1-Naphthaleneacetic Acid CAS 86-87-3

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1-Naphthylacetic acid is an organic compound with a molecular formula of C12H10O2, referred to as NAA. Near white crystal, odorless, soluble in hot water, acetone, ethanol, ether, benzene, chloroform, acetic acid and lye, benzene, acetic acid and chloroform, slightly soluble in cold water, easy to decompose in humid environment. It has the function of plant growth regulator, but it is poisonous. Sodium naphthalene acetate is easily soluble in water and stable in common organic solvents. We are a manufacturer of naphthalene acetic acid for sale, which is used as a plant growth hormone and also used in organic synthesis.

1-Naphthaleneacetic acid is a naphthalene plant growth regulator with auxin activity, which is absorbed by roots, stems and leaves. Naphthoic acid is widely used in agriculture, forestry, vegetables, flowers, fruit trees and other fields to induce adventitious root formation and improve the survival rate of tree cuttings; Improve the fruit setting rate and prevent fruit falling before harvest.

(1) Prevent falling flowers and fruits

① Spray the bean inflorescence with 15 mg/kg of liquid medicine.

② When the pumpkin blooms, apply 10~20 mg/kg of liquid medicine to the trowel room.

③ At the flowering stage of tomato, spray flowers with 15~20 mg/kg of liquid medicine.

④ At the flowering stage of watermelon, spray 10~30 mg/kg of liquid medicine once.

⑤ Spray pepper flowers with 50 mg/kg liquid medicine.

(2) Promoting female flower

Before cucumber planting, spray the seedlings with 10mg/L solution for 1-2 times.

(3) Enhance resilience

① At the beginning of tomato virus disease, spray the plant with 20 mg/kg of liquid medicine.

② From the initial flowering stage of tomato, after mixing 0.5% calcium chloride solution with 50 mg/kg naphthoic acid solution, spray the plant, spray once every 15 days, and spray continuously for 2-3 times, to prevent and control navel rot.

③ From the lotus stage of Chinese cabbage, after mixing 0.7% calcium chloride solution with 50 mg/kg of naphthoic acid solution, spray the plant once every 6 to 7 days, five times in succession, to prevent and cure the dry burning heart disease.

① With naphthalene as raw material, in the presence of catalyst zinc chloride, it reacts with formaldehyde in hydrochloric acid to form α- Chloromethylnaphthalene reacts with sodium cyanide in methanol to form α- naphthalene acetonitrile, 1-Naphthaleneacetic acid is hydrolyzed in sulfuric acid aqueous solution to produce crude 1-naphthylacetic acid, neutralized, separated, washed with cold water, dissolved in hot water, and recrystallized.

② Using naphthalene as raw material, react with polyformaldehyde and hydrochloric acid under the catalysis of glacial acetic acid and phosphoric acid to obtain α- Chloromethylnaphthalene, and then prepare 1-naphthoic acid according to the above method. In addition to polyformaldehyde, formaldehyde dimethyl acetal and chloromethyl ether can also be used. 

③ With naphthalene as raw material, in the presence of potassium permanganate catalyst, and acetic anhydride at 130 ℃, crude 1-naphthoic acid can be directly obtained. After the unreacted naphthalene and acetic anhydride are removed, the crude product is washed with cold water, dissolved in hot water, and recrystallized to obtain refined 1-naphthoic acid.

④ Using naphthalene as raw material, under the action of catalyst aluminum chloride, ferric chloride, ferric oxide, potassium bromide or aluminum powder, and chloroacetic acid at 200 ℃, 1-naphthaleneacetic acid can also be directly prepared. After the reaction is completed, neutralize it with alkali, drive out the unreacted naphthalene, filter out sodium naphthylacetate, wash it with cold water, acidize it with acid, and recrystallize it to obtain refined naphthalene.

In the laboratory, naphthalene and acetic anhydride react in the presence of potassium permanganate to obtain naphthalene acetic acid. The reaction formula is as follows: 

Add naphthalene and acetic anhydride into the reactor, stir and heat for refluxing for 10 minutes, and then add fully crushed potassium permanganate in batches within 20 minutes. After adding, keep it warm (120~140 ℃) and stir for reaction for 5 hours. At this time, potassium acetate and manganese acetate precipitate down, and the solution turns brown and black (caused by polymer generation). At the end of the reaction, steam out the excess acetic anhydride and part of naphthalene without Chemicalbook reaction under reduced pressure, and recycle them, The remaining naphthalene is distilled out by steam distillation, and the hot residue after steam distillation is continued to be separated from the polymer by filtration. The filtrate is acidified with sulfuric acid. After cooling, bright yellow crystals (naphthalenoacetic acid) are separated out, and then recrystallized with hot water to obtain light yellow needle-shaped crystalline naphthalenoacetic acid. The process flow chart of naphthoic acid production is as follows: 

The current method requires several separation operations, a large number of equipment and a long process flow. All reactions in the invention are completed in one reactor, and the equipment investment and maintenance amount are small, so the process has obvious progressiveness; In addition, the current method 1 produces a large amount of waste water, which has a certain impact on the environment. There are basically no three wastes in this production process; The purity of N-methylpiperazine prepared by the current method can only reach 99.0%, and the purity of the product can reach 99.95% by this method.

When 1-naphthaleneacetic acid is used as a fruit setting or anti-falling agent, the concentration should not be too high. If the concentration of the active ingredient is increased by 10 or dozens of mg/L, it may cause the opposite effect, because the high concentration of auxin can promote the production of ethylene in plants. When NAA is used as a rooting agent, although its rooting effect is good when it is used alone, the seedling growth is often not ideal, so it is generally mixed with indobutyric acid or other regulators with rooting effect to make the effect better. The amount of liquid medicine sprayed on melons shall be until the leaves are evenly wet. Generally, the amount of liquid medicine sprayed on field crops is about 50 kg per mu, and the amount of liquid medicine sprayed on fruit trees is 75-125 kg. Surfactants can significantly affect the absorption of naphthylacetic acid. Adding Tween Chemicalbook-20, X-77, etc. can increase the absorption of naphthylacetic acid several times. The mixture of 100mg/L naphthoic acid solution and glyphosate has obvious synergistic effect. Precautions: 1 α- Naphthylacetic acid can stimulate skin and mucous membrane. Dispensing and spraying personnel need to pay attention to protection, and timely clean in case of pollution. Do not smoke, drink water or eat during operation. Wash hands, face and possibly contaminated parts in time after work. All tools should be cleaned carefully. The packaging materials shall be timely recycled and properly disposed. two α- Naphthylacetic acid can cause poisoning through the esophagus, etc. Liver and kidney damage can be seen in acute poisoning. Generally, symptomatic treatment is used, and attention should be paid to protecting liver and kidney functions.

► Acute and Chronic Toxicity

Oral LD50: >5,000 mg/kg (rats), indicating low acute toxicity.

Subchronic Studies: Rats fed 5% PEG 400 in diet for 90 days showed no adverse effects on organ weight or hematology.

► Human Exposure Limits

FDA: Permits PEG 400 in foods at ≤50 mg/kg (except chewing gum base, where limits are higher).

OSHA: Recommends an 8-hour time-weighted average (TWA) exposure limit of 10 mg/m³ for PEG dust in occupational settings.

► Allergic Reactions

Rare cases of hypersensitivity to PEG have been reported, particularly in patients receiving PEGylated drugs. A 2021 study linked PEG-3350 in laxatives to anaphylaxis in 0.01% of users, prompting calls for better labeling.

► Environmental Impact

PEG is readily biodegradable (90% degradation in 28 days under aerobic conditions), but high concentrations in wastewater can disrupt microbial communities. Advanced oxidation processes (AOPs) using UV/H₂O₂ effectively mineralize PEG to CO₂ and water.

► Nanoformulations for Enhanced Efficiency

Encapsulating NAA in chitosan nanoparticles (CS-NPs) improves its controlled release and reduces environmental leaching:

Rooting Trials: CS-NPs containing 0.05% NAA achieve 95% rooting in rose cuttings (vs. 80% for free NAA).

Fruit Retention: NAA-loaded CS-NPs extend apple fruit retention by 20 days compared to conventional sprays.

► Biodegradable Alternatives

Researchers are developing eco-friendly auxin analogs like indole-3-butyric acid (IBA) conjugated with starch nanoparticles, which degrade within 30 days in soil.

► CRISPR-Edited Crops with Reduced NAA Dependency

Genome editing is being used to enhance endogenous auxin biosynthesis in crops:

Tomatoes: Overexpression of the YUCCA6 gene increases IAA levels by 3×, reducing the need for exogenous NAA applications.

Rice: CRISPR-knockout of the GH3.6 gene (which inactivates auxins) improves root growth under drought stress without NAA supplements.

► Precision Agriculture Applications

Drones equipped with multispectral sensors detect auxin deficiency in crops, triggering targeted NAA sprays via AI-driven algorithms. Field trials in California almond orchards reduced NAA use by 40% while maintaining fruit set rates.

1-Naphthaleneacetic acid is a versatile and widely used plant growth regulator with significant applications in agriculture, horticulture, and research. Its ability to mimic natural auxins makes it invaluable for promoting root development, enhancing fruit set, and improving crop resilience. However, proper handling and regulatory compliance are essential to mitigate health and environmental risks. As research progresses, NAA is poised to play an even more critical role in sustainable agriculture and plant biotechnology.

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