长链脂肪醇氯甲酸酯的合成
The Synthesis of Long Chain Alkyl Chloroformate
DOI: 10.12677/AMC.2021.93011, PDF,   
作者: 方成涛, 肖孝辉*:浙江师范大学,化学与生命科学学院,浙江 金华
关键词: 氯甲酸酯长链脂肪醇三光气合成Chloroformate Long-Chain Fatty Alcohols Triphosgene Synthesis
摘要: 在5℃~10℃下,以石油醚为溶剂、吡啶为缚酸剂,通过长链脂肪醇与三光气反应,制备得到长链脂肪醇氯甲酸酯,收率达到80%以上,含量超过95%。以氯甲酸十二醇酯为例,正十二醇投料放大到41.1 g,氯甲酸十二醇酯收率和含量分别达到89.5%和98.5%,吡啶回收率达到88.1%,该工艺操作简单、安全,具有良好的应用前景。
Abstract: With petroleum ether as solvent and pyridine as acid binding agent, a series of chloroformic esters of long-chain fatty alcohols were synthesized by the reaction of long chain fatty alcohol with triphosgene at 5˚C~10˚C. The yields of chloroformates were over 80% and the content was over 95%. Taking dodecanol chloroformate as an example, the yield and content of dodecanol chloroformate were up to 89.5% and 98.5% respectively when the dosage of n-dodecanol is 41.1g, and the recovery of pyridine reaches 88.1%. The process is simple, safe and has a good application prospect.
文章引用:方成涛, 肖孝辉. 长链脂肪醇氯甲酸酯的合成[J]. 材料化学前沿, 2021, 9(3): 86-91. https://doi.org/10.12677/AMC.2021.93011

参考文献

[1] 孙逊, 林国强, 陆洪福, 等. 紫杉烷类衍生物及其制备方法和药用用途[P]. 中国专利, 101012210. 2007.
[2] 赵毓, 周莎, 边强, 等. 一类烯啶胺酰基衍生物的合成及其应用[P]. 中国专利, 111978244. 2020.
[3] 穆慧敏, 韩志惠, 张铁柱, 等. 高纯氯甲酸苄酯无溶剂生产工艺的研究[J]. 天津化工, 2009, 23(5): 34-36.
[4] Jeong, Y., Jwa, D.G., You, A., et al. (2019) Photochemical Control of Polydopamine Coating in an Aprotic Organic Solvent. Asian Journal of Organic Chemistry, 8, 1610-1612.
[Google Scholar] [CrossRef
[5] Paolo, F., Ivan, M., Elisabetta, R., et al. (2003) Polycaprolactone-Poly(Ethylene Glycol) Multiblock Copolymers as Potential Substitutes for Di(Ethylhexyl) Phthalate in Flexible Poly(Vinyl Chloride) Formulations. Biomacromolecules, 4, 181-188.
[Google Scholar] [CrossRef] [PubMed]
[6] 周祖新, 顾建生. 双光气法合成氯甲酸-9-芴甲酯[J]. 精细石油化工, 2004, 1(1): 37-39.
[7] Venkatesh, Y., Nandi, S., Shee, M., et al. (2017) Bis-Acetyl Carbazole: A Photoremovable Protecting Group for Sequential Release of Two Different Functional Groups and Its Application in Therapeutic Release. European Journal of Organic Chemistry, 2017, 6121-6130.
[Google Scholar] [CrossRef
[8] Gagnard, V., Leydet, A., Morère, A., et al. (2004) Synthesis and in vitro Evaluation of S-Acyl-3-Thiopropyl Prodrugs of Foscarnet. Bioorganic & Medicinal Chemistry, 12, 1393-1402.
[Google Scholar] [CrossRef] [PubMed]
[9] Figlus, M., Wellaway, N., Cooper, A.W.J., et al. (2011) Synthesis of Arrays Using Low Molecular Weight MPEG-Assisted Mitsunobu Reaction. ACS Combinatorial Science, 13, 280-285.
[Google Scholar] [CrossRef] [PubMed]
[10] Pasquato, L., Modena, G., Cotarca, L., Delogu, P., Mantovani, S. (2000) Conversion of Bis(Trichloromethyl) Carbonate to Phosgene and Reactivity of Triphosgene, Diphosgene, and Phosgene with Methano. Journal of Organic Chemistry, 65, 8224-8228.
[Google Scholar] [CrossRef] [PubMed]
[11] Mannuthodikayil, J., Singh, S., Biswas, A., et al. (2019) Benzimidazolinone-Free Peptide o-Aminoanilides for Chemical Protein Synthesis. Organic Letters, 21, 9040-9044.
[Google Scholar] [CrossRef] [PubMed]
[12] 李兴, 常宏宏, 魏文珑. 以固体光气为原料合成邻苯二甲酰氯的工艺研究[J]. 应用化工, 2010, 39(5): 716-719.
[13] 童国通, 谢建武, 周小锋. 氯甲酸苄酯的非光气法合成研究[J]. 化学世界, 2007, 48(4): 226-227+231.
[14] Wang, Q.M. and Huang, R.Q. (2001) Synthesis and Biological Activity of Novel N’-Tert-Butyl-N’-Substituted Benzoyl-N-(Substituted Phenyl) Aminocarbonylhydrazines and Their Derivatives. Tetrahedron Letters, 42, 8881-8883.
[Google Scholar] [CrossRef