MX2008010473A - Process for preparing dihydroxytrialkylammonium halides and products thereof - Google Patents

Abstract

Compositions and methods for making compositions including a quaternary trialkylammonium halide compound are described. Compositions follow the formula (I):wherein the R1groups are each individually selected from alkyl groups having from 1 to 12 carbon atoms;wherein the R2, R3, and R4groups are each individually selected from hydrogen, hydroxide, alkyl groups having from 1 to 12 carbon atoms, and hydroxy alkyl groups having from 1 to 12 carbon atoms;wherein y ranges from O to 12;wherein X-is selected from fluoride, chloride, bromide, and iodide;wherein the quaternary trialkylammonium compound is present in an amount of at least 90 wt. percent;and wherein the composition comprises not greater than 4000 ppm of a trialkylamine or protonated form thereof.

Description

PROCESS FOR PREPARING HALU ROS DE DI H IDROXITRIALQUI LAMONIO AND PRODUCTS THEREOF PREVIOUS RELATED APPLICATIONS This application claims priority to the provisional US application no. 60/73, 536 filed on February 5, 2006 entitled "Process for Preparing Dihydroxytrialkylammonium Halides and Products Thereof" (Process for preparing dihydroxytrialkylammonium halides products thereof), which is incorporated herein by reference in its entirety.

TECHNICAL FIELD The invention relates to quaternary trialkylammonium halide compositions and methods for making such compositions. Specifically, the embodiments of the invention provide compositions comprising a trialkylammonium quaternary halide compound following the formula: BACKGROUND OF THE I NVENTION The trialkylammonium quaternary compounds have a variety of commercial applications in the textile industry and in the personal care arena. Some of these compounds can also be used as anti-microbial agents; to modify fillers, fibers and surfaces; as thickening agents; and as conditioning agents. In many of these applications and uses, it is desirable to provide the quaternary trialkylammonium compound in a high purity form to ensure that undesirable effects of impurities are minimized. Conventional compositions either lack acceptable concentrations of the quaternary trialkylammonium compounds while possessing more or less harmless impurities, while other products may have higher concentrations of the trialkylammonium quaternary halide compounds but also possess undesirable amounts of more remarkable impurities . One such impurity is residual trialkylamine because they have a characteristically unpleasant odor. For example, the nose and human can detect a fishy odor when, such an amines, trimethylamine is present in concentrations as low as about 0.0023 ppm. In this manner, the trialkylammonium quaternary halides prepared from such trialkylamine precursors often possess offensive odors even when diluted in formulations. Accordingly, compositions having higher concentrations of quaternary trialkylammonium halide and reduced levels of impurities, as well as processes for preparing such compounds by more efficient methods, would be useful.

BRIEF DESCRIPTION OF THE INVENTION In some embodiments, the invention provides compositions comprising a trialkylammonium quaternary halide compound following the formula: wherein the R1 groups are each individually selected from the group consisting of alkyl groups having from 1 to 1 2 carbon atoms; wherein the groups R2, R3 and R4 each individually selected from the group consisting of hydrogen, hydroxide, alkyl groups having from 1 to 12 carbon atoms, and alkyl hydroxy groups having from 1 to 12 carbon atoms; where y varies from 0 to 1 2; wherein X "is selected from the group consisting of fluoride, chloride, bromide and iodide, wherein the quaternary trialkylammonium compound is present in an amount of at least 90 weight percent, and wherein the composition comprises no more than 4000 pm of a trialkylamine or protonated form thereof Particular compositions have at least 99.5 weight percent 2,3-dihydroxypropyltrimethylammonium chloride and no more than 25 ppm trimethylamine, wherein the concentrations are determined based on the amounts of 2, 3-dihydroxypropyltrimethylammonium chloride and trimethylamine in the composition.Other modalities provide a method for making a quaternary trialkylammonium halide composition. In some embodiments, the method includes providing a hydroxylalkane-primary halo-di and a trialkine in a stoichiometric excess relative to the halo-dihydroxyalkane-primary under reaction conditions to provide an intermediate reaction mixture.; Reduce the pH of the intermediate reaction mixture; and isolating the quaternary trialkylammonium halide composition. In some embodiments, the method includes a method for making a 2,3-dihydroxyproyltrimethylammonium chloride composition. Methods for making 2, 3-dihydroxypropyltrimethylammonium chloride compositions include providing 3-chloro-1,2-dihydroxypropane and trimethylamine in a molar ratio of 1 to about 3 moles with respect to 3-chloro-1,2-dihydroxypropane under reaction conditions to provide an intermediate reaction mixture; removing at least a portion of the remaining trimethylamine from the intermediate reaction mixture; and isolating the 2,3-dihydroxypropyltrimethylammonium chloride composition. In certain embodiments of the methods described herein, the method does not include heating the intermediate reaction mixture to remove one or more volatile components. In some embodiments, the method does not include heating the intermediate reaction mixture to remove volatile components when the reaction mixture has a pH of 8 or more.

DESCRIPTION OF MODALITIES OF THE I NVENCION In the following description, all figures described herein are approximate values, regardless of whether the word "around" or "approximately" is used in relation to it. They can vary by 1%, 2%, 5% and sometimes, 10 to 20%. Whenever a numerical range with a lower limit, RL and an upper limit, RU, is described, any figure that falls within the range is described in a specific way. In particular, the following figures within the range are described specifically: R = RL + k * (RU-RL), where k is a variable that varies from 1% to 1 00% with a 1% increase, is say, k is 1% up to 100% with an increase of 1%, that is, k is 1%, 2%, 3%, 4%, 5%; ... 50%, 51%, 52%, ... 95%, 96%, 97%, 98%, 99% or 100%. Moreover, any numerical range defined by two figures R as defined in the previous one is also described in a specific way. The process of the invention is widely applicable and is particularly useful for the preparation of 3-chloro-1,2-dihydroxypropyltrimethylammonium chloride from trimethylamine which reacted with 3-chloro-, 2-dihydroxypropane. Although the description is given partially in terms of that specific example for clarity, the invention is thus not limited. In this manner, embodiments of the invention provide a composition comprising a trialkylammonium quaternary halide compound following the formula: wherein the R1 groups are each individually selected from the group consisting of alkyl groups having from 1 to 1 2 carbon atoms; wherein the groups R2, R3 and R4 are each individually selected from the group consisting of hydrogen, hydroxide, alkyl groups having from 1 to 12 carbon atoms, and hydroxy alkyl groups having from 1 to 1.2 carbon atoms. carbon; wherein y varies from 1 to 1 2, preferably and varies from 0 to 6, more preferably and varies from 0 to 3, most preferably and is 1; wherein X "is chloride, wherein the quaternary trialkylammonium compound is present in an amount of at least 90 weight percent, and wherein the composition comprises no more than 4000 ppm of a trialkylamine. of quaternary trialkylammonium comprises at least 90 weight percent up to 1 00 percent of the composition.Compositions of other embodiments have higher concentrations of the trialkylammonium quaternary compounds, such as, 92.5 weight percent, 95 weight percent , 97.5 percent by weight, 99 percent by weight, 99.5 percent by weight, 99.95 percent by weight, 99.99 percent by weight, or 99.995 percent by weight of the trialkylammonium-quaternary compound in the composition.

Although the concentration of the trialkylamine in the compositions is usually no more than about 4000 ppm, other compositions have a lower concentration of the trialkylamine. In some embodiments, the trialkylamine concentration is less than about 4000 ppm, less than about 3000 ppm, less than about 2500 ppm, less than about 2000 ppm, less than about 1000 ppm, less than about 500 ppm, less than about 400 ppm. , less than about 300 ppm, less than about 200 ppm, less than about 100 ppm, less than about 50 ppm, less than about 25 ppm, less than about 10 ppm, less than about 5 ppm, less than about 1 ppm, lower than about 0.1 ppm, less than about 0.01 ppm, less than about 0.002 or less than about 0.001 ppm. In particular embodiments, the concentration of the trialkylamine or protonated form of the amine is present in an amount ranging from about 10 ppm to about 25 ppm, preferably about 1 ppm to about 10 ppm. In some compositions, the quaternary trialkylammonium compound is present in an amount of at least 95 weight percent; and wherein the composition comprises no more than 1000 ppm of the trialkylamine or protonated form thereof. In other embodiments, the quaternary trialkylammonium compound is present in an amount of at least 99.5 percent by weight and the composition comprises no more than 500 ppm of the trialkylamine or the protonated form thereof. In still other embodiments, the quaternary trialkylammonium compound is present in an amount of at least 99.5 percent by weight and the composition does not comprise more than 500 ppm of the trialkylamine or the protonated form of the trialkylamine. In still other embodiments, the quaternary trialkylammonium compound is present in an amount of at least 99.5% percent by weight and the composition comprises no more than 1 00 ppm, no more than 25 ppm, or no more than 10 ppm, of the trialkylamine or the protonated form thereof. In particular embodiments, the composition comprises at least 99.95 weight percent of the trialkylammonium quaternary compound and no more than 1 ppm of the trialkylamine or the protonated form thereof. It is envisaged that the compositions of embodiments of the invention may be combined with other components to provide a composition suitable for personal care uses. In this manner, the amounts or concentrations of the trialkylammonium quaternary compound and the trialkylamine compound in the composition can be determined as an absolute value in the composition or in relation to only the amounts of the trialkylammonium quaternary compound and the trialkylamine compound in the composition . The term "alkyl group" as used herein, is intended to include hydrocarbon containing groups having 1 to 12 carbon atoms including alkyl groups, substituted or branched alkyl groups, or substituted or branched aryl groups, in particular groups having from 1 to about 6 carbon atoms, such as methyl and ethyl groups. Thus, in some embodiments, each R1 group is individually selected from alkyl groups having from 1 to 12 carbon atoms, preferably 1 to about 6, more preferably 1 to 3 carbon atoms, most preferably 1 carbon atom. Likewise, where the groups R2, R3 and R4 are alkyl groups, are each individually selected from the group consisting of alkyl groups having from 1 to 12 carbon atoms, 1 to about 6, 1 to 3 carbon atoms, or 1 carbon atom. Thus, such alkyl groups may include substituted alkyl group, or aryl, in particular groups having from about 1 to about 6 carbon atoms. In some embodiments, R 2, R 3 and R 4 can be a hydroxyalkyl group having from 1 to 4 carbon atoms, preferably hydroxymethyl or hydroxyethyl groups; hydrogen or a hydroxyl group. Although some embodiments include any combination of alkyl groups such as groups R1, in particular modalities each group R1 is the same alkyl group, for example, providing a composition that includes a trimethylammonium-, triethylammonium- or tri-n-propylammonium compound. In particular compositions, the quaternary trialkylammonium compound is a 2,3-dihydroxypropyltrialkylammonium chloride or 3,4-dihydroxybutyltrialkylammonium chloride. Some compositions comprising 2,3-dihydroxypropyltrimethylammonium chloride are preferred.

Particular compositions provide 2,3-dihydroxypropyltrimethylammonium chloride, wherein the 2,3-dihydroxypropyltrimethylammonium chloride is present in an amount of at least 95 weight percent; and wherein the composition comprises not more than 1000 ppm of the triethylamine or protonated form thereof. In other compositions, the 2,3-dihydroxypropyltrimethylammonium chloride is present in an amount of at least 99.5 weight percent; and the composition comprises not more than 500 ppm of the trimethylamine or the protonated form thereof. In still other compositions, the 2,3-dihydroxypropyltrimethylammonium chloride is present in an amount of at least 99.5 percent by weight and wherein the composition comprises no more than about 250 ppm, not more than about 100 ppm., not more than about 50 ppm, not more than about 25 ppm, not more than about 10 ppm, not more than about 5 ppm, not more than about 1 ppm, not more than about 0.1 ppm, not more than about 0.002 ppm, not more than about 0.001 ppm of the trimethylamine or the protonated form thereof, in particular trimethylamine. Some compositions comprise at least 99.9 percent by weight, 99.95, 99.99 or 99.995 percent by weight of 2,3-dihydroxypropyltrimethylammonium chloride and not more than 1 ppm of the trimethylamine or the protonated form thereof, in particular trimethylamine. The analysis of the trialkylamine concentration can be carried out as follows. A Hewlett Packard Agilent 6890 gas chromatograph with a CP Volamine column of 30 m x 0.32 mm x 5 μ? (They vary) was fixed to provide a heating profile of 50 ° C (5 min retention) followed by jumping at 260 ° C at 20 ° C / min (2.5 min retention) for a total run time of 1 8 minutes using constant pressure mode and an initial flow of 1.9 ml / min. The nominal initial pressure is 0.703 kg / cm2 (1 0 psi) and the linear velocity is 33 cm / s using helium as the carrier gas. The slit entry mode with a slit ratio of 21 .3: 1 and a slit flow of 40 ml / min is used at an inlet temperature of 270 ° C and a total inlet flow of 44.3 ml / min. A Tekmar upper space autosampler operating at a head space pressure of 1. 0545 kg / cm2 (1 5 psi), a platen temperature of 75 ° C is used to provide a 230 μ sample. The sample equilibrium time is adjusted to 5 min. The transfer line temperature, needle temperature, and injection valve / circuit temperature are set at 200 ° C. A flame ionization detector operating at 250 ° C, a hydrogen flow of 40 ml / min, an air flow of 450 ml / min and a nitrogen gas at a flow of 45 ml / min is used to detection.

Samples are prepared by weighing approximately 1 gram of sample in a vial of upper space and recording the weight. Each sample is prepared in duplicate, one for direct analysis and one for standard addition of a standard calibration mixture. Approximately 0.5 grams of trisodium phosphate is added to each sample to facilitate the volatilization of the amine impurities. Five ml of water are added to each sample and the vial is covered with a corrugated top cap.

The analysis of the quaternary trialkylammonium compound can be carried out by High Performance Liquid Chromatography (HPLC) according to the following procedure. An HPLC unit including an Agilent model pump G 1 310A, Agilent degasser model G1322A, and an annual VIVI ACU 1050 Injector is used. The column is a Radial-PAC cartridge, 8 mm x 10 cm, from Water Nova-pak C-18. the detection is achieved by means of an Agilent model G 1 362A RID (refractive index). HP Chemstation is used for integration. The normal sample size is 75 μ ?. The flow is set at 0.8 ml / min. The mobile phase comprises 1/2 PIC (Paired ion chromatography), prepared as 71.50 g of sodium perchlorate, anhydrous, 3.98 g of octane sulfonic acid (sodium salt), 1 800 g of distilled water and 200 g of methanol The samples were diluted to 1 weight percent in mobile phase before injection. Another concentration can be used whenever the concentration is suitable for detection. In other embodiments, the invention provides a method for making a quaternary trialkylammonium halide composition. In particular embodiments, the method includes providing a halo-dihydroxyalkane-primary and a trialkylamine in a stoichiometric excess relative to the halo-dihydroxyalkane-primary under reaction conditions to provide an intermediate reaction mixture; reduce the pH of the intermediate reaction mixture; and isolating the quaternary trialkylammonium halide composition by crystallization with a polar organic solvent. In some embodiments, the halo-dihydroxyalkane-primary is selected from the group consisting of halo-dihydroxyalkane-primary following the formula: wherein the groups R2, R3 and R4 are each individually selected from the group consisting of hydrogen, hydroxide, alkyl groups having from 1 to 12, in particular 1 to about 6, carbon atoms, alkyl hydroxy groups having from 1 to 1 2 , in particular 1 to about 6, carbon atoms; wherein y ranges from 0 to 12, preferably 0 to approximately 6, 0 to 3, or y is 1; wherein X is selected from the group consisting of fluoride, chloride, bromide and iodide. In some embodiments, the halo-dihydroxyalkane-primary is 3-chloro-1,2-dhydroxypropane. The trialkylamine can be selected from any desirable amine by having alkyl groups selected individually from alkyl groups having from 1 to 1 2, in particular 1 to about 6 carbon atoms, in particular 1 to 3 carbon atoms, more particularly 1 carbon atom. Other suitable alkyl groups can be substituted or branched alkyl groups, or substituted or branched aryl groups, in particular groups having from 1 to 12 carbon atoms, in particular 1 to about 6 carbon atoms, more particularly 1 to 4 carbon atoms. Particularly suitable trialkylamines include trimethylamine, triethylamine and tri-n-propylamine, dimethyl dodecylamine, tri-n-butylamine, tri-n-hexylamine, dimethylmonoethylamine, dimethylmono-n-butylamine, dimethylcyclohexylamine, dimethyl-monoisopropylamine, methylethyl-n-propylamine, methylethyl-n-butylamine , methyl dialkyl amines and other tertiary amines having linear, branched or cyclic hydrocarbon groups each independently containing from 1 to 1 to 2 carbon atoms. In particular embodiments, the halo-dihydroxyalkane-primary is 3-chloro-1,2-dihydroxypropane and the trialkylamine is trimethylamine. Whenever the trialkylamine is selected, it is usually provided in a stoichiometric excess. In particular embodiments, the term "stoichiometric excess" means that a molar ratio of at least 1 to about 3 moles of the trialkylamine is provided for each mole of the halo-dihydroxyalkane-primary. In a particular embodiment, the molar ratio of the trialkylamino to the halo-dihydroxyalkane-primary ranges from about 1.0 to about 1.5, preferably 1.1 to 1.3, of the trialkylamine are provided for each mole of the halo dihydroxyalkane-primary. Although any excess amount of the trialkylamine may be used, greater excesses of the amine may be difficult to remove. However, too much trialkylamine can result in incomplete reaction. Any suitable reaction condition can be used. Normally, the halo-dihydroxyalkane-primary is combined with an aqueous solution of the trialkylamine. However, any source of Reagent can be used. The reaction temperature can vary from about -20 ° C to about 25 ° C. Excess heat should be avoided. Normal reaction times vary from a few minutes to several days or more. The resulting mixture is treated to reduce its pH. The pH of the reaction mixture can be reduced by any desirable means. In some embodiments, the pH can be reduced by adding one or more acids. The acid should be selected to reduce the pH without degrading the desired products. Any organic or mineral acid can be used. In other embodiments, the pH is reduced by physically removing at least some of the trialkylamine in residual excess or other volatile components of the reaction mixture. In a particular embodiment, the alkylamine is removed by applying a reduced pressure to the reaction vessel or container. In other embodiments, the reaction mixture is sprayed with an inert gas to remove the trialkylamine. Any gas that is inert to the desired product can be used. In some embodiments, the inert gas is air, oxygen, nitrogen, argon or a gaseous alkane or alkene, and mixtures thereof can be used. However, normally, nitrogen is used as the inert gas, particularly when the trialkylamine is trimethylamine. Whenever the method is used, the pH is normally reduced to a value in the range from about 3 to about 10, preferably about 4 to about 9, or about 5 to about 8. In some embodiments, the pH is reduced to a value in the range of about 6 to about 7. In certain embodiments of the methods described herein, the method does not include heating the intermediate reaction mixture to remove one or more volatile components. In some embodiments, the method does not include heating the intermediate reaction mixture to remove volatile components when the reaction mixture has a pH of 8 or more. In other embodiments, the pH is less than 7.5, less than 7.0, less than 6.5, or less than 6.0 before a temperature greater than 25 ° C is applied. Lower pH values such as, 5.5, 5.0, 4.5, 4.0 or 3.0 can also be achieved before a temperature greater than 25 ° C is applied to the mixture. In some embodiments, the method does not include heating the intermediate reaction mixture to remove volatile components when the reaction mixture has an undesirable level of trialkylamine., in particular where the amine is trimethylamine. In addition, in particular embodiments, the concentration of trialkylamine is about 5000 ppm or less, about 4000 ppm less, about 2000 ppm or less, or about 1000 ppm or less. In other embodiments, the concentration of trialkylamine is about 500 ppm or less, about 250 ppm or less, about 100 ppm, about 50 ppm or less, about 25 ppm or less, or about 10 ppm or less before a temperature greater than 25. ° C is applied to the mixture. In such embodiments, lower concentrations of trialkylamine are generally beneficial.

Isolating the quaternary trialkylammonium halide composition can be carried out by treatment with any suitable solvent. In particular embodiments, the solvent is a polar organic solvent, such as a halogenated hydrocarbon solvent, such as methylene chloride, or tetrahydrofuran. In other embodiments, the solvent is selected from the group consisting of alcohols having from 3 to 20 carbon atoms. Particularly useful alcohols include propanol, isopropanol, butanols and hexanols. Isopropanol is particularly useful. Once the solvent has been selected, the precipitation of the quaternary trialkylammonium halide from the intermediate reaction mixture and the polar organic solvent can be induced by any suitable means. In some embodiments, precipitation is induced upon the addition of the polar organic solvent. In other embodiments, the mixture may be cooled until precipitation occurs. In some embodiments, the polar organic solvent is recovered and reused to recover additional portions of the quaternary trialkylammonium halide composition in a subsequent isolation step of the method to make the compositions as described herein. In some embodiments, a previously isolated quaternary trialkylammonium halide composition glass seed is added to facilitate crystallization. In some embodiments, the isolation of the polar organic solvent is performed when the concentration of trialkylamine, such as trimethylamine, is present at an acceptable low level. In this way, in particular modalities, the concentration of trialkylamine is about 5000 ppm or less, about 4000 ppm or less, about 2000 ppm or less, or about 1000 ppm or less. In other embodiments, the trialkylamine concentration is reduced to about 500 ppm or less, about 250 ppm or less, about 100 ppm, about 50 ppm or less, about 25 ppm or less, about 10 ppm, or about 1 ppm or less before of the insulation with the polar organic solvent. In such modalities, lower concentrations of trialkylamine are generally beneficial. In some embodiments, isolating the quaternary trialkylammonium halide further includes 1) separating the quaternary trialkylammonium halide precipitated from the remaining components of the reaction mixture and polar organic solvent and 2) drying the quaternary trialkylammonium halide. Any known method for separating can be used. Normally, the mixture is filtered to separate the precipitated quaternary trialkylammonium halide for the remaining components.

In particular embodiments, the invention provides a method for making a 2,3-dihydroxypropyltrimethylammonium chloride composition, wherein the method comprises providing 3-chloro-1,2-dihydroxypropane and trimethylamine in a molar ratio of 1 to about 3 moles with with respect to 3-chloro-1,2-dihydroxypropane under reaction conditions to provide an intermediate reaction mixture; removing at least a portion of the remaining trimethylamine from the intermediate reaction mixture; and isolating the composition of 2,3-dihydroxypropyltrimethylammonium chloride with a polar organic solvent, in particular an alcohol having 3 to about 20 carbon atoms, such as isopropyl alcohol.

The following example exemplifies one embodiment of the invention. It does not limit the invention as described otherwise and claimed herein. All figures in the example are approximate values.

EXAMPLE 1 251 ml of 3-chloro-1,2-dihydroxypropane was added to a round bottom flask equipped with a stir bar, thermometer and condenser. 837 ml of 25% aqueous trimethylamine were added to the reactor while stirring. The solution was allowed to stir for 1 6 hours at 1 5 ° C. The solution was sprayed with nitrogen for six days during which the pH decreases from about 1 1 to about 6. The solution was placed under reduced pressure of about 25 inches of Hg for 24 hours at 65 ° C. The solution was then placed under reduced pressure of 30 inches of Hg for eight hours at 65 ° C. The solution was allowed to stand at ambient conditions for 48 hours. The solution was then placed under reduced pressure of 30 inches of Hg for four hours at 65 ° C. 200 ml of isopropanol were added to the solution and the product crystallized. The product was filtered and placed in a dry nitrogen box for 24 hours and then in a vacuum oven at about 0 ° C and under reduced pressure of 26 inches of Hg with a nitrogen sweep for 36 hours. The product was placed in a dry nitrogen box for 24 hours. The product was analyzed by trimethylamine via GC upper space analysis and had 3.2 ppm trimethylamine. Analysis by H PLC showed 1 00.0% purity of 2, 3-d ihydroxypropyltrimethylammonium chloride.

EXAMPLE 2 1 1 0.5220 g of 3-chloro-21,2-dihydroxypropane was added to a 2 I laboratory beaker. 500 ml of 25% aqueous trimethylamine were added to the beaker. The solution was allowed to stir for 1.5 hours at room temperature. The solution was adjusted to pH using concentrated hydrochloric acid at a pH of 6.5. The solution was placed under reduced pressure of 30 inches of Hg for thirty minutes at 65 ° C. The product was analyzed by trimethylamine via GC top space analysis and had < 1 ppm trimethylamine.

EX EMPLO 3 251 ml of 3-chloro-1,2-dihydroxypropane were added to a round bottom flask equipped with a stir bar, condensing thermometer. 837 ml of 25% aqueous trimethylamine was added to the reactor while stirring. The solution was allowed to stir for 44 hours at 1 5 ° C. The solution was flushed with nitrogen for 1 3 days during the time that the pH decreased from about 1 1 to about 6. 200 ml of methanol were added to 400 ml of reaction solution and placed under reduced pressure of 30 inches. of Hg for four hours at 65 ° C. 200 ml of isopropanol was added to the solution. The solution was then placed under pressure reduced by 30 inches of Hg for two hours at 65 ° C. The solution was allowed to stand at room conditions for 16 hours. The solution was then placed under reduced pressure of 30 inches of Hg for five hours at 65 ° C. The solution was allowed to stand at room conditions for 16 hours. Then the solution was placed under reduced pressure of 30 inches of Hg for two hours at 65 ° C. 200 ml of isopropanol were added to the solution and the product crystallized. The product was filtered and placed in a dry nitrogen box for 24 hours. Subsequently the sample was placed in a vacuum oven at approximately 60 ° C and reduced pressure of 26 inches of Hg with a nitrogen sweep for 36 hours. The product was placed in a dry nitrogen box for 24 hours. The product was analyzed by trimethylamine via GC space analysis and had 4.0 ppm of trimethylamine. HPLC analysis shows 10.0% purity of the 2,3-dihydroxypropyltrimethylammonium chloride.

EJ EMPLOY COM EMPIRE 4 Example 8 of the European patent 0 257 61 9 was reproduced using the information described herein. 40 ml of 30 percent w / v of an aqueous solution of trimethylamine is added to 10.40 g of 3-chloro-1,2-propanediol. After reacting for 2 hours at room temperature, the reaction mixture at room temperature, the reaction mixture is evaporated to dryness to produce the product. Analysis of the upper space using the method described herein indicates that the composition has more than 4240 ppm of trimethylamine.

Although the invention has been described with respect to a limited number of embodiments, the specific characteristics of a modality should not be attributed to other embodiments of the invention. No single modality is representative of all aspects of inventions. Moreover, there are variations and modifications of them. For example, embodiments of the compositions described herein are substantially or substantially free of any component that has not been expressly stated as contained herein. Other components may be present as long as the declared characteristics are met. In particular, it is envisioned that the compositions can be used in formulations thereby reducing the absolute concentrations of the quaternary trialkylammonium compound and residual trialkylamine or protonated form thereof. In this manner, the amounts or concentrations of the trialkylammonium quaternary compound and the trialkylamine compound or protonated form thereof in the composition can be determined in relation to only the amounts of the trialkylammonium quaternary compound and the trialkylamine compound (and / or protonated thereof) in such formulations. In some modalities, the methods described herein provide compositions having improved color. In addition, some embodiments of the methods described herein consist of or consist essentially of the steps listed. In other modalities, the steps are performed in a variety of chronological orders. The appended claims are intended to cover all those variations and modifications that fall within the scope of the invention.

Claims (26)

1. REVIVAL NAME IS 1 . A composition comprising: a trialkylammonium quaternary halide compound following the formula: wherein the R1 groups are each individually selected from the group consisting of alkyl groups having from 1 to 12 carbon atoms; wherein the groups R 2, R 3 and R 4 are each individually selected from the group consisting of hydrogen, hydroxide, alkyl groups having from 1 to 12 carbon atoms, and alkyl hydroxy groups having from 1 to 12 carbon atoms; where y varies from 0 to 12; wherein X "is selected from the group consisting of fluoride, chloride, bromide and iodide, wherein the quaternary trialkylammonium compound is present in an amount of at least 90 weight percent, and wherein the composition comprises no more than 4000 ppm of a trialkylamine or protonated form 2. The composition of claim 1, wherein the trialkylammonium quaternary compound is a 2,3- dihydroxypropyltrialkylammonium or a 3,4-dihydroxybutyltrialkylammonium chloride. 3. The composition of claim 1, wherein the quaternary trialkylammonium compound is 2,3-dihydroxypropyltrimethylammonium chloride. The composition of claim 1, wherein the quaternary trialkylammonium compound is 2,3-dihydroxypropyltrimethylammonium chloride and the trialkylamine is trimethylamine; wherein the 2,3-dihydroxypropyltrimethylammonium chloride is present in an amount of at least 95 weight percent; and wherein the composition comprises not more than 1000 ppm trimethylamine or protonated form thereof. The composition of claim 4, wherein the 2,3-dihydroxypropyltrimethylammonium chloride is present in an amount of at least 99.5 weight percent; and wherein the composition comprises not more than 500 ppm of trimethylamine or protonated form thereof. The composition of claim 5, wherein the 2,3-dihydroxypropyltrimethylammonium chloride is present in an amount of at least 99.5 weight percent; and wherein the composition comprises not more than 25 ppm of trimethylamine or protonated form thereof. The composition of claim 6, wherein the 2,3-dihydroxypropyltrimethylammonium chloride is present in an amount of at least 99.5 percent by weight; and wherein the composition comprises not more than 10 ppm of trimethylamine or protonated form thereof. 8. The composition of claim 7, wherein the chloride of 2,3- Dihydroxypropyltrimethylammonium is present in an amount of at least 99.9 percent by weight; and wherein the composition comprises not more than 1 ppm of trimethylamine or protonated form thereof. The composition of claim 1, wherein the concentrations are determined based on the amounts of the trialkylammonium quaternary halide and the trialkylamine or protonated form thereof in the composition. 10. A composition comprising at least 99.5 weight percent of 2,3-dihydroxypropyltrimethylammonium chloride and not more than 25 ppm of trimethylamine or protonated form thereof, wherein the concentrations are determined based on the amounts of sodium chloride. , 3-dihydroxypropyltrimethylammonium and trimethylamine in the composition. eleven . A method for making a quaternary trialkylammonium halide composition, wherein the method comprises: a) providing a halo-dihydroxyalkane-primary and a trialkylamine in a stoichiometric excess relative to the halo-dihydroxyalkane-primary under reaction conditions to provide a mixture of intermediate reaction; b) reducing the pH of the intermediate reaction mixture by removing at least some trialkylamine in residual excess or other volatile components by applying a reduced pressure or by spraying with an inert gas; and c) isolating the quaternary trialkyl ammonium halide composition with a polar organic solvent, the trialkyl ammonium quaternary halide composition having a concentration of trialkylamine of 4000 ppm or less. The method of claim 1, wherein the halo-dihydroxyalkane-primary is selected from the group consisting of halo-dihydroxyalkane-primary following the formula: wherein the groups R2, R3 and R4 are each individually selected from the group consisting of hydrogen, hydroxide, alkyl groups having from 1 to 12 carbon atoms, and alkyl hydroxy groups having from 1 to 12 carbon atoms; where y varies from 0 to 12; wherein X is selected from the group consisting of fluoride, chloride, bromide and iodide. The method of claim 1, wherein the halo-dihydroxyalkane-primary is 3-chloro-1,2-dihydroxypropane and the trialkylamine is trimethylamine. The method of claim 1, wherein the stoichiometric excess is a molar ratio of at least 1 to about 3 moles of the trialkylamine to the halo-dihydroxyalkane-primary. The method of claim 1, wherein the molar ratio of the trialkylamine to the halo-dihydroxyalkane-primary varies from about 1.0 to about 1.5. 16. The method of claim 1, wherein the organic solvent polar is selected from the group consisting of alcohols having from 3 to 20 carbon atoms. The method of claim 1, wherein the polar organic solvent is isopropyl alcohol. 18. The method of claim 1, wherein reducing the pH includes reducing the pH to a value in the range from about 3 to about 10. The method of claim 1, wherein reducing the pH includes reducing the pH at a value in the range of from about 6 to about 7. The method of claim 1, wherein the reaction conditions in a) include a reaction temperature from -20 ° C to 25 ° C. twenty-one . The method of claim 1, wherein step b) further comprises an acid treatment. The method of claim 1, wherein isolating the quaternary trialkylammonium halide includes mixing the intermediate reaction mixture with the polar organic solvent and inducing the crystallization of the trialkyl quaternary halide from the intermediate reaction mixture and the solvent polar organic. The method of claim 22, wherein isolating the quaternary trialkyl ammonium halide further includes separating the quaternary trialkylammonium halide from the remaining components of the reaction mixture and the polar organic solvent and drying the quaternary trialkylammonium halide. 24. A method for making a 2,3-dihydroxypropyltrimethylammonium chloride composition, wherein the method comprises: a) providing 3-chloro-1,2-dihydroxypropane and trimethylamine in a molar ratio of 1 to about 3 moles with respect to 3- chloro-1,2-dihydroxypropane under reaction conditions to provide an intermediate reaction mixture; b) removing at least a portion of the remaining trimethylamine from the intermediate reaction mixture by removing at least some trialkylamine in residual excess or other volatile components by applying reduced pressure or spraying with an inert gas; and c) isolating the 2,3-dihydroxypropyltrimethylammonium chloride composition by precipitation with a polar organic solvent, the quaternary trialkylammonium halide composition isolated having a trialkylamine concentration of 4000 ppm or less. 25. The method of any of claims 1 to 24, wherein b) does not include heating the intermediate reaction mixture to remove one or more volatile components. 26. The method of any of claims 1 to 25, wherein it includes recycling or reclaiming the solvent and using the solvent in a subsequent isolation of the quaternary trialkylammonium halide composition.