CN102344424B - Method for preparing furfurylideneacetone and di-furfurylideneacetone from furfural - Google Patents
Method for preparing furfurylideneacetone and di-furfurylideneacetone from furfural Download PDFInfo
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- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 title claims abstract description 74
- GBKGJMYPQZODMI-SNAWJCMRSA-N (e)-4-(furan-2-yl)but-3-en-2-one Chemical compound CC(=O)\C=C\C1=CC=CO1 GBKGJMYPQZODMI-SNAWJCMRSA-N 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title claims abstract description 16
- XOOFLVNFEPIPIW-UHFFFAOYSA-N 1,5-bis(furan-2-yl)penta-1,4-dien-3-one Chemical compound C=1C=COC=1C=CC(=O)C=CC1=CC=CO1 XOOFLVNFEPIPIW-UHFFFAOYSA-N 0.000 title abstract 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 239000007787 solid Substances 0.000 claims abstract description 11
- 239000007788 liquid Substances 0.000 claims abstract description 9
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 238000002390 rotary evaporation Methods 0.000 claims description 9
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- 239000002808 molecular sieve Substances 0.000 claims description 6
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 6
- 238000007605 air drying Methods 0.000 claims description 5
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical group O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007810 chemical reaction solvent Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims 1
- 230000008901 benefit Effects 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000000926 separation method Methods 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- 239000003513 alkali Substances 0.000 abstract description 3
- 239000012295 chemical reaction liquid Substances 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 238000000605 extraction Methods 0.000 abstract description 3
- 238000005882 aldol condensation reaction Methods 0.000 abstract description 2
- 238000001704 evaporation Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 18
- 239000002585 base Substances 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
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- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000005057 refrigeration Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 241000722917 Cacosmia Species 0.000 description 1
- 238000003512 Claisen condensation reaction Methods 0.000 description 1
- 208000012898 Olfaction disease Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000013521 mastic Substances 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 235000019546 parosmia Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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Abstract
The invention discloses a method for preparing furfurylideneacetone and di-furfurylideneacetone from furfural by catalyzing with a solid alkali catalyst and a separating process. In the process, furfurylideneacetone and di-furfurylideneacetone are prepared by undergoing an aldol condensation reaction on furfural and acetone serving as raw materials and taking 'water-alcohol' or 'water-methanol' as a solvent under the catalyzing action of solid alkali. Di-furfurylideneacetone can be directly separated by refrigerating a reaction liquid at low temperature and crystalizing; and furfurylideneacetone can be further separated out by rotationally evaporating a residual liquid in vacuum and crystalizing. The purities of the two products are over 98percent, and the total yield is up to 55.4 percent. The method has the advantages of mild reaction conditions, simple separation and extraction processes, high overall yield, capability of realizing comprehensive utilization of two kinds of products, environmentally-friendly production process and high economic benefit and environmental benefit.
Description
Technical field:
The present invention relates to technical field of chemistry, relate in particular to the method that a kind of solid base catalyst catalysis furfural prepares furfurylidene-acetone and two furfurylidene-acetones.
Technical background
Furfurylidene-acetone [4-(2-furyl)-3-butene-2-ketone], be called for short FA, it is a kind of resin monomer, can be used for making chemical industry, metallurgy and the building fields such as plastic concrete, furan mastic, furan nucleus epoxy resins of resistance to chemical attack, also is a kind of important organic chemistry product and spices fine-chemical intermediate simultaneously.
Two furfurylidene-acetones [1,5-pair-(2-furans)-1,4-pentadiene-3-ketone], be called for short F2A, it is a kind of a rubber crosslinker, be known as VP-4, the co-crosslinker (also being activator or the cocuring agent of superoxide) that can be used as rubber and plastics superoxide, be mainly used in the activation of peroxide crosslinking product, and rate of crosslinking and physical strength increase with superoxide than single all, also can be with low-molecular polyethylene wax and with (3: 1), substitute the sulphur in Ethylene Propylene Terpolymer and the production of other glue class, cacosmia flavor in the time of can eliminating the processing sulfuration, vulcanization rate is fast simultaneously, can make odorlessness, heat-resisting, the vulcanizing agent that stress at definite elongation is high.
In addition, (science according to the literature, 2005,308,1446-1450), furfurylidene-acetone (FA) and two furfurylidene-acetones (F2A) and derivative thereof can make Aviation Fuel component (C8-C15 long chain alkane) by hydrogenation, dehydration, hydrogenation technique, can replace traditional fossil oil to be applied to the supply respect of aviation power fuel.
Typical FA and F
2The A synthesis technique is to be that raw material carries out the Claisen condensation reaction under the katalysis of alkali with furfural and acetone.Reaction path is as follows:
Aldol condensation takes place with the acetone that contains a-H and generates FA in furfural under base catalysis, almost a part FA can generate F with the further condensation of the furfural of another molecule simultaneously
2A, wherein FA and F2A are the primary products of this reaction.The preparation method of furfurylidene-acetone that at present only a small amount of bibliographical information arranged, and to adopt liquid bases such as NaOH, KOH or ammoniacal liquor be Preparation of catalysts technology more, but this technology has stronger corrodibility and contaminative, is not a kind of green production process.And do not see pertinent literature and patent report as yet for the preparation method of two furfurylidene-acetones.
Summary of the invention:
The object of the invention is to provide a kind of green production method for preparing furfurylidene-acetone and two furfurylidene-acetones simultaneously.Can realize the high purity separation to these two kinds of products, improve utilization ratio of raw materials to greatest extent and reduce the discharging wastes amount.
For achieving the above object, the present invention has taked following technical scheme:
The raw material that the present invention adopts is: furfural and acetone.
The catalyzer that the present invention adopts is: the MgO/NaY catalyst system.The technology that above-mentioned solid base catalyst has been reported for existing document.
The present invention adopts alkaline earth metal oxide MgO and NaY molecular sieve catalyst to form solid base catalyst; Be solvent with water-ethanol or water-methanol, make furfural and condensation of acetone generate furfurylidene-acetone and two furfurylidene-acetones; Reaction solution obtains two furfurylidene-acetones through deepfreeze, crystallization, and residual solution obtains furfurylidene-acetone through rotary evaporation in vacuo, deepfreeze, crystallization.
The inventive method step of specifically planting is as follows:
Need before using that furfural is carried out underpressure distillation and purify, avoid atmospheric oxidation to form furancarboxylic acid, and it is stand-by to collect 110～120 ℃ of cuts under the state of vacuumizing.
1) preparation of solid base catalyst: adopt alkaline earth metal oxide MgO and NaY molecular sieve catalyst to form solid base catalyst.
This step can further be refined as:
Lightweight MgO and NaY molecular sieve are mixed by a certain percentage, grind evenly, under air atmosphere, be warming up to 600 degree roasting 4h with 5～20 ℃/min.Namely can be made into compound MgO/NaY catalyzer.
The content of alkaline earth metal oxide MgO is 20wt%～50wt% in the solid base catalyst.
2) furfurylidene-acetone and two furfurylidene-acetones is synthetic: be solvent with water-ethanol or water-methanol, make furfural and condensation of acetone generate furfurylidene-acetone and two furfurylidene-acetones.
This step can further be refined as:
Being 0.5～3.0 to take by weighing furfural and acetone according to the mol ratio of furfural and acetone, is that solvent is made into the reaction solution that furfural concentration is 4.5wt%～12.8wt% with aqueous ethanolic solution or methanol aqueous solution.The amount that catalyzer adds is the 7.3wt%～40wt% of furfural.Temperature of reaction is 80～140 ℃, and the reaction times is 4～12h.Reaction is left standstill cooling after finishing, and reclaims catalyzer, collects reaction solution.
Used reaction solvent is water-ethanol or water-methanol, and its volumetric concentration is 30%～60%.
3) separation of two furfurylidene-acetones is purified: reaction solution obtains two furfurylidene-acetones through deepfreeze, crystallization.
This step can further be refined as:
Adopt the water-ethanol solvent system can directly realize the separation of two furfurylidene-acetones is purified.Method is that above-mentioned reaction solution is refrigerated 4～12h at 3～-10 ℃, and two furfurylidene-acetones can be separated out with crystalline form, and it is separated, and can obtain the glassy yellow acicular crystals.Crystal is through natural air drying, and not needing recrystallization can obtain purity is two furfurylidene-acetones more than 98%, and extraction yield can reach 60%～80%.
4) separation of furfurylidene-acetone is purified: after residual solution is removed reaction solvent, reclaim liquid through 90～120 ℃ of rotary evaporation in vacuo and collection, deepfreeze, crystallization obtain furfurylidene-acetone.
This step can further be refined as:
Take similar crystallization method to be difficult to directly from the reaction solution of remnants, purify furfurylidene-acetone.The present invention has developed the extracting method of a kind of " rotary evaporation in vacuo-low temperature crystallization ", has effectively realized extracting furfurylidene-acetone from the residual solution of having separated two furfurylidene-acetones.After residual solution is removed reaction solvent, reclaim liquid through 90～120 ℃ of rotary evaporation in vacuo and collection, deepfreeze, crystallization obtain furfurylidene-acetone.Concrete grammar is as follows: above-mentioned residual reaction liquid is carried out rotary evaporation in vacuo, earlier at 50～70 ℃ of alcohol solvents that reclaim down in the reaction solution.Be warming up to 90～120 ℃ of continuation then residual reaction liquid is carried out rotary evaporation in vacuo, this moment, furfurylidene-acetone can be condensate in the returnable bottle after coming along with water vapor is steamed.To reclaim liquid at 3～-10 ℃ of refrigeration 1～4h, furfurylidene-acetone can be separated out with crystalline form, again it is carried out suction filtration, and natural air drying can obtain the needle-like light yellow crystal, and purity reaches more than 98%, and extraction yield can reach 60%～80%.
Technological reaction mild condition of the present invention, process for separating and purifying is simple, and the overall productivity height can be realized the comprehensive utilization of two kinds of products, and the whole process of production environmental protection has high economic benefit and environmental benefit.
Description of drawings:
Two furfurylidene-acetones that Fig. 1 obtains for the embodiment of the invention 1
1The H-NMR collection of illustrative plates;
The furfurylidene-acetone that Fig. 2 obtains for the embodiment of the invention 1
1The H-NMR collection of illustrative plates;
The two furfurylidene-acetone MS collection of illustrative plates that Fig. 3 obtains for the embodiment of the invention 1;
The furfurylidene-acetone MS collection of illustrative plates that Fig. 4 obtains for the embodiment of the invention 1;
The two furfurylidene-acetone IR collection of illustrative plates that Fig. 5 obtains for the embodiment of the invention 1;
The furfurylidene-acetone IR collection of illustrative plates that Fig. 6 obtains for the embodiment of the invention 1.
Embodiment:
Need before using that furfural is carried out underpressure distillation and purify, avoid atmospheric oxidation to form furancarboxylic acid, and it is stand-by to collect 110～120 ℃ of cuts under the state of vacuumizing.
Lightweight MgO and NaY molecular sieve are mixed in proportion, grind evenly, under air atmosphere, be warming up to 600 degree roasting 4h with 5～20 ℃/min.Namely can be made into compound MgO/NaY catalyzer.The content of alkaline earth metal oxide MgO is 20wt%～50wt% in the solid base catalyst.
Embodiment 1:
Be that 50% aqueous ethanolic solution mixes with 4.8g furfural (0.05mol), 2.9g acetone (0.05mol) and 1.06g 20%-MgO/NaY catalyzer and 95.4g (105ml) volumetric concentration, furfural concentration is 4.6wt%, put in the there-necked flask reactor of being furnished with reflux column, oil bath is heated to 100 ℃, reaction 8h.After question response finishes, cooling 30min, vacuum filtration, separating catalyst is collected reaction solution.The reaction solution of collecting is transferred to temperature and is set to behind the refrigeration 8h it be carried out suction filtration in-3 ℃ the refrigerator, collects the xln on the filter paper, and room temperature is after air-dry for some time, weigh two furfurylidene-acetone 2.45g.
Remaining reaction solution moved to revolve send out an instrument, fully reclaim ethanol down at 60 ℃, question response liquid occurs yellow when muddy, and the ethanolic soln in the returnable bottle is removed.Be warming up to 120 ℃ then, continue rotary evaporation in vacuo, the recovery liquid of collecting is moved to-3 ℃ of refrigerator cold-storage 4h, carry out vacuumizing filtration to reclaiming liquid again, filter crystal through natural air drying, weigh furfurylidene-acetone 1.82g.Overall yield is 55.4%.
Embodiment 2:
Be that 40% aqueous ethanolic solution mixes with 4.8g furfural (0.05mol), 2.9g acetone (0.05mol) and 1.06g 20%-MgO/NaY catalyzer and 95.4g (105ml) volumetric concentration, furfural concentration is 4.6wt%, at 100 ℃ of reaction 8h down.All the other steps are identical with embodiment 1, collect two furfurylidene-acetone 2.54g, furfurylidene-acetone 1.68g, and overall yield is 54.8%.
Getting 4.8g furfural (0.05mol), 5.8g acetone (0.1mol) and 1.06g 50%-MgO/NaY catalyzer and 95.4g (105ml) volumetric concentration and be 50% aqueous ethanolic solution mixes, furfural concentration is 4.5wt%, react 8h down at 100 ℃, all the other steps are identical with embodiment 1, collect two furfurylidene-acetone 2.35g, furfurylidene-acetone 1.78g, overall yield is 38.9%.
Getting 4.8g furfural (0.05mol), 2.9g acetone (0.05mol) and 1.06g 20%-MgO/NaY catalyzer and 95.4g (105ml) volumetric concentration and be 40% methanol aqueous solution mixes, furfural concentration is 4.6wt%, react 8h down at 100 ℃, all the other steps are identical with embodiment 1, collect two furfurylidene-acetone 2.04g, furfurylidene-acetone 1.48g, overall yield is 33.2%.
Be that 40% methanol aqueous solution mixes with 9.6g furfural (0.10mol), 2.9g acetone (0.05mol) and 1.06g 20%-MgO/NaY catalyzer and 95.4g (105ml) volumetric concentration, furfural concentration is 8.7wt%, at 100 ℃ of reaction 8h down.All the other steps are identical with embodiment 1, collect two furfurylidene-acetone 3.17g, furfurylidene-acetone 1.02g, and overall yield is 33.5%.
Be that 40% methanol aqueous solution mixes with 14.4g furfural (0.15mol), 2.9g acetone (0.05mol) and 1.06g 20%-MgO/NaY catalyzer and 95.4g (105ml) volumetric concentration, furfural concentration is 12.8wt%, at 100 ℃ of reaction 8h down.All the other steps are identical with embodiment 1, collect two furfurylidene-acetone 4.32g, furfurylidene-acetone 0.83g, and overall yield is 29.8%.
Embodiment 7
Be that 40% methanol aqueous solution mixes with 4.8g furfural (0.05mol), 2.9g acetone (0.05mol) and 1.92g 20%-MgO/NaY catalyzer and 95.4g (105ml) volumetric concentration, furfural concentration is 4.6wt%, at 100 ℃ of reaction 8h down.All the other steps are identical with embodiment 1, collect two furfurylidene-acetone 2.60g, furfurylidene-acetone 1.54g, and overall yield is 53.7%.
Claims (1)
1. one kind prepares the method for furfurylidene-acetone and two furfurylidene-acetones by furfural, is raw material with furfural and acetone, it is characterized in that may further comprise the steps:
(1) adopt alkaline earth metal oxide MgO and NaY molecular sieve catalyst to form solid base catalyst, the content of alkaline earth metal oxide MgO is 20wt%～50wt% in the described solid base catalyst, prepare through following method: lightweight MgO and NaY molecular sieve are mixed in proportion, grind evenly, under air atmosphere, be warming up to 600 degree roasting 4h with 5～20 ℃/min; Namely can be made into compound MgO/NaY catalyzer;
(2) make furfural and condensation of acetone generate furfurylidene-acetone and two furfurylidene-acetones, the mol ratio of furfural and acetone is 0.5～3.0, furfural concentration is 4.5wt%～12.8wt%, the amount that catalyzer adds is the 7.3wt%～40wt% of furfural, temperature of reaction is 80～140 ℃, reaction times is 4～12h, and used reaction solvent is water-ethanol or water-methanol, and its volumetric concentration is 30%～60%;
(3) after reaction finished, reaction solution was through 3～-10 ℃ of deepfreeze 4～12h, and two furfurylidene-acetones can be separated out with crystalline form, namely obtained two furfurylidene-acetone crystal of purity 〉=98% after separating behind the natural air drying;
(4) carry out rotary evaporation in vacuo to separating two furfurylidene-acetone residual solution, earlier at 50～70 ℃ of ethanol or methanol solvates that reclaim down in the reaction solution, be warmed up to 90～120 ℃ then and continue rotary evaporation, with the recovery liquid collected at 3～-10 ℃ of deepfreeze 1～4h, furfurylidene-acetone can be separated out with crystalline form, namely obtains the furfurylidene-acetone crystal of purity 〉=98% after separating behind the natural air drying.
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| CN108658903B (en) * | 2017-03-30 | 2020-11-13 | 中国石油化工股份有限公司 | Difurfurylideneacetone chemical product and preparation method thereof |
| CN107570133B (en) * | 2017-10-18 | 2021-03-23 | 湘潭大学 | Spherical mesoporous solid acid-base bifunctional catalyst and preparation method and application thereof |
| CN108727943B (en) * | 2018-04-27 | 2021-06-08 | 中科院广州化学有限公司南雄材料生产基地 | Organic silicon fluorine modified epoxy resin, organic silicon fluorine sol furfural acetone composite modified epoxy coating material and preparation method thereof |
| CN109603795B (en) * | 2018-12-13 | 2022-01-07 | 万华化学集团股份有限公司 | Solid base catalyst and production process for preparing 4- (2-furyl) -3-butylene-2-ketone |
| CN109759046A (en) * | 2019-01-25 | 2019-05-17 | 中国科学院过程工程研究所 | A kind of load type solid body base catalyst, preparation method and the method that furfurylidene-acetone and two furfurylidene-acetones are prepared by furfural and acetone |
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