Acrylic acid esters methyl acrylate

The polymeric products can be made to vary widely in physical properties through controlled variation in the ratios of monomers employed in thek preparation, cross-linking, and control of molecular weight. They share common quaHties of high resistance to chemical and environmental attack, excellent clarity, and attractive strength properties (see Acrylic ester polymers). In addition to acryHc acid itself, methyl, ethyl, butyl, isobutyl, and 2-ethylhexyl acrylates are manufactured on a large scale and are available in better than 98—99% purity (4). They usually contain 10—200 ppm of hydroquinone monomethyl ether as polymerization inhibitor. 

Chemical Designations - Synonyms Acrylic acid, methyl ester Methyl 2-propenoate Chemical Formula CH2=CHCOOCH3. 

The application of 3-aminopropyl phosphine (3) [41,46] as a building block for incorporation into -COOH functionalized frameworks provides an excellent example of the utility of preformed primary phosphine frameworks (Scheme 8) [46]. The reactions involved Michael addition of ferf-butyl acrylate to malonic acid dimethyl ester to produce the intermediate adduct, 2-methoxycarbonyl-pentanedioc acid 5-ferf-butyl ester 1-methyl ester, which upon treatment with trifluro-acetic acid (TFA) produced the corresponding diester acid,2-methoxy-carbonyl-pentanedioic acid 1-methyl ester, in near quantitative yield. It is remarkable to note that the reaction of NH2(CH2)3PH2 (3) with the diester acid is highly selective as the -COOH group remained unattacked whereas the reaction occurred smoothly and selectively at the -COOMe groups to pro-... 

Propenoic acid amide, see Acrylamide 2-Propenoic acid, ethyl ester, see Ethyl acrylate Propenoic acid, methyl ester, see Methyl acrylate 2-Propenoic acid, methyl ester, see Methyl acrylate 2-Propenoic acid, 2-methyl methyl ester, see Methyl methacrylate... 

Franker reported the reaction of nitroform with acrylic acid and its esters. Methyl 4,4,4-trinitrobutyrate (127), the product obtained from nitroform and methyl acrylate, has been used... 

Monomers which can add to their own radicals are capable of copolymerizing with SO2 to give products of variable composition. These include styrene and ring-substituted styrenes (but not a-methylstyrene), vinyl acetate, vinyl bromide, vinyl chloride, and vinyl floride, acrylamide (but not N-substituted acrylamides) and allyl esters. Methyl methacrylate, acrylic acid, acrylates, and acrylonitrile do not copolymerize and in fact can be homopolymer-ized in SO2 as solvent. Dienes such as butadiene and 2-chloro-butadiene do copolymerize, and we will be concerned with the latter cortpound in this discussion. 

Other 2-substituted cyclopropylideneacetates of type 3-X also entered this cycloaddition (Scheme 15) [19]. The endolexo selectivity is low but usually still higher than that of simple acrylic acid esters. The relative Diels-Alder reactivities of dienophiles 1-Me and 3-X as determined by competition experiments (Scheme 15) suggest a mechanism involving either diradicals or zwitterions as intermediates [19]. Surprisingly, the 2-fluoro derivative 3-F is less reactive than the parent compound 3-H. The 2-chloro and 2-bromo derivatives 1-Me and 3-Br have similar reactivities and cycloadd to furan (57) about 16 times faster than methyl acrylate. 

Synonyms 2-Propenoic acid methyl ester acrylic acid methyl ester methyl propenoate... 

Synonyms Methacrylic acid, methyl ester methyl 2-methylpropenoic acid methyl a-methyl acrylate methyl methylacrylate 2-(methyoxycarbonyl)-1 -propene... 

Close to 2 billion pounds of polymeric products based on acrylic and methacrylic esters are produced annually in the United States, about evenly divided between acrylates and methacrylates. A substantial fraction of the methacrylate products are copolymers. Most of the acrylate products are copolymers. The copolymers contain various combinations of acrylate and/or methacrylate monomers, including combinations of ester and acid monomers. Methyl methacrylate (MMA) is by far the most important methacrylate ester monomer, accounting for 90% of the volume of methacrylic ester monomers. Ethyl and n-butyl acrylates account for about 80% of the total volume of acrylate ester monomers. 

Many mechanisms had been proposed in the past to rationalize this selectivity (tri-oxanes, perepoxide, exciplex, dipolar or biradical intermediates) however, it is now generally accepted that the reaction proceeds through an intermediate exciplex which has the structural requirements of a perepoxide. This assumption is supported by (a) the lack of stereoselectivity in the reactions with chiral oxazolines and tiglic acid esters (b) the comparison of the diastereoselectivity of dialkyl substituted acrylic esters with structurally similar non-functionalized aUtenes (c) the intermolecular isotope effects in the photooxygenation of methyl tiglate and (d) the solvent effects on regioselectivity. ... 

The formation of spirocyclopropanes from the reaction of diazodiphenylmethane and ( )-8-phenylmenthyl esters of acrylic acid and methyl fumarate occurred with a modest level of diastereofacial selectivity (136). In contrast, diastereoselectivities of 90 10 were achieved in the cycloadditions of diazo(trimethylsilyl)methane with acrylamides 65 derived from camphor sultam as the chiral auxiliary (137) (Scheme 8.16). Interestingly, the initial cycloadducts 66 afforded the nonconjugated A -pyrazolines 67 on protodesilylation the latter were converted into optically active azaproline derivatives 68. In a related manner, acrylamide 69 was converted into A -pyrazolines 70a,b (138). The major diastereoisomer 70a was used to synthesize indolizidine 71. The key step in this synthesis involves the hydrogenolytic cleavage of the pyrazoline ring. 

Water (28 g) and polyoxyethylene phenyl ether sulfuric acid ester emulsifier (0.08 g) were added to a 300-ml flask and heated to 85°C while stirring. This solution was then treated with a mixture of the step 4 product (6.3 g), methyl methacrylate (41.6 g), styrene (14 g), butyl acrylate (23.5 g), 2-ethylhexyl acrylate (14.6 g), water (51.6 g), polyoxyethylene phenyl ether sulfuric acid ester emulsifier (6.6 g), and 0.3 g of sodium persulfate over 4 hours. Thereafter, a mixture of water (5.2 g) and ammonium persulfate (0.1 g) were added over 30 minutes and the mixture stirred for an additional 2 hours. It was then cooled to ambient temperature and a white resin isolated, which consisted of 52% solids with a polymerization conversion of 99%. 

METHYL ACRYLATE Acrylic Acid,methyl ester, Methyl 2-propenoate Flammable Liquid, 11 2 3 2 ... 

ABA ABS ABS-PC ABS-PVC ACM ACS AES AMMA AN APET APP ASA BR BS CA CAB CAP CN CP CPE CPET CPP CPVC CR CTA DAM DAP DMT ECTFE EEA EMA EMAA EMAC EMPP EnBA EP EPM ESI EVA(C) EVOH FEP HDI HDPE HIPS HMDI IPI LDPE LLDPE MBS Acrylonitrile-butadiene-acrylate Acrylonitrile-butadiene-styrene copolymer Acrylonitrile-butadiene-styrene-polycarbonate alloy Acrylonitrile-butadiene-styrene-poly(vinyl chloride) alloy Acrylic acid ester rubber Acrylonitrile-chlorinated pe-styrene Acrylonitrile-ethylene-propylene-styrene Acrylonitrile-methyl methacrylate Acrylonitrile Amorphous polyethylene terephthalate Atactic polypropylene Acrylic-styrene-acrylonitrile Butadiene rubber Butadiene styrene rubber Cellulose acetate Cellulose acetate-butyrate Cellulose acetate-propionate Cellulose nitrate Cellulose propionate Chlorinated polyethylene Crystalline polyethylene terephthalate Cast polypropylene Chlorinated polyvinyl chloride Chloroprene rubber Cellulose triacetate Diallyl maleate Diallyl phthalate Terephthalic acid, dimethyl ester Ethylene-chlorotrifluoroethylene copolymer Ethylene-ethyl acrylate Ethylene-methyl acrylate Ethylene methacrylic acid Ethylene-methyl acrylate copolymer Elastomer modified polypropylene Ethylene normal butyl acrylate Epoxy resin, also ethylene-propylene Ethylene-propylene rubber Ethylene-styrene copolymers Polyethylene-vinyl acetate Polyethylene-vinyl alcohol copolymers Fluorinated ethylene-propylene copolymers Hexamethylene diisocyanate High-density polyethylene High-impact polystyrene Diisocyanato dicyclohexylmethane Isophorone diisocyanate Low-density polyethylene Linear low-density polyethylene Methacrylate-butadiene-styrene... 

Figure 12.20 demonstrates that Michael acceptors can also act as electrophiles towards enam-ines. Aqueous workup leads to the regeneration of the carbonyl group, and the Michael addition product C is obtained. An acrylic acid ester would react with the enamine A in complete analogy to the reaction of the acrylonitrile shown here the same holds true for the methyl vinyl ketone. 

Diels-Alder reactions of the type shown in Table 15.1, that is, Diels-Alder reactions between electron-poor dienophiles and electron-rich dienes, are referred to as Diels-Alder reactions with normal electron demand. The overwhelming majority of known Diels-Alder reactions exhibit such a normal electron demand. Typical dienophiles include acrolein, methyl vinyl ketone, acrylic acid esters, acrylonitrile, fumaric acid esters (irans-butenedioic... 

Steps 1-3 of the catalytic cycle correspond to various steps of other catalytic cycles already discussed in Chapter 13. Step 1 tt-complex formation by combination of the aryl triflate and a sufficiently valence-unsaturated and thus sufficiently reactive Pd(0) species. Step 2 oxi-dative addition of the aryl triflate to Pd with formation of a Cspi—Pd(II) bond. Steps 3a and 3b exchange of a PPh3 ligand by an acrylic acid methyl ester via a dissociation/addition mechanism. The newly entered acrylic acid ester is bound as a 77 complex. 

The most common monomers used are methacrylic acid (2-methyl propenoic acid) and its esters or, less commonly, acrylic acid (propenoic acid) and its esters. 

Vinyl lacquers are used mainly where a high degree of chemical resistance is required these lacquers are based on vinyl chlorides and vinyl acetates. Acrylic lacquers are based on methyl methacrylate and methyl acrylate polymers and copolymers. Other esters of acrylic and methacrylic acid also may be used to make nonconvertible film formers. Judicious selection of these acrylic acid or methacrylic acid esters allows one to produce film formers with specifically designed properties such as hardness, flexibility, gloss, durability, heat, and chemical resistance. Acrylic lacquers, however, are not noted for their water resistance. The principal uses of acrylic-type lacquers are fluorescent and metallic paints, car refinish applications, clear lacquers and sealers for metals, and protective coatings for aircraft components and for vacuum-deposited metals, as well as uses in pigmented coatings for cabinets and appliances. 

Poly(vinyl alcohol) is utilized as a component of starch-based adhesives.11121114 Other patents report the use of partially oxidized starch,1115 dextrins,1116 dextrins and urea,1117 borax,1118 boric acid,1119 and vinyl methyl ether-maleic acid copolymers.1120 Other patents indicate the use of poly (vinyl alcohol) with partially hydrolyzed poly(vinyl acetate),1121 nonhy-drolyzed poly(vinyl acetate),1122 and poly(vinyl chloride).1123 A few patents have reported such poly acrylic additives as poly (acrylic acid)1124 and its salts,1125 poly(acrylamide),1126 1127 A-methylacrylamide or poly(A-acryl-amide),1128 and polyethyleneimine.1129 Polystyrene has also been used,1130 as well as more complex copolymers such as a maleic acid monobutyl ester-methyl vinyl ether copolymer, together with dextrin and polyacrylamide),1131 carboxylated ethyl acrylate-styrene zinc salt copolymer,1132 ethylene-methyl acrylate-vinyl acetate copolymer,1133 vinyl acetate-vinyl pyr-rolidone copolymer,1134 and ethylene-vinyl acetate copolymer.1135 Some adhesives are compounded with SBR latex1136 1138 and phenol-formaldehyde resins.1139... 

By reacting the product of Step 2 with methyl acrylate, the corresponding ester, methyl 2-bromo-3-[4-methoxy-3-[N-(4-trifluoromethylbenzyl)]-carbamoylphenyl]propanic acid, was prepared by the author. 

ACRYLIC ACID, 2-METHYL- see MDN250 ACR XIC ACID METHYL ESTER (1VLA.K) see MGA500 ACRYLIC ACID, 2-METHYL-, METHYL ESTER see -MLH750 ACRYLIC ACID,... 

---