Texaco Chemical Company

Texaco Inc.

Texaco Development Corporation

Huntsman Corporation

Arco Chemical Technology, L.p.

Huntsman Petrochemical Corporation

Jefferson Chemical Company, Inc.

Texaco Inc. (parent)

George P Speranza

Jiang-Jen Lin

Michael Cuscurida

Wei-Yang Su

Harold G Waddill

Robert L Zimmerman

Donald H Champion

Michael E Brennan

Robert A Grigsby, Jr

Edward T Marquis

Yu-Hwa E Sheu

William K Culbreth, Iii

David G Pottratz

Howard P Klein

James H Templeton

Ernest L Yeakey

John M Larkin

David R McCoy

Richard J Dominguez

Terry L Renken

Thomas H Austin

Edward E McEntire

Edward C Nieh

Carter G Naylor

Kathy B Sellstrom

Neal J Grice

Martin J Plishka

Bruce W Peterson

Richele T Howelton

John F Knifton

John R Sanderson

Roger G Duranleau

Richard J Clark

David C Alexander

Kenneth G McDaniel

Christopher S Henkee

Shailaja Madhusudhan Shirodkar

Carol A Triebel

A composition comprising an organic carbonate such as propylene carbonate and O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate, S-&lsqb;1,2-bis(ethoxycarbonyl)ethyl&rsqb;O,O-dimethylphosphorodithioate, or 6,7,8,9,10, 10-hexachloro-1,5,5 ,6,9,9 -hexahydro-6,9-methano-2,4,3-benzodioxathiepin-3-oxide, and methods thereof.

Water emulsifiable formulations

Disclosed is a one-step method for preparing N-alkylpiperazines which eliminates the initial preparation and isolation of piperazine which comprises reacting a carbonyl compound and an amine in the presence of hydrogen over a metallic hydrogenation-dehydrogenation catalyst from Group VIII of the Periodic Table such as, for example, nickel, copper, cobalt, chromium, palladium, platinum or ruthenium, alone or in combination with other Group VIII metals or transition metals selected from the group consisting of manganese, iron, zinc, copper and chromium.

Preparation of N-alkylpiperazines

Diamidopolyamines are prepared by reacting glutamic acid with two moles, per mole of glutamic acid, of a defined class of diamines, including oxyethyelene diamines, oxypropylenediamines, oxyethylene/propylene diamines, oxypropylene triamines, 1,2-diaminocyclohexane and isophorone diamine, whereby each of the carboxyl groups of the glutamic acid will react with an amine group of the amine reactant to thereby provide primary amine terminated amidopolyamines containing, internally, the unreacted primary amine group of the glutamic acid.

Amidopolyamines derived from amino-carboxylic acid

Described are carboxyl-terminated polyetheramides of the formula: ##STR1## where R is a moiety from an alcohol or hydroxy compound having a valence of k; R' is independently hydrogen or lower alkyl from 1 to 4 carbon atoms; R' is independently a straight or branched alkylene or aromatic moiety averaging from about 2 to 36 carbon atoms; x averages from about 2 to 100; z averages from about 20 to about 250; k averages from about 1 to 3; m is 0 or 1; and p is independently 5 to 11. Because the carboxyl-terminated polyetheramides are all carboxyl-terminated, they do not gel. They are expected to have good impact strength as well as differing solubilities depending on the polyetheramine incorporated.

Carboxyl-terminated polyetheramines

Bicyclo[4.3.0]1,4,7-triazanony-6-ene-5-one may be made easily, in good yield and in one step by reacting diethyl oxalate with a diethylene triamine. The bicyclo[4.3.0]1,4,7-triazanon-6-ene-5-one material made by this process may be used to selectively separate metal ions from solution, or complexed together with a metal ion act as a catalyst. Surprisingly, related bicyclic triazines do not show the ability to complex with metal ions and precipitate them from solution.

Bicyclo[4.3.0]1,4,7-triazanon-4-ene-one useful in the extraction of

Water soluble polyamides may be produced by reacting two different dicarboxylic acids with at least one low molecular weight poly(alkylene glycol) diamine and at least one relatively high molecular weight polyoxyalkylene diamine. One dicarboxylic acid may be of low molecular weight, such as adipic acid and the other of relatively high molecular weight such as C.sub.36 dimer acid. In one embodiment, some dimer acid proportion is preferred. The poly(alkylene glycol) diamine may include triethylene glycol diamine and tetraethylene glycol diamine. The polyoxyalkylene diamine should have at least some ethylene oxide residue therein; for example it may be a polyoxyethylene/polyoxypropylene diamine. The resulting polyamides have a desirable combination of properties, including high strength with water solubility, the latter making the materials easier to work with and very useful.

Water soluble polyamide from polyalkylene glycol diamines and

Macrocyclic oxamides may be made easily, in good yield and in one step by reacting an oxalic compound, such as oxalic acid or oxalic esters, with a diamine, where the amine groups are separated by at least five atoms. The oxalic compounds may include, but are not limited to such materials as dimethyl oxalate and diethyl oxalate. The diamines may include, but are not limited to such materials as alkylenediamines; polyalkylene glycol diamines; alkyl-bis-(aminoalkyl)amines; imino bis-(alkyl)amines; and N,N' bis-(aminoalkyl)-N,N'-dialkylalkylenediamines and bis-(aminoalkyl)piperazines; and mixtures thereof. The macrocyclic oxamides made by this process may be used to selectively separate metal ions from solution, or complexed together with a metal ion act as a catalyst.

Macrocyclic oxamides

A process for preparing phenoxyethanamines from phenols and 2-oxazolines in quantitative yields was discovered. Phosphoric acid hydrolyzes the amide intermediate from the phenol/2-oxazoline reaction without cleaving the amide at the ether linkage and without undesired aromatic ring substitution. Thus, yield to the desired phenoxyethanamines is often 98% or better, requiring no subsequent purification. In contrast, sulfuric and hydrochloric acids give these undesired side reactions. Phenoxyethanamines are useful in thermosetting resins, pharmaceuticals and as surfactants.

Preparation of phenoxyethanamines

Disclosed is a method for removing ammonia, organic amines and alkaline impurities from waste water which comprises using a partially spent ion exchange resin which no longer meets the purity requirements for the production of MTBE, washing the catalyst with water, contacting it with waste water for a an adequate period and removing the purified filtrate.

Method of removing alkaline materials from waste water

Amidamines of the following formula are described: ##STR1## where R is independently hydrogen or lower alkyl of 1 to 4 carbon atoms;

Polyamidopolyfunctional amine from lactam and ether amine

High molecular weight active polyoxyalkylene reaction product formed in two steps and containing urea or urethane and urea linkages are disclosed which contain as the principle reaction component, a diamine having the formula: ##STR1## or a diol having the formula: ##STR2## wherein R' independently represents hydrogen or methyl and x is a number having an average value of at least 1 to about 70 and a diisocyanate of the formula: ##STR3## an active amine selected from the group consisting of amine terminated triethylene glycol, amine terminated tetraethylene glycol, isophorone diamine, dipropylene triamine, or diethylene triamine.

Process for preparing polyoxyethylene amines with urea linkages

Poly(ethyleneoxy)amines, such as those having the structure:

Synthesis of diaza crown ethers

Block polyamido polyamine condensation products of an aromatic polycarboxylic acid component with a polyoxyalkylene polyamine component prepared by reacting the polycarboxylic acid component with an amount of the polyoxyalkylene polyamine component sufficient to react each carboxyl group with 1 mole of the polyoxyalkylene polyamine component. The polyoxyalkylene polyamine being selected from the group consisting of polyoxypropylene diamines, polyoxyethylene diamines, polyoxyethylene/oxypropylene diamines and polyoxypropylene triamines, and the aromatic polycarboxylic acid component being selected from the group consisting of C.sub.8 to C.sub.28 benzene dicarboxylic acids, benzene tricarboxylic acids, naphthalene carboxylates, hemimellitic acid, 1,1,3-trimethyl-3-phenylindan-4',5-dicarboxylic acid, trimellitic acid, and anhydrides and C.sub.1 to C.sub.4 alkyl esters thereof.

Aromatic polyoxyalkylene amidoamines

A process for preparing a polyurea reaction injection molded (RIM) elastomer is described. A hindered polyetherpolyamine is first obtained by reacting a polyol having two or more hydroxyl groups with an effective amount of long chain alkyl epoxide to give an at least partially hindered intermediate having hydroxyl terminations; and then aminating at least one of the hydroxyl terminations on the intermediate to primary amine groups to give an at least partially hindered polyetherpolyamine. The hindered polyetherpolyamine is then reacted with a polyisocyanate in the optional presence of a catalyst to give a polyurea RIM elastomer. The long chain alkyl group provides steric hindrance to the primary aliphatic amine group, which slows down the reactivity of the amine. The slower reactivity of the amine group is useful in RIM and RRIM compositions since it allows for longer shot or flow times, which in turn permit larger parts to be made from existing equipment.

Hindered amines to slow down reactivity in producing rim elastomers

Polyoxyalkylene diamines react with excess acrylate to form diesters which react with 2,2',6,6'-tetramethyl-4-aminopiperidines to give a product of formula 1, useful as photostabilizer for photosensitive materials. ##STR1##

Bis(2,2',6,6'-tetramethyl-4-aminoethyleneamidopiperidyl) polyoxyalkylene

Growing community of inventors

Austin, TX, United States of America

George P Speranza