CN101565556B - A kind of preparation method of solvent orange 60 - Google Patents

Abstract

The invention discloses a preparation method of solvent orange 60, and belongs to the field of chemical industry. Mixing phthalic anhydride and 1, 8-naphthalenediamine with the mass ratio of 1: 1 in a reaction device with stirring and refluxing equipment, hydrochloric acid solution with the mass concentration of 1-5%, polar organic solvent capable of being mixed and dissolved with water and non-ionic active catalyst, starting stirring and heating, heating to react for 8-15 hours under the refluxing state, then filtering, washing filter cakes with clear water until the pH value of filtrate is neutral, and finally drying to obtain solvent orange 60; the dosage of the hydrochloric acid solution is 10-20 times of that of 1, 8 naphthalenediamine; the dosage of the polar organic solvent is 1-50% of the total amount of the reaction medium; the dosage of the catalyst is 0.01-2% of the total amount of the reaction medium. The method has the advantages of good product quality by the solvent method and low cost by the water phase method.

Description

A kind of preparation method of solvent orange 60

technical field

The invention relates to a preparation method of solvent orange 60, which belongs to the field of chemical industry.

Background technique

Solvent Orange 60, English name Solvent Orange 60, molecular formula: C18H10N2O, molecular weight: 270.29, CAS number: 6925-69-5. Appearance is orange powder, insoluble in water, slightly soluble in ethanol, benzene, toluene, xylene and other organic solvents. Mainly used in polystyrene, ABS resin. Its structural formula is:

The existing preparation process of Solvent Orange 60 is divided into solvent method and aqueous phase method according to the difference of the reaction medium used. The solvent method is a method for producing solvent orange 60 with a polar organic solvent as the reaction medium. The product produced by this method has high vividness and high product quality. However, because solvent orange 60 has a certain solubility in organic solvents, the product The separation is relatively difficult, and the solvent needs to be recovered, so the production cost is high. The aqueous phase method is a method of producing solvent orange with hydrochloric acid aqueous solution as the reaction medium. It only needs to be filtered to realize product separation, and the reaction medium does not need to be recycled, only neutralization treatment is required, so the production cost is relatively low, but the produced by this method The product brightness is relatively low, and the product quality is poor.

Contents of the invention

The purpose of this invention is to provide a kind of product quality good, the preparation method of solvent orange 60 with low production cost.

Technical scheme of the present invention: a kind of preparation method of solvent orange 60, in the reaction device of belt stirring and reflux equipment, the amount ratio of substance is phthalic anhydride and 1,8-naphthalene diamine and mass Mix hydrochloric acid solution with a concentration of 1 to 5%, a polar organic solvent that can be miscible with water, and a non-ionic active catalyst, start stirring and heating, heat up to reflux and react for 8 to 15 hours, and then filter, the filter cake is used Wash with water until the pH value of the filtrate is neutral, and finally dry to obtain Solvent Orange 60; the amount of the hydrochloric acid solution is 10 to 20 times that of 1,8-naphthalene diamine; the amount of the polar organic solvent is the total amount of the reaction medium. 1% to 50% of the total amount of the catalyst; the amount of the catalyst is 0.01% to 2% of the total amount of the reaction medium.

The polar organic solvent is acetic acid or dimethylformamide (DMF) or alcohol or N-methylpyrrolidone.

The non-ionic active catalyst is fatty alcohol polyoxyethylene ether or alkylphenol polyoxyethylene ether.

The alkylphenol polyoxyethylene ether is nonylphenol polyoxyethylene ether.

Reaction equation of the present invention is as follows:

The fatty alcohol polyoxyethylene ether of the present invention belongs to the nonionic surfactant, and its general chemical _formula is RO( _CH2CH2O ) _nH , wherein, R is generally an alkyl group with 10 to 15 carbons, and n can be 2 An integer between ～30.

其中，R一般为8～12个碳的烷基，n可为2～50间的整数，本发明采用了最常见的壬基酚聚氧乙烯醚作为非离子活性催化剂，其化学为C₉H₁₉C₆H₄O(CH₂CH₂O)nH，其中n为5到20间的整数。Alkylphenol polyoxyethylene ether of the present invention belongs to nonionic surfactant, and its general structural formula is

Among them, R is generally an alkyl group with 8 to 12 carbons, and n can be an integer between 2 and 50. The present invention uses the most common nonylphenol polyoxyethylene ether as a non-ionic active catalyst, and its chemical composition is C ₉ H ₁₉ C ₆ H ₄ O(CH ₂ CH ₂ O)nH, wherein n is an integer between 5 and 20.

Fatty alcohol polyoxyethylene ether and alkylphenol polyoxyethylene ether belong to non-ionic surfactants and have similar properties. The HLB value can be adjusted according to the value of n, so that it has excellent emulsification, wettability, Dispersibility, Solubilization, Detergency and Penetration. In the present invention, fatty alcohol polyoxyethylene ether and alkylphenol polyoxyethylene ether are used as catalysts.

The present invention combines the original solvent method with the water phase method, which not only avoids the relatively difficult separation of products in the solvent method, the need for solvent recovery, and high production costs, but also avoids the relatively low brightness and low quality of the product in the water phase method. However, it achieves the best result of high product vividness and low production cost, which greatly promotes the improvement of product grade and reduces the production cost of enterprises.

Detailed ways

Example 1

Add 200g of 3% hydrochloric acid aqueous solution, 30g of alcohol, 10g of phthalic anhydride, 10.7g of 1,8-naphthalene diamine, and 0.3g of fatty alcohol polyoxyethylene ether in sequence in a three-necked flask with a stirring and reflux condenser, and start stirring , be warming up to reaction system slight reflux state, filter after reacting for 8 hours, filter cake is washed with clear water until the filtrate is neutral, and dry to obtain product 17.5g (being 95.9% of theoretical yield). The color shade of the product is similar to that of the standard product (see Table 1 for details), and the intensity is 99.0%.

Table 1

(Where: ΔE-color difference, ΔH-hue difference, ΔL-brightness difference, ΔC-chroma difference,

Δa-the difference in redness and greenness, Δb-the difference in yellowness and blueness, the smaller the ΔE, the closer the color of the product is to the standard product. Generally, if ΔE is less than 3, the requirement is met. If the requirement is more stringent, ΔE should be less than 1. )

Example 2

Add 1000kg 5% hydrochloric acid aqueous solution, 100kg dimethylformamide (DMF), 100kg phthalic anhydride, 107kg 1,8-naphthalene diamine, 5kg Nonylphenol polyoxyethylene ether, start stirring, heat up to the state of slight reflux of the reaction system, filter after 12 hours of reaction, wash the filter cake with water until the filtrate is neutral, and dry to obtain 177kg of the product (96.8% of the theoretical yield) . The product is similar to the standard product (see Table 2 for details), and the strength is 101.0%.

Table 2

light source ΔE ^* ΔH ^* ΔC ^* ΔL ^* Δa ^* Δb ^* D65/10 0.32 0.22 -0.12 -0.20 -0.25 0.01 A/10 0.34 0.20 -0.15 -0.23 -0.25 -0.05 F2/10 0.30 0.21 -0.05 -0.21 -0.22 0.01

Example 3

Add 300kg of 1% hydrochloric acid solution, 60kg of acetic acid, 20kg of phthalic anhydride, 21.4kg of 1,8-naphthalene diamine, and 5kg of nonylphenol polyoxyethylene into a 500L enamel reactor with frame stirring and reflux condenser. Ether, start stirring, heat up to the state of slight reflux of the reaction system, filter after reacting for 8 hours, wash the filter cake with water until the filtrate is neutral, and dry to obtain 35kg of product (95.7% of theoretical yield). The product is similar to the standard product (see Table 3 for details), and the strength is 98.9%.

table 3

light source ΔE ^* ΔH ^* ΔC ^* ΔL ^* Δa ^* Δb ^* D65/10 0.45 0.35 -0.07 -0.27 -0.34 0.11 A/10 0.47 0.34 -0.11 -0.31 -0.36 0.04 F2/10 0.42 0.33 0.04 -0.26 -0.30 0.13

Example 4

Add 300kg of 3% hydrochloric acid solution, 20kg of N-methylpyrrolidone, 20kg of phthalic anhydride, 21.4kg of 1,8-naphthalene diamine, and 1kg of nonylphenol into a 500L enamel reactor with frame stirring and reflux condenser. For polyoxyethylene ether, start stirring, heat up to the state of slight reflux of the reaction system, filter after 10 hours of reaction, wash the filter cake with water until the filtrate is neutral, and dry to obtain 36 kg of the product (95.7% of the theoretical yield). The product is similar to the standard product (see Table 3 for details), and the strength is 101.8%.

Table 4

light source ΔE ^* ΔH ^* ΔC ^* ΔL ^* Δa ^* Δb ^* D65/10 0.68 -0.23 0.45 0.45 0.42 0.28 A/10 0.77 -0.23 0.53 0.51 0.43 0.39 F2/10 0.65 -0.20 0.40 0.47 0.31 0.32

Claims (2)

1. a preparation method of Solvent Orange 60 is characterized in that: in the reaction unit of band stirring and reflux equipment, the phthalic anhydride and 1,8-naphthalene diamine and mass Mix a hydrochloric acid solution with a concentration of 1-5%, a polar organic solvent that can be miscible with water, and a non-ionic active catalyst, start stirring and heating, heat up to reflux and react for 8-15 hours, then filter, and use the filter cake Wash with water until the pH value of the filtrate is neutral, and finally dry to obtain Solvent Orange 60; the amount of the hydrochloric acid solution is 10 to 20 times that of 1,8-naphthalene diamine; the amount of the polar organic solvent is the total amount of the reaction medium. 1 ~ 50% of the amount; the amount of the catalyst is 0.01 ~ 2% of the total amount of the reaction medium; the polar organic solvent is acetic acid or dimethylformamide (DMF) or alcohol or N-methylpyrrolidone; the The non-ionic active catalyst is fatty alcohol polyoxyethylene ether or alkylphenol polyoxyethylene ether. 2. the preparation method of a kind of solvent orange 60 according to claim 1 is characterized in that described alkylphenol polyoxyethylene ether is nonylphenol polyoxyethylene ether.