Draft:Dicyclohexyl ether

Dicyclohexyl ether
Names
	IUPAC name Cyclohexyloxycyclohexane
	Other names Dicyclohexyl ether; 1,1'-Oxybis[cyclohexane]; 1,1'-Oxybis(cyclohexane); Cyclohexyl ether; Oxydicyclohexane;
Identifiers
CAS Number	4645-15-2;
3D model (JSmol)	Interactive image;
EC Number	225-075-9;
PubChem CID	20757;
CompTox Dashboard (EPA)	DTXSID70196843;
	InChI InChI=1S/C12H22O/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h11-12H,1-10H2 Key: OCDXZFSOHJRGIL-UHFFFAOYSA-N;
	SMILES C1CCCCC1OC2CCCCC2;
Properties
Chemical formula	(C6H11)2O
Molar mass	182.307 g·mol−1
Appearance	Colorless liquid
Density	0.9227 g/ml
Melting point	−36 °C (−33 °F; 237 K)
Boiling point	244 °C (471 °F; 517 K)
Refractive index (nD)	1.4741 (estimate)
Hazards
Flash point	94 °C (201 °F; 367 K)
Related compounds
Related compounds	Diphenyl ether
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Submission declined on 5 August 2026 by Sulfurboy (talk).

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Declined by Sulfurboy 20 days ago. Last edited by Citation bot 19 days ago. Reviewer: Inform author.

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Submission declined on 30 May 2026 by WeirdNAnnoyed (talk).

This draft's references do not show that the subject meets Wikipedia's criteria for inclusion. The draft requires multiple published secondary sources that:

provide significant coverage: discuss the subject in detail, not just brief mentions or routine announcements;
are reliable: from reputable outlets with editorial oversight;
are independent: not connected to the subject, such as interviews, press releases, the subject's own website, or sponsored content.

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Declined by WeirdNAnnoyed 2 months ago.

Submission declined on 19 May 2026 by PeriodicEditor (talk).

This draft's references do not show that the subject meets Wikipedia's criteria for inclusion. The draft requires multiple published secondary sources that:

provide significant coverage: discuss the subject in detail, not just brief mentions or routine announcements;
are reliable: from reputable outlets with editorial oversight;
are independent: not connected to the subject, such as interviews, press releases, the subject's own website, or sponsored content.

Please add references that meet all three of these criteria. If none exist, the subject is not yet suitable for Wikipedia.

Declined by PeriodicEditor 3 months ago.

Comment: Chemical book is considered an unreliable source. Information sourced from there needs to be removed and sourced from elsewhere. Sulfurboy (talk) 03:41, 5 August 2026 (UTC)

Comment: Non-notable compound, based on the sources provided, which are all database entries or primary research articles. Secondary sources are needed. WeirdNAnnoyed (talk) 21:01, 30 May 2026 (UTC)

Dicyclohexyl ether is an organic compound with the chemical formula (C₆H₁₁)₂O. It is a colorless liquid. It composes of two cyclohexyl groups attached to one oxygen atom.

Synthesis

Cyclohexanol can be converted to dicyclohexyl ether by cation-exchanged bentonite clays as a catalyst. Bentonite clays that exchange Al³⁺, Co²⁺ and Na⁺ cations are used in etherification of cyclohexanol to dicyclohexyl ether. Product yields obtained for metal cation exchanged clays are in the order Al³⁺ > Co²⁺ > Na⁺.^[5]

Dicyclohexyl ether can also be synthesized from cyclohexanol by heating it to 134 to 138 °C (273 to 280 °F) in the presence of sulfuric acid as a catalyst, for 1 to 1.5 hours, in an oil bath.^[6]

2 C₆H₁₁OH → (C₆H₁₁)₂O + H₂O

Dicyclohexyl ether can also be obtained by heating cyclohexanol with tungstic acid at 100 °C (212 °F). Two cyclohexanol molecules condense to form the ether and water as a byproduct. The condensation is completed after 13 days.^[7]

Uses

Dicyclohexyl ether is used for research and development only. It is not used for medicinal, household or other use.^[8] It can serve as a new hydroxy-protecting group for serine and threonine in peptide synthesis.^[9]

References

1 2 3 4 PubChem. "1,1'-Oxybis[cyclohexane]". pubchem.ncbi.nlm.nih.gov. Retrieved 29 April 2026.
↑ ChemSpider. "Cyclohexyl ether". www.chemspider.com. Retrieved 29 April 2026.
1 2 3 4 TCI. "Oxydicyclohexane". www.tcichemicals.com. Retrieved 29 April 2026.
1 2 3 Chemical Book. "1,1'-oxybis(cyclohexane)". www.chemicalbook.com. Retrieved 29 April 2026.
↑ Chatterjee, Debabrata; Mody, H.M.; Bhatt, K.N. (1995). "Conversion of cyclohexanol to dicyclohexyl ether catalyzed by cation-exchanged bentonite clays". Journal of Molecular Catalysis A: Chemical. 104 (2): L115–L118. doi:10.1016/1381-1169(95)00206-5.
↑ "Preparation method of dicyclohexyl ether".
↑ Alrefaee, Salhah Hamed; Apblett, Allen W. (2019). "Methods for the reaction of alkenes with activated tungstic acid". Heliyon. 5 (11) e02780. Bibcode:2019Heliy...502780A. doi:10.1016/j.heliyon.2019.e02780. PMC 6895725. PMID 31844714.
↑ Chemical Book. "1,1'-oxybis(cyclohexane)" (PDF). www.chemicalbook.com. Retrieved 29 April 2026.
↑ Nishiyama, Yasuhiro; Shikama, Suguru; Morita, Ken-Ichi; Kurita, Keisuke (2000). "Cyclohexyl ether as a new hydroxy-protecting group for serine and threonine in peptide synthesis". Journal of the Chemical Society, Perkin Transactions 1 (12): 1949–1954. doi:10.1039/B001261K.

[pubchem-1] 1 2 3 4 PubChem. "1,1'-Oxybis[cyclohexane]". pubchem.ncbi.nlm.nih.gov. Retrieved 29 April 2026.

[chemspider-2] ChemSpider. "Cyclohexyl ether". www.chemspider.com. Retrieved 29 April 2026.

[tcichemicals-3] 1 2 3 4 TCI. "Oxydicyclohexane". www.tcichemicals.com. Retrieved 29 April 2026.

[chemicalbook-4] 1 2 3 Chemical Book. "1,1'-oxybis(cyclohexane)". www.chemicalbook.com. Retrieved 29 April 2026.

[sciencedirect-5] Chatterjee, Debabrata; Mody, H.M.; Bhatt, K.N. (1995). "Conversion of cyclohexanol to dicyclohexyl ether catalyzed by cation-exchanged bentonite clays". Journal of Molecular Catalysis A: Chemical. 104 (2): L115–L118. doi:10.1016/1381-1169(95)00206-5.

[patents-google-6] "Preparation method of dicyclohexyl ether".

[7] Alrefaee, Salhah Hamed; Apblett, Allen W. (2019). "Methods for the reaction of alkenes with activated tungstic acid". Heliyon. 5 (11) e02780. Bibcode:2019Heliy...502780A. doi:10.1016/j.heliyon.2019.e02780. PMC 6895725. PMID 31844714.

[chemicalbook-msds-8] Chemical Book. "1,1'-oxybis(cyclohexane)" (PDF). www.chemicalbook.com. Retrieved 29 April 2026.

[9] Nishiyama, Yasuhiro; Shikama, Suguru; Morita, Ken-Ichi; Kurita, Keisuke (2000). "Cyclohexyl ether as a new hydroxy-protecting group for serine and threonine in peptide synthesis". Journal of the Chemical Society, Perkin Transactions 1 (12): 1949–1954. doi:10.1039/B001261K.

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