JPH0211533A - Method for producing styrenated phenol - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for producing styrenated phenol by reacting phenol and styrene.

Styrenated phenol is a rubber anti-aging agent or
It is a useful substance used as a raw material for surfactants, etc.

[Conventional technology]

As a method for producing styrenated phenol, phenol and styrene,! : Wow, A1. Cl3,,3b(
J3.

H2SO4, H3PO4+ The reaction can be carried out using activated clay or the like as a catalyst (for example, JP-A-58-115
185, etc.). However, conventionally known catalysts have drawbacks such as the complicated decontamination method from the reaction product liquid after the reaction and the marked coloring of the product. Especially when used as a surfactant raw material. It is desirable for the product to be as close to colorless as possible.

Furthermore, since styrenated phenol has a very high boiling point, it is difficult to purify it by distillation.

[Problem to be solved by the invention]

Therefore, there is a need for a method for producing styrenated phenol that is easy to purify and has less coloration in the reaction product obtained by the reaction of phenol and styrene, and the present invention seeks to provide a method that solves the above-mentioned problems. It is something.

[Means for solving problems]

The present invention produces styrenated phenol with less coloring of the shredded product by reacting phenol and styrene to produce styrenated phenol in the presence of a sulfonic acid type cation exchange resin as a catalyst. The present invention provides a method.

[Detailed description of the invention]

The molar ratio of phenol to suderene used in the reaction can be varied as desired, but is generally 1:2 to 5, preferably 1:2.
: Performed in the range of 2 to 3. The reaction products are not a single product, but phenol alkylated with 1 to 3 moles of styrene, styrene alkylated to the phenyl group of alkylated styrene, and styrene alkylated with 1 to 3 moles of styrene.
It is a mixture of oligomers of about 1 to 4 tetramers alkylated to 7 enol, and such a mixture is provided for various purposes.

As the reaction method, a semi-batch method is preferred in which a catalyst is added to phenol and heated to a predetermined temperature, and then styrene is sequentially added under stirring.

This is to prevent undesirable polymerization of styrene, but generally the alkylation reaction rate is faster than the polymerization rate and it is relatively easy to prevent the formation of styrene polymers that are not alkylated to phenol. Further, when styrene is used at least 1.5 times the mole of phenol, the amount of unreacted styrene and phenol remaining can be suppressed to a very small amount.

As the sulfonic acid type cation exchange resin used as a catalyst in the present invention, a strongly acidic ion exchange resin in which a sulfonic acid group is bonded to a copolymer of styrene and divinylbenzene is preferably used. Sulfonic acid cation exchange resins are sometimes commercially available in the form of alkali salts, but in that case, they must be treated with mineral acids or the like to convert them into acid forms before being used as catalysts. Furthermore, if it contains water, the activity will be reduced, so it is desirable to dry it before using it in the reaction and to keep the water content generally below 5% by weight.

The amount of catalyst used is usually 0.1 to 20% relative to phenol.
%, preferably from 0.5 to 10%. In addition, the reaction temperature is 40 to 130°C, preferably 60 to 10°C.
It is carried out in the range of 0°C.

In the method of the present invention, styrenated phenol with good color can be obtained by simply removing the catalyst by filtration or other operations after the completion of the reaction, but if necessary, trace amounts of unreacted phenol or styrene may be removed. It can be increased and removed by methods such as steam stripping.

〔Example〕

The present invention will be specifically explained below using Examples.

[Example-1] Phenol 188f (2 mol) and 24 ft of dry cation exchange resin Amberlyst 15 (Rohm and Haas M) were charged into 11 glass flasks equipped with an AT meter, a condenser tube, and a stirrer. After replacing the system with nitrogen, 8
The temperature was raised to 5°C, and styrene 416f (4 mol) was added over 6 hours while stirring. After the addition was completed, the catalyst was cooled and subjected to FiM, yielding 600 tons of styrenated phenol (yield: 99.
3%). The hue of the product was determined by absorbance method (420 nm).
When measured, it was APHA50. Furthermore, unreacted phenol and styrene were both 1 wtl or less.

[Comparative Example-1] The reaction was carried out in exactly the same manner as in the example except that 422 activated clay (Jilton C8-1 manufactured by Mizusawa Chemical Co., Ltd.) was used as a catalyst.

When the hue of the obtained product liquid was measured in the same manner as in Example-1, it was found to be API (A3500).

[Comparative Example-2] Phenol 18 was added to the same flask as used in the example.
After charging 8 tons of concentrated sulfuric acid and 10F of concentrated sulfuric acid and purging with nitrogen, 416 tons of styrene was added over 6 hours at 50°C to obtain styrenated phenol. When the hue of the obtained product was measured in the same manner as in Example-1, it was found to be APRA95.
It was G.

Patent applicant: Mitsubishi Yuka Co., Ltd. Agent: Patent Attorney Masahisa Nagatani Agent Patent Attorney Takaya Yamamoto

Claims (1)

[Claims] A method for producing styrenated phenol, which comprises reacting phenol and styrene to produce styrenated phenol in the presence of a sulfonic acid type cation exchange resin.