A method for synthesizing 2-(2-aminoethoxy) ethanol, including the steps of producing 2-(2-phthalimidoethoxy) ethanol by reacting 5-tosyloxy-3-oxapentanol with potassium phthalate and converting the 2-(2-phthalimidoethoxy) ethanol to the 2-(2-aminoethoxy) ethanol by reacting the 2-(2-phthalimidoethoxy) ethanol with hydrazine monohydrate. Reacting the 2-(2-phthalimidoethoxy) ethanol with the hydrazine monohydrate may include forming a final mixture by adding the hydrazine monohydrate to a solution of 2-(2-phthalimidoethoxy) ethanol, refluxing the final mixture in a nitrogen atmosphere, extracting a second organic phase containing the 2-(2-aminoethoxy) ethanol from the final mixture using a second portion of chloroform, and purifying the 2-(2-aminoethoxy) ethanol from the second organic phase.

Ionic compounds containing an anion, and a cation having the following structural formula (1):
R.sup.1R.sup.2R.sup.3N.sup.+-(linker.sup.1)-O-(linker.sup.2)-(FC)  (1)
wherein: R.sup.1 and R.sup.2 either linear or branched alkyl groups or together form a N-heterocylic ring with the nitrogen atom to which they are joined; R.sup.3 is linear or branched alkyl group; linker.sup.1 and linker.sup.2 are alkylene chains or polyether chains; and the group FC is a fluorinated alkyl group, as well as an electrolyte material comprising such an ionic compound and a metal salt, and metal-air batteries using such an electrolyte material. The invention also relates to a metal-air battery containing an electrolyte material, wherein the electrolyte material comprises at least one ionic compound and a metal salt, and wherein at least one ionic compound contains an anion C.sub.nF.sub.2n+1COO.sup.− or C.sub.nF.sub.2n+1SO.sub.3.sup.−, where in each case n is at least 1 and at most 10.

Ionic compounds containing an anion, and a cation having the following structural formula (1):
R.sup.1R.sup.2R.sup.3N.sup.+-(linker.sup.1)-O-(linker.sup.2)-(FC)  (1)
wherein: R.sup.1 and R.sup.2 either linear or branched alkyl groups or together form a N-heterocylic ring with the nitrogen atom to which they are joined; R.sup.3 is linear or branched alkyl group; linker.sup.1 and linker.sup.2 are alkylene chains or polyether chains; and the group FC is a fluorinated alkyl group, as well as an electrolyte material comprising such an ionic compound and a metal salt, and metal-air batteries using such an electrolyte material. The invention also relates to a metal-air battery containing an electrolyte material, wherein the electrolyte material comprises at least one ionic compound and a metal salt, and wherein at least one ionic compound contains an anion C.sub.nF.sub.2n+1COO.sup.− or C.sub.nF.sub.2n+1SO.sub.3.sup.−, where in each case n is at least 1 and at most 10.

Disclosed is a method for crystallizing molecules having a molecular weight equal to or lower than about 500 Dalton in a gravity below about 0.01 g to about 0.000001 g as well as to crystalline molecules having a molecular weight equal to, or lower than, about 500 Dalton, prepared under microgravity conditions.

Disclosed is a method for crystallizing molecules having a molecular weight equal to or lower than about 500 Dalton in a gravity below about 0.01 g to about 0.000001 g as well as to crystalline molecules having a molecular weight equal to, or lower than, about 500 Dalton, prepared under microgravity conditions.

The invention is a herbicidal composition containing an alkanolamine salt of an dicamba capable of remaining as a single phase liquid over a period of at least 1 week and containing low amounts of water and high loadings of the salt. Such herbicidal compositions are capable of remaining liquid in the absence of high amounts of water, thereby enhancing their capacity to remain liquid over an extended period of time when exposed to environmental conditions to improve their effectiveness to transport the active salt through a leafy substrate and can reduce transportation costs by increasing the salt loading without compromising the stability of the composition.

The invention is a herbicidal composition containing an alkanolamine salt of an dicamba capable of remaining as a single phase liquid over a period of at least 1 week and containing low amounts of water and high loadings of the salt. Such herbicidal compositions are capable of remaining liquid in the absence of high amounts of water, thereby enhancing their capacity to remain liquid over an extended period of time when exposed to environmental conditions to improve their effectiveness to transport the active salt through a leafy substrate and can reduce transportation costs by increasing the salt loading without compromising the stability of the composition.

This application relates, in part, to novel salts represented by the following structure of Formula (1): ##STR00001##
wherein R.sup.1a is selected from the group consisting of hydrogen and optionally substituted alkyl (e.g., unsubstituted C.sub.1-6 alkyl, e.g., —CH.sub.3); R.sup.1b is optionally substituted alkyl (e.g., unsubstituted C.sub.1-6 alkyl, e.g., —CH.sub.3); each occurrence of R.sup.2 and R.sup.3 is independently selected from the group consisting of hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, and optionally substituted aryl; R.sup.2 and R.sup.3 can combine with each other to form optionally substituted cycloalkyl; each m and n is independently an integer ranging from 1 to 20 (e.g., m and n is independently an integer ranging from 1 to 5); and each of Q.sup.1.sup.⊖ and Q.sup.2.sup.⊖ is independently a counterion (e.g., each of Q.sup.1.sup.⊖ and Q.sup.2.sup.⊖ is independently a counterion selected from the group consisting of chloride, bromide, fluoride, iodide, acetate, carboxylate, hydrogen sulfate, nitrate, and phenolate, and sulfonate, e.g., chloride), and methods of making the same.

This application relates, in part, to novel salts represented by the following structure of Formula (1): ##STR00001##
wherein R.sup.1a is selected from the group consisting of hydrogen and optionally substituted alkyl (e.g., unsubstituted C.sub.1-6 alkyl, e.g., —CH.sub.3); R.sup.1b is optionally substituted alkyl (e.g., unsubstituted C.sub.1-6 alkyl, e.g., —CH.sub.3); each occurrence of R.sup.2 and R.sup.3 is independently selected from the group consisting of hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, and optionally substituted aryl; R.sup.2 and R.sup.3 can combine with each other to form optionally substituted cycloalkyl; each m and n is independently an integer ranging from 1 to 20 (e.g., m and n is independently an integer ranging from 1 to 5); and each of Q.sup.1.sup.⊖ and Q.sup.2.sup.⊖ is independently a counterion (e.g., each of Q.sup.1.sup.⊖ and Q.sup.2.sup.⊖ is independently a counterion selected from the group consisting of chloride, bromide, fluoride, iodide, acetate, carboxylate, hydrogen sulfate, nitrate, and phenolate, and sulfonate, e.g., chloride), and methods of making the same.

A compound of Formula II, or a salt, ester, solvate, hydrate or prodrug thereof: ##STR00001##
where: X.sup.1 is a branched or unbranched C.sub.1-10 alkyl, (CH.sub.2).sub.s—NH—(CH.sub.2).sub.t, (CH.sub.2).sub.s—O—(CH.sub.2).sub.t, or (CH.sub.2).sub.s—C(NH.sub.2)—(CH.sub.2).sub.v—NH—(CH.sub.2).sub.t, where s, t and v are each, independently an integer from 1 to 5; A and B are each, independently, C.sub.6-10aryl, C.sub.6-10aryl-C.sub.1-6alkyl, C.sub.3-9 heteroaryl, or C.sub.3-9heteroaryl-C.sub.1-6alkyl, each optionally substituted with 1, 2 or 3 independently selected R.sup.g groups; C and D are each, independently, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl-C.sub.1-6alkyl, C.sub.3-7 heterocycloalkyl, C.sub.3-7 heterocycloalkyl-C.sub.1-6 alkyl, C.sub.6-10aryl, C.sub.6-10aryl-C.sub.1-6alkyl, C.sub.3-9 heteroaryl, or C.sub.3-9heteroaryl-C.sub.1-6alkyl, each optionally substituted with 1, 2 or 3 independently selected R.sup.g groups; each R.sup.g is, independently, halogen, C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, hydroxyl, C.sub.1-6 alkoxy, C.sub.1-6 haloalkoxy, amino, C.sub.1-6alkylamino, or di-C.sub.1-6alkylamino; and n.sup.1 and p.sup.1 are each, independently, integers from 1 to 10.