CN108558613A - One kind 1,2- bis-（2-（2,6- dimethyl phenoxies）Ethyoxyl）The preparation method of ethane - Google Patents
One kind 1,2- bis-（2-（2,6- dimethyl phenoxies）Ethyoxyl）The preparation method of ethane Download PDFInfo
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- CN108558613A CN108558613A CN201810566670.8A CN201810566670A CN108558613A CN 108558613 A CN108558613 A CN 108558613A CN 201810566670 A CN201810566670 A CN 201810566670A CN 108558613 A CN108558613 A CN 108558613A
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- dichloromethane
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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
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
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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
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
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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
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
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Abstract
The invention discloses a kind of 1,2 two (2 (2,6 dimethyl phenoxy) ethyoxyl) ethane preparation methods, include the following steps：(1) 20 DEG C of stirring, 2,6 xylenols and triethylene-glycol are added in ethyl alcohol water mixed solution, add potassium hydroxide, 82 DEG C of reaction 60h, reaction solution to be extracted 3 times with dichloromethane, obtain dichloromethane extract liquor；(2) dichloromethane extract liquor uses 1M caustic washings 2 times, and saturated sodium-chloride is washed 1 time, anhydrous magnesium sulfate drying, it is evaporated dichloromethane, obtains yellow oily liquid, yellow liquid adds diethyl ether, 35 DEG C of heating, insoluble matter is filtered off, 15 DEG C cooling, cool down 48h, filtering, obtain white powdery solids 1,2 two (2 (2,6 dimethyl phenoxy) ethyoxyl) ethane.Present invention is mainly used for the preparations of 1,2 two (2 (2,6 dimethyl phenoxy) ethyoxyl) ethane.
Description
Technical field
The invention belongs to energetic material fields, and in particular to one kind 1,2- bis- (2- (2,6- dimethyl phenoxy) ethyoxyl)
The preparation method of ethane.
Background technology
1,2- bis- (2- (2,6- dimethyl phenoxy) ethyoxyl) ethane is a kind of important chemicals, it and it derivative
Object can be used for many fields.Wherein using its as the crown ether of structural unit be not only Coordinative Chemistry, analytical chemistry, organic chemistry and
The important research content of bioinorganic chemistry, and suffer from close connection with life science, information science, material science etc.
System.And the calixarenes developed on the basis of crown ether is then by rich pi-electron, the adjustable three-dimensional lumen of size and annular array oxygen original
Son, not only can complex ion but also can inclusion neutral molecule.More importantly, the readily selected sex modification of upper lower edge of calixarenes, it can
Largely there is " pre-organized structure " (Pre- for " structure platform " (Platform orbuilding block) synthesis with it
Organized structure) host molecule.
2004, Chupakhin etc. selected 2,6- xylenols and triethylene-glycol p-methyl benzenesulfonic acid ester is raw material,
Compound 1,2- bis- (2- (2,6- dimethyl phenoxy) ethyoxyl) ethane have been synthesized under potassium hydroxide catalysed.
(O.N.Chupakhin,G.L.Rusinov,N.A.Itsikson.New 1,2,4-triazine-containing
podands:synthesis and properties,Russian Chemical Bulletin,International
Edition,53(10),2308-2313,2004).The synthetic route of Chupakhin methods is as follows：
Chupakhin methods are raw material using triethylene-glycol p-methyl benzenesulfonic acid ester, and triethylene-glycol is to toluene sulphur
Acid esters will be prepared by triethylene glycol and the condensation of p-methyl benzenesulfonic acid acyl chlorides, increase reaction step；Chupakhin methods can generate greatly
By-product p-methyl benzenesulfonic acid potassium is measured, the latter does not allow disposable, increases the pollution of reaction；Chupakhin method post-processing operations
Complexity needs just obtain final product by column chromatography for separation, and total recovery is relatively low, and only 60%.
Invention content
The technical problem to be solved by the present invention is to overcome the deficiencies in the prior art, a kind of reaction step is provided
Less, post-processing approach is clear, higher bis- (2- (2,6- dimethyl phenoxy) ethyoxyl) the ethane preparation sides 1,2- of reaction yield
Method.
The synthetic route of the present invention, for raw material, is catalysis with potassium hydroxide with 2,6- xylenols and triethylene-glycol
Agent, alcohol-water mixed solution are solvent, carry out etherification reaction and obtain product 1, (2- (2, the 6- diformazans of 2- bis- using post-processing
Phenoxyl) ethyoxyl) ethane.
The preparation method of 1,2- bis- (2- (2,6- dimethyl phenoxy) ethyoxyl) ethane of the present invention, 1,2- bis- (2- (2,
6- dimethyl phenoxies) ethyoxyl) ethane structural formula such as shown in (I)：
With 2,6- xylenols and triethylene-glycol for raw material, structural formula as shown in (II) and (III), wraps respectively
Include following steps：
(1) under 20 DEG C~25 DEG C stirrings of temperature, 2,6- xylenols and triethylene-glycol are added to alcohol-water
In mixed solution, then potassium hydroxide is added thereto, is 80 DEG C~85 DEG C reaction 40h~70h, reaction solution dichloromethane in temperature
Alkane extracts 2~3 times, obtains dichloromethane extract liquor；Wherein, the matter of triethylene-glycol, 2,6- xylenols, potassium hydroxide
Amount is than being 1:1.79~2.00:0.72~1, the volume ratio of second alcohol and water is 4:6~6:4；
(2) above-mentioned dichloromethane extract liquor is washed 2~3 times using 1M sodium hydroxide solutions, then uses saturated nacl aqueous solution
It washes 1~2 time, after being dried with anhydrous magnesium sulfate, normal pressure is evaporated dichloromethane, obtains yellow oily liquid；To yellow oily liquid
Ether is added, is warming up to 30 DEG C~35 DEG C, filters off insoluble matter and is cooled to -15 DEG C~-10 DEG C, cool down for 24 hours~48h, filtering solution,
Obtain white powdery solids 1,2- bis- (2- (2,6- dimethyl phenoxy) ethyoxyl) ethane.
The preparation method of currently preferred 1,2- bis- (2- (2,6- dimethyl phenoxy) ethyoxyl) ethane, including it is following
Step：Under (1) 20 DEG C of stirring, 2,6- xylenols and triethylene-glycol are added in alcohol-water mixed solution, then to
Potassium hydroxide is wherein added, is 82 DEG C of reaction 60h in temperature, reaction solution is extracted 3 times with dichloromethane, obtains dichloromethane extraction
Liquid, wherein triethylene-glycol, 2,6- xylenols, potassium hydroxide mass ratio be 1:1.80:0.72；
(2) above-mentioned dichloromethane extract liquor is washed 2 times using 1M sodium hydroxide solutions, then 1 is washed with saturated nacl aqueous solution
Secondary, after being dried with anhydrous magnesium sulfate, normal pressure is evaporated dichloromethane, obtains yellow oily liquid, and second is added to yellow oily liquid
Ether is warming up to 35 DEG C, filters off insoluble matter, is cooled to -15 DEG C, and cool down 48h, and filtering solution obtains white powdery solids 1,2-
Two (2- (2,6- dimethyl phenoxies) ethyoxyl) ethane.
Advantages of the present invention：
(1) reaction step of the present invention is simple, and triethylene-glycol and 2,6- xylenols is directly used to be condensed to yield production
Object, and documents replace triethylene-glycol p-methyl benzenesulfonic acid ester using 2,6- xylenols to obtain product, and two contract
Triethylene glycol p-methyl benzenesulfonic acid ester will be prepared by triethylene-glycol and the condensation of p-methyl benzenesulfonic acid acyl chlorides；
(2) by-product that the present invention generates is potassium chloride, is easily processed, and documents can generate a large amount of by-products to first
Benzene sulfonic acid potassium, it is not easy to handle；The present invention is using more cheap and environmental protection mixed solvent second alcohol and water, and documents use
Higher price, the solvent acetonitrile with certain pollution；
(3) the clear simplicity of post-processing approach of the present invention, is washed, by alkali cleaning, saturated nacl aqueous solution after Diethyl ether recrystallization, pure
Degree reaches 98% or more, and documents need just obtain final product by column chromatography for separation, and post-processing is complicated；The present invention
Preparation method yield it is higher, the total recovery of reaction can reach 81.25%, and the yield in documents is 60%.
Specific implementation mode
The present invention is described in further details with reference to embodiment.
Embodiment 1
Under 20 DEG C of stirrings of temperature, by 1.80g 2,10ml ethyl alcohol-is added in 6- xylenols and 1g triethylene-glycols
In water mixed solution, potassium hydroxide 0.72g is added to it, is warming up to 82 DEG C, after reacting 60h, 3 are extracted using 10ml dichloromethane
It is secondary, obtain dichloromethane extract liquor.
Dichloromethane extract liquor is washed 2 times using 5ml 1M sodium hydroxide solutions, then washes 1 with saturated nacl aqueous solution (20 DEG C)
Secondary, anhydrous magnesium sulfate drying, normal pressure is evaporated dichloromethane, obtains yellow oily liquid；
5ml ether is added to above-mentioned yellow oily liquid, is warming up to 35 DEG C, filters off insoluble matter, is cooled to -15 DEG C, cooling
48h, filtering solution obtain 1.56g white powdery solids 1, and 2- bis- (2- (2,6- dimethyl phenoxy) ethyoxyl) ethane is received
Rate 81.25%, purity 98.44%, 67 DEG C~68 DEG C of fusing point.
Structural Identification：
IR(KBr)ν:3450,3017,2942,2914,2880,2750,2729,2393,2239,2100,2007,1957
1939,1867,1797,1676,1638,1591,1556,1478,1433,1378,1358,1348,1288,1258,1242,
1235,1198,1162,1123,1090,1061,982,973,953,914,898,845,811,775,751,670,573,
544,523,479,463cm-l.
1H NMR(CDCl3-d6):δ7.24(4H,t),6.92(2H,d),3.95(4H,t),3.86(4H,s),3.79(4H,
t),2.82(12H,t)；
13C NMR(CDCl3-d6)δ155.83,130.95,128.80,123.82,71.31,67.44,65.87,16.28；
Elemental analysis：Molecular formula C22H30O4
Theoretical value：C,73.71；H,8.44；O,17.85.
Measured value：C,73.39；H,8.47；O,18.14.
Above structure appraising datum confirms that the substance that this step obtains is strictly (the 2- (2,6- dimethyl phenoxy) of 1,2- bis-
Ethyoxyl) ethane.
Embodiment 2
Under 20 DEG C of stirrings of temperature, by 1.85g 2,10ml ethyl alcohol-is added in 6- xylenols and 1g triethylene-glycols
In water mixed solution, potassium hydroxide 0.72g is added to it, is warming up to 82 DEG C, after reacting 60h, 3 are extracted using 10ml dichloromethane
It is secondary, obtain dichloromethane extract liquor.
Dichloromethane extract liquor is washed 2 times using 5ml 1M sodium hydroxide solutions, then washes 1 with saturated nacl aqueous solution (20 DEG C)
Secondary, anhydrous magnesium sulfate drying, normal pressure is evaporated dichloromethane, obtains yellow oily liquid；
5ml ether is added to above-mentioned yellow oily liquid, is warming up to 35 DEG C, filters off insoluble matter, is cooled to -15 DEG C, cooling
48h, filtering solution obtain 1.57g white powdery solids 1, and 2- bis- (2- (2,6- dimethyl phenoxy) ethyoxyl) ethane is received
Rate 81.77%, purity 98.23%, 67 DEG C~68 DEG C of fusing point.
Embodiment 3
Under 20 DEG C of stirrings of temperature, by 1.80g 2,10ml ethyl alcohol-is added in 6- xylenols and 1g triethylene-glycols
In water mixed solution, potassium hydroxide 0.72g is added to it, is warming up to 82 DEG C, after reacting 60h, 2 are extracted using 10ml dichloromethane
It is secondary, obtain dichloromethane extract liquor.
Dichloromethane extract liquor is washed 2 times using 5ml 1M sodium hydroxide solutions, then washes 1 with saturated nacl aqueous solution (20 DEG C)
Secondary, anhydrous magnesium sulfate drying, normal pressure is evaporated dichloromethane, obtains yellow oily liquid；
5ml ether is added to above-mentioned yellow oily liquid, is warming up to 35 DEG C, filters off insoluble matter, is cooled to -15 DEG C, cooling
48h, filtering solution obtain 1.45g white powdery solids 1, and 2- bis- (2- (2,6- dimethyl phenoxy) ethyoxyl) ethane is received
Rate 75.52%, purity 98.27%, 67 DEG C~68 DEG C of fusing point.
Embodiment 4
Under 20 DEG C of stirrings of temperature, by 1.80g 2,10ml ethyl alcohol-is added in 6- xylenols and 1g triethylene-glycols
In water mixed solution, potassium hydroxide 0.72g is added to it, is warming up to 82 DEG C, after reacting 60h, 3 are extracted using 10ml dichloromethane
It is secondary, obtain dichloromethane extract liquor.
Dichloromethane extract liquor is washed 1 time using 5ml 1M sodium hydroxide solutions, and anhydrous magnesium sulfate drying, normal pressure is evaporated dichloro
Methane obtains yellow oily liquid；5ml ether is added to yellow oily liquid, is warming up to 35 DEG C, filters off insoluble matter, be cooled to-
15 DEG C, cool down 48h, and filtering solution obtains 1.60g white powdery solids 1, (2- (2, the 6- dimethyl phenoxy) ethoxies of 2- bis-
Base) ethane, yield 83.33%, purity 95.19%, 67 DEG C~68 DEG C of fusing point.
Embodiment 5
Under 20 DEG C of stirrings of temperature, by 1.80g 2,10ml ethyl alcohol-is added in 6- xylenols and 1g triethylene-glycols
In water mixed solution, potassium hydroxide 0.72g is added to it, is warming up to 82 DEG C, after reacting 60h, 3 are extracted using 10ml dichloromethane
It is secondary, obtain dichloromethane extract liquor.
Dichloromethane extract liquor is washed 2 times using 5ml 1M sodium hydroxide solutions, then washes 1 with saturated nacl aqueous solution (20 DEG C)
Secondary, anhydrous magnesium sulfate drying, normal pressure is evaporated dichloromethane, obtains yellow oily liquid；
5ml ether is added to above-mentioned yellow oily liquid, is warming up to 35 DEG C, filters off insoluble matter, is cooled to -10 DEG C, cooling
48h, filtering solution obtain 1.58g white powdery solids 1, and 2- bis- (2- (2,6- dimethyl phenoxy) ethyoxyl) ethane is received
Rate 82.29%, purity 95.29%, 67 DEG C~68 DEG C of fusing point.
Claims (2)
1. one kind 1, the preparation method of 2- bis- (2- (2,6- dimethyl phenoxy) ethyoxyl) ethane, 1,2- bis- (2- (2,6- diformazans
Phenoxyl) ethyoxyl) ethane structural formula such as shown in (I)：
With 2,6- xylenols and triethylene-glycol for raw material, such as (II) and (III) is shown respectively for structural formula, including with
Lower step：
(1) under 20 DEG C~25 DEG C stirrings of temperature, 2,6- xylenols and triethylene-glycol is added to alcohol-water and mixed
In solution, then potassium hydroxide is added thereto, is 80 DEG C~85 DEG C reaction 40h~70h in temperature, reaction solution is extracted with dichloromethane
It takes 2~3 times, obtains dichloromethane extract liquor；Wherein, the mass ratio of triethylene-glycol, 2,6- xylenols, potassium hydroxide
It is 1:1.79~2.00:0.72~1, the volume ratio of second alcohol and water is 4:6~6:4；
(2) above-mentioned dichloromethane extract liquor is washed 2~3 times using 1M sodium hydroxide solutions, then 1 is washed with saturated nacl aqueous solution~
2 times, after being dried with anhydrous magnesium sulfate, normal pressure is evaporated dichloromethane, obtains yellow oily liquid；Second is added to yellow oily liquid
Ether is warming up to 30 DEG C~35 DEG C, filters off insoluble matter and is cooled to -15 DEG C~-10 DEG C, and cool down for 24 hours~48h, and filtering solution obtains white
Color pulverulent solids 1,2- bis- (2- (2,6- dimethyl phenoxy) ethyoxyl) ethane.
2. the preparation method of 1,2- bis- (2- (2,6- dimethyl phenoxy) ethyoxyl) ethane according to claim 1, packet
Include following steps：
Under (1) 20 DEG C of stirring, 2,6- xylenols and triethylene-glycol are added in alcohol-water mixed solution, then to
Potassium hydroxide is wherein added, is 82 DEG C of reaction 60h in temperature, reaction solution is extracted 3 times with dichloromethane, obtains dichloromethane extraction
Liquid, wherein triethylene-glycol, 2,6- xylenols, potassium hydroxide mass ratio be 1:1.80:0.72；
(2) above-mentioned dichloromethane extract liquor is washed 2 times using 1M sodium hydroxide solutions, then is washed 1 time with saturated nacl aqueous solution, used
After anhydrous magnesium sulfate drying, normal pressure is evaporated dichloromethane, obtains yellow oily liquid, and ether is added to yellow oily liquid, rises
Temperature filters off insoluble matter to 35 DEG C, is cooled to -15 DEG C, and cool down 48h, and filtering solution obtains white powdery solids 1, bis- (2- of 2-
(2,6- dimethyl phenoxies) ethyoxyl) ethane.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115894184A (en) * | 2022-11-15 | 2023-04-04 | 黎明化工研究设计院有限责任公司 | Method for preparing di (2, 6-dimethoxyphenyl) triethylene glycol |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010038737A1 (en) * | 2008-10-02 | 2010-04-08 | 日産化学工業株式会社 | Method for producing 6,6'-(alkylenedioxy)di-2-naphthoic acid diester compound |
| CN108002988A (en) * | 2017-11-24 | 2018-05-08 | 西安近代化学研究所 | 1,2- bis-（2-（2,6- dimethoxy phenoxy groups）Ethyoxyl）The preparation method of ethane |
-
2018
- 2018-06-05 CN CN201810566670.8A patent/CN108558613A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010038737A1 (en) * | 2008-10-02 | 2010-04-08 | 日産化学工業株式会社 | Method for producing 6,6'-(alkylenedioxy)di-2-naphthoic acid diester compound |
| CN108002988A (en) * | 2017-11-24 | 2018-05-08 | 西安近代化学研究所 | 1,2- bis-（2-（2,6- dimethoxy phenoxy groups）Ethyoxyl）The preparation method of ethane |
Non-Patent Citations (5)
| Title |
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| O.N.CHUPAKHIN: "New 1,2,4-triazine-containing podands synthesis and properties", 《RUSSIAN CHEMICAL BULLETIN, INTERNATIONAL EDITION》 * |
| 信颖等: "《有机化学 供中药学、药学、制药工程等专业用 新世纪第4版》", 31 January 2017 * |
| 荣国斌等: "《高等有机化学》", 31 October 2007 * |
| 邢其毅等: "《基础有机化学 上》", 31 December 1980 * |
| 陈碧芬: "《应用有机化学》", 31 May 2012 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115894184A (en) * | 2022-11-15 | 2023-04-04 | 黎明化工研究设计院有限责任公司 | Method for preparing di (2, 6-dimethoxyphenyl) triethylene glycol |
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Application publication date: 20180921 |