University of Montana

Other

The Uab Research Foundation

Research Corporation Technologies, Inc.

A E Staley Manufacturing Company

Rivertop Renewables, Inc.

Donald E Kiely

Tyler Smith

Liang Light Chen

Kirk R Hash, Sr

Kylie Kramer-Presta

David W Morton

Kylie Kramer

Martin Seidman

Kirk Hash

Glenn Ponder

David P Shrout

Andy Carter

Jinsong Zhang

Tsu-Hsing Lin

Hydroxypolyamides, hydroxypolyamide products, and post-hydroxypolyamides are disclosed as gel forming agents. Hydroxypolyamides and post-hydroxypolyamides are prepared from known methods. Hydroxypolyamide products are produced from a modified polymerization procedure which utilizes strong base for deprotonation of ammonium salts from the esterification of stoichiometrically equivalent polyacid:polyamine salts. The hydroxypolyamide products are capable of gel formation at lower concentrations than hydroxypolyamides and post-hydroxypolyamides from the known methods of preparation, and are therefore superior gel forming agents.

Hydroxypolyamide gel forming agents

This invention relates to novel corrosion inhibitors which are capable of sequestering metal ions such as calcium and magnesium and are derived in part from renewable carbohydrate feedstocks. The corrosion inhibitors are mixtures containing one or more hydroxycarboxylic acid salts and one or more suitable oxoacid anion salts.

Corrosion inhibiting composition

A controlled nitric acid process employing oxygen and nitric acid as co-oxidants is used to oxidize organic compounds subject to nitric acid oxidation, to their corresponding carboxylic acids. Oxidation of some carbohydrates by this process can produce one or more of their corresponding acid forms. The process is carried out at moderate temperatures, typically in the range of 20&#xb0; C. to 45&#xb0; C. in a closed reactor, with oxygen gas being introduced into the reaction chamber as needed in order to sustain the reaction. Computer controlled reactors allow for careful and reproducible control of reaction parameters. Nitric acid can be recovered by a distillation/evaporation process, or by diffusion dialysis, the aqueous solution made basic with inorganic hydroxide, and the residual inorganic nitrate removed using a filtration (nanofiltration) device. The method eliminates issues of thermal control of the oxidation, release of nitrogen into the atmosphere, and post-reaction difficulties in the removal of nitric acid and inorganic nitrates.

Method of oxidation using nitric acid

Compositions which inhibit corrosion and alter the physical properties of concrete (admixtures) are prepared from salt mixtures of hydroxycarboxylic acids, carboxylic acids, and nitric acid. The salt mixtures are prepared by neutralizing acid product mixtures from the oxidation of polyols using nitric acid and oxygen as the oxidizing agents. Nitric acid is removed from the hydroxycarboxylic acids by evaporation and diffusion dialysis.

Hydroxycarboxylic acids and salts

A method of producing high molecular weight stereoregular head, tail-poly(alkylene D-glucaramides) is described. Amidoamino acids are esterified in cold alcohol and then polymerized in a protic solvent to form steroregular prepolymers. The prepolymers are then further polymerized by dissolving them in a solvent to form larger, purer postpolymers. Compositions of matter prepared using the subject method are also described.

High molecular weight stereoregular head-tail poly(glucaramides)

High molecular weight random polyhydroxypolyamides (PHPAs) are produced by creating prepolymers which are further polymerized. Random prepolymers are formed from a stoichiometrically molar balance (1:1) starting material. The starting material is a 1:1 stoichiometrically balanced esterified aldaric acid:alkylene or alkylene derived diammonium salt. Alternatively, the starting material is an esterified stoichiometrically balanced diacid:diamine salt and a N'-ammoniumalkyl (or alkyl derived)-D-aldaramic acid terminal carboxylate zwitterionic salt mixture. The starting materials are polymerized in a basic alcohol using a second amine. The polymerized material, or the random prepolymers, are isolated and then further polymerized in a solvent, typically a mixed solvent of an alcohol and non-alcohol, to obtain the high molecular weight PHPAs.

Method for preparing high molecular weight random polyhydroxypolyamides

A method for synthesizing and isolating an oxidation product is disclosed wherein nitric acid is reacted with an oxidizable reactant and the desired oxidized product is extracted using an organic solvent such as a dialkyl ether. The method permits the direct crystallization of aldaric acids such as glucaric acid and mannaric acid and eliminates the necessity of employing complicated, time consuming and wasteful neutralization/acidification steps.

Nitric acid removal from oxidation products

Rapid temperature rises which characterize carbohydrate-nitric acid oxidation reactions used to form carbohydrate-derived acids may be moderated and temperature control readily maintained by blowing a gas such as air, oxygen, nitrogen or the like into the reaction mixture as needed to control the temperature of the reaction. The more moderate reaction conditions afford higher yield of the desired product with a concomitant reduction of byproducts which may be difficult to remove and usually are unwanted as well. Upon completion the oxidation mixture is made basic (e.g. with an alkali metal base hydroxide or carbonate, ammonia or an amine) to a pH at which the the carboxyl group or groups of the product carbohydrate-derived acid are entirely in the salt form. The aqueous solution is then passed through an ion retardation resin column to recover the carbohydrate-derived salt, using water as the eluent. If desired, the carbohydrate-derived acid salt may then be recovered easily by removal of solvent water or by precipitation by addition of an water-miscible organic compound such as methanol, ethanol, acetone, isopropanol, etc.).

Oxidation process

The nitrogen in amides of aldonic and aldaric acids having 5 or 6 carbon atoms in the carbohydrate residue is available to support plant growth, i.e. the materials act as nitrogen fertilizers.

Carbohydrate acid amide plant fertilizers

Novel monomers are described which contain a glucaric acid unit linked through an amide bond formed between a carbonyl carbon of a D-glucaric acid and one of the amino nitrogens of a primary diamine as well as their alkali metal salts. These N-aminohydrocarbylene (or N-aminoheterohydrocarbylene)-D-glucaramidates may then be polymerized to form polyhydroxypolyamides and in particular stereoregular polyhydroxypolyamides.

Process for preparing poly (glucaramides)

Polymers of glucaric or xylaric acid with diprimary amines containing at least one heteroatom in the main chain form films when cast from aqueous solution and show adhesive properties. Unexpectedly, analogous polymers prepared using galactaric acid, an isomer of glucaric acid, do not form satisfactory films when cast from aqueous solution and exhibit poor or no adhesive properties. Copoly(aldaramides) comprising galactaric acid residues and either glucaric acid or xylaric acid residues, when prepared by reacting an equivalent weight of an activated galactarate with a product formed by reaction of two equivalents of a diprimary heterohydrocarbylenediamine with one equivalent of either an activated xylarate or glucarate also afford film-forming polymers which exhibit adhesive properties.

Growing community of inventors

Missoula, MT, United States of America

Donald E Kiely