CN109534995A - A kind of preparation method of phenylacetate class compound - Google Patents

A kind of preparation method of phenylacetate class compound Download PDF

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Publication number
CN109534995A
CN109534995A CN201811584409.7A CN201811584409A CN109534995A CN 109534995 A CN109534995 A CN 109534995A CN 201811584409 A CN201811584409 A CN 201811584409A CN 109534995 A CN109534995 A CN 109534995A
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phenylacetate
class compound
formula
esterification
storage tank
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CN109534995B (en
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金灿
孙彬
苏为科
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Zhejiang University of Technology ZJUT
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Zhejiang University of Technology ZJUT
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a kind of preparation methods of phenylacetate class compound, it is using the fortified phenol as shown in formula (I) and acetic anhydride as reaction raw materials, using sodium hydrate aqueous solution as solvent, esterification is carried out in tubular reactor, phenylacetate class compound as shown in the formula (II) is made, reaction equation is as follows:In formula (I) and formula (II), substituent R is the alkoxy carbonyl group of hydrogen, the alkyl of C1~C6, nitro, cyano, halogen, carboxyl or C1~C12.The present invention is by the way of the pipe reaction of approximate plug flow, and for material almost without back-mixing, mass-and heat-transfer is high-efficient in pipe reaction, reduces the generation of side reaction significantly, and product yield and purity are higher.

Description

A kind of preparation method of phenylacetate class compound
Technical field
The present invention relates to a kind of preparation methods of phenylacetate class compound.
Background technique
Substituted phenylacetate series compound is important intermediate, is widely used in the neck such as medicine, chemical industry, pesticide Domain, if phenylacetate can be used for synthesizing cholagogic parahydroxyacet-ophenone, acetic acid p-nitrophenyl acetate is receptor blocking agent hydrochloric acid plug The important source material of Li Luoer, acetylsalicylic acid can be used as analgesic-antipyretic etc..
Currently, synthesis of acetic acid phenyl ester series compound main method is to issue using phenol as raw material in the effect of the alkali such as pyridine Raw esterification (Heter DEG C of yclic Communications, 2017,23 (4), 325-330330; Org. Lett. 2014,16,236 239), can also occur under Lewis acid catalysis esterification (Tetrahedron Letters, 2014, 55(4), 910-912;Heter DEG C of yclic Letters, 6 (2), 2016,323-327).The above method prepares acetic acid benzene Ester has the disadvantage that
1) alkaline reagent dosage is big, and nitrogenous effluent treatment is difficult, and post-processing trouble, quantity of three wastes is big, is unfavorable for environmental protection；
2) acidic catalyst is expensive, at high cost, and reaction condition is harsher, and the reaction time is long.
3) batch (autoclave) is reacted since the inventory reacted online is big, acetic anhydride, the chloroacetic chloride isoreactivity reagent used Chance water, air are extremely easy in decomposition, and are easy slug and are even exploded, there are great security risks.
Summary of the invention
For above-mentioned technical problem of the existing technology, the purpose of the present invention is to provide a kind of phenylacetate class chemical combination The preparation method of object.
A kind of preparation method of phenylacetate class compound, it is characterised in that with fortified phenol and second as shown in formula (I) Acid anhydrides is reaction raw materials, and using sodium hydrate aqueous solution as solvent, esterification is carried out in tubular reactor, is made such as formula (II) phenylacetate class compound, reaction equation shown in are as follows:
In formula (I) and formula (II), substituent R is the alkane of hydrogen, the alkyl of C1~C6, nitro, cyano, halogen, carboxyl or C1~C12 Oxygen carbonyl.
The preparation method of a kind of phenylacetate class compound, it is characterised in that specifically includes the following steps: will be as Fortified phenol shown in formula (I), which is dissolved in sodium hydrate aqueous solution, to be placed in the first storage tank, and acetic anhydride is placed in the second storage tank； Material in first storage tank and the second storage tank is conveyed through metering pump respectively, into mixer in mixed, mixed liquor is continuously Esterification is carried out into tubular reactor, the feed liquid after the esterification flowed out in tubular reactor is post-treated, obtains mesh Mark acetic acid product benester compound.
The preparation method of a kind of phenylacetate class compound, it is characterised in that the temperature of esterification is 5 ~ 100 DEG C, preferably 20 ~ 40 DEG C.
The preparation method of a kind of phenylacetate class compound, it is characterised in that mixed liquor is in tubular reactor Residence time is 0.5 ~ 60 minute, preferably 1 ~ 5 minute.
A kind of preparation method of the phenylacetate class compound, it is characterised in that during carrying out esterification, The molar ratio of the fortified phenol as shown in formula (I) and sodium hydroxide is 1:1.0 ~ 2.0.
The preparation method of a kind of phenylacetate class compound, it is characterised in that the step of post-processing are as follows: esterification is anti- Feed liquid stratification after answering is oil reservoir and water layer, and liquid separation removes water layer, and oil reservoir successively uses deionized water, saturated sodium bicarbonate water Solution, deionized water washing, washing to neutrality is dry, obtains target product phenylacetate class compound.
Compared with prior art, effect of the invention is embodied in:
1. for material almost without back-mixing, mass-and heat-transfer is high-efficient in pipe reaction, reduce the generation of side reaction, product significantly Yield and purity are higher.2. continuous pipe type reaction can accurately control response parameter, using continuous operation mode, it is easier to real Existing automation control, improves production efficiency.3. the online reacting dose of pipe reaction is small, and easily realizes interlocked control, technique is improved Essential safety, and technical solution of the present invention use inorganic base sodium hydroxide, the nitrogenous base reagent such as triethylamine has been got rid of, from source Head avoids the generation of nitrogenous effluent.Phenol generates sodium phenate after being dissolved in sodium hydroxide, experiments have shown that its reactivity is significantly Yu Shui, acid anhydrides and sodium phenate esterification speed are greater than the hydrolysis of acid anhydrides and water, and phenol and acid anhydrides in traditional handicraft Esterification speed be less than the hydrolysis of water and acid anhydrides, and the inventory reacted online in reactor is more anti-than traditional autoclave Several orders of magnitude should be lacked, therefore traditional still reaction may lead to acid anhydrides selective hydrolysis because of the water inlet of operation error system, reaction is lost Control, but water can be used as solvent in the present invention completely, and security risk is significantly reduced.Secondly, the esterification of phenol is strong Exothermic reaction, concentration, temperature have a large effect to the reaction, and traditional still reaction is full-mixing type, isotropism in kettle, everywhere Concentration, temperature, reaction speed are consistent, and pipe reaction is flowing chemistry, and pipeline radial section is believed that the basic same sex, but axis It is different because of residence time difference to concentration, reaction speed everywhere etc..In addition, still reaction volume is big, mass transfer, heat-transfer effect Difference, pipe reaction mass-and heat-transfer speed small in size is fast, can obviously reduce some side reactions of esterification reaction process.Therefore, it flows Pipe type esterification reaction and full-mixing type autoclave esterification have essential distinction, technical solution of the present invention are thus used, for easily producing Raw by-product has preferable effect to thermo-responsive phenol esterification.
Detailed description of the invention
Fig. 1 is the process flow chart in embodiment 1；
In figure: the first storage tank of A-, the second storage tank of B-, the first metering pump of P1-, the second metering pump of P2-, T- mixer, R- tubular type are anti- Answer device, C- receiving tank.
Specific embodiment
The present invention is further explained in the light of specific embodiments, but the scope of protection of the present invention is not limited thereto.
Embodiment 1
It is sequentially added in the first storage tank A deionized water (30 L), phenol (9.4kg, 100mol), and sodium hydroxide (4.4kg, 110 Mol) and stirring and dissolving is to clear, adds deionized water precise volume setting to 50 L, it is the water-soluble of 2.0 mol/L that phenol concentration, which is made, Liquid, sealing is stand-by after mixing evenly.Acetic anhydride 13.3kg(130 moL, density 1.08g/mL are added in the second storage tank B, mole Concentration 10.60mol/L) sealing is for use.
Material in first storage tank A and the second storage tank B is delivered to through the first metering pump P1 and the second metering pump P2 mixed respectively After clutch T is mixed (control phenol: the molar flow ratio that feeds intake of acetic anhydride is 1:1.3), mixed liquor is continuously into tubular type Reactor R carries out esterification, and temperature maintains 20 DEG C in tubular reactor R, mixed liquor residence time in tubular reactor R It is 2 minutes.Feed liquid after the esterification flowed out in tubular reactor R enters receiving tank C, and stratification is oil reservoir and water layer, Liquid separation removes water layer, and oil reservoir successively washs (washing to neutrality) with deionized water, saturated sodium bicarbonate aqueous solution, deionized water, Oil reservoir (removes desiccant sodium sulphate) after being dried, filtered with anhydrous sodium sulfate and obtains colorless oil phenylacetate 13.1kg, yield 96%, content 99.1%.
Embodiment 2
Deionized water (30 L), p-methyl phenol (10.8kg, 100mol), sodium hydroxide are sequentially added in the first storage tank A (4.4kg, 110 mol) and stirring and dissolving add deionized water precise volume setting to 50 L, p-methyl phenol concentration are made to clear For the aqueous solution of 2.0 mol/L, sealing is stand-by after mixing evenly.Acetic anhydride 13.3kg(130 moL is added in the second storage tank B, Density 1.08g/mL, molar concentration 10.60mol/L) sealing is for use.
The material in the first storage tank A and the second storage tank B is delivered to (control after mixer is mixed respectively with metering pump P-methyl phenol: the molar flow ratio of acetic anhydride is 1:1.3), mixed liquor carries out esterification continuously into tubular reactor, Temperature maintains 20 DEG C in tubular reactor, and mixed liquor residence time in tubular reactor is 2 minutes.Stream in tubular reactor The feed liquid after esterification out enters receiving tank, and stratification is oil reservoir and water layer, and liquid separation removes water layer, and oil reservoir is successively spent Ionized water, saturated sodium bicarbonate aqueous solution, deionized water washing (washing to neutrality), oil reservoir is dried, filtered with anhydrous sodium sulfate After obtain colorless oil acetic acid to methyl phenyl ester 14.4kg, yield 96%, content 99.0%.
Embodiment 3
Deionized water (30 L), p-nitrophenol (13.9kg, 100mol), sodium hydroxide are sequentially added in the first storage tank A (4.4kg, 110 mol) and stirring and dissolving add deionized water precise volume setting to 50 L, p-nitrophenol concentration are made to clear For the aqueous solution of 2.0 mol/L, sealing is stand-by after mixing evenly.Acetic anhydride 13.3kg(130 moL is added in the second storage tank B, Density 1.08g/mL, molar concentration 10.60mol/L) sealing is for use.
The material in the first storage tank A and the second storage tank B is delivered to (control after mixer is mixed respectively with metering pump P-nitrophenol: the molar flow ratio of acetic anhydride is 1:1.3), mixed liquor carries out esterification continuously into tubular reactor, Temperature maintains 20 DEG C in tubular reactor, and mixed liquor residence time in tubular reactor is 2 minutes.Stream in tubular reactor The feed liquid after esterification out enters receiving tank, and the feed liquid after esterification is filtered, the solid being obtained by filtration, solid are collected Successively washed (washing to neutrality) with deionized water, saturated sodium bicarbonate aqueous solution, deionized water, it is dry, obtain white acetic acid 17.2 kg of p-nitrophenyl ester, 78 ~ 79 DEG C of fusing point, yield 95%, content 98.9%.
Embodiment 4
It is sequentially added in the first storage tank A deionized water (30 L), phenol (9.4 kg, 100mol), sodium hydroxide (4 kg, 100mol) and stirring and dissolving is to clear, adds deionized water precise volume setting to 50 L, it is 2.0 mol/L's that phenol concentration, which is made, Aqueous solution, sealing is stand-by after mixing evenly.10.2 kg(100moL of acetic anhydride, density 1.08g/mL are added in the second storage tank B, Molar concentration 10.60mol/L) sealing is for use.
The material in the first storage tank A and the second storage tank B is delivered to (control after mixer is mixed respectively with metering pump Phenol: the molar flow ratio of acetic anhydride is 1:1), mixed liquor carries out esterification, pipe reaction continuously into tubular reactor Temperature maintains 20 DEG C in device, and mixed liquor residence time in tubular reactor is 2 minutes.The esterification flowed out in tubular reactor Feed liquid after reaction enters receiving tank, and stratification is oil reservoir and water layer, and liquid separation removes water layer, oil reservoir successively use deionized water, Saturated sodium bicarbonate aqueous solution, deionized water washing (washing to neutrality), oil reservoir obtains nothing after being dried, filtered with anhydrous sodium sulfate 12.1 kg of color oily phenylacetate, yield 89%, content 98.8%.
Embodiment 5
It is sequentially added in the first storage tank A deionized water (30 L), phenol (9.4 kg, 100mol), sodium hydroxide (8 kg, 200mol) and stirring and dissolving is to clear, adds deionized water precise volume setting to 50 L, it is 2.0 mol/L's that phenol concentration, which is made, Aqueous solution, sealing is stand-by after mixing evenly.20.4 kg(200 moL of acetic anhydride, density 1.08g/ are added in the second storage tank B ML, molar concentration 10.60mol/L) sealing is for use.
The material in the first storage tank A and the second storage tank B is delivered to (control after mixer is mixed respectively with metering pump Phenol: the molar flow ratio of acetic anhydride is 1:2), mixed liquor carries out esterification, pipe reaction continuously into tubular reactor Temperature maintains 20 DEG C in device, and mixed liquor residence time in tubular reactor is 2 minutes.The esterification flowed out in tubular reactor Feed liquid after reaction enters receiving tank, and stratification is oil reservoir and water layer, and liquid separation removes water layer, oil reservoir successively use deionized water, Saturated sodium bicarbonate aqueous solution, deionized water washing (washing to neutrality), oil reservoir obtains nothing after being dried, filtered with anhydrous sodium sulfate 10.9 kg of color oily phenylacetate, yield 80%, content 97.1%.
Embodiment 6
It is sequentially added in the first storage tank A deionized water (30 L), phenol (9.4kg, 100mol), and sodium hydroxide (4.4kg, 110 Mol) and stirring and dissolving is to clear, adds deionized water precise volume setting to 50 L, it is the water-soluble of 2.0 mol/L that phenol concentration, which is made, Liquid, sealing is stand-by after mixing evenly.Acetic anhydride 13.3kg(130 moL, density 1.08g/mL are added in the second storage tank B, mole Concentration 10.60mol/L) sealing is for use.
The material in the first storage tank A and the second storage tank B is delivered to (control after mixer is mixed respectively with metering pump Phenol: the molar flow ratio of acetic anhydride is 1:1.3), mixed liquor carries out esterification continuously into tubular reactor, and tubular type is anti- Temperature in device is answered to maintain 20 DEG C, mixed liquor residence time in tubular reactor is 0.5 minute.It is flowed out in tubular reactor Feed liquid after esterification enters receiving tank, and stratification is oil reservoir and water layer, and liquid separation removes water layer, and oil reservoir successively uses deionization Water, saturated sodium bicarbonate aqueous solution, deionized water washing (washing to neutrality), oil reservoir obtain after being dried, filtered with anhydrous sodium sulfate To 9.5 kg of colorless oil phenylacetate, yield 70%, content 94.8%.
Embodiment 7
It is sequentially added in the first storage tank A deionized water (30 L), phenol (9.4kg, 100mol), and sodium hydroxide (4.4kg, 110 Mol) and stirring and dissolving is to clear, adds deionized water precise volume setting to 50 L, it is the water-soluble of 2.0 mol/L that phenol concentration, which is made, Liquid, sealing is stand-by after mixing evenly.Acetic anhydride 13.3kg(130 moL, density 1.08g/mL are added in the second storage tank B, mole Concentration 10.60mol/L) sealing is for use.
The material in the first storage tank A and the second storage tank B is delivered to (control after mixer is mixed respectively with metering pump Phenol: the molar flow ratio of acetic anhydride is 1:1.3), mixed liquor carries out esterification continuously into tubular reactor, and tubular type is anti- Temperature in device is answered to maintain 20 DEG C, mixed liquor residence time in tubular reactor is 60 minutes.It is flowed out in tubular reactor Feed liquid after esterification enters receiving tank, and stratification is oil reservoir and water layer, and liquid separation removes water layer, and oil reservoir successively uses deionization Water, saturated sodium bicarbonate aqueous solution, deionized water washing (washing to neutrality), oil reservoir obtain after being dried, filtered with anhydrous sodium sulfate To 12 kg of colorless oil phenylacetate, yield 88%, content 98.5%.
Embodiment 8
It is sequentially added in the first storage tank A deionized water (30 L), phenol (9.4kg, 100mol), and sodium hydroxide (4.4kg, 110 Mol) and stirring and dissolving is to clear, adds deionized water precise volume setting to 50 L, it is the water-soluble of 2.0 mol/L that phenol concentration, which is made, Liquid, sealing is stand-by after mixing evenly.Acetic anhydride 13.3kg(130 moL, density 1.08g/mL are added in the second storage tank B, mole Concentration 10.60mol/L) sealing is for use.
The material in the first storage tank A and the second storage tank B is delivered to (control after mixer is mixed respectively with metering pump Phenol: the molar flow ratio of acetic anhydride is 1:1.3), mixed liquor carries out esterification continuously into tubular reactor, and tubular type is anti- Temperature in device is answered to maintain -5 DEG C, mixed liquor residence time in tubular reactor is 2 minutes.The ester flowed out in tubular reactor Feed liquid after changing reaction enters receiving tank, and stratification is oil reservoir and water layer, and liquid separation removes water layer, and oil reservoir successively uses deionization Water, saturated sodium bicarbonate aqueous solution, deionized water washing (washing to neutrality), oil reservoir obtain after being dried, filtered with anhydrous sodium sulfate To 11.6 kg of colorless oil phenylacetate, yield 85%, content 98.3%.
Embodiment 9
It is sequentially added in the first storage tank A deionized water (30 L), phenol (9.4kg, 100mol), and sodium hydroxide (4.4kg, 110 Mol) and stirring and dissolving is to clear, adds deionized water precise volume setting to 50 L, it is the water-soluble of 2.0 mol/L that phenol concentration, which is made, Liquid, sealing is stand-by after mixing evenly.Acetic anhydride 13.3kg(130 moL, density 1.08g/mL are added in the second storage tank B, mole Concentration 10.60mol/L) sealing is for use.
The material in the first storage tank A and the second storage tank B is delivered to (control after mixer is mixed respectively with metering pump Phenol: the molar flow ratio of acetic anhydride is 1:1.3), mixed liquor carries out esterification continuously into tubular reactor, and tubular type is anti- Temperature in device is answered to maintain 100 DEG C, mixed liquor residence time in tubular reactor is 2 minutes.It is flowed out in tubular reactor Feed liquid after esterification enters receiving tank, and stratification is oil reservoir and water layer, and liquid separation removes water layer, and oil reservoir successively uses deionization Water, saturated sodium bicarbonate aqueous solution, deionized water washing (washing to neutrality), oil reservoir obtain after being dried, filtered with anhydrous sodium sulfate To 8.7 kg of colorless oil phenylacetate, yield 64%, content 95.3%.
Content described in this specification is only to enumerate to inventive concept way of realization, and protection scope of the present invention is not answered When the concrete form for being seen as limited by embodiment and being stated.

Claims (6)

1. a kind of preparation method of phenylacetate class compound, it is characterised in that with fortified phenol and acetic acid as shown in formula (I) Acid anhydride is reaction raw materials, and using sodium hydrate aqueous solution as solvent, esterification is carried out in tubular reactor, and such as formula (II) is made Shown in phenylacetate class compound, reaction equation is as follows:
In formula (I) and formula (II), substituent R is the alkane of hydrogen, the alkyl of C1~C6, nitro, cyano, halogen, carboxyl or C1~C12 Oxygen carbonyl.
2. a kind of preparation method of phenylacetate class compound according to claim 1, it is characterised in that specifically include with Lower step: the fortified phenol as shown in formula (I) being dissolved in sodium hydrate aqueous solution and is placed in the first storage tank (A), acetic anhydride It is placed in the second storage tank (B)；Material in first storage tank (A) and the second storage tank (B) is conveyed through metering pump respectively, into mixer It is inside mixed, mixed liquor carries out esterification, the esterification flowed out in tubular reactor continuously into tubular reactor Feed liquid afterwards is post-treated, obtains target product phenylacetate class compound.
3. a kind of preparation method of phenylacetate class compound according to claim 2, it is characterised in that esterification Temperature is 5 ~ 100 DEG C, preferably 20 ~ 40 DEG C.
4. a kind of preparation method of phenylacetate class compound according to claim 2, it is characterised in that mixed liquor is in pipe Residence time in formula reactor is 0.5 ~ 60 minute, preferably 1 ~ 5 minute.
5. a kind of preparation method of phenylacetate class compound according to claim 2, it is characterised in that as shown in formula (I) Fortified phenol and sodium hydroxide molar ratio be 1:1.0 ~ 2.0.
6. a kind of preparation method of phenylacetate class compound according to claim 2, it is characterised in that the step of post-processing Suddenly are as follows: the feed liquid stratification after esterification is oil reservoir and water layer, and liquid separation removes water layer, and oil reservoir successively uses deionized water, satisfies It is washed with sodium bicarbonate aqueous solution, deionized water, washing to neutrality is dry, obtains target product phenylacetate class compound.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108129300A (en) * 2017-12-27 2018-06-08 浙江省衢州第二中学 A kind of novel preparation method of acetylsalicylic acid

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CN108129300A (en) * 2017-12-27 2018-06-08 浙江省衢州第二中学 A kind of novel preparation method of acetylsalicylic acid

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CN108129300A (en) * 2017-12-27 2018-06-08 浙江省衢州第二中学 A kind of novel preparation method of acetylsalicylic acid

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