CN114773163A - Preparation method of alkyl naphthol - Google Patents

Abstract

A preparation method of alkyl naphthol, characterized in that using trifluoromethanesulfonic acid and/or methanesulfonic acid as catalyst, naphthol and olefin as raw materials, stirring and mixing naphthol, olefin and catalyst, and the temperature is controlled at 80- 200° C., react for 10-200min; sediment the reaction product into layers, and separate the upper oil phase and the lower catalyst phase; add an extractant to the oil phase, stir for 1-20 minutes, and then settle into layers to obtain an extractant phase and an oil phase ; The extractant phase is heated and evaporated to recover the extractant, and the recovered catalyst is obtained; the oil phase is heated to separate the residual extractant, unreacted naphthol and olefin by evaporation to obtain an alkyl naphthol.

Description

A kind of preparation method of alkyl naphthol

technical field

The invention belongs to the field of fine chemicals, and relates to a production method of alkyl naphthol. The International Patent Classification falls under C10B.

Background technique

Alkyl naphthol is a new type of substance with a wide range of uses. It is expected to be used as a petroleum additive and also as a surfactant. The application in other fields is also constantly being explored.

The synthetic method of alkylnaphthol has not been reported yet. Naphthols include α-naphthol (1-naphthol) and β-naphthol (2-naphthol), both of which can be used as raw materials.

This patent provides a preparation method of alkyl naphthol, which can be convenient for continuous production and batch production. The method includes the following parts:

1. a preparation method of alkylnaphthol is characterized in that comprising the steps:

(1) Mixing naphthol and olefin, so that naphthol and olefin are mixed uniformly, then add catalyst, stir and heat to 80-200 ℃, keep reaction 10-200min;

(2) reduce the temperature to 40-70°C, add an extractant, stir for 1-20 minutes, then settle for 5-300 minutes, and separate the extractant layer;

(3) repeating step (2), until the pH value of the extractant layer reaches more than 6;

(4) extracting agent phase is collected, and extracting agent and catalyzer are recovered by heating and evaporation;

(5) The raffinate is heated to 200-360°C, and the residual extractant, unreacted naphthol and olefin are separated by evaporation to obtain alkyl naphthol.

2. The method according to 1, wherein the catalyst is trifluoromethanesulfonic acid.

3. The method according to 1, wherein the catalyst is methanesulfonic acid.

4. The method according to 1, wherein the catalyst is a mixture of trifluoromethanesulfonic acid and methanesulfonic acid.

5. The method according to 1 and 2, characterized in that the catalyst dosage is 0.2%-15% of the total amount (weight) of naphthol and olefin.

6. The method according to 1 and 3, characterized in that the catalyst dosage is 1%-10% of the total amount (weight) of naphthol and olefin.

7. The method according to 1, wherein the olefin is a C5-C25 α-olefin.

8. The method according to 1, characterized in that the reaction temperature is 100-140°C.

9. The method according to 1, characterized in that the extraction agent is one or more mixtures in water, methanol, ethanol, and isopropanol.

In this method, the catalyst used is trifluoromethanesulfonic acid or methanesulfonic acid, or a mixture of trifluoromethanesulfonic acid and methanesulfonic acid. When using trifluoromethanesulfonic acid, the catalyst dosage is 0.5%-3% of the total amount (weight) of naphthol and olefin, and when using methanesulfonic acid, the optimum catalyst dosage is 5% of the total amount (weight) of naphthol and olefin- 10%.

The olefin is a C5-C25 α-olefin, and the material ratio of the olefin and the naphthol is 1-3:1. The reaction temperature of this process is 80-200°C, and the optimal temperature is 100-140°C. Of course, higher and lower temperatures are also possible. Generally, the reaction temperature is not higher than 200°C and not lower than 50°C. The extractant is one or a mixture of water, methanol, ethanol, and isopropanol.

When the extractant and unreacted naphthol and olefin are removed by distillation, atmospheric distillation, vacuum distillation and steam stripping can also be used.

effect of invention

The preparation of alkylnaphthol is carried out according to the above method, and the yield reaches more than 80%, which can be produced intermittently or can be continuously operated.

Detailed ways

Below in conjunction with embodiment, the method of the present invention is further described.

Example 1:

In a 500ml autoclave, add 100g of 1-naphthol, 130g of n-pentene, 0.5g of catalyst trifluoromethanesulfonic acid, the reaction temperature is 120°C, the reaction time is 3 hours, the temperature is lowered to 70°C after the reaction, and the catalyst is washed away with water , each washing is settled for 5-300 minutes, until the stratification is obvious (the following example is also the case), washed 4 times, until the pH value of the water reaches 6, steamed out unreacted naphthol and n-pentene to obtain amyl naphthol , the yield is 90%.

Example 2:

In a 500ml three-necked flask, add naphthol 100g, dodecene 300g, heat up to 100°C, stir evenly, catalyst trifluoromethanesulfonic acid 1g, reaction temperature 100°C, reaction time 1 hour, cool down to 40°C after the reaction The catalyst was washed off with methanol, and washed 4 times until the pH value of methanol reached 6, and the unreacted naphthol and dodecene were distilled off to obtain dodecyl naphthol with a yield of 92%.

Example 3:

In a 500ml three-necked flask, add naphthol 100g, dodecene 200g, catalyst methanesulfonic acid 30g, reaction temperature 80 ° C, reaction time 6 hours, after the reaction, use 200ml ethanol to wash off the catalyst, wash 5 times, until the methanol The pH value reached 6, and the unreacted naphthol and dodecene were distilled off to obtain dodecyl naphthol with a yield of 81%.

Example 4:

In a 500ml there-necked flask, add naphthol 100g, dodecene 100g, catalyst methanesulfonic acid 30g, reaction temperature 130 ℃, reaction time 1 hour, after the reaction is cooled to 50 ℃, with 200ml isopropanol and water 1: 1 (volume) of the mixture was used to wash the catalyst in the product, and washed 5 times until the pH value of the aqueous solution reached 6, and the unreacted naphthol and dodecene were distilled off to obtain dodecyl naphthol with a yield of 92%.

Example 5:

In a 500ml three-necked flask, add naphthol 100g, C12-25 mixed alkene 300g, catalyst trifluoromethanesulfonic acid 10g, reaction temperature 150 ℃, reaction time 5 minutes, after the reaction is cooled to 50 ℃, with 200ml ethanol and water The catalyst was washed with the mixture solution obtained at a ratio of 1:1, washed three times until the pH value of the aqueous solution reached 6, and the unreacted naphthol and dodecene were distilled off to obtain dodecyl naphthol with a yield of 93%.

Example 6:

In a 500ml three-necked flask, add naphthol 100g, dodecene 100g, catalyst methanesulfonic acid 10g, trifluoromethanesulfonic acid 2g, reaction temperature 200 ℃, reaction time 10 minutes, after the reaction is cooled to 50 ℃, with 200ml The catalyst was washed off with ethanol and washed for 5 times until the pH value of the ethanol solution reached 6, and the unreacted naphthol and dodecene were distilled off to obtain dodecyl naphthol with a yield of 82%.

It can be seen from the above examples that qualified alkyl naphthol products can be produced by using this method. Of course, the above is only an embodiment of the present invention. It should be pointed out that those skilled in the art can make several improvements and modifications without departing from the principles of the present invention. These improvements and Retouching all fall within the protection scope of the present invention.

Claims (9)

1. a preparation method of alkylnaphthol is characterized in that comprising the steps: (1) Mixing naphthol and olefin to make the mixture of naphthol and olefin evenly, then adding catalyst, stirring and heating to 80-200 ℃, keeping reaction for 10-200min; (2) reduce the temperature to 40-70°C, add an extractant, stir for 1-20 minutes, then settle for 5-300 minutes, and separate the extractant layer; (3) repeating step (2), until the pH value of the extractant layer reaches more than 6; (4) extracting agent phase is collected, and extracting agent and catalyzer are recovered by heating and evaporation; (5) The raffinate is heated to 200-360°C, and the residual extractant, unreacted naphthol and olefin are separated by evaporation to obtain alkyl naphthol. 2. The method according to claim 1, wherein the catalyst is trifluoromethanesulfonic acid. 3. method according to claim 1 is characterized in that catalyzer is methanesulfonic acid. 4. The method according to claim 1, wherein the catalyst is a mixture of trifluoromethanesulfonic acid and methanesulfonic acid. 5. The method according to claim 1 and 2, characterized in that the catalyst dosage is 0.2%-15% of the total amount (weight) of naphthol and olefin. 6. The method according to claim 1 and 3, characterized in that the catalyst dosage is 1%-10% of the total amount (weight) of naphthol and olefin. 7. The method according to claim 1, wherein the olefin is a C5-C25 alpha-olefin. 8. The method according to claim 1, characterized in that the reaction temperature is 100-140 °C. 9. method according to claim 1 is characterized in that extraction agent is one or more mixtures in water, methanol, ethanol, isopropanol.