CN105693478A - Preparation method for converting ortho-position ethyl vanillin into ethoxyphenol - Google Patents
Preparation method for converting ortho-position ethyl vanillin into ethoxyphenol Download PDFInfo
- Publication number
- CN105693478A CN105693478A CN201610150901.8A CN201610150901A CN105693478A CN 105693478 A CN105693478 A CN 105693478A CN 201610150901 A CN201610150901 A CN 201610150901A CN 105693478 A CN105693478 A CN 105693478A
- Authority
- CN
- China
- Prior art keywords
- ethyl vanillin
- ethoxyphenol
- ortho
- catalyst
- position ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
- B01J27/13—Platinum group metals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the field of organic synthesis and particularly relates to a preparation method for converting ortho-position ethyl vanillin into ethoxyphenol. The method comprises the following steps: 1, adding an appropriate amount of ortho-position ethyl vanillin into a reaction kettle, and heating the ortho-position ethyl vanillin so that the ortho-position ethyl vanillin can be molten to be in the liquid state; 2, starting stirring, and adding a composite catalyst into the reaction kettle; 3, conducting heating and raising the temperature to 120-160 DEG C, conducting a reaction, and conducting a backflow reaction for 1-5 hours; 4, conducting press filtering, and recycling the composite catalyst; 5, conducting simple distillation on filtrate, so that a product, namely ethoxyphenol, is obtained, wherein the mass ratio of the ortho-position ethyl vanillin to the ethoxyphenol is 1: (0.01-0.07). By means of the preparation method, the problem that at present, ortho-position ethyl vanillin cannot be disposed is solved, an ethyl vanillin manufacturer can synthesize ortho-position ethyl vanillin into ethoxyphenol independently by means of the method, accumulation of ortho-position ethyl vanillin is reduced, it is beneficial to cycle use of chemical raw materials, and environmental pollution is reduced.
Description
Technical field
The invention belongs to organic synthesis field, the preparation method that particularly a kind of ortho position ethyl vanillin is converted into o-ethoxyphenol。
Background technology
Ortho position ethyl vanillin, chemical name: 2-hydroxyl-3-ethoxy-benzaldehyde, have another name called 3-ethyoxyl salicylide, molecular formula is C9H10O3, its chemical structural formula is:
Faint yellow acicular crystal, fusing point 66-68 DEG C, boiling point 263-264 DEG C, for producing the by-product produced in ethyl vanillin process, because itself also having color and luster, and fragrance is not good, seldom it is used as spice to use, more using as medicine intermediate and brightening agent, market demand is little, causes that ortho position ethyl vanillin is hoarded。Ortho position ethyl vanillin is deposited in outdoor, certainly will cause environmental pollution；It is deposited in indoor, storehouse, wasting space certainly will be taken。Therefore, the process of ortho position ethyl vanillin is a great problem producing ethyl vanillin producer at present。
O-ethoxyphenol is a kind of important industrial chemicals, is also a kind of important fine-chemical intermediate simultaneously, and chemical products are mainly ethyl vanillin downstream。It is widely used in the synthesis technique of medicine, spice, fuel, cosmetics, antioxidant and polymerization inhibitor, particularly in the technique of synthesis ethyl vanillin, and the huge market demand。
Summary of the invention
The technical problem to be solved is to provide the preparation method that a kind of ortho position ethyl vanillin is converted into o-ethoxyphenol, ortho position ethyl vanillin can be converted into the o-ethoxyphenol that demand is big by this synthetic method, thus reducing hoarding of ortho position ethyl vanillin, and be conducive to the recycling of chemical raw material, reduce environmental pollution。
In order to solve above-mentioned technical problem, the present invention provides following technical scheme:
The preparation method that a kind of ortho position ethyl vanillin is converted into o-ethoxyphenol, comprises the following steps:
A. adding in reactor by appropriate ortho position ethyl vanillin, heating makes it melted be in a liquid state；
B. open stirring, in reactor, add appropriate composite catalyst；
C. 120 DEG C～160 DEG C reactions, back flow reaction 1～5 hour it are heated to；
D. composite catalyst is reclaimed in filter pressing；
E. filtrate carries out simple distillation and namely obtains product o-ethoxyphenol。
Described composite catalyst is at least two XaYbType catalyst forms, and X is the one in platinum, cobalt, ruthenium, rhodium, palladium metal, and Y is mainly by the one in halogen, oxygen atom；
Described ortho position ethyl vanillin and composite catalyst mass ratio: 1:0.01～0.07。
O-ethoxyphenol synthetic reaction formula of the present invention is as follows:
Compared with prior art, advantage is in that the present invention:
1. this method product yield >=95%, and can obtain, through simple distillation, the o-ethoxyphenol that purity is more than 99%；
2. present invention process is simple, and product simple distillation qualified products, produce and do not need to put into the equipment such as rectifying column, and catalyst reclaim after can be recycled through simple process, production cost is low；
3. the present invention does not adopt solvent, it is to avoid uses the major safety problems that combustible metal catalyst is likely to occur when solvent exists, and produces without waste water, safety and environmental protection, is conducive to the plant layout to produce；
4. main this great problem that cannot process being to solve current ortho position ethyl vanillin, ortho position ethyl vanillin can be about to certainly by the method for present invention synthesis o-ethoxyphenol by the producer producing ethyl vanillin, decrease ortho position ethyl vanillin to hoard, and be conducive to the recycling of chemical raw material, reduce environmental pollution。
Further, described composite catalyst is Rh2O3And RuCl3Mixture, Rh2O3And RuCl3Mass ratio be 1:3。
The yield of the product that experiment proof this catalyst combination draws is the highest, and up to more than 97%, and product purity is the highest, can be higher than 99.5%。
Further, also include catalyst recovery method: will the catalyst that obtain after step d filter pressing be incorporated in 95% alcoholic solution of its quality 1～2 times, filter after stirring 1～2 hour under room temperature, then the 5% sodium hydroxide solution washing with 1～2 times of catalyst quality, after filtration。
The recovery method of the present invention is simply effective, effectively by attachment eluting on catalyst, can being conducive to the recycling again of catalyst, reducing catalyst waste, thus saving cost。
Accompanying drawing explanation
Fig. 1 is the gas chromatogram of the product of embodiments of the invention 1；
Fig. 2 is the gas chromatogram of the product of embodiments of the invention 2；
Fig. 3 is the gas chromatogram of the product of embodiments of the invention 3；
Fig. 4 is the gas chromatogram of the product of embodiments of the invention 4。
Detailed description of the invention
Embodiment 1
The preparation method of a kind of o-ethoxyphenol, comprises the following steps:
A. being added in reactor by 20.07g ortho position ethyl vanillin crystalline solid, heating makes it melted be in a liquid state；
B. open stirring, in still, add 0.4013g composite metal catalyst (Ir2O3With PtCl4Form with mass ratio 1:4 proportioning)；
C. it is heated at 140 DEG C and reacts 2 hours；
D. filter pressing Footwall drift catalyst；
E. filtrate decompression is distilled and obtains product。
Product is colourless transparent liquid 15.88g, molar product yield 95.16%, as it is shown in figure 1, product G C purity is 99.08%。
Embodiment 2
The preparation method of a kind of o-ethoxyphenol, comprises the following steps:
A. being added in reactor by 300.02g ortho position ethyl vanillin crystalline solid, heating makes it melted be in a liquid state；
B. open stirring, in still, add 4.5023g composite metal catalyst (Ir2O3And PdCl2Mass ratio 1:3.5 proportioning forms)；
C. it is heated at 155 DEG C and reacts 3 hours；
D. filter pressing Footwall drift catalyst；
E. filtrate decompression is distilled and obtains product。
Product is colourless transparent liquid 242.50g, molar product yield: 96.91%, and content is as in figure 2 it is shown, GC purity: 99.56%。
Embodiment 3
The preparation method of a kind of o-ethoxyphenol, comprises the following steps:
A. being added in reactor by 100.02g ortho position ethyl vanillin crystalline solid, heating makes it melted be in a liquid state；
B. open stirring, in still, add 5.0237g composite metal catalyst (Rh2O3And PdCl2Mass ratio 1:3 proportioning forms)；
C. it is heated at 155 DEG C and reacts 3 hours；
D. filter pressing Footwall drift catalyst；
E. filtrate decompression is distilled and obtains product；
F. also include catalyst recovery method: the catalyst obtained after step d filter pressing will add 95% alcoholic solution of 10g, filter after stirring 1～2 hour under room temperature, add the 5% sodium hydroxide solution washing of 10g, after filtration。
Product is colourless transparent liquid 79.85g, molar product yield: 96.01%, and content is as it is shown on figure 3, GC purity: 99.49%。
Embodiment 4
The preparation method of a kind of o-ethoxyphenol, comprises the following steps:
A. being added in reactor by 100.13g ortho position ethyl vanillin crystalline solid, heating makes it melted be in a liquid state；
B. open stirring, in still, add 2.0008g composite metal catalyst (Rh2O3And RuCl3Mass ratio 1:3 proportioning forms)；
C. it is heated at 150 DEG C and reacts 4 hours；
D. filter pressing Footwall drift catalyst；
E. filtrate decompression is distilled and obtains product。
Product is colourless transparent liquid 81.23g, molar product yield 97.56%, content as shown in Figure 4, GC purity: 99.66%。
From the above it follows that catalyst adopts Rh2O3And RuCl3Mixture, Rh2O3And RuCl3Mass ratio be
During 1:3, the yield of product is the highest, and product purity is the highest。
Above-described is only the preferred embodiment of the present invention; should be understood that; for a person skilled in the art; under the premise without departing from present configuration; some deformation and improvement can also be made; these also should be considered as protection scope of the present invention, and these are all without affecting effect of the invention process and practical applicability。
Claims (3)
1. the preparation method that an ortho position ethyl vanillin is converted into o-ethoxyphenol, it is characterised in that comprise the following steps:
A. adding in reactor by appropriate ortho position ethyl vanillin, heating makes it melted be in a liquid state；
B. open stirring, in reactor, add composite catalyst；
C. 120 DEG C～160 DEG C reactions, back flow reaction 1～5 hour it are heated to；
D. composite catalyst is reclaimed in filter pressing；
E. filtrate carries out simple distillation and namely obtains product o-ethoxyphenol；
Described composite catalyst is at least two XaYbType catalyst forms, and X is the one in platinum, cobalt, ruthenium, rhodium, palladium metal, and Y is mainly by the one in halogen, oxygen atom；
Described ortho position ethyl vanillin and composite catalyst mass ratio: 1:0.01～0.07。
2. the preparation method that ortho position as claimed in claim 1 ethyl vanillin is converted into o-ethoxyphenol, it is characterised in that:
Described composite catalyst is Rh2O3And RuCl3Mixture, Rh2O3And RuCl3Mass ratio be 1:3。
3. the preparation method that ortho position as claimed in claim 1 ethyl vanillin is converted into o-ethoxyphenol, it is characterized in that: also include catalyst recovery method: the catalyst obtained after step d filter pressing will be incorporated in 95% alcoholic solution of its quality 1 ~ 2 times, filter after stirring 1 ~ 2 hour under room temperature, again with 5% sodium hydroxide solution washing of 1 ~ 2 times of catalyst quality, after filtration。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610150901.8A CN105693478A (en) | 2016-03-16 | 2016-03-16 | Preparation method for converting ortho-position ethyl vanillin into ethoxyphenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610150901.8A CN105693478A (en) | 2016-03-16 | 2016-03-16 | Preparation method for converting ortho-position ethyl vanillin into ethoxyphenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105693478A true CN105693478A (en) | 2016-06-22 |
Family
ID=56221785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610150901.8A Pending CN105693478A (en) | 2016-03-16 | 2016-03-16 | Preparation method for converting ortho-position ethyl vanillin into ethoxyphenol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105693478A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108947780A (en) * | 2018-07-23 | 2018-12-07 | 重庆欣欣向荣精细化工有限公司 | A method of rectifying high-boiling components in processing Ethyl vanillin preparation |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4897827A (en) * | 1972-03-30 | 1973-12-13 | ||
| CN1179414A (en) * | 1996-08-30 | 1998-04-22 | 宇部兴产株式会社 | Catalyst for decarbonylation reaction |
| CN104045537A (en) * | 2014-06-24 | 2014-09-17 | 上海应用技术学院 | Method for treating 5-aldehyde vanillin side product in vanillin production process |
-
2016
- 2016-03-16 CN CN201610150901.8A patent/CN105693478A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4897827A (en) * | 1972-03-30 | 1973-12-13 | ||
| CN1179414A (en) * | 1996-08-30 | 1998-04-22 | 宇部兴产株式会社 | Catalyst for decarbonylation reaction |
| CN104045537A (en) * | 2014-06-24 | 2014-09-17 | 上海应用技术学院 | Method for treating 5-aldehyde vanillin side product in vanillin production process |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108947780A (en) * | 2018-07-23 | 2018-12-07 | 重庆欣欣向荣精细化工有限公司 | A method of rectifying high-boiling components in processing Ethyl vanillin preparation |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102757308A (en) | Method of preparing high-purity ethanol | |
| CN101103725A (en) | Cartap environment-friendly type preparing method | |
| CN102633657A (en) | Preparation method of cis-3-amino-cyclopentanol hydrochloride | |
| CN101092407B (en) | Method for preparing alpha - acetyl - gamma - butyrolactone | |
| CN115073275A (en) | Preparation method of photoinitiator 1-hydroxycyclohexyl phenyl ketone | |
| CN111393272A (en) | Synthetic method of 3' -methyl propiophenone | |
| CN105693478A (en) | Preparation method for converting ortho-position ethyl vanillin into ethoxyphenol | |
| CN108440236B (en) | Method for reducing organic halide by semiconductor photocatalytic hydrogenation | |
| CN104829559B (en) | A kind of method that γ valerolactone is prepared by methyl ester levulinate | |
| CN103755529B (en) | A kind of method preparing pyrogallol and Phloroglucinol monomethyl ether | |
| CN110590706B (en) | Preparation method of N-methylpyrrolidine | |
| CN103274982B (en) | Levulinic acid transforms the method generating lactan | |
| CN103058984B (en) | Synthesis method of watermelon ketone | |
| CN103232333B (en) | A kind of preparation method of ring third acetylene important intermediate Cyclopropyl Methyl Ketone | |
| CN104193701B (en) | A kind of synthetic method of 3-hydroxymethyl tetrahydrofuran | |
| CN1810787A (en) | Prepn process of methyl pyrrolidine | |
| CN1990456A (en) | Method for production of N, N dimethyl cyclohexylamine | |
| CN109569595B (en) | Catalytic system for preparing cyclohexene Ru through benzene selective hydrogenation, and preparation method and application thereof | |
| CN1876638A (en) | Process for preparing benzoguanamine | |
| CN110452112B (en) | Catalytic hydrogenation treatment process for chloro pivaloyl chloride rectification residual liquid | |
| CN103435477A (en) | Novel method for synthesizing para-ethoxybenzoic acid | |
| CN108929254B (en) | Synthesis method of selenium methyl selenocysteine | |
| CN113372262A (en) | Preparation method of trans-3, 5-dimethylpiperidine | |
| CN108456139B (en) | Device and method for preparing dibutyl phthalate by batch catalytic reaction rectification | |
| CN103012094B (en) | Synthesis method of ionone-type spice intermediate products |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20160622 |