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Benzyl butyl phthalate
Benzyl butyl phthalate (BBP) is an organic compound historically used as a plasticizer, which has now been largely phased out due to health concerns. It is a phthalate ester of containing benzyl alcohol, and n-butanol tail groups. Like most phthalates, BBP is non-volatile and remains liquid over a wide range of temperatures. It was mostly used as a plasticizer for PVC, but was also a common plasticizer for PVCA and PVB.
BBP was commonly used as a plasticizer for vinyl foams, which are often used as sheet vinyl flooring and tiles. Compared to other phthalates it was less volatile than dibutyl phthalate and imparted better low temperature flexibility than di(2-ethylhexyl) phthalate.
BBP is classified as toxic by the European Chemical Bureau (ECB) and hence its use in Europe has declined rapidly.
BBP is a diester. Since BBP contains two ester bonds it can react in a variety of chemical pathways. Both the carbonyl C-atoms are weakly electrophilic and therefore targets for attacks by strong nucleophilic compounds. Besides the carbonyl C-atom target, it contains a C-H bond whereas the H-atom is weakly acidic, which makes it susceptible for deprotonation by a strong base. BBP is hydrolyzed under either acidic or basic conditions. The hydrolysis under acidic conditions is a reversion of the Fischer-Speier esterification, whereas the hydrolysis under basic conditions is performed by saponification. Since BBP contains two ester bonds it is difficult to perform a chemoselective reaction.
Under basic conditions BBP can undergo saponification. The saponification number of BBP is 360 mg KOH/g. The amount of carboxylic functional groups per molecule are relatively high (2 carboxylic functional groups with a molecular weight of 312.36). This makes the compound relatively unsaponifiable.
Concentrated sulfuric acid dehydrates n-butyl alcohol to yield 1-butene, which reacts with phthalic anhydride to produce n-butyl phthalate. Phthalic anhydride does react directly with 1-butanol to form this same intermediate, but further reaction to form dibutyl phthalate does occur to a significant extent. Carrying out the procedure using 1-butene avoids this side reaction. Monobutyl phthalate is isolated and then added to a mixture of benzyl bromide in acetone in the presence of potassium carbonate (to keep the pH high to facilitate the substitution reaction required to form the second ester linkage), from which BBP can then be isolated.
BBP can be absorbed by the human body in a variety of ways. First of all, it can be taken up dermally, meaning that the compound is absorbed by the skin. Studies in rats show that 27% of the uptake of BBP occurs via this route. During this process, the structure of the phthalate diester determines the degree of dermal absorption.
BBP can also be taken up orally. The amount of the compound that is being absorbed by the body depends on the dose that has been administered. Absorption seems to be limited at high doses, meaning that small amounts are taken up more easily than great amounts. Finally, BBP can be inhaled. In this case, BBP is absorbed via the lungs.
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Benzyl butyl phthalate
Benzyl butyl phthalate (BBP) is an organic compound historically used as a plasticizer, which has now been largely phased out due to health concerns. It is a phthalate ester of containing benzyl alcohol, and n-butanol tail groups. Like most phthalates, BBP is non-volatile and remains liquid over a wide range of temperatures. It was mostly used as a plasticizer for PVC, but was also a common plasticizer for PVCA and PVB.
BBP was commonly used as a plasticizer for vinyl foams, which are often used as sheet vinyl flooring and tiles. Compared to other phthalates it was less volatile than dibutyl phthalate and imparted better low temperature flexibility than di(2-ethylhexyl) phthalate.
BBP is classified as toxic by the European Chemical Bureau (ECB) and hence its use in Europe has declined rapidly.
BBP is a diester. Since BBP contains two ester bonds it can react in a variety of chemical pathways. Both the carbonyl C-atoms are weakly electrophilic and therefore targets for attacks by strong nucleophilic compounds. Besides the carbonyl C-atom target, it contains a C-H bond whereas the H-atom is weakly acidic, which makes it susceptible for deprotonation by a strong base. BBP is hydrolyzed under either acidic or basic conditions. The hydrolysis under acidic conditions is a reversion of the Fischer-Speier esterification, whereas the hydrolysis under basic conditions is performed by saponification. Since BBP contains two ester bonds it is difficult to perform a chemoselective reaction.
Under basic conditions BBP can undergo saponification. The saponification number of BBP is 360 mg KOH/g. The amount of carboxylic functional groups per molecule are relatively high (2 carboxylic functional groups with a molecular weight of 312.36). This makes the compound relatively unsaponifiable.
Concentrated sulfuric acid dehydrates n-butyl alcohol to yield 1-butene, which reacts with phthalic anhydride to produce n-butyl phthalate. Phthalic anhydride does react directly with 1-butanol to form this same intermediate, but further reaction to form dibutyl phthalate does occur to a significant extent. Carrying out the procedure using 1-butene avoids this side reaction. Monobutyl phthalate is isolated and then added to a mixture of benzyl bromide in acetone in the presence of potassium carbonate (to keep the pH high to facilitate the substitution reaction required to form the second ester linkage), from which BBP can then be isolated.
BBP can be absorbed by the human body in a variety of ways. First of all, it can be taken up dermally, meaning that the compound is absorbed by the skin. Studies in rats show that 27% of the uptake of BBP occurs via this route. During this process, the structure of the phthalate diester determines the degree of dermal absorption.
BBP can also be taken up orally. The amount of the compound that is being absorbed by the body depends on the dose that has been administered. Absorption seems to be limited at high doses, meaning that small amounts are taken up more easily than great amounts. Finally, BBP can be inhaled. In this case, BBP is absorbed via the lungs.