CN1709848A - Method for preparing substituted dibenzyl ether - Google Patents
Method for preparing substituted dibenzyl ether Download PDFInfo
- Publication number
- CN1709848A CN1709848A CN 200510040614 CN200510040614A CN1709848A CN 1709848 A CN1709848 A CN 1709848A CN 200510040614 CN200510040614 CN 200510040614 CN 200510040614 A CN200510040614 A CN 200510040614A CN 1709848 A CN1709848 A CN 1709848A
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- Prior art keywords
- substituted
- dibenzyl ether
- reaction
- bromine
- chlorine
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- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 39
- -1 benzyl halide Chemical class 0.000 claims abstract description 25
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910001507 metal halide Inorganic materials 0.000 claims abstract description 10
- 150000005309 metal halides Chemical class 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 5
- 238000000926 separation method Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- ZIHQUWYJSTVYAT-UHFFFAOYSA-N [NH-][N+]([O-])=O Chemical group [NH-][N+]([O-])=O ZIHQUWYJSTVYAT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 229910052792 caesium Inorganic materials 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 15
- 230000007062 hydrolysis Effects 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000002994 raw material Substances 0.000 description 8
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 7
- 229940073608 benzyl chloride Drugs 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000019445 benzyl alcohol Nutrition 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000003672 processing method Methods 0.000 description 3
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 2
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000001743 benzylic group Chemical group 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229920001220 nitrocellulos Polymers 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000003408 phase transfer catalysis Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-UHFFFAOYSA-N 0.000 description 1
- IRSVDHPYXFLLDS-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1Cl IRSVDHPYXFLLDS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- LFQULJPVXNYWAG-UHFFFAOYSA-N sodium;phenylmethanolate Chemical compound [Na]OCC1=CC=CC=C1 LFQULJPVXNYWAG-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing substituted dibenzyl ether. The method adopts substituted benzyl halide to react with water, uses metal halide as a catalyst, directly reacts to generate substituted dibenzyl ether, and then is separated and purified. The method does not use alkaline substances, reduces resource consumption and waste discharge, and the generated halogen acid can be recycled after separation and concentration, and has the characteristics of low cost, less resource consumption, environmental protection, simplicity and practicability.
Description
Technical field
The present invention relates to the preparation method of substituted dibenzyl ether, wherein adopt substituted benzyl halogen and water reaction, particularly metallic halid catalyst, generate the method for substituted dibenzyl ether.
Background technology
Dibenzyl ether and derivative thereof are used for nitrocellulose and functional paint as softening agent, are used as additive at rubber and textile industry, are used as the solvent and the bottom note of spices in fine chemicals.The dibenzyl ether derivative that has functional group can be used for organic synthesis, prepares the multiple bioactive compound that has.These are well known to a person skilled in the art.For example dibenzyl ether itself has special aroma such as light earth fragrant or have the mushroom fragrance of rose sample bottom note, can make an addition to makeup, food and drink etc., and is safe and reliable.
The preparation method of multiple dibenzyl ether extensively is seen in disclosed document.Usually produce dibenzyl ether with Williamson system ether method by benzyloxy sodium and benzyl chloride reaction.Other discloses phase transfer catalysis condition as JP7535123 and SU1035020, the prepared in reaction dibenzyl ether of alkaline aqueous solution and benzyl chloride; Two moles of benzyl alcohol dehydration system ethers; The reaction of benzyl halide and benzyl alcohol generates dibenzyl ether etc. under the special conditions.Produce the pure by-product dibenzyl ether except Williamson legal system dibenzyl ether and benzyl chloride basic hydrolysis, above-mentioned other method all is not put to industrial application.Analyze reason, though phase transfer catalysis process conveniently reclaims and recycle alkali aqueous solution, the phase-transfer catalyst cost is higher and recycle still unresolved; Methods such as strong acid catalyzed benzyl halide of Lewis and benzyl alcohol reaction, benzyl alcohol dehydration and microwave reactor application are in conceptual phase.Benzyl chloride basic hydrolysis by-product dibenzyl ether method particularly, the reaction that benzyl halide and water are only arranged is a reversible, those skilled in the art is known to this.Prepare benzyl alcohol technology as US5670029, US5728897 and the disclosed benzyl chloride hydrolysis of US5750801, its remarkable advantage is a single step reaction, and is solvent-free, alkali-free, and yield height, benzyl chloride recycle and reclaim hydrogenchloride.The a small amount of dibenzyl ether of this technology by-product, and a kind of feature of above-mentioned patent disclosure is than the low-conversion condition by product dibenzyl ether seldom to be generated, and other technology is lacked competitiveness economically.And above-mentioned processing method does not all relate to the preparation method of relevant substituted dibenzyl ether, and their common limitation is to consume a large amount of alkali, or needs special reagent and facility.Wish to develop direct, the easy and eco-friendly processing method of producing substituted dibenzyl ether by substituted benzyl halogen.
Summary of the invention
The purpose of this invention is to provide a kind of method that adopts substituted benzyl halogen direct hydrolysis to produce substituted dibenzyl ether.
Technical scheme of the present invention is can impel reaction to generate ether according to add metal halide in the reaction system of substituted benzyl halogen and water, therefore, select conditions such as proper metal halogenide catalysis and temperature, pressure, time, the main substituted dibenzyl ether that generates of reaction.
The objective of the invention is to realize by following measures:
A kind of method of producing substituted dibenzyl ether, this method are to adopt substituted benzyl halogen and water reaction, make catalyzer with metal halide, and direct reaction promptly generates substituted dibenzyl ether, and separation, purifying get final product;
Wherein, substituted dibenzyl ether is suc as formula shown in (I), and substituted benzyl halogen is suc as formula shown in (II):
Here, Ar
1And Ar
2The expression substituted aryl, Ar
1And Ar
2Can be identical or different, Ar
1And Ar
2By formula (II) definition, k represents an integer of 0～5, and l represents an integer of 0～5, and k+l is an integer of 0～5, X
1Expression chlorine, bromine or iodine, X
2Expression fluorine, chlorine, bromine or iodine, when k 〉=2, X
2Can be identical or different, the substituting group that R represents is trifluoromethyl, itrile group, nitro, amide group, alkoxyl group or aryloxy, when l 〉=2, R can be identical or different.
Described method, wherein the general formula of metal halide is MX
3 m, wherein, M is a metal, X
3Be chlorine, bromine or iodine, m is 1,2 or 3.
Described method, wherein metal halide MX
3 mM be Li, Na, K, Rb or Cs, m is 1 or 2, X
3Be bromine or iodine, X further
3Be iodine.
Described method, the wherein Ar in the substituted dibenzyl ether formula (I)
1And Ar
2Identical.
Described method, the wherein X of substituted benzyl halogen (II)
1Be chlorine or bromine, k is 1,2 or 3, and l is 1 or 2.
Described method, the wherein X of substituted benzyl halogen (II)
1Be chlorine, X
2Be chlorine or bromine.
Substituted benzyl halogen of the present invention (II) can adopt Industrial products.Substituted benzyl halogen (II) direct hydrolysis under catalyst action is carried out, and adopts substituted benzyl halogen to mix the water yield of preferred 10～150 times (moles), the water yield of preferred especially 20～100 times (moles) with the water of 5～200 times (moles).
Above-mentioned reaction mixture adds metal halide MX
3 m, MX
3 mAmount is 0.1～20% (mole) of substituted benzyl halogen amount, preferred 0.5～10% (mole), preferred especially 1～5% (mole).
Said mixture is reacting by heating in reactor, 40～320 ℃ of temperature ranges, preferred 70～240 ℃, preferred especially 90～200 ℃.
The pressure of reaction system is in liquid phase for keeping reaction system at least, and reaction pressure is 0～22.5 MPa, is preferably 0～10 MPa, is preferably 0～3 MPa especially.
Adopting control of whipping appts and other supplementary unit and adjustment two-phase admixture and liquid flowing state is well known to a person skilled in the art.
According to the different technology conditions and the parameter of above-mentioned selection, the reaction times was from dozens of minutes to tens hour, common 0.5～48 hour, preferred 1～24 hour, preferred especially 2～12 hours.
The gained reaction product can be separated and purifying with several different methods, comprises extraction, chromatography or vacuum distilling etc., and these are known in those skilled in the art.
The structure of different substituted benzyl halogen (II) and character have difference in various degree, therefore response feature can change, usually the electron-withdrawing substituent on the phenyl ring can make the replacement of monochloromethyl carry out easily, and the water solubility of product (I) is very little, help the reaction comparatively fast carry out higher with productive rate, by product ether is less.These are known in those skilled in the art.
Beneficial effect of the present invention:
The distinguishing feature of method of the present invention is not use alkaline matter, has reduced resource consumption and waste discharge, and the haloid acid of generation is through separating and concentrating, and renewable use has embodied Atom economy and eco-friendly process characteristic.
The substituted dibenzyl ether of multiple structure and derivative thereof are used for nitrocellulose and functional paint as softening agent, are used as additive at rubber and textile industry, are used as the solvent and the bottom note of spices in fine chemicals.The dibenzyl ether derivative that has functional group can be used for organic synthesis, prepares the multiple bioactive compound that has.
According to processing method of the present invention, the yield of products therefrom can surpass 90%, and unconverted (I) reclaims, and haloid acid can reclaim and concentrate.
Embodiment
According to following embodiment, the present invention may be better understood.Yet, those skilled in the art will readily understand that the described concrete material proportion of embodiment, processing condition and result only are used to illustrate the present invention, and should also can not limit the present invention described in detail in claims.
Embodiment 1: the benzyl chloride hydrolysis prepares dibenzyl ether
Get chlorobenzyl chloride 2.53g, KI0.10g, water 18mL adds triangular flask, is warmed up to 115 ℃ rapidly, begin to reflux, vigorous stirring, back flow reaction 48 hours, reaction pressure are 5 MPas, TLC detects (ethanol-normal hexane, 1: 5), forms no longer to change.Cool to about 60 ℃, add toluene 20mL extraction, temperature is near near room temperature, separatory.Water reclaims hydrogen halide with ethyl acetate (10mL * 2) extraction; Merge organic phase, anhydrous sodium sulfate drying, fully evaporate to dryness (if the little residue water gaging can add 10～20mL toluene, evaporate to dryness again).Cross silicagel column (method and the parameter of crossing silicagel column are contents known to a person of ordinary skill in the art), get colorless oil product 1.25g, reclaim raw material 0.6g.
Embodiment 2: the bromotoluene hydrolysis prepares dibenzyl ether
The method of embodiment 1.But raw material bromotoluene (3.42g) reacted 24 hours.Get colorless oil product 1.33g, reclaim raw material 0.78g.
Embodiment 3:4-chlorobenzyl chloride hydrolysis preparation 4,4 '-dichloro benzyl ether
The method of embodiment 1.But raw material 4-chlorobenzyl chloride (3.22g), KI (0.17g) reacted 24 hours.Get colourless acicular crystal product 1.70g, reclaim raw material 0.91g.
Embodiment 4:2-chlorobenzyl chloride hydrolysis preparation 2,2 '-dichloro benzyl ether
The method of embodiment 3.But raw material 2-chlorobenzyl chloride (3.22 g), KI (0.08 g).Get colourless thickness oily product 2.43g.
Embodiment 5:2,4-dichlorobenzyl chloride hydrolysis preparation 2,2 ', 4,4 '-the tetrachloro benzylic ether
The method of embodiment 3.But raw material 2-chlorobenzyl chloride (3.91g), KI (0.08g), reaction pressure is 20 MPas, reacts 12 hours.Get colourless acicular crystal product 2.71g.
Embodiment 6:3,4-dichlorobenzyl chloride hydrolysis preparation 3,3 ', 4,4 '-the tetrachloro benzylic ether
The method of embodiment 3.But raw material 2-chlorobenzyl chloride (3.91g), KI (0.17g).Get colourless thickness oily product 2.85g.
Claims (10)
1. a method of producing substituted dibenzyl ether is characterized in that this method is to adopt substituted benzyl halogen and water reaction, makees catalyzer with metal halide, and direct reaction promptly generates substituted dibenzyl ether, and separation, purifying get final product;
Wherein, substituted dibenzyl ether is suc as formula shown in (I), and substituted benzyl halogen is suc as formula shown in (II):
Here, Ar
1And Ar
2The expression substituted aryl, Ar
1And Ar
2According to formula (II) definition, k represents an integer of 0～5, and l represents an integer of 0～5, and k+l is an integer of 0～5, X
1Expression chlorine, bromine or iodine, X
2Expression fluorine, chlorine, bromine or iodine, when k 〉=2, X
2Can be identical or different, the substituting group that R represents is trifluoromethyl, itrile group, nitro, amide group, alkoxyl group or aryloxy, when l 〉=2, R can be identical or different.
2. method according to claim 1, the general formula that it is characterized in that metal halide is MX
3 m, wherein, M is a metal, X
3Be chlorine, bromine or iodine, m is 1,2 or 3.
3. method according to claim 2 is characterized in that metal halide MX
3 mM be Li, Na, K, Rb or Cs, X
3Be bromine or iodine, m is 1 or 2.
4. method according to claim 1 is characterized in that the Ar in the substituted dibenzyl ether formula (I)
1And Ar
2Identical.
5. method according to claim 1 is characterized in that the X of substituted benzyl halogen (II)
1Be chlorine or bromine, X
2Be chlorine or bromine, k is 1,2 or 3, and l is 1 or 2.
6. method according to claim 1 is characterized in that temperature of reaction is 40～320 ℃, is preferably 70～240 ℃, is preferably 90～200 ℃ especially; Reaction pressure is 0～22.5 MPa, is preferably 0～10 MPa, is preferably 0～3 MPa especially.
7, method according to claim 1 is characterized in that the water yield in molar ratio for 5～200 times of substituted benzyl halogen amount, is preferably 10～150 times, is preferably 20～100 times especially.
8. method according to claim 1 is characterized in that the metal halide amount in molar ratio for 0.1～20% of substituted benzyl halogen amount, is preferably 0.5～10%, is preferably 1～5% especially.
9. method according to claim 1 is characterized in that the reaction times is 0.5～48 hour, is preferably 1～24 hour, is preferably 2～12 hours especially.
10. method according to claim 1 is characterized in that reclaiming the haloid acid in the mixed reaction product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200510040614.3A CN1275919C (en) | 2005-06-20 | 2005-06-20 | Method for preparing substituted dibenzyl ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200510040614.3A CN1275919C (en) | 2005-06-20 | 2005-06-20 | Method for preparing substituted dibenzyl ether |
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| Publication Number | Publication Date |
|---|---|
| CN1709848A true CN1709848A (en) | 2005-12-21 |
| CN1275919C CN1275919C (en) | 2006-09-20 |
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|---|---|---|---|
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| Country | Link |
|---|---|
| CN (1) | CN1275919C (en) |
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Granted publication date: 20060920 Termination date: 20170620 |