的制备方法 |
CN104829563B (zh) * | 2015-04-24 | 2017-01-11 | 华南理工大学 | 一种分离5-羟甲基糠醛与2,5-二甲酰基呋喃混合物的方法 |
CN106008416B (zh) * | 2016-07-04 | 2019-02-19 | 浙江大学 | 一种2,5-呋喃二甲醛的制备方法 |
CN106967019B (zh) * | 2017-05-08 | 2020-01-24 | 湖南师范大学 | 一种制备2,5-二甲酰基呋喃的方法 |
CN109438399B (zh) * | 2018-12-27 | 2022-10-11 | 南京林业大学 | 一种选择性氧化5-羟甲基糠醛制备2,5-二甲酰基呋喃的方法 |
CN113683588A (zh) * | 2020-05-19 | 2021-11-23 | 中国科学院大连化学物理研究所 | 一种2,5-二甲酰基呋喃的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19615878A1 (de) * | 1996-04-22 | 1997-10-23 | Episucres Sa | Verfahren zum selektiven Herstellen von Furandicarboxaldehyd-2,5 ausgehend von Hydroxymethyl-5-Furancarboxaldehyd 2 |
CN1555368A (zh) * | 2001-09-17 | 2004-12-15 | ��Ļ���Ű˾ | 由碳水化合物制备2,5-二甲酰呋喃的方法 |
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- 2008-07-04 CN CN200810012159XA patent/CN101619050B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19615878A1 (de) * | 1996-04-22 | 1997-10-23 | Episucres Sa | Verfahren zum selektiven Herstellen von Furandicarboxaldehyd-2,5 ausgehend von Hydroxymethyl-5-Furancarboxaldehyd 2 |
CN1555368A (zh) * | 2001-09-17 | 2004-12-15 | ��Ļ���Ű˾ | 由碳水化合物制备2,5-二甲酰呋喃的方法 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103739573A (zh) * | 2014-02-11 | 2014-04-23 | 厦门大学 | 催化转化生物质葡萄糖制备2,5-二甲酰基呋喃的方法 |
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Effective date of registration: 20240327 Address after: No. 300-8, jinlongsi Road, Ganjingzi District, Dalian, Liaoning 116036 Patentee after: Zhongke Huawu (Dalian) Technology Innovation Service Co.,Ltd. Country or region after: China Address before: Building 3, No. 161 Zhongshan Road, Xigang District, Dalian, Liaoning 116021 Patentee before: Zhongke Chemical (Dalian) Technology Industry Co.,Ltd. Country or region before: China |