CN101607205B - 一种草酸二甲酯加氢制乙二醇催化剂及其制备方法 - Google Patents
一种草酸二甲酯加氢制乙二醇催化剂及其制备方法 Download PDFInfo
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- CN101607205B CN101607205B CN2009100633107A CN200910063310A CN101607205B CN 101607205 B CN101607205 B CN 101607205B CN 2009100633107 A CN2009100633107 A CN 2009100633107A CN 200910063310 A CN200910063310 A CN 200910063310A CN 101607205 B CN101607205 B CN 101607205B
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 110
- 239000003054 catalyst Substances 0.000 title claims abstract description 110
- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000005984 hydrogenation reaction Methods 0.000 title abstract description 23
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title abstract description 5
- 229910016344 CuSi Inorganic materials 0.000 claims abstract description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 41
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 239000007789 gas Substances 0.000 claims abstract description 23
- 150000002927 oxygen compounds Chemical class 0.000 claims abstract description 23
- 229910052742 iron Inorganic materials 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000004202 carbamide Substances 0.000 claims abstract description 11
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 11
- 239000010949 copper Substances 0.000 claims abstract description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052709 silver Inorganic materials 0.000 claims abstract description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052802 copper Inorganic materials 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims abstract description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 3
- 239000010703 silicon Substances 0.000 claims abstract description 3
- 229910052763 palladium Inorganic materials 0.000 claims abstract 5
- 239000012018 catalyst precursor Substances 0.000 claims description 47
- 239000012752 auxiliary agent Substances 0.000 claims description 42
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 39
- 238000000975 co-precipitation Methods 0.000 claims description 31
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 22
- 238000000465 moulding Methods 0.000 claims description 21
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 claims description 20
- 238000007598 dipping method Methods 0.000 claims description 19
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 16
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 claims description 11
- 239000011701 zinc Substances 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 230000001376 precipitating effect Effects 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000010944 silver (metal) Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 abstract description 17
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 abstract description 2
- 239000001099 ammonium carbonate Substances 0.000 abstract description 2
- 239000000654 additive Substances 0.000 abstract 3
- 230000000996 additive effect Effects 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 abstract 1
- 229910052681 coesite Inorganic materials 0.000 abstract 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 abstract 1
- 229910052906 cristobalite Inorganic materials 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 229910052682 stishovite Inorganic materials 0.000 abstract 1
- 229910052905 tridymite Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 40
- 230000000694 effects Effects 0.000 description 25
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 238000011160 research Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000011651 chromium Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- -1 hydrogen ester Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 229910017813 Cu—Cr Inorganic materials 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
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- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- 238000006424 Flood reaction Methods 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GXDVEXJTVGRLNW-UHFFFAOYSA-N [Cr].[Cu] Chemical compound [Cr].[Cu] GXDVEXJTVGRLNW-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
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- 239000000835 fiber Substances 0.000 description 1
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- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 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
- 239000000618 nitrogen fertilizer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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- Catalysts (AREA)
Abstract
Description
催化剂 | DMO转化率% | EG选择性% |
实施例1 20%CuO-3%ZnO-SiO2 | 96 | 81 |
实施例2 25%CuO-2.5%Fe2O3-SiO2 | 93 | 78 |
实施例3 30%CuO-0.7%AgO-SiO2 | 99 | 85 |
实施例4 35%CuO-0.03%PdO-SiO2 | 98 | 80 |
实施例5 40%CuO-0.005%PdO-SiO2 | 100 | 95 |
实施例6 45%CuO-1.2%ZnO-SiO2 | 99 | 87 |
实施例7 50%CuO-0.3%AgO-SiO2 | 100 | 96 |
实施例8 30%CuO-1.4%Fe2O3-SiO2 | 100 | 84 |
实施例9 40%CuO-0.01%PdO-SiO2 | 100 | 94 |
实施例10 30%CuO-1.0%ZnO-SiO2 | 98 | 90 |
实施例11 40%CuO-1.0%ZnO-0.01%PdO-SiO2 | 100 | 98 |
实施例12 35%CuO-1.0%ZnO-1.4%Fe2O3-SiO2 | 100 | 85 |
实施例13 34%CuO-1.2%ZnO-0.3%AgO-SiO2 | 97 | 89 |
实施例14 36%CuO-2.5%Fe2O3-0.03%PdO-SiO2 | 100 | 91 |
实施例15 45%CuO-0.35%AgO-0.01%PdO-SiO2 | 100 | 95 |
实施例16 35%CuO-1.2%Fe2O3-0.35%AgO-SiO2 | 100 | 92 |
Claims (6)
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Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101816934B (zh) * | 2010-04-15 | 2012-09-05 | 复旦大学 | 一种合成乙醇酸甲酯和乙二醇的银氧化硅催化剂及其制备方法 |
CN102247847B (zh) * | 2010-05-12 | 2015-03-04 | 中国科学院福建物质结构研究所 | 一种草酸酯加氢合成乙二醇的铜硅催化剂 |
CN102380391A (zh) * | 2010-08-26 | 2012-03-21 | 中科合成油技术有限公司 | 选择性脱酸催化剂及其制备方法、以及其在对费托合成油进行选择性加氢脱酸处理中的应用 |
CN101927200B (zh) * | 2010-08-26 | 2012-11-28 | 河南煤业化工集团有限责任公司 | 一种草酸二甲酯加氢制备乙二醇的催化剂的活化还原方法 |
CN101954288B (zh) * | 2010-09-27 | 2013-01-23 | 上海华谊(集团)公司 | 一种草酸二甲酯加氢制乙醇酸甲酯的催化剂及其制备方法和应用 |
CN102451716B (zh) * | 2010-10-21 | 2014-05-28 | 中国石油化工股份有限公司 | 一种加氢催化剂及乙二醇的合成方法 |
CN102151568B (zh) * | 2011-01-30 | 2013-07-31 | 山东华鲁恒升集团德化设计研究有限公司 | 草酸二甲酯加氢制备乙二醇的催化剂及制备和应用 |
CN102649691B (zh) * | 2011-02-25 | 2014-11-26 | 中国石油化工股份有限公司 | 提高草酸酯加氢反应制乙二醇选择性的方法 |
CN102228835A (zh) * | 2011-04-21 | 2011-11-02 | 合肥天焱绿色能源开发有限公司 | 一种合成低碳混合醇用催化剂及其制备方法 |
CN102895985B (zh) * | 2012-10-10 | 2015-04-01 | 南京信息工程大学 | 一种用于合成酸性气体吸收剂的催化剂及其制备方法 |
CN105727956A (zh) * | 2014-12-09 | 2016-07-06 | 上海华谊能源化工有限公司 | 一种草酸二甲酯气相加氢制取乙二醇催化剂及其制备方法与应用 |
CN106582652A (zh) * | 2015-10-16 | 2017-04-26 | 上海华谊能源化工有限公司 | 一种草酸二甲酯气相加氢合成乙二醇的催化剂及其制备方法与应用 |
CN106861710A (zh) * | 2017-02-20 | 2017-06-20 | 宁波中科远东催化工程技术有限公司 | 草酸二甲酯制乙二醇的催化剂及其制备方法 |
CN109433206B (zh) * | 2018-11-28 | 2021-07-23 | 中触媒新材料股份有限公司 | 具有中心辐射状孔道介孔氧化硅负载铜催化剂制备方法 |
CN110947382B (zh) * | 2019-08-27 | 2023-03-17 | 天津大学 | 一种用于碳酸乙烯酯加氢制甲醇联产乙二醇的催化剂及其制备方法 |
CN114054041B (zh) * | 2021-09-29 | 2024-06-11 | 中触媒新材料股份有限公司 | 草酸二甲酯加氢催化剂、其制法及应用 |
CN115414934B (zh) * | 2022-07-21 | 2024-08-20 | 朱义峰 | 固体铜基催化剂、制备方法及其用途、储存和释放氢气的储氢体系、储存和释放氢气的方法 |
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CN101138730A (zh) * | 2007-10-10 | 2008-03-12 | 天津大学 | 草酸酯加氢合成乙醇酸酯的催化剂及其制备方法 |
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