1,10-Decanediol
{{Chembox
|ImageFile1=1,10-Decanediol.svg
|ImageFile2=1,10-decanodiol-3D.gif
|Section1={{Chembox Identifiers
| CASNo= 112-47-0
| EINECS= 203-975-2
| PubChem= 37153
| ChemSpiderID= 34095
| UNII = 5I577UDK52
| StdInChI=1S/C10H22O2/c11-9-7-5-3-1-2-4-6-8-10-12/h11-12H,1-10H2
| StdInChIKey = FOTKYAAJKYLFFN-UHFFFAOYSA-N
|SMILES=OCCCCCCCCCCO
}}
|Section2={{Chembox Properties
| Appearance= White solid{{Sigma-Aldrich|Aldrich|id=D1203|Name=1,10-Decandiol, 98%|Abruf=2015-04-30}}
|C=10|H=22|O=2
| Density= 0.891 g·cm−3 (80 °C)
| BoilingPt=297 °C (1013 hPa)
170 °C (11 hPa)
}}
}}
1,10-Decanediol is a diol with the chemical formula C10H22O2.
It 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%.{{cite journal | last1=Xu | first1=Yinan | last2=Wei | first2=Yunyang | title=CeCl3-Catalyzed Reduction of Methyl Esters of Carboxylic Acids to Corresponding Alcohols with Sodium Borohydride | journal=Synthetic Communications | publisher=Informa UK Limited | volume=40 | issue=22 | date=2010-10-20 | issn=0039-7911 | doi=10.1080/00397910903457233 | pages=3423–3429}} The product of the reduction of diethyl dithiosebacate by tetrabutylammonium borohydride is also 1,10-decanediol.{{cite journal | last1=Liu | first1=Hsing-Jang | last2=Luo | first2=Weide | title=Thiol Esters in Organic Synthesis. XV. Reduction with Tetrabutylammonium Borohydride | journal=Synthetic Communications | publisher=Informa UK Limited | volume=19 | issue=3–4 | year=1989 | issn=0039-7911 | doi=10.1080/00397918908050678 | pages=387–392}} The electrochemical reduction of diethyl sebacate in liquid ammonia can yield 1,10-decanediol with an impressive efficiency of 95%.{{cite journal | last1=Chaussard | first1=J. | last2=Combellas | first2=C. | last3=Thiebault | first3=A. | title=Electrochemical reduction in liquid ammonia: electrolytic birch reactions and chemical bond fissions | url=https://archive.org/details/sim_tetrahedron-letters_1987_28_11/page/1173 | journal=Tetrahedron Letters | publisher=Elsevier BV | volume=28 | issue=11 | year=1987 | issn=0040-4039 | doi=10.1016/s0040-4039(00)95318-8 | pages=1173–1174}}
The interaction between sebacic acid and diisopropyltitanium(III) borohydride ((iPrO)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.{{cite journal | last1=Ravikumar | first1=K. S. | last2=Chandrasekaran | first2=Srinivasan | title=Reaction of Diisopropoxytitanium(III) Tetrahydroborate with Selected Organic Compounds Containing Representative Functional Groups | journal=The Journal of Organic Chemistry | publisher=American Chemical Society (ACS) | volume=61 | issue=3 | date=1996-01-01 | issn=0022-3263 | doi=10.1021/jo951313t | pages=826–830}}
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−1 (252.6 J·g−1).{{cite journal | last1=Shen | first1=Jianfen | last2=Cai | first2=Zhengyu | last3=Wang | first3=Chaoming | last4=Liu | first4=Xing | last5=Zheng | first5=Rui | title=Preparation and thermal performances of 1, 10-decanediol-stearic acid eutectic as phase change material | journal=Thermochimica Acta | publisher=Elsevier BV | volume=690 | year=2020 | issn=0040-6031 | doi=10.1016/j.tca.2020.178648 | page=178648| bibcode=2020TcAc..69078648S }} The molecular configuration of 1,10-decanediol is described as having a zigzag conformation.{{cite journal | last1=Nakamura | first1=N. | last2=Sato | first2=T. | title=1,10-Decanediol | journal=Acta Crystallographica Section C Crystal Structure Communications | publisher=International Union of Crystallography (IUCr) | volume=55 | issue=10 | date=1999-10-15 | issn=0108-2701 | doi=10.1107/s0108270199008318 | pages=1685–1687| bibcode=1999AcCrC..55.1685N }} The bromination of 1,10-decanediol yields 1,10-dibromodecane,{{cite book | author=Rong | title=Lacquer chemistry and applications | publisher=Elsevier | publication-place=Amsterdam | year=2015 | isbn=978-0-12-803610-5 | oclc=916446481 |page=157}} whereas the reaction with thionyl chloride results in the formation of 1,10-dichlorodecane.{{citation|title=Scientific Papers of the Institute of Physical and Chemical Research |publisher=The Institute |date=1931 |page=12 }} The reaction involving 1,10-decanediol, iodine, and ammonia results in the formation of sebaconitrile with a yield of 99%.{{cite journal | last1=Iida | first1=Shinpei | last2=Togo | first2=Hideo | title=Direct oxidative conversion of alcohols and amines to nitriles with molecular iodine and DIH in aq NH3 | journal=Tetrahedron | publisher=Elsevier BV | volume=63 | issue=34 | year=2007 | issn=0040-4020 | doi=10.1016/j.tet.2007.05.106 | pages=8274–8281}}
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.{{cite web | title=CN105439782A - Use of decanediol as nitrification inhibitor | website=Google Patents | date=2015-12-14 | url=https://patents.google.com/patent/CN105439782A/en?q=%221%2c10-Decanediol+synthesis%22&oq=%221%2c10-Decanediol+synthesis%22 | ref={{sfnref | Google Patents | 2015}} | access-date=2022-04-13 | archive-date=2022-04-13 | archive-url=https://web.archive.org/web/20220413003658/https://patents.google.com/patent/CN105439782A/en?q=%221,10-Decanediol+synthesis%22&oq=%221,10-Decanediol+synthesis%22 }}