1,10-癸二醇

1,10-癸二醇
識別
CAS編號	112-47-0
PubChem	37153
SMILES	OCCCCCCCCCCO;
EC編號	203-975-2
性質
化學式	C10H22O2
摩爾質量	174.28 g·mol−1
外觀	白色固體
密度	0.891 g·cm−3 (80 °C)
熔點	72–75 °C; 81.7 ℃
沸點	297 °C (1013 hPa); 170 °C (11 hPa)
溶解性（水）	難溶
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

1,10-癸二醇是化學式 C₁₀H₂₂O₂的醇。

製備

1,10-癸二醇可以由癸二酸二甲酯在乙醇里和三氯化鈰催化下被硼氫化鈉還原而成。這個反應的時間為一天，產率 93%。^[4]四丁基硼氫化銨還原二硫代癸二酸二乙酯的產物也是1,10-癸二醇。^[5]癸二酸二乙酯在液氨中的電化學還原也可以製備1,10-癸二醇，產率 95%。^[6]

癸二酸和硼氫化二異丙基鈦(III)（(ⁱPrO)₂TiBH₄，由二氯二異丙基鈦和苯甲基三乙基硼氫化銨在二氯甲烷原位反應產生）的反應也能合成1,10-癸二醇。^[7]

性質

1,10-癸二醇是難溶於水的白色固體。^[1]^[3]它的熔點是81.7 °C，熔化熱 44.0 kJ·mol⁻¹（252.6 J·g⁻¹）。^[2]這個分子有鋸齒狀結構。^[8]

反應

1,10-癸二醇的溴化會生成1,10-二溴癸烷，^[9]而和氯化亞碸的反應則產生1,10-二氯癸烷。^[10]

1,10-癸二醇、碘和氨水反應會生成癸二腈，產率高達 99%。^[11]

用處

1,10-癸二醇和其異構體1,9-癸二醇和1,2-癸二醇一樣都是土壤硝化作用的抑制劑，可以減少土壤氮的流失，也避免了農田硝化作用造成的環境問題。這些二醇也會高度抑制亞硝化（英語：Nitrosation）微生物，即使在低劑量時也是如此。^[12]

參考資料

^ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 來源：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]. （原始內容存檔於2022-04-13）.

[Sigma-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 來源：Sigma-Aldrich Co., product no. D1203 .

[Shen-2] 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.

[William_M._Haynes-3] 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.

[4] 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.

[5] 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.

[6] 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.

[7] 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.

[DOI10.1107/S0108270199008318-8] 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_Lu,_Tetsuo_Miyakoshi-9] Rong. Lacquer chemistry and applications. Amsterdam: Elsevier. 2015: 157. ISBN 978-0-12-803610-5. OCLC 916446481.

[10] Scientific Papers of the Institute of Physical and Chemical Research, The Institute: 12, 1931

[11] 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.

[12] CN105439782A - Use of decanediol as nitrification inhibitor. Google Patents. 2015-12-14 [2022-04-13]. （原始內容存檔於2022-04-13）.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]