CN104327005A - Method for preparing scintillation pure grade 2,5-diphenyl oxazole - Google Patents
Method for preparing scintillation pure grade 2,5-diphenyl oxazole Download PDFInfo
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- CN104327005A CN104327005A CN201410561495.5A CN201410561495A CN104327005A CN 104327005 A CN104327005 A CN 104327005A CN 201410561495 A CN201410561495 A CN 201410561495A CN 104327005 A CN104327005 A CN 104327005A
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- CNRNYORZJGVOSY-UHFFFAOYSA-N 2,5-diphenyl-1,3-oxazole Chemical compound C=1N=C(C=2C=CC=CC=2)OC=1C1=CC=CC=C1 CNRNYORZJGVOSY-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 10
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 15
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 238000010719 annulation reaction Methods 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- -1 compound acyl chloride Chemical class 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000005580 one pot reaction Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 238000011084 recovery Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000010907 mechanical stirring Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 0 *C(CNC(c1ccccc1)=O)=O Chemical compound *C(CNC(c1ccccc1)=O)=O 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- MIJZKZQWQXKSPA-UHFFFAOYSA-N O=C(CNC(c1ccccc1)=O)c1ccccc1 Chemical compound O=C(CNC(c1ccccc1)=O)c1ccccc1 MIJZKZQWQXKSPA-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for preparing scintillation pure grade 2,5-diphenyl oxazole (DPO or PPO for short). The method comprises the following steps: by taking benzoyl glycine as a raw material, performing multiple steps of reaction such as acylating chlorination, Frieldel-Crafts and ring formation, purifying middle products of each step without being separated, and preparing 2,5-diphenyl oxazole by using a one-pot method. An obtained product can be rectified and purified, the requirements of a scintillator cannot be met but metal oxide heating treatment is needed, and thus a 2,5-diphenyl oxazole product for scintillation fluor can be obtained. As the one-pot method is adopted to prepare 2,5-diphenyl oxazole, the reaction steps are reduced, the operation process is simplified, the production efficiency is improved, a purification method is simple, convenient and effective, and on-scale industrialization production is achieved.
Description
Technical field
The present invention relates to field of fine chemical, be specifically related to a kind of preparation method of 2，5-diphenyloxazole (DPO or PPO) of pure rank of glimmering.
Background technology
Organic scintillator is a kind of test material very important in national defence scientific research, it is under the exciting of high-energy electromagnetic radiation line, can send of short duration fluorescence, be amplified by photomultiplier, anode causes voltage pulse, passes on to get off into recorder trace through differentiation device.Scintillometer, scintillation spectrometer is exactly the equipment utilizing this principle to carry out work.Organic scintillator is indispensable operation material in scintillometer, and liquid scintillation counting(LSC) technology is the new measuring technology just grown up over nearly more than 30 years in the world, and it is employed for various scientific domain more and more.
2，5-diphenyloxazole, as the one of organic scintillator, has been applied in national defence scientific research project and basic scientific research.But the production of the pure rank 2，5-diphenyloxazole that do not glimmer at present, can not meet the needs of growing scientific research, therefore the effective purifying of improving technique becomes the new direction of such subject study.
For the preparation of 2，5-diphenyloxazole, document (chemistry world, the 9th phase in 1994,460-463) adopts methyl phenyl ketone to be initial feed, and obtain target compound by steps such as bromination, replacement, salify, addition, Cheng Huan, reaction equation is:
It is low that the method prepares target product yield, and total recovery is 39.8%, and condition is harsh, and pollute large, especially in bromination process, use bromine, toxicity is large, and corrodibility is strong, and long reaction time, energy consumption is high.On the method products therefrom and market, product sold does not all reach the pure levels necessitate of flicker.
Summary of the invention
The technical problem to be solved in the present invention is: provide that a kind of reaction conditions is gentle, technology and equipment simple, the preparation method of the 2，5-diphenyloxazole of the pure rank of flicker of convenient operation.
The present invention for solving the problems of the technologies described above taked technical scheme is:
The preparation method of the 2，5-diphenyloxazole of pure rank of glimmering, is characterized in that, this preparation method takes one kettle way to prepare 2，5-diphenyloxazole crude product, then by gained crude product with metal oxide treated, namely the 2，5-diphenyloxazole of the pure rank of described flicker is obtained.
In such scheme, described one kettle way is with hippuric acid, takes chloride successively, to pay gram and annulation synthesis 2，5-diphenyloxazole crude product.
In such scheme, described one kettle way prepare that formula I represents 2,5-diphenyl-oxazole, compound acyl chloride reaction shown in formula II is obtained compound shown in formula III, compound (III) is obtained by reacting formula IV compound without separation and benzene, and formula IV compound is obtained by reacting formula I target compound without separation direct hydrolysis:
In such scheme, described one kettle way of taking prepares 2，5-diphenyloxazole, specifically obtains in accordance with the following steps:
1) in reactor, hippuric acid (II) and sulfur oxychloride is added, hippuric acid (II) is 1:2 with the mol ratio of sulfur oxychloride, at 30-80 DEG C after completion of the reaction, steam unreacted sulfur oxychloride, obtain hippuryl chlorine (III);
2) directly to adding benzene and aluminum chloride in reactor, the mol ratio of benzene, aluminum chloride and compound (II) is 10:(1.5-3): 1, reflux 1-5 hour, obtains N-benzoyl-omega-amino-methyl phenyl ketone (VI);
3) directly to adding 50wt% sulfuric acid in reactor, the mol ratio of sulfuric acid and compound (II) is 2:1, and temperature of reaction controls 100 DEG C, after completion of the reaction, steam excessive benzene, in reactor, drip water, the dropping water yield and 50wt% sulfuric acid mass ratio are 4:1, control temperature of charge 30-50 DEG C, filter, rectifying, obtains 2，5-diphenyloxazole (I) white solid.
In such scheme, described crude product is dissolved with alkyl benzene solvent by 2，5-diphenyloxazole with the step of metal oxide treated, add metal oxide and gac, stir 3 hours at 100-120 DEG C, millipore filtration, crystallize out after filtration, obtains 2，5-diphenyloxazole sterling.
In such scheme, the mass ratio of described alkylbenzene, metal oxide and gac and treating material 2，5-diphenyloxazole is 4:(0.01-0.05): (0.005-0.03): 1.
In such scheme, the aperture of described millipore filtration is 0.1-2 μm.
Compared with prior art, beneficial effect of the present invention is:
1, overcome complex operation in prior art, be unsuitable for the shortcoming of suitability for industrialized production.
2, be that raw material adopts one pot process 2，5-diphenyloxazole, total recovery 88.4% with hippuric acid.Yield is high, and greatly simplifies operating process, improves production efficiency.
3, prior art can not obtain the product being applied to organic scintillator, adopts metal oxide treated, overcomes existing Technology defect, obtain high-quality product.
4, safety and environmental protection, environmental pollution is less.
Embodiment
Below in conjunction with embodiment, the invention will be further described, and certain following embodiment should not be construed as limitation of the present invention.
Embodiment 1
To there being mechanical stirring, in the 5000L enamel reactor of thermometer, add hippuric acid (II) (179kg, 1kmol) with sulfur oxychloride (238kg, 2kmol), react at 50 DEG C, sampling monitoring is complete to compound (II) total overall reaction, distill out unreacted sulfur oxychloride, obtain hippuryl chlorine (III), be cooled to 50 DEG C, benzene (780kg is added in reactor, 10kmol) with aluminum chloride (267kg, 2kmol), reflux 3 hours, gained N-benzoyl-omega-amino-methyl phenyl ketone (VI) reaction solution is cooled to 30 DEG C, add 50wt% sulfuric acid (392kg, 2kmol), slowly be warming up to 100 DEG C, react complete at this temperature, steam excessive benzene, reaction solution is cooled to 30 DEG C, water (1568kg) is added dropwise in reactor, adularescent solid is separated out, filter, rectifying, obtain 2, 5-diphenyl-oxazole (I) about 202kg, yield 91.4%, content 99.3% (HPLC), analyzing and testing does not reach the pure rank of flicker, can not use as organic scintillator.Fusing point: 72.2-73.5 DEG C.1H-NMR(CDCl3，400MHZ)δ：7.33(1H,S)，7.43-7.48(6H，m)，7.71(2H，m)，8.11(2H，m)。MS(EI，m/z)：(221.0，165.0，89.0，77.0)。
In the present invention, each embodiment is all tested with this liquid phase chromatographic analysis method (HPLC): chromatographic column (Eclipse XDB-C8,5 μm, 4.6*150mm), flow velocity (1.2mL/min), wavelength (222nm), column temperature (25 DEG C), elution time (15min), moving phase and program (0-3min, acetonitrile: phosphoric acid buffer=25%:75%; 3-7min, acetonitrile: phosphoric acid buffer=40%:60%; 7-15min, acetonitrile: phosphoric acid buffer=65%:35%).
Embodiment 2
Other steps are identical with embodiment 1, and just gained 2，5-diphenyloxazole purification process is as follows:
According to the synthetic method obtained 2 of embodiment 1, 5-diphenyl-oxazole (150kg), put in 1000L stainless steel cauldron, add toluene (600kg), croci (3kg), gac (1.5kg), stir, open steam heating, 3h is stirred at 110 DEG C, be cooled to 25 DEG C, hay tank solids removed by filtration, filtered by millipore filter (aperture is 0.5 μm) again, steam except after toluene solvant, obtain 2, 5-diphenyl-oxazole 145kg, purification yield 96.7%, content 99.8% (HPLC), fusing point: 72.3-73.5 DEG C, analyzing and testing reaches scintillation fluor agent requirement, can use as organic scintillator.
Embodiment 3
Purification experiment is carried out by the method identical with embodiment 2, unlike, add nickel oxide powder (3kg) and replace croci, dimethylbenzene replaces toluene, obtains 2,5-diphenyl-oxazole 145.3kg, purification yield 96.9%, content 99.8% (HPLC), fusing point 72.2-73.5 DEG C, analyzing and testing reaches scintillation fluor agent requirement, can use as organic scintillator.
Comparative example 1
Take document (chemistry world, 9th phase in 1994, preparation method 460-463), with methyl phenyl ketone be raw material through five step building-up reactionss, obtain 2,5-diphenyl-oxazole product, total recovery 35.2%, content 99.1% (HPLC), fusing point 70.3-71.6 DEG C, fusing point is on the low side, and products therefrom detects by analysis and do not reach the pure rank of flicker.
Comparative example 2
To in the reactor being provided with mechanical stirring device, mercurythermometer, add hippuric acid (17.9g), phosphorus pentachloride (30g), be warming up to 150 DEG C, react 2 hours, sampling analysis detects, and when after completion of the reaction, reaction solution is cooled to 80 DEG C, stratification, upper organic phase is hippuroyl chlorine.
Above product is joined in reactor and be uniformly mixed with benzene (120g) and aluminum chloride (30g), reflux 4 hours.After completion of the reaction, being cooled to 20 DEG C, is that the hydrochloric acid (30g) of 30% mixes slowly to add in reaction solution with ice (50g) and carries out ice solution by concentration; drip process control temperature of charge 20 DEG C; after dropwising, continue stirring 1 hour, suction filtration; obtain product N-benzoyl-omega-amino-methyl phenyl ketone (VI) crude product; with recrystallizing methanol, dry, obtain fine work product 18.3g; yield 76.7%, content 99.5% (HPLC).
To in the reactor being provided with mechanical stirring device, mercurythermometer, add N-benzoyl-omega-amino-methyl phenyl ketone (20g) and sulfuric acid (80g), be uniformly mixed; control temperature of reaction 80 DEG C, stirring reaction 2 hours, after completion of the reaction; extract 3 times with toluene, merge organic phase, steam except toluene; obtain product 2; 5-diphenyl-oxazole yellow solid, with recrystallizing methanol, obtains white fine work product 11.6g; yield 62.5%, content 99.7% (HPLC).
Multistep processes prepares 2，5-diphenyloxazole, and the method for recrystallizing methanol is taked in aftertreatment, total recovery be 47.9% products therefrom detect by analysis do not reach flicker pure rank.
Comparative example 3
Other steps are identical with comparative example 2, purification process takes document (chemistry world, 9th phase in 1994, method 460-463), by obtained yellow crude, carry out rectifying, rectifying temperature of charge control 240-260 DEG C, vacuum control 20-50Pa, the rectifying time-division gets three cuts, front-end volatiles and after cut are faint yellow, and main distillate fraction is colourless, are added by the main distillate fraction of molten state in 60-90 DEG C of sherwood oil, cool overnight, obtain white solid 13.2g, yield 71.1%, content 99.6% (HPLC).
Take multistep processes to prepare 2，5-diphenyloxazole, products obtained therefrom takes rectifying and sherwood oil process, total recovery 54.5%, and products therefrom detects by analysis and do not reach the pure rank of flicker.
In specification sheets by object lesson to invention has been detailed description, but those skilled in the art is within the scope of scope of the present invention and technological thought, can carry out various distortion and change to the present invention, these distortion and change also belong within right of the present invention.
Claims (7)
1. the preparation method of the 2，5-diphenyloxazole of pure rank of glimmering, is characterized in that, this preparation method takes one kettle way to prepare 2，5-diphenyloxazole crude product, then by gained crude product with metal oxide treated, namely the 2，5-diphenyloxazole of the pure rank of described flicker is obtained.
2. preparation method according to claim 1, is characterized in that, described one kettle way is with hippuric acid, takes chloride successively, to pay gram and annulation synthesis 2，5-diphenyloxazole crude product.
3. preparation method according to claim 1, it is characterized in that, described one kettle way prepare that formula I represents 2,5-diphenyl-oxazole, compound acyl chloride reaction shown in formula II is obtained compound shown in formula III, compound (III) is obtained by reacting formula IV compound without separation and benzene, and formula IV compound is obtained by reacting formula I target compound without separation direct hydrolysis:
4. preparation method according to claim 3, is characterized in that, described one kettle way of taking prepares 2，5-diphenyloxazole, specifically obtains in accordance with the following steps:
1) in reactor, hippuric acid (II) and sulfur oxychloride is added, hippuric acid (II) is 1:2 with the mol ratio of sulfur oxychloride, at 30-80 DEG C after completion of the reaction, steam unreacted sulfur oxychloride, obtain hippuryl chlorine (III);
2) directly to adding benzene and aluminum chloride in reactor, the mol ratio of benzene, aluminum chloride and compound (II) is 10:(1.5-3): 1, reflux 1-5 hour, obtains N-benzoyl-omega-amino-methyl phenyl ketone (VI);
3) directly to adding 50wt% sulfuric acid in reactor, the mol ratio of sulfuric acid and compound (II) is 2:1, and temperature of reaction controls 100 DEG C, after completion of the reaction, steam excessive benzene, in reactor, drip water, the dropping water yield and 50wt% sulfuric acid mass ratio are 4:1, control temperature of charge 30-50 DEG C, filter, rectifying, obtains 2，5-diphenyloxazole (I) white solid.
5. preparation method according to claim 1, it is characterized in that, described crude product is by 2 with the step of metal oxide treated, 5-diphenyl-oxazole dissolves with alkyl benzene solvent, adds metal oxide and gac, stirs 3 hours at 100-120 DEG C, millipore filtration, crystallize out after filtration, obtains 2，5-diphenyloxazole sterling.
6. preparation method according to claim 5, is characterized in that, the mass ratio of described alkylbenzene, metal oxide, gac and treating material 2，5-diphenyloxazole is 4:(0.01-0.05): (0.005-0.03): 1.
7. preparation method according to claim 5, is characterized in that, the aperture of described millipore filtration is 0.1-2 μm.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117025699A (en) * | 2023-08-01 | 2023-11-10 | 泰州学院 | Synthesis method of larotinib key intermediate |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1137729A1 (en) * | 1983-12-26 | 1997-10-20 | Н.А. Борисевич | 3- or 4-(5-phenyloxazolyl-2)-tolan as violet luminescence luminophore |
| WO2000020475A1 (en) * | 1998-10-05 | 2000-04-13 | The Nottingham Trent University | Solid supports containing scintillant |
| CN1458925A (en) * | 2000-08-18 | 2003-11-26 | 森斯普罗特米克有限公司 | Lipo-or amphlic scintillators and their use in assays |
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- 2014-10-21 CN CN201410561495.5A patent/CN104327005B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1137729A1 (en) * | 1983-12-26 | 1997-10-20 | Н.А. Борисевич | 3- or 4-(5-phenyloxazolyl-2)-tolan as violet luminescence luminophore |
| WO2000020475A1 (en) * | 1998-10-05 | 2000-04-13 | The Nottingham Trent University | Solid supports containing scintillant |
| CN1458925A (en) * | 2000-08-18 | 2003-11-26 | 森斯普罗特米克有限公司 | Lipo-or amphlic scintillators and their use in assays |
Non-Patent Citations (2)
| Title |
|---|
| BRUCE CLAPHAM 等: "Synthesis and Scintillating Efficiencies of 4-Functionalised-2,5-Diphenyloxazoles", 《TETRAHEDRON LETTERS》 * |
| 陈鸿彬 等: "有机闪烁剂2，5－二苯基噁唑（DPO）生产工艺的探讨", 《化学世界》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117025699A (en) * | 2023-08-01 | 2023-11-10 | 泰州学院 | Synthesis method of larotinib key intermediate |
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