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Pages in category "Acrylate esters"
The following 22 pages are in this category, out of 22 total. This list may not reflect recent changes (learn more).
|Wikimedia Commons has media related to Acrylate esters.|
The following 22 pages are in this category, out of 22 total. This list may not reflect recent changes (learn more).
1. Cyanoacrylate – Cyanoacrylates are a family of strong fast-acting adhesives with industrial, medical, and household uses. Cyanoacrylate adhesives have a shelf life if not used, about one year from manufacture if unopened. Cyanoacrylates include methyl 2-cyanoacrylate, ethyl-2-cyanoacrylate, n-butyl cyanoacrylate and 2-octyl cyanoacrylate, Octyl cyanoacrylate was developed to address toxicity concerns and to reduce skin irritation and allergic response. Cyanoacrylate adhesives are sometimes known generically as instant glues, power glues or superglues, the abbreviation CA is commonly used for industrial grades. The original patent for cyanoacrylate was filed in 1942 by Goodrich Company, as an outgrowth of a search for materials suitable for clear plastic gun sights for the war effort. In 1942, a team of scientists headed by Harry Coover Jr. stumbled upon a formulation that stuck to everything with which it came in contact. The team quickly rejected the substance for the application, but in 1951, while working as researchers for Eastman Kodak, Coover. The two realized the commercial potential, and a form of the adhesive was first sold in 1958 under the title Eastman #910. During the 1960s, Eastman Kodak sold cyanoacrylate to Loctite, which in turn repackaged and distributed it under a different brand name Loctite Quick Set 404, in 1971 Loctite developed its own manufacturing technology and introduced its own line of cyanoacrylate, called Super Bonder. Loctite quickly gained market share, and by the late 1970s it was believed to have exceeded Eastman Kodaks share in the North American industrial cyanoacrylate market, National Starch and Chemical Company purchased Eastman Kodak’s cyanoacrylate business and combined it with several acquisitions made throughout the 1970s forming Permabond. Other manufacturers of cyanoacrylate include LePage, the Permabond Division of National Starch and Chemical, together, Loctite, Eastman and Permabond accounted for approximately 75% of the industrial cyanoacrylate market. As of 2013 Permabond continued to manufacture the original 910 formula, in its liquid form, cyanoacrylate consists of monomers of cyanoacrylate molecules. Methyl-2-cyanoacrylate has a weight equal to 111.1, a flashpoint of 79 °C. Ethyl 2-cyanoacrylate has a weight equal to 125 and a flashpoint of >75 °C. To facilitate easy handling, an adhesive is frequently formulated with an ingredient such as fumed silica to make it more viscous or gel-like. More recently, formulations are available with additives to increase shear strength, such additives may include rubber, as in Loctites Ultra Gel, or others which are not specified. In general, cyanoacrylate is a resin that rapidly polymerises in the presence of water, forming long, strong chains. Because the presence of moisture causes the glue to set, exposure to normal levels of humidity in the air causes a thin skin to start to form within seconds, because of this cyanoacrylate is applied thinly, to ensure that the reaction proceeds rapidly for bonding
2. Ethyl acrylate – Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ester of acrylic acid. It is a liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers and it is also a reagent in the synthesis of various pharmaceutical intermediates. Ethyl acrylate is produced by acid-catalysed esterification of acrylic acid, which in turn is produced by oxidation of propylene and it may also be prepared from acetylene, carbon monoxide and ethanol by a Reppe reaction. Ethyl acrylate is used in the production of polymers including resins, plastics, rubber, Ethyl acrylate is a reactant for homologous alkyl acrylates by transesterification with higher alcohols through acidic or basic catalysis. In that way speciality acrylates are made accessible, e. g, copolymers of acrylic acid ethyl ester with ethene are suitable as adhesives and polymer additives, just like ethene vinyl acetate copolymers. Copolymers with acrylic acid increase the effect of liquid detergents. Owing to its tendency to polymerize, samples typically contain an inhibitor such as hydroquinone, examples are the hypnotic glutethimide or the vasodilator vincamin or more recent therapeutics such as the COPD agent cilomilast or the nootropic leteprinim. With dienes ethyl acrylate reacts as a dienophile in Diels-Alder reactions e. g. with 1. Ethyl acrylate is used as a flavoring agent. It has been found as a component in pineapples and Beaufort cheese and is a secondary component in vanilla flavor obtained from heat extraction of vanilla in amounts of up to 1 ppm. In such high concentrations it negatively affects the extracted aroma, regarding its toxicological data the targeted use of ethyl acrylate as aroma in consumer goods is questionable. It is an acute toxin with an LD50 of 1020 mg/kg, the International Agency for Research on Cancer stated, Overall evaluation, Ethyl acrylate is possibly carcinogenic to humans. In a study by the National Toxicology Program, increased incidences of squamous cell papillomas and carcinomas of the forestomach were observed in rats and mice exposed via gavage. However, the NTP recently determined that data were not relevant to human carcinogenicity since humans do not have a forestomach. One favorable safety aspect is that ethyl acrylate has good warning properties, in other words, the bad odor warns people of ethyl acrylates presence long before the concentration reaches a level capable of creating a serious health risk. CDC - NIOSH Pocket Guide to Chemical Hazards - Ethyl Acrylate
3. Methyl acrylate – Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a liquid with a characteristic acrid odor. It is mainly produced to make fiber, which is used to weave synthetic carpets. It is also a reagent in the synthesis of various pharmaceutical intermediates, the standard industrial reaction for producing methyl acrylate is esterification with methanol under acid catalysis. The transesterification is facilitated because methanol and methyl acrylate form a low boiling azeotrope, the patent literature describes a one-pot route involving vapor-phase oxidation of propene or 2-propenal with oxygen in the presence of methanol. Methyl acrylate can be prepared by debromination of methyl 2, 3-dibromopropanoate with zinc, methyl acrylate is formed in good yield on pyrolysis of methyl lactate in the presence of ethenone. Methyl lactate is a green chemical. Another patent describes the dehydration of methyl lactate over zeolites, the nickel tetracarbonyl-catalyzed hydrocarboxylation of acetylene with carbon monoxide in the presence of methanol also yields methyl acrylate. The reaction of formate with acetylene in the presence of transition metal catalysts also leads to methyl acrylate. Both, the alcoholysis of propiolactone with methanol as well as the methanolysis of acrylonitrile via intermediately formed acrylamide sulfate are also proven but obsolete processes. Methyl acrylate is after butyl acrylate and ethyl acrylate the third most important acrylic ester with an annual production of about 200,000 tons per year. Methyl acrylate is used for the preparation of 2-dimethylaminoethyl acrylate by transesterification with dimethylaminoethanol in significant quantities of over 50,000 tons / year, methyl acrylate is used as a comonomer in the polymerization with a variety of acrylic and vinyl monomers. In doing so it has a range of uses as ethyl acrylate. When using methyl acrylate as comonomer resulting acrylic paints are harder, copolymerizing methyl acrylate with acrylonitrile improves their melt processability to fibers, which could be used as precursors for carbon fibers. Acrylates are also used in the preparation of poly dendrimers typically by Michael addition with a primary amine, methyl acrylate is the precursor to fibers that are woven to make carpets. Owing to its tendency to polymerize, samples typically contain an inhibitor such as hydroquinone, methyl acrylate is a classic Michael acceptor, which means that it adds nucleophiles at its terminus. For example, in the presence of a base catalyst, it adds hydrogen sulfide to give the thioether,2 CH2CHCO2CH3 + H2S → S2 It is also a good dienophile and it is an acute toxin with an LD50 of 300 mg/kg and a TLV of 10 ppm
4. Ethyl cyanoacrylate – Ethyl cyanoacrylate, a cyanoacrylate ester, is an ethyl ester of 2-cyano-2-propenoic acid. It is a liquid with low viscosity and a faint sweet smell in pure form. It is the component of cyanoacrylate glues and can be encountered under many trade names. Super glue is believed to be ECA, the makers of Krazy Glue state on their website, The chemical name for Krazy Glue is ethyl cyanoacrylate. Mercury Adhesives is an example of an American made ECA and it is soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride. ECA polymerizes rapidly in presence of moisture, alternatively, it can be prepared by the ethoxycarbonylation of cyanoacetylene. Ethyl cyanoacrylate is used for gluing of various materials and it finds applications also in medicine, for liquid bandages and for suture-less surgery, but it is used less often than the less toxic n-butyl and octyl cyanoacrylates. Off-the-shelf non-medical-grade glues are unsuitable for applications, as they may contain solvents. After curing, the resin softens at temperatures above 150 °C. The service temperature of the joint is -54. +82 °C Its dielectric constant at 1 MHz is 3.33, in the U. S. the Threshold Limit Value for ECA is 0.2 ppm. Heating causes depolymerization of the cured polyECA, producing gaseous products strongly irritating to lungs, cyanoacrylate Methyl cyanoacrylate Butyl cyanoacrylate Octyl cyanoacrylate
5. Methyl methacrylate – Methyl methacrylate is an organic compound with the formula CH2=CCOOCH3. This colourless liquid, the ester of methacrylic acid is a monomer produced on a large scale for the production of poly. The compound is manufactured by methods, the principal one being the acetone cyanohydrin route. ACH is produced by condensation of acetone and hydrogen cyanide, the cyanohydrin is hydrolyzed in the presence of sulfuric acid to a sulfate ester of the methacrylamide, Methanolysis of this ester gives ammonium bisulfate and MMA. Although widely used, the ACH route coproduces substantial amounts of ammonium sulfate, 2CO + HCN → 2CCN 2CCN + H2SO4 → 2CCNH2. In fact the sulfate ester of the amide is produced as an adduct with sulfuric acid. This technology affords more than 3 billion kilograms per year, the economics of the ACH route have been heavily optimized. Given the scale of production, many methods have been developed starting from diverse two- to four-carbon precursors, ethylene is first hydroformylated to give propanal, which is then condensed with formaldehyde to produce methacrolein, The condensation is catalyzed by a secondary amine. This catalyst, caesium oxide on silica, achieves good selectivity to MMA from MeP, the formation of a small amount of heavy, relatively involatile compounds poisons the catalyst. The coke is easily removed and catalyst activity and selectivity restored by controlled, the reactor product stream is separated in a primary distillation so that a crude MMA product stream, free from water, MeP and formaldehyde, is produced. Unreacted MeP and water are recycled via the dehydration process. Pure MMA is produced from the crude MMA in a series of vacuum distillations and separations, in all cases, the separated streams are returned to the process, there is only one heavy ester purge stream. This is readily disposed of in an oxidizer with heat recovered for use in the process. In the fourth quarter of 2008, Lucite international commissioned its ‘first in class’ Alpha MMA plant based on Jurong Island in Singapore and this process plant is 30-40% cheaper to build and run than conventional systems, produces virtually no waste and the feedstocks can even be made from biomass. Metal oxides catalyse this process, 2CHCO2H + O → CH2=CCO2H + H2O Using Reppe chemistry, cH2=C–2 + O2 → CH2=C–CHO + H2O CH2=C–CHO + 1⁄2 O2 → CH2=C–COOH CH2=C–COOH + CH3OH → CH2=C–COOCH3 + H2O MAN can be produced by ammoxidation from isobutylene. This step is analogous to the route to acrylonitrile, a related commodity chemical. The raw material is tert-butanol, as in the direct oxidation method, CH2=C–CHO + CH3OH + 1⁄2 O2 → CH2=C–COOCH3 + H2O A process using isobutylene as a raw material has been commercially employed by Escambia Co. for a short period of time. Isobutylene is oxidized to provide α-hydroxy isobutyric acid by using N2O4, after esterification and dehydration MMA is obtained
6. Butyl cyanoacrylate – N-Butyl cyanoacrylate, a cyanoacrylate ester, is a butyl ester of 2-cyano-2-propenoic acid. It is a colorless liquid with a sharp, irritating odor. Its chief use is as the component of medical cyanoacrylate glues. It can be encountered under various names, e. g. MediBond, MediCryl, PeriAcryl, GluStitch, Xoin, Gesika, VetGlu, Vetbond, LiquiVet, Indermil, LiquiBand, Histoacryl, IFABond. The generic international nonproprietary name for NBCA is embucrilate, in medical and veterinary applications, NBCA, isobutyl cyanoacrylate, and octyl cyanoacrylate are commonly used. They are bacteriostatic and their use is usually painless, butyl esters provide stronger bond, but are rigid. Octyl esters, while providing weaker bond, are more flexible, blends of octyl cyanoacrylate and n-butyl cyanoacrylate are available which offer both flexibility and a strong bond. N-Butyl cyanoacrylate is used for embolization of cerebral arteriovenous malformations before their surgical treatment. NBCA is soluble in acetone, methyl ethyl ketone, nitromethane, NBCA in monomer form polymerizes rapidly in presence of ionic substances such as moisture, blood, or tissue fluids. NBCA has unique properties compared to other such as octyl cyanoacrylate or isoamyl cyanoacrylate. The polymerized form has excellent tensile strength and is effective in closing surgical or wound incisions. The closure of the wound or cut is quick and the product has inherently some valuable bacteriostatic properties, the cosmetic outcome of the closure is comparable or generally better than an equivalent suture substitute with least amount of scarring visible after three to six months. Also important is the properties of polymerized NBCA within the body. This property of NBCA has made it a very useful polymer to create various nanoparticles for delivery of drugs into the body with sustained release profiles, heating to higher temperatures causes pyrolysis and depolymerization of the cured glue, producing gaseous products strongly irritating to lungs and eyes. The medical applications of butyl cyanoacrylate include its use as an adhesive for lacerations of the skin, butyl cyanoacrylate has been used to treat arteriovenous malformations by application of the glue into the abnormality through angiography. In gastroenterology, butyl cyanoacrylate is used to treat bleeding gastric varices, the gastric varices are accessed by endoscopy, which uses a flexible fibre-optic camera to enter the stomach. They are injected with a needle inserted into the varix through the endoscope. Other sites of varices, including esophageal varices, duodenal varices, gastric varices have also been obliterated with recurrent injection treatment with butyl cyanoacrylate
7. Octyl cyanoacrylate – Octyl cyanoacrylate, a cyanoacrylate ester, is an octyl ester of 2-cyano-2-propenoic acid. It is a colorless liquid with a sharp, irritating odor. Its chief use is as the component of medical cyanoacrylate glues. In medical and veterinary applications, octyl cyanoacrylate, n-butyl cyanoacrylate and they provide rapid wound closure, are bacteriostatic, and their use is usually painless. Butyl esters provide a bond, but the glue is rigid. The octyl ester, while providing weaker bond, is more flexible, blends of octyl cyanoacrylate and n-butyl cyanoacrylate are available which offer both flexibility and a strong bond. It polymerizes rapidly in presence of moisture, heating to higher temperatures causes pyrolysis and depolymerization of the cured glue, producing gaseous products strongly irritating to lungs and eyes. Methyl cyanoacrylate Ethyl cyanoacrylate Butyl cyanoacrylate 2-Octyl cyanoacrylate
8. Methyl cyanoacrylate – Methyl cyanoacrylate is an organic compound that contains several functional groups, a methyl ester, a nitrile, and an alkene. It is a liquid with low viscosity. Its chief use is as the component of cyanoacrylate glues. It can be encountered under many trade names, methyl cyanoacrylate is less commonly encountered than ethyl cyanoacrylate. It is soluble in acetone, methyl ethyl ketone, nitromethane, MCA polymerizes rapidly in presence of moisture. Heating the polymer causes depolymerization of the cured MCA, producing gaseous products strongly irritant to lungs and eyes