CN107935822A - 1,2 two（2‑（4 methoxyphenoxies）Ethyoxyl）The preparation method of ethane - Google Patents
1,2 two（2‑（4 methoxyphenoxies）Ethyoxyl）The preparation method of ethane Download PDFInfo
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- CN107935822A CN107935822A CN201711190313.8A CN201711190313A CN107935822A CN 107935822 A CN107935822 A CN 107935822A CN 201711190313 A CN201711190313 A CN 201711190313A CN 107935822 A CN107935822 A CN 107935822A
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- ethane
- ethyoxyl
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N COc(cc1)ccc1O Chemical compound COc(cc1)ccc1O NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 0 COc(cc1)ccc1OCCOCCOCCOc1ccc(*)cc1 Chemical compound COc(cc1)ccc1OCCOCCOCCOc1ccc(*)cc1 0.000 description 1
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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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Abstract
The invention discloses a kind of preparation method of 1,2 two (2 (4 methoxyphenoxy) ethyoxyl) ethane, in order to solve to overcome it is existing in the prior art using reactant not environmentally, low yield the problems such as.The present invention comprises the following steps using 4 metoxyphenols and triethylene-glycol as raw material：(1) 20 DEG C of stirring, 4 metoxyphenols and triethylene-glycol are added in acetonitrile, add dicyclohexylcarbodiimide, 85 DEG C of reaction 24h, are evaporated acetonitrile, obtain troubled liquor 1；(2) 1 add methylene chloride, and filtering, 1M caustic washings 3 times, saturated sodium-chloride is washed 2 times, and anhydrous magnesium sulfate drying, is evaporated dichloromethane, obtains yellow powdery solid 2；(3) 2 add diethyl ether, and heat up 35 DEG C, filter off insoluble matter, cool down 15 DEG C, and cool down 4h, and filtering, obtains white powdery solids 1,2 two (2 (4 methoxyphenoxy) ethyoxyl) ethane.Present invention is mainly used for the preparation of 1,2 two (2 (4 methoxyphenoxy) ethyoxyl) ethane.
Description
Technical field
The present invention relates to the synthetic method of one kind 1,2- bis- (2- (4- methoxyphenoxies) ethyoxyl) ethane.Belong to organic conjunction
Into.
Background technology
The ability that solid propellant keeps its chemical property not occur to exceed permission excursion within storage period is referred to as
Chemical stability.The compounds containing itrate group such as common nitrocellulose, nitroglycerine are biradical and modified double base propellants
In main energetic component, its nitric acid ester bond is easy to be broken (150.5~167.2kJ/mol of bond energy), produces thermal decomposition, release big
The gas and heat of amount, the nitrogen oxides discharged, and accelerate nitrate to decompose, self-catalyzed reaction is formed, causes propellant power
Performance, combustibility decline are learned, or even the serious accidents such as burning, explosion occur.Therefore, the propellant containing itrate group component
It can also decompose under storage requirement, cause propellant stability to decline.In order to delay propellant to thermally decompose, improve stable
Property, propellant containing nitrate esters adds stabilization agent, for absorbing acid, nitrogen oxides and its free radical of nitrate decomposition generation,
So as to suppress or delay the Autocatalytic decomposition of nitrate to react.
At present, common chemical stabilization agent has anil and phenol analog derivative etc., its representation compound is N, and N '-
Dimethyl-N, N '-acardite (C2), resorcinol (Res), diphenylamines (DPA), 2- nitrodiphenylamines (2-NDPA), N- methyl
Paranitroanilinum (MNA) etc..With the development of nitrate esters high-energy propellant, the country proposes that developing tactics type high-energy solid promotes
The requirement of agent.Found in the development process of tactics type high-energy solid propellant, have been used for existing high-energy solid propellant (such as
NEPE types propellant) stabilization agent such as N- methyl paranitroanilines (MNA) reactivity it is stronger, it can be with tactics type high-energy solid
The curing agent (isocyanates) that propellant uses reacts, so as to limit the application of MNA.It is, thus, sought for one kind was both
It can meet the stability of high-energy solid propellant, no partial crystallization transport phenomena occurs, and the not new stabilization agent with curing agent reaction.
1999, it was raw material that Pursiainen etc., which selects 4- metoxyphenols and 1,2- (dichloroethanes base) ethane, hydrogen-oxygen
Change and synthesized compound 1,2- bis- (2- (4- methoxyphenoxies) ethyoxyl) ethane under potassium catalysis, and be applied to be visited
Rope. (Markku L,Kirsi R,Jouni P.Synthesis of podands bearing aromatic end
groups and complex formation with tropylium tetra-uoroborate in 1,2-
dichloroethane,Journal of Physical Organic,1999, 12:557-563.).Pursiainen methods
Synthetic route is as follows：
Pursiainen has used highly basic sodium hydroxide and chloro-containing reagent 1 in article, and 2- (dichloroethanes base) ethane is right
Environment causes certain pollution, and the characterize data that Pursiainen is provided in article has the problem of larger, wherein 1H NMR
H number of middle display is 30, and the number of actual this compound H is 24, and the yield of Pursiainen methods is 96%.
The content of the invention
The technical problems to be solved by the invention are to overcome the deficiencies in the prior art, there is provided a kind of yield raising,
1,2- bis- (2- (4- methoxyphenoxies) ethyoxyl) ethane synthetic method of reaction method environmental protection.
The synthetic route of the present invention is using 4- metoxyphenols and triethylene-glycol as raw material, with dicyclohexylcarbodiimide
For catalyst, acetonitrile is solvent, and etherification reaction is carried out with triethylene-glycol, by post-processing, obtains product 1, bis- (2- of 2-
(4- methoxyphenoxies) ethyoxyl) ethane.
The synthetic method of 1,2- bis- (2- (4- methoxyphenoxies) ethyoxyl) ethane of the present invention, 1,2- bis- (2- (4- first
Epoxide phenoxy group) ethyoxyl) ethane structural formula such as shown in (I)：
Using 4- metoxyphenols and triethylene-glycol as raw material, such as (II) and (III) is shown respectively for its structural formula, including
Following steps：
(1) under 20 DEG C~30 DEG C stirrings of temperature, 4- metoxyphenols and triethylene-glycol are added in acetonitrile, then
Dicyclohexylcarbodiimide (DCC) is added thereto, is 85 DEG C~95 DEG C reaction 16h~30h in temperature, is crossed filter solid, decompression
Acetonitrile is distilled out, obtains crocus troubled liquor 1；Wherein, triethylene-glycol, 4- metoxyphenols, dicyclohexyl carbon two are sub-
The molar ratio of amine is 1:2~2.3:2.2~2.5；
(2) dichloromethane is added into above-mentioned crocus troubled liquor 1, insoluble matter is filtered off, uses 1M sodium hydroxide solutions
Wash 2~4 times, then washed 2~3 times, after being dried with anhydrous magnesium sulfate with saturated nacl aqueous solution, normal pressure is evaporated dichloromethane, obtains
Pale yellow powder shape solid 2；
(3) ether is added to above-mentioned pale yellow powder shape solid 2, is warming up to 30 DEG C~35 DEG C, filter off insoluble matter, cooling
To -15 DEG C~-10 DEG C, cool down 3h~5h, and filtering solution, obtains white powdery solids 1, (2- (the 4- methoxybenzene oxygen of 2- bis-
Base) ethyoxyl) ethane.
The synthetic method of currently preferred 1,2- bis- (2- (4- methoxyphenoxies) ethyoxyl) ethane, including following step
Suddenly：
Under (1) 20 DEG C of stirring, 4- metoxyphenols and triethylene-glycol are added in acetonitrile, then add two thereto
Carbodicyclo hexylimide, 85 DEG C of reaction 24h, is evaporated under reduced pressure out acetonitrile, obtains crocus troubled liquor 1；Wherein, two three second two of contracting
Alcohol, 4- metoxyphenols, the molar ratio of dicyclohexylcarbodiimide are 1:2.2:2.4；
(2) dichloromethane is added into above-mentioned crocus troubled liquor 1, insoluble matter is filtered off, uses 1M sodium hydroxide solutions
Wash 3 times, then washed 2 times, after being dried with anhydrous magnesium sulfate with saturated nacl aqueous solution, normal pressure is evaporated dichloromethane, obtains yellow oil
Shape liquid 2；
(3) ether is added to above-mentioned yellow oily liquid 2, is warming up to 35 DEG C, filter off insoluble matter, be cooled to -15 DEG C, cooling
4h, filtering solution, obtains white powdery solids 1,2- bis- (2- (4- methoxyphenoxies) ethyoxyl) ethane.
Advantages of the present invention：
The present invention replaces dichloroethanes base in documents using triethylene-glycol and dicyclohexylcarbodiimide) ethane
And sodium hydroxide, avoid using chloro-containing reagent and strong basicity potassium hydroxide；The yield of the present invention is 98%, the yield of documents
For 96%, reaction yield is improved.
Embodiment
The present invention is described in further details with reference to embodiment.
Embodiment 1
Under 20 DEG C of stirrings of temperature, by 13.66g (110mmol) 4- metoxyphenols and three second of contracting of 7.51g (50mmol) two
Glycol is added in 100ml acetonitriles, and dicyclohexylcarbodiimide 24.72g (120mmol) is added to it, is warming up to 85 DEG C, reaction
After 24h, acetonitrile is evaporated under reduced pressure out, obtains crocus troubled liquor 1；
Extracted 3 times with 50ml dichloromethane into above-mentioned crocus troubled liquor 1, use 50ml 1M sodium hydroxide solutions
Wash 3 times, then washed 2 times with 50ml saturated nacl aqueous solutions (20 DEG C), anhydrous magnesium sulfate drying, normal pressure is evaporated dichloromethane, obtains
Yellow oily liquid；
25ml 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
3h, filtering solution, obtains 17.86g white powdery solids 1,2- bis- (2- (4- methoxyphenoxies) ethyoxyl) ethane, yield
98.02%, purity 98.27%, 67~68 DEG C of fusing point.
Structural Identification：
IR(KBr)ν:3444,3057,3014,2959,2931,2902,2871,2838,2786,2700,2590,2545,
2474,2345,2125,2050,1986,1905,1866,1740,1626,1509,1453,1385,1332,1287,1250,
1229,1189,1132,1116,1072,1055,1031,948,927,883,821,731,593,522,449,423cm-l.
1H NMR(CDCl3-d6):δ6.85(4H,t),6.80(4H,d),4.07(4H,t),3.83(4H,s),3.75(6H,
t), 3.74(4H,t)；
13C NMR(CDCl3-d6)δ153.96,152.98,115.69,114.61,70.87,69.94,68.15,
55.70；.
Said structure appraising datum confirms that the material that this step obtains is strictly (2- (4- methoxyphenoxies) second of 1,2- bis-
Epoxide) ethane.
Embodiment 2
Under 20 DEG C of stirrings of temperature, by 13.66g (110mmol) 4- metoxyphenols and three second of contracting of 7.51g (50mmol) two
Glycol is added in 100ml acetonitriles, and dicyclohexylcarbodiimide 24.72g (120mmol) is added to it, is warming up to 85 DEG C, reaction
After 16h, acetonitrile is evaporated under reduced pressure out, obtains crocus troubled liquor 1；
Extracted 3 times with 50ml dichloromethane into above-mentioned crocus troubled liquor 1, use 50ml 1M sodium hydroxide solutions
Wash 3 times, then washed 2 times with 50ml saturated nacl aqueous solutions (20 DEG C), anhydrous magnesium sulfate drying, normal pressure is evaporated dichloromethane, obtains
Yellow oily liquid；
25ml 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
3h, filtering solution, obtains 17.02g white powdery solids 1,2- bis- (2- (4- methoxyphenoxies) ethyoxyl) ethane, yield
93.41%, purity 98.16%.
Embodiment 3
Under 20 DEG C of stirrings of temperature, by 13.66g (110mmol) 4- metoxyphenols and three second of contracting of 7.51g (50mmol) two
Glycol is added in 100ml acetonitriles, and dicyclohexylcarbodiimide 24.72g (120mmol) is added to it, is warming up to 85 DEG C, reaction
After 30h, acetonitrile is evaporated under reduced pressure out, obtains crocus troubled liquor 1；
Extracted 3 times with 50ml dichloromethane into above-mentioned crocus troubled liquor 1, use 50ml 1M sodium hydroxide solutions
Wash 2 times, then washed 2 times with 50ml saturated nacl aqueous solutions (20 DEG C), anhydrous magnesium sulfate drying, normal pressure is evaporated dichloromethane, obtains
Yellow oily liquid；
25ml 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
3h, filtering solution, obtains 17.94g white powdery solids 1,2- bis- (2- (4- methoxyphenoxies) ethyoxyl) ethane, yield
98.46%, purity 97.33%.
Embodiment 4
Under 20 DEG C of stirrings of temperature, by 13.66g (110mmol) 4- metoxyphenols and three second of contracting of 7.51g (50mmol) two
Glycol is added in 100ml acetonitriles, and dicyclohexylcarbodiimide 24.72g (120mmol) is added to it, is warming up to 65 DEG C, reaction
After 30h, acetonitrile is evaporated under reduced pressure out, obtains crocus troubled liquor 1；
Extracted 3 times with 50ml dichloromethane into above-mentioned crocus troubled liquor 1, use 50ml 1M sodium hydroxide solutions
Wash 3 times, then washed 2 times with 50ml saturated nacl aqueous solutions (20 DEG C), anhydrous magnesium sulfate drying, normal pressure is evaporated dichloromethane, obtains
Yellow oily liquid；
25ml 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
3h, filtering solution, obtains 17.35g white powdery solids 1,2- bis- (2- (4- methoxyphenoxies) ethyoxyl) ethane, yield
95.22%, purity 98.17%.
Embodiment 5
Under 20 DEG C of stirrings of temperature, by 14.28g (115mmol) 4- metoxyphenols and three second of contracting of 7.51g (50mmol) two
Glycol is added in 100ml acetonitriles, and dicyclohexylcarbodiimide 24.72g (120mmol) is added to it, is warming up to 85 DEG C, reaction
After 30h, acetonitrile is evaporated under reduced pressure out, obtains crocus troubled liquor 1；
Extracted 3 times with 50ml dichloromethane into above-mentioned crocus troubled liquor 1, use 50ml 1M sodium hydroxide solutions
Wash 3 times, then washed 2 times with 50ml saturated nacl aqueous solutions (20 DEG C), anhydrous magnesium sulfate drying, normal pressure is evaporated dichloromethane, obtains
Yellow oily liquid；
25ml 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
3h, filtering solution, obtains 17.37g white powdery solids 1,2- bis- (2- (4- methoxyphenoxies) ethyoxyl) ethane, yield
95.33%, purity 98.30%.
Claims (2)
1. one kind 1, the preparation method of 2- bis- (2- (4- methoxyphenoxies) ethyoxyl) ethane, 1,2- bis- (2- (4- methoxybenzenes
Epoxide) ethyoxyl) ethane structural formula such as shown in (I)：
Using 4- metoxyphenols and triethylene-glycol as raw material, its structural formula is respectively as shown in (II) and (III), including following
Step：
(1) under the stirring of 20 DEG C~30 DEG C of temperature, 4- metoxyphenols and triethylene-glycol are added in acetonitrile, then to its
Middle addition dicyclohexylcarbodiimide, is 85 DEG C~95 DEG C reaction 16h~30h in temperature, crosses filter solid, be evaporated under reduced pressure out second
Nitrile, obtains crocus troubled liquor 1；Wherein, triethylene-glycol, 4- metoxyphenols, mole of dicyclohexylcarbodiimide
Than for 1:2~2.3:2.2~2.5；
(2) add dichloromethane into above-mentioned crocus troubled liquor 1, filter off insoluble matter, 2 are washed using 1M sodium hydroxide solutions~
4 times, then washed 2~3 times, after being dried with anhydrous magnesium sulfate with saturated nacl aqueous solution, normal pressure is evaporated dichloromethane, obtains faint yellow
Pulverulent solids 2；
(3) ether is added to above-mentioned pale yellow powder shape solid 2, is warming up to 30 DEG C~35 DEG C, filtered off insoluble matter, be cooled to -15
DEG C~-10 DEG C, cool down 3h~5h, and filtering solution, obtains white powdery solids 1, (2- (4- methoxyphenoxies) ethoxies of 2- bis-
Base) ethane.
2. the preparation method of 1,2- bis- (2- (4- methoxyphenoxies) ethyoxyl) ethane according to claim 1, including
Following steps：
Under (1) 20 DEG C of stirring, 4- metoxyphenols and triethylene-glycol are added in acetonitrile, then add two hexamethylenes thereto
Base carbodiimide, 85 DEG C of reaction 24h, is evaporated under reduced pressure out acetonitrile, obtains crocus troubled liquor 1；Wherein, triethylene-glycol,
4- metoxyphenols, the molar ratio of dicyclohexylcarbodiimide are 1:2.2:2.4；
(2) dichloromethane is added into above-mentioned crocus troubled liquor 1, insoluble matter is filtered off, 3 is washed using 1M sodium hydroxide solutions
It is secondary, then washed 2 times, after being dried with anhydrous magnesium sulfate with saturated nacl aqueous solution, normal pressure is evaporated dichloromethane, obtains yellow oily liquid
Body 2；
(3) ether is added to above-mentioned yellow oily liquid 2, is warming up to 35 DEG C, filter off insoluble matter, be cooled to -15 DEG C, cool down 4h,
Filtering solution, obtains white powdery solids 1,2- bis- (2- (4- methoxyphenoxies) ethyoxyl) ethane.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108558614A (en) * | 2018-06-05 | 2018-09-21 | 西安近代化学研究所 | 1,2- bis-（2-（2,6- dimethyl phenoxies）Ethyoxyl）The preparation method of ethane |
| CN108558616A (en) * | 2018-06-05 | 2018-09-21 | 西安近代化学研究所 | One kind 1,2- bis-（2-（4- methylphenoxies）Ethyoxyl）The preparation method of ethane |
| CN108558617A (en) * | 2018-06-05 | 2018-09-21 | 西安近代化学研究所 | 1,2- bis-（2-（4- methylphenoxies）Ethyoxyl）The preparation method of ethane |
| CN108821954A (en) * | 2018-06-05 | 2018-11-16 | 西安近代化学研究所 | 1,2- bis-（2-（4- methylphenoxy）Ethyoxyl）The synthetic method of ethane |
| CN108863731A (en) * | 2018-06-05 | 2018-11-23 | 西安近代化学研究所 | One kind 1,2- bis-（2-（4- methylphenoxy）Ethyoxyl）The synthetic method of ethane |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108558614A (en) * | 2018-06-05 | 2018-09-21 | 西安近代化学研究所 | 1,2- bis-（2-（2,6- dimethyl phenoxies）Ethyoxyl）The preparation method of ethane |
| CN108558616A (en) * | 2018-06-05 | 2018-09-21 | 西安近代化学研究所 | One kind 1,2- bis-（2-（4- methylphenoxies）Ethyoxyl）The preparation method of ethane |
| CN108558617A (en) * | 2018-06-05 | 2018-09-21 | 西安近代化学研究所 | 1,2- bis-（2-（4- methylphenoxies）Ethyoxyl）The preparation method of ethane |
| CN108821954A (en) * | 2018-06-05 | 2018-11-16 | 西安近代化学研究所 | 1,2- bis-（2-（4- methylphenoxy）Ethyoxyl）The synthetic method of ethane |
| CN108863731A (en) * | 2018-06-05 | 2018-11-23 | 西安近代化学研究所 | One kind 1,2- bis-（2-（4- methylphenoxy）Ethyoxyl）The synthetic method of ethane |
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