methyl carbonate;triethyl(methyl)azanium

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By following the same procedure as Example 20 (2nd step) except that 8.8 g of methyltriethylammonium methyl carbonate, 8.8 g of water, and 4.5 g of maleic anhydride were used, 10.6 g (yield of 100%) of methyltriethylammonium maleate was obtained. The content of monomethyl maleate was less than 0.15 and the contents of impurity ions were all less than 1 ppm.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Next, the reaction solution of triethylmethylammonium methylcarbonate was reacted with 42% aqueous solution of fluoroboric acid at room temperature to obtain a reaction solution of triethylmethylammonium tetrafluoroborate. Then, the reaction solution of triethylmethylammonium tetrafluoroborate was added to n-butanol and subjected to rectification to remove methanol, dimethyl carbonate and water to obtain a tank bottom liquid containing crude triethylmethylammonium tetrafluoroborate. Then, the crude triethylmethylammonium tetrafluoroborate was purified by crystallization using n-butanol/water mixed solvent (85/15 in weight ratio) to obtain purified triethylmethylammonium tetrafluoroborate.

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Next, triethylamine and dimethyl carbonate were mixed with methanol as a solvent in a molar ratio of triethylamine/dimethyl carbonate=1/1.5, heated under a pressure of 1.5 MPa and at a temperature of 135° C. for 15 hours to carry out quaternarization until a conversion of 99.9% is achieved to obtain a reaction solution of triethylmethylammonium methylcarbonate. The conversion was measured by gas chromatography.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: From EP-A-291 074, it is known that dimethyl carbonate acts as a methylating agent during its reaction with an approximately stoichiometric amount of a tertiary amine. Thus, for example, the reaction of triethylamine with dimethyl carbonate gives the product triethylmethylammonium methyl carbonate in 89.9% yield (loc. cit., Example 1).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 622 g (4.5 mol) of isophorone in the presence of 4 g (0.021 mol) of triethylmethylammonium methylcarbonate there are added 288.3 g of a mixture of 3 mol of HCN and 1.5 mol of isophorone, over a period of 120 min and at a reaction temperature of 120° C. The HCN conversion at the end of the reaction is 99.9%. Following neutralization with 2.4g of H3PO4 the mixture is distilled. There are obtained 424.1 g of isophorone and 479.2 g of 3-cyano-3,5,5-trimethylcyclohexanone: the distillation residues weigh 12.8 g, this is equivalent to 1.4% based on the crude product used. The 3-cyano-3,5,5-trimethylcyclohexanone yield is thus 96.7% and the isophorone selectivity 99%. at a reaction temperature of 120° C is distilled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By following the same procedure as Example 20 (2nd step) except that 8.8 g of methyltriethylammonium methyl carbonate, 8.8 g of water, and 4.5 g of maleic anhydride were used, 10.6 g (yield of 100%) of methyltriethylammonium maleate was obtained. The content of monomethyl maleate was less than 0.15 and the contents of impurity ions were all less than 1 ppm.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By following the same procedure as Example 20 (2nd step) except that 8.8 g of methyltriethylammonium methyl carbonate, 8.8 g of water, and 4.5 g of maleic anhydride were used, 10.6 g (yield of 100%) of methyltriethylammonium maleate was obtained. The content of monomethyl maleate was less than 0.15 and the contents of impurity ions were all less than 1 ppm.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into an autoclave equipped with a stirrer were charged triethylamine (1 mole), dimethyl carbonate (1.5 mole) and methanol (2.0 mole), which were reacted at a reaction temperature of 110° C. for 12 hours to obtain a methanol solution of methyltriethylammoniummethyl carbonate. To the thus obtained solution was added octylic acid (1 mole) followed by removing carbon dioxide gas evolved and methanol to obtain methyltriethylammonium octylate (C-1). Into an autoclave equipped with a stirrer were reacted at a reaction temperature of 110° C. for 12 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Next, the reaction solution of triethylmethylammonium methylcarbonate was reacted with 42% aqueous solution of fluoroboric acid at room temperature to obtain a reaction solution of triethylmethylammonium tetrafluoroborate. Then, the reaction solution of triethylmethylammonium tetrafluoroborate was added to n-butanol and subjected to rectification to remove methanol, dimethyl carbonate and water to obtain a tank bottom liquid containing crude triethylmethylammonium tetrafluoroborate. Then, the crude triethylmethylammonium tetrafluoroborate was purified by crystallization using n-butanol/water mixed solvent (85/15 in weight ratio) to obtain purified triethylmethylammonium tetrafluoroborate.

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Next, triethylamine and dimethyl carbonate were mixed with methanol as a solvent in a molar ratio of triethylamine/dimethyl carbonate=1/1.5, heated under a pressure of 1.5 MPa and at a temperature of 135° C. for 15 hours to carry out quaternarization until a conversion of 99.9% is achieved to obtain a reaction solution of triethylmethylammonium methylcarbonate. The conversion was measured by gas chromatography.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: From EP-A-291 074, it is known that dimethyl carbonate acts as a methylating agent during its reaction with an approximately stoichiometric amount of a tertiary amine. Thus, for example, the reaction of triethylamine with dimethyl carbonate gives the product triethylmethylammonium methyl carbonate in 89.9% yield (loc. cit., Example 1).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 622 g (4.5 mol) of isophorone in the presence of 4 g (0.021 mol) of triethylmethylammonium methylcarbonate there are added 288.3 g of a mixture of 3 mol of HCN and 1.5 mol of isophorone, over a period of 120 min and at a reaction temperature of 120° C. The HCN conversion at the end of the reaction is 99.9%. Following neutralization with 2.4g of H3PO4 the mixture is distilled. There are obtained 424.1 g of isophorone and 479.2 g of 3-cyano-3,5,5-trimethylcyclohexanone: the distillation residues weigh 12.8 g, this is equivalent to 1.4% based on the crude product used. The 3-cyano-3,5,5-trimethylcyclohexanone yield is thus 96.7% and the isophorone selectivity 99%. at a reaction temperature of 120° C is distilled