CN104693002A - Method for preparing benzaldehyde by toluene oxidation - Google Patents
Method for preparing benzaldehyde by toluene oxidation Download PDFInfo
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- CN104693002A CN104693002A CN201510108688.XA CN201510108688A CN104693002A CN 104693002 A CN104693002 A CN 104693002A CN 201510108688 A CN201510108688 A CN 201510108688A CN 104693002 A CN104693002 A CN 104693002A
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- toluene
- selectivity
- oxide
- phenyl aldehyde
- metal
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- 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
- C07C45/33—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 CHx-moieties
- C07C45/34—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 CHx-moieties in unsaturated compounds
- C07C45/36—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 CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The invention discloses a preparation method of benzaldehyde. According to the method disclosed by the invention, by taking toluene as a raw material, a metal as well as a metal oxide loaded on a carrier as a catalyst, peroxide as a co-catalyst, oxygen as an oxygen source and methanol as a reaction solvent, the reaction time is 1-80 hours, the reaction temperature is 25-120 DEG C, the pressure is 0.1-6.0MPa, the conversion rate can reach 10-50% and the selectivity can reach 60-90%. The method disclosed by the invention has the advantages of simple process, low cost, environmental friendliness, low energy consumption, high authenticity of benzaldehyde, easily separable and reusable catalyst and the like.
Description
Technical field
The present invention relates to a kind of method preparing phenyl aldehyde, particularly relate to a kind of method of preparing benzaldehyde by oxidizing toluene.
Background technology
Phenyl aldehyde is extensively present in vegitabilia, particularly in rosaceous plant, is mainly present in the stem skin of plant, leaf or seed with the form of glycosides, such as, amygdaloside in Semen Armeniacae Amarum.Phenyl aldehyde is natural to be present in Semen Armeniacae Amarum oil, oil of Herba Pogostemonis, hyacinth oil, ylang-ylang wet goods essential oil.Sometimes also Semen Armeniacae Amarum oil is claimed.Phenyl aldehyde is as important industrial chemicals, for lauryl aldehyde processed, lauric acid, phenylacetic aldehyde and peruscabin etc., also can be used as measuring ozone, phenol, alkaloid and being positioned at the other methylene reagents of carboxyl, also can be used as the fragrant spices of special head, trace is used for fragrance of a flower formula.
The industrial process of traditional phenyl aldehyde mainly contains three major types: respectively with toluene, phenylcarbinol and benzene for raw material.The pressurization method of substitution of chlorination toluene hydrolysis method, benzyl alcohol oxidation method, benzene again
The industrial process of traditional phenyl aldehyde all exist seriously polluted, toxicity large, high in cost of production shortcoming, therefore, can for the deficiency of existing technique, work out the novel process that a kind of environmentally friendly and technique prepares phenyl aldehyde simply simultaneously and be of great practical significance.
At present, toluene direct oxidation under gas phase or liquid-phase condition generates the method that phenyl aldehyde is comparatively economy and environmental protection, the focus that everybody pays close attention to is become at green oxidation toluene in recent years, be in the Chinese patent of CN1528726 as far back as the patent No. in 2004, disclose a kind of in acidity or neutral ion liquid and acetic acid mixed solvent, the method of phenyl aldehyde is prepared by liquid-phase oxidation toluene, toluene is oxidized under 115-120 DEG C of condition, when toluene conversion is 42%, the selectivity of phenyl aldehyde is only 48%, this method employs expensive ionic liquid and acetate solvate in a large number, substantially increase production cost, and product separation is comparatively difficult, industrial production is uneconomical.The Dalian Chemistry and Physics Institute discloses a kind of preparation method of the catalyzer for preparing benzaldehyde by oxidizing toluene at patent CN02143361.5.The active ingredient of this catalyzer is zirconium and the main group metal etc. such as other transition metal, basic metal or alkaline-earth metal, IIIA, IVA, VA.Use this catalyzer, at temperature 180-195 DEG C, pass into oxygen, react under pressure 0.8-1.2MPa condition, during toluene conversion 13.0%, the selectivity of phenyl aldehyde is 86.6%.The method catalyst preparation process more complicated, and be oxidized the wayward stage at aldehyde, more easily generate phenylformic acid.CN200410065322.0 discloses the catalyzer of a kind of highly selective gas phase oxidation of toluene legal system for phenyl aldehyde, and the selectivity of its phenyl aldehyde reaches as high as 94.4%.But the method temperature of reaction high (320-420 DEG C), technique is restive compared with liquid phase oxidation, and industrial prospect is also pessimistic.CN200510020671.5 uses base metal vanadium and molybdenum load to make catalyzer on aluminium sesquioxide, make oxygenant with hydrogen peroxide, make solvent with glacial acetic acid, (normal pressure, 50-90 DEG C) reaction under comparatively gentle condition, phenyl aldehyde selectivity reaches 77%, yield 13%.The method needs acetic acid to make solvent, and need consume a large amount of hydrogen peroxide, and wastewater flow rate is large, complex process.Therefore, although this method reaction conditions is gentle, be difficult to realize suitability for industrialized production.2014, the people such as Wei Deng adopt Metalloporphyrins catalyzed oxidation toluene, react under 100 DEG C of conditions, time toluene conversion reaches 41%, the selectivity of phenyl aldehyde is only 28.61%, and this method employs expensive metal complex catalysts, and by product is more, improve production cost, and cause larger pollution.In sum, there is the shortcomings such as complex process, seriously polluted, high cost, high energy consumption, phenyl aldehyde selectivity are low in existing technology.
Therefore the present invention is on the basis of forefathers, catalyzer is changed into metal on carrier of environmental protection, relatively cheap, reusable load and metal oxide thereof, react under 50-100 DEG C of condition, transformation efficiency reaches 10%-50%, and selectivity reaches 60%-98%.
Summary of the invention
The present invention is directed to the defect that prior art exists, a kind of method preparing phenyl aldehyde is provided, effectively can promotes the yield of phenyl aldehyde, reduce the production rate of by product, reduce production cost, decreasing pollution.
Content of the present invention comprises the steps:
By the toluene of 1-10mol/L concentration, the metal of load on carrier and metal oxide thereof are as Primary Catalysts 0.05-1mol/L, promotor 1-5mol/L adds in reactor successively, passing into oxygen to pressure is 0.1-5MPa, raised temperature is to 25-120 DEG C, and condition is carried out reaction 1-80h and monitored by HPLC and obtain productive rate.
Described temperature of reaction is 50-120 DEG C;
Described reaction pressure is 0.2-6MPa;
The described reaction times is 1-80h;
The method of phenyl aldehyde prepared by described catalyzed oxidation toluene, it is characterized in that, described promotor is: one or two or more kinds of hydrogen peroxide, cyclohexanone peroxide, tertbutyl peroxide;
Described carrier is one or two or more kinds in Graphene, molecular sieve, silica gel, sepiolite, chitosan, diatomite, tubular fibre, cyclodextrin, microbial film;
Embodiment
Embodiment 1
Content of the present invention comprises the steps:
By toluene 12g, methanol solvate 150mL, the graphene-supported metallic copper nano particle 0.05g of catalyzer, promotor hydrogen peroxide 70mg adds successively and is full of in the reactor of oxygen, be 70 DEG C in temperature, pressure is that 2.0MPa condition carries out reaction 10h, toluene conversion 6%, phenyl aldehyde selectivity 85%, benzyl alcohol selective 13% and phenylformic acid selectivity 2%.
Embodiment 2
According to the reaction conditions of embodiment 1, unlike metallic copper nano particle being replaced to manganese metal nanometer alcohol selectivity 14% and phenylformic acid selectivity 5%.
Embodiment 3
According to the reaction conditions of embodiment 1, replace to cobalt metal nanoparticle unlike by metallic copper nano particle, monitored by HPLC, obtain productive rate, toluene conversion 11%, phenyl aldehyde selectivity 79%, benzyl alcohol selective 16% and phenylformic acid selectivity 5%.
Embodiment 4
According to the reaction conditions of embodiment 1, replace to 100 DEG C unlike by temperature of reaction, monitored by HPLC, obtain productive rate, toluene conversion 13%, phenyl aldehyde selectivity 70%, benzyl alcohol selective 23% and phenylformic acid selectivity 7%.
Embodiment 5
According to the reaction conditions of embodiment 1, replace to 120 DEG C unlike by temperature of reaction, monitored by HPLC, obtain productive rate, toluene conversion 15%, phenyl aldehyde selectivity 68%, benzyl alcohol selective 24% and phenylformic acid selectivity 8%.
Embodiment 6
According to the reaction conditions of embodiment 1, replace to 4.0MPa unlike by reaction pressure, monitored by HPLC, obtain productive rate, toluene conversion 19%, phenyl aldehyde selectivity 71%, benzyl alcohol selective 19% and phenylformic acid selectivity 10%.
Embodiment 7
According to the reaction conditions of embodiment 1, replace to 6.0MPa unlike by reaction pressure, monitored by HPLC, obtain productive rate, toluene conversion 22%, phenyl aldehyde selectivity 73%, benzyl alcohol selective 16% and phenylformic acid selectivity 11%.
Embodiment 8
According to the reaction conditions of embodiment 1, replace to cyclohexanone peroxide unlike by promotor hydrogen peroxide, monitored by HPLC, obtain productive rate, toluene conversion 25%, phenyl aldehyde selectivity 81%, benzyl alcohol selective 10% and phenylformic acid selectivity 9%.
Embodiment 9
According to the reaction conditions of embodiment 1, replace to tertbutyl peroxide unlike by promotor hydrogen peroxide, monitored by HPLC, obtain productive rate, toluene conversion 28%, phenyl aldehyde selectivity 90%, benzyl alcohol selective 3% and phenylformic acid selectivity 7%.
Embodiment 10
According to the reaction conditions of embodiment 1, different replaces to chitosan by loaded metal carrier Graphene, is monitored, obtains productive rate, toluene conversion 30%, phenyl aldehyde selectivity 92% by HPLC, benzyl alcohol selective 2% and phenylformic acid selectivity 6%.
Embodiment 12
According to the reaction conditions of embodiment 1, different replaces to tubular fibre by loaded metal carrier Graphene hydrogen, is monitored, obtains productive rate, toluene conversion 33%, phenyl aldehyde selectivity 94%, benzyl alcohol selective 1% and phenylformic acid selectivity 5% by HPLC.
Embodiment 13
According to the reaction conditions of embodiment 1, different replaces to 0.4g by the quality 0.05g of catalyzer, is monitored, obtain productive rate by HPLC, toluene conversion 38%, phenyl aldehyde selectivity 89%, benzyl alcohol selective 6% and phenylformic acid selectivity 5%.
Embodiment 14
According to the reaction conditions of embodiment 1, different replaces to 0.6g by the quality 0.05g of catalyzer, is monitored, obtain productive rate by HPLC, toluene conversion 41%, phenyl aldehyde selectivity 95%, benzyl alcohol selective 2% and phenylformic acid selectivity 3%.
Embodiment 15
According to the reaction conditions of embodiment 1, different replaces to 40h by reaction times 10h, is monitored, obtain productive rate by HPLC, toluene conversion 45%, phenyl aldehyde selectivity 88%, benzyl alcohol selective 1% and phenylformic acid selectivity 11%.
Embodiment 16
According to the reaction conditions of embodiment 1, different replaces to 80h by reaction times 10h, is monitored, obtain productive rate by HPLC, toluene conversion 51%, phenyl aldehyde selectivity 85%, benzyl alcohol selective 2% and phenylformic acid selectivity 13%.
Embodiment 17
According to the reaction conditions of embodiment 1, different replaces to copper oxide nano particle by metallic copper nano particle, is monitored by HPLC, obtains productive rate, toluene conversion 47%, phenyl aldehyde selectivity 88%, benzyl alcohol selective 4% and phenylformic acid selectivity 8%.
Embodiment 18
According to the reaction conditions of embodiment 1, different replaces to ferric oxide nano particles by metallic copper nano particle, is monitored by HPLC, obtains productive rate, toluene conversion 46%, phenyl aldehyde selectivity 91%, benzyl alcohol selective 7% and phenylformic acid selectivity 2%.
Embodiment 19
According to the reaction conditions of embodiment 1, different replaces to manganese oxide nanoparticle by metallic copper nano particle, is monitored, obtain productive rate by HPLC, toluene conversion 43%, phenyl aldehyde selectivity 82%, benzyl alcohol selective 9% and phenylformic acid selectivity 9%.
Embodiment 20
According to the reaction conditions of embodiment 1, different replaces to manganese oxide and manganese metal composite nanoparticle by metallic copper nano particle, monitored by HPLC, obtain productive rate, toluene conversion 46%, phenyl aldehyde selectivity 83%, benzyl alcohol selective 11% and phenylformic acid selectivity 6%.
Embodiment 21
According to the reaction conditions of embodiment 1, different replaces to cupric oxide and metallic copper composite nanoparticle by metallic copper nano particle, monitored by HPLC, obtain productive rate, toluene conversion 51%, phenyl aldehyde selectivity 80%, benzyl alcohol selective 13% and phenylformic acid selectivity 7%.
Embodiment 22
According to the reaction conditions of embodiment 1, different replaces to cobalt oxide and cobalt metal composite nanoparticle by metallic copper nano particle, monitored by HPLC, obtain productive rate, toluene conversion 55%, phenyl aldehyde selectivity 90%, benzyl alcohol selective 3% and phenylformic acid selectivity 7%.
The foregoing is only the preferred embodiments of the present invention; do not limit the present invention; for the technician in this field; the present invention can have various change; all make within technical field of the present invention any amendment, equivalent replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (6)
1. a method for preparing benzaldehyde by oxidizing toluene, is characterized in that, comprises following steps:
By the toluene of 1-10mol/L concentration, the metal of load on carrier and metal oxide thereof are as Primary Catalysts 0.05-1mol/L, and promotor 1-5mol/L adds in reactor successively, and passing into oxygen to pressure is 0.1-5MPa, raised temperature is to 25-120 DEG C, and condition carries out reaction 1-80h.
2. the method for preparing benzaldehyde by oxidizing toluene as claimed in claim 1, it is characterized in that, described metal and metal oxide thereof are one in copper, iron, manganese, cobalt, nickel, cupric oxide, ferric oxide, manganese oxide, cobalt oxide, nickel oxide or more than two kinds.
3. the method for preparing benzaldehyde by oxidizing toluene as claimed in claim 1, is characterized in that, carrier is selected from a kind of in Graphene, molecular sieve, silica gel, sepiolite, chitosan, diatomite, tubular fibre, cyclodextrin, microbial film or more than two kinds.
4. the method for preparing benzaldehyde by oxidizing toluene as claimed in claim 1, it is characterized in that, described promotor is: one or two or more kinds in hydrogen peroxide, cyclohexanone peroxide, tertbutyl peroxide.
5. the method for preparing benzaldehyde by oxidizing toluene as claimed in claim 1, it is characterized in that, temperature of reaction is 50-100 DEG C.
6. the method for preparing benzaldehyde by oxidizing toluene as claimed in claim 1, it is characterized in that, reaction pressure is 0.2-3MPa.
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| CN201510108688.XA CN104693002A (en) | 2015-03-11 | 2015-03-11 | Method for preparing benzaldehyde by toluene oxidation |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105126860A (en) * | 2015-07-31 | 2015-12-09 | 齐国良 | Toluene direct oxidation catalyst and preparation method thereof |
| CN106478389A (en) * | 2016-08-26 | 2017-03-08 | 安徽金邦医药化工有限公司 | A kind of preparation method of 1-Phenylethanone. |
| CN106565394A (en) * | 2016-11-14 | 2017-04-19 | 山东金城石墨烯科技有限公司 | Method of using normal pressure oxygen to oxidize aromatic alcohols to prepare aldehyde in presence of graphene supported nano copper powder (catalyst) |
| CN107032969A (en) * | 2017-05-25 | 2017-08-11 | 钦州学院 | The technique that a kind of liquid-phase oxidation of toluene prepares benzaldehyde |
| CN107056594A (en) * | 2017-03-29 | 2017-08-18 | 钦州学院 | Preparation method of benzaldehyde |
| CN108503518A (en) * | 2017-02-28 | 2018-09-07 | 湖南师范大学 | A kind of preparation and its application of compound sepiolite base catalyst |
| CN109482119A (en) * | 2018-12-12 | 2019-03-19 | 西南大学 | A kind of the nano molecular sieve microreactor and preparation method of efficient production benzaldehyde |
| CN109482227A (en) * | 2018-08-30 | 2019-03-19 | 南京大学 | A kind of two-dimensional ultrathin Mo/CuO@SAPO-34 molecular sieve catalytic material and the preparation method and application thereof |
| CN109999826A (en) * | 2019-04-08 | 2019-07-12 | 沈阳化工大学 | A kind of hollow micron tubulose manganese cobalt-base catalyst and preparation method thereof for toluene catalytically purification |
| CN112973725A (en) * | 2021-03-08 | 2021-06-18 | 重庆化工职业学院 | Catalyst for synthesizing sclareolide by oxidizing sclareol |
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| CN101786947A (en) * | 2010-03-18 | 2010-07-28 | 申广照 | Method for preparing benzaldehyde by oxidizing toluene |
| CN102070382A (en) * | 2011-01-19 | 2011-05-25 | 山东瀛洋香精香料有限公司 | Method for preparing benzaldehyde or substituted benzaldehyde by catalytically oxidizing methylbenzene or substituted methylbenzene |
| CN104028269A (en) * | 2014-06-20 | 2014-09-10 | 南京工业大学 | Graphene loaded metal nano composite material, and preparation method and application thereof |
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| US6495726B1 (en) * | 1999-09-16 | 2002-12-17 | Council Of Scientific And Industrial Research | Process for the production of benzaldehyde by the catalytic liquid phase air oxidation of toluene |
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| CN102070382A (en) * | 2011-01-19 | 2011-05-25 | 山东瀛洋香精香料有限公司 | Method for preparing benzaldehyde or substituted benzaldehyde by catalytically oxidizing methylbenzene or substituted methylbenzene |
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Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105126860A (en) * | 2015-07-31 | 2015-12-09 | 齐国良 | Toluene direct oxidation catalyst and preparation method thereof |
| CN105126860B (en) * | 2015-07-31 | 2017-10-31 | 烟台智本知识产权运营管理有限公司 | A kind of toluene direct oxidation catalyst and preparation method thereof |
| CN106478389A (en) * | 2016-08-26 | 2017-03-08 | 安徽金邦医药化工有限公司 | A kind of preparation method of 1-Phenylethanone. |
| CN106565394B (en) * | 2016-11-14 | 2019-08-13 | 山东金城石墨烯科技有限公司 | A kind of graphene-supported Nanometer Copper powder catalysis atmospheric oxygen aoxidizes the fragrant and mellow method for preparing aldehyde |
| CN106565394A (en) * | 2016-11-14 | 2017-04-19 | 山东金城石墨烯科技有限公司 | Method of using normal pressure oxygen to oxidize aromatic alcohols to prepare aldehyde in presence of graphene supported nano copper powder (catalyst) |
| CN108503518A (en) * | 2017-02-28 | 2018-09-07 | 湖南师范大学 | A kind of preparation and its application of compound sepiolite base catalyst |
| CN107056594A (en) * | 2017-03-29 | 2017-08-18 | 钦州学院 | Preparation method of benzaldehyde |
| CN107056594B (en) * | 2017-03-29 | 2020-07-28 | 钦州学院 | Preparation method of benzaldehyde |
| CN107032969A (en) * | 2017-05-25 | 2017-08-11 | 钦州学院 | The technique that a kind of liquid-phase oxidation of toluene prepares benzaldehyde |
| CN109482227A (en) * | 2018-08-30 | 2019-03-19 | 南京大学 | A kind of two-dimensional ultrathin Mo/CuO@SAPO-34 molecular sieve catalytic material and the preparation method and application thereof |
| CN109482227B (en) * | 2018-08-30 | 2021-09-28 | 南京大学 | Two-dimensional ultrathin Mo/CuO @ SAPO-34 molecular sieve catalytic material, and preparation method and application thereof |
| CN109482119A (en) * | 2018-12-12 | 2019-03-19 | 西南大学 | A kind of the nano molecular sieve microreactor and preparation method of efficient production benzaldehyde |
| CN109482119B (en) * | 2018-12-12 | 2021-05-07 | 西南大学 | Nano molecular sieve microreactor for efficiently producing benzaldehyde and preparation method thereof |
| CN109999826A (en) * | 2019-04-08 | 2019-07-12 | 沈阳化工大学 | A kind of hollow micron tubulose manganese cobalt-base catalyst and preparation method thereof for toluene catalytically purification |
| CN112973725A (en) * | 2021-03-08 | 2021-06-18 | 重庆化工职业学院 | Catalyst for synthesizing sclareolide by oxidizing sclareol |
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Application publication date: 20150610 |