CN113735723B - Preparation method of N- (1, 3-dimethylbutyl) -N' -phenyl p-benzoquinone - Google Patents
Preparation method of N- (1, 3-dimethylbutyl) -N' -phenyl p-benzoquinone Download PDFInfo
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Abstract
The invention discloses a preparation method of N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone. The method comprises the following steps: p-benzoquinone reacts with aniline to obtain p-benzoquinone-2-aniline; the p-benzoquinone-2-aniline and 1, 3-dimethylbutylamine react to obtain N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone. The invention adopts the continuous oxidation addition reaction of the p-benzoquinone, the aniline and the 1, 3-dimethylbutylamine, realizes the simple and efficient preparation of 6 ppd-quinone under the mild condition. Compared with the traditional ozone catalytic method, the method has the advantages of higher conversion efficiency, better economic applicability, environmental friendliness and the like, and is suitable for industrial production and technical conversion. The 6 ppd-quinone prepared by the method can be widely used in content detection of environmental samples and related researches such as cell and animal toxicology experiments and the like as a standard substance.
Description
Technical Field
The invention relates to the field of environmental analysis, in particular to a preparation method of N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone (6 ppd-quinone).
Background
6ppd, namely N- (1, 3-dimethylbutyl) -N' -phenyl-p-phenylenediamine with CAS number 793-24-8, is a commonly used rubber anti-aging agent in the chemical industry. The compound has better oxidation resistance and ozone resistance, and is widely applied to the rubber industry for improving the high-temperature fatigue resistance and the deflection resistance of tires at present. According to statistics, the tyre of each household car contains about 6ppd of 140-; and a heavy truck tire may have a 6ppd content as high as 3600-. As the tire wears and ages, 6ppd can enter the environment with tire debris. Existing studies have shown the presence of different concentrations of 6ppd in different environmental media, including soil, lakes, municipal runoff and atmospheric dust. However, due to the low biotoxicity of 6ppd, the widespread presence in nature has not received sufficient attention for a long time.
In 1 month 2021, a Science article indicates that 6ppd generates an oxidation product N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone, namely 6 ppd-quinone, in a natural environment through catalysis of light and ozone, and has extremely strong biological toxicity; the generation mechanism and the molecular structural formula of the compound are shown in figure 1. The study confirmed that 6 ppd-quinone can enter urban runoff along with rain wash and cause a great amount of deaths of migratory silver salmon in multiple areas such as the pacific west coast. The comparative data show that 6 ppd-quinone has a median lethal dose of 0.8-1.5 mug/L for silver salmon, well below the median lethal dose of 6ppd (250 + -60 mug/L) for its parent. In addition, the research shows that 6 ppd-quinone has high chemical stability, and the biotoxicity of the quinone is not obviously reduced even under long-time high-temperature heating conditions (80 ℃, 72 hours).
The above phenomena have attracted a great deal of attention from environmental and toxicological scientists in various countries of the world. The subsequent content determination, biological toxicity detection and human health risk assessment of the substance in different environment media become research hotspots in the years from now on. However, the core problem in carrying out the above studies is the lack of a simple and efficient method for preparing 6 ppd-quinone analytical standards. In the above-mentioned Science article, the authors catalyzed a technical grade of 6ppd powder by means of uv irradiation and ozone passage to convert a portion of the 6ppd to 6 ppd-quinone, which was subsequently separated and purified by means of acid washing and multiple column separation techniques (including ion exchange chromatography, C18 solid phase extraction column and preparative high performance liquid chromatography) to give a 6 ppd-quinone standard. The method has the defects of low conversion efficiency, high cost, environmental friendliness and the like, and is not suitable for industrial production.
Accordingly, the prior art is yet to be improved and developed.
Disclosure of Invention
In view of the above-mentioned disadvantages of the prior art, the present invention aims to provide a method for preparing N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone (6 ppd-quinone), which aims to solve the problem of the lack of a method for simply and efficiently preparing a 6 ppd-quinone standard product.
The technical scheme of the invention is as follows:
a preparation method of N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone comprises the following steps:
p-benzoquinone reacts with aniline to obtain p-benzoquinone-2-aniline;
the p-benzoquinone-2-aniline and 1, 3-dimethylbutylamine react to obtain N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone.
Optionally, the p-benzoquinone is reacted with aniline in an aqueous solvent.
Optionally, the temperature for the reaction of the p-benzoquinone and the aniline is 50-60 ℃, and the reaction time is 20-40 minutes.
Alternatively, the p-benzoquinone is reacted with aniline in a molar ratio (2-2.4): 1.
Optionally, the p-benzoquinone-2-aniline and 1, 3-dimethylbutylamine are reacted in a methanol aqueous solution or an ethanol aqueous solution, wherein the volume fraction of methanol in the methanol aqueous solution is 90% -100%, and the volume fraction of ethanol in the ethanol aqueous solution is 90% -100%.
Optionally, the temperature for the reaction of the p-benzoquinone-2-aniline and the 1, 3-dimethylbutylamine is room temperature, and the reaction time is 3.5-4.5 h.
Alternatively, the p-benzoquinone-2-aniline and 1, 3-dimethylbutylamine are reacted in a molar ratio of (2-2.4): 1.
Optionally, after the reaction of the p-benzoquinone-2-aniline and 1, 3-dimethylbutylamine is completed, the method further comprises the following steps: and (3) subjecting the reacted system to silica gel column chromatography separation or recrystallization treatment to obtain the N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone.
Optionally, the step of reacting p-benzoquinone with aniline to obtain p-benzoquinone-2-aniline specifically comprises:
dissolving p-benzoquinone and aniline in a water solvent to obtain a first reaction solution;
adding acid into the first reaction solution until the pH value is 6.5-7.0, and reacting to obtain the p-benzoquinone-2-aniline;
and/or the step of reacting the p-benzoquinone-2-aniline with 1, 3-dimethylbutylamine to obtain N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone specifically comprises the following steps:
dissolving p-benzoquinone-2-aniline in methanol water solution or ethanol water solution, and then adding acid until the pH value is 6.5-7.0 to obtain a second reaction solution;
and adding 1, 3-dimethylbutylamine into the second reaction solution for reaction to obtain the N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone.
A preparation method of N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone comprises the following steps:
p-benzoquinone reacts with 1, 3-dimethylbutylamine to obtain N- (1, 3-dimethylbutyl) -p-benzoquinone;
and reacting the N- (1, 3-dimethylbutyl) -p-benzoquinone with aniline to obtain the N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone.
Has the advantages that: the invention adopts the continuous oxidation addition reaction of the p-benzoquinone, the aniline and the 1, 3-dimethylbutylamine, realizes the simple and efficient preparation of 6 ppd-quinone under the mild condition. Compared with the traditional ozone catalytic method, the method has the advantages of higher conversion efficiency, better economic applicability, environmental friendliness and the like, and is suitable for industrial production and technical conversion. The 6 ppd-quinone prepared by the method can be widely used in content detection of environmental samples and related researches such as cell and animal toxicology experiments and the like as a standard substance.
Drawings
FIG. 1 is a schematic representation of the oxidation of 6ppd in the environment by light and ozone to 6 ppd-quinone.
FIG. 2 is a schematic diagram of a preparation route of 6 ppd-quinone provided in the examples of the present invention.
FIG. 3 is a liquid chromatogram of p-benzoquinone-2-aniline (top) and 6 ppd-quinone (bottom) according to a specific example of the present invention.
FIG. 4 is a mass spectrum secondary fragment pattern of p-benzoquinone-2-aniline (top) and 6 ppd-quinone (bottom) in a specific example of the present invention.
Detailed Description
The present invention provides a method for producing N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone (6 ppd-quinone), and the present invention will be described in further detail below in order to make the objects, technical aspects and effects of the present invention clearer and clearer. It should be understood that the specific embodiments described herein are merely illustrative of the invention and do not limit the invention.
N- (1, 3-dimethylbutyl) -N '-phenyl-p-benzoquinone (6 ppd-quinone) is an oxidation product of ozone and light catalysis of tire antioxidant N- (1, 3-dimethylbutyl) -N' -phenyl-p-phenylenediamine (6ppd), which enters and remains in various environmental media as tires wear and age. Recent studies found that 6 ppd-quinone in the environment has a high biotoxicity, and its presence can cause a great number of deaths of migratory silver salmon in many areas such as the west coast of the pacific. However, the lack of a simple and efficient method for preparing the 6 ppd-quinone standard substance greatly limits the extensive research of the compound.
Accordingly, an embodiment of the present invention provides a method for preparing N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone, which includes the steps of:
s1, reacting p-benzoquinone with aniline to obtain p-benzoquinone-2-aniline;
s2, reacting the p-benzoquinone-2-aniline with 1, 3-dimethylbutylamine to obtain N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone.
This example provides a simple, efficient method for preparing 6 ppd-quinone. The 6 ppd-quinone is prepared by adopting the continuous oxidation addition reaction of p-benzoquinone, aniline and 1, 3-dimethylbutylamine, and the specific preparation route is shown in figure 2: firstly, p-benzoquinone and aniline are subjected to oxidation addition reaction to generate p-benzoquinone-2-aniline; this material was then subjected to an oxidative addition reaction with 1, 3-dimethylbutylamine to yield the 6 ppd-quinone without purification. The preparation method has the advantages of simple steps, mild reaction conditions, easiness in operation, higher economical efficiency and applicability, high conversion efficiency, environmental friendliness and the like. The 6 ppd-quinone standard substance prepared by the method can be widely used for content determination of environmental samples and related researches such as cell and animal toxicology experiments and the like.
In step S1, in one embodiment, the p-benzoquinone is reacted with aniline in an aqueous solvent. The preparation method of the embodiment has high economical efficiency and applicability by using water as a reaction solvent.
In one embodiment, the p-benzoquinone is reacted with aniline at a temperature of 50 to 60 deg.C (e.g., 55 deg.C) for a time period of 20 to 40 minutes (e.g., 30 minutes).
In one embodiment, the p-benzoquinone is reacted with aniline in a molar ratio of (2-2.4):1, such as in a molar ratio of 2: 1.
In one embodiment, the step of reacting p-benzoquinone with aniline to obtain p-benzoquinone-2-aniline comprises:
dissolving p-benzoquinone and aniline in a water solvent to obtain a first reaction solution;
adding acid (such as glacial acetic acid, hydrochloric acid and the like) into the first reaction solution until the pH value is between 6.5 and 7.0, and reacting to obtain the p-benzoquinone-2-aniline.
Because aniline has strong nucleophilicity and has high activity in reaction with p-benzoquinone, if not controlled, a polysubstituted byproduct of benzoquinone and amine substances is generated; in this example, the pH of the reaction is adjusted by adding a specific proportion of acid, and the nucleophilicity of aniline is changed, so as to control the reaction rate, reduce side reactions, and improve the yield.
In step S2, in one embodiment, the p-benzoquinone-2-aniline and 1, 3-dimethylbutylamine are reacted in an aqueous methanol solution or an aqueous ethanol solution. The methanol water solution or the ethanol water solution is used as a reaction solvent, so that the economical efficiency and the applicability of the preparation method of the embodiment are further ensured. Further, the methanol is 90% to 100% (e.g., 95%) by volume of the aqueous methanol solution, and the ethanol is 90% to 100% (e.g., 95%) by volume of the aqueous ethanol solution.
In one embodiment, the reaction of p-benzoquinone-2-aniline with 1, 3-dimethylbutylamine is carried out at room temperature (referred to as 16-25 ℃) for 3.5-4.5h (e.g., 4 h).
In one embodiment, the p-benzoquinone-2-aniline and 1, 3-dimethylbutylamine are reacted in a molar ratio of (2-2.4):1, such as a molar ratio of 2: 1.
In one embodiment, the method further comprises the following steps after the reaction of the p-benzoquinone-2-aniline and the 1, 3-dimethylbutylamine is completed: and (3) subjecting the reacted system to silica gel column chromatography separation or recrystallization treatment to obtain the N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone.
In one embodiment, the step of reacting p-benzoquinone-2-aniline with 1, 3-dimethylbutylamine to obtain N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone comprises:
dissolving p-benzoquinone-2-aniline in methanol water solution or ethanol water solution, and adding acid (such as glacial acetic acid, hydrochloric acid, etc.) until pH is 6.5-7.0 to obtain second reaction solution;
and adding 1, 3-dimethylbutylamine into the second reaction solution for reaction to obtain the N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone.
Specifically, the 1, 3-dimethylbutylamine has strong nucleophilicity, has high activity of reacting with p-benzoquinone-2-aniline, and generates a by-product with multiple substitution of p-benzoquinone and amine substances if not controlled; in this example, the pH of the reaction is adjusted by adding a specific proportion of acid, and the nucleophilicity of the 1, 3-dimethylbutylamine compound is changed, so that the effects of controlling the reaction rate, reducing side reactions and improving the yield are achieved.
In the embodiment, the continuous oxidation addition reaction of p-benzoquinone, aniline and 1, 3-butanediamine is utilized, so that the method is simple and efficient, and can be used for preparing 6 ppd-quinone under mild conditions. In addition, the present example optimizes the reaction material ratio and the solvent used, and utilizes the addition of glacial acetic acid with a specific ratio to adjust and control the pH of the reaction, thereby inhibiting the occurrence of side reactions and improving the reaction yield. Compared with the traditional ozone catalytic method, the method has the advantages of higher conversion efficiency, better economic applicability, environmental friendliness and the like, and is suitable for industrial production and technical conversion.
The embodiment of the invention also provides a preparation method of the N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone, which comprises the following steps:
s1', p-benzoquinone reacts with 1, 3-dimethylbutylamine to obtain N- (1, 3-dimethylbutyl) -p-benzoquinone;
s2', the N- (1, 3-dimethylbutyl) -p-benzoquinone and aniline react to obtain the N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone.
This example provides a simple, efficient method for preparing 6 ppd-quinone. The method adopts the continuous oxidation addition reaction of p-benzoquinone, 1, 3-dimethylbutylamine and aniline to prepare 6 ppd-quinone, and the specific preparation route is as follows: firstly, p-benzoquinone and 1, 3-dimethylbutylamine undergo an oxidation addition reaction to generate N- (1, 3-dimethylbutyl) -p-benzoquinone; the material was then subjected to an oxidative addition reaction with aniline to produce the 6 ppd-quinone without purification. The preparation method has the advantages of simple steps, mild reaction conditions, easy operation, and high economy and applicability. The 6 ppd-quinone standard substance prepared by the method can be widely used for content determination of environmental samples and related researches such as cell and animal toxicology experiments and the like.
Compared with the method of the embodiment, the method of the embodiment mainly has the following differences: the feeding amount ratio of the aniline and the 1, 3-dimethylbutylamine is different. In the above example process, the molar ratio of aniline to 1, 3-dimethylbutylamine charge was 2: 1; in this example, the molar ratio of aniline to 1, 3-dimethylbutylamine was 1: 2. the above example method has higher economic applicability in view of the lower price of aniline.
In one embodiment, the p-benzoquinone is reacted with 1, 3-dimethylbutylamine in a molar ratio (2-2.4):1, such as in a molar ratio of 2: 1;
the N- (1, 3-dimethylbutyl) -p-benzoquinone is reacted with aniline in a molar ratio of (2-2.4):1, for example in a molar ratio of 2: 1.
The invention is further illustrated by the following specific examples.
The procedure for the preparation of 6 ppd-quinone of this example is as follows:
1. preparation of p-benzoquinone-2-aniline
1.08 g of p-benzoquinone (10mmol) and 50 ml of deionized water are added into a 100 ml round bottom reaction flask, and then the reaction flask is placed in a water bath kettle at 55 ℃ and stirred at a constant speed until the raw materials are completely dissolved to obtain a p-benzoquinone aqueous solution. 455 microliters of aniline (5mmol) was dissolved in 15 milliliters of water and then added dropwise to the aqueous p-benzoquinone solution over a period of 5 minutes. Subsequently, 100. mu.l of glacial acetic acid was added to the reaction solution to adjust the pH of the reaction solution to 7.0. The reaction was kept at 55 ℃ with constant stirring for 30 minutes. After the reaction was completed, the reaction solution was suction-filtered, and the obtained solid was washed with hot water at 55 ℃ and an aqueous ethanol solution of 10% by volume fraction. The product was dried to give 1.85 g (9.29mmol) of reddish brown p-benzoquinone-2-aniline powder in 93% yield.
The product was examined by nmr and the data was as follows:1H NMR(400MHz,DMSO-d6):δ9.01(s,1H),7.18-7.42(m,5H),6.82(d,J＝10.4Hz,1H),6.71(dd,J＝10.4,2.4Hz,1H),5.88(d,J＝2.4Hz,1H).13c NMR (400MHz, DMSO-d6): delta 185.9,183.7,144.4,138.8,138.0,133.2,129.3,125.0,123.2, 99.6. The infrared spectrum data are as follows: 3227, 1676, 1631, 1570, 1518, 1497, 1449, 1285, 1080, 867, 861, 731, 696, 615, 508cm–1(ii) a Benzoquinone-2-aniline [ C ] protonated by hydrogen in positive ion mode of high-resolution mass spectrum12H10NO2]+200.0706, found 200.0703.
2.6 preparation of ppd-quinone
398 mg of p-benzoquinone-2-aniline (2mmol) is weighed and placed in a 25 ml round-bottom flask, 10 ml of 95% methanol water solution is added, and the mixture is stirred at a constant speed at room temperature until the solid is completely dissolved, so that a p-benzoquinone-2-aniline solution is obtained. Then, 80. mu.l of glacial acetic acid was added to the p-benzoquinone-2-aniline solution to adjust the pH to 6.5. 101 mg of 1, 3-dimethylbutylamine (1mmol) were subsequently dissolved in 5 ml of methanol and added dropwise to the p-benzoquinone-2-aniline solution. The reaction solution was kept under constant stirring at room temperature and the progress of the reaction was monitored by thin layer silica gel chromatography. After four hours the reaction was complete, the reaction solvent was distilled off under reduced pressure and the resulting crude product was passed through a silica gel column and eluted with n-hexane-dichloromethane eluent (v: v ═ 1: 1). The eluent was evaporated to give 454 mg of N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone, i.e. 6 ppd-quinone, in 76% yield.
The product was examined by nmr and the data was as follows:1H NMR(400MHz,CDCl3):δ8.22(s,1H),7.40(t,J＝7.8Hz,2H),7.23(m,3H),6.39(d,J＝8.0Hz,1H),5.97(s,1H),5.43(s,1H),3.55(m,1H),1.67(m,1H),1.53(m,1H),1.38(m,1H),1.22(d,J＝6.4Hz,3H),0.94(d,J＝6.4Hz,3H),0.91(d,J＝6.4Hz,3H).13C NMR(400MHz,CDCl3) Delta 180.1,178.5,149.6,147.7,137.4,129.7,126.1,122.8,95.7,92.8,46.8,45.6,25.2,22.7,20.2. the infrared spectral data are as follows: 3268,3232,2959,1640,1558,1489,1445,1355,1290,1266,829,731,694,514cm–1(ii) a High (a)6 ppd-quinone [ C ] protonated by hydrogen in positive ion mode of resolution mass spectrometry18H23N2O2]+The theoretical value of (A) is 299.1754, and the actual value is 299.1747.
3. Characterization of 6 ppd-quinone and p-benzoquinone-2-aniline by high performance liquid chromatography-high resolution mass spectrometry
The 6 ppd-quinone and the intermediate p-benzoquinone-2-aniline prepared in the reaction are characterized by ultra-high performance liquid chromatography-high resolution mass spectrometry. The chromatographic column used was an ACQUITY HSS T3(100 mm. times.2.1 mm,1.8 μm) chromatographic column with a flow rate of 0.3 ml/min; the mobile phase was 0.1% by volume formic acid/water (phase a) and 0.1% by volume acetonitrile (phase B). The mobile phase gradient was: 0-1 min, 2% B; 1-19 minutes, 2% B-100% B; 19-21 minutes, 100% B; 21-21.1 minutes, 100% B-12% B; 21.1-25 min, 2% B. As a result, as shown in FIG. 3, the peak production times of p-benzoquinone-2-aniline and 6 ppd-quinone were 11.06 and 15.76 minutes, respectively, and the peak production times were consistent with the molecular polarities thereof. In addition, the second mass spectral fragments of 6 ppd-quinone and p-benzoquinone-2-aniline were characterized using high resolution mass spectrometry equipped with an electrospray ion source. The mode is positive ion mode, and the collision energy is 10, 20 and 40eV superposition. FIG. 4 shows the secondary fragments and corresponding structural assignments of 6 ppd-quinone and p-benzoquinone-2-aniline. Wherein 299.1747 and 200.0703 correspond to the parent ion peaks of 6 ppd-quinone and p-benzoquinone-2-aniline, i.e. [ C ]12H10NO2]+And [ C12H10NO2]+. Characteristic ion fragments of p-benzoquinone-2-aniline are 183.0676, 172.0754, 154.0649 and 144.0806; while the characteristic ion fragments of 6 ppd-quinone are 256.1201, 215.0812, 241.0966, 187.0863 and 172.0754. The above results confirm the successful preparation of p-benzoquinone-2-aniline and 6 ppd-quinone and the feasibility of the above preparation route.
In conclusion, the invention provides a simple and efficient method for preparing 6 ppd-quinone. The specific preparation route is as follows: firstly, p-benzoquinone and aniline are subjected to oxidation addition reaction to generate p-benzoquinone-2-aniline. This material was then reacted with 1, 3-dimethylbutylamine to produce the 6 ppd-quinone without purification. The preparation method has the advantages of simple steps, mild reaction conditions and easy operation. The reaction solvents used can be water and methanol aqueous solution respectively, and the method has high economy and applicability. The 6 ppd-quinone standard substance prepared by the method can be widely used for content determination of environmental samples and related researches such as cell and animal toxicology experiments and the like.
It is to be understood that the invention is not limited to the examples described above, but that modifications and variations may be effected thereto by those of ordinary skill in the art in light of the foregoing description, and that all such modifications and variations are intended to be within the scope of the invention as defined by the appended claims.
Claims (7)
1. A preparation method of N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone is characterized by comprising the following steps:
p-benzoquinone reacts with aniline to obtain p-benzoquinone-2-aniline;
the p-benzoquinone-2-aniline and 1, 3-dimethylbutylamine react to obtain N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone;
the structural formula of the N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone is shown as follows:
the temperature for the reaction of the p-benzoquinone and the aniline is 50-60 ℃;
the method for preparing the p-benzoquinone-2-aniline comprises the following steps of:
dissolving p-benzoquinone and aniline in a water solvent to obtain a first reaction solution;
adding acid into the first reaction solution until the pH value is 6.5-7.0, and reacting to obtain the p-benzoquinone-2-aniline;
the step of reacting the p-benzoquinone-2-aniline with 1, 3-dimethylbutylamine to obtain N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone specifically comprises the following steps:
dissolving p-benzoquinone-2-aniline in methanol water solution or ethanol water solution, and then adding acid until the pH value is 6.5-7.0 to obtain a second reaction solution;
and adding 1, 3-dimethylbutylamine into the second reaction solution for reaction to obtain the N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone.
2. The process for preparing N- (1, 3-dimethylbutyl) -N' -phenylbenzoquinone according to claim 1, wherein the reaction time of p-benzoquinone with aniline is 20 to 40 minutes.
3. The process for producing N- (1, 3-dimethylbutyl) -N' -phenylphthaloquinone according to claim 1, wherein p-benzoquinone is reacted with aniline in a molar ratio of (2-2.4): 1.
4. The method for preparing N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone according to claim 1, wherein the methanol is present in an amount of 90% to 100% by volume in an aqueous solution of methanol, and the ethanol is present in an amount of 90% to 100% by volume in an aqueous solution of ethanol.
5. The process for preparing N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone according to claim 1, wherein the reaction temperature of p-benzoquinone-2-aniline with 1, 3-dimethylbutylamine is room temperature and the reaction time is 3.5-4.5 h.
6. The process for preparing N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone according to claim 1, wherein p-benzoquinone-2-aniline is reacted with 1, 3-dimethylbutylamine in a molar ratio of (2-2.4): 1.
7. The method for preparing N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone according to claim 1, wherein the reaction between p-benzoquinone-2-aniline and 1, 3-dimethylbutylamine is completed, and further comprising the steps of: and (3) subjecting the reacted system to silica gel column chromatography separation or recrystallization treatment to obtain the N- (1, 3-dimethylbutyl) -N' -phenyl-p-benzoquinone.
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