1,10-Decanediol

1,10-Decanediol
Names
Preferred IUPAC name
Decane-1,10-diol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.614
EC Number
  • 203-975-2
UNII
  • InChI=1S/C10H22O2/c11-9-7-5-3-1-2-4-6-8-10-12/h11-12H,1-10H2
    Key: FOTKYAAJKYLFFN-UHFFFAOYSA-N
  • OCCCCCCCCCCO
Properties
C10H22O2
Molar mass 174.284 g·mol−1
Appearance White solid[1]
Density 0.891 g·cm−3 (80 °C)[1]
Melting point 72–75 °C[1]
81.7 °C[2] Heat of fusion = 44.0 kJ·mol−1 (252.6 J·g−1).[2]
Boiling point 297 °C (1013 hPa)[1]
170 °C (11 hPa)[1]
Poorly soluble[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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][3] The molecular configuration of 1,10-decanediol is described as having a zigzag conformation.[4]

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.[5]

Other more specialized reagents have been used such as sodium borohydride/cerium(III) chloride.[6] The electrochemical reduction of diethyl sebacate in liquid ammonia can yield 1,10-decanediol.[7]

Other sebacic acid precursor have been used such as diethyl dithiosebacate with tetrabutylammonium borohydride[8] and sebacic acid itself and diisopropyltitanium(III) borohydride.[9]

Reactions

The bromination of 1,10-decanediol yields 1,10-dibromodecane,[10] whereas the reaction with thionyl chloride results in the formation of 1,10-dichlorodecane.[11] The reaction involving 1,10-decanediol, iodine, and ammonia results in the formation of sebaconitrile.[12]

Uses

Pyrolysis of poly(1,10-decylenecarbonate), the polycarbonate derived from 1,10-decanediol, gives 9-decenol as described by the following idealized equation:[13]

(OCH2(CH2)8CH2O)CO → 2 CH2=CH(CH2)7CH2OH + CO2

1,10-Decanediol, along with its isomers 1,9-decanediol and 1,2-decanediol, functions as an inhibitor of soil nitrification.[14] This inhibition can mitigate nitrogen loss from soil and prevent the environmental issues associated with nitrification in agricultural settings.[14] Furthermore, these diols exhibit a significant inhibitory effect on nitrite-forming microorganisms, even at low concentrations.[14]

References

  1. ^ a b c d e f Sigma-Aldrich Co., product no. D1203.
  2. ^ a b 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 178648. Elsevier BV. Bibcode:2020TcAc..69078648S. doi:10.1016/j.tca.2020.178648. ISSN 0040-6031.
  3. ^ a b 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. ^ 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.
  5. ^ R. H. Manske (1934). "Decamethylene Glycol". Organic Syntheses. 14: 20. doi:10.15227/orgsyn.014.0020.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ Rong (2015). Lacquer chemistry and applications. Amsterdam: Elsevier. p. 157. ISBN 978-0-12-803610-5. OCLC 916446481.
  11. ^ Scientific Papers of the Institute of Physical and Chemical Research, The Institute, 1931, p. 12
  12. ^ 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.
  13. ^ Buysch, Hans-Josef (2012). "Carbonic Esters". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_197. ISBN 3527306730.
  14. ^ a b c "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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