Abstract: In the process for the preparation of methyl methacrylate, the addition of aromatic diamine in an acidic environment reduces yellow color in the polymerized product.

Abstract: A 1,2-unsaturated carboxylic acid or its ester such as acrylic or methacrylic acid or its alkyl ester is purified to remove aldehyde impurities contained therein by treating the acid or its ester with a mercapto containing compound in the presence of an acid catalyst.

Abstract: In the recovery and purification of methacrylic acid or its esters produced by the vapor phase catalytic oxydehydrogenation of isobutyric acid or its esters the problem of downstream plugging is avoided by the inclusion of a small amount of surfactant in the gaseous effluent at or near the point of its condensation.

Abstract: Methods and compositions are provided for asymmetrically donating an oxygen atom to a pair of electrons to produce an asymmetric product. Specifically, a metal alkoxide is used as a catalyst, where the metal has a coordination number of at least four, and at least one, usually two, of the alkoxide groups bonded to the metal are bonded to asymmetric carbon atoms. The metal catalyst is employed in conjunction with a hydroperoxide and an alkanol having a functionality with a pair of electrons capable of accepting an oxygen atom. The resulting product is enriched in one enantiomer due to the enantioselective introduction of an asymmetric center or an enhanced rate of reaction of one of the enantiomers of a chiral alkanol.

Abstract: C.sub.1 -C.sub.4 -alkyl pentenoates are obtained from reaction mixtures which contain this and which are obtained by reacting butadiene, or a butadiene-containing hydrocarbon mixture, with carbon monoxide and a C.sub.1 -C.sub.4 -alkanol, in the presence of a cobalt carbonyl catalyst and a tertiary nitrogen base at elevated temperatures and under superatmospheric pressure by a process in which(a) the liquid reaction mixture freed from excess carbon monoxide is treated with hydrogen at elevated temperatures and under from 5 to 80 bar,(b) hydrocarbons are distilled off from the resulting liquid reaction mixture,(c) the C.sub.1 -C.sub.4 -alkyl pentenoate, the alkanol and the nitrogen base are then distilled off under reduced pressure, and(d) the C.sub.1 -C.sub.4 -alkyl pentenoate is obtained by fractional distillation from the distillate containing this compound, the alkanol and the tertiary nitrogen base.

Abstract: Methyl 4-pentenoate is isolated from mixtures containing this and methyl 3-pentenoate by a process in which from 0.25 to 0.4 part by weight of water is added per part by weight of methyl 4-pentenoate, and the azeotrope of methyl 4-pentenoate and water is distilled off.

Abstract: This invention pertains to processes for the preparation of nuclear substituted benzylic halides such as ortho-amino benzyl chlorides by reaction of substituted benzyl sulfoxides with nonoxidizing acid halides.

Abstract: Concentrated aqueous solutions of quaternization products of tertiary aminoalkyl esters or tertiary aminoalkylamides of acrylic or methacrylic acid are prepared by reaction of the corresponding esters or amides with an alkylating agent in a water-soluble ketone as solvent, by a process wherein, in order to isolate the quaternization product, an amount of water is added to the reaction mixture such that two phases form, and the lower aqueous phase, which contains the quaternization product in solution, is separated from the upper phase, which contains the ketone and residual alkylating agent.

Abstract: In purifying methyl methacrylate by feeding a feed mixture containing methanol, methyl methacrylate and 0.

Abstract: Methacrylamidopropyl trimethylammonium chloride and similar quaternized aminoalkyl esters or aminoalkylamides of acrylic acid or methacrylic acid are purified by extraction of an aqueous solution thereof with dichloromethane to remove impurities, such as allyl methacrylamide, which may be formed by a Hofmann degradation of the compounds.

Abstract: Unwanted halogen values are removed from liquid resin, organic or hydrocarbon material by adding particulate crystalline lithium aluminate compounds to the liquid material to act as a halogen scavenger, then separating the crystalline aluminate compound from the liquid material.

Abstract: A process for preparing esters which comprises reacting a polycarboxylic acid with an excess of alcohol and in the presence of an organotitanate catalyst, treating the crude mixture with a suitable chelate compound, removing the unreacted alcohol and hydrolyzing the treated titanium catalyst residues with steam, and recovering the purified ester by filtration.

Abstract: A process is provided for the continuous production of ethyl acrylate from ethylene and acrylic acid in the presence of sulfuric acid. The process includes the removal of impurities from the reaction system by passing minor portions of sulfuric acid residue from the process through a wiped-film evaporator whose initial sections are heated to a specific temperature range and whose last or withdrawal sections are cooled to a specific temperature range. The treated sulfuric acid residue is withdrawn from the reaction system. This treatment prevents foaming of the sulfuric acid residue. If foaming of the sulfuric acid residue occurs, the foamed residue can back up into the reaction system requiring a shutdown of the entire process. The improvement of this process is the passing of the ethyl acrylate product residue from the finishing distillation tower into the wiped-film evaporator at the same time that the sulfuric acid residue is being treated.

Abstract: The present invention provides an improvement in methods for preparing and processing readily polymerizable acrylate monomers. The improvement comprises employing phenyl-para-benzoquinone, 2,5-di-phenyl-para-benzoquinone, and mixtures thereof as process inhibitors. The process inhibitors are present in a concentration of about 50 to 3000 ppm, preferably about 250 to 2000 ppm, and most preferably about 500 ppm.

Abstract: Methods and compositions are provided for asymmetrically donating an oxygen atom to a pair of electrons to produce an asymmetric product. Specifically, a metal alkoxide is used as a catalyst, where the metal has a coordination number of at least four, and at least one, usually two, of the alkoxide groups bonded to the metal are bonded to asymmetric carbon atoms. The metal catalyst is employed in conjunction with a hydroperoxide and an alkanol having a functionality with a pair of electrons capable of accepting an oxygen atom. The resulting product is enriched in one enantiomer due to the enantioselective introduction of an asymmetric center or an enhanced rate of reaction of one of the enantiomers of a chiral alkanol.

Abstract: In a process for producing an acrylic or methacrylic ester by esterifying acrylic or methacrylic acid with a lower aliphatic alcohol having 1 to 3 carbon atoms in the presence of an acidic catalyst, the improvement which comprises(1) distilling the resulting esterification reaction mixture while feeding the acrylic or methacrylic ester into a distillation column from outside the system, thereby to yield as a distillate a mixture composed of the acrylic or methacrylic ester, water and the unreacted alcohol and being substantially free from acrylic or methacrylic acid, and (2) recycling the residue in the distillation column, from which the ester and water formed have been substantially removed, to the esterification reaction in such a proportion that the mole ratio of acrylic or methacrylic acid to the alcohol in the entire starting materials fed to the esterification reaction is kept at 1:0.5-1.0.

Abstract: In one of its embodiments this invention provides a process for recovering C.sub.4 -C.sub.6 dicarboxylic acid components contained in a waste byproduct stream derived from a reaction system in which adipic acid is produced by nitric acid oxidation of cyclohexanone/cyclohexanol.An important aspect of the process is the esterification and extraction of the C.sub.4 -C.sub.6 dicarboxylic acids in the aqueous byproduct stream with a mixture of C.sub.1 -C.sub.3 alkanol and C.sub.6 -C.sub.20 alkanol, and the subsequent recovery of di(C.sub.6 -C.sub.20 alkyl) esters of succinic acid, glutaric acid and adipic acid.In a broader aspect this invention provides a process for recovery of water miscible organic acid components contained in an aqueous solution as C.sub.6 -C.sub.20 alkyl esters of the organic acids.

Abstract: A process for preparing a methacrylic acid ester by reacting methacrylic acid with a lower aliphatic alcohol in the liquid phase using a solid acid catalyst at a molar ratio of alcohol to methacrylic acid of 1.2-3.0 and a reaction temperature of 70.degree.-100.degree. C. is improved by(1) extracting the unreacted alcohol from the reaction mixture with an aqueous solvent at a temperature of 25.degree. to 70.degree. C.,(2) removing the low boiling substances from the extraction residual mixture by distillation, whereby an organic residue is generated containing methacrylic acid ester and unreacted methacrylic acid, and(3) separating the unreacted methacrylic acid and the methacrylic acid ester by distillation.

Abstract: A process of removing unsaturated hydrocarbons containing at least one non-aromatic unsaturation from feedstreams which comprises contacting the feedstream with at least one of Cu.sub.2 O or Ag.sub.2 O and a fluorinated acetylacetonate of the formula ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 fluoroalkyl, C.sub.1 -C.sub.8 alkyl, C.sub.4 -C.sub.6 heterocycle containing O, S or N or C.sub.6 -C.sub.10 aryl, R.sup.2 is H or C.sub.1 -C.sub.6 alkyl with the proviso that R.sup.1 and R.sup.2 together with the carbons to which they are attached may be joined together to form a C.sub.6 ring and n is from 1 to 8, in an inert organic solvent.

Abstract: This invention provides an electrochemical process for the production of vinyl acetate from ethylene and anolyte acetic acid at a constant anodic half cell potential and under, ambient conditions of temperature and pressure.

Abstract: A method and apparatus for distilling readily polymerizable liquid such as readily polymerizable monomers without causing the formation of an undesirable polymerization product is disclosed. This distillation is effected by(a) vaporizing the polymerizable liquid from a liquid phase containing the same in an evaporator by externally heating the liquid phase;(b) converting the vapor of the polymerizable liquid to a superheated state by externally heating, and introducing the vapor of the polymerizable liquid to the inlet of a condenser, while the vapor is maintained at the superheated state; and, then,(c) condensing the vapor in the condenser, while a portion of the condensed fraction is circulated to the inlet of the condenser, whereby the condensation surface thereof is wetted.

Abstract: In a process for producing a 2-hydroxyalkyl acrylate or methacrylate which comprises esterifying acrylic or methacrylic acid with an alkylene oxide having 2 to 4 carbon atoms in the presence of an esterification catalyst and distilling the resulting reaction mixture in a distillation column, the improvement wherein the vapor of the ester monomer from the distillation column, while being maintained in the superheated state, is introduced into a condenser of the gas-liquid direct contact type whose inner wall corresponding to its gas inlet portion is kept at a temperature below the boiling point of the ester at the operating pressure, to contact it directly with a concurrently flowing spray liquid of the ester-precooled to a temperature below the boiling point of the ester at the operating pressure, whereby said vapor is condensed to a liquid at said temperature below the boiling point of the ester at the operating pressure.

Abstract: In a process for producing acrylic acid which comprises contacting with water an acrylic acid-containing reaction product gas which has been obtained by the catalytic vapor phase oxidation of an olefinic compound of a general formula, CH.sub.2 .dbd.CHX, wherein X represents at least one group selected from the group consisting of CH.sub.

Abstract: The level of hydrolyzable chloride-containing impurities in an isocyanatoalkyl ester of an organic carboxylic acid is reduced by reacting the impurities with a vicinal epoxide-containing compound and then fractionally distilling the mixture to recover the isocyanatoalkyl ester. As an example, crude 2-isocyanatoethyl methacrylate (IEM) in a methylene chloride solution containing 0.084 weight percent of hydrolyzable chloride is contacted with a diglycidyl ether of bisphenol A at 23.degree. C. This reaction mixture is then fractionally distilled to separate the IEM from the methylene chloride first cut and the epoxy resin residue. The hydrolyzable chloride level of the distilled IEM product is only 0.03 weight percent.

Abstract: In a process for purifying an ester with little contamination by catalytic metal components in a high yield which comprises treating an esterification reaction mixture with a basic substance, said esterification reaction mixture being obtained by reacting an organic carboxylic acid or its anhydride with an alcohol in the presence of an organometallic compound as an esterification catalyst, and purifying the product in a manner known per se; the improvement wherein prior to said treatment with the basic substance, water is added to the esterification reaction mixture and the mixture is heated.

Abstract: A normally liquid hydrocarbon having a minimum boiling point of about 425.degree. F. is utilized to provide the liquid seal in a vacuum pump which intakes a gaseous light ends stream resulting from a process for the production of ethyl acrylate by the reaction of ethylene with acrylic acid in the presence of a sulfuric acid catalyst. Upon contact in the vacuum pump, the gaseous light ends are partially absorbed into the normally liquid hydrocarbon, with the normally liquid hydrocarbon being recovered by fractionation.

Abstract: Triglyceride mixture is fractionated (on the basis of Iodine Value) utilizing selected surface aluminated silica gel adsorbent and selected solvent(s).

Abstract: Alkyl fatty carboxylate mixture is separated according to degree of unsaturation utilizing selected surface aluminated silica gel adsorbent and selected solvent(s).

Abstract: Alkyl fatty carboxylate mixture is separated according to degree of unsaturation utilizing selected permutite adsorbent and selected solvent(s).

Abstract: Planar organic molecules, such as divinylbenzene or para-dioxin molecules, are adsorbed from mixtures of planar and non-planar molecules, such as commercial divinylbenzenes containing non-planar ethylvinylbenzene, or commercial 2,4,5-T herbicide containing non-planar 2,4,5-trichlorophenoxyacetic acid, by partially pyrolyzed, macroporous, resinous polymer particles.

Abstract: The present invention relates to a method of purifying readily polymerizable high boiling vinyl monomers, in particular the acrylates and methacrylates of alkylene oxides and their ether and ester derivatives to obtain pure water white esters. The process involves flash evaporation of the preheated esters followed by condensation in the presence of polymerization inhibitors under specific conditions. The purified esters thus produced find use either as such or in the form of their copolymers in coatings, enamel paints, weather resistant finishes, adhesive compositions, as plasticizers, as lubricants for cellulose films and fibers, in magnetic tape recording media and as oil additives.

Abstract: The level of 2-oxazoline or an oxazine impurity in an isocyanatoalkyl ester of an organic carboxylic acid is reduced by (i) reacting the impurity with an organic acid chloride, a chloroformate, a thiochloroformate, a sulfonyl chloride, phosphoryl chloride, sulfuryl chloride or thionyl chloride and (ii) fractionally distilling the reaction mixture to recover the isocyanatoalkyl ester. As an example, crude 2-isocyanatoethyl methacrylate (IEM) containing 0.19 weight percent 2-isopropenyl-2-oxazoline (IPO) is contacted with terephthaloyl chloride for 0.5 hour at 90.degree. C. The reaction mixture is fractionally distilled to recover 97 weight percent of the IEM containing only 0.02 weight percent IPO.

Abstract: There is provided an improved continuous homogeneous catalytic carbonylation process wherein a mixed gas stream is removed from the carbonylation reactor, condensable liquids separated from said gas stream and said gas stream vented, the improvement comprising contacting said gas stream with a plurality of hollow fiber membranes selectively permeable to hydrogen under conditions substantially non-degrading of the membranes to generate a non-permeated gas stream of higher carbon monoxide content and recycling said non-permeated gas stream to the carbonylation process reactor. There is also provided for the recovery and recycle to the process of carbonylation products such as acetic or propionic acids by adsorption and removal from a solid adsorbent or absorption in a liquid absorbent.

Abstract: An improved method for separating an ester formed in a reaction mixture is disclosed. The method comprises controlling the ratio of organic acid and alcohol utilized and the removal of unreacted alcohol as an alcohol-ester azeotrope.

Abstract: Differential esterification or hydrolysis is utilized to effect separations of isomeric acids or esters.

Abstract: A process for separating an ester of a polyethanoid fatty acid and an ester of a monoethanoid fatty acid from a mixture comprising an ester of a polyethanoid fatty acid, an ester of a monoethanoid fatty acid and an ester of a saturated fatty acid which process comprises contacting the mixture at first adsorption conditions with a first adsorbent comprising an X or a Y zeolite containing a selected cation at the exchangeable cationic sites thereby selectively adsorbing the ester of a polyethanoid fatty acid and thereafter recovering the ester of a polyethanoid fatty acid by desorption with a desorbent material; removing from the first adsorbent a second mixture comprising an ester of a monoethanoid fatty acid and an ester of a saturated fatty acid; contacting the second mixture at second adsorption conditions with a second adsorbent comprising an X or a Y zeolite containing selected cations at the exchangeable cationic sites thereby selectively adsorbing the ester of a monoethanoid fatty acid and thereafter re

Abstract: Fatty acid ester mixture is separated according to degree of unsaturation utilizing particular resin adsorbent and particular solvent.

Abstract: Process for preparing acrylic monomers comprising reacting, in aqueos medium, amino alkyl esters of (meth) acrylic acid with a quaternizing agent wherein the aqueous solution obtained is washed with a water-insoluble solvent and the solvent thereafter removed. The quaternized monomers prepared are directly polymerizable to high molecular weight homopolymers or copolymers useful as cationic flocculants.This is a continuation of application Ser. No. 603,173 filed Aug. 8, 1975, now abandoned.

Abstract: The isomers of synthetic insect sex pheromones or their precursors are separated by selectively forming an inclusion complex with the E-isomer and urea or thiourea. In order for the E-isomer complex to form selectively it is necessry that the mono-olefin which forms the complex have a primary, linear chain of at least 7 atoms, a molecular diameter of 2.8-6A, and a polar functional group having transverse dimensions of less than 6A. Branching between the olefinic bond and the polar functional group is limited to methyl groups.

Abstract: New compounds containing tribromomethyl groups, of the general formula ##STR1## WHEREIN X is chlorine or bromine, R is hydrogen or methyl and R.sup.1 is hydrogen or a group of the formula --COO--CHX--CBr.sub.3 and a process for their preparation. The compounds may be used for the manufacture of homopolymers or copolymers which find diverse uses, eg. for the manufacture of moldings, coatings or adhesives. The compounds are manufactured by reacting the corresponding acid chlorides or acid bromides with equivalent amounts of tribromoacetaldehyde. The acid chlorides and bromides have the formula ##STR2## wherein X is chlorine or bromine, R is hydrogen or methyl and R.sup.2 is hydrogen or --COX. The reaction is carried out in the presence of from 0.1 to 10 per cent by weight of a Lewis acid, preferably AlBr.sub.3 or FeBr.sub.3, at from 0 to 80.degree. C., generally with reaction times of from 1 to 10 hours, preferably from 2 to 3 hours.

Abstract: A continuous process for the preparation of acrylic and methacrylic acid esters by conventional esterification, where sufficient substantially anhydrous product ester is added to the esterification reactor to satisfy the ester/alkanol and ester/water azeotropes, the low boiling azeotropes are recovered, thereby removing crude product ester, unreacted alkanol and water of esterification from the esterification reactor, while leaving substantially all the high-boiling unreacted acrylic or methacrylic acid in the reactor.

Abstract: A process for preparing a purified methacrylic acid ester from a crude methacrylic acid ester containing an isobutyric acid ester as an impurity, comprising the steps of azeotropically distilling the crude methacrylic acid ester in the presence of water to separate as the top distillate the isobutyric acid ester and water together with a small amount of the methacrylic acid ester and recover as the bottoms the greater part thereof, separating the distillate into aqueous and organic phases and further azeotropically distilling the separating organic phase in the presence of water to separate as the distillate the isobutyric acid ester and water together with a very small amount of the methacrylic acid ester and recover as the bottoms the remainder thereof, thereby obtaining the purified methacrylic acid ester.