CN117623840A - 环戊酮合成环戊二烯的方法 - Google Patents
环戊酮合成环戊二烯的方法 Download PDFInfo
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- CN117623840A CN117623840A CN202210956521.9A CN202210956521A CN117623840A CN 117623840 A CN117623840 A CN 117623840A CN 202210956521 A CN202210956521 A CN 202210956521A CN 117623840 A CN117623840 A CN 117623840A
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- Prior art keywords
- cyclopentanone
- metal
- metal oxide
- deionized water
- composite metal
- Prior art date
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- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 title claims abstract description 124
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 238000000034 method Methods 0.000 title claims abstract description 40
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 55
- 239000002131 composite material Substances 0.000 claims abstract description 39
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 39
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 39
- 239000002994 raw material Substances 0.000 claims abstract description 14
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 54
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 50
- 239000002184 metal Substances 0.000 claims description 36
- 229910052751 metal Inorganic materials 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000008367 deionised water Substances 0.000 claims description 27
- 229910021641 deionized water Inorganic materials 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 18
- 238000002156 mixing Methods 0.000 claims description 17
- 238000001035 drying Methods 0.000 claims description 15
- 238000005406 washing Methods 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 12
- 238000001354 calcination Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- 239000000725 suspension Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000009210 therapy by ultrasound Methods 0.000 claims description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 6
- 238000010668 complexation reaction Methods 0.000 claims description 6
- 230000008021 deposition Effects 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 6
- 230000008020 evaporation Effects 0.000 claims description 6
- 238000001027 hydrothermal synthesis Methods 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 238000000643 oven drying Methods 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 238000005303 weighing Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims 8
- 239000002028 Biomass Substances 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000011701 zinc Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 9
- 239000006004 Quartz sand Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000011049 filling Methods 0.000 description 7
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 6
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 6
- 239000011609 ammonium molybdate Substances 0.000 description 6
- 229940010552 ammonium molybdate Drugs 0.000 description 6
- 235000018660 ammonium molybdate Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000001276 controlling effect Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- -1 ketone acetate Chemical class 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 229960004424 carbon dioxide Drugs 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 1
- WTFUTSCZYYCBAY-SXBRIOAWSA-N 6-[(E)-C-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-N-hydroxycarbonimidoyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C/C(=N/O)/C1=CC2=C(NC(O2)=O)C=C1 WTFUTSCZYYCBAY-SXBRIOAWSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- 229920002488 Hemicellulose Polymers 0.000 description 1
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 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
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 150000001940 cyclopentanes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- SZQUEWJRBJDHSM-UHFFFAOYSA-N iron(3+);trinitrate;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O SZQUEWJRBJDHSM-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 239000012716 precipitator Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
- 150000004823 xylans Chemical class 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/28—Molybdenum
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
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- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/88—Molybdenum
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
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- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
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- C07C13/08—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring
- C07C13/15—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring with a cyclopentadiene ring
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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Abstract
本发明涉及生物质平台化合物环戊酮合成环戊二烯的方法，以环戊酮为原料，于固定床连续式反应器中，在AxByOz型复合金属氧化物催化剂的作用下，通过加氢脱氧串联脱氢反应，合成目标产物环戊二烯。本发明工艺路线简单，对环境友好，催化剂制备方便，为环戊酮合成环戊二烯提供了一种全新的有效途径。
Description
技术领域
本发明涉及环戊酮合成环戊二烯的方法。
背景技术
环戊二烯作为一种非常重要的化学品，是生产二茂铁、降冰片烯、环戊烯、金刚烷、环戊烷、卤代环戊烷及戊二醛等关键有机产品的基本原料，也可用于制备石油树脂和不饱和树脂以及高密度航空燃料JP-10等。然而，环戊二烯化学性质极为活泼，商业上一般以双环戊二烯的形式进行销售、运输以及储存。目前，工业上制备环戊二烯主要以裂解乙烯所得的C5为原料，一定温度下使环戊二烯二聚成双环戊二烯，然后通过减压精馏分离出高纯度的双环戊二烯，再解聚得到环戊二烯。CN1389444A公开了一种热解聚粗双环戊二烯制备高纯度环戊二烯的方法，利用气液相热解法，将粗二聚环戊二烯加入到内有载热液体，并且载热体温度加热到170-350℃的热分解器中，在冷凝温度42-80℃下收集分解产物。虽然该法高效简便，但是该工艺路线以储量有限且短时间无法再生的化石能源为原料，同时涉及反复解聚精馏过程，工艺设备复杂，能耗高。因此，开发绿色可持续合成环戊二烯的新路线已经刻不容缓。
生物质能作为地球上可再生能源中唯一的有机碳源载体，储量丰富，廉价易得，且是一种碳中性的天然资源，在转化过程中产生的二氧化碳可以继续参与植物的光合作用，实现碳循环，理论上二氧化碳零排放。因此，以可再生生物质资源替代传统化石能源作为原料来合成高附加值化学品已备受关注。例如，CN113968776A公开了一种生物质原料制备环戊酮的方法，该体系在一定的反应条件下可以将原生物质中的半纤维素、木聚糖、木糖、阿拉伯糖一步制备出高收率的环戊酮。但是，截止到目前，还没有文献报道过以生物质环戊酮为原料来合成环戊二烯。
发明内容
本发明所要解决的关键技术问题是提供一种环戊酮合成环戊二烯的方法，以生物质平台化合物环戊酮为原料，在固定床连续式反应器中，通过在AxByOz型复合金属氧化物催化剂上的加氢脱氧串联脱氢反应，将环戊酮一步转化为目标产物环戊二烯，为环戊酮制备高附加值环戊二烯化学品提供一种新型、简易、高效的合成方法。
本发明是通过以下技术方案实现的：
环戊酮合成环戊二烯的方法，以环戊酮为原料，在固定床连续式反应器中，在AxByOz型复合金属氧化物催化剂的作用下，通过加氢脱氧-脱氢反应，反应温度400-600℃(优选420-580℃，更优选450-570℃)，氢气压力0.0001-1MPa(优选0.0001-0.9MPa，更优选0.0001-0.8MPa)，氢气与环戊酮的摩尔比为20-400:1(30-350:1，更优选50-300:1)，环戊酮的时空速为0.01-10h-1(优选0.05-9h-1，更优选0.1-8h-1)下，即获得目标产物环戊二烯。
上述的原料环戊酮及目标产物环戊二烯的化学结构式见表1。
表1化合物的结构式
基于上述方案，优选地，所述AxByOz型复合金属氧化物催化剂包括：CuxMoyOz、ZnxMoyOz、NixMoyOz、CoxMoyOz、MnxMoyOz、FexMoyOz、CrxMoyOz、CuxWyOz、NixWyOz、CoxWyOz、FexWyOz、ZnxWyOz、ZnxVyOz中的一种或多种；其中，x为0.5-8，优选0.8-7，更优选1-6；y为0.5-8，优选0.8-7，更优选1-6；z为1-16，优选1-14，更优选1-12。
基于上述方案，优选地，所述AxByOz型复合金属氧化物催化剂采用水热法、沉积沉淀法或柠檬酸络合法制备，且使用前在氢气中进行还原处理，其中，还原条件为：氢气压力0.001-2.0MPa(优选0.005-1.5MPa，更优选0.01-1MPa)，氢气流速2-300mL/min(优选5-250mL/min，更优选10-200mL/min)，还原温度400-600℃(优选450-580℃，更优选480-570℃)，还原时间0.5-12h(优选0.7-10h，更优选1-8h)。
基于上述方案，优选地，所述AxByOz型复合金属氧化物催化剂采用水热法制备，具体制备过程为：将一定量A的金属盐与B的金属盐混合溶解在去离子水中，室温下超声得到悬浮液；将混合溶液转移至带聚四氟乙烯内衬的水热釜中，在80-220℃(优选90-200℃，更优选100-180℃)下反应5-48h(优选6-42h，更优选8-36h)后过滤洗涤，得到的粉末在80℃下干燥1-8h(优选2-6h，更优选3-5h)后于300-800℃(优选350-750℃，更优选400-700℃)下焙烧0.5-6h(优选1-5h，更优选1-4h)，即可得到AxByOz型复合金属氧化物催化剂。
基于上述方案，优选地，所述AxByOz型复合金属氧化物催化剂也可以采用沉积沉淀法制备，具体制备过程为：将一定量的B的金属盐溶于去离子水中，使用浓度为0.5-14mol/L(优选1-8mol/L，更优选1.5-6mol/L)氨水溶液作为沉淀剂调节该溶液的PH值调节为8-12后，滴加A的金属酸盐水溶液，搅拌0.5-4h(优选1-3.5h，更优选1-3h)后，将得到的沉淀过滤出来，经去离子水和乙醇洗涤后，于在50-120℃烘箱内烘干4-48h，再在300-800℃(优选350-750℃，更优选400-700℃)下焙烧0.5-10h(优选1-8h，更优选1-6h)，即可得到AxByOz型复合金属氧化物催化剂。
基于上述方案，优选地，所述AxByOz型复合金属氧化物催化剂还可以使用柠檬酸络合法制备，具体制备过程是：按摩尔比M:柠檬酸＝1:1-1:3(优选1:1.05-1:2，更优选1:1.1-1:1.5)称取B的金属酸盐、A的金属酸盐、柠檬酸，M为处于阴离子中的金属B和阳离子金属A的摩尔总和；用去离子水分别溶解后，将三者的溶液均匀混合，在蒸发皿中加热至仅有固体生成；经120℃干燥12h后在300-800℃(优选350-750℃，更优选400-700℃)下焙烧0.5-10h(优选1-8h，更优选1-6h)后，即可得到AxByOz型复合金属氧化物催化剂。
本发明所述的方法可实现生物质平台化合物环戊酮直接合成高附加值的环戊二烯，为环戊酮合成环戊二烯提供了一种全新的有效途径。
本发明的有益效果是：
本发明工艺路线简单，操作方便，对环境友好，能够将环戊酮经过加氢脱氧串联脱氢反应，一步转化为环戊二烯，是一条绿色高效的新途径。
本发明催化剂制备简单、可大量合成，反应条件温和，环戊酮转化率在92％以上，环戊二烯选择性在80％以上，催化性能良好，且稳定性和再生性能好。
本发明采用固定床连续流动反应器，在AxByOz型复合金属氧化物催化剂的作用下，能够将环戊酮一步转化为环戊二烯，具有可操作性大、能耗低、对环境友好的优势，可用于实际的工业化生产。
本发明首次以环戊酮为底物，于固定床连续式反应器中，通过加氢脱氧串联脱氢反应，可以一步直接合成具有高附加值的环戊二烯且原料转化率和产物选择性优良。截止到目前，还没有以环戊酮为原料，通过一步加氢脱氧-脱氢反应来合成环戊二烯的相关报道。
附图说明
图1为实施例7中环戊酮合成环戊二烯的产物的气相色谱图。
图2为目标产物环戊二烯的质谱对照图。
具体实施方式
以下结合具体实施例进一步详细描述本发明的技术方案，但本发明的保护范围不局限于这些实施例。
实施例1
(1)AxByOz型复合金属氧化物催化剂CoMoO4的制备：称取2.47g钼酸铵，溶于200mL去离子水中。使用浓度为2mol/L的氨水溶液作为沉淀剂将该溶液的PH值调节为9.5，滴加硝酸钴(4.07g溶于100mL去离子水中)水溶液，搅拌2h后，将得到的沉淀过滤出来，经去离子水和乙醇洗涤后，于在50℃烘箱内烘干4h，再在500℃下焙烧2h，即得CoMoO4复合金属氧化物催化剂。
(2)将上述CoMoO4催化剂0.4g与2g石英砂(40-70目)均匀混合，填装于固定床连续式反应器中，然后在氢气压力0.1MPa、氢气流量150mL/min、还原温度480℃下还原2h，然后控制反应温度480℃，氢气压力0.01MPa，氢气与环戊酮的摩尔比为50:1，环戊酮的时空速为1.33h-1，其环戊酮的转化率为94％，环戊二烯的选择性为83％。
实施例2
(1)AxByOz型复合金属氧化物催化剂NiMoO4的制备：按摩尔比M：柠檬酸＝1:1.2称取钼酸铵1.24g、硝酸镍2.04g、柠檬酸3.53g，M为处于阴离子中的金属B和阳离子金属A的摩尔总和；用去离子水分别溶解后，将三者的溶液均匀混合，在蒸发皿中加热至仅有固体生成；经120℃干燥12h后在550℃下焙烧5h后，即得NiMoO4复合金属氧化物催化剂。
(2)将上述NiMoO4催化剂0.8g与2g石英砂(40-70目)均匀混合，填装于固定床连续式反应器中，然后在氢气压力0.05MPa、氢气流量120mL/min、还原温度480℃下还原1h，然后控制反应温度500℃，氢气压力0.001MPa，氢气与环戊酮的摩尔比为100:1，环戊酮的时空速为0.67h-1，其环戊酮的转化率为96％，环戊二烯的选择性为85％。
实施例3
(1)AxByOz型复合金属氧化物催化剂Cu3Mo2O9的制备：将0.50g醋酸酮与0.44g钼酸铵溶解在40mL去离子水中，室温下超声得到悬浮液；将混合溶液转移至带聚四氟乙烯内衬的水热釜中，在140℃下反应12h后过滤洗涤，得到的粉末于80℃下干燥3h后在600℃下焙烧3h，即可得到Cu3Mo2O9复合金属氧化物催化剂。
(2)将上述Cu3Mo2O9催化剂0.2g与2g石英砂(40-70目)均匀混合，填装于固定床连续式反应器中，然后在氢气压力0.01MPa、氢气流量90mL/min、还原温度500℃下还原0.5h，然后控制反应温度520℃，氢气压力0.01MPa，氢气与环戊酮的摩尔比为100:1，环戊酮的时空速为2.67h-1，其环戊酮的转化率为92％，环戊二烯的选择性为82％。
实施例4
(1)AxByOz型复合金属氧化物催化剂Fe2(MoO4)3的制备：按摩尔比M：柠檬酸＝1:1.2称取钼酸铵1.24g、九水合硝酸铁1.89g、柠檬酸2.94g，M为处于阴离子中的金属B和阳离子金属A的摩尔总和；用去离子水分别溶解后，将三者的溶液均匀混合，在蒸发皿中加热至仅有固体生成；经120℃干燥12h后在600℃下焙烧3h后，即得Fe2(MoO4)3复合金属氧化物催化剂。
(2)将上述Fe2(MoO4)3催化剂0.4g与2g石英砂(40-70目)均匀混合，填装于固定床连续式反应器中，然后在氢气压力0.01MPa、氢气流量150mL/min、还原温度550℃下还原1h，然后控制反应温度550℃，氢气压力0.005MPa，氢气与环戊酮的摩尔比为50:1，环戊酮的时空速为1.33h-1，其环戊酮的转化率为96％，环戊二烯的选择性为84％。
实施例5
(1)AxByOz型复合金属氧化物催化剂NiWO4的制备：将0.71g醋酸镍与1.32g二水合钨酸钠溶解在80mL去离子水中，室温下超声得到悬浮液；将混合溶液转移至带聚四氟乙烯内衬的水热釜中，在120℃下反应24h后过滤洗涤，得到的粉末于80℃下干燥3h后于650℃下焙烧2h，即可得到NiWO4复合金属氧化物催化剂。
(2)将上述NiWO4催化剂0.4g与2g石英砂(40-70目)均匀混合，填装于固定床连续式反应器中，然后在氢气压力0.02MPa、氢气流量90mL/min、还原温度550℃下还原2h，然后控制反应温度570℃，氢气压力0.05MPa，氢气与环戊酮的摩尔比为75:1，环戊酮的时空速为2.67h-1，其环戊酮的转化率为95％，环戊二烯的选择性为83％。
实施例6
(1)AxByOz型复合金属氧化物催化剂Zn3(VO4)2的制备：将1.10g醋酸锌与0.47g偏钒酸铵溶解在60mL去离子水中，室温下超声得到悬浮液；将混合溶液转移至带聚四氟乙烯内衬的水热釜中，在160℃下反应12h后过滤洗涤，得到的粉末于80℃下干燥3h后于550℃下焙烧4h，即可得到Zn3(VO4)2复合金属氧化物催化剂。
(2)将上述Zn3(VO4)2催化剂0.2g与实施例5中合成的NiWO4催化剂0.2g机械混合后，再与2g石英砂(40-70目)均匀混合，填装于固定床连续式反应器中，然后在氢气压力0.01MPa、氢气流量120mL/min、还原温度500℃下还原0.5h，然后控制反应温度550℃，氢气压力0.001MPa，氢气与环戊酮的摩尔比为100:1，环戊酮的时空速为1.33h-1，其环戊酮的转化率为97％，环戊二烯的选择性为87％。
上述的实施例1-6的实验结果见表2。
表2由环戊酮加氢脱氧-脱氢合成环戊二烯
| 实施例 | 催化剂 | 环戊酮转化率/％ | 环戊二烯选择性/％ |
| 实施例1 | CoMoO4 | 94 | 83 |
| 实施例2 | NiMoO4 | 96 | 85 |
| 实施例3 | Cu3Mo2O9 | 92 | 82 |
| 实施例4 | Fe2(MoO4)3 | 96 | 84 |
| 实施例5 | NiWO4 | 95 | 83 |
| 实施例6 | Zn3(VO4)2+NiWO4 | 97 | 87 |
实施例7
(1)AxByOz型复合金属氧化物催化剂Zn3Mo2O9的制备：称取2.47g钼酸铵，溶于200mL去离子水中。使用浓度为4mol/L的氨水溶液作为沉淀剂调节该溶液的PH值调节为9.2后，滴加硝酸锌(4.16g溶于100mL去离子水中)水溶液，搅拌2h后，将得到的沉淀过滤出来，经去离子水和乙醇洗涤后，于在50℃烘箱内烘干6h，再在600℃下焙烧1h，即得Zn3Mo2O9复合金属氧化物催化剂。
(2)将上述Zn3Mo2O9催化剂0.8g与2g石英砂(40-70目)均匀混合，填装于固定床连续式反应器中，然后在氢气压力0.01MPa、氢气流量150mL/min、还原温度550℃下还原1h，然后控制反应温度550℃，氢气压力0.01MPa，氢气与环戊酮的摩尔比为100:1，环戊酮的时空速为0.67h-1，其环戊酮的转化率为95％，环戊二烯的选择性为86％。
在实施例7中的Zn3Mo2O9催化剂的制备过程中，其他条件不变，通过改变所加入钼酸铵的质量来得到不同Zn/Mo比的ZnxMoyOz复合金属氧化物催化剂，即为实施例8-12。将所得ZnxMoyOz催化剂0.8g与2g石英砂(40-70目)均匀混合，填装于固定床连续式反应器中，在氢气压力0.01MPa、氢气流量150mL/min、还原温度550℃下还原1h，然后在反应温度550℃，氢气压力0.01MPa，氢气与环戊酮的摩尔比为100:1，环戊酮的时空速为0.67h-1的条件下进行反应。
表3不同Zn/Mo比的ZnxMoyOz催化环戊酮加氢脱氧-脱氢合成环戊二烯
Claims (10)
1.环戊酮合成环戊二烯的方法，其特征在于，所述方法如下：以环戊酮为原料，在固定床连续式反应器中，在AxByOz型复合金属氧化物催化剂的作用下，通过加氢脱氧-脱氢反应，反应温度400-600℃，氢气压力0.0001-1MPa，氢气与环戊酮的摩尔比为20-400:1，环戊酮的时空速为0.01-10h-1，即可获得目标产物环戊二烯。
2.按照权利要求1所述的方法，其特征在于：反应温度420-580℃，氢气压力0.0001-0.9MPa，氢气与环戊酮的摩尔比为30-350:1，环戊酮的时空速为0.05-9h-1。
3.按照权利要求2所述的方法，其特征在于：反应温度450-570℃，氢气压力0.0001-0.8MPa，氢气与环戊酮的摩尔比为50-300:1，环戊酮的时空速为0.1-8h-1。
4.按照权利要求1所述的方法，其特征在于：所述AxByOz型复合金属氧化物催化剂包括：CuxMoyOz、ZnxMoyOz、NixMoyOz、CoxMoyOz、MnxMoyOz、FexMoyOz、CrxMoyOz、CuxWyOz、NixWyOz、CoxWyOz、FexWyOz、ZnxWyOz、ZnxVyOz中的一种或多种；其中，x为0.5-8，优选0.8-7，更优选1-6；y为0.5-8，优选0.8-7，更优选1-6；z为1-16，优选1-14，更优选1-12。
5.按照权利要求1或4所述的方法，其特征在于：所述AxByOz型复合金属氧化物催化剂采用水热法、沉积沉淀法或柠檬酸络合法制备，且使用前在氢气中进行还原处理；其中，还原处理的条件为：氢气压力0.001-2.0MPa，氢气流速2-300mL/min，温度400-600℃，时间0.5-12h。
6.按照权利要求5所述的方法，其特征在于，所述还原处理的条件为：氢气压力0.005-1.5MPa，氢气流速5-250mL/min，温度450-580℃，时间0.7-10h。
7.按照权利要求6所述的方法，其特征在于，所述还原处理的条件为：氢气压力0.01-1MPa，氢气流速10-200mL/min，温度480-570℃，时间1-8h。
8.按照权利要求5所述的方法，其特征在于，所述水热法包括以下步骤：将A的金属盐与B的金属盐混合溶解在去离子水中，室温下超声，得到悬浮液；将所述悬浮液在80-220℃下反应5-48h，然后过滤、洗涤，80℃下干燥1-8h，然后于300-800℃下焙烧0.5-6h，得到所述AxByOz型复合金属氧化物催化剂；
所述沉积沉淀法包括以下步骤：将B的金属盐溶于去离子水中，使用浓度为0.5-14mol/L氨水溶液作为沉淀剂将pH值调节为8-12，滴加A的金属酸盐水溶液，搅拌0.5-4h后，将得到的沉淀过滤出来，经去离子水和乙醇洗涤后，在50-120℃烘干4-48h，再在300-800℃下焙烧0.5-10h，得到所述AxByOz型复合金属氧化物催化剂；
所述柠檬酸络合法包括以下步骤：按摩尔比M:柠檬酸＝1:1～1:3称取B的金属酸盐、A的金属酸盐、柠檬酸，M为金属B和金属A的摩尔总和；用去离子水分别溶解后，将三者的溶液均匀混合，在蒸发皿中加热至仅有固体生成；经120℃干燥12h后在300-800℃下焙烧0.5-10h后，得到所述AxByOz型复合金属氧化物催化剂。
9.按照权利要求8所述的方法，其特征在于，所述水热法包括以下步骤：将A的金属盐与B的金属盐混合溶解在去离子水中，室温下超声，得到悬浮液；将所述悬浮液在90-200℃下反应6-42h，然后过滤、洗涤，80℃下干燥2-6h，然后于350-750℃下焙烧1-5h，得到所述AxByOz型复合金属氧化物催化剂；
所述沉积沉淀法包括以下步骤：将B的金属盐溶于去离子水中，使用浓度为1-8mol/L氨水溶液作为沉淀剂将pH值调节为8-12，滴加A的金属酸盐水溶液，搅拌1-3.5h后，将得到的沉淀过滤出来，经去离子水和乙醇洗涤后，在50-120℃烘干4-48h，再在350-750℃下焙烧1-8h，得到所述AxByOz型复合金属氧化物催化剂；
所述柠檬酸络合法包括以下步骤：按摩尔比M:柠檬酸＝1:1.05～1:2称取B的金属酸盐、A的金属酸盐、柠檬酸，M为金属B和金属A的摩尔总和；用去离子水分别溶解后，将三者的溶液均匀混合，在蒸发皿中加热至仅有固体生成；经120℃干燥12h后在350-750℃下焙烧1-8h后，得到所述AxByOz型复合金属氧化物催化剂。
10.按照权利要求9所述的方法，其特征在于，所述水热法包括以下步骤：将A的金属盐与B的金属盐混合溶解在去离子水中，室温下超声，得到悬浮液；将所述悬浮液在100-180℃下反应8-36h，然后过滤、洗涤，80℃下干燥3-5h，然后于400-700℃下焙烧1-4h，得到所述AxByOz型复合金属氧化物催化剂；
所述沉积沉淀法包括以下步骤：将B的金属盐溶于去离子水中，使用浓度为1.5-6mol/L氨水溶液作为沉淀剂将pH值调节为8-12，滴加A的金属酸盐水溶液，搅拌1-3h后，将得到的沉淀过滤出来，经去离子水和乙醇洗涤后，在50-120℃烘干4-48h，再在400-700℃下焙烧1-6h，得到所述AxByOz型复合金属氧化物催化剂；
所述柠檬酸络合法包括以下步骤：按摩尔比M:柠檬酸＝1:1.1～1:1.5称取B的金属酸盐、A的金属酸盐、柠檬酸，M为金属B和金属A的摩尔总和；用去离子水分别溶解后，将三者的溶液均匀混合，在蒸发皿中加热至仅有固体生成；经120℃干燥12h后在400-700℃下焙烧1-6h后，得到所述AxByOz型复合金属氧化物催化剂。
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