Recent developments in chemistry written in language suitable for students. All rights reserved. (a) Compounds of the following general formula (7): wherein R12 to R15, independently of each other, denote a hydrogen atom or an alkyl with 1 to 3 carbon atoms. Privacy Policy After this stirring, the pH of the reaction liquid was adjusted to 9.8 with sodium hydroxide to carry out a reaction at 80 °C for 12 hours. The above Jeroen van Westrenen et al. When the above deposition is carried out using the seed crystal of the ether carboxylate salt, the deposition is, for example, carried out by adding the seed crystal in an amount of 0.005 weight % or more of the resultant ether carboxylate salt. After the reaction, if the pH of the reaction liquid is adjusted within the range of 10∼14, preferably 12∼14, then the hydroxide of the rare earth element precipitates in the form of a hardly soluble solid and therefore can easily be separated from the reaction liquid by conventional separation means such as filtration. 46, no. methyl > primary > secondary. Soaps, which are usually the sodium or potassium salts of fatty acids, are carboxylates. A typical example is maleic acid. Incidentally, in the formulae below, the carboxylate salt is represented as the corresponding carboxylic acid. The cause of such problems is that the ether compound, as once obtained, easily reverts to the raw compounds due to the reverse reaction, or that a side reaction competing with the reverse reaction occurs to give a byproduct. An amount of 19.6 g of maleic anhydride was dissolved into 50 g of water. Another object of the present invention is to facilitate the recovery of the expensive catalyst. First, 29.4 g (0.3 mol) of maleic anhydride and 32.6 g (0.3 mol) of a 70 weight % aqueous glycolic acid solution were dissolved into 60 g of water, and then 2.4 g (0.0074 mol) of lanthanum oxide was added thereto. Thus, a powder or aqueous solution of the alkaline carbonate may be added into the reaction liquid, or the reaction liquid may be added into a powder or aqueous solution of the alkaline carbonate. Primary haloalkanes (alkyl halides) undergo. Then, 21.7 g of a 70 weight % aqueous glycolic acid solution and 1.6 g of lanthanum oxide (molar ratio to maleic anhydride: 0.025) were added thereto, and the resultant reaction liquid was stirred at room temperature until it became homogeneous. In the case where the amount of the catalyst as used is smaller than 0.0001 mol per 1 mol of the carboxyl-group-containing organic compound, the etherification reaction advances with difficulty. Among them, lanthanum is preferably used because it is relatively inexpensive and easily available. After this stirring, the pH of the reaction liquid was adjusted to 9.8 with sodium hydroxide to carry out a reaction at 80 °C for 10 hours. 16, 1990, pages 5741-58, XP002114771, Glawe, Delfs, Moll (Postfach 26 01 62, DE). It is replaced by the alkanoate ion (carboxylate ion) resulting in a solution that contains the ester and the salt of the halide ion. After the end of the reaction, the same operation as of Example 1 was carried out to obtain trisodium carboxymethoxysuccinate (CMOS-3Na) with a yield of 81.0 mol % (as based on the charged maleic anhydride) in the filtrate. (e) Compounds of the following general formula (5): wherein: R7 denotes a hydrogen atom or an alkyl with 1 to 3 carbon atoms; and X is the same as that in general formula (1) above. (7) High yeilds are only obtained for primary haloalkanes, and, to a lesser extent, secondary haloalkanes. The hydroxide ion (OH-) replaces (substitutes for) the lost halide ion. Typical examples are glycolic acid, β-hydroxypropionic acid, and lactic acid. As a result, the inventors completed the present invention by finding that: if the ether compound, which is a product, is deposited in the course of the reaction, the ether compound is removed from the liquid-phase reaction system, so the concentration of the raw compounds becomes higher than that in a state before the deposition (state where the ether compound is present in the reaction system), and therefore, the etherification reaction is promoted, and the side reaction is inhibited from occurring. & Terms of Use. However, the rare earth element is expensive, so it is desired to save the amount of the rare earth element, as used, or to recover and reuse the catalyst as already used for the reaction, for the purpose of saving the production cost. The above water-insoluble salt, as separated from the reaction liquid, can be reused as a rare earth element source for a new etherification reaction, so the aforementioned etherification reaction can repeatedly be carried out. After this stirring, the pH of the reaction liquid was adjusted to 9.8 with sodium hydroxide to carry out a reaction at 80 °C for 20 hours. The halogen atom, X, leaves the haloalkane molecule as the halide ion, X-. In addition, from results of analysis of the filtrate by ICP (inductively coupled plasma). An amount of 19.6 g of maleic anhydride was dissolved into 50 g of water. Incidentally, the ether carboxylate salt, as obtained in this way, usually has the form in which part or all of carboxyl groups are, for example, displaced by carboxylate salt groups with alkaline metals, alkaline earth metals, alkylamines, alkanolamines, polyamines, or ammonia. [63]. The raw compounds include a hydroxyl-group-containing organic compound and a carboxyl-group-containing organic compound, wherein the carboxyl-group-containing organic compound is at least one compound selected from the group consisting of carboxyl-group-containing unsaturated organic compounds and carboxyl-group-containing epoxy compounds.