CN108821941A - Method for preparing cyclopentanol or cyclopentanone by catalytic conversion of biomass - Google Patents
Method for preparing cyclopentanol or cyclopentanone by catalytic conversion of biomass Download PDFInfo
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- CN108821941A CN108821941A CN201810794182.2A CN201810794182A CN108821941A CN 108821941 A CN108821941 A CN 108821941A CN 201810794182 A CN201810794182 A CN 201810794182A CN 108821941 A CN108821941 A CN 108821941A
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- furfural
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- reaction kettle
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 294
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 title claims abstract description 114
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 238000000034 method Methods 0.000 title claims abstract description 19
- 239000002028 Biomass Substances 0.000 title claims abstract description 8
- 230000003197 catalytic effect Effects 0.000 title abstract description 3
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims abstract description 278
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims abstract description 162
- 239000001257 hydrogen Substances 0.000 claims abstract description 132
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 132
- 239000003054 catalyst Substances 0.000 claims abstract description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000008367 deionised water Substances 0.000 claims abstract description 50
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 50
- 239000002904 solvent Substances 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 130
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000002242 deionisation method Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 description 124
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
- 239000011777 magnesium Substances 0.000 description 43
- 238000006555 catalytic reaction Methods 0.000 description 40
- 239000003795 chemical substances by application Substances 0.000 description 39
- 238000001514 detection method Methods 0.000 description 39
- 239000007789 gas Substances 0.000 description 39
- 230000007423 decrease Effects 0.000 description 20
- 239000000243 solution Substances 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 5
- MFUVDXOKPBAHMC-UHFFFAOYSA-N magnesium;dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MFUVDXOKPBAHMC-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- SWCIQHXIXUMHKA-UHFFFAOYSA-N aluminum;trinitrate;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Al+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O SWCIQHXIXUMHKA-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- SXTLQDJHRPXDSB-UHFFFAOYSA-N copper;dinitrate;trihydrate Chemical compound O.O.O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O SXTLQDJHRPXDSB-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000012041 precatalyst Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 3
- 229910001948 sodium oxide Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 2
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 229960003487 xylose Drugs 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- 241000609240 Ambelania acida Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920002488 Hemicellulose Polymers 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- SRBFZHDQGSBBOR-LECHCGJUSA-N alpha-D-xylose Chemical compound O[C@@H]1CO[C@H](O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-LECHCGJUSA-N 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/72—Copper
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for preparing cyclopentanol or cyclopentanone by catalytically converting biomass. Using Cu-containing catalyst, using deionized water as solvent, adding furfural or furfuryl alcohol into a high-pressure kettle, filling hydrogen, and reacting at a certain reaction temperature to obtain cyclopentanol or cyclopentanone. The catalyst is simple in preparation method, can catalyze furfural or furfuryl alcohol to prepare cyclopentanol or cyclopentanone through highly selective hydrogenation by controlling reaction conditions, is good in catalytic effect, easy to recover and reuse, and has good industrial application prospect.
Description
Technical field
The present invention relates to a kind of methods that catalyzed conversion biomass prepares cyclopentanol or cyclopentanone.
Background technique
Cyclopentanol is a kind of important fine chemistry intermediate, is widely used in the production of medicine, dyestuff and fragrance, simultaneously
It is also the solvent of drug and fragrance.Industrially usually add hydrogen with cyclopentanone to prepare cyclopentanol.
Cyclopentanone is a kind of multi-functional fine chemical material.It can be used for synthetic drug, insecticide, rubber chemistry
Product, herbicide and fragrance.Cyclopentanone can easily dissolve various resins, therefore be widely used as the solvent of electronics industry.
Traditional cyclopentanone synthetic method is the pyrolysis of adipic acid and its derivative and the oxidation of cyclopentene.Severe reaction conditions, process
It is cumbersome.Currently, cyclopentanone is in great demand, but still rely on the preparation of fossil based raw material.
With the reduction of global fossil fuel, the demand to alternative energy source is increased rapidly.It is produced using renewable biomass
Chemicals is of great significance for the sustainable development of the following chemical industry.Furfural is the acid-catalyzed dehydration product of xylose, wood
Sugar is the main component of hemicellulose.In the industry, furfural is produced by the agricultural raw material rich in pentosan, such as stalk, corncob,
Oat shell, bagasse etc..The catalytic hydrogenation of furfural is an important reaction, it can obtain furfuryl alcohol, tetrahydrofuran first
Alcohol, 2- methylfuran, 2- methyltetrahydrofuran, pentadiene, pentanediol etc..
Furfural is the product for carrying out the acid-catalyzed dehydration of pentose in water.The process of furfural is separated from the aqueous solution of formation
Increase its production cost.Use furfural aqueous solution as prepare the raw material of chemicals and fuel by significant reduction furfural production at
This.Therefore, it uses deionized water as solvent, is catalyzed the work that furfural or furfuryl alcohol high selectivity add hydrogen to prepare cyclopentanol or cyclopentanone
Process has good prospects for commercial application.
Summary of the invention
The present invention provides a kind of method that catalyzed conversion biomass prepares cyclopentanol or cyclopentanone.By controlling reaction condition
Catalysis furfural or furfuryl alcohol high selectivity add hydrogen to prepare cyclopentanol or cyclopentanone.Excellent catalytic effect is easily recycled reuse, has
Good prospects for commercial application.
The technical scheme is that：A kind of method that catalyzed conversion biomass prepares cyclopentanol or cyclopentanone, feature
It is, using catalyst containing Cu, makees solvent with deionized water, furfural or furfuryl alcohol is added in autoclave, hydrogen is filled with, certain
Reaction temperature under reaction obtain product cyclopentanol or cyclopentanone.It is cooled to room temperature after stopping heating, detects furfural or furfuryl alcohol
The selectivity of conversion ratio and cyclopentanol or cyclopentanone.
It is preferred that above-mentioned catalyst containing Cu is CuxMgyAl2The compound of different mol ratio, wherein x/y=0.07-0.25,
(x+y)/2=3.Catalyst containing Cu is prepared with conventional method, that is, coprecipitation preparation is first passed through, then by inert gas atmosphere
Lower calcining is enclosed, finally reduction is made under an atmosphere of hydrogen.
The dosage of preferred catalyst is the 10%-30% of furfural or furfuryl alcohol quality.It is preferred that the quality of deionized water is furfural
Or 1.6-20 times of furfuryl alcohol quality.
It is preferred that the dosage of hydrogen is 0.2MPa-4.0MPa.Preferable reaction temperature is 160-200 DEG C；Reaction time is 3-
21h。
Beneficial effect：
Preparation method used in catalyst provided by the invention is simple, is catalyzed furfural by control reaction condition or furfuryl alcohol is high
Degree selective hydrogenation prepares cyclopentanol or cyclopentanone.Use furfural aqueous solution as the raw material for preparing chemicals and fuel, can show
Reduction furfural production cost.There is good prospects for commercial application.
Specific embodiment
Case study on implementation 1：
0.9664g Gerhardite is weighed, 14.3590g magnesium nitrate hexahydrate, 7.503g ANN aluminium nitrate nonahydrate is in round bottom
In flask, 400ml deionized water is dissolved as solvent, is denoted as solution A.Weigh 10.5990g sodium carbonate, 13.3333g hydrogen
In a round bottom flask, 400ml deionized water is dissolved sodium oxide molybdena as solvent, is denoted as solution B.Under stirring at room temperature by solution
A is slowly added into solution B, is dripped off within 2 hours.By mixed solution, circulation is handled 12 hours at 110 DEG C.It filters and uses distilled water
Washing to PH is 7.Then in a vacuum drying oven 80 DEG C be dried in vacuo 12 hours, obtained pre-catalyst under nitrogen atmosphere
It is 300 DEG C that temperature is calcined in tube furnace, and heating rate is 5 DEG C/min, keeps 4h at such a temperature.Then under an atmosphere of hydrogen
It is 300 DEG C that temperature is calcined in tube furnace, and heating rate is 5 DEG C/min, keeps 2h at such a temperature.Temperature fall is to room temperature
After obtain catalyst Cu0.4Mg5.6Al2。
Case study on implementation 2：
1.9328g Gerhardite is weighed, 13.3333 magnesium nitrate hexahydrates, 7.503g ANN aluminium nitrate nonahydrate is in round bottom
In flask, 400ml deionized water is dissolved as solvent, is denoted as solution A.Weigh 10.5990g sodium carbonate, 13.3333g hydrogen
In a round bottom flask, 400ml deionized water is dissolved sodium oxide molybdena as solvent, is denoted as solution B.Under stirring at room temperature by solution
A is slowly added into solution B, is dripped off within 2 hours.By mixed solution, circulation is handled 12 hours at 110 DEG C.It filters and uses distilled water
Washing to PH is 7.Then in a vacuum drying oven 80 DEG C be dried in vacuo 12 hours, obtained pre-catalyst under nitrogen atmosphere
It is 300 DEG C that temperature is calcined in tube furnace, and heating rate is 5 DEG C/min, keeps 4h at such a temperature.Then under an atmosphere of hydrogen
It is 300 DEG C that temperature is calcined in tube furnace, and heating rate is 5 DEG C/min, keeps 2h at such a temperature.Temperature fall is to room temperature
After obtain catalyst Cu0.8Mg5.2Al2。
Case study on implementation 3：
2.8992g Gerhardite is weighed, 12.3077g magnesium nitrate hexahydrate, 7.503g ANN aluminium nitrate nonahydrate is in round bottom
In flask, 400ml deionized water is dissolved as solvent, is denoted as solution A.Weigh 10.5990g sodium carbonate, 13.3333g hydrogen
In a round bottom flask, 400ml deionized water is dissolved sodium oxide molybdena as solvent, is denoted as solution B.Under stirring at room temperature by solution
A is slowly added into solution B, is dripped off within 2 hours.By mixed solution, circulation is handled 12 hours at 110 DEG C.It filters and uses distilled water
Washing to PH is 7.Then in a vacuum drying oven 80 DEG C be dried in vacuo 12 hours, obtained pre-catalyst under nitrogen atmosphere
It is 300 DEG C that temperature is calcined in tube furnace, and heating rate is 5 DEG C/min, keeps 4h at such a temperature.Then under an atmosphere of hydrogen
It is 300 DEG C that temperature is calcined in tube furnace, and heating rate is 5 DEG C/min, keeps 2h at such a temperature.Temperature fall is to room temperature
After obtain catalyst Cu1.2Mg4.8Al2。
Case study on implementation 4：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 12h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 4 in 1.
Case study on implementation 5：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.8Mg5.2Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 12h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 5 in 1.
Case study on implementation 6：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added1.2Mg4.8Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 12h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 6 in 1.
Case study on implementation 7：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfuryl alcohol, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 12h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 7 in 1.
Case study on implementation 8：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 10.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 12h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 8 in 1.
Case study on implementation 9：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 15.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 12h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 9 in 1.
Case study on implementation 10：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 25.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 12h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 10 in 1.
Case study on implementation 11：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 30.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 12h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 11 in 1.
Case study on implementation 12：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 12h in 170 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 12 in 1.
Case study on implementation 13：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 12h in 180 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 13 in 1.
Case study on implementation 14：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 12h in 200 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 14 in 1.
Case study on implementation 15：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 9h in 190 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table 1
In case study on implementation 15 shown in.
Case study on implementation 16：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 10h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 16 in 1.
Case study on implementation 17：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 11h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 17 in 1.
Case study on implementation 18：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.2.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 13h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 18 in 1.
Case study on implementation 19：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.1.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 12h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 19 in 1.
Case study on implementation 20：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.1.5MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 12h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 20 in 1.
Case study on implementation 21：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.2.5MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 12h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 21 in 1.
Case study on implementation 22：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.2000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 40.0mg, seals reaction kettle.2.5MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 13h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 22 in 1.
Case study on implementation 23：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 0.5000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 100.0mg, seals reaction kettle.3.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 18h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 23 in 1.
Case study on implementation 24：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanol
In a kettle, 1.2500g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 250.0mg, seals reaction kettle.4.0MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 21h in 190 DEG C of heating mantle, is placed in room temperature decline to after reaction, take out reaction kettle from heating mantle
Temperature arrives room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanol.Reaction result is shown in Table
Shown in case study on implementation 24 in 1.
Case study on implementation 25：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 5h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 25 shown in.
Case study on implementation 26：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.8Mg5.2Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 5h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 26 shown in.
Case study on implementation 27：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added1.2Mg4.8Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 5h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 27 shown in.
Case study on implementation 28：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfuryl alcohol, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 4h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 28 shown in.
Case study on implementation 29：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 10.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 5h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 29 shown in.
Case study on implementation 30：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 15.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 5h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 30 shown in.
Case study on implementation 31：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 25.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 5h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 31 shown in.
Case study on implementation 32：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 30.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 5h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 32 shown in.
Case study on implementation 33：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 5h in 160 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 33 shown in.
Case study on implementation 34：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 5h in 170 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 34 shown in.
Case study on implementation 35：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 5h in 190 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 35 shown in.
Case study on implementation 36：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 3h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 36 shown in.
Case study on implementation 37：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 4h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 37 shown in.
Case study on implementation 38：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 6h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 38 shown in.
Case study on implementation 39：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.0.2MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 7h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 39 shown in.
Case study on implementation 40：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.0.4MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 5h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 40 shown in.
Case study on implementation 41：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.0.6MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 5h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 41 shown in.
Case study on implementation 42：Catalysis furfural or furfuryl alcohol add hydrogen to prepare cyclopentanone
In a kettle, 0.1000g furfural, 2.0000g deionized water and catalyst Cu is added0.4Mg5.6Al2, and be catalyzed
The amount of agent is 20.0mg, seals reaction kettle.0.8MPa hydrogen is filled with after replacing 3 times with the air in hydrogen replacement reaction kettle.
It is placed in heating reaction 5h in 180 DEG C of heating mantle, is cooled down at room temperature to after reaction, take out reaction kettle from heating mantle and be placed in
It to room temperature, is extracted with ethyl acetate, the conversion ratio of gas chromatographic detection furfural and the selectivity of cyclopentanone.Reaction result is shown in Table 2
In case study on implementation 42 shown in.
Table 1：
| Case study on implementation | Furfural conversion ratio | Cyclopentanol selectivity |
| 4 | 100% | 98% |
| 5 | 100% | 97% |
| 6 | 99% | 85% |
| 7 | 100% | 98% |
| 8 | 93% | 98% |
| 9 | 98% | 98% |
| 10 | 100% | 98% |
| 11 | 100% | 98% |
| 12 | 100% | 75% |
| 13 | 100% | 94% |
| 14 | 100% | 98% |
| 15 | 100% | 83% |
| 16 | 100% | 90% |
| 17 | 100% | 96% |
| 18 | 100% | 98% |
| 19 | 100% | 73% |
| 20 | 100% | 81% |
| 21 | 100% | 98% |
| 22 | 100% | 98% |
| 23 | 100% | 97% |
| 24 | 100% | 93% |
Table 2：
By catalyst filtration in case study on implementation 4 and with acetone washing, reused after dry.Process flow and case study on implementation
4 is consistent, and catalyst recycles service condition such as following table：
| Recovered frequency | Furfural conversion ratio | Cyclopentanol selectivity |
| 1 | 100% | 98% |
| 2 | 99% | 98% |
| 3 | 99% | 97% |
| 4 | 100% | 98% |
| 5 | 100% | 97% |
| 6 | 99% | 98% |
By catalyst filtration in case study on implementation 25 and with acetone washing, reused after dry.Process flow and implementation case
Example 25 is consistent, and catalyst recycles service condition such as following table：
| Recovered frequency | Furfural conversion ratio | Cyclopentanone selectivity |
| 1 | 100% | 98% |
| 2 | 99% | 98% |
| 3 | 100% | 98% |
| 4 | 98% | 98% |
| 5 | 98% | 97% |
| 6 | 99% | 98% |
Claims (7)
1. a kind of method that catalyzed conversion biomass prepares cyclopentanol or cyclopentanone, which is characterized in that use catalyst containing Cu, use
Furfural or furfuryl alcohol are added in autoclave, is filled with hydrogen, reacts and produced under certain reaction temperature for deionization water as solvent
Object cyclopentanol or cyclopentanone.
2. according to the method described in claim 1, it is characterized in that the catalyst containing Cu is CuxMgyAl2Compound, wherein
X/y=0.07-0.25, (x+y)/2=3.
3. according to the method described in claim 1, it is characterized in that the dosage of catalyst is the 10%- of furfural or furfuryl alcohol quality
30%.
4. according to the method described in claim 1, it is characterized in that the quality of deionized water is the 1.6- of furfural or furfuryl alcohol quality
20 times.
5. according to the method described in claim 1, it is characterized in that the dosage of hydrogen is 0.2MPa-4.0MPa.
6. according to the method described in claim 1, it is characterized in that reaction temperature is 160-200 DEG C.
7. according to the method described in claim 1, it is characterized in that the reaction time is 3-21h.
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| CN111253230A (en) * | 2018-11-30 | 2020-06-09 | 中国科学院大连化学物理研究所 | Method for preparing 3-hydroxymethylcyclopentanone by hydrogenating 5-hydroxymethylfurfural under catalysis of water phase |
| CN112661618A (en) * | 2019-10-16 | 2021-04-16 | 中国石油化工股份有限公司 | Copper catalytic preparation method of cyclopentanone |
| CN112898126A (en) * | 2019-11-19 | 2021-06-04 | 中国科学院大连化学物理研究所 | Method for preparing 3-hydroxymethyl cyclopentanol |
| CN115894196A (en) * | 2022-11-17 | 2023-04-04 | 浙江新化化工股份有限公司 | Method for continuously combining cyclopentanone |
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| CN111253230A (en) * | 2018-11-30 | 2020-06-09 | 中国科学院大连化学物理研究所 | Method for preparing 3-hydroxymethylcyclopentanone by hydrogenating 5-hydroxymethylfurfural under catalysis of water phase |
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| CN112661618B (en) * | 2019-10-16 | 2024-04-09 | 中国石油化工股份有限公司 | Copper catalysis preparation method of cyclopentanone |
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| CN115894196A (en) * | 2022-11-17 | 2023-04-04 | 浙江新化化工股份有限公司 | Method for continuously combining cyclopentanone |
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