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1,10-Decanediol

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1,10-Decanediol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.614 Edit this at Wikidata
EC Number
  • 203-975-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H22O2/c11-9-7-5-3-1-2-4-6-8-10-12/h11-12H,1-10H2Key: FOTKYAAJKYLFFN-UHFFFAOYSA-N
SMILES
  • OCCCCCCCCCCO
Properties
Chemical formula C10H22O2
Molar mass 174.284 g·mol
Appearance White solid
Density 0.891 g·cm (80 °C)
Melting point 72–75 °C
81.7 °C
Boiling point 297 °C (1013 hPa)
170 °C (11 hPa)
Solubility in water Poorly soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

1,10-Decanediol is a diol compound characterized by the chemical formula C10H22O2.

Preparation

1,10-Decanediol can be synthesized through the reduction of dimethyl sebacate using sodium borohydride in an ethanol medium, with Cerium(III) chloride serving as the catalyst. The reaction duration is one day, resulting in a yield of 93%. The product of the reduction of diethyl dithiosebacate by tetrabutylammonium borohydride is also 1,10-Decanediol. The electrochemical reduction of diethyl sebacate in liquid ammonia can yield 1,10-Decanediol with an impressive efficiency of 95%.

The interaction between sebacic acid and diisopropyltitanium(III) borohydride ((PrO)2TiBH4), which is generated through the in situ reaction of diisopropyltitanium dichloride and benzyltriethylammonium borohydride in dichloromethane, can also facilitate the synthesis of 1,10-Decanediol.

Properties

1,10-Decanediol is characterized as a white solid with limited solubility in water. It exhibits a melting point of 81.7 °C and a heat of fusion of 44.0 kJ·mol (252.6 J·g). The molecular configuration of 1,10-decanediol is described as having a zigzag conformation.

Reactions

The bromination of 1,10-decanediol yields 1,10-Dibromodecane, whereas the reaction with thionyl chloride results in the formation of 1,10-dichlorodecane.

The reaction involving 1,10-decanediol, iodine, and ammonia results in the formation of sebaconitrile with a yield of 99%.

Usage

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

References

  1. ^ Sigma-Aldrich Co., product no. D1203.
  2. ^ Shen, Jianfen; Cai, Zhengyu; Wang, Chaoming; Liu, Xing; Zheng, Rui (2020). "Preparation and thermal performances of 1, 10-decanediol-stearic acid eutectic as phase change material". Thermochimica Acta. 690. Elsevier BV: 178648. Bibcode:2020TcAc..69078648S. doi:10.1016/j.tca.2020.178648. ISSN 0040-6031.
  3. ^ 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.
  4. 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). Informa UK Limited: 3423–3429. doi:10.1080/00397910903457233. ISSN 0039-7911.
  5. Liu, Hsing-Jang; Luo, Weide (1989). "Thiol Esters in Organic Synthesis. XV. Reduction with Tetrabutylammonium Borohydride". Synthetic Communications. 19 (3–4). Informa UK Limited: 387–392. doi:10.1080/00397918908050678. 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). Elsevier BV: 1173–1174. doi:10.1016/s0040-4039(00)95318-8. ISSN 0040-4039.
  7. 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). American Chemical Society (ACS): 826–830. doi:10.1021/jo951313t. ISSN 0022-3263.
  8. Nakamura, N.; Sato, T. (1999-10-15). "1,10-Decanediol". Acta Crystallographica Section C Crystal Structure Communications. 55 (10). International Union of Crystallography (IUCr): 1685–1687. Bibcode:1999AcCrC..55.1685N. doi:10.1107/s0108270199008318. ISSN 0108-2701.
  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). Elsevier BV: 8274–8281. doi:10.1016/j.tet.2007.05.106. ISSN 0040-4020.
  12. ^ "CN105439782A - Use of decanediol as nitrification inhibitor". Google Patents. 2015-12-14. Archived from the original on 2022-04-13. Retrieved 2022-04-13.
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