CN101671243B - Method for catalytically oxidizing organic matter by solid superacid and by taking potassium ferrate as oxidizing agent - Google Patents
Method for catalytically oxidizing organic matter by solid superacid and by taking potassium ferrate as oxidizing agent Download PDFInfo
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- CN101671243B CN101671243B CN200910179399.3A CN200910179399A CN101671243B CN 101671243 B CN101671243 B CN 101671243B CN 200910179399 A CN200910179399 A CN 200910179399A CN 101671243 B CN101671243 B CN 101671243B
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- potassium ferrate
- phenylcarbinol
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- UMPKMCDVBZFQOK-UHFFFAOYSA-N potassium;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[K+].[Fe+3] UMPKMCDVBZFQOK-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 239000007787 solid Substances 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 25
- 239000003930 superacid Substances 0.000 title claims abstract description 25
- 230000001590 oxidative effect Effects 0.000 title claims abstract description 14
- 239000007800 oxidant agent Substances 0.000 title claims abstract description 11
- 239000005416 organic matter Substances 0.000 title abstract 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 239000002904 solvent Substances 0.000 claims abstract description 22
- 230000035484 reaction time Effects 0.000 claims abstract description 19
- 238000003756 stirring Methods 0.000 claims abstract description 8
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 37
- 229960004217 benzyl alcohol Drugs 0.000 claims description 33
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 33
- 238000007254 oxidation reaction Methods 0.000 claims description 26
- 230000003647 oxidation Effects 0.000 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 18
- 150000002894 organic compounds Chemical class 0.000 claims description 16
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
- 238000007171 acid catalysis Methods 0.000 claims description 7
- 229910006404 SnO 2 Inorganic materials 0.000 claims description 5
- 239000011949 solid catalyst Substances 0.000 abstract description 12
- 239000007788 liquid Substances 0.000 abstract description 11
- 239000003377 acid catalyst Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 2
- 230000036632 reaction speed Effects 0.000 abstract 1
- -1 phenyl aldehyde Chemical class 0.000 description 14
- 239000002253 acid Substances 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- 230000009466 transformation Effects 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000010718 Oxidation Activity Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000001125 extrusion Methods 0.000 description 4
- 238000005470 impregnation Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000003252 repetitive effect Effects 0.000 description 4
- 238000005201 scrubbing Methods 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for catalytically oxidizing organic matter by solid superacid and by taking potassium ferrate as an oxidizing agent. The method comprises the following steps: placing the solid catalyst into a flat bottom beaker, adding organic matter to be oxidized, then adding solvent, adding the potassium ferrate under stirring, and controlling the reaction temperature to 20-70 DEG C and the reaction time to 2-12 hours to obtain the products. The invention provides a method for catalytically oxidizing organic matter by the solid superacid and by taking the potassium ferrate as the oxidizing agent; the adding of solid superacid greatly improves the reaction speed of potassium ferrate for oxidizing organic matter and shortens the reaction time; and the method does not use any liquid acid catalyst, and is characterized by simple operation, economy, green initiative and the like and can be widely applied to the synthetic field of organic chemicals.
Description
Technical field:
The present invention relates to a kind of take the method for potassium ferrate as oxidant with solid super acid catalysis oxidation of organic compounds, specifically in the organism system, under the solid super acid catalyst effect, with the novel method of potassium ferrate oxidation of organic compounds.
Background technology:
The present invention relates to a kind of take the method for potassium ferrate as oxidant with solid super acid catalysis oxidation of organic compounds, specifically in the organism system, under the solid super acid catalyst effect, with the novel method of potassium ferrate oxidation of organic compounds.
The general valence state of iron is II and III valency, and the valence state of high price iron-based composite is the IV-VI valency.Principal feature is high oxidisability, is a kind of KMnO of ratio
3, O
2And Cl
2Oxidation capacity strong strong oxidizer also, can the most of organism of oxidation.The Fe-base compound of simple VI, electron transfer number be up to 3, and can regulate its positively charged ion, structure, pH value, regulates and control oxidation activity.Fe is different from Cr and Mn, is nontoxic, because its by product iron rust can not have any detrimentally affect to human and environment.Therefore, ferrate can be done oxygenant, sanitising agent, water conditioner, battery electrode, shows its unique advantage and potentiality.Adutte in 1971 etc. have carried out potassium ferrate first for the synthetic research of oxidation operation, so far are used for the oxidation operation synthetic method about potassium ferrate, mainly comprise in synthetic in the alkaline aqueous solution and the organic solvent and synthesize two kinds.Alkaline aqueous solution is as its weak point of oxidizing reaction that solvent carries out, and speed of response is exceedingly fast, and selectivity is easy-regulating not, is unsuitable for the oxidation compound responsive to alkalescence, and particularly to being insoluble in the organism of water, oxidizing reaction is difficult to carry out more.During as solvent, because potassium ferrate is insoluble to organism, its activity is not in full use with organism, and long reaction time, productive rate are very low.1996, Lionel has proposed a kind of in organic solvent, take montmorillonite as solid catalyst, potassium ferrate is made the oxidation synthesis method of oxygenant, at room temperature realized first organic selective oxidation, although the method can improve the synthetic ultimate yield of oxidation, the method has long reaction time simultaneously, the shortcomings such as potassium ferrate and organism solvent load height.We had proposed a kind of novel method (people such as Song Hua who improves oxidation activity of potassium ferrate in 2007, Chinese patent ZL200510053372.1), the method is by add a small amount of aqueous acid in organic solvent, improve the oxidation activity of potassium ferrate, and then reached the greatly purpose of Reaction time shorten, but the shortcoming of the method is to have added liquid acid.
Summary of the invention:
The objective of the invention is in order to overcome the deficiencies in the prior art, provide under a kind of condition adding any liquid acid catalyst, in organic phase, with the novel method of potassium ferrate oxidation of organic compounds, the method is not used any liquid acid catalyst, is a kind of oxidation technology of environmental protection.
The technical solution adopted in the present invention content is: comprise the following steps take the method for potassium ferrate as oxidant with solid super acid catalysis oxidation of organic compounds, solid catalyst is put into flat bottom beaker, add oxidized organism, then add solvent, stir the lower potassium ferrate that adds, 20～70 ℃ of control temperature of reaction, reaction times 2～12h namely gets product.
The mass volume ratio (g/ml) of above-mentioned solid catalyst add-on and phenylcarbinol is 1: 1～5: 1, and the volume ratio of solvent and phenylcarbinol is 25: 1～150: 1, and the mass volume ratio of potassium ferrate and phenylcarbinol (g/ml) is 2.5: 1～7.5: 1; The mass volume ratio of solid catalyst add-on and phenylcarbinol (g/ml) is 2.5: 1, and the volume ratio of solvent and phenylcarbinol is 100: 1, and the mass volume ratio of potassium ferrate and phenylcarbinol (g/ml) is 4: 1; Solvent is hexanaphthene;
30～40 ℃ of control temperature of reaction, reaction times 2h.
The invention has the beneficial effects as follows: it is a kind of take potassium ferrate as oxygenant that the present invention proposes, the method of solid superacid as catalyst oxidation of organic compounds, owing to having added solid super-strong acid, its huge specific surface area provides larger contact area for the potassium ferrate oxidation reactant, under agitation potassium ferrate can with organic phase in reactant fully contact, overcome when in pure organic phase, reacting, potassium ferrate is insoluble to organic solvent, the deficiency that speed of response is very low has improved the speed of oxidizing reaction; When the potassium ferrate oxidation of organic compounds, add acid than dense H
2SO
4Stronger, and to the free from corrosion solid super-strong acid of equipment, because potassium ferrate in acid atmosphere has great oxidation activity, thereby improved the oxidation activity of oxygenant.It is a kind of take potassium ferrate as oxygenant that the present invention proposes, and the method for solid superacid as catalyst oxidation of organic compounds owing to having added solid super-strong acid, has improved the speed of response of the oxidation of organic compounds of potassium ferrate greatly, has shortened the reaction times.Present method is not used any liquid acid catalyst, has simultaneously the characteristics such as simple to operate, economy, environmental protection, can be widely used in the synthetic field of organic chemicals.
Description of drawings:
The change curve that affects on reaction of Fig. 1 solvent load;
The change curve that affects on reaction of Fig. 2 temperature;
The change curve that affects on reaction of Fig. 3 oxygenant consumption;
The change curve that affects on reaction of Fig. 4 solvent load;
The change curve that affects on reaction in Fig. 5 reaction times.
Embodiment:
The invention will be further described below in conjunction with embodiment:
Embodiment 1: add solid catalyst SO in the 50mL volumetric flask
4 2-/ Al
2O
3-ZrO
20.5g, phenylcarbinol 0.2mL, potassium ferrate 0.8g, 30 ℃ of temperature of reaction, reaction times 2h changes the cyclohexane solvent consumption, investigates the impact of solvent load.Filtering reacting liquid carries out stratographic analysis with filtrate, result such as table 1 and shown in Figure 1.
Table 1
Conclusion: can be found out by table 1 data, reduce along with the increase phenylcarbinol transformation efficiency of solvent load and phenyl aldehyde productive rate increase afterwards first, when solvent load was 20mL, phenylcarbinol transformation efficiency and phenyl aldehyde productive rate were the highest.
Embodiment 2: add solid catalyst SO in the 50mL volumetric flask
4 2-/ Al
2O
3-ZrO
20.5g, phenylcarbinol 0.2mL, solvent hexanaphthene 20mL, potassium ferrate 0.8g, reaction times 2h changes temperature of reaction, investigates the impact of temperature.Filtering reacting liquid carries out stratographic analysis with filtrate, result such as table 2 and shown in Figure 2.
Table 2
Conclusion: can be found out by table 2 data, in given temperature range, along with increase phenylcarbinol transformation efficiency and the variation of phenyl aldehyde productive rate of temperature of reaction are little, the Changing Pattern of phenyl aldehyde productive rate is to increase afterwards first to reduce, and when temperature was 40 ℃, the phenyl aldehyde productive rate was the highest.
Embodiment 3: add solid catalyst SO in the 50mL volumetric flask
4 2-/ Al
2O
3-ZrO
20.5g, phenylcarbinol 0.2mL, solvent hexanaphthene 20mL, 40 ℃ of temperature of reaction, reaction times 2h changes the potassium ferrate consumption, investigates the impact of oxygenant consumption.Filtering reacting liquid carries out stratographic analysis with filtrate, result such as table 3 and shown in Figure 3.
Table 3
Conclusion: can be found out by table 3 data, take the lead in improving comparatively fast along with the increase phenylcarbinol of potassium ferrate consumption transforms, after the potassium ferrate consumption is 0.7, along with the increase phenylcarbinol transformation efficiency of potassium ferrate consumption improves slowly.Reduce along with the increase phenyl aldehyde productive rate of potassium ferrate consumption increases afterwards first, when solvent load was 0.8g, the phenyl aldehyde productive rate was the highest.
Embodiment 4: in the 50mL volumetric flask, add phenylcarbinol 0.2mL, and solvent hexanaphthene 20mL, potassium ferrate 0.8g, 40 ℃ of temperature of reaction, reaction times 2h changes solid catalyst SO
4 2-/ Al
2O
3-ZrO
2Consumption is investigated the impact of catalyst levels.Filtering reacting liquid carries out stratographic analysis with filtrate, result such as table 4 and shown in Figure 4.
Table 4
Conclusion: can be found out by table 4 data, along with increase phenylcarbinol transformation efficiency and the benzyl alcohol selective of catalyst levels improves first comparatively fast, after catalyst levels is 0.5, along with increase phenylcarbinol transformation efficiency and the raising of phenyl aldehyde productive rate of catalyst levels are not obvious.
Embodiment 5: add solid catalyst SO in the 50mL volumetric flask
4 2-/ Al
2O
3-ZrO
20.5g, phenylcarbinol 0.2mL, solvent hexanaphthene 20mL, potassium ferrate 0.8g, 40 ℃ of temperature of reaction change the reaction times, investigate the impact of catalyst levels.Filtering reacting liquid carries out stratographic analysis with filtrate, result such as table 5 and shown in Figure 5.
Table 5
Conclusion: can be found out by table 5 data, along with increase phenylcarbinol transformation efficiency and the benzyl alcohol selective in reaction times improves first comparatively fast, after the reaction times is 8h, along with increase phenylcarbinol transformation efficiency and the phenyl aldehyde productive rate in reaction times improves not obvious.
Step 1, the phenylcarbinol that measures 0.2mL are put into flat bottom beaker, add the SO of 0.5g
4 2-/ SnO
2Solid super acid catalyst, S
2O
8 2-/ Al
2O
3-ZrO
2Solid super acid catalyst, SO
4 2-/ SnO
2-Al
2O
3Solid super acid catalyst or SO
4 2-/ Al
2O
3-ZrO
2Solid super acid catalyst.
Step 3, filtering reacting liquid carry out stratographic analysis with filtrate, and what obtain the results are shown in Table 6.As can be seen from Table 6, reaction equal phenyl aldehyde productive rate greater than without solid catalyst time of phenyl aldehyde productive rate during 2h under the various super acids effects shows the reaction of the catalysis potassium ferrate oxidation of organic compounds that solid super-strong acid all can be in various degree.
Table 6
Conclusion: as can be seen from Table 6, reaction equal phenyl aldehyde productive rate greater than without solid catalyst time of phenyl aldehyde productive rate during 2h under the various super acids effects shows the reaction of the catalysis potassium ferrate oxidation of organic compounds that solid super-strong acid all can be in various degree, wherein SO
4 2-/ Al
2O
3-ZrO
2Catalytic effect best, the phenyl aldehyde productive rate is 44.1% during 2h, has improved 29.9% when not having catalyzer, catalytic effect is obvious.
Method for preparing catalyst used in above-described embodiment is as follows:
(1) SO
4 2-/ ZrO
2-Al
2O
3The preparation method of catalyzer:
Take by weighing ZrOCl
28H
2O and Al (NO
3)
39H
2O is dissolved in distilled water, ZrOCl
28H
2O and Al (NO
3)
39H
2The O mass ratio is 6.753: 1, is that 20% ammonia water titration is to pH=10 with mass concentration under vigorous stirring.Precipitation ageing 24h, repetitive scrubbing is extremely without Cl
-, 110 ℃ lower dry, is ground to more than 120 orders, obtains ZrO
2-Al
2O
3The catalyzer precursor.Be (the NH of 0.5mol/L with this precursor powder concentration
4)
2S
2O
8Solution impregnation 6h, extrusion, 600 ℃ of lower roasting 3h prepare S behind the oven dry 4h
2O
8 2-/ ZrO
2-Al
2O
3Catalyzer.
(2) SO
4 2-/ SnO
2-Al
2O
3The preparation method of catalyzer:
Take by weighing SnCl
45H
2O and Al (NO
3)
39H
2O is dissolved in distilled water, SnCl
45H
2O and Al (NO
3)
39H
2The mass ratio of O is 6.007: 1, is that 20% ammonia water titration is to pH=10 with mass concentration under vigorous stirring.Precipitation ageing 24h, repetitive scrubbing is extremely without Cl
-, 110 ℃ lower dry, is ground to more than 120 orders, obtains SnO
2-Al
2O
3The catalyzer precursor.Be the H of 0.5mol/L with this precursor powder concentration
2SO
4Solution impregnation 6h, extrusion, 600 ℃ of lower roasting 3h prepare SO behind the oven dry 4h
4 2-/ SnO
2-Al
2O
3Catalyzer.
(3) SO
4 2-/ SnO
2The preparation method of catalyzer:
Take by weighing an amount of SnCl
45H
2After O is dissolved in distilled water, under vigorous stirring, be that 20% ammonia water titration is to pH=10 with mass concentration.Precipitation ageing 24h, repetitive scrubbing is extremely without Cl
-, 110 ℃ lower dry, is ground to more than 120 orders, obtains SnO
2The catalyzer precursor.Be the H of 0.5mol/L with this precursor powder concentration
2SO
4Solution impregnation 6h, extrusion, 600 ℃ of lower roasting 3h prepare SO behind the oven dry 4h
4 2-/ SnO
2Catalyzer.
(4) S
2O
8 2-/ Al
2O
3-ZrO
2The preparation method of catalyzer:
Take by weighing ZrOCl
28H
2O and Al (NO
3)
39H
2After O is dissolved in distilled water, ZrOCl
28H
2O and Al (NO
3)
39H
2The mass ratio of O is 13.861: 1, is that 20% ammonia water titration is to pH=10 with mass concentration under vigorous stirring.Precipitation ageing 24h, repetitive scrubbing is extremely without Cl
-, 110 ℃ lower dry, is ground to more than 120 orders, obtains ZrO
2-Al
2O
3The catalyzer precursor.Be the H of 0.5mol/L with this precursor powder concentration
2SO
4Solution impregnation 6h, extrusion, 600 ℃ of lower roasting 3h prepare S behind the oven dry 4h
2O
8 2-/ ZrO
2-Al
2O
3Catalyzer.
Claims (3)
1. one kind take the method for potassium ferrate as oxidant with solid super acid catalysis oxidation of organic compounds phenylcarbinol, it is characterized in that: comprise the following steps, solid super acid catalyst is put into flat bottom beaker, add oxidized phenylcarbinol, then add solvent, stir the lower potassium ferrate that adds, 20～70 ℃ of control temperature of reaction, reaction times 2～12h namely gets product, and wherein solid super acid catalyst is SO
4 2-/ ZrO
2-Al
2O
3, SO
4 2-/ SnO
2-Al
2O
3, SO
4 2-/ SnO
2And S
2O
8 2-/ Al
2O
3-ZrO
2In a kind of.
2. according to claim 1 take the method for potassium ferrate as oxidant with solid super acid catalysis oxidation of organic compounds phenylcarbinol, it is characterized in that: the mass volume ratio of solid super acid catalyst add-on and phenylcarbinol (g/ml) is 1: 1～5: 1, the volume ratio of solvent and phenylcarbinol is 25: 1～150: 1, the mass volume ratio of potassium ferrate and phenylcarbinol (g/ml) is 2.5: 1～7.5: 1,30～40 ℃ of control temperature of reaction, reaction times 2h.
3. according to claim 2 take the method for potassium ferrate as oxidant with solid super acid catalysis oxidation of organic compounds phenylcarbinol, it is characterized in that: the mass volume ratio of solid super acid catalyst add-on and phenylcarbinol (g/ml) is 2.5: 1, the volume ratio of solvent hexanaphthene and phenylcarbinol is 100: 1, and the mass volume ratio of potassium ferrate and phenylcarbinol (g/ml) is 4: 1.
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| Title |
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| 张娇静等.固体催化剂存在下高铁酸钾氧化合成苯甲醛.《化学工程》.2008,第36卷(第9期),全文. * |
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