CN104326870A - Hydrogenolysis method of cyclohexyl hydroperoxide - Google Patents
Hydrogenolysis method of cyclohexyl hydroperoxide Download PDFInfo
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
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- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
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Abstract
The invention discloses a hydrogenolysis method of cyclohexyl hydroperoxide and belongs to the technical field of organic chemistry. The method comprises the following specific steps: washing a cyclohexane oxidation solution containing cyclohexyl hydroperoxide, isolating an organic phase, adding a Pd/Al catalyst into the organic phase, introducing hydrogen, reacting at the temperature of 50-120 DEG C and at the pressure of 0.1-1.5 MPa for 0.1-3h, filtering the catalyst, carrying out alkali cleaning by adding 5-30 wt% of alkali lye into the reaction liquid with introduced hydrogen, washing with water after alkali cleaning, carrying out liquid separation after water washing, and collecting the organic phase, wherein mass ratio of the catalyst to the organic phase is 1:10-10000 and diameter of the catalyst is 0.01-10mm. The Pd/Al catalyst is used to catalyze hydrogenolysis of cyclohexyl hydroperoxide; reaction condition is mild; selectivity is high; treatment after the reaction is convenient; dosage of the catalyst is low and the catalyst can be recycled; and conversion rate and selectivity are high.
Description
Technical field
The present invention relates to technical field of organic chemistry, particularly a kind of hydrogenation decomposition method of cyclohexyl hydroperoxide.
Background technology
KA oil major part used in current hexanodioic acid Industrial processes is prepared without catalytic air oxidation by hexanaphthene, cyclohexane oxidation is prepared KA oil and is comprised following step: 1) hexanaphthene is at 160 ~ 180 DEG C, obtain through air non-catalyst oxidation the cyclohexane oxide solution that primary product is cyclohexyl hydroperoxide, and containing have an appointment 0.5 ~ 0.8% acids and Ester; 2) cyclohexyl hydroperoxide in cyclohexane oxide solution is decomposed into pimelinketone and hexalin under certain basicity; 3) rectifying obtains mixture and the KA oil of pimelinketone and hexalin.In current decomposing cyclohexyl hydrogen peroxide process, there are the following problems: production energy consumption is higher, and the selectivity of decomposing cyclohexyl hydrogen peroxide is low, and pimelinketone polycondensation is obvious, and add a large amount of alkali in producing, and generates a large amount of alkaline waste water and contaminate environment.
The patent of invention that publication number is " CN1184097A " discloses under temperature 120 ~ 130 DEG C of conditions, substep or add the aqueous solution of the catalyzer such as the Cobaltous diacetate of 500 ~ 2000ppm and/or Jing Ti/Bao Pian COBALT NITRATE CRYSTALS/FLAKES, rose vitriol, chromium acetate, chromic trioxide continuously in decomposition reactor, the shortcoming of this technique is that temperature of reaction is higher, catalyst concn is bigger than normal, and product yield is 85 ~ 88%.
Disclose a kind of method that cyclohexyl hydroperoxide shortening decomposes in US Patent No. 4720592, be pimelinketone and hexalin by cyclohexylhydroperoxconversion conversion in fixed-bed reactor, reaction pressure is 0.9 ~ 1.2Mpa, and temperature of reaction is 130 ~ 150 DEG C.The reaction conditions of the method requires higher, also higher to the requirement of equipment; The cyclohexane oxidation by product prepared in cyclohexyl hydroperoxide process is easy in hydrogenation catalyst surface attachment, causes the activity of catalyzer to reduce; The total recovery of alcohol ketone is not 92% also high.
Summary of the invention
In order to make up the deficiencies in the prior art, the invention provides that a kind of reaction conditions is gentle, the hydrogenation decomposition method of high, the convenient post-treatment of keto-alcohol selectivity in degradation production, cyclohexyl hydroperoxide that catalyzer usage quantity is few.
The technical solution used in the present invention is:
A kind of hydrogenation decomposition method of cyclohexyl hydroperoxide, the cyclohexane oxide solution of washing containing cyclohexyl hydroperoxide, then isolates organic phase, adds Pd/Al catalyzer in organic phase, pass into hydrogen, temperature 50-120 DEG C, under pressure 0.1-1.5MPa condition, reaction 0.1-3h, elimination catalyzer, and to add massfraction in the reaction solution after hydrogenation be that the alkali lye of 5-30% carries out alkali cleaning, wash again after alkali cleaning, separatory after washing, collect organic phase; Wherein, the mass ratio of catalyzer and organic phase is 1:10-10000, and the diameter of catalyzer is 0.01-10mm.Wash after alkali cleaning, separatory after washing, collect organic phase, collected organic phase is the mixed solution of hexanaphthene, pimelinketone and hexalin again.Washing is the acid in order to remove in cyclohexane oxide solution before hydrogenation reaction, and this step on the one hand can the useful organic acid of recovery part, and when decreasing follow-up alkali cleaning, alkali lye consumption, reduces the discharge of waste lye simultaneously; On the other hand, promote that the forward adding hydroperoxide decomposition reaction carries out, improve productive rate.
Preferably, described Pd/Al Palladium Content in Catalyst is 0.2-20%.
Further, the mass ratio of described Pd/Al catalyzer and organic phase is 1:50-200.
Preferably, before hydrogenation during washing, washing temperature is 60-90 DEG C, and the volume ratio of water and described cyclohexane oxide solution is 1:5-100.
Preferably, under temperature 70 ~ 100 DEG C, pressure 0.1 ~ 0.5Mpa condition, reaction 0.2 ~ 2h.
Preferably, after hydrogenation reaction, catalyst filtration is separated, can be recycled after the catalyzer drying after separation.
Preferably, after hydrogenation reaction, alkali cleaning temperature is 60-100 DEG C, and the volume ratio of alkali lye and reaction solution is 1:5-100.The object of alkali cleaning is acid in removing reaction solution and ester, makes in reaction solution only containing hexanaphthene, pimelinketone and hexalin.
Preferably, after hydrogenation reaction, the temperature of washing is 60-100 DEG C, and the volume ratio of water and reaction solution is 1:5-100.
As preferably, water used is distilled water or de-salted water.
Beneficial effect of the present invention is:
The present invention adopts the hydrogenation of cyclohexyl hydroperoxide in palladium Al catalysts catalysis cyclohexane oxidation liquid to decompose, reaction conditions is gentle, and selectivity is high, and post-reaction treatment is convenient, catalyst levels is few, and substantially increases the transformation efficiency of cyclohexyl hydroperoxide and the yield of pimelinketone and hexalin.Decomposing cyclohexyl hydrogen peroxide transformation efficiency >=90%, pimelinketone and hexalin yield >=90%.The organic acid that before hydrogenation, the recyclable part of washing is useful, and alkali number used during alkali cleaning after decreasing hydrogenation, decrease waste lye quantity discharged; Catalyzer can be recycled, and reduces catalyst consumption, reduces cost.
Embodiment
Embodiment 1
Under normal pressure, be in 1000ml there-necked flask at volume, add hexanaphthene non-catalyst oxidation liquid and 70ml de-salted water that 700ml contains cyclohexyl hydroperoxide, stir washing, washing temperature is 75 DEG C, and washing time is 0.25h, after washing, by organic phase and inorganic phase Liquid liquid Separation.Water intaking wash after the organic phase 500g that separates, to add palladium content be 1% particle diameter is the Pd/Al catalyzer 5g of 100um, passes into hydrogen, under temperature 95 DEG C, pressure 0.5Mpa condition, reaction 0.5h, hydrogenation decomposing cyclohexylhdroperoxide; Add the aqueous sodium hydroxide solution that massfraction is 10% in reaction solution after hydrogenation, stir alkali cleaning, alkali cleaning temperature is 70 DEG C, and the volume ratio of alkali lye and reaction solution is 1:30; Reaction solution after alkali cleaning adds de-salted water again, and stir washing, washing temperature is 70 DEG C, and the ratio of water and reaction solution is 1:100.The organic phase obtained after washing separatory is the mixed solution of hexanaphthene, pimelinketone and hexalin.
Containing pimelinketone 0.77%, hexalin 0.98%, cyclohexyl hydroperoxide 4.05% in hexanaphthene non-catalyst oxidation liquid containing cyclohexyl hydroperoxide, acid 0.40%, ester 0.35%; After washing, containing pimelinketone 0.86%, hexalin 0.98%, cyclohexyl hydroperoxide 3.63% in organic phase, acid 0.24%, ester 0.34%; Pimelinketone 1.01%, hexalin 4.05%, cyclohexyl hydroperoxide 0.06% is contained in reaction solution, acid 0.25%, ester 0.17% after hydrogenation; Containing pimelinketone 1.0%, hexalin 4.05%, cyclohexyl hydroperoxide 0.0054% after alkali cleaning washing, sour nothing, ester without; The transformation efficiency of hydrogenation reaction cyclohexyl hydroperoxide is 98.3%, and the selectivity of pimelinketone and hexalin is 100%.
Embodiment 2
Under normal pressure, be in 1000ml there-necked flask at volume, add hexanaphthene non-catalyst oxidation liquid and 20ml de-salted water that 700ml contains cyclohexyl hydroperoxide, stir washing, washing temperature is 80 DEG C, and washing time is 1h, after washing, by organic phase and inorganic phase Liquid liquid Separation.Water intaking wash after the organic phase 500g that separates, to add palladium content be 1% particle diameter is the Pd/Al catalyzer 2.5g of 500um, passes into hydrogen, under temperature 90 DEG C, pressure 0.45Mpa condition, reaction 0.5h, hydrogenation decomposing cyclohexylhdroperoxide; Reaction solution after hydrogenation adds the aqueous sodium hydroxide solution that massfraction is 15%, and stir alkali cleaning, alkali cleaning temperature is 65 DEG C, and the volume ratio of alkali lye and reaction solution is 1:20; Reaction solution after alkali cleaning adds de-salted water again, and stir washing, washing temperature is 65 DEG C, and the ratio of de-salted water and reaction solution is 1:20.The organic phase obtained after washing separatory is the mixed solution of hexanaphthene, pimelinketone and hexalin.
Containing pimelinketone 0.76%, hexalin 0.97%, cyclohexyl hydroperoxide 4.1 % in hexanaphthene non-catalyst oxidation liquid containing cyclohexyl hydroperoxide, acid 0.45%, ester 0.35%; After washing, containing pimelinketone 0.58%, hexalin 0.8%, cyclohexyl hydroperoxide 3.87% in organic phase, acid 0.2%, ester 0.37%; Pimelinketone 1.08%, hexalin 4.1%, cyclohexyl hydroperoxide 0.05% is contained in reaction solution, acid 0.25%, ester 0.20% after hydrogenation; Containing pimelinketone 1.05 %, hexalin 4.08%, cyclohexyl hydroperoxide 0.006% after alkali cleaning washing, sour nothing, ester without.The transformation efficiency of hydrogenation reaction cyclohexyl hydroperoxide is 98.7%, the transformation efficiency 100% of pimelinketone and hexalin.
Embodiment 3
Under normal pressure, be in 1000ml there-necked flask at volume, add hexanaphthene non-catalyst oxidation liquid and 50ml de-salted water that 700ml contains cyclohexyl hydroperoxide, stir washing, washing temperature is 65 DEG C, and washing time is 0.5h, after washing, by organic phase and inorganic phase Liquid liquid Separation.Water intaking wash after the organic phase 500g that separates, to add palladium content be 5% particle diameter is the Pd/Al catalyzer 2g of 5-6mm, passes into hydrogen, under temperature 100 DEG C, pressure 0.6Mpa condition, reaction 0.3h, hydrogenation decomposing cyclohexylhdroperoxide; Reaction solution after hydrogenation adds the aqueous sodium hydroxide solution that massfraction is 25%, and stir alkali cleaning, alkali cleaning temperature is 65 DEG C, and the volume ratio of alkali lye and reaction solution is 1:35; Reaction solution after alkali cleaning adds de-salted water again, and stir washing, washing temperature is 60 DEG C, and the ratio of de-salted water and reaction solution is 1:50.The organic phase obtained after washing separatory is the mixed solution of hexanaphthene, pimelinketone and hexalin.
Containing pimelinketone 0.72%, hexalin 0.89%, cyclohexyl hydroperoxide 4.07 % in hexanaphthene non-catalyst oxidation liquid containing cyclohexyl hydroperoxide, acid 0.45%, ester 0.4%; After washing, containing pimelinketone 0.6%, hexalin 0.8%, cyclohexyl hydroperoxide 3.9% in organic phase, acid 0.25%, ester 0.37%; Pimelinketone 1.1%, hexalin 3.93%, cyclohexyl hydroperoxide 0.05% is contained in reaction solution, acid 0.25%, ester 0.20% after hydrogenation; Containing pimelinketone 1.06%, hexalin 3.9%, cyclohexyl hydroperoxide 0.04% after alkali cleaning washing, sour nothing, ester without.The transformation efficiency of hydrogenation reaction cyclohexyl hydroperoxide is 96.4%, the transformation efficiency 100% of pimelinketone and hexalin.
Embodiment 4
Under normal pressure, be in 1000ml there-necked flask at volume, add hexanaphthene non-catalyst oxidation liquid and 35ml de-salted water that 700ml contains cyclohexyl hydroperoxide, stir washing, washing temperature is 80 DEG C, and washing time is 0.5h, after washing, by organic phase and inorganic phase Liquid liquid Separation.Water intaking wash after the organic phase 500g that separates, to add palladium content be 0.8% particle diameter is the Pd/Al catalyzer 5g of 2mm, passes into hydrogen, under temperature 95 DEG C, pressure 0.6Mpa condition, reaction 0.3h, hydrogenation decomposing cyclohexylhdroperoxide; Reaction solution after hydrogenation adds the aqueous sodium hydroxide solution that massfraction is 5 ~ 15%, and stir alkali cleaning, alkali cleaning temperature is 80 DEG C, and the volume ratio of alkali lye and reaction solution is 1:50; Reaction solution after alkali cleaning adds de-salted water again, and stir washing, washing temperature is 70 DEG C, and the ratio of de-salted water and reaction solution is 1:60.The organic phase obtained after washing separatory is the mixed solution of hexanaphthene, pimelinketone and hexalin.
Containing pimelinketone 0.69%, hexalin 0.85%, cyclohexyl hydroperoxide 4.2 % in hexanaphthene non-catalyst oxidation liquid containing cyclohexyl hydroperoxide, acid 0.38%, ester 0.41%; After washing, containing pimelinketone 0.6%, hexalin 0.8%, cyclohexyl hydroperoxide 3.95% in organic phase, acid 0.2%, ester 0.37%; Pimelinketone 0.91%, hexalin 4.06%, cyclohexyl hydroperoxide 0.05% is contained in reaction solution, acid 0.22%, ester 0.20% after hydrogenation; Containing pimelinketone 0.89%, hexalin 4.05%, cyclohexyl hydroperoxide 0.07 % after alkali cleaning washing, sour nothing, ester without.The transformation efficiency of hydrogenation reaction cyclohexyl hydroperoxide is 98.2%, the transformation efficiency 100% of pimelinketone and hexalin.
Embodiment 5
Under normal pressure, be in 1000ml there-necked flask at volume, add hexanaphthene non-catalyst oxidation liquid and 50ml de-salted water that 700ml contains cyclohexyl hydroperoxide, stir washing, washing temperature is 75 DEG C, and washing time is 0.5h, after washing, by organic phase and inorganic phase Liquid liquid Separation.Water intaking wash after the organic phase 500g that separates, to add palladium content be 0.5% particle diameter is the Pd/Al catalyzer 10g of 2-3mm, passes into hydrogen, under temperature 105 DEG C, pressure 0.3Mpa condition, reaction 0.6h, hydrogenation decomposing cyclohexylhdroperoxide; Reaction solution after hydrogenation adds the aqueous sodium hydroxide solution that massfraction is 20%, and stir alkali cleaning, alkali cleaning temperature is 100 DEG C, and the volume ratio of alkali lye and reaction solution is 1:35; Reaction solution after alkali cleaning adds de-salted water again, and stir washing, washing temperature is 90 DEG C, and the ratio of de-salted water and reaction solution is 1:30.The organic phase obtained after washing separatory is the mixed solution of hexanaphthene, pimelinketone and hexalin.
Containing pimelinketone 0.78%, hexalin 0.9%, cyclohexyl hydroperoxide 4.07 % in hexanaphthene non-catalyst oxidation liquid containing cyclohexyl hydroperoxide, acid 0.40%, ester 0.39%; After washing, containing pimelinketone 0.6%, hexalin 0.8%, cyclohexyl hydroperoxide 3.91% in organic phase, acid 0.19%, ester 0.37%; Pimelinketone 1.01%, hexalin 3.98%, cyclohexyl hydroperoxide 0.02% is contained in reaction solution, acid 0.2%, ester 0.20% after hydrogenation; Containing pimelinketone 1.0.1%, hexalin 3.96%, cyclohexyl hydroperoxide 0.04% after alkali cleaning washing, sour nothing, ester without.The transformation efficiency of hydrogenation reaction cyclohexyl hydroperoxide is 99%, the transformation efficiency 100% of pimelinketone and hexalin.
Catalyst recirculation uses
Under normal pressure, be in the container of 5000ml at volume, add hexanaphthene non-catalyst oxidation liquid and 229ml de-salted water that 4000ml contains cyclohexyl hydroperoxide, stir washing, washing temperature is 70 DEG C, and washing time is 0.5h, after washing, by organic phase and inorganic phase Liquid liquid Separation, obtain oil phase 2857g.After washing oil phase, containing pimelinketone 0.75%, hexalin 0.88%, cyclohexyl hydroperoxide 3.8% in organic phase, acid 0.19%, ester 0.37%.
A catalyzer reuse
Get the oil phase 500g after above-mentioned washing, add isolated catalyzer 9.9g in example 5, repeat above step, containing pimelinketone 1.1%, hexalin 4.15%, cyclohexyl hydroperoxide 0.01% after the alkali cleaning that finally obtains washing, sour nothing, ester without.The transformation efficiency of hydrogenation reaction cyclohexyl hydroperoxide is 99.7%, the selectivity 100% of pimelinketone and hexalin.
Catalyzer secondary returning is used
Get the oil phase 500g after above-mentioned washing, add the isolated catalyzer 9.9g of a reuse, repeat above step, containing pimelinketone 1.05%, hexalin 4.05%, cyclohexyl hydroperoxide 0.02% after the alkali cleaning that finally obtains washing, sour nothing, ester without.The transformation efficiency of hydrogenation reaction cyclohexyl hydroperoxide is 99.5 %, the transformation efficiency 99.5% of pimelinketone and hexalin.
Catalyzer three reuses
Get the oil phase 500g after above-mentioned washing, add the isolated catalyzer 9.9g of secondary returning, repeat above step, containing pimelinketone 1.05%, hexalin 4.11%, cyclohexyl hydroperoxide 0.00% after the alkali cleaning that finally obtains washing, sour nothing, ester without.The transformation efficiency of hydrogenation reaction cyclohexyl hydroperoxide is 100 %, the selectivity 99% of pimelinketone and hexalin.
Catalyzer four reuses
Get the oil phase 500g after above-mentioned washing, add the isolated catalyzer 9.89g of three reuses, repeat above step, containing pimelinketone 0.98%, hexalin 4.4.06%, cyclohexyl hydroperoxide 0.02% after the alkali cleaning that finally obtains washing, sour nothing, ester without.The transformation efficiency of hydrogenation reaction cyclohexyl hydroperoxide is 99.5 %, the selectivity 99.6% of pimelinketone and hexalin.
Catalyzer five reuses
Get the oil phase 500g after above-mentioned washing, add the isolated catalyzer 9.89g of four reuses, repeat above step, containing pimelinketone 1.01%, hexalin 4.05%, cyclohexyl hydroperoxide 0.025% after the alkali cleaning that finally obtains washing, sour nothing, ester without.The transformation efficiency of hydrogenation reaction cyclohexyl hydroperoxide is 99.3 %, the selectivity 99.5% of pimelinketone and hexalin.
Claims (9)
1. the hydrogenation decomposition method of a cyclohexyl hydroperoxide, it is characterized in that: the cyclohexane oxide solution of washing containing cyclohexyl hydroperoxide, then isolate organic phase, in organic phase, add Pd/Al catalyzer, pass into hydrogen, temperature 50-120 DEG C, under pressure 0.1-1.5MPa condition, reaction 0.1-3h, elimination catalyzer, and to add massfraction in the reaction solution after hydrogenation be that the alkali lye of 5-30% carries out alkali cleaning, wash again after alkali cleaning, separatory after washing, collect organic phase; Wherein, the mass ratio of catalyzer and organic phase is 1:10-10000, and the diameter of catalyzer is 0.01-10mm.
2. the hydrogenation decomposition method of cyclohexyl hydroperoxide as claimed in claim 1, is characterized in that: described Pd/Al Palladium Content in Catalyst is 0.2-20%.
3. the hydrogenation decomposition method of cyclohexyl hydroperoxide as claimed in claim 2, is characterized in that: the mass ratio of described Pd/Al catalyzer and organic phase is 1:50-200.
4. the hydrogenation decomposition method of cyclohexyl hydroperoxide as claimed in claim 1, is characterized in that: before hydrogenation during washing, washing temperature is 60-90 DEG C, and the volume ratio of water and described cyclohexane oxide solution is 1:5-100.
5. the hydrogenation decomposition method of cyclohexyl hydroperoxide as claimed in claim 1, is characterized in that: under temperature 70 ~ 100 DEG C, pressure 0.1 ~ 0.5Mpa condition, reaction 0.2 ~ 2h.
6. the hydrogenation decomposition method of cyclohexyl hydroperoxide as claimed in claim 1, is characterized in that: after hydrogenation reaction, is separated by catalyst filtration, can be recycled after the catalyzer drying after separation.
7. the hydrogenation decomposition method of cyclohexyl hydroperoxide as claimed in claim 1, it is characterized in that: after hydrogenation reaction, alkali cleaning temperature is 60-100 DEG C, and the volume ratio of alkali lye and reaction solution is 1:5-100.
8. the hydrogenation decomposition method of cyclohexyl hydroperoxide as claimed in claim 1, it is characterized in that: after hydrogenation reaction, the temperature of washing is 60-100 DEG C, and the volume ratio of water and reaction solution is 1:5-100.
9. the hydrogenation decomposition method of cyclohexyl hydroperoxide as claimed in claim 1, is characterized in that: water used is distilled water or de-salted water.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105315128A (en) * | 2015-10-28 | 2016-02-10 | 衢州群颖化学科技有限公司 | Method for preparing KA oil through cyclohexane oxidation |
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| CN1246841A (en) * | 1997-02-11 | 2000-03-08 | 纳幕尔杜邦公司 | Hydroperoxide decomposition process |
| CN1600761A (en) * | 2003-09-28 | 2005-03-30 | 中国石油化工股份有限公司 | Method for preparing relevant alcohol and ketone by adding hydrogen into hydroperoxide of hydrocarbon |
| EP2062867A2 (en) * | 2007-11-21 | 2009-05-27 | Sumitomo Chemical Company, Limited | Process for Producing Cycloalkanol and/or Cycloalkanone |
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2014
- 2014-09-16 CN CN201410470601.9A patent/CN104326870A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1246841A (en) * | 1997-02-11 | 2000-03-08 | 纳幕尔杜邦公司 | Hydroperoxide decomposition process |
| CN1600761A (en) * | 2003-09-28 | 2005-03-30 | 中国石油化工股份有限公司 | Method for preparing relevant alcohol and ketone by adding hydrogen into hydroperoxide of hydrocarbon |
| EP2062867A2 (en) * | 2007-11-21 | 2009-05-27 | Sumitomo Chemical Company, Limited | Process for Producing Cycloalkanol and/or Cycloalkanone |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105315128A (en) * | 2015-10-28 | 2016-02-10 | 衢州群颖化学科技有限公司 | Method for preparing KA oil through cyclohexane oxidation |
| CN105315128B (en) * | 2015-10-28 | 2017-04-12 | 江西科苑生物药业有限公司 | Method for preparing KA oil through cyclohexane oxidation |
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Application publication date: 20150204 |