CN104628592A - Method for directly synthesizing acetaminophen from nitrobenzene in acetic acid solution at one step - Google Patents
Method for directly synthesizing acetaminophen from nitrobenzene in acetic acid solution at one step Download PDFInfo
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Abstract
The invention discloses a method for directly synthesizing acetaminophen from nitrobenzene in an acetic acid solution at one step. The method comprises the following steps: I, putting a loaded type metal Pt catalyst together with solvent water, a zinc salt, an acetic acid, nitrobenzene and hexadecy ltrimethyl ammonium bromide into a high-pressure reaction kettle; II, introducing H2 into the reaction kettle at 80-200 DEG C to react for 3-40 hours; and III, feeding acetic anhydride into the reaction kettle through a feeding pump, filtering the hot reaction liquid, performing reduced pressure distillation to separate out crystal, and filtering, thereby obtaining a mixture of acetaminophen and a reaction byproduct acetanilide, further adding a solvent benzene, stirring for 30 minutes at 50-60 DEG C, filtering, and performing reduced pressure vacuum drying, thereby obtaining acetaminophen. By adopting the method, partial acylation of p-aminophenol can be simultaneously completed through the acetic acid in hydrogenation reaction, and the use amount of acetic anhydride can be reduced by about 70% at most.
Description
Technical field
The invention belongs to organic catalytic reaction field, specifically a kind of method of directly being synthesized acamol by oil of mirbane.
Background technology
Acamol (being called for short APAP), a kind of conventional antipyretic and analgesic (medicine name Paracetamol), have that pungency is little, the advantage such as rarely anaphylaxis, side effect are little, now become No.1 antipyretic and analgesic on world pharmaceutical market.In addition, medicine and some other organic synthetic intermediates such as it or Win-11450, also for the synthesis of the stablizer etc. of photosensitive medicine, hydrogen peroxide.
At present, industrial acamol is produced large is that raw material is made through acetic anhydride acylation mainly with p-aminophenol.Due to p-aminophenol very easily oxidation stain in production, transport transporting procedures, therefore first must refine p-aminophenol when preparing acamol, just can produce the former medicine of the acamol meeting standards of pharmacopoeia.Not only complex technical process, energy consumption is large, and p-aminophenol is refining and losing comparatively greatly in purification process, causes the total recovery of product low.Therefore, one-step technology raw material hydrogenating reduction and follow-up acylation process being incorporated in directly synthesis acamol in same reactor becomes the focus of current acamol study on the synthesis.The one-step synthesis method acamol of current reported in literature, be raw material mainly with p-NP greatly, though can realize the direct synthesis of acamol, raw materials cost is higher, uneconomical economically.Oil of mirbane is large industrial chemicals, has obviously raw material advantage with the production that it carries out p-aminophenol and acamol for starting raw material.Be that catalytic material synthesis p-aminophenol realizes suitability for industrialized production at present with oil of mirbane.This technique take generally Pt/C as catalyzer, carries out in the sulphuric acid soln of 10 ~ 20%.Because reaction is carried out in sulphuric acid soln, the p-aminophenol generated in reaction process and by product aniline all exist with the form of vitriol, and this just makes in hydrogenation reaction solution, directly carry out acylation reaction and has certain difficulty.The patent CN103113254 that this seminar had previously applied for discloses a kind of technique of directly synthesizing paracetamol in zinc solution from By Catalytic Hydrogenation of Nitrobenzene; first oil of mirbane be hydrogenated to p-aminophenol in zinc solution, and reaction solution adds acylating agent acetic anhydride after going out by product aniline by fractionation by distillation and obtains acamol.This technique instead of sulfuric acid for acid catalyzed rearrangement catalyzer with zinc salt; reconcile pH without the need to ammonia neutralization after reaction and directly can carry out acylation reaction; but hydrogenation and acidylate still proceed step by step, not only acylating agent acetic anhydride consumption energy consumption that is large but also aniline still-process is higher.The invention provides a kind of in acetic acid solution the method by the direct one-step synthesis acamol of oil of mirbane; hydrogenation reaction and acylation reaction are carried out simultaneously; acylating agent acetic anhydride consumption is few; product yield is high; by-product Acetanilide simultaneously, the separation method of acamol and Acetanilide is simple.
Summary of the invention
Technical problem to be solved by this invention is: provide a kind of method of directly being synthesized acamol in acetic acid solution by oil of mirbane one step, by adding acetic acid, utilize the collaborative promoter action of acetic acid and zinc salt, effectively improve yield and the selectivity of product, undoping under other promotor condition, total yield of products is more than 80%; Hydrogenation reaction is carried out in process, and it is partially acylated that acetic acid can complete p-aminophenol, diacetyl oxide consumption relatively substep acidylate is the highest reduces about 70%.The present invention can complete the acidylate by-product Acetanilide of hydrogenation side reaction product aniline simultaneously, and the separation method of acamol and Acetanilide is simple.
Technical scheme of the present invention is:
In acetic acid solution, oil of mirbane one step directly synthesizes a method for acamol, comprises the following steps:
The first step, load type metal Pt catalyzer and aqueous solvent, zinc salt, acetic acid, oil of mirbane and cetyl trimethylammonium bromide are put into autoclave, and its quality proportioning is load type metal Pt catalyzer: zinc salt: oil of mirbane: acetic acid: cetyl trimethylammonium bromide: water=0.05 ~ 1: 0.0 ~ 6:2 ~ 40:5 ~ 60: 0.02: 100;
Second step, in above-mentioned reactor, with N
2displaced air, after 8 ~ 12 minutes, passes into H at temperature 80 ~ 200 DEG C
2, to H
2dividing potential drop is 0.1 ~ 2.0MPa, 3 ~ 40 hours reaction times;
3rd step, after the reaction of second step terminates, reactor is down to 50 ~ 60 DEG C, squeezes into diacetyl oxide by charge pump in reactor, diacetyl oxide add-on is that the first step adds 20% ~ 80% of oil of mirbane molar weight, reacts 10 minutes;
4th step, after the reaction of the 3rd step terminates, while hot by reacting liquid filtering;
5th step, carries out underpressure distillation by the reaction solution after filtering, steams the solution of 50% ~ 70%, be cooled to 5 ~ 10 DEG C, crystallization, filter the mixture obtaining acamol and side reaction product Acetanilide;
6th step, be benzene in mass ratio in the acamol obtained to the 5th step and the mixture of side reaction product Acetanilide: solid mixture=2 ~ 3:1 adds solvent benzol, stir 30 minutes at 50 ~ 60 DEG C, filter also reduced vacuum drying and obtain acamol.
The composition of described supported Pt catalysts comprises the active ingredient Pt of carrier and load; Pt charge capacity is 0.1% ~ 5%.
Described supported Pt catalysts is preferably Pt/C, Pt/SiO
2, Pt/Al
2o
3or Pt/TiO
2.
Zinc salt recited above is zinc sulfate, zinc acetate, zinc chloride or zinc nitrate.
In the described the first step, the preferred amounts of zinc salt is zinc salt: water=1 ~ 5:100.
The invention has the beneficial effects as follows: the invention provides a kind of in acetic acid solution the technique by oil of mirbane one-step synthesis acamol, acetic acid can complete the partially acylated of p-aminophenol in hydrogenation reaction simultaneously, compare the substep acidylate of CN103113254, the consumption of diacetyl oxide can reduce about 70% at most; Acetic acid and zinc salt involutory become p-aminophenol react and have good collaborative promoter action, in the mixing solutions of acetic acid and zinc salt, the yield of acamol is up to 82.3%.The acidylate of by product aniline can be completed in reaction process simultaneously, obtain Acetanilide.Utilize solvent benzol to dissolve Acetanilide, being effectively separated of Acetanilide and acamol can be realized.The synthesis technique of this acamol, method is simple, and product yield is high, and reaction solution can be recycled, without discharging of waste liquid.
Embodiment
Further illustrate the present invention with embodiment below, embodiment, only for describing the present invention in detail, is not considered as the restriction to the claims in the present invention protection domain.
The load type metal Pt catalyzer that the present invention relates to is well known materials, is prepared from, as Pt/C, Pt/SiO for being carried on conventional various carrier by dipping method by Platinic chloride
2, Pt/Al
2o
3, Pt/TiO
2deng.Pt charge capacity is 0.1% ~ 5% (wt%).Embodiment 1
0.1gPt charge capacity is the Pt/SiO of 5% (wt%) by the first step
2catalyzer, 20g (0.163mol) oil of mirbane, 60g acetic acid, 0.02g cetyl trimethylammonium bromide and 100ml water put into autoclave;
Second step, in above-mentioned autoclave, with N
2displaced air, after 8 ~ 12 minutes, is heated to 150 DEG C and passes into H
2, be 0.5MPa to hydrogen partial pressure, react 10 hours, make oil of mirbane be converted into p-aminophenol and acamol;
3rd step, after the reaction of second step terminates, is down to 50 ~ 60 DEG C, squeezes into 6.4g (0.063mol) diacetyl oxide by charge pump in reactor, react 10 minutes by reactor.
4th step, after the reaction of the 3rd step terminates, while hot by reacting liquid filtering, obtains filtrate 165ml;
5th step, carries out underpressure distillation and is about 50ml by the reaction solution after filtering to amount of solution, be cooled to 5 ~ 10 DEG C, crystallization, filters to obtain the mixture of acamol and side reaction product Acetanilide;
6th step, in the acamol obtained to the 5th step and the mixture of side reaction product Acetanilide in mass ratio for (benzene: solid mixture) for 2:1 adds solvent benzol, stir 30 minutes at 60 DEG C, to filter and reduced vacuum dry cake obtains acamol, acamol yield be 45.7% (mole number of the raw material oil of mirbane that the mole number/the first step of the acamol obtained after acamol yield=drying adds).
Embodiment 2
1.0g Pt charge capacity is the Pt/Al of 0.1% (wt%) by the first step
2o
3catalyzer, 5g (0.041mol) oil of mirbane, 0.1g zinc sulfate, 5g acetic acid, 0.02g cetyl trimethylammonium bromide and 100ml water put into autoclave;
Second step, in above-mentioned autoclave, with N
2displaced air, after 8 ~ 12 minutes, is heated to 100 DEG C and passes into H
2, be 1.0MPa to hydrogen partial pressure, react 4 hours, make oil of mirbane be converted into p-aminophenol and acamol;
3rd step, after the reaction of second step terminates, is down to 50 ~ 60 DEG C, squeezes into 3.3g (0.032mol) diacetyl oxide by charge pump in reactor, react 10 minutes by reactor.
4th step, after the reaction of the 3rd step terminates, while hot by reacting liquid filtering, obtains filtrate 106ml;
5th step, carries out underpressure distillation and is about 50ml by the reaction solution after filtering to amount of solution, be cooled to 5 ~ 10 DEG C, crystallization, filters to obtain the mixture of acamol and side reaction product Acetanilide;
6th step, in the acamol obtained to the 5th step and the mixture of side reaction product Acetanilide in mass ratio for (benzene: solid mixture) for 2:1 adds solvent benzol, stir 30 minutes at 60 DEG C, filter also reduced vacuum dry cake and obtain acamol, acamol yield is 49.2%.
Embodiment 3
0.5gPt charge capacity is the Pt/TiO of 1% (wt%) by the first step
2catalyzer, 20g (0.163mol) oil of mirbane, 5g zinc nitrate, 40g acetic acid, 0.02g cetyl trimethylammonium bromide and 100ml water put into autoclave;
Second step, in above-mentioned autoclave, with N
2displaced air, after 8 ~ 12 minutes, is heated to 120 DEG C and passes into H
2, be 1.0MPa to hydrogen partial pressure, react 12 hours, make oil of mirbane be converted into p-aminophenol and acamol;
3rd step, after the reaction of second step terminates, is down to 50 ~ 60 DEG C, squeezes into 8.3g (0.0813) diacetyl oxide by charge pump in reactor, react 10 minutes by reactor.
4th step, after the reaction of the 3rd step terminates, while hot by reacting liquid filtering, obtains filtrate 143ml;
5th step, carries out underpressure distillation and is about 50ml by the reaction solution after filtering to amount of solution, be cooled to 5 ~ 10 DEG C, crystallization, filters to obtain the mixture of acamol and side reaction product Acetanilide;
6th step, in the acamol obtained to the 5th step and the mixture of side reaction product Acetanilide in mass ratio for (benzene: solid mixture) for 2:1 adds solvent benzol, stir 30 minutes at 60 DEG C, filter also reduced vacuum dry cake and obtain acamol, acamol yield is 70.1%.
Embodiment 4
0.5gPt charge capacity is that the Pt/C catalyzer of 0.5% (wt%), 40g (0.325mol) oil of mirbane, 5g zinc acetate, 40g acetic acid, 0.02g cetyl trimethylammonium bromide and 100ml water put into autoclave by the first step;
Second step, in above-mentioned autoclave, with N
2displaced air, after 8 ~ 12 minutes, is heated to 150 DEG C and passes into H
2, be 0.5MPa to hydrogen partial pressure, react 30 hours, make oil of mirbane be converted into p-aminophenol and acamol;
3rd step, after the reaction of second step terminates, is down to 50 ~ 60 DEG C, squeezes into 8.2g (0.080mol) diacetyl oxide by charge pump in reactor, react 10 minutes by reactor.
4th step, after the reaction of the 3rd step terminates, while hot by reacting liquid filtering, obtains filtrate 146ml;
5th step, carries out underpressure distillation and is about 50ml by the reaction solution after filtering to amount of solution, be cooled to 5 ~ 10 DEG C, crystallization, filters to obtain the mixture of acamol and side reaction product Acetanilide;
6th step, in the acamol obtained to the 5th step and the mixture of side reaction product Acetanilide in mass ratio for (benzene: solid mixture) for 2:1 adds solvent benzol, stir 30 minutes at 60 DEG C, filter also reduced vacuum dry cake and obtain acamol, acamol yield is 75.1%.
Embodiment 5
0.5gPt charge capacity is the Pt/TiO of 0.2% (wt%) by the first step
2catalyzer, 20g (0.163mol) oil of mirbane, 3g zinc chloride, 20g acetic acid, 0.02g cetyl trimethylammonium bromide and 100ml water put into autoclave;
Second step, in above-mentioned autoclave, with N
2displaced air, after 8 ~ 12 minutes, is heated to 200 DEG C and passes into H
2, be 0.1MPa to hydrogen partial pressure, react 20 hours, make oil of mirbane be converted into p-aminophenol and acamol;
3rd step, after the reaction of second step terminates, is down to 50 ~ 60 DEG C, squeezes into 3.6g (0.035mol) diacetyl oxide by charge pump in reactor, react 10 minutes by reactor.
4th step, after the reaction of the 3rd step terminates, while hot by reacting liquid filtering, obtains filtrate 122mL;
5th step, carries out underpressure distillation and is about 50ml by the reaction solution after filtering to amount of solution, be cooled to 5 ~ 10 DEG C, crystallization, filters to obtain the mixture of acamol and side reaction product Acetanilide;
6th step, in the acamol obtained to the 5th step and the mixture of side reaction product Acetanilide in mass ratio for (benzene: solid mixture) for 2:1 adds solvent benzol, stir 30 minutes at 60 DEG C, filter also reduced vacuum dry cake and obtain acamol, acamol yield is 72.3%.
Embodiment 6
The first step, add in autoclave together with the distillate that the Pt/C catalyzer obtained after embodiment 4 the 4th step being filtered and the 5th step obtain and crystalline mother solution, and in still, add 40g (0.325mol) oil of mirbane and 0.02g cetyl trimethylammonium bromide;
Second step, in above-mentioned autoclave, with N
2displaced air, after 8 ~ 12 minutes, is heated to 150 DEG C and passes into H
2, be 0.5MPa to hydrogen partial pressure, react 30 hours, make oil of mirbane be converted into p-aminophenol and acamol;
3rd step, after the reaction of second step terminates, is down to 60 DEG C, squeezes into 8.2g (0.080mol) diacetyl oxide by charge pump in reactor, react 10 minutes by reactor.
4th step, after the reaction of the 3rd step terminates, while hot by reacting liquid filtering, obtains filtrate 146ml;
5th step, carries out underpressure distillation and is about 50ml by the reaction solution after filtering to amount of solution, be cooled to 10 ~ 20 DEG C, crystallization, filters to obtain the mixture of acamol and side reaction product Acetanilide;
6th step, in the acamol obtained to the 5th step and the mixture of side reaction product Acetanilide in mass ratio for (benzene: solid mixture) for 2:1 adds solvent benzol, stir 30 minutes at 60 DEG C, filter also reduced vacuum dry cake and obtain acamol, acamol yield is 82.3%.
The load type metal Pt catalyzer used in above-mentioned whole embodiment, can be prepared by existing known technology.As just having specific descriptions in Chinese patent CN1270821C.
The present invention does not address part and is applicable to prior art.
Claims (5)
1. in acetic acid solution, oil of mirbane one step directly synthesizes a method for acamol, it is characterized by and comprises the following steps:
The first step, load type metal Pt catalyzer and aqueous solvent, zinc salt, acetic acid, oil of mirbane and cetyl trimethylammonium bromide are put into autoclave, and its quality proportioning is load type metal Pt catalyzer: zinc salt: oil of mirbane: acetic acid: cetyl trimethylammonium bromide: water=0.05 ~ 1: 0.0 ~ 6:2 ~ 40:5 ~ 60: 0.02: 100;
Second step, in above-mentioned reactor, with N
2displaced air is after 8 ~ 12 minutes, in temperature 80 ~ 200
oh is passed under C
2, to H
2dividing potential drop is 0.1 ~ 2.0MPa, 3 ~ 40 hours reaction times;
3rd step, after the reaction of second step terminates, is cooled to 50 ~ 60 by reactor
oc, squeezes into diacetyl oxide by charge pump in reactor, and diacetyl oxide add-on is that second step adds 20% ~ 80% of oil of mirbane molar weight, reacts 10 minutes;
4th step, after the reaction of the 3rd step terminates, while hot by reacting liquid filtering;
5th step, carries out underpressure distillation by the reaction solution after filtering, steams the solution of 50% ~ 70%, be cooled to 5 ~ 10
oc, crystallization, filters the mixture obtaining acamol and side reaction product Acetanilide;
6th step is benzene in the acamol obtained to the 5th step and the mixture of side reaction product Acetanilide: solid mixture=2 ~ 3:1 adds solvent benzol, 50 ~ 60 in mass ratio
oc stirs 30 minutes, filters also reduced vacuum drying and obtains acamol.
2. as claimed in claim 1 a kind of in acetic acid solution oil of mirbane one step directly synthesize the method for acamol, the composition that it is characterized by described supported Pt catalysts comprises the active ingredient Pt of carrier and load; Pt charge capacity is 0.1% ~ 5%(wt%).
3. as claimed in claim 1 a kind of in acetic acid solution oil of mirbane one step directly synthesize the method for acamol, it is characterized by described supported Pt catalysts and be preferably Pt/C, Pt/SiO
2, Pt/Al
2o
3or Pt/TiO
2.
4. as claimed in claim 1 a kind of in acetic acid solution oil of mirbane one step directly synthesize the method for acamol, it is characterized by described zinc salt is zinc sulfate, zinc acetate, zinc chloride or zinc nitrate.
5. as claimed in claim 1 a kind of in acetic acid solution oil of mirbane one step directly synthesize the method for acamol, the preferred amounts that it is characterized by zinc salt in the described the first step is zinc salt: water=1 ~ 5:100.
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Cited By (1)
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|---|---|---|---|---|
| WO2021235335A1 (en) * | 2020-05-18 | 2021-11-25 | 株式会社エーピーアイ コーポレーション | Method for producing acetaminophen |
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