1,4-Cyclohexanedicarboxylic acid

1,4-Cyclohexanedicarboxylic acid
Identifiers
CAS Number	cis: 619-81-8; trans: 619-82-9; mix: 1076-97-7;
3D model (JSmol)	Interactive image; cis: Interactive image; trans: Interactive image;
ChEBI	CHEBI:145052;
ChEMBL	ChEMBL3187151;
ChemSpider	13484;
ECHA InfoCard	100.012.790
EC Number	214-068-6; trans: 210-614-2;
PubChem CID	14106;
UNII	cis: 68QED0R44U; trans: 18W55738KH;
CompTox Dashboard (EPA)	DTXSID2038788; cis: DTXSID001290604; trans: DTXSID901031536;
	InChI InChI=1S/C8H12O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h5-6H,1-4H2,(H,9,10)(H,11,12) Key: PXGZQGDTEZPERC-UHFFFAOYSA-N; cis: InChI=1S/C8H12O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h5-6H,1-4H2,(H,9,10)(H,11,12)/t5-,6+ Key: PXGZQGDTEZPERC-OLQVQODUSA-N; trans: InChI=1S/C8H12O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h5-6H,1-4H2,(H,9,10)(H,11,12)/t5-,6- Key: PXGZQGDTEZPERC-IZLXSQMJSA-N;
	SMILES C1CC(CCC1C(=O)O)C(=O)O; cis: OC(=O)[C@H]1CC[C@H](CC1)C(O)=O; trans: OC(=O)[C@H]1CC[C@@H](CC1)C(O)=O;
Properties
Chemical formula	C8H12O4
Molar mass	172.180 g·mol−1
Appearance	white solid
Density	1.36 g/cm3
Melting point	312.5 °C (594.5 °F; 585.6 K) 168-170°C for cis isomer
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1,4-Cyclohexanedicarboxylic acid describes a pair of organic compounds with the formula C₆H₁₀(CO₂H)₂. The CO₂H groups are attached to the opposite carbon centers of the cyclohexane ring. These groups can be cis or trans. Other isomers of cyclohexanedicarboxylic acid are known, but the 1,4- isomers are of greatest interest, perhaps because they are obtainable from a commodity chemical. Specifically, hydrogenation of terephthalic acid affords the title compound:^[1]

C₆H₄(CO₂H)₂ + 3 H₂ → C₆H₁₀(CO₂H)₂.

The trans isomer has been more heavily studied. It has been examined as a precursor to polycarbonates^[2] and as a building block for metal-organic frameworks.^[3]

References

^ Maegawa, Tomohiro; Akashi, Akira; Yaguchi, Kiichiro; Iwasaki, Yohei; Shigetsura, Masahiro; Monguchi, Yasunari; Sajiki, Hironao (2009). "Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions". Chemistry - A European Journal. 15 (28): 6953–6963. doi:10.1002/chem.200900361. PMID 19514037.
^ Liu, Jianwei; Yee, Albert F. (1998). "Enhancing Plastic Yielding in Polyestercarbonate Glasses by 1,4-Cyclohexylene Linkage Addition". Macromolecules. 31 (22): 7865–7870. Bibcode:1998MaMol..31.7865L. doi:10.1021/ma980370w.
^ Xiang, Sheng-Chang; Zhang, Zhangjing; Zhao, Cong-Gui; Hong, Kunlun; Zhao, Xuebo; Ding, De-Rong; Xie, Ming-Hua; Wu, Chuan-De; Das, Madhab C.; Gill, Rachel; Thomas, K. Mark; Chen, Banglin (2011). "Rationally tuned micropores within enantiopure metal-organic frameworks for highly selective separation of acetylene and ethylene". Nature Communications. 2: 204. Bibcode:2011NatCo...2..204X. doi:10.1038/ncomms1206. PMID 21343922.

[1] Maegawa, Tomohiro; Akashi, Akira; Yaguchi, Kiichiro; Iwasaki, Yohei; Shigetsura, Masahiro; Monguchi, Yasunari; Sajiki, Hironao (2009). "Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions". Chemistry - A European Journal. 15 (28): 6953–6963. doi:10.1002/chem.200900361. PMID 19514037.

[2] Liu, Jianwei; Yee, Albert F. (1998). "Enhancing Plastic Yielding in Polyestercarbonate Glasses by 1,4-Cyclohexylene Linkage Addition". Macromolecules. 31 (22): 7865–7870. Bibcode:1998MaMol..31.7865L. doi:10.1021/ma980370w.

[3] Xiang, Sheng-Chang; Zhang, Zhangjing; Zhao, Cong-Gui; Hong, Kunlun; Zhao, Xuebo; Ding, De-Rong; Xie, Ming-Hua; Wu, Chuan-De; Das, Madhab C.; Gill, Rachel; Thomas, K. Mark; Chen, Banglin (2011). "Rationally tuned micropores within enantiopure metal-organic frameworks for highly selective separation of acetylene and ethylene". Nature Communications. 2: 204. Bibcode:2011NatCo...2..204X. doi:10.1038/ncomms1206. PMID 21343922.

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