CN105175234A - Synthetic method for dodecyl diphenyl ether - Google Patents
Synthetic method for dodecyl diphenyl ether Download PDFInfo
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- CN105175234A CN105175234A CN201510438279.6A CN201510438279A CN105175234A CN 105175234 A CN105175234 A CN 105175234A CN 201510438279 A CN201510438279 A CN 201510438279A CN 105175234 A CN105175234 A CN 105175234A
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- China
- Prior art keywords
- dodecyl diphenyl
- synthetic method
- diphenyl ether
- catalyst
- diphenyl oxide
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- 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
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A synthetic method for dodecyl diphenyl ether, relating to alkyl diphenyl ether. The invention provides the synthetic method for dodecyl diphenyl ether, wherein the raw materials are wide in source, the product yield is high, the production cost is low and the operating process is simple. The synthetic method comprises: adding a catalyst, diphenyl ether and dodecanol into a heatable reactor; after reaction, carrying out filtration to remove the catalyst; and distilling the filtrate at a reduced pressure to obtain the product dodecyl diphenyl ether. The preparation method for the catalyst comprises: mixing montmorillonite and an aqueous solution of ferric trichloride; stirring the mixture for 3-5 hours; then carrying out suction filtration for the mixed liquid; washing a filter cake by deionized water till no chlorine ions can be detected in the filtrate, and then activating the filtrate at 100-200 DEG C for 8-24 hours to obtain the loaded catalyst. The used catalyst is simple in preparation process, low in cost and free of corrosion on equipment, and is relatively easily recycled. The process for preparing the dodecyl diphenyl ether is simple in operating process, and the yield of the dodecyl diphenyl ether reaches over 90%.
Description
Technical field
The present invention relates to alkyl diphenyl ether, especially relate to a kind of synthetic method of dodecyl diphenyl oxide.
Background technology
P alkylphenylaceticacid is the anion surfactant of a class excellent performance, is widely used in the fields such as oil production, textile printing and dyeing, soil sanitation.Alkyl diphenyl ether, as the important intermediate of this kind of tensio-active agent, receives much concern, and is usually reacted by alkylating reagent and phenyl ether and prepares.The conventional alkylating reagent of alkyl diphenyl ether alkylation has alkene, alcohol, haloalkane, wherein alkene and haloalkane expensive, production cost is higher, therefore prepares alkyl diphenyl ether using alcohol as alkylating reagent and has more industrial prospect.
Current synthesis of alkyl phenyl ether catalyzer used mainly contains BF
3, AlCl
3, H
2sO
4, ionic liquid and solid acid etc.US Patent No. 2390835 is with BF
3for catalyzer, P
2o
5for dodecyl diphenyl oxide prepared by promotor, product yield is 66%, and costly, processing condition are harsh for the method catalyzer used, and environmental pollution is serious, is not suitable for suitability for industrialized production.Chinese patent CN101503379A is with AlCl
3for catalyst preparing alkyl diphenyl ether, the method technique that this patent provides is more complicated, and aftertreatment technology is loaded down with trivial details, product separation purification difficult, and the aluminum bearing waste contaminate environment produced.Chinese patent CN1915969A is with H
2sO
4for catalyst preparing dodecyl diphenyl oxide, the method side reaction that this patent provides is many, purification of products difficulty, and produces a large amount of acid water pollution environment.Chinese patent CN1524839A take ionic liquid as catalyst preparing alkyl diphenyl ether, ionic liquid expensive, complicated process of preparation, and the consumption of this patent intermediate ion liquid is large, and production cost is high, is not suitable for suitability for industrialized production.Chinese patent CN101811945 take atlapulgite as Primary Catalysts, prepare alkyl diphenyl ether using tosic acid, thionamic acid, sulfuric acid, phosphoric acid, phospho-wolframic acid, ferric sulfate as promotor, when this method is promotor with tosic acid, thionamic acid, sulfuric acid, phosphoric acid, phospho-wolframic acid etc., the yield of alkyl diphenyl ether only has about 60%; When taking ferric sulfate as promotor, product yield is only 38%; And promotor is mostly acidic substance, serious to equipment corrosion, aftertreatment is complicated, and environmental pollution is serious.
Summary of the invention
The object of the invention is to overcome existing technique shortcoming, supplying raw materials, source is wide, product yield is high, production cost is low, the synthetic method of the simple a kind of dodecyl diphenyl oxide of operating procedure.
Concrete steps of the present invention are as follows:
Catalyzer, phenyl ether, lauryl alcohol being joined can in reactor heating, and Filtration of catalyst after reaction, carries out underpressure distillation to filtrate, obtain product dodecyl diphenyl oxide.
The loaded catalyst that described catalyzer can adopt montmorillonite and iron trichloride to prepare, the consumption of iron trichloride can be 0 ~ 150% of montmorillonite by mass percentage.
The consumption of described catalyzer can be 4% ~ 20% of lauryl alcohol and phenyl ether total mass by mass percentage, and the mol ratio of phenyl ether and lauryl alcohol can be (1 ~ 4): 1; The temperature of described reaction can be 150 ~ 200 DEG C, and the time of reaction can be 3 ~ 10h.
The preparation method of described loaded catalyst can be:
By the aqueous solution of montmorillonite and iron trichloride, after stirring 3 ~ 5h, suction filtration is carried out to mixed solution, after inspection does not measure chlorion in filter cake deionized water wash to filtrate, then activate 8 ~ 24h at 100 ~ 200 DEG C, obtain loaded catalyst.Described detection can utilize silver nitrate solution to detect.
Compared with the synthesis technique of existing dodecyl diphenyl oxide, the present invention has the following advantages:
1) catalyst preparation process used is simple, catalyzer is with low cost, corrosion-free and more easy to be recycled to equipment.
2) yield of simple, the dodecyl diphenyl oxide of technique, the operating procedure preparing dodecyl diphenyl oxide of the present invention is up to more than 90%.
Accompanying drawing explanation
Fig. 1 is the mass spectrum of the embodiment of the present invention.
Embodiment
Embodiment 1
First prepare loaded catalyst, the consumption of iron trichloride is 100% of montmorillonite quality.Catalyzer, phenyl ether, lauryl alcohol are joined in reactor, catalyst levels is 17% of lauryl alcohol and phenyl ether total mass, the mol ratio of phenyl ether and lauryl alcohol is 1: 1,5h is reacted at 170 DEG C, filter and remove catalyzer, carry out underpressure distillation to filtrate and obtain product dodecyl diphenyl oxide, yield is 93%.
Proton nmr spectra is as follows:
1HNMR(400MHZ,CDCl3,ppm)δ:0.83-0.89(m,3H),1.18-1.26(m,18H)1.49-1.59(m,4H),6.90-6.94(m,2H),7.0-7.02(m,2H),7.05-7.04(m,3H),7.28-7.35(m,2H)
High resolution mass spectrum figure is see Fig. 1, and the molecular weight of single dodecyl diphenyl oxide is 338.26097, m/z=339.26806, is APCI (M+H)
+peak, the molecular weight of sample and the theoretical molecular of target product hexadecyl diphenyloxide match.
Embodiment 2
First prepare loaded catalyst, the consumption of iron trichloride is 150% of montmorillonite quality.Catalyzer, phenyl ether, lauryl alcohol are joined in reactor, catalyst levels is 13% of lauryl alcohol and phenyl ether total mass, the mol ratio of phenyl ether and lauryl alcohol is 1: 1, after reacting 5h at 170 DEG C, filter and remove catalyzer, carry out underpressure distillation to filtrate and obtain product dodecyl diphenyl oxide, yield is 84%.
Embodiment 3
First prepare loaded catalyst, the consumption of iron trichloride is 150% of montmorillonite quality.Catalyzer, phenyl ether, lauryl alcohol are joined in reactor, catalyst levels is 17% of lauryl alcohol and phenyl ether total mass, the mol ratio of phenyl ether and lauryl alcohol is 1: 1,5h is reacted at 170 DEG C, filter and remove catalyzer, carry out underpressure distillation to filtrate and obtain product dodecyl diphenyl oxide, yield is 89%.
Embodiment 4
First prepare loaded catalyst, the consumption of iron trichloride is 100% of montmorillonite quality.Catalyzer, phenyl ether, lauryl alcohol are joined in reactor, catalyst levels is 17% of lauryl alcohol and phenyl ether total mass, the mol ratio of phenyl ether and lauryl alcohol is 1: 1,5h is reacted at 180 DEG C, filter and remove catalyzer, carry out underpressure distillation to filtrate and obtain product dodecyl diphenyl oxide, yield is 83%.
Embodiment 5
First prepare loaded catalyst, the consumption of iron trichloride is 100% of montmorillonite quality.Catalyzer, phenyl ether, lauryl alcohol are joined in reactor, catalyst levels is 13% of lauryl alcohol and phenyl ether total mass, the mol ratio of phenyl ether and lauryl alcohol is 2: 1, after reacting 5h at 170 DEG C, filter and remove catalyzer, carry out underpressure distillation to filtrate and obtain product dodecyl diphenyl oxide, yield is 84%.
Embodiment 6
First prepare loaded catalyst, the consumption of iron trichloride is 100% of montmorillonite quality.Catalyzer, phenyl ether, lauryl alcohol are joined in reactor, catalyst levels is 17% of lauryl alcohol and phenyl ether total mass, the mol ratio of phenyl ether and lauryl alcohol is 2: 1, after reacting 5h at 160 DEG C, filter and remove catalyzer, carry out underpressure distillation to filtrate and obtain product dodecyl diphenyl oxide, yield is 79%.
Embodiment 7
First prepare loaded catalyst, the consumption of iron trichloride is 100% of montmorillonite quality.Catalyzer, phenyl ether, lauryl alcohol are joined in reactor, catalyst levels is 17% of lauryl alcohol and phenyl ether total mass, the mol ratio of phenyl ether and lauryl alcohol is 2: 1, after reacting 7h at 150 DEG C, suction filtration removes catalyzer, carry out underpressure distillation to filtrate and obtain product dodecyl diphenyl oxide, yield is 72%.
Embodiment 8
Montmorillonite, phenyl ether, lauryl alcohol are joined in reactor, the consumption of montmorillonite is 20% of lauryl alcohol and phenyl ether total mass, the mol ratio of phenyl ether and lauryl alcohol is 2: 1,10h is reacted at 180 DEG C, Filtration of catalyst, carry out underpressure distillation to filtrate and obtain product dodecyl diphenyl oxide, yield is 52%.
Dodecyl diphenyl oxide synthetic method provided by the invention, has the advantages such as raw material sources are wide, product yield is high, production cost is low, operating procedure is simple.
Claims (6)
1. a synthetic method for dodecyl diphenyl oxide, is characterized in that its concrete steps are as follows:
Catalyzer, phenyl ether, lauryl alcohol being joined can in reactor heating, and Filtration of catalyst after reaction, carries out underpressure distillation to filtrate, obtain product dodecyl diphenyl oxide.
2. the synthetic method of a kind of dodecyl diphenyl oxide as claimed in claim 1, it is characterized in that the loaded catalyst that described catalyzer adopts montmorillonite and iron trichloride and prepares, the consumption of iron trichloride is 0 ~ 150% of montmorillonite by mass percentage.
3. the synthetic method of a kind of dodecyl diphenyl oxide as claimed in claim 1, the consumption that it is characterized in that described catalyzer is 4% ~ 20% of lauryl alcohol and phenyl ether total mass by mass percentage, and the mol ratio of phenyl ether and lauryl alcohol is (1 ~ 4): 1.
4. the synthetic method of a kind of dodecyl diphenyl oxide as claimed in claim 1, it is characterized in that the temperature of described reaction is 150 ~ 200 DEG C, the time of reaction is 3 ~ 10h.
5. the synthetic method of a kind of dodecyl diphenyl oxide as claimed in claim 2, is characterized in that the preparation method of described loaded catalyst is:
By the aqueous solution of montmorillonite and iron trichloride, after stirring 3 ~ 5h, suction filtration is carried out to mixed solution, after inspection does not measure chlorion in filter cake deionized water wash to filtrate, then activate 8 ~ 24h at 100 ~ 200 DEG C, obtain loaded catalyst.
6. the synthetic method of a kind of dodecyl diphenyl oxide as claimed in claim 5, is characterized in that described detection utilizes silver nitrate solution to detect.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510438279.6A CN105175234A (en) | 2015-07-23 | 2015-07-23 | Synthetic method for dodecyl diphenyl ether |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510438279.6A CN105175234A (en) | 2015-07-23 | 2015-07-23 | Synthetic method for dodecyl diphenyl ether |
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|---|---|
| CN105175234A true CN105175234A (en) | 2015-12-23 |
Family
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|---|---|---|---|
| CN201510438279.6A Pending CN105175234A (en) | 2015-07-23 | 2015-07-23 | Synthetic method for dodecyl diphenyl ether |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109970521A (en) * | 2019-05-09 | 2019-07-05 | 福建师范大学 | A kind of preparation method of dodecyl diphenyl oxide |
-
2015
- 2015-07-23 CN CN201510438279.6A patent/CN105175234A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| 王玉丰等: "烷基二苯醚二磺酸盐的研究进展", 《精细与专用化学品》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109970521A (en) * | 2019-05-09 | 2019-07-05 | 福建师范大学 | A kind of preparation method of dodecyl diphenyl oxide |
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Application publication date: 20151223 |
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