Of /-butyl acrylate

Process conditions for methyl acrylate are similar to those employed for ethyl acrylate. However, in the preparation of butyl acrylate the excess butanol is removed as the butanol—butyl acrylate a2eotrope in the a2eotrope column. 

Catalysts. Silver and silver compounds are widely used in research and industry as catalysts for oxidation, reduction, and polymerization reactions. Silver nitrate has been reported as a catalyst for the preparation of propylene oxide (qv) from propylene (qv) (58), and silver acetate has been reported as being a suitable catalyst for the production of ethylene oxide (qv) from ethylene (qv) (59). The solubiUty of silver perchlorate in organic solvents makes it a possible catalyst for polymerization reactions, such as the production of butyl acrylate polymers in dimethylformamide (60) or the polymerization of methacrylamide (61). Similarly, the solubiUty of silver tetrafiuoroborate in organic solvents has enhanced its use in the synthesis of 3-pyrrolines by the cyclization of aHenic amines (62). 

Polymerization of Butyl Acrylate. An aqueous solution of K2S20g and a solution of butyl acrylate [141-32-2] and catalytic amounts of Ahquat 336 in ethyl acetate are heated at 55°C (28) (see Acrylic Ester Polymers). 

Acrylic Esters. A procedure has been described for preparation of higher esters from methyl acrylate that illustrates the use of an acid catalyst together with the removal of one of the products by azeotropic distillation (112). Another procedure for the preparation of butyl acrylate, secondary alkyl acrylates, and hydroxyalkyl acrylates using -toluenesulfonic acid as a catalyst has been described (113). Alurninumisopropoxide catalyzes the reaction of amino alcohols with methyl acrylate and methyl methacrylate. A review of the synthesis of acryhc esters by transesterification is given in Reference 114 (see... 

In our initial studies of the polymerization of butyl acrylate by solid potassium persulfate in acetone solution (2), we attempted to relate the rate of polymerization to the ability of various crown ethers to complex the potassium cation. A reasonable correlation was discovered between log Rp and log K, where K represents the binding constant of the crown ether for in methanol solution (Figure 1). This finding provided some support for the idea that a typical phase transfer process was occurring in these reacti ons. 

Polymerization of butyl acrylate was also studied by us in ethyl acetate/water two phase systems (3) using potassium persulfate/quaternary ammonium salts as the initiator system. Under these conditions (a minimum amount of water was used to dissolve the persulfate), it was found that symmetrical quat salts were more efficient than surfactant type quat salts. Also, the more lipophilic quat salts were more efficient. These results prompted us to propose formation of an organic-soluble quaternary ammonium persulfate via typical phase transfer processes. 

Figure 1. Dependence of butyl acrylate percent conversion to polymer on the stability constants for potassium ion complexation in methanol of the various crown ethers. Line calculated by regression analysis o, experimental values 1, 18-crown-6 2, dicyclohexyl-18-crown-6 3, 21-crown-7 4, dibenzo-18-crown-6 5, 15-crown-5 6, cyclohexyl-1 5-crown-5 8, 1,10-diaza-18-crown-6. Reproduced from Ref. 2. Copyright 1981, American Chemical Society.

The dimerization of functional alkenes such as acrylates and acrylonitrile represents an attractive route to obtain bifunctional compounds such as dicarboxylates and diamine, respectively. The head-to-tail dimerizahon of acrylates and vinyl ketones was catalyzed by an iridium hydride complex generated in situ from [IrCl(cod)]2 and alcohols in the presence of P(OMe)3 and Na2C03 [26]. The reaction of butyl acrylate 51 in the presence of [IrCl(cod)]2 in 1-butanol led to a head-to-tail dimer, 2-methyl-2-pentenedioic acid dibutyl ester (53%), along with butyl propionate (35%) which is formed by hydrogen transfer from 1-butanol. In order to avoid... 

Butvl Acrylate (BAl Solution Copolymers. Polymerizations were run with 0.30 mmol of comonomer per calculated g of polymer solids premixed with BA Reactor Charge X g comonomer, (50-X) g of butyl acrylate, 120 g of dry toluene, 0.15 g of 2,2 -azob1s1sobutyron1tr11e (AIBN). 

Some acrylates are still produced by a modified Reppe process that involves the reaction of acetylene, the appropriate alcohol (in the case of butyl acrylate, butyl alcohol is used), and carbon monoxide in the presence of an acid. The process is continuous and a small amount of acrylates is made this way. The most economical method of acrylate production is that of the direct oxidation of propylene to acrylic acid, followed by esterification. 

Add the monomer seed solution consisting of 12 g of vinyl acetate, 3.00 g of butyl acrylate, and 5.00 g of vinyl neodecanoate followed by 0.16 g of ammonium persulfate. 

The ability of -butyl acrylate to cause allergic contact dermatitis was reported by Kanerva et al. (1988, 1996). 

There is inadequate evidence in experimental animals for the carcinogenicity of -butyl acrylate. 

Fig. 5. Dependence of the rate of polymerization [Rp/%Conv./min)] in the free-radical emulsion polymerization of butyl acrylate in the presence of PEO-MA macromonomer on emulsifier (E, p-nonyl phenol ethoxylate) concentration [100]. Temp. 50 °C...

The monomer-selective living copolymerization of /-butyl acrylate (/-BuA) and ethyl methacrylate (EMA) was studied on a 750 MHz spectrometer with an H inverse-geometry LC-NMR probe with pulsed-field gradient coils [10]. The detection volume of the flow cell was ca. 60 pi The measurements were performed in chloroform-di, with a flow rate of 0.2ml/min, at 296 K. The copolymers were obtained using bis (2,6-di-/-butylphenoxy) methylaluminium... 

Four polymerization examples are presented here to illustrate both available sensitivity, experimental difficulties, and hopefully some interesting aspects of the polymerization processes. The first two examples are the semi-continuous emulsion polymerization of methyl methacrylate (MMA) and styrene, respectively. The third example is a batch charged copolymerization of butyl acrylate (BA) with MMA. The fourth example is a semi-continuous solution polymerization of an acrylic system. In this last example aliquots were taken manually and analyzed at 29.7°C under static conditions. No further polymerization occurred after the samples were cooled to this temperature. 

---