1,10-癸二醇
| 1,10-癸二醇 | |
|---|---|
| |
| |
| 识别 | |
| CAS号 | 112-47-0 |
| PubChem | 37153 |
| SMILES |
|
| EC编号 | 203-975-2 |
| 性质 | |
| 化学式 | C10H22O2 |
| 摩尔质量 | 174.28 g·mol−1 |
| 外观 | 白色固体[1] |
| 密度 | 0.891 g·cm−3 (80 °C)[1] |
| 熔点 | 72–75 °C[1] 81.7 ℃[2] |
| 沸点 | 297 °C (1013 hPa)[1] 170 °C (11 hPa)[1] |
| 溶解性（水） | 难溶[3] |
| 若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。 | |
1,10-癸二醇是化学式 C10H22O2的醇。
制备
[编辑]1,10-癸二醇可以由癸二酸二甲酯在乙醇里和三氯化铈催化下被硼氢化钠还原而成。这个反应的时间为一天，产率 93%。[4]四丁基硼氢化铵还原二硫代癸二酸二乙酯的产物也是1,10-癸二醇。[5]癸二酸二乙酯在液氨中的电化学还原也可以制备1,10-癸二醇，产率 95%。[6]
癸二酸和硼氢化二异丙基钛(III)（(iPrO)2TiBH4，由二氯二异丙基钛和苄基三乙基硼氢化铵在二氯甲烷原位反应产生）的反应也能合成1,10-癸二醇。[7]
性质
[编辑]1,10-癸二醇是难溶于水的白色固体。[1][3]它的熔点是81.7 °C，熔化热 44.0 kJ·mol−1（252.6 J·g−1）。[2]这个分子有锯齿状结构。[8]
反应
[编辑]1,10-癸二醇的溴化会生成1,10-二溴癸烷，[9]而和氯化亚砜的反应则产生1,10-二氯癸烷。[10]
1,10-癸二醇、碘和氨水反应会生成癸二腈，产率高达 99%。[11]
用处
[编辑]1,10-癸二醇和其异构体1,9-癸二醇和1,2-癸二醇一样都是土壤硝化作用的抑制剂，可以减少土壤氮的流失，也避免了农田硝化作用造成的环境问题。这些二醇也会高度抑制亚硝化微生物，即使在低剂量时也是如此。[12]
参考资料
[编辑]- ^ 1.0 1.1 1.2 1.3 1.4 1.5 来源：Sigma-Aldrich Co., product no. D1203 .
- ^ 2.0 2.1 Shen, Jianfen; Cai, Zhengyu; Wang, Chaoming; Liu, Xing; Zheng, Rui. Preparation and thermal performances of 1, 10-decanediol-stearic acid eutectic as phase change material. Thermochimica Acta (Elsevier BV). 2020, 690: 178648. ISSN 0040-6031. doi:10.1016/j.tca.2020.178648.
- ^ 3.0 3.1 Haynes, William. CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. Boca Raton, Florida: CRC Press. 2014: 142. ISBN 978-1-4822-0868-9. OCLC 882266963.
- ^ Xu, Yinan; Wei, Yunyang. CeCl3-Catalyzed Reduction of Methyl Esters of Carboxylic Acids to Corresponding Alcohols with Sodium Borohydride. Synthetic Communications (Informa UK Limited). 2010-10-20, 40 (22): 3423–3429. ISSN 0039-7911. doi:10.1080/00397910903457233.
- ^ Liu, Hsing-Jang; Luo, Weide. Thiol Esters in Organic Synthesis. XV. Reduction with Tetrabutylammonium Borohydride. Synthetic Communications (Informa UK Limited). 1989, 19 (3-4): 387–392. ISSN 0039-7911. doi:10.1080/00397918908050678.
- ^ Chaussard, J.; Combellas, C.; Thiebault, A. Electrochemical reduction in liquid ammonia: electrolytic birch reactions and chemical bond fissions. Tetrahedron Letters (Elsevier BV). 1987, 28 (11): 1173–1174. ISSN 0040-4039. doi:10.1016/s0040-4039(00)95318-8.
- ^ Ravikumar, K. S.; Chandrasekaran, Srinivasan. Reaction of Diisopropoxytitanium(III) Tetrahydroborate with Selected Organic Compounds Containing Representative Functional Groups. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1996-01-01, 61 (3): 826–830. ISSN 0022-3263. doi:10.1021/jo951313t.
- ^ Nakamura, N.; Sato, T. 1,10-Decanediol. Acta Crystallographica Section C Crystal Structure Communications (International Union of Crystallography (IUCr)). 1999-10-15, 55 (10): 1685–1687. ISSN 0108-2701. doi:10.1107/s0108270199008318.
- ^ Rong. Lacquer chemistry and applications. Amsterdam: Elsevier. 2015: 157. ISBN 978-0-12-803610-5. OCLC 916446481.
- ^ Scientific Papers of the Institute of Physical and Chemical Research, The Institute: 12, 1931
- ^ Iida, Shinpei; Togo, Hideo. Direct oxidative conversion of alcohols and amines to nitriles with molecular iodine and DIH in aq NH3. Tetrahedron (Elsevier BV). 2007, 63 (34): 8274–8281. ISSN 0040-4020. doi:10.1016/j.tet.2007.05.106.
- ^ CN105439782A - Use of decanediol as nitrification inhibitor. Google Patents. 2015-12-14 [2022-04-13]. （原始内容存档于2022-04-13）.