A treatment liquid composition for semiconductor production including: a quaternary ammonium hydroxide; and a first organic solvent dissolving the quaternary ammonium hydroxide, the first organic solvent being a water-soluble organic solvent having a plurality of hydroxy groups, wherein a water content in the composition is no more than 1.0 mass % on the basis of the total mass of the composition; contents of Na, Mg, Al, K, Ca, Ti, Cr, Mn, Fe, Ni, Cu, and Zn in the composition are each no more than 100 mass ppb on the basis of the total mass of the composition; and a content of Cl in the composition is no more than 100 mass ppb on the basis of the total mass of the composition.

A treatment liquid composition for semiconductor production including: a quaternary ammonium hydroxide; and a first organic solvent dissolving the quaternary ammonium hydroxide, the first organic solvent being a water-soluble organic solvent having a plurality of hydroxy groups, wherein a water content in the composition is no more than 1.0 mass % on the basis of the total mass of the composition; contents of Na, Mg, Al, K, Ca, Ti, Cr, Mn, Fe, Ni, Cu, and Zn in the composition are each no more than 100 mass ppb on the basis of the total mass of the composition; and a content of Cl in the composition is no more than 100 mass ppb on the basis of the total mass of the composition.

The invention pertains to a process for converting a feedstock comprising cyclic alkyleneureas into their corresponding alkyleneamines, comprising —a CO2 removal step in which cyclic alkyleneureas are converted into their corresponding alkyleneamines by reacting cyclic alkyleneureas in the liquid phase with water with removal of CO2, —an amine removal step wherein cyclic alkyleneureas are converted in a reactive separation process into their corresponding alkyleneamines by reaction with an amine compound selected from the group of primary amines or secondary amines which have a higher boiling point than the alkyleneamines formed during the process. It has been found that the combination of a CO2 removal step and an amine removal step makes it possible to convert alkyleneureas into the corresponding amines in an efficient manner in a high reaction rate.

The invention pertains to a process for converting a feedstock comprising cyclic alkyleneureas into their corresponding alkyleneamines, comprising —a CO2 removal step in which cyclic alkyleneureas are converted into their corresponding alkyleneamines by reacting cyclic alkyleneureas in the liquid phase with water with removal of CO2, —an amine removal step wherein cyclic alkyleneureas are converted in a reactive separation process into their corresponding alkyleneamines by reaction with an amine compound selected from the group of primary amines or secondary amines which have a higher boiling point than the alkyleneamines formed during the process. It has been found that the combination of a CO2 removal step and an amine removal step makes it possible to convert alkyleneureas into the corresponding amines in an efficient manner in a high reaction rate.

A process for preparing trans-enriched MDACH, including: distilling an MDACH starting mixture in the presence of an auxiliary, which is an organic compound having a molar mass of 62 to 500 g/mol, a boiling point at least 5° C. above the boiling point of cis,cis-2,6-diamino-1-methylcyclohexane, and 2 to 4 functional groups, each of which is independently an alcohol group or a primary, secondary or tertiary amino group. The MDACH starting mixture includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, based on the total amount of MDACH present in the MDACH starting mixture. The MDACH starting mixture includes both trans and cis isomers. Trans-enriched MDACH includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, where the proportion of trans isomers in the mixture is higher than the proportion of trans isomers in the MDACH starting mixture.

A process for preparing trans-enriched MDACH, including: distilling an MDACH starting mixture in the presence of an auxiliary, which is an organic compound having a molar mass of 62 to 500 g/mol, a boiling point at least 5° C. above the boiling point of cis,cis-2,6-diamino-1-methylcyclohexane, and 2 to 4 functional groups, each of which is independently an alcohol group or a primary, secondary or tertiary amino group. The MDACH starting mixture includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, based on the total amount of MDACH present in the MDACH starting mixture. The MDACH starting mixture includes both trans and cis isomers. Trans-enriched MDACH includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, where the proportion of trans isomers in the mixture is higher than the proportion of trans isomers in the MDACH starting mixture.

A process for preparing trans-enriched MDACH, including: distilling an MDACH starting mixture in the presence of an auxiliary, which is an organic compound having a molar mass of 62 to 500 g/mol, a boiling point at least 5° C. above the boiling point of cis,cis-2,6-diamino-1-methylcyclohexane, and 2 to 4 functional groups, each of which is independently an alcohol group or a primary, secondary or tertiary amino group. The MDACH starting mixture includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, based on the total amount of MDACH present in the MDACH starting mixture. The MDACH starting mixture includes both trans and cis isomers. Trans-enriched MDACH includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, where the proportion of trans isomers in the mixture is higher than the proportion of trans isomers in the MDACH starting mixture.

The present invention relates to a process for purifying ethylenediamine, in which a) a mixture comprising water (H2O), ethylenediamine (EDA) and N-methylethylenediamine (NMEDA) is introduced into a rectification column (NMEDA removal column), where the mixture introduced comprises at least the amount of water as required for the formation of a high-boiling azeotrope of EDA and water at the appropriate bottom temperature; and the EDA-comprising bottom product from the NMEDA removal column is introduced into a second rectification column (EDA dewatering column), wherein the pressure at the top of the EDA dewatering column is adjusted such that the boiling temperature of the mixture obtained at the top is 10° C. or higher than the bottom temperature of the NMEDA removal column, which comprises (i) partly or fully condensing the vapors from the top of the EDA dewatering column in a condenser which is cooled with a medium which is at least partly evaporated during the condensation and the vapor thus formed is used at least partly to heat the evaporator of the NMEDA removal column; and/or (ii) introducing the vapors from the top of the EDA dewatering column into the NMEDA removal column.

The present invention relates to a process for purifying ethylenediamine, in which a) a mixture comprising water (H2O), ethylenediamine (EDA) and N-methylethylenediamine (NMEDA) is introduced into a rectification column (NMEDA removal column), where the mixture introduced comprises at least the amount of water as required for the formation of a high-boiling azeotrope of EDA and water at the appropriate bottom temperature; and the EDA-comprising bottom product from the NMEDA removal column is introduced into a second rectification column (EDA dewatering column), wherein the pressure at the top of the EDA dewatering column is adjusted such that the boiling temperature of the mixture obtained at the top is 10° C. or higher than the bottom temperature of the NMEDA removal column, which comprises (i) partly or fully condensing the vapors from the top of the EDA dewatering column in a condenser which is cooled with a medium which is at least partly evaporated during the condensation and the vapor thus formed is used at least partly to heat the evaporator of the NMEDA removal column; and/or (ii) introducing the vapors from the top of the EDA dewatering column into the NMEDA removal column.

This is invention is related to processes for synthesis of levoamphetamine derivatives and novel intermediates thereby, and processes for using the same.