Table 4.
Carboxylic acids used in the formation of OCPC.
| Carboxylic acid (CAS No.) | Formula | Molecular weight | OCPC formation | Year [Reference No.] |
|---|---|---|---|---|
| Monocarboxylic acids | ||||
| Formic acid (64-18-6) | HCOOH | 46.03 | No | 1992 [48] 1993 [17] 2001 [45] |
| Acetic acid (64-19-7) | CH3COOH | 60.05 | No | 1984 [18] 1992 [48] 1993 [17] 2001 [45] |
| Propionic acid (79-09-4) | CH3CH2COOH | 74.08 | No | 2011 [41] |
| Glycine (56-40-6) | NH2CH2COOH | 75.07 | No | 1992 [48] 1993 [17] 2000 [47] 2001 [45] |
| Pyruvic acid (127-17-3) | CH3COCOOH | 88.06 | Yes | 1993 [17]* 2001 [45]* |
| Lactic acid** | CH3CH(OH)COOH | 90.08 | No | 1992 [48] |
| DL-2-Aminobutyric acid (2835-81-6) | CH3CH2CH(NH2)COOH | 103.12 | No | 2000 [47] |
| DL-Norvaline (760-78-1) | CH3(CH2)2CH(NH2)COOH | 117.15 | No | 2000 [47] |
| D-Norleucine (327-56-0) | CH3(CH2)3CH(NH2)COOH | 131.18 | No | 2000 [47] |
| L-Norleucine (327-57-1) | CH3(CH2)3CH(NH2)COOH | 131.18 | No | 2000 [47] |
| DL-Norleucine (616-06-8) | CH3(CH2)3CH(NH2)COOH | 131.18 | No | 2000 [47] |
| L-Ornithine (70-26-8) | NH2(CH2)3CH(NH2)COOH | 132.16 | No | 2000 [47] |
| L-Glutamine (56-85-9) | NH2CO(CH2)2CH(NH2)COOH | 146.15 | No | 2000 [47] |
| L-Lysine (56-87-1) | NH2(CH2)4CH(NH2)COOH | 146.19 | No | 2000 [47] |
| Saturated dicarboxylic acid | ||||
| Malonic acid (141-82-2) | HOOCCH2COOH | 104.06 | Yes | 1984 [18] 1984 [22] 1992 [48] 1993 [17] 2001 [45] |
| Succinic acid (110-15-6) | HOOC(CH2)2COOH | 118.09 | Yes | 1983 [16] 1984 [18] 1984 [22] 1992 [48] 1993 [17] 2000 [46] 2001 [44] 2001 [45] 2008 [21] 2008 [43] 2010 [42] 2012 [39] 2012 [40] 2018 [20] 2021 [31] |
| Glutaric acid (110-94-1) | HOOC(CH2)3COOH | 132.12 | Yes | 1984 [18] 1984 [22] 1992 [48] 2001 [45] |
| Adipic acid (124-04-9) | HOOC(CH2)4COOH | 146.14 | Yes | 1984 [18] 1984 [22] 1992 [48] 1993 [17] 2001 [45] 2008 [21] |
| Pimelic acid (111-16-0) | HOOC(CH2)5COOH | 160.17 | Yes | 1984 [18] 1984 [22] 1992 [48] 2001 [45] |
| Suberic acid (505-48-6) | HOOC(CH2)6COOH | 174.20 | Yes | 1984 [18] 1984 [22] 1992 [48] 1993 [17] 2001 [45] 2008 [21] 2012 [39] 2012 [40] |
| No | 2018 [20] | |||
| Azelaic acid (123-99-9) | HOOC(CH2)7COOH | 188.22 | Yes | 1992 [48] |
| No | 1993 [17] 2001 [45] |
|||
| Sebacic acid (111-20-6) | HOOC(CH2)8COOH | 202.25 | Yes | 1992 [48] 1993 [17] 2001 [45] |
| Unsaturated dicarboxylic acid | ||||
| Maleic acid (110-16-7) | HOOCCH=CHCOOH | 116.07 | Yes | 1992 [48] |
| No | 1993 [17] 2001 [45] |
|||
| Fumaric acid (110-17-8) | HOOCCH=CHCOOH | 116.07 | Yes | 1984 [18] 1992 [48] 1993 [17] 2001 [45] |
| Citraconic acid (498-23-7) | HOOCC(CH3)=CHCOOH | 130.10 | Yes | 1984 [18] 1992 [48] |
| Mesaconic acid (498-24-8) | HOOCC(CH3)=CHCOOH | 130.10 | No | 1992 [48] |
| Itaconic acid (97-65-4) | HOOCCH2C(=CH2)COOH | 130.10 | No | 1992 [48] |
| cis, cis-Muconic acid (1119-72-8) | HOOCCH=CHCH=CHCOOH | 142.11 | Yes | 1992 [48] |
| trans, trans-Muconic acid (3588-17-8) | HOOCCH=CHCH=CHCOOH | 142.11 | No | 1992 [48] |
| β-Dihydromuconic acid (4436-74-2) | HOOCCH2CH=CHCH2COOH | 144.13 | Yes | 1984 [18] 1992 [48] |
| Aromatic dicarboxylic acid | ||||
| Phthalic acid (88-99-3) | HOOC(C6H4)COOH | 166.13 | Yes | 1984 [18] 1992 [48] 2013 [38] |
| Isophthalic acid (121-91-5) | HOOC(C6H4)COOH | 166.13 | Yes | 1992 [48] 2013 [38] 2018 [20] 2022 [30] |
| Terephthalic acid (100-21-0) | HOOC(C6H4)COOH | 166.13 | No | 1992 [48] 2013 [38] |
| 2,2’-Bipyridine-5,5’-dicarboxylic acid (1802-30-8) | HOOC(C5H3N)2COOH | 244.21 | Yes | 2019 [34] |
| Dicarboxylic acid with side chain | ||||
| L-Malic acid (97-67-6) | HOOCCH2CH(OH)COOH | 134.09 | Yes | 1993 [17] 2001 [45] |
| DL-Malic acid (6915-15-7) | 134.09 | Yes | 2000 [46] | |
| Malic acid** | 134.09 | No | 1992 [48] | |
| Mercaptosuccinic acid** | HOOCCH2CH(SH)COOH | 150.15 | Yes | 2000 [46] 2015 [36] 2019 [33] |
| (S)-(–)-Methylsuccinic acid (2174-58-5) | HOOCCH2CH(CH)3COOH | 132.12 | Yes | 2017 [35] |
| (R)-(+)-Methylsuccinic acid (3641-51-8) | HOOCCH2CH(CH)3COOH | 132.12 | No | 2017 [35] |
| Methylsuccinic acid** | HOOCCH2CH(CH)3COOH | 132.12 | Yes | 1984 [18] 1992 [48] 2000 [46] 2001 [44] |
| D-Aspartic acid (1783-96-6) | HOOCCH2CH(NH2)COOH | 133.10 | Yes | 2000 [47] |
| L-Aspartic acid (56-84-8) | HOOCCH2CH(NH2)COOH | 133.10 | Yes | 2000 [46] 2000 [47] 2001 [44] |
| DL-Aspartic acid (617-45-8) | HOOCCH2CH(NH2)COOH | 133.10 | Yes | 2000 [47] |
| Aspartic acid** | HOOCCH2CH(NH2)COOH | 133.10 | Yes | 2008 [43] |
| No | 1992 [48] 1993 [17] 2001 [45] |
|||
| D-Glutamic acid (6893-26-1) | HOOCCH2CH2CH(NH2)COOH | 147.13 | Yes | 2000 [47] |
| L-Glutamic acid (56-86-0) | HOOCCH2CH2CH(NH2)COOH | 147.13 | Yes | 2000 [47] |
| DL-Glutamic acid (617-65-2) | HOOCCH2CH2CH(NH2)COOH | 147.13 | Yes | 2000 [47] |
| Glutamic acid** | HOOCCH2CH2CH(NH2)COOH | 147.13 | No | 1992 [48] 1993 [17] 2001 [45] 2008 [43] |
| Other dicarboxylic acid | ||||
| Oxalic acid (144-62-7) | HOOCCOOH | 90.03 | No | 1984 [18] 1992 [48] 2001 [45] |
| Oxaloacetic acid (328-42-7) | HOOCCH2COCOOH | 132.07 | No | 1993 [17] 2001 [45] |
| α-Ketoglutaric acid (328-50-7) | HOOC(CH2)2COCOOH | 146.10 | Yes | 1993 [17]* 2001 [45]* |
| β-Ketoglutaric acid (542-05-2) | HOOCCH2COCH2COOH | 146.10 | No | 1993 [17] 2001 [45] |
| Tricarboxylic acid | ||||
| Citric acid (77-92-9) | HOOCCH2C(OH)(COOH)CH2COOH | 192.12 | Yes | 1993 [17] 2001 [45] 2008 [43] 2014 [37] 2021 [27] |
| No | 1992 [48] | |||
| Tetracarboxylic acid | ||||
| Pyromellitic acid (89-05-4) | (C6H2)(COOH)4 | 254.15 | Yes | 2021 [32] |
| Others | ||||
| Urea (57-13-6) | NH2CONH2 | 60.06 | No | 1992 [48] |
| Hydroquinone (123-31-9) | HO(C6H4)OH | 110.11 | No | 1992 [48] |
| 1,2-Ethanedisulfonic acid (110-04-3) | HO3S(CH2)2SO3H | 190.18 | No | 1992 [48] |
| m-Benzenedisulfonic acid (98-48-6) | HO3S(C6H4)SO3H | 238.24 | No | 1992 [48] |
*The chemical species of the guest molecule in OCPC is uncertain.
**No description with respect to steric configuration of carboxylic acid.