Iowa State University Research Foundation Inc

U.S. Department of Energy

John G Verkade

Jiansheng Tang

Sameer Urgaonkar

Thyagarajan Mohan

JuHua Xu

Victor Shang-Yi Lin

Robert J Angelici

Carla Kern

Jennifer A Nieweg

Kuldeep Wadhwa

Xueqian Kong

Klaus Schmidt-Rohr

Chinta Reddy Venkat Reddy

Nandakumar Mecheril Valsan

Andrzej E Wroblewski

Jianseng Tang

An anion exchange membrane and fuel cell incorporating the anion exchange membrane are detailed in which proazaphosphatrane and azaphosphatrane cations are covalently bonded to a sulfonated fluoropolymer support along with anionic counterions. A positive charge is dispersed in the aforementioned cations which are buried in the support to reduce the cation-anion interactions and increase the mobility of hydroxide ions, for example, across the membrane. The anion exchange membrane has the ability to operate at high temperatures and in highly alkaline environments with high conductivity and low resistance.

Anion exchange membrane

A recyclable esterification or transesterification catalyst and methods for making and using the same are provided herein. The catalyst can be used to prepare biodiesel or methyl soyate from various feedstocks, including vegetable oils and animal fats. The catalyst can both esterify free fatty acids and transesterify mono-, di-, and triglycerides. The catalyst can also be combined with a metal oxide, and optionally calcined, prior to carrying out a catalytic reaction.

Porous silica and metal oxide composite-based catalysts for conversion of fatty acids and oils to biodiesel

A method is provided to couple an aryl halide to an alkyne comprising reacting a compound of the formula ArX, wherein Ar is a substituted or unsubstituted aryl group and X is I or Br, with a compound of the formula HC&#x2261;C&#x2014;Rwherein Ris a substituted or unsubstituted organic group, in the presence of an effective amount of a phosphine-free, oxime-free palladium catalyst; (C-C)alkyl N(OAc) or an alkali metal carbonate, to yield a compound of the formula Ar&#x2014;C&#x2261;C&#x2014;R, wherein the reaction is carried out in the absence of an organic amine or copper(I).

Palladium-catalyzed coupling of aryl halides with alkynes

Methods and compounds are provided for the formation of carbon-nitrogen or carbon-carbon bonds comprising reacting an amine or an aryl boronic acid with an aryl halide in the presence of a palladium catalyst, a base, and a compound of formula II: 

Triaminophosphine ligands for carbon-nitrogen and carbon-carbon bond formation

A method for producing sequenced reaction products comprising performing, in one pot, a first reaction at a lower temperature followed by a second reaction at a higher temperature in the presence of a catalyst system comprising a proazaphosphatrane in combination with a palladium compound is provided. In one embodiment, the first reaction is a double amination reaction and the second reaction is an arylation. Use of one pot and a single catalyst system for each set of sequential reactions is efficient and economical. Novel N,N-diarylaminostyrenes and N,N-diarylaminostilbenes are produced according to the methods described herein.

One pot sequential reactions and novel products produced thereby

A method is disclosed for deprotonating a compound comprising treating the compound with a base of the general formula: ##STR1## in the presence of a nitrile solvent; wherein R.sup.1, R.sup.2 and R.sup.3 are each individually H, (C.sub.1 -C.sub.15)alkyl, (C.sub.6 -C.sub.9)aryl, (C.sub.1 -C.sub.4)alkyl(C.sub.6 -C.sub.9)aryl, ((C.sub.1 -C.sub.4)alkyl).sub.3 Si, or (C.sub.6 -C.sub.9)aryl(C.sub.1 -C.sub.4)alkyl.

Prophosphatrane deprotonation of solvents

A process for preparation of new or previously known pyrrol derivatives is provided. The process involves reacting a nitroalkane or a nitroalkene with an isocyanoacetate in the presence of a prophosphatrane 'super base' to prepare the pyrrol compounds. Through production of new pyrrol compounds, new pyrrol derivatives such as dipyrromethanes and porphyrins may be synthesized. In addition, the high yields of pyrrol compounds produced according to the method of the invention provide for more efficient production of previously known dipyrromethane and porphyrin compounds. The invention further provides a mild, high yield process for de-esterification of esterified pyrrol and dipyrromethane compounds. The invention also provides a synthetic method for the production of high yields of oxazoles through reaction of an aryl halide or acid anhydride with an isocyanoacetate in the presence of a prophosphatrane 'super base'. The product oxazoles serve as intermediates for subsequent treatment to provide pharmaceutically interesting C-acyl-.alpha.-amino acid esters.

Preparation of pyrrol and oxazole compounds; formation of porphyrins and

A process for preparation of new or previously known pyrrol derivatives is provided. The process involves reacting a nitroalkane or a nitroalkene with an isocyanoacetate in the presence of a proprophosphatrane 'super base' to prepare the pyrrol compounds. Through production of new pyrrol compounds, new pyrrol derivatives such as dipyrromethane and porphyrin may be synthesized. In addition, the high yields of pyrrol compounds produced according to the method of the invention provide for more efficient production of previously known dipyrromethane and porphyrin compounds. The invention further provides a mild, high yield process for de-esterification of esterified pyrrol and dipyrromethane compounds. The invention also provides a synthetic method for the production of high yields of oxazoles through reaction of an aryl halide or acid anhydride with an isocyanoacetate in the presence of a prophosphatrane 'super base'. The product oxazoles serve as intermediates for subsequent treatment to provide pharmaceutically interesting C-acyl-.alpha.-amino acid esters.

Preparation of pyrrol and oxazole compounds: formation of

A method for the removal of sulfur from sulfur-bearing materials such as coal and petroleum products using organophosphine and organophosphite compounds is provided.

Mild desulfurization of sulfur-bearing materials

Neutral single-source molecular organic precursors containing tetradentate tripodal chelating ligands are provided that are useful for the preparation of films chemical vapor deposition. These complexes can be generally represented by the formula ##STR1## wherein 'M' is selected from the group consisting of a lanthanide, an actinide, a Group IIIA metal, a Group IIIA metalloid, a Group IVA metal, a Group IVA metalloid, a Group VA metal, a Group VA metalloid, a Group IIIB metal, a Group IVB metal, a Group VB metal, a Group VIB metal, a Group VIIB metal, and a Group VIIIB metal. The ligand 'Z', when present (k=1), is selected from the group consisting of hydrogen, halide, and a group bonded to 'M' through N, O, P, S, As, Si, or C. 'E.sub.c ' is N, P, or As, and m=0-1. When 'E.sub.t ' is N, P, or As, m=1. When 'E.sub.t ' is O, S, or Se, m=0. Each 'R.sup.1 ' is selected from the group consisting of hydrogen, (C.sub.1 -C.sub.20)alkyl, (C.sub.2 -C.sub.20)alkenyl, (C.sub.2 -C.sub.20)alkynyl, (C.sub.6 -C.sub.18)aryl, (C.sub.7 -C.sub.20)aralkyl, a (C.sub.5 .C.sub.18)heterocycle, and triorganosilyl. In --[C(R.sup. 2).sub.2 ].sub.n --, n=1-4, and each 'R.sup.2 ' is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, aralkyl, and a heterocycle.

Method of applying single-source molecular organic chemical vapor

Preparation of pyrrol and oxazole compounds: formation of porphyrins and

Method of removal of sulfur from coal and petroleum products

Neutral single-source molecular organic precursors containing tetradentate tripodal chelating ligands are provided that are useful for the preparation of films using chemical vapor deposition. These complexes can be generally represented by the formula ##STR1## wherein 'M' is selected from the group consisting of a lanthanide, an actinide, a Group IIIA metal, a Group IIIA metalloid, a Group IVA metal, a Group IVA metalloid, a Group VA metal, a Group VA metalloid, a Group IIIB metal, a Group IVB metal, a Group VB metal, a Group VIB metal, a Group VIIB metal, and a Group VIIIB metal. The ligand 'Z' can be present or absent, i.e., k=0-1, and is selected from the group consisting of hydrogen, halide, and a group bonded to 'M' through N, O, P, S, As, Si, or C. In the tetradentate tripodal chelating ligand 'E.sub.c ' is N, P, or As, and m=0-1. When 'E.sub.t ' is N, P, or As, m=1, and when 'E.sub.t ' is O, S, or Se, m=0. Each 'R.sup.1 ' is independently selected from the group consisting of hydrogen, (C.sub.1 -C.sub.20)alkyl, (C.sub.2 -C.sub.20)alkenyl, (C.sub.2 -C.sub.20)alkynyl, (C.sub.6 -C.sub.18)aryl, (C.sub.7 -C.sub.20)aralkyl, a (C.sub.5 -C.sub.18)heterocycle, and triorganosilyl. In --[C(R.sup.2).sub.2 ].sub.n --, n=1-4, and each 'R.sup.2 ' is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, aralkyl, and a heterocycle.

Growing community of inventors

Ames, IA, United States of America

John G Verkade