CN110330411A - A kind of aromatic series allyl ether and its synthetic method and application - Google Patents
A kind of aromatic series allyl ether and its synthetic method and application Download PDFInfo
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- CN110330411A CN110330411A CN201910736560.6A CN201910736560A CN110330411A CN 110330411 A CN110330411 A CN 110330411A CN 201910736560 A CN201910736560 A CN 201910736560A CN 110330411 A CN110330411 A CN 110330411A
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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
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F216/14—Monomers containing only one unsaturated aliphatic radical
- C08F216/1416—Monomers containing oxygen in addition to the ether oxygen, e.g. allyl glycidyl ether
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Abstract
The invention belongs to chemical technology fields, and in particular to a kind of aromatic series allyl ether and its synthetic method and application.In the synthetic method of aromatic series allyl ether provided by the invention, the aromatic aldehyde replaced using phenolic hydroxyl group is raw material, after obtaining the aromatic hydrocarbons intermediate that phenolic hydroxyl group and alcoholic extract hydroxyl group replace after carrying out reduction reaction, after the mixed solvent being made up of water supplement and organic solvent, chloropropene reaction is added, the aromatic series allyl ether that there is alcoholic extract hydroxyl group to replace structure is obtained.Therefore synthetic method of the invention and traditional aromatic hydrocarbons replaced using phenolic hydroxyl group and alcohol radical are compared as starting material using bromopropene as etherifying agent to prepare, not only overall yield is higher, but also cost is lower.And aromatic series allyl ether provided by the invention and Fluorine containing olefine copolymerization polymer high temperature resistant, good insulation preformance, electronic material industry in have great application prospect.
Description
Priority application
This application claims " a kind of fragrance of Chinese invention patent application 201810921755.3 that August in 2018 is submitted on the 14th
The priority of race's allyl ether and its synthetic method and application ".
Technical field
The invention belongs to chemical technology fields, and in particular to a kind of synthetic method and the material of aromatic series allyl ether
Expect the application in field of communication technology.
Background technique
With the fast development of modern science and technology, high molecular material be in material science it is most representative, most develop
A kind of material of future.
With the 4G communication technology to the development of the 5G communication technology and the communication technology (6G to 10G) of high frequency will be future
Development trend, corresponding electronic equipment signal transmission high frequency and high-speed digitization, to carrying electronic component in electronic equipment
Baseplate material various performances requirement it is higher and higher: loss and the power loss for transmitting signal are small；In the medium of substrate,
Loss of signal and power loss can occur for signals transmission, and the size of loss increases as the frequency of transmission signal increases
Greatly, the increase of medium medium dielectric constant microwave medium (ε r) 1/2 and loss tangent angle tan δ and increase.Since the dielectric loss of signal is changed into
Thermal energy and cause substrate temperature rise, substrate temperature rise causes bigger signal media to be lost again, make signal transmission be deteriorated.Therefore, for
The transmission substrate of high-frequency signal and high-speed digital signal must select the material of low-k and low-dielectric loss.Material sheet
Body should also meet low water absorption, high-fire resistance, mechanical property and excellent processing performance etc..
General common epoxy resin, polytetrafluoroethylene (PTFE) (PTFE), polyimides (PI), polyphenylene oxide (PPE), polymerizable mesogenic
Object (LCP) dielectric constant is respectively 3.9,2.1,3.3,2.5,2.9.Fluoropolymer has good low Jie under high frequency condition
Electrical property, but pure polytetrafluoroethylene (PTFE) (PTFE) processing performance is poor, needs to carry out the bonding of processing increase and copper foil on its surface
Property, it just can be carried out the application of next step.Common PCB substrate is not to be able to satisfy high speed transmission of signals to require at present, this will be at
For the developing technology of electronics industry " bottleneck ", therefore, exploitation easy processing, high performance fluorine resin advanced low-k materials are
Reasonably necessary, the exploitation for the polymerized monomer that can be copolymerized with Fluorine containing olefine is the key that obtain high performance resin.What we developed
Aromatic series allyl ether will meet this functional requirement.
Aromatic series allyl ether is a kind of promising 5G material, and the substance of this class formation is replaced with phenolic hydroxyl group
It is fragrant and mellow be used as starting material, and prepared using bromopropene as etherifying agent.But both cost of material are very expensive, lead to
Crossing them, only cost of material is just very high to synthesize aromatic series allyl ether.Meanwhile this reaction is related to immiscible organic-inorganic
Two phase reaction, reaction efficiency is low, and yield is not high, it is also necessary to phase transfer catalyst be added and promote reaction, therefore it is multiple to increase technique
Polygamy, therefore total preparation cost is very high.And the starting material using the aromatic aldehyde of phenolic hydroxyl group substitution as preparation that we develop, ether
Agent uses chloropropene, both cost of material are lower.Meanwhile the intermediate of preparation do not have to separating-purifying can directly carry out it is next
Step reaction, avoids the loss of intermediate and the complexity of technique；The mixed solvent method of use, so that not needing phase transfer catalysis (PTC)
Agent can also react fully generation, and this not only reduces process complexities, and have very high yield.Therefore, of the invention
Although synthetic method increases a step, but total preparation cost is lower, this provides possibility for industrialization.
Summary of the invention
In view of this, the purpose of the present invention is to provide a kind of synthetic method of aromatic series allyl ether and aromatic series allyls
The application of base ether.
To achieve the above object, the technical solution of the present invention is as follows:
A kind of synthetic method of aromatic series allyl ether, which is characterized in that with III compound of formula to synthesize starting material, lead to
It crosses reduction reaction and obtains II compound of intermediate formula, II compound of formula is added in the mixed solvent system of organic solvent and water
Sufficiently dissolution；Chloropropene is added to be reacted with alkali to get type I compound aromatic series allyl ether is arrived；Reaction structure formula is such as
Under:
Wherein, the integer that n is 1 to 4 in formula III；N=1 in Formula II, the Formula II compound are 4- salicylic alcohol；Formulas I
Middle n=1, the type I compound are 4- allyloxy benzyl alcohol.
Preferably, III compound n=1 when described, III compound of formula are 4- hydroxy benzaldehyde.
The not common allyl bromide, bromoallylene of the reactant halide used in this reaction uses allyl chloride.Allyl
Base chlorine is more cheap than allyl bromide, bromoallylene, can a large amount of save the costs when being used as industrialized production.Chloropropene is just than bromopropene price
It preferably, can be with save the cost when being used as industrialized production.Since to slough ability poorer than the bromide ion of bromopropene for the chloride ion of chloropropene,
In order to improve the reactivity of chloropropene, we make using energy organic solvent miscible with water with water jointly in the present invention
For the solvent of etherification reaction.By the use of this mixed solvent, water energy dissolves organic catalyst alkali, and organic solvent can dissolve
Organic reactant, and water energy is dissolved each other with organic solvent, so that organic can come into full contact with inorganic reaction object is reacted,
The phase transfer catalyst that usually this kind of reaction needs is not needed, this not only lowers process complexities, cost is advantageously reduced, and
And reaction is more complete, and yield is higher, even if using the cheap but active chloropropene not as good as bromopropene as etherifying agent,
Higher yield can be obtained.Meanwhile water can also inhibit in second step etherification reaction, the alcoholic extract hydroxyl group ginseng in II structure of intermediate formula
With react, and only allow phenolic hydroxyl group participate in reaction, to be further reduced the generation of by-product.
Further, using formula III compound as starting material, reduction reaction occurs in protic with reducing agent and obtains
Target substance formula I is prepared by Formula II compound for intermediate Formula II；The substituent group of the formula III compound can be
O-, m-, contraposition replaces, and is also possible to straight chain, branch replaces.
Further, the whole system of synthetic intermediate Formula II does not have to separating-purifying, after directly adding solvent and required raw material
Carry out second step etherification reaction.This not only will not influence second step reaction, but also also improve overall yield, and it is multiple to reduce technique
Polygamy, to decrease cost.
Reaction vessel can be open container in synthesis, be also possible to common closed container, be also possible to high-pressure sealed
Container.With high-pressure closed vessel, it can be passed through the inert gases such as nitrogen, argon gas into system, maintain positive pressure.
Further, above-mentioned synthetic method further includes that the aromatic series allyl ether that will be obtained passes through rectification under vacuum or crystallization and purification
Obtain aromatic series allyl ether product.
Preferably, obtained aromatic series allyl ether is washed with water or saturated sodium-chloride water solution, until the water of washing
For neutrality；Water is removed in separation, and the crude product after washing is purified by modes such as rectification under vacuum, freezing and crystallizings to get aromatic series allyl
Base ether product.
Further, the organic solvent include methanol, ethyl alcohol, acetone, tetrahydrofuran it is one or more；The solvent
It is 1:0.01~100 with the volume ratio of organic solvent and water in the mixed solvent system of water.
Further, the molar ratio of II compound of formula and chloropropene, alkali is 1:1~2:1~2.
Further, the alkali is the alkali of alkali metal containing element or the alkali of other alkaline earth metal forms, including KOH, NaOH, Ca
(OH)2, reaction temperature is 30~140 DEG C；Reaction time is 2~48h.
Further, the protic can be methanol, ethyl alcohol, water or their mixture；The reducing agent is boron
Sodium hydride or potassium borohydride.
Another object of the present invention, which also resides in, provides a kind of aromatic series allyl ether.
The aromatic series allyl ether according to made from the above method.
Another object of the present invention, which also resides in, provides the application of aromatic series allyl ether obtained.
Application in above-mentioned aromatic series allyl ether high frequency dielectric materials needed for preparing 5G and the above communication technology.
Further, the aromatic series allyl ether can polymerize to form copolymer with Fluorine containing olefine, and the Fluorine containing olefine can
To be one of chlorotrifluoroethylene, tetrafluoroethene, hexafluoropropene or a variety of.
Further, in the copolymer aromatic series allyl ether and Fluorine containing olefine molar concentration rate are as follows: 20~80:20~
80。
Copolymer of the present invention is made of having structure unit: (a) fluoroolefins；(b) type I compound.Each structural unit
Content be respectively as follows: (a) greater than 20mol%, be less than 80mol%, (b) be greater than 20mol%, be less than 80mol%.Structure is as follows
Show:
The reagent composition that side reaction object generates in a kind of synthesis process can be reduced aromatic series allyl ether, the reagent
Composition is made of reagent a and reagent b, reagent a be organic solvent, including methanol, ethyl alcohol, acetone, tetrahydrofuran one kind or
It is a variety of；Reagent b is water；The volume ratio of the reagent a and reagent b is 1:0.01~100.
Reagent composition provided by the invention, reagent b can dissolve inorganic reaction object, and reagent a can dissolve organic reactant
Intermediate: p-Hydroxybenzylalcohol and chloropropene, organic in this way can come into full contact with inorganic reaction object are reacted, are not needed
Phase transfer catalyst such as tetrabutylammonium bromide that usually this kind of reaction needs etc. (phase transfer catalyst is added and increases cost, after
Phase needs to separate removal, increases process complexity), and react more complete, yield is higher.Water can also inhibit intermediate reaction
Alcoholic extract hydroxyl group in object p-Hydroxybenzylalcohol structure participates in reaction, and phenolic hydroxyl group is only allowed to participate in reaction, to reduce the production of by-product
It is raw.
The beneficial effects of the present invention are:
1) in the synthetic method of aromatic series allyl ether provided by the invention, using the aromatic aldehyde of phenolic hydroxyl group substitution as raw material,
The aromatic hydrocarbons intermediate that phenolic hydroxyl group and alcoholic extract hydroxyl group replace is obtained after carrying out reduction reaction, the mixing of water supplement and organic solvent composition is molten
After agent, chloropropene reaction is added, obtains the aromatic series allyl ether that there is alcoholic extract hydroxyl group to replace structure.Wherein, it is taken with alcoholic extract hydroxyl group
The aromatic aldehyde in generation can reduce cost of material as etherifying agent as starting material, chloropropene.
2) in the synthetic method of aromatic series allyl ether provided by the invention, the intermediate that the first step is reacted does not have to divide
From purification, it is directly used in the reaction of next step, avoid the loss of separating-purifying bring and reduces process complexity, is conducive to
Reduce preparation cost.
3) solvent that the present invention provides the mixed solvents of a kind of organic solvent and water composition as etherification reaction, this water
And can organic solvent miscible with water collectively as system solvent so that not needing common phase in second step etherification reaction
Transfer catalyst is not only avoided because of post-processing separation phase transfer catalyst bring process complexity, and even with
The lower chloropropene of reactivity also can make correlated response have higher yield as etherifying agent, to greatly reduce preparation
Cost.Meanwhile the presence of water can also inhibit the alcoholic extract hydroxyl group in etherification reaction to participate in reaction, thus reduce the generation of by-product,
Improve yield.
4) aromatic series allyl ether provided by the invention polymerize with Fluorine containing olefine, and obtained resin is for meeting 5G or more
The demand of high frequency dielectric materials needed for the communication technology.
Specific embodiment
The preferred embodiment of the present invention is described in detail below.Illustrated embodiment is in order to preferably to of the invention
Content is illustrated, but is not that the contents of the present invention are only limitted to illustrated embodiment.So those skilled in the art's root
Nonessential modifications and adaptations are carried out to embodiment according to foregoing invention content, still fall within protection scope of the present invention.
Embodiment 1
50 grams of p-Hydroxybenzylalcohols (0.40mol) are added in the 1L autoclave for filling 150 grams of acetone, add water
100g, chloropropene 37g (0.49mol), 22.4 grams of KOH (0.40mol).It is closed to be passed through nitrogen, maintains under 1 atmospheric pressure of pressure,
55 DEG C of insulation reactions of temperature about 15 hours.
After reaction, rotary evaporation removes the acetone in (recycling) reaction system, and remaining liquid pours into liquid separation leakage while hot
Static layering in bucket, goes water phase, takes upper organic phase, obtains the crude product 56.3g (GC detection level is 90%) of reaction preparation, receives
Rate 85%.
Obtained 4- allyloxy benzyl alcohol crude product is washed with saturated sodium-chloride water solution, until the water of washing is neutrality.
Water is separated, the crude product after washing is purified with rectification under vacuum.(3bar) collects 120 DEG C of fraction to get product under a high vacuum
For colourless transparent liquid, GC analyzes content 99.3%.1H NMR(400MHz,CDCl3) δ 7.28 (d, J=4.0Hz, 2H) .6.91
(d, J=8.0Hz, 2H), 6.09-6.02 (m, 1H), 5.41 (d, J=8.0Hz, 1H), 5.29 (d, J=8.0Hz, 1H), 4.62
(s, 2H), 4.55 (d, J=8.0Hz, 2H).
Embodiment 2
300 grams of methanol are added in three-necked flask, add 100 grams of parahydroxyben-zaldehyde (0.82mol) stirring and dissolvings, then add
Add a small amount of potassium hydroxide into system.Reaction system is cooled to 0 DEG C with low temperature water-bath.Sodium borohydride 20g (0.53mol) is dissolved in
It in KOH dilute aqueous solution (amount of water preferably just dissolving, PH ﹥ 10), is added in there-necked flask and is reacted by the way of dropwise addition, controlled
Rate of addition processed keeps system temperature to be no more than 10 DEG C.After being added dropwise, the reaction was continued 20 minutes, passes through thin-layer chromatography contact plate
To determine the end time.
The intermediate system that the first step is reacted all is poured into 2L autoclave, and water 300g, chloropropene 69g is added
(0.90mol),45gKOH(0.78mol).It is closed to be passed through nitrogen, maintains under 1 atmospheric pressure of pressure, 55 DEG C of insulation reactions of temperature are about
15 hours.
After reaction, rotary evaporation removes the methanol in (recycling) reaction system, and remaining liquid pours into liquid separation leakage while hot
Static layering in bucket, goes water phase, takes upper organic phase, obtains 4- allyloxy benzyl alcohol crude product 249g (the GC inspection of reaction preparation
Surveying content is 94%) yield 90%.
Obtained 4- allyloxy benzyl alcohol crude product is washed with saturated sodium-chloride water solution, until the water of washing is neutrality.
Water is separated, the crude product after washing is purified with rectification under vacuum.(3bar) collects 120 DEG C of fraction to get product under a high vacuum
For colourless transparent liquid, GC analyzes content 99.5%.
Embodiment 3
300 grams of methanol are added in three-necked flask, add 100 grams of parahydroxyben-zaldehyde (0.82mol) stirring and dissolvings, then add
Add a small amount of potassium hydroxide into system.Reaction system is cooled to 0 DEG C with low temperature water-bath.Sodium borohydride 20g (0.53mol) is dissolved in
It in KOH dilute aqueous solution (amount of water preferably just dissolving, PH ﹥ 10), is added in there-necked flask and is reacted by the way of dropwise addition, controlled
Rate of addition processed keeps system temperature to be no more than 10 DEG C.After being added dropwise, the reaction was continued 20 minutes, passes through thin-layer chromatography contact plate
To determine the end time.
The intermediate system that the first step is reacted all is poured into 2L autoclave, and water 300g, chloropropene 69g is added
(0.90mol),45gKOH(0.78mol).It is closed to be passed through nitrogen, maintains under 1 atmospheric pressure of pressure, 55 DEG C of insulation reactions of temperature are about
15 hours.
After reaction, rotary evaporation removes the methanol in (recycling) reaction system, and remaining liquid pours into liquid separation leakage while hot
Static layering in bucket, goes water phase, takes upper organic phase, obtains 4- allyloxy benzyl alcohol crude product 249g (the GC inspection of reaction preparation
Surveying content is 94%) yield 90%.
Obtained 4- allyloxy benzyl alcohol crude product is washed with saturated sodium-chloride water solution, until the water of washing is neutrality.
Water is separated, the crude product after washing is purified with rectification under vacuum.(3bar) collects 120 DEG C of fraction to get product under a high vacuum
For colourless transparent liquid, GC analyzes content 99.5%.
Embodiment 4
4000 grams of methanol are added in reaction kettle kettle, it is molten to add 1500 grams of parahydroxyben-zaldehyde (12.30mol) stirrings
Solution, then a certain amount of potassium hydroxide is added into system, make reaction system in alkalescent.Reaction system is cooled to low temperature water-bath
0 degree.Sodium borohydride 300g (7.95mol) is dissolved in KOH dilute aqueous solution (amount of water is preferably just dissolving), using dropwise addition
Mode, which is added in glass kettle, reacts, and controls rate of addition, and system temperature is kept to be no more than 10 DEG C.After being added dropwise, it is warming up to
The reaction was continued 20 minutes for room temperature, determines the end time by thin-layer chromatography contact plate.
After reaction, a certain amount of water (or dilute hydrochloric acid) is added to quench to sodium borohydride remaining in reaction system
It goes out, until system bubble-free generates.
The intermediate system that the first step is reacted all is poured into 10L autoclave, and water 2700g, chloropropene 1035g is added
(13.5mol), KOH 655g (11.7mol).It is passed through nitrogen, is maintained under 3 atmospheric pressure of pressure, 55 DEG C of insulation reactions of temperature about 10
Hour.
After reaction, rotary evaporation removes the methanol in (recycling) reaction system, and remaining liquid pours into separatory funnel
Static layering goes lower water phase, takes upper organic phase.Organic phase is washed with dilute hydrochloric acid solution, until the water of washing is neutral or weak
Acid (pH=5-7).Water is removed in separation, obtains the VE502 crude product 1851g (it is 90% that GC, which detects purity) of reaction preparation, yield
92%.
Obtained VE502 crude product carries out rectification under vacuum purification.(70 pa) collects 120 DEG C or so of fraction under a high vacuum,
Up to product, GC analyzes content 99.7%.
Finally, it is stated that the above examples are only used to illustrate the technical scheme of the present invention and are not limiting, although referring to compared with
Good embodiment describes the invention in detail, those skilled in the art should understand that, it can be to skill of the invention
Art scheme is modified or replaced equivalently, and without departing from the objective and range of technical solution of the present invention, should all be covered at this
In the scope of the claims of invention.
Claims (12)
1. a kind of synthetic method of aromatic series allyl ether, which is characterized in that with III compound of formula to synthesize starting material, pass through
Reduction reaction obtains II compound of intermediate formula, and II compound of formula is added in the mixed solvent system of organic solvent and water and is filled
Divide dissolution；Chloropropene is added to be reacted with alkali to get type I compound aromatic series allyl ether is arrived；Reaction structure formula is as follows:
Wherein, the integer that n is 1 to 4 in formula III；N=1 in Formula II, the Formula II compound are 4- salicylic alcohol；N=in Formulas I
1, the type I compound is 4- allyloxy benzyl alcohol.
2. synthetic method according to claim 1, which is characterized in that using formula III compound as starting material, with reducing agent
Reduction reaction occurs in protic and obtains intermediate Formula II, target substance formula I is prepared by Formula II compound；
The substituent group of the formula III compound can be o-, m-, contraposition and replace, and be also possible to straight chain, branch replaces.
3. synthetic method according to claim 2, which is characterized in that the whole system of synthetic intermediate Formula II does not have to separation
Purification carries out second step etherification reaction after directly adding solvent and required raw material.
4. synthetic method according to claim 1, which is characterized in that the organic solvent include methanol, ethyl alcohol, acetone,
Tetrahydrofuran it is one or more；The volume ratio of organic solvent and water is 1 in the mixed solvent system of the solvent and water:
0.01~100.
5. synthetic method according to claim 1, which is characterized in that mole of II compound of formula and chloropropene, alkali
Than for 1:1~2:1~2.
6. synthetic method according to claim 1, which is characterized in that the alkali is the alkali or other alkali of alkali metal containing element
The alkali of earth metal form, including KOH, NaOH, Ca (OH)2, reaction temperature is 30~140 DEG C；Reaction time is 2~48h.
7. synthetic method according to claim 2, which is characterized in that the protic can be methanol, ethyl alcohol, water
Or their mixture；The reducing agent is sodium borohydride or potassium borohydride.
8. the aromatic series allyl ether that the described in any item synthetic methods of claim 1-7 synthesize.
9. aromatic series allyl ether according to any one of claims 8 is in the high frequency dielectric materials needed for preparation 5G and the above communication technology
Application.
10. application according to claim 9, which is characterized in that the aromatic series allyl ether can be poly- with Fluorine containing olefine
Conjunction forms copolymer, and the Fluorine containing olefine can be one of chlorotrifluoroethylene, tetrafluoroethene, hexafluoropropene or a variety of.
11. application according to claim 10, which is characterized in that aromatic series allyl ether and fluorine-containing alkene in the copolymer
The molar concentration rate of hydrocarbon are as follows: 20~80:20~80.
12. the reagent composition that side reaction object generates in a kind of synthesis process that can be reduced aromatic series allyl ether, feature exist
In the reagent composition is made of reagent a and reagent b, and reagent a is organic solvent, including methanol, ethyl alcohol, acetone, tetrahydro furan
That mutters is one or more；Reagent b is water；The volume ratio of the reagent a and reagent b is 1:0.01~100.
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| CN109160873A (en) | 2019-01-08 |
| CN110407674A (en) | 2019-11-05 |
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