4'-Aminoacetanilide CAS 122-80-5

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4'-Aminoacetanilide, also known as p-aminoacetanilide or N-acetyl-phenylenediamine, chemical formula C8H10N2O, CAS 122-80-5, is an organic compound that is a light red brown crystalline powder, but its color may gradually darken in air. Easy to dissolve in hot water, ethanol, and ether, but slightly soluble in cold water. This indicates that its solubility in water significantly increases with increasing temperature.

Mainly used as a dye intermediate for the preparation of dispersed dyes and acidic dyes, such as Disperse Yellow G, Disperse Blue H3R, Disperse Blue 5R, Direct Acid Resistant vermilion 4BS, Direct Sun Resistant Jujube Red, Acid Resistant magenta 6B, Reactive Blue AG, Black Salt ANB, and Neutral Brilliant Blue GV. It may also have potential application value in other fields. For example, in chemical research, it can be used as a model compound to study the mechanisms and kinetics of organic chemical reactions; In materials science, it can be introduced as a functional group into polymer materials, endowing them with new properties; In environmental science, it can be used as a component of adsorbents or catalysts to treat environmental problems such as wastewater and exhaust gases. However, these applications may still be in the research or preliminary application stage and have not yet been widely promoted and applied.

4'-Aminoacetanilide, as a key dye intermediate, plays an indispensable role in the preparation of dispersed dyes and acid dyes.

Function in the preparation of dispersed dyes

Disperse dyes are a type of dye that are insoluble in water but can be dispersed in small particle form in the presence of dispersants. They are mainly used for dyeing synthetic fibers such as polyester fibers and acetate fibers. As an important intermediate of dispersed dyes, it mainly participates in its preparation process through the following pathways:

(1) Reactivity:

The amino and acetyl functional groups in its molecule endow it with good reactivity. These functional groups can undergo substitution, addition, condensation and other reactions with other compounds to generate dispersed dye molecules with specific structures and properties.

(2) Structural diversity:

By adjusting reaction conditions and types of reactants, it is possible to modify and modify their structures, thereby preparing dispersed dyes with different colors, fastness, and application properties. This structural diversity enables dispersed dyes to meet different fiber types and dyeing needs.

(3) Improving dye performance:

In the process of preparing dispersed dyes, the introduction of this product can significantly enhance the dispersibility, solubility, stability, and dyeing performance of the dye. For example, by controlling the reaction conditions, dye particles with uniform particle size and good dispersion can be prepared, thereby improving the dye uptake and dyeing uniformity; Meanwhile, optimizing the molecular structure of dyes can enhance the interaction force between dyes and fibers, and improve the wash and sun fastness of dyes.

(4) Promoting the environmental protection of dyes:

With the increasing awareness of environmental protection and the improvement of environmental regulations, the demand for environmentally friendly dyes in the dye industry is growing. As dye intermediates, the synthesis and use of these dyes can be reduced by selecting environmentally friendly raw materials, optimizing synthesis processes, and other measures to reduce pollution and damage to the environment. Meanwhile, improving the molecular structure of dyes can enhance their biodegradability and recyclability, thereby achieving green production and use of dyes.

Function in the preparation of acidic dyes

Acid dyes are a type of dye that can dye fibers in acidic or neutral media, mainly used for dyeing natural fibers such as wool and silk. It also plays an important role in the preparation of acidic dyes:

(1) Provide dyeing groups:

The amino group in this molecule is one of the common dyeing groups in acidic dyes. Under acidic conditions, amino groups can undergo protonation reactions to form positively charged ions, which then undergo electrostatic attraction with negatively charged fiber surfaces to achieve dyeing. Therefore, the introduction of this product provides the necessary dyeing groups for acidic dyes.

(2) Enhancing dye stability:

In the preparation process of acidic dyes, the acetyl functional group of the product can play a role in stabilizing the molecular structure of the dye. The introduction of acetyl groups can reduce the interaction forces between dye molecules, decrease the aggregation and precipitation of dye molecules, thereby improving the solubility and stability of dyes.

(3) Enriching dye colors:

By changing the types of compounds and reaction conditions that react with it, acid dyes of different colors can be prepared. This color diversity enables acid dyes to meet different fiber types and dyeing needs, providing more choices for the textile industry.

(4) Improving dyeing performance:

The introduction of this substance can also enhance the dyeing performance of acidic dyes. For example, optimizing the molecular structure of dyes can enhance the interaction force between dyes and fibers, improve the dye uptake and dyeing uniformity of dyes; Meanwhile, by adjusting parameters such as molecular weight and shape of dye molecules, the permeability and diffusion of dyes can be improved, thereby enhancing the dyeing effect and depth of dyes.

Specific application examples in dye preparation

4'-Aminoacetanilide can be synthesized by a variety of methods, the following is a commonly used synthetic method and its detailed steps:

Synthetic method: condense 4-aminobenzoic acid and acetyl chloride to generate 4'-acetamidobenzoic acid, then diazotize it with sodium nitrite, and then reduce it with sodium sulfite to obtain 4'-aminoacetamidobenzoic acid amide (4' -Aminoacetanilide).

The detailed steps are as follows:

1. Add 4-aminobenzoic acid (0.1 mol) into anhydrous dimethylformamide (DMF) (20 mL) at room temperature, and stir well.

2. Add acetyl chloride (0.1 mol) dropwise to the above mixture, and continue stirring for 1 hour.

3. Cool the above mixture to room temperature and add 1.2 equivalents of triethylamine, and react for 2 hours under stirring.

4. Filter to obtain 4'-acetamidobenzoic acid crystals, wash with absolute ethanol, and dry to obtain a pure product.

5. In ice water, use sodium nitrite (0.1 mol) and sodium hydroxide solution (0.1 mol) to diazotize 4'-acetamidobenzoic acid, and the reactant solution should be slowly added dropwise and kept stirring.

6. The diazotization product was quickly added to the mixture of sodium sulfite (0.2 mol) and sodium hydroxide solution (0.2 mol), and stirred at room temperature for 2 hours.

7. Filter to obtain 4'-aminoacetamidobenzoic acid amide crystals, wash with water, and dry to obtain a pure product.

 

Through the above steps, a high-purity product can be obtained. It is worth noting that safety needs to be paid attention to during the experimental operation to avoid the generation and discharge of harmful volatiles and waste. 

4'-Aminoacetanilide is an organic compound that can be synthesized by the following laboratory steps as follows:

Add 4-aminobenzoic acid (0.1 mol) and acetyl chloride (0.1 mol) into a three-necked flask, add a small amount of sodium hydroxide solution (2-3 mL) as a catalyst, and then cool with ice water. Stir for 1 hour until the solution becomes cloudy.

Add a small amount of absolute ethanol for mixing, and then filter to obtain a solid product. The solid product was repeatedly washed with absolute ethanol until the pH of the washing liquid was neutral. The product was dried in a vacuum desiccator to obtain 4'-acetamidobenzoic acid.

Add 4'-acetamidobenzoic acid (0.1 mol) into water (10 mL), then add sodium nitrite (0.1 mol) and sodium hydroxide solution (0.1 mol), react at room temperature for 30 minutes, and generate heavy Nitriding products.The diazotization product was quickly added to the mixture of sodium sulfite (0.2 mol) and sodium hydroxide solution (0.2 mol), and stirred at room temperature for 2 hours. After the reaction, the product was washed with water.

Extract the product with chloroform, and then neutralize it with alkaline alcohol solution. The chloroform layer was filtered and the chloroform was evaporated to give the product.

Through the above laboratory synthesis method, a high-purity product can be obtained. Safety needs to be paid attention to during the experiment to avoid contact with skin and inhalation of harmful gases and vapors.

What are the side effects of this compound?

• Skin irritation and allergies: Certain chemicals that come into contact with the skin may cause redness, swelling, pain, itching, or allergic reactions.
• Eye irritation: Chemical splashes into the eyes may cause eye pain, tearing, redness, blurred vision, or permanent damage.
• Respiratory irritation: Inhaling gases or dust containing chemical substances may cause irritation to the respiratory tract, leading to coughing, shortness of breath, difficulty breathing, or asthma.

• Gastrointestinal irritation: Ingestion of chemicals may cause nausea, vomiting, abdominal pain, diarrhea, or more serious digestive system problems.
• Neurological effects: Certain chemicals may affect the nervous system, causing headaches, dizziness, drowsiness, insomnia, or more severe neurotoxic reactions.
• Liver and kidney damage: Long term exposure or ingestion of chemicals may cause damage to the liver and kidneys, leading to abnormal liver function, nephritis, or kidney failure.

• Carcinogenicity: Some chemicals have been proven to be carcinogenic, and long-term exposure or ingestion may increase the risk of cancer.

4'-Aminoacetanilide is a versatile aromatic amine with significant applications in the dye, pharmaceutical, and chemical industries. Its synthesis is well-established, though ongoing research aims to improve efficiency and sustainability. While it offers numerous benefits, safety precautions must be strictly followed due to its potential health and environmental hazards. With increasing demand for high-performance materials and sustainable chemistry, the future of this drug remains promising, provided that industry adapts to evolving regulatory and market challenges.

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