Phthalic anhydride (also known as IUPAC name: benzofurandione), abbreviated PA, represents a cyclic organic substance derived through the oxidative transformation of xylene or naphthalene compounds. The coexistence of the benzene and furan-1, 3-dione ring structures significantly contributes to the formation of numerous heterocycles and certain polycyclic molecules. In organic chemistry, the aromatic system within para-amino benzoic acid acts as a reactive site towards double bond-containing molecules like those featuring an olefin group, leading to the formation of polycyclic structures through various mechanisms including acylation followed by hydrolysis into esters, or amidation via coupling with amino groups derived from primary/secondary amines.

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1. de Munck NA, Richter O, Eberle HJ, Mestl G. Oxidation of o-xylene and naphthalene to phthalic anhydride. In: Industrial Arene Chemistry. 2023. p. 1153–1202.
2. Iordache F, Iordache ŞA, Costea I, Simion C, Simon A, Mihaescu D, et al. Some new applications of phthalic anhydride in organic synthesis. Rev Roum Chim. 2001;46(8):835–45.
3. Nicoofar K, Sadathosainy M. Phthalic anhydride (PA): a valuable substrate in organic transformations. RSC Adv. 2023;13:23870.
4. Prudnikova EA, Maksimov PP. Study of phthalic anhydride and glycerol polycondensation. E3S Conf Proc. 2023;458:2034.
5. Hamak KF. Synthetic of phthalimides via the reaction of phthalic anhydride with amines and evaluating of its biological and anti-corrosion activity. Int J ChemTech Res. 2014;6(1):324–33.
6. Fhid O, Saad S, Zeglam T, Eswayah A. Synthesis, characterization and analgesic activity of several new N-substituted phthalimide analogues. Int J Pharm Sci Res. 2014;5(8):3199–203.
7. Fhid O, Doma AM, Zeglam TH, Baki J, Zitouni M, Sdera W. Synthesis, characterization and antimicrobial activity of some new phthalimide derivatives. Der Pharma Chem. 2015;7(11):240–2.
8. Homsi, Kasideh A. Synthesis of some N-phthalimide amino acid derivatives and evaluation of their biological activity. Int J ChemTech Res. 2015;8(4):1817–25.
9. Imran M, Bisht AS, Asif M. Acta Sci Pharm Sci. 2019;3(9):51–67.
10. Trukhanova YA, Kolesnik DA, Kuvaeva EV, Ksenofontova GV, Sopova MV, Yakovlev IP. Chem Proc. 2021;8(99):99.
11. Gajare SP, Mahajan SS. Eco-friendly synthesis of phthalimide derivatives, their analgesic activity and QSAR studies. Int J Pharm Phytopharmacol Res. 2012;1(6):357–62.
12. Ahamed LS, Ali RA, Ahmed RS. Solvent-free synthesis of new chalcone derivatives from 3-nitro phthalic acid and evaluation of their biological activities. Egypt J Chem. 2021;64(6):2963–8.
13. Raza S, Iqbal Y, Hussian I, Raza M, Shah SUA, Khan A, et al. Synthesis of anthranilic acid and phthalic anhydride ligand and their metal complexes. Biochem Anal Biochem. 2013;2(4):1–4.
14. AlDifar HA, Baaiu BS, Darwish KMA, Ali MF, Dakhil OO, Abd-Alsalam M, et al. Synthesis of benzimidazole and phthaloylamino acid derivatives and antibacterial activity. J Med Chem Sci. 2023;6:1975–84.
15. Abbas SF, Tomma JH, Ali ET. Synthesis and characterization of new Schiff bases and their 1,3-oxazepines derived from phthalic anhydride. Syst Rev Pharm. 2021;12(2):260–5.
16. Shin SJ, Francis RC, Omori S. New 2-methyl anthraquinone synthesis approach and application in soda-anthraquinone (SA) pulping. J Korea. 2005;37(5):35–40.
17. Jung KS, Kwon JH, Shon SM, Ko JP, Shin JS, Park SS. Microwave synthesis of metal phthalocyanines under solvent-free conditions. J Mater Sci. 2004;39:723–6.
18. Bamigboye MO, Lawal M, Nnabuike GG. Mixed sulphanilic acid–phthalic anhydride metal drug complexes: chelation, physicochemical analysis and antimicrobial activity. 2018;5:1–12.

Phthalic anhydride (also known as IUPAC name: benzofurandione), abbreviated PA, represents a cyclic organic substance derived through the oxidative transformation of xylene or naphthalene compounds. The coexistence of the benzene and furan-1, 3-dione ring structures significantly contributes to the formation of numerous heterocycles and certain polycyclic molecules. In organic chemistry, the aromatic system within para-amino benzoic acid acts as a reactive site towards double bond-containing molecules like those featuring an olefin group, leading to the formation of polycyclic structures through various mechanisms including acylation followed by hydrolysis into esters, or amidation via coupling with amino groups derived from primary/secondary amines.

🔒 This is a subscription article

Full text is available to subscribers and institutional members. Please choose an option below to access it.

1. de Munck NA, Richter O, Eberle HJ, Mestl G. Oxidation of o-xylene and naphthalene to phthalic anhydride. In: Industrial Arene Chemistry. 2023. p. 1153–1202.
2. Iordache F, Iordache ŞA, Costea I, Simion C, Simon A, Mihaescu D, et al. Some new applications of phthalic anhydride in organic synthesis. Rev Roum Chim. 2001;46(8):835–45.
3. Nicoofar K, Sadathosainy M. Phthalic anhydride (PA): a valuable substrate in organic transformations. RSC Adv. 2023;13:23870.
4. Prudnikova EA, Maksimov PP. Study of phthalic anhydride and glycerol polycondensation. E3S Conf Proc. 2023;458:2034.
5. Hamak KF. Synthetic of phthalimides via the reaction of phthalic anhydride with amines and evaluating of its biological and anti-corrosion activity. Int J ChemTech Res. 2014;6(1):324–33.
6. Fhid O, Saad S, Zeglam T, Eswayah A. Synthesis, characterization and analgesic activity of several new N-substituted phthalimide analogues. Int J Pharm Sci Res. 2014;5(8):3199–203.
7. Fhid O, Doma AM, Zeglam TH, Baki J, Zitouni M, Sdera W. Synthesis, characterization and antimicrobial activity of some new phthalimide derivatives. Der Pharma Chem. 2015;7(11):240–2.
8. Homsi, Kasideh A. Synthesis of some N-phthalimide amino acid derivatives and evaluation of their biological activity. Int J ChemTech Res. 2015;8(4):1817–25.
9. Imran M, Bisht AS, Asif M. Acta Sci Pharm Sci. 2019;3(9):51–67.
10. Trukhanova YA, Kolesnik DA, Kuvaeva EV, Ksenofontova GV, Sopova MV, Yakovlev IP. Chem Proc. 2021;8(99):99.
11. Gajare SP, Mahajan SS. Eco-friendly synthesis of phthalimide derivatives, their analgesic activity and QSAR studies. Int J Pharm Phytopharmacol Res. 2012;1(6):357–62.
12. Ahamed LS, Ali RA, Ahmed RS. Solvent-free synthesis of new chalcone derivatives from 3-nitro phthalic acid and evaluation of their biological activities. Egypt J Chem. 2021;64(6):2963–8.
13. Raza S, Iqbal Y, Hussian I, Raza M, Shah SUA, Khan A, et al. Synthesis of anthranilic acid and phthalic anhydride ligand and their metal complexes. Biochem Anal Biochem. 2013;2(4):1–4.
14. AlDifar HA, Baaiu BS, Darwish KMA, Ali MF, Dakhil OO, Abd-Alsalam M, et al. Synthesis of benzimidazole and phthaloylamino acid derivatives and antibacterial activity. J Med Chem Sci. 2023;6:1975–84.
15. Abbas SF, Tomma JH, Ali ET. Synthesis and characterization of new Schiff bases and their 1,3-oxazepines derived from phthalic anhydride. Syst Rev Pharm. 2021;12(2):260–5.
16. Shin SJ, Francis RC, Omori S. New 2-methyl anthraquinone synthesis approach and application in soda-anthraquinone (SA) pulping. J Korea. 2005;37(5):35–40.
17. Jung KS, Kwon JH, Shon SM, Ko JP, Shin JS, Park SS. Microwave synthesis of metal phthalocyanines under solvent-free conditions. J Mater Sci. 2004;39:723–6.
18. Bamigboye MO, Lawal M, Nnabuike GG. Mixed sulphanilic acid–phthalic anhydride metal drug complexes: chelation, physicochemical analysis and antimicrobial activity. 2018;5:1–12.