1,10-Decanediol is an organic compound diol with the chemical formula (HOCH2(CH2)8CH2OH. It is a white solid with limited solubility in water.[1][2] The molecular configuration of 1,10-decanediol is described as having a zigzag conformation.[3]

Preparation

It is traditionally synthesized by reduction of diesters of sebacic acid, which are readily obtained from natural sources. One method is the Bouveault-Blanc reduction.[4]

Other more specialized reagents have been used such as sodium borohydride/cerium(III) chloride.[5] The electrochemical reduction of diethyl sebacate in liquid ammonia can yield 1,10-decanediol.[6]

Other sebacic acid precursor have been used such as diethyl dithiosebacate with tetrabutylammonium borohydride[7] and sebacic acid itself and diisopropyltitanium(III) borohydride.[8]

Reactions

The bromination of 1,10-decanediol yields 1,10-dibromodecane,[9] whereas the reaction with thionyl chloride results in the formation of 1,10-dichlorodecane.[10] The reaction involving 1,10-decanediol, iodine, and ammonia results in the formation of sebaconitrile.[11]

Uses

Pyrolysis of poly(1,10-decylenecarbonate), the polycarbonate derived from 1,10-decanediol, gives 9-decenol as described by the following idealized equation:[12]

(OCH2(CH2)8CH2O)CO → 2 CH2\dCH(CH2)7CH2OH + CO2

1,10-Decanediol, along with its isomers 1,9-decanediol and 1,2-decanediol, functions as an inhibitor of soil nitrification.[13] This inhibition can mitigate nitrogen loss from soil and prevent the environmental issues associated with nitrification in agricultural settings.[13] Furthermore, these diols exhibit a significant inhibitory effect on nitrite-forming microorganisms, even at low concentrations.[13]

References

  1. ^
  2. ^ Haynes, William (2014). CRC handbook of chemistry and physics: a ready-reference book of chemical and physical data. Boca Raton, Florida: CRC Press. p. 142. ISBN 978-1-4822-0868-9. OCLC 882266963
  3. ^ Nakamura, N. & Sato, T. (1999-10-15). "1,10-Decanediol". Acta Crystallographica Section C Crystal Structure Communications. 55 (10): 1685–1687. International Union of Crystallography (IUCr). Bibcode:1999AcCrC..55.1685N. doi:10.1107/s0108270199008318. ISSN 0108-2701
  4. ^ R. H. Manske (1934). "Decamethylene Glycol". Organic Syntheses. 14: 20. doi:10.15227/orgsyn.014.0020
  5. ^ Xu, Yinan & Wei, Yunyang (2010-10-20). "CeCl3-Catalyzed Reduction of Methyl Esters of Carboxylic Acids to Corresponding Alcohols with Sodium Borohydride". Synthetic Communications. 40 (22): 3423–3429. Informa UK Limited. doi:10.1080/00397910903457233. ISSN 0039-7911
  6. ^ Chaussard, J.; Combellas, C.; Thiebault, A. (1987). "Electrochemical reduction in liquid ammonia: electrolytic birch reactions and chemical bond fissions". Tetrahedron Letters. 28 (11): 1173–1174. Elsevier BV. doi:10.1016/s0040-4039(00)95318-8. ISSN 0040-4039
  7. ^ Liu, Hsing-Jang & Luo, Weide (1989). "Thiol Esters in Organic Synthesis. XV. Reduction with Tetrabutylammonium Borohydride". Synthetic Communications. 19 (3–4): 387–392. Informa UK Limited. doi:10.1080/00397918908050678. ISSN 0039-7911
  8. ^ Ravikumar, K. S. & Chandrasekaran, Srinivasan (1996-01-01). "Reaction of Diisopropoxytitanium(III) Tetrahydroborate with Selected Organic Compounds Containing Representative Functional Groups". The Journal of Organic Chemistry. 61 (3): 826–830. American Chemical Society (ACS). doi:10.1021/jo951313t. ISSN 0022-3263
  9. ^ Rong (2015). Lacquer chemistry and applications. Amsterdam: Elsevier. p. 157. ISBN 978-0-12-803610-5. OCLC 916446481
  10. ^ "Scientific Papers of the Institute of Physical and Chemical Research", The Institute, 1931, p. 12
  11. ^ Iida, Shinpei & Togo, Hideo (2007). "Direct oxidative conversion of alcohols and amines to nitriles with molecular iodine and DIH in aq NH3". Tetrahedron. 63 (34): 8274–8281. Elsevier BV. doi:10.1016/j.tet.2007.05.106. ISSN 0040-4020
  12. ^
  13. ^ "CN105439782A - Use of decanediol as nitrification inhibitor". Google Patents. 2015-12-14. Archived 2022-04-13 at the Wayback Machine. Retrieved 2022-04-13.