CN115385882A - 一种制备δ-己内酯的方法 - Google Patents
一种制备δ-己内酯的方法 Download PDFInfo
- Publication number
- CN115385882A CN115385882A CN202211053900.3A CN202211053900A CN115385882A CN 115385882 A CN115385882 A CN 115385882A CN 202211053900 A CN202211053900 A CN 202211053900A CN 115385882 A CN115385882 A CN 115385882A
- Authority
- CN
- China
- Prior art keywords
- caprolactone
- delta
- catalyst
- preparing
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- RZTOWFMDBDPERY-UHFFFAOYSA-N Delta-Hexanolactone Chemical compound CC1CCCC(=O)O1 RZTOWFMDBDPERY-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 22
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 claims abstract description 15
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 7
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 6
- 238000005470 impregnation Methods 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 235000012209 glucono delta-lactone Nutrition 0.000 claims description 6
- 229960003681 gluconolactone Drugs 0.000 claims description 6
- 229910021389 graphene Inorganic materials 0.000 claims description 6
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 claims description 5
- 229910003449 rhenium oxide Inorganic materials 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 229910003445 palladium oxide Inorganic materials 0.000 claims 1
- 239000002028 Biomass Substances 0.000 abstract description 11
- 230000003197 catalytic effect Effects 0.000 abstract description 7
- 238000005516 engineering process Methods 0.000 abstract description 3
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 229910000476 molybdenum oxide Inorganic materials 0.000 abstract description 2
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 abstract description 2
- 229910001935 vanadium oxide Inorganic materials 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- -1 palladium modified rhenium oxide Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 238000005906 dihydroxylation reaction Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- ZIXLDMFVRPABBX-UHFFFAOYSA-N 2-methylcyclopentan-1-one Chemical compound CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 2
- MGTZCLMLSSAXLD-UHFFFAOYSA-N 5-oxohexanoic acid Chemical compound CC(=O)CCCC(O)=O MGTZCLMLSSAXLD-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000000686 essence Substances 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- JWDSCUIQYJUHHM-UHFFFAOYSA-N 2-ethylacetoacetic acid Chemical compound CCC(C(C)=O)C(O)=O JWDSCUIQYJUHHM-UHFFFAOYSA-N 0.000 description 1
- XIBPCLQLEGQADN-UHFFFAOYSA-N 4-acetyloxy-4-oxobutanoic acid Chemical compound CC(=O)OC(=O)CCC(O)=O XIBPCLQLEGQADN-UHFFFAOYSA-N 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- NWAHZABTSDUXMJ-UHFFFAOYSA-N platinum(2+);dinitrate Chemical compound [Pt+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O NWAHZABTSDUXMJ-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/648—Vanadium, niobium or tantalum or polonium
- B01J23/6482—Vanadium
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/652—Chromium, molybdenum or tungsten
- B01J23/6525—Molybdenum
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/656—Manganese, technetium or rhenium
- B01J23/6567—Rhenium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
本发明公开了一种制备δ‑己内酯的方法，属于生物质催化转化技术领域。本发明提供了一种制备精细化工高端化合物的新途径。以铂或钯改性的氧化铼、氧化钒或氧化钼为催化剂，将葡萄糖内酯一步转化为δ‑己内酯。根据本发明提供的技术，使得生产δ‑己内酯的工作系统成本大幅度降低且催化剂循环稳定性高，具有良好的工业应用前景。本发明不仅为δ‑己内酯的绿色合成提供了一条新路线，也为生物质催化转化提供了新的思路。
Description
技术领域
本发明属于生物质催化转化技术领域，本发明涉及一种制备δ-己内酯的新方法。
背景技术
δ-己内酯是一种高附加值精细化工化学品，广泛用于杏仁、樱桃、黄油、奶油等食用香精，也用于烟草香精；它是制取δ-羟基己酸及其盐类的原料；它还是一种潜在的可生物降解材料聚合单体，在社会发展与日常生活中有着重要作用。
现有制备δ-己内酯的方法主要以γ-乙酰丁酸为原料，用钠汞齐还原，然后进行酸化，或将δ-溴代己酸与水煮沸制取或由2-甲基环戊酮制得。其工艺条件繁琐和原料成本较高，导致δ-己内酯的市场报价极高。
目前，合成δ-己内酯的中国专利较少，其中申请号为CN202011246880.2的专利，介绍一种δ-己内酯香料的合成方法。以乙酰乙酸乙酯为起始原料制备δ-己内酯：第一步生成乙酰基琥珀酸酯，随后生成乙酰丁酸，然后通过贵金属催化剂加氢制备δ-己内酯。但其技术反应工艺过于繁琐，且碱会对设备造成腐蚀，破坏设备。
葡萄糖内酯是一种来源广泛的生物质衍生化合物，以葡萄糖内酯为起始原料，将其转化为δ-己内酯。不仅是一种绿色化学工艺，且仅需一步反应即可生成目标产物δ-己内酯。解决了多步反应的高成本、低收率及低纯度的技术问题。
以生物质及其衍生物为原料制备高附加值化学品对我们构建绿色的生活方式具有重要意义。因此，开发一种基于生物质原料的一步法制δ-己内酯并应用稳定性良好的多相催化剂，具有非常高的经济效益及环境效益。
发明内容
本发明公开了一种制备δ-己内酯的方法，属于生物质催化转化技术领域。本发明旨在提供一种以来源广泛的生物质单体葡萄糖衍生物——葡萄糖内酯为起始原料，生成δ-己内酯的新方法。与传统方法相比，原料成本大幅降低。本技术具有良好的工业应用前景，符合绿色化工的要求。
本发明的技术方案：
一种制备δ-己内酯的方法，以葡萄糖内酯为底物，以改性DODH为催化剂，反应温度区间为140-180℃，反应时间4-48h，H2压力为1-12MPa，搅拌的速率为500～1500rpm，制备得到δ-己内酯。
进一步，所述的催化剂与葡萄糖内酯的质量比为0.01～1，葡萄糖内酯在反应体系中的浓度为1-10g/L。
进一步，一定温度范围为140-180℃。
进一步，所述的改性DODH指的是通过浸渍法将活性组分金属铂或金属钯与活性组分氧化铼负载在载体上，控制金属铂或金属钯与金属氧化物的质量比为0.05～0.2。
本发明的有益效果：
1.反应工艺简单，根据反应条件的调节，一步实现葡萄糖内酯脱羟基制备δ-己内酯，多相催化工艺易于回收利用，有利于工业放大。
2.相比于其他金属催化剂，不需要在反应前进行还原，本发明的催化剂制备完成后，可以放置很长时间，反应前不需要再次还原。
3.以生物质衍生物拓展新的催化新反应，具有良好经济性。
具体实施方式
下面将详述本发明具体实施方式，进一步理解本发明的目的、技术方案以及有益效果。但应该声明，本发明并不因此受限于这些实施案例。
实施例1：
用去离子水分别溶解硝酸钯和高铼酸铵，以石墨烯为催化剂载体，使用共浸渍法制备改性DODH催化剂，氧化铼和钯的负载量分别为10wt％和1wt％，在氮气气氛下于500℃焙烧4小时(加热速率为5℃/min)，将其标记为ReOx-Pd/GO。
实施例2：
用去离子水分别溶解硝酸四氨合铂和高铼酸铵，以石墨烯为催化剂载体，使用共浸渍法制备改性DODH催化剂，氧化铼和铂的负载量分别为10wt％和1wt％，在氮气气氛下于500℃焙烧4小时(加热速率为5℃/min)，将其标记为ReOx-Pt/GO。
实施例3：
用去离子水分别溶解硝酸钯和仲钼酸铵，以石墨烯为催化剂载体，使用共浸渍法制备改性DODH催化剂，氧化钼和钯的负载量分别为10wt％和1wt％，在氮气气氛下于500℃焙烧4小时(加热速率为5℃/min)，将其标记为MoOx-Pd/GO。
实施例4：
用去离子水分别溶解硝酸钯和偏钒酸铵，以石墨烯为催化剂载体，使用共浸渍法制备改性DODH催化剂，氧化钒和钯的负载量分别为10wt％和1wt％，在氮气气氛下于500℃焙烧4小时(加热速率为5℃/min)，将其标记为VOx-Pd/GO。
实施例5：
考察活性金属的影响。首先将20mg不同催化剂、25mg葡萄糖内酯和10mL甲醇加入高压反应釜中。用氢气吹扫5次后，在室温下向反应釜中注入2MPa的氢气。然后，反应器加热到140℃(升温速度5℃/min)，反应24h，反应结果见表1。
表1催化性能评价
| 催化剂 | 底物转化率(mol％) | 产物收率(mol％) |
| ReOx-Pd/GO | ＞99 | 90 |
| ReOx-Pt/GO | ＞99 | 63 |
| MoOx-Pd/GO | 45 | 25 |
| VOx-Pd/GO | 31 | 15 |
尽管浸渍法是催化剂制备的常见技术，在此基础上，钼和钒作为同样的亲氧过渡金属，其氧化物也是常用的脱羟基催化剂。但是对于生物质衍生的葡萄糖内酯脱羟基制备δ-己内酯反应来说，氧化铼的催化性能远远高于其他金属氧化物。换言之，将浸渍法和脱羟基反应结合起来不能得到本技术。本申请权利要求保护的技术方案对所属技术领域的技术人员来说是并非是显而易见的，本发明的技术方案具有突出的实质性特点和显著的进步。
实施例6：
考察反应温度对产物收率的影响。首先将20mg的ReOx-Pd/GO、25mg葡萄糖内酯和10mL甲醇加入高压反应釜中。用氢气吹扫5次后，在室温下向反应釜中注入2MPa的氢气。然后，反应器加热到100℃、120℃、140℃、160℃、180℃(升温速度5℃/min)，反应24h，反应结果见表2。
表2温度对反应的影响
评估了该反应的合适反应区间，反应温度高于140℃底物即可近乎完全转化，进一步提高反应温度尽管可以缩短反应时间但会导致副反应的发生。
实施例7：催化剂循环利用的考评。
将实施例6中，取140℃下，反应24h后的催化剂，对其进行离心，真空干燥回收。将20mg的循环催化剂、25mg葡萄糖内酯和10mL甲醇加入高压反应釜中。用氢气吹扫5次后，在室温下向反应釜中注入2MPa的氢气。然后，反应器加热到140℃(升温速度5℃/min)，反应24h，该催化剂循环利用5次，反应结果见表3。
表3催化剂稳定性测试
| 循环次数 | 底物转化率(mol％) | 产物收率(mol％) |
| 1 | ＞99 | 90 |
| 2 | ＞99 | 88 |
| 3 | ＞99 | 92 |
| 4 | ＞99 | 87 |
| 5 | ＞99 | 89 |
多相催化剂是主要优点即可循环性，在本发明提供的技术方案中，改性DODH催化剂在生物质衍生的葡萄糖内酯催化脱羟基制δ-己内酯中展现了良好的循环稳定性。
Claims (5)
1.一种制备δ-己内酯的方法，其特征在于，以葡萄糖内酯为底物，以改性DODH为催化剂，采用反应釜为反应器，在一定温度范围内，反应时间为4-48h，H2压力为1-12MPa，搅拌的速率为500～1500rpm，制备得到δ-己内酯。
2.根据权利要求1所述的方法，其特征在于，所述的催化剂与葡萄糖内酯的质量比为0.01～1，葡萄糖内酯在反应体系中的浓度为1-10g/L。
3.根据权利要求1所述的方法，其特征在于，所述的一定温度范围为140-180℃。
4.根据权利要求1、2或3所述的方法，其特征在于，所述的改性DODH指的是通过浸渍法将活性组分金属铂或金属钯与活性组分氧化铼负载在载体上，控制金属铂或金属钯与金属氧化物的质量比为0.05～0.2。
5.根据权利要求4所述的方法，其特征在于，所述的载体为石墨烯或氧化石墨烯。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211053900.3A CN115385882B (zh) | 2022-08-30 | 2022-08-30 | 一种制备δ-己内酯的方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211053900.3A CN115385882B (zh) | 2022-08-30 | 2022-08-30 | 一种制备δ-己内酯的方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115385882A true CN115385882A (zh) | 2022-11-25 |
| CN115385882B CN115385882B (zh) | 2024-01-30 |
Family
ID=84123809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211053900.3A Active CN115385882B (zh) | 2022-08-30 | 2022-08-30 | 一种制备δ-己内酯的方法 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115385882B (zh) |
-
2022
- 2022-08-30 CN CN202211053900.3A patent/CN115385882B/zh active Active
Non-Patent Citations (2)
| Title |
|---|
| MASAZUMI TAMURA等: "Transformation of Sugars into Chiral Polyols over aHeterogeneous Catalyst", ANGEW.CHEM. INT. ED., vol. 57, pages 8058 * |
| WEIPING DENG等: "Efficient Catalysts for the Green Synthesis of Adipic Acid from Biomass", ANGEW.CHEM.INT. ED., vol. 60, pages 4712 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115385882B (zh) | 2024-01-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6772287B2 (ja) | ２，５−フランジカルボン酸製造用触媒、およびその触媒を用いた２，５−フランジカルボン酸の製造方法 | |
| RU2518371C1 (ru) | Способ получения этиленгликоля из полиоксисоединений | |
| CN103159606B (zh) | 一种以糠醛为原料制备环戊酮的方法 | |
| CN107721821B (zh) | 一种制备1,3-丙二醇的方法 | |
| CN112194577A (zh) | 一种糠醛及其衍生物水相加氢重排制备环戊酮类化合物的方法 | |
| CN113387835B (zh) | 一种合成3-羟基丁酰肼的方法 | |
| CN112742482B (zh) | 一种催化加氢的催化剂及其制备方法与应用 | |
| CN110183327B (zh) | 一种催化氧化羟基酯制备酮酸酯的方法 | |
| CN112961046B (zh) | 一种利用废弃生物质无碱合成乙醇酸的方法 | |
| CN115385882A (zh) | 一种制备δ-己内酯的方法 | |
| CN109053640B (zh) | 一种由乙酰丙酸及其酯类制备γ-戊内酯的方法 | |
| CN114950505A (zh) | 一种用于氧化苯乙烯加氢制备β-苯乙醇的催化剂及其制备方法和应用 | |
| CN110294672B (zh) | 一种1,2-丙二醇与短链烷基醇直接制备乳酸酯的方法 | |
| CN108636440B (zh) | 一种甘油水溶液加氢制1,3-丙二醇的催化剂及其制备方法 | |
| CN110357782B (zh) | 一种中长链脂肪醇及其酯的制备方法 | |
| CN111233802A (zh) | 一种糠酸酯的制备方法 | |
| CN114907296B (zh) | 一种高效催化丁二酸脱水生成丁二酸酐的方法 | |
| CN112979401B (zh) | 一种制备1,5-己二烯的方法 | |
| CN115772077B (zh) | 一种由阿拉伯糖醇催化转化制备手性d-甘油酸的方法 | |
| CN114890966B (zh) | 一种用于柠檬烯环氧化反应的催化剂 | |
| CN112375052B (zh) | 一种通过葡萄糖三步级联反应制备2,5-二甲酰呋喃的方法 | |
| CN115672358B (zh) | 一种乙烷氧化脱氢制备乙烯的核壳氧化物催化剂的制备方法及其应用 | |
| CN113292520B (zh) | 一种糠醛催化加氢制备糠醇的磁性催化剂的合成方法及应用 | |
| CN106554268A (zh) | 一种水相催化合成甲基琥珀酸的方法 | |
| CN102649728B (zh) | 由co气相反应生产草酸酯的方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |