CN103755536A - Method for preparing benzyl by simple oxidation of benzoin - Google Patents
Method for preparing benzyl by simple oxidation of benzoin Download PDFInfo
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- CN103755536A CN103755536A CN201410036899.2A CN201410036899A CN103755536A CN 103755536 A CN103755536 A CN 103755536A CN 201410036899 A CN201410036899 A CN 201410036899A CN 103755536 A CN103755536 A CN 103755536A
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- 238000000034 method Methods 0.000 title claims abstract description 23
- 230000003647 oxidation Effects 0.000 title claims abstract description 22
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 22
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 title abstract 6
- 244000028419 Styrax benzoin Species 0.000 title abstract 3
- 235000000126 Styrax benzoin Nutrition 0.000 title abstract 3
- 235000008411 Sumatra benzointree Nutrition 0.000 title abstract 3
- 229960002130 benzoin Drugs 0.000 title abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 title abstract 3
- 235000019382 gum benzoic Nutrition 0.000 title abstract 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000000741 silica gel Substances 0.000 claims abstract description 10
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims description 22
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 17
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 claims description 15
- 241000723346 Cinnamomum camphora Species 0.000 claims description 14
- 229960000846 camphor Drugs 0.000 claims description 14
- 229930008380 camphor Natural products 0.000 claims description 14
- 239000000377 silicon dioxide Substances 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- YSHOWEKUVWPFNR-UHFFFAOYSA-N burgess reagent Chemical compound CC[N+](CC)(CC)S(=O)(=O)N=C([O-])OC YSHOWEKUVWPFNR-UHFFFAOYSA-N 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- PPNKDDZCLDMRHS-UHFFFAOYSA-N dinitrooxybismuthanyl nitrate Chemical compound [Bi+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PPNKDDZCLDMRHS-UHFFFAOYSA-N 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VQRCEOOGEYKTFG-UHFFFAOYSA-L O[Cr](Cl)(=O)=O.N Chemical compound O[Cr](Cl)(=O)=O.N VQRCEOOGEYKTFG-UHFFFAOYSA-L 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- -1 ester compound Chemical class 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/39—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a secondary hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
Abstract
The invention discloses a method for preparing benzyl by performing air oxidation taking silica gel as a carrier on benzoin. The benzoin is immobilized on the silica gel GF254; the benzyl is prepared by performing the air oxidation by heating; the reaction general formula is shown as the specification, wherein Ph is selected from C6H5, p-F-C6H4, p-Cl-C6H4, o-Cl-C6H4, p-Br-C6H4, p-Me-C6H4, p-OMe-C6H4, p-OEt-C6H4, p-CN-C6H4, and other three radial groups shown in the specification.
Description
Technical field
The invention belongs to organic chemical synthesis field, be specifically related to the method that benzil is prepared in the easy oxidation of a kind of bitter almond oil camphor.
Background technology
Benzil is widely used in printing and dyeing and pharmaceutical industry as important Organic Chemicals and organic synthesis intermediate, but also is heterogeneous ring compound, biochemical material and nano material useful building block in synthetic.Many synthetic methods about this compounds have been developed at present, relate to and utilize benzophenone oxidation style [document 1:S.Wolfe, C.F.Ingold, J.Am.Chem.Soc.105 (1983) 7755. document 2:W.C.Cheng, W.Y.Yu, K.K.Cheung, C.M.Che, J.Chem.Soc.Chem.Comm. (1994) 1063.] with reduction [the document 3:U.T.Mueller-Westerhoff of ester compound under transition metal reagent, M.Zhou, J.Org.Chem.59 (1994) 4988.].And the most directly effective means is the oxidation style of bitter almond oil camphor, report has had all kinds of oxygenants to be applied to the oxidation of bitter almond oil camphor recently, relate generally to oxidizing reaction [the document 4:C.Joo being promoted by sodium hydride, S.Kang, S.M.Kim, H.Han, J.W.Yang, TetrahedronLett.51 (2010) 6006.], electrochemical oxidation [document 5:M.Okimoto under KI exists, Y.Takahashi, Y.Nagata, G.Sasaki, K.Numata, Synthesis (2005) 705.], atmospheric oxidation [document 6:M.Kirihara under vanadium oxytrichloride catalysis, Y.Ochiai, S.Takizawa, H.Takahata, H.Nemoto, Chem.Commun. (1999) 1387.], Bismuth trinitrate (III)-venus crystals (II) catalytic air oxidation method [document 7:S.A.Tymonko, B.A.Nattier, R.S.Mohan, TetrahedronLett.40 (1999) 7657.], Ferric Chloride oxidation style [document 8:W.Y.Sun, N.Ueyama, A.Nakamura, Tetrahedron49 (1993) 1357.], FeCl3/ polynite K10 microwave radiation air oxidation process [document 9:C.Y.Xing, J.T.Li, H.X.Wang, X.L.Li, Chin.J.Org.Chem.25 (2005) 113 (inChinese) .], CrO3-NH4Cl Ultrasonic Radiation oxidation style [document 10:J.T.Li, X.L.Sun, Lett.Org.Chem.3 (2006) 842.], alumina load chloro-chromic acid ammonium air oxidation process [document 11:G.S.Zhang, Q.Z.Shi, M.F.Chen, K.Cai, Synth.Commun.27 (1997) 953.], Burgess reagent oxidation method [document 12:B.Jose, M.V.V.Unni, S.Prathapan, J.J.Vadakkan, Synth.Commun.32 (2002) 2495.], organometallic reagent oxidation style [document 13:Q.Zhang, C.M.Xu, J.X.Chen, X.L.Xu, J.C.Ding, H.Y.Wu, Appl.Organometal.Chem.23 (2009) 524.], solid-phase oxidation method [document 14:F.Toda, Acc.Chem.Res.28 (1995) 480. document 15:Y.M.Zhou, X.R.Ye, X.Q.Xin, Synth.Commun.29 (1999) 2229.].But these methods need to carried out under exacting terms mostly relatively, and a large amount of special oxygenant and the cocatalysts of reaction needed consumption.Meanwhile, the lower and functional group's poor compatibility of the productive rate that has in these methods, post-reaction treatment process is comparatively complicated, reagent cost is high, and the method also having may cause serious environmental problems.
The invention discloses and a kind ofly utilize the oxidation of green air that silica gel is carrier to prepare the method for benzil bitter almond oil camphor.
Summary of the invention
The object of the present invention is to provide the easy oxidation of a kind of bitter almond oil camphor to prepare the method for benzil.
Technical scheme of the present invention is as follows:
By immobilized bitter almond oil camphor, on silica gel, the lower atmospheric oxidation of heating makes benzil, and its reaction expression is shown below:
In formula, Ph is selected from: C
6h
5, p-F-C
6h
4, p-Cl-C
6h
4, o-Cl-C
6h
4, p-Br-C
6h
4, p-Me-C
6h
4, p-OMe-C
6h
4, p-OEt-C
6h
4, p-CN-C
6h
4,
Routine operation is: after bitter almond oil camphor solution is mixed completely with silica gel, evaporation, except desolventizing, is exposed to the mixed powder of gained bitter almond oil camphor and silica gel subsequently in air and suitably and heats until react completely.
Advantage of the present invention and positively effect: this law oxidising process, take air as oxygenant, participates in without other oxygenants or auxiliary, and used carrier silica gel and solvent ethyl acetate are very cheaply easy to get, and have good chemo-selective.React almost contamination-free and produce, solvent for use and carrier easily reclaim also and can reuse, and product all can be able to purifying through simple extraction and recrystallization process.Present method has that productive rate is high, operation and aftertreatment is simple, with low cost, the feature of environmentally safe.
Embodiment
Following synthetic example is used for further illustrating the present invention, but does not mean that restriction the present invention.
The preparation of example 1. compound 2a:
After bitter almond oil camphor (42.4g, 0.2mol) is dissolved completely in 500mL ethyl acetate (or ethanol), in solution, add silica GF254 (500g).Mixture is stirred to completely and is mixed, obtain pulverulent solids except desolventizing vacuumizing under condition evaporation subsequently.Gained powder is placed in to baking oven and contacts with air, oven temperature is risen to 60 ℃, and by thin-layer chromatography (TLC) monitoring reaction process.Mixture is intermittently jolted so that powder stirs up and down.Reaction mixture is through ethyl acetate washing, decompress filter except desolventizing, and resistates obtains 38.9g benzil through dehydrated alcohol recrystallization, productive rate 93%.Silica gel and solvent are all recyclable and be reused for oxidizing reaction.
With reference to the preparation method of 2a, can make other compounds, the results are shown in Table 1.
The preparation of table 1 benzil and productive rate *
* other reaction spare parts: bitter almond oil camphor compounds 2mmol, silica gel 5g, temperature of reaction 60oC.
Infrared and the nuclear-magnetism spectrum data of each product are as follows:
2a:IR(KBr,cm
-1)3064,1660,1594,1579,1450,1325;
1HNMR(500MHz,CDCl
3,δ/ppm):7.98–8.00(m,4H),7.66–8.69(m,2H),7.52–7.55(m,4H);
13CNMR(125MHz,CDCl
3,δ/ppm):129.1,130.0,133.0,135.0,194.7.
2b:IR(KBr,cm
-1)2974,1668,1597,1506,1460,1414;
1HNMR(500MHz,CDCl
3,δ/ppm):8.02–8.05(m,4H),7.19–7.23(m,4H);
13CNMR(125MHz,CDCl
3,δ/ppm):116.5,116.6,129.4,132.86,132.93,165.9,168.0,192.3.
2c:IR(KBr,cm
-1)2923,1662,1587,1543,1487,1401;
1HNMR(500MHz,CDCl
3,δ/ppm):7.92–7.94(m,4H),7.51–7.52(m,4H);
13CNMR(125MHz,CDCl
3,δ/ppm):128.9,129.6,131.3,141.9,192.4.
2d:IR(KBr,cm
-1)3067,1685,1585,1562,1464,1438;
1HNMR(500MHz,CDCl
3,δ/ppm):8.08–8.10(m,2H),7.57–7.60(m,2H),7.46–7.50(m,4H);
13CNMR(125MHz,CDCl
3,δ/ppm):127.4,131.0,132.2,132.8,135.0,135.1,191.1.
2e:IR(KBr,cm
-1)2924,1665,1581,1398,1308,1210;
1HNMR(500MHz,CDCl
3,δ/ppm):7.66–7.68(m,4H),784–7.86(m,4H);
13CNMR(125MHz,CDCl
3,δ/ppm):130.8,131.3,131.6,132.6,192.8.
2f:IR(KBr,cm
-1)2919,1661,1605,1572,1446,1410;
1HNMR(500MHz,CDCl
3,δ/ppm):7.86–7.88(m,4H),7.30–7.32(m,4H),2.45(s,6H);
13CNMR(125MHz,CDCl
3,δ/ppm):21.9,129.7,130.1,130.9,146.1,194.5.
2g:IR(KBr,cm
-1)2848,1656,1599,1573,1509,1459;
1HNMR(500MHz,CDCl
3,δ/ppm):7.96–7.97(m,4H),6.98–7.00(m,4H),3.90(s,6H);
13CNMR(125MHz,CDCl
3,δ/ppm):55.7,114.4,126.5,132.5,165.5,193.6.
2h:IR(KBr,cm
-1)2978,1659,1600,1575,1510,1478;
1HNMR(500MHz,CDCl
3,δ/ppm):7.93–7.95(m,4H),6.95–6.96(m,4H),4.12(q,4H,J=8Hz),1.45(t,6H,J=8Hz);
13CNMR(125MHz,CDCl
3,δ/ppm):14.6,64.0,114.7,126.1,132.4,164.3,193.6.
2i:IR(KBr,cm
-1)3047,2235,1676,1606,1561,1410;
1HNMR(500MHz,CDCl
3,δ/ppm):8.11–8.13(m,4H),7.85–7.87(m,4H);
13CNMR(125MHz,CDCl
3,δ/ppm):117.4,118.4,130.4,132.9,135.3,190.8.
2j:IR(KBr,cm
-1)3142,1646,1453,1392,1277,1025;
1HNMR(500MHz,CDCl
3,δ/ppm):7.65-7.79(m,4H),6.64-6.65(m,2H);
13CNMR(125MHz,CDCl
3,δ/ppm):113.2,124.8,149.5,176.9.
2k:IR(KBr,cm
-1)3100,1643,1496,1402,1345,1228;
1HNMR(500MHz,CDCl
3,δ/ppm):8.07–8.08(m,2H),7.84-7.85(m,2H),7.20-7.22(m,2H);
13CNMR(125MHz,CDCl
3,δ/ppm):128.8,137.4,137.6,138.7,182.5.
2l:IR(KBr,cm
-1)3051,1657,1574,1504,1360,1219;
1HNMR(500MHz,CDCl
3,δ/ppm):9.35-9.37(m,2H),8.13-8.14(m,2H),8.02-8.04(m,2H),7.96-7.97(m,2H),7.75-7.78(m,2H),7.63-7.66(m,2H),7.48-7.51(m,2H);
13CNMR(125MHz,CDCl
3,δ/ppm):124.6,126.1,127.2,128.9,129.5,131.2,134.2,135.0,135.2,136.0,197.1.
Example 2. is pressed example 1 method, carries out the oxidation of bitter almond oil camphor (1a) under different temperature of reaction, reacts 24h at 40 ℃, and the productive rate of benzil (2a) is 71%; At 80 ℃, react 20h, the productive rate of benzil (2a) is 87%; At 100 ℃, react 16h, the productive rate of benzil (2a) is 83%.
Example 3. adds the different silica GF254s of measuring after bitter almond oil camphor (1a) (0.42g, 2mmol) is dissolved completely in ethyl acetate (5mL) in solution.Mixture is stirred to completely and is mixed, vacuumize subsequently evaporation and obtain pulverulent solids except desolventizing.Gained powder is placed in to baking oven and contacts with air.Oven temperature is risen to 60 ℃, and by TLC monitoring reaction process.Mixture is intermittently jolted so that powder stirs up and down.Reaction mixture is through ethyl acetate washing, decompress filter except desolventizing, and resistates is through dehydrated alcohol recrystallization benzil (2a).Add 4g silica GF254, benzil productive rate 88%; Add 5g silica GF254, benzil productive rate 91%; Add 6g silica GF254, benzil productive rate 91%.
Example 4., according to example 1 method, is reused silica GF254 5 times, and benzil yield is respectively 91.1%, 90.0%, and 89.0%, 87.5%, 87.2%.
Claims (3)
1. utilize silica gel for carrier changes into bitter almond oil camphor atmospheric oxygen the method for benzil, it is characterized in that immobilized bitter almond oil camphor on silica GF254, the lower atmospheric oxidation of heating makes benzil, and its reaction expression is shown below:
2. method according to claim 1, is characterized in that suitable temperature of reaction is 40-100 ℃, preferably 60 ℃.
3. method according to claim 1, is characterized in that the mass ratio of suitable silica GF254 and reactant is greater than 10:1.
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CN104402696A (en) * | 2014-12-04 | 2015-03-11 | 安徽师范大学 | Oxidoreduction method of benzoin organic matter |
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CN103159607A (en) * | 2011-12-12 | 2013-06-19 | 中国科学院大连化学物理研究所 | Method for preparing benzil by oxidizing benzoin with molecular oxygen |
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WO2005113477A1 (en) * | 2004-05-20 | 2005-12-01 | Kuraray Co., Ltd. | PROCESS FOR PRODUCING α-OXOCARBONYL COMPOUND |
CN103159607A (en) * | 2011-12-12 | 2013-06-19 | 中国科学院大连化学物理研究所 | Method for preparing benzil by oxidizing benzoin with molecular oxygen |
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CN104402696A (en) * | 2014-12-04 | 2015-03-11 | 安徽师范大学 | Oxidoreduction method of benzoin organic matter |
CN104402696B (en) * | 2014-12-04 | 2016-02-03 | 安徽师范大学 | A kind of oxide-reduction method of bitter almond oil camphor type organic |
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