JP2988018B2 - Method for producing N-alkylaminoethanesulfonic acids - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel method for producing N-alkylaminoethanesulfonic acids useful as raw materials for surfactants, buffers and the like.

[0002]

2. Description of the Related Art As a method for producing N-alkylaminoethanesulfonic acids, the following method is described in the literature. That is, a method of reacting 2-halogenoethanesulfonic acid salt with an amine (Chemical Abstract 10
3, 78310), a method of reacting an isethionate salt with an amine (US Patent Nos. 1999614, 193)
No. 2907).

[0003]

In these methods, in addition to the desired N-alkylaminoethanesulfonic acids, N-alkylaminobis (ethanesulfonic acids) represented by the following general formula (I) are added as secondary compounds. Live. Conventionally, this by-product has poor utility value, and if it is taken out in the separation and purification step after the reaction, it has been treated as waste, and the yield of the target N-alkylaminoethanesulfonic acid deteriorates accordingly. I was

RN (CH ₂ CH ₂ SO ₃ M) ₂ (I) The present invention has been made in view of the above problems, and an object of the present invention is to provide N-alkylaminoethanesulfonic acids. By-products separated from the reaction solution after the production reaction,
That is, it is an object of the present invention to provide a method for reusing N-alkylaminobis (ethanesulfonic acid) s represented by the general formula (I) to obtain N-alkylaminoethanesulfonic acids as a target product in good yield. .

[0005] No mention has been made of the properties of the N-alkylaminobis (ethanesulfonic acid) s, and the chemical behavior thereof has not been clarified at all.

[0006]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have studied the reactivity of N-alkylaminobis (ethanesulfonic acid) s. The present inventors have found a novel fact that N-alkylaminoethanesulfonic acids are produced by the reaction between phenol and an alkylamine, thereby completing the present invention.

That is, the present invention provides an N-alkylaminobis (ethanesulfonic acid) represented by the following general formula (I):
A method for producing N-alkylaminoethanesulfonic acids, which comprises reacting a compound with an alkylamine represented by the following general formula (II) by heating. _{R-N (CH 2 CH 2} SO 3 M) 2 (I) R-NH 2 (II)
[In the formula, R represents a chain or cyclic lower alkyl group (C _1-6 ), and M represents hydrogen, an alkali metal or an alkaline earth metal. Hereinafter, the present invention will be described in more detail.

The N-alkylaminobis (ethanesulfonic acid), one of the raw materials in the present invention, is, for example, 2
-It is obtained by reacting a halogenoethanesulfonic acid salt or isethionate with an alkylamine, but the production method is not particularly limited. In particular,
N-methylaminobis (ethanesulfonic acid), N-ethylaminobis (ethanesulfonic acid), N-propylaminobis (ethanesulfonic acid), N-cyclohexylaminobis (ethanesulfonic acid), and monosodium salts thereof , Disodium salts, monopotassium salts, dipotassium salts, calcium salts, alkali metal salts such as magnesium salts and the like, and alkaline earth metal salts.

As the other starting material, alkylamine having the same alkyl substituent as N-alkylaminobis (ethanesulfonic acid) is used. For example, monomethylamine, monoethylamine, monopropyl Amines and monocyclohexylamine.

The amount of the alkylamine to be used is 2 to 35 times, preferably 10 to 30 times, the mole of N-alkylaminobis (ethanesulfonic acid). The reaction may be carried out in the presence of an alkylamine in excess of 35 times the molar amount, but there is no industrial advantage because only the amount of the unreacted recovered amine increases.

The reaction temperature is not particularly limited. However, in order to obtain a sufficient reaction rate, the reaction temperature is preferably from 150 to 300.
C., more preferably 180 to 250 C.

The reaction pressure is not particularly limited, but is preferably 30 to 80 kg / cm ² G.

Although the present invention has a sufficient effect without adding a reaction accelerator, it does not contain a reaction accelerator such as an alkali metal or alkaline earth metal hydroxide or a carbonate thereof. This is preferable because the reaction temperature and pressure can be reduced and the reaction time can be further reduced.

Water is used as a reaction solvent.

According to the present invention, N-alkylaminobis (ethanesulfonic acids) can be reused to obtain N-alkylaminoethanesulfonic acids. At this time, N-alkylaminobis (ethanesulfonic acid) s are further produced as by-products, which can be reused by using the present invention.

[0016]

EXAMPLES Examples will be described below to explain the present invention, but the present invention is not limited to only these examples. In the following examples, all concentrations are% by weight, and the following abbreviations were used.

CH ₃ N (CH ₂ CH ₂ SO ₃ H) ₂ MDT CH ₃ CH ₂ N (CH ₂ CH ₂ SO ₃ H) ₂ EDT Cyclohexyl-N (CH ₂ CH ₂ SO ₃ H) ₂ CDT CH ₃ NHCH _{2 CH 2 SO 3 H MT CH} 3 CH 2 NHCH 2 CH 2 SO 3 H ET Cyclohexyl-NHCH 2 CH 2 SO 3 H CT example 1 50% MDT disodium salt aqueous solution electromagnetic stirrer 300ml autoclave 63.0g and 40 168.2 g of a 25% aqueous solution of methylamine was charged and reacted at 250 ° C. for 3 hours. The reaction pressure was 76 kg / cm ² G. After the completion of the reaction, the reaction mixture was cooled to 170 ° C., the valve of the autoclave was opened, and unreacted methylamine was distilled off.
The reaction solution after methylamine was distilled off was analyzed by liquid chromatography to find that MT sodium salt was 32.6.
g, 1.4 g of MDT disodium salt.

Example 2 60.0 g of a 50% aqueous solution of MDT monosodium salt, 40
The reaction was carried out under the same conditions as in Example 1 except that 172.8 g of a 17% aqueous methylamine solution and 9.3 g of a 48% aqueous sodium hydroxide solution were charged. 33.4 g, MDT
It contained 1.2 g of disodium salt.

Example 3 67.6 g of a 50% aqueous solution of dipotassium MDT and 16% aqueous solution of methylamine 16 were placed in a 300 ml autoclave.
2.4 g was charged and reacted at 220 ° C. for 3 hours. The reaction pressure was 56 kg / cm ² G. After distilling off unreacted methylamine, the reaction solution was analyzed. The reaction solution is MT
It contained 34.6 g of potassium salt and 1.4 g of dipotassium MDT.

Example 4 In a 300 ml autoclave, 101.6 g of 26% EDT monosodium salt, and a 70% aqueous solution of ethylamine.
5 g and 7.8 g of a 48% aqueous sodium hydroxide solution were charged and reacted at 250 ° C. for 3 hours. Reaction pressure is about 50k
g / cm ² G. After distilling off unreacted ethylamine, the reaction solution was analyzed. The reaction solution was ET sodium salt 2
9.4 g, 1.9 g of EDT disodium salt.

Example 5 56.9 g of a 60% aqueous solution of CDT dipotassium salt and 98% cyclohexylamine 17 were placed in a 300 ml autoclave.
3.0 g was charged and reacted at 200 ° C. for 5 hours. As a result of analysis of the reaction solution, it contained 40.7 g of CT potassium salt and 0.9 g of CDT dipotassium salt.

[0022]

As is apparent from the above description, according to the present invention, N-alkylaminobis (ethanesulfone, which is by-produced when producing N-alkylaminoethanesulfonic acids and is usually of little value, is produced. Acids) can be reused as a raw material for producing useful N-alkylaminoethanesulfonic acids.

──────────────────────────────────────────────────の Continued on the front page (58) Field surveyed (Int. Cl. ⁶ , DB name) C07C 303/22 C07C 309/14 CA (STN) REGISTRY (STN)

Claims (1)

(57) [Claims] 1. An N-alkylaminobis (ethanesulfonic acid) represented by the following general formula (I) and an alkylamine represented by the following general formula (II) are heated and reacted. For producing N-alkylaminoethanesulfonic acids. R—N (CH ₂ CH ₂ SO ₃ M) ₂ (I) R—NH ₂ (II) wherein R represents a chain or cyclic lower alkyl group (C _1-6 ), M represents hydrogen, Represents an alkali metal or alkaline earth metal. ]