1‑Naphthalene acetic acid, CAS C12H10O2 registration number: 86‑87-3, chemical name: α‑naphthalene acetic acid, physical and chemical properties: white needle crystal or crystalline powder, odorless. Slightly soluble in cold water and ethanol, easily soluble in hot water, acetone, ether, chloroform, benzene, acetic acid and alkali solution.
Naphthaleneacetic acid is a broad-spectrum plant growth regulator, which can promote cell division and expansion, induce the formation of adventitious roots, increase fruit setting, prevent fruit drop, and change the ratio of female and male flowers. It can enter the plant through the tender epidermis of leaves and branches, and the seeds are transported to the whole plant along with the nutrient flow.
1-Naphthalene acetic acid (NAA) is a plant growth regulator that promotes plant growth and development. In addition, 1-Naphthalene acetic acid has the following uses:
1. Plant growth promoter: 1-Naphthalene acetic acid can be used as a plant growth promoter to promote plant growth and development, increase plant root development, and increase plant yield.
2. Fruit expansion agent: 1-Naphthalene acetic acid can be used as a fruit expansion agent to promote fruit expansion and increase fruit yield.
3. Fruit ripening agent: 1-Naphthalene acetic acid can be used as a fruit ripening agent to promote fruit ripening and improve fruit quality.
4. Tar remover: 1-Naphthalene acetic acid can be used as a tar remover to remove tar in the oil well and keep the oil well smooth.
5. Pharmaceutical intermediates: 1-Naphthalene acetic acid can be used as pharmaceutical intermediates for the synthesis of some drugs.
6. Dye intermediate: 1-Naphthalene acetic acid can be used as a dye intermediate to synthesize some dyes.
7. Electrochemical device material: 1-Naphthalene acetic acid can be used as an electrochemical device material, such as for preparing battery materials.
In conclusion, 1-Naphthalene acetic acid has a wide range of applications in the fields of plant production, medicine, dyes and electrochemistry.
Synthesis of Naphthaleneacetic Acid:
Add 300Kg of naphthalene and 100Kg of chloroacetic acid to the reactor, add 2.5Kg of iron powder and 12Kg of sodium bromide to carry out the synthesis reaction at 210°C, after the reaction, add 600L of water and 85Kg of 46% liquid sodium hydroxide to the reactor , carry out the reaction at 40°C, adjust the pH value to 10-11, start steam distillation to recover unreacted naphthalene, after recovering the naphthalene by distillation, pump the aqueous solution containing sodium naphthalene acetate into the acidification tank, and cool down to 40 DEG C, add mass percentage concentration and be 25% hydrochloric acid, adjust pH value 5～6, remove the impurity that generates in the synthetic reaction, after filtering, add sodium chloride 180Kg in the filtrate, make the content of sodium chloride in the filtrate be 20 % (the mass ratio of sodium chloride and filtrate is 20:80).
After cooling down to 15°C to 20°C for 5 hours, and stirring for another 3 hours, a solid precipitated and was centrifuged. The filtrate obtained by centrifugation is collected for the next addition and recycling after the synthesis reaction of naphthalene and chloroacetic acid is completed. The solid obtained after centrifugation was taken for identification, and the identification spectrum is shown in Figure 3, and the spectrum data are shown in Table 1, and the results showed that the solid was sodium naphthalene acetate. Take the solid and evaporate the water to dryness in an evaporating kettle, and then pulverize to obtain 150Kg of crude sodium naphthalene acetate with a content of 75%. Afterwards, naphthaleneacetic acid can be obtained by acidification.
refined:
Put the crude product of naphthalene acetic acid in an iron bucket, add 50 times of water and 1% activated carbon (for decolorization), and boil on high heat. If the acidity decreases, a little acid can be added to keep the pH at 1-2. , Naphthalene acetic acid is dissolved in hot water, and after a little cooling, a white precipitate is obtained. When it precipitates, a little black oil appears on the upper layer of the solution. It still contains tea acetic acid, and the black oil is first skimmed off with a spoon. And put it in another iron bucket to heat again.
Filter the above solution while it is hot. It is best to heat a thin layer of cotton under the filter cloth to prevent impurities from mixing into the finished product. The filtrate crystallizes after cooling, and then filters and dries (below 70C`) to obtain the refined product of naphthaleneacetic acid, which is white or slightly pink, with a melting point of 128-132°C and naturally cooled, in the shape of needles. The crystals that are rapidly cooled with ice are small powder shape.
Some important reactivity properties of 1-Naphthaleneacetic acid (NAA) are as follows:
1. Acid-base neutralization reaction: 1-Naphthalene acetic acid is a weak acid, which can be neutralized with alkali to generate corresponding salts.
2. Esterification reaction: 1-Naphthalene acetic acid can react with alcohol to generate corresponding esters.
3. Reaction of carboxylic acid derivatives: 1-Naphthalene acetic acid can react with electrophilic reagents (such as acylating reagents) to generate corresponding carboxylic acid derivatives, such as acid chlorides and esters.
4. Response to metal ions: 1-Naphthalene acetic acid can form a complex with metal ions (such as Cu2+), which can be used as an electrocatalyst for electrochemical reactions.
5. Carboxylate reaction: 1-Naphthalene acetic acid can transesterify with organic nucleophiles (such as imines and alcohols) to generate corresponding carboxylates.
In summary, the reactivity of 1-Naphthalene acetic acid is rich and diverse, and these reactions provide a variety of methods for the preparation, synthesis, and modification of chemical substances.