麦芽酚碳酸酯的合成及其裂解行为分析

庞登红; 白冰; 祝浩; 罗诚浩; 柯炜昌; 张璟; 黄龙; 毛多斌

doi:10.12187/2024.04.007

CN 41-1437/TS ISSN 2096-1553

麦芽酚碳酸酯的合成及其裂解行为分析

庞登红 , 白冰 , 祝浩 , 罗诚浩 , 柯炜昌 , 张璟 , 黄龙 , 毛多斌

庞登红, 白冰, 祝浩, 等. 麦芽酚碳酸酯的合成及其裂解行为分析[J]. 轻工学报, 2024, 39(4): 50-56. doi: 10.12187/2024.04.007

引用本文: 庞登红, 白冰, 祝浩, 等. 麦芽酚碳酸酯的合成及其裂解行为分析[J]. 轻工学报, 2024, 39(4): 50-56. doi: 10.12187/2024.04.007

PANG Denghong, BAI Bing, ZHU Hao, et al. Synthesis and pyrolysis behavior analysis of maltol carbonates[J]. Journal of Light Industry, 2024, 39(4): 50-56. doi: 10.12187/2024.04.007

Citation: PANG Denghong, BAI Bing, ZHU Hao, et al. Synthesis and pyrolysis behavior analysis of maltol carbonates[J]. Journal of Light Industry, 2024, 39(4): 50-56. doi: 10.12187/2024.04.007

麦芽酚碳酸酯的合成及其裂解行为分析

1. 湖北中烟工业有限责任公司技术中心, 湖北武汉 430000;
2. 郑州轻工业大学烟草科学与工程学院, 河南郑州 450001

作者简介: 庞登红(1983—),男,重庆市人,湖北中烟工业有限责任公司工程师,主要研究方向为新型烟草制品。E-mail:pangdenghong@163.com;

基金项目: 中国烟草总公司项目 (110202201053(SJ-03))
湖北中烟工业有限责任公司科技项目 (2021JSXX3GC2C175)
中图分类号: TS41

Synthesis and pyrolysis behavior analysis of maltol carbonates

1. Technology Center, China Tobacco Hubei Industrial Co., Ltd., Wuhan 430000, China;
2. College of Tobacco Science and Engineering, Zhengzhou University of Light Industry, Zhengzhou 450001, China
Received Date: 2023-08-04
Accepted Date: 2023-09-11
Available Online: 2024-08-15
CLC number: TS41

摘要: 为开发适用于加热卷烟的麦芽酚潜香化合物,将不同种类的醇与麦芽酚通过缩合反应合成7种麦芽酚碳酸酯。利用核磁共振和高分辨质谱技术对产物结构进行确认,并通过热重分析和在线热裂解-气相色谱-质谱联用分析技术考查7种麦芽酚碳酸酯的裂解行为。结果表明:在优化的合成条件下,7种麦芽酚碳酸酯产率范围为83.0%~94.3%;合成的麦芽酚碳酸酯的热失重过程主要存在直接挥发和裂解两种模式;麦芽酚碳酸酯在加热时均可裂解生成麦芽酚,其裂解能力与原料醇的类型密切相关,其中麦芽酚叔丁醇碳酸酯和麦芽酚苯甲醇碳酸酯最易发生裂解,在200 ℃的较低温度下便可迅速裂解并释放麦芽酚,与加热卷烟烟丝受热温度相适应,相比之下,麦芽酚仲醇碳酸酯的裂解能力较弱,而麦芽酚伯醇碳酸酯则难以在低温条件下发生裂解。
- 麦芽酚碳酸酯 /
- 潜香化合物 /
- 裂解 /
- 加热卷烟
Abstract: To develop maltol latent fragrant compounds suitable for heated cigarettes, seven maltol carbonates were synthesized by condensation reaction of maltol with different alcohols. The structures of the products were confirmed by nuclear magnetic resonance and high-resolution mass spectrometry techniques. The pyrolysis behavior of seven maltol carbonates was investigated by thermogravimetric analysis and online pyrolysis gas chromatography-mass spectrometry(Py-GC-MS). The results showed that under the optimized conditions, the yields of seven maltol carbonates ranged from 83.0% and 94.3%; The synthesized maltol carbonate had mainly two weight loss modes: volatilization and pyrolysis; Upon heating, maltol carbonate could be pyrolyzed to produce maltol, and its pyrolysis ability was closely related to the type of raw material alcohol. Maltol tertiary alcohol and benzyl alcohol carbonate were the most easily pyrolyzed, which could rapidly pyrolyze and release maltol at a relatively low temperature, adapted to the heating temperature of the heated cigarettes. In contrast, maltol secondary alcohol carbonate had weaker pyrolysis ability, while maltol primary alcohol carbonate was difficult to pyrolyze at low temperatures.
- maltol carbonate /
- latent fragrant compound /
- pyrolysis /
- heated cigarette
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庞登红, 白冰, 祝浩, 等. 麦芽酚碳酸酯的合成及其裂解行为分析[J]. 轻工学报, 2024, 39(4): 50-56. doi: 10.12187/2024.04.007

引用本文: 庞登红, 白冰, 祝浩, 等. 麦芽酚碳酸酯的合成及其裂解行为分析[J]. 轻工学报, 2024, 39(4): 50-56. doi: 10.12187/2024.04.007

PANG Denghong, BAI Bing, ZHU Hao, et al. Synthesis and pyrolysis behavior analysis of maltol carbonates[J]. Journal of Light Industry, 2024, 39(4): 50-56. doi: 10.12187/2024.04.007

Citation: PANG Denghong, BAI Bing, ZHU Hao, et al. Synthesis and pyrolysis behavior analysis of maltol carbonates[J]. Journal of Light Industry, 2024, 39(4): 50-56. doi: 10.12187/2024.04.007

麦芽酚碳酸酯的合成及其裂解行为分析

作者简介:庞登红(1983—),男,重庆市人,湖北中烟工业有限责任公司工程师,主要研究方向为新型烟草制品。E-mail:pangdenghong@163.com

1. 湖北中烟工业有限责任公司技术中心, 湖北武汉 430000;
2. 郑州轻工业大学烟草科学与工程学院, 河南郑州 450001

收稿日期: 2023-08-04
录用日期: 2023-09-11
网络出版日期: 2024-08-15

基金项目: 中国烟草总公司项目 (110202201053(SJ-03))湖北中烟工业有限责任公司科技项目 (2021JSXX3GC2C175)

关键词:

摘要: 为开发适用于加热卷烟的麦芽酚潜香化合物,将不同种类的醇与麦芽酚通过缩合反应合成7种麦芽酚碳酸酯。利用核磁共振和高分辨质谱技术对产物结构进行确认,并通过热重分析和在线热裂解-气相色谱-质谱联用分析技术考查7种麦芽酚碳酸酯的裂解行为。结果表明:在优化的合成条件下,7种麦芽酚碳酸酯产率范围为83.0%~94.3%;合成的麦芽酚碳酸酯的热失重过程主要存在直接挥发和裂解两种模式;麦芽酚碳酸酯在加热时均可裂解生成麦芽酚,其裂解能力与原料醇的类型密切相关,其中麦芽酚叔丁醇碳酸酯和麦芽酚苯甲醇碳酸酯最易发生裂解,在200 ℃的较低温度下便可迅速裂解并释放麦芽酚,与加热卷烟烟丝受热温度相适应,相比之下,麦芽酚仲醇碳酸酯的裂解能力较弱,而麦芽酚伯醇碳酸酯则难以在低温条件下发生裂解。

English Abstract

Synthesis and pyrolysis behavior analysis of maltol carbonates

1. Technology Center, China Tobacco Hubei Industrial Co., Ltd., Wuhan 430000, China;
2. College of Tobacco Science and Engineering, Zhengzhou University of Light Industry, Zhengzhou 450001, China

Received Date: 2023-08-04
Accepted Date: 2023-09-11
Available Online: 2024-08-15

Abstract: To develop maltol latent fragrant compounds suitable for heated cigarettes, seven maltol carbonates were synthesized by condensation reaction of maltol with different alcohols. The structures of the products were confirmed by nuclear magnetic resonance and high-resolution mass spectrometry techniques. The pyrolysis behavior of seven maltol carbonates was investigated by thermogravimetric analysis and online pyrolysis gas chromatography-mass spectrometry(Py-GC-MS). The results showed that under the optimized conditions, the yields of seven maltol carbonates ranged from 83.0% and 94.3%; The synthesized maltol carbonate had mainly two weight loss modes: volatilization and pyrolysis; Upon heating, maltol carbonate could be pyrolyzed to produce maltol, and its pyrolysis ability was closely related to the type of raw material alcohol. Maltol tertiary alcohol and benzyl alcohol carbonate were the most easily pyrolyzed, which could rapidly pyrolyze and release maltol at a relatively low temperature, adapted to the heating temperature of the heated cigarettes. In contrast, maltol secondary alcohol carbonate had weaker pyrolysis ability, while maltol primary alcohol carbonate was difficult to pyrolyze at low temperatures.

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