Esterification of Acrylic Acid with 1,4‐Butanediol in a Batch Distillation Column Reactor over Amberlyst 15 Catalyst

Abstract

The esterification reaction of acrylic acid (AA) with 1,4‐butanediol (BD) to produce 4‐hydroxybutyl acrylate (HBA) was carried out in a batch reactive distillation mode over the Amberlyst 15 catalyst. The reactive distillation was highly desirable to increase the reaction rate of BD and eventually to obtain the high purity of HBA because the unreacted BD was not easily separable to the produced HBA after the reaction. The reaction pressure below 760 mm Hg was used to remove the by‐product water from the reaction zone. The air‐bubbling operation was successfully applied to prevent the polymerization of reactants and products under the vacuum condition (400 ∼ 760 mm Hg). The reaction rates were strongly dependent on the reaction pressure, especially, the reaction rate of BD disappearance. The increased reaction rate of BD by the reactive distillation enabled to produce a high purity of HBA.

Pervaporation membrane reactors (PVMRs) for esterification

“…Some relevant and recent examples are esterification of acetic acid with methanol (Agreda & Partin, 1984;Chandrakar, Agarwal, Chand, & Wasewar, 2007), esterification of succinic acid and ethanol (Kolah, Asthana, Vu, Lira, & Miller, 2008a;Orjuela, Kolah, Lira, & Miller, 2011;Orjuela, Kolah, Hong, Lira, & Miller, 2012), reaction of citric acid (CA) with ethanol to give triethyl citrate (Kolah, Asthana, Vu, Lira, & Miller, 2008b) and CA (Kolah, Asthana, Vu, Lira, & Miller, 2007), esterification of 1-propanol and propionic acid (Kotora, Buchaly, Kreis, G orak, & Marko s, 2008;Altman et al, 2010;Cruz-Diaz et al, 2012;, esterification of acetic acid and ethanol (Yagyu et al, 2013) (which is the most studied reaction concerning reactive distillation for esterification (Drioli & Giorno, 2010)), esterification of acetic acid with n-butanol (Arpornwichanop, Koomsup, & Assabumrungrat, 2008), esterification of acryl acid with 1,4-butanediol to obtain 4-hydroxybutyl acrylate (Yang, Cho, Park, & Lee, 2007), reaction of lactic acid with n-butanol (Kumar & Mahajani, 2007), esterification of acrylic acid and n-butanol (Niesbach, Fuhrmeister, Keller, Lutze, & Gorak, 2012), synthesis of an n-butyl acetate system using a reactive distillation from an agroindustrial waste (i.e., starting from oil of Fusel) (Altomare, Labrador, Rodriguez, Morales, & Fernandez, 2012), and esterification of butyric acid and n-butanol (Ju et al, 2011). Some relevant and recent examples are esterification of acetic acid with methanol (Agreda & Partin, 1984;Chandrakar, Agarwal, Chand, & Wasewar, 2007), esterification of succinic acid and ethanol (Kolah, Asthana, Vu, Lira, & Miller, 2008a;Orjuela, Kolah, Lira, & Miller, 2011;Orjuela, Kolah, Hong, Lira, & Miller, 2012), reaction of citric acid (CA) with ethanol to give triethyl citrate (Kolah, Asthana, Vu, Lira, & Miller, 2008b) and CA (Kolah, Asthana, Vu, Lira, & Miller, 2007), esterification of 1-propanol and propionic acid …”

Continuous Plug Flow Process for the Transesterification of Methyl Acrylate and 1,4-Butanediol by a Zn-Immobilized Catalyst for Producing 4-Hydroxybutyl Acrylate

“…Therefore, alternative methods for direct monoesterification of acrylates with diols under mild conditions while controlling the byproduction of diol bis-acrylates are needed. Lee et al reported catalytic esterification of acrylic acid with 1,4-butanediol to produce 4-hydroxybutyl acrylate over several ion exchange resins . They precisely conducted kinetic studies of the condensation reaction over Amberlyst 15 in heterogeneous conditions via the quasi-homogeneous model to determine all kinetic parameters.…”

Stimuli Responsive Self‐Assembly of 3‐(Octyloxy)‐3‐Oxopropyl Acrylate‐Co‐Acrylic Acid Polymer in Aqueous Media

“…Numerous esterification catalysts are reported in the literature for carrying out direct esterification of fatty alcohol with acrylic acid [1][2][3][4]. In general, all such reactions result in 90 % formation of fatty acrylate along with a range of by-products.…”

“…The major by-product is the Michael adduct, 3-(alkyloxy)-3-oxopropyl acrylate, formed by the addition of unreacted acrylic acid with the terminal double bond of alkyl acrylate. In an attempt to prepare fatty acrylate, we have carried out direct esterification of fatty alcohol with acrylic acid in the presence of a catalytic amount of NaHSO 4 . The reaction resulted in near equal formation of fatty acrylate and 3-(alkyloxy)-3-oxopropyl acrylate [5].…”