CN113117705A - 一种改性钌基催化剂及由其催化制备2,5-呋喃二羧酸的方法 - Google Patents
一种改性钌基催化剂及由其催化制备2,5-呋喃二羧酸的方法 Download PDFInfo
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- CN113117705A CN113117705A CN201911408201.4A CN201911408201A CN113117705A CN 113117705 A CN113117705 A CN 113117705A CN 201911408201 A CN201911408201 A CN 201911408201A CN 113117705 A CN113117705 A CN 113117705A
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- CN
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- Prior art keywords
- catalyst
- ruthenium
- modified
- cobalt
- solid
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- Granted
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- 239000003054 catalyst Substances 0.000 title claims abstract description 56
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 26
- 150000003303 ruthenium Chemical class 0.000 title claims abstract description 16
- 238000006555 catalytic reaction Methods 0.000 title description 4
- ASHVULSQMDWKFO-UHFFFAOYSA-N MMF Natural products COCC1=CC=C(C=O)O1 ASHVULSQMDWKFO-UHFFFAOYSA-N 0.000 claims abstract description 39
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 239000007787 solid Substances 0.000 claims abstract description 19
- 239000010949 copper Substances 0.000 claims abstract description 17
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 15
- 239000010941 cobalt Substances 0.000 claims abstract description 15
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052802 copper Inorganic materials 0.000 claims abstract description 15
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 11
- 150000004706 metal oxides Chemical group 0.000 claims abstract description 11
- 238000011068 loading method Methods 0.000 claims abstract description 9
- 229910052588 hydroxylapatite Inorganic materials 0.000 claims abstract description 8
- 238000000926 separation method Methods 0.000 claims abstract description 8
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 claims abstract description 7
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 238000005470 impregnation Methods 0.000 claims abstract description 3
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 238000001035 drying Methods 0.000 claims description 14
- 238000005406 washing Methods 0.000 claims description 12
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 238000001179 sorption measurement Methods 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- OJLCQGGSMYKWEK-UHFFFAOYSA-K ruthenium(3+);triacetate Chemical compound [Ru+3].CC([O-])=O.CC([O-])=O.CC([O-])=O OJLCQGGSMYKWEK-UHFFFAOYSA-K 0.000 claims description 3
- 239000012266 salt solution Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- GTCKPGDAPXUISX-UHFFFAOYSA-N ruthenium(3+);trinitrate Chemical compound [Ru+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O GTCKPGDAPXUISX-UHFFFAOYSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 230000007547 defect Effects 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 238000001354 calcination Methods 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000001914 filtration Methods 0.000 description 10
- 230000003647 oxidation Effects 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 description 6
- 229910019891 RuCl3 Inorganic materials 0.000 description 5
- 238000002791 soaking Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000009616 inductively coupled plasma Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- -1 platinum group metals Chemical class 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/185—Phosphorus; Compounds thereof with iron group metals or platinum group metals
- B01J27/1856—Phosphorus; Compounds thereof with iron group metals or platinum group metals with platinum group metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0207—Pretreatment of the support
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
Abstract
Description
Claims (11)
Priority Applications (1)
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CN201911408201.4A CN113117705B (zh) | 2019-12-31 | 2019-12-31 | 一种改性钌基催化剂及由其催化制备2,5-呋喃二羧酸的方法 |
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CN201911408201.4A CN113117705B (zh) | 2019-12-31 | 2019-12-31 | 一种改性钌基催化剂及由其催化制备2,5-呋喃二羧酸的方法 |
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CN113117705A true CN113117705A (zh) | 2021-07-16 |
CN113117705B CN113117705B (zh) | 2024-05-07 |
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Citations (10)
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---|---|---|---|---|
US20150183755A1 (en) * | 2011-08-31 | 2015-07-02 | Archer Daniels Midland Company | Spray oxidation process for producing 2,5-furandicarboxylic acid from hydroxymethylfurfural |
CN105026383A (zh) * | 2013-03-14 | 2015-11-04 | 阿彻丹尼尔斯米德兰德公司 | 用于制备2,5-呋喃二甲酸的方法 |
CN105555774A (zh) * | 2013-09-19 | 2016-05-04 | 花王株式会社 | 2,5-呋喃二羧酸的制造方法 |
CN106565647A (zh) * | 2016-10-29 | 2017-04-19 | 华东理工大学 | 一种催化氧化5‑羟甲基糠醛制备2,5‑呋喃二甲酸的方法 |
CN106795130A (zh) * | 2014-08-19 | 2017-05-31 | 阿彻丹尼尔斯米德兰德公司 | 用于由羟甲基糠醛在水中生产2,5‑呋喃二甲酸的催化剂和方法 |
CN107365287A (zh) * | 2016-05-11 | 2017-11-21 | 中国石油化工股份有限公司 | 一种合成2,5-呋喃二甲酸的方法 |
CN107365286A (zh) * | 2016-05-11 | 2017-11-21 | 中国石油化工股份有限公司 | 一种合成2,5-呋喃二甲酸的方法 |
CN108299358A (zh) * | 2018-01-19 | 2018-07-20 | 中国科学技术大学 | 用于呋喃醇或醛类化合物的选择性氧化方法 |
CN108712931A (zh) * | 2016-03-07 | 2018-10-26 | 韩国生产技术研究院 | 用于制备2,5-呋喃二甲酸的催化剂和使用催化剂制备2,5-呋喃二甲酸的方法 |
WO2019004777A1 (ko) * | 2017-06-30 | 2019-01-03 | 한국생산기술연구원 | 하이드록시메틸푸르푸랄로부터 2,5-퓨란디메틸카르복실레이트의 제조방법 |
-
2019
- 2019-12-31 CN CN201911408201.4A patent/CN113117705B/zh active Active
Patent Citations (10)
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US20150183755A1 (en) * | 2011-08-31 | 2015-07-02 | Archer Daniels Midland Company | Spray oxidation process for producing 2,5-furandicarboxylic acid from hydroxymethylfurfural |
CN105026383A (zh) * | 2013-03-14 | 2015-11-04 | 阿彻丹尼尔斯米德兰德公司 | 用于制备2,5-呋喃二甲酸的方法 |
CN105555774A (zh) * | 2013-09-19 | 2016-05-04 | 花王株式会社 | 2,5-呋喃二羧酸的制造方法 |
CN106795130A (zh) * | 2014-08-19 | 2017-05-31 | 阿彻丹尼尔斯米德兰德公司 | 用于由羟甲基糠醛在水中生产2,5‑呋喃二甲酸的催化剂和方法 |
CN108712931A (zh) * | 2016-03-07 | 2018-10-26 | 韩国生产技术研究院 | 用于制备2,5-呋喃二甲酸的催化剂和使用催化剂制备2,5-呋喃二甲酸的方法 |
CN107365287A (zh) * | 2016-05-11 | 2017-11-21 | 中国石油化工股份有限公司 | 一种合成2,5-呋喃二甲酸的方法 |
CN107365286A (zh) * | 2016-05-11 | 2017-11-21 | 中国石油化工股份有限公司 | 一种合成2,5-呋喃二甲酸的方法 |
CN106565647A (zh) * | 2016-10-29 | 2017-04-19 | 华东理工大学 | 一种催化氧化5‑羟甲基糠醛制备2,5‑呋喃二甲酸的方法 |
WO2019004777A1 (ko) * | 2017-06-30 | 2019-01-03 | 한국생산기술연구원 | 하이드록시메틸푸르푸랄로부터 2,5-퓨란디메틸카르복실레이트의 제조방법 |
CN108299358A (zh) * | 2018-01-19 | 2018-07-20 | 中国科学技术大学 | 用于呋喃醇或醛类化合物的选择性氧化方法 |
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Title |
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CHRISTIAN M. PICHLER等: "Ruthenium Supported on High-Surface-Area Zirconia as an Efficient Catalyst for the Base-Free Oxidation of 5-Hydroxymethylfurfural to 2, 5-Furandicarboxylic Acid", 《CHEMSUSCHEM》, vol. 11, no. 13, 15 May 2018 (2018-05-15), pages 2083 - 2090 * |
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ZHENZHEN YANG等: "Selective synthesis of 2, 5-diformylfuran and 2, 5-furandicarboxylic acid from 5-hydroxymethylfurfural and fructose catalyzed by magnetically separable catalysts", 《ENERGY & FUELS》, vol. 31, no. 1, 26 November 2016 (2016-11-26), pages 533 - 541 * |
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