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Oxalate for preparing ambrox or releasing ambrox in cigarette smoke and its use

A technology for ambrox and cigarette smoke, which is applied in the fields of application, tobacco, and tobacco treatment, etc. It can solve the problems that the thermal decomposition efficiency is not as good as the thermal decomposition efficiency of oxalate, and the release efficiency is not very effective.

Active Publication Date: 2005-02-23
CHINA TOBACCO HUNAN INDAL CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, we believe that although it releases Ambrox into cigarette smoke, its release efficiency is not very effective. The reason is that the thermal stability of carbonate is still high, which is higher than that of oxalate, and its thermal decomposition efficiency Not as efficient as oxalate thermal decomposition

Method used

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  • Oxalate for preparing ambrox or releasing ambrox in cigarette smoke and its use
  • Oxalate for preparing ambrox or releasing ambrox in cigarette smoke and its use
  • Oxalate for preparing ambrox or releasing ambrox in cigarette smoke and its use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Preparation of (2-hydroxy-2,5,5,8a-tetramethyl-decalinyl)ethanol oxalate diester

[0027] Dissolve 0.02mol (2-hydroxy-2,5,5,8a-tetramethyl-decalinyl)ethanol in 30ml THF, add 3.2ml pyridine, cool with ice water, add dropwise 0.04mol oxalyl chloride while stirring. It was then stirred at room temperature for 24 hours. Add 10mL of ethanol, stir for 30 minutes, add crushed ice and 40mL 2NHCl, extract with ether (200mL×3), combine the ether layers, wash with 2NHCl, water and NaHCO 3 The aqueous solution was washed separately, dried with sodium sulfate, and the solvent was removed under reduced pressure to obtain white crystals, which were filtered by suction and dried in vacuum to obtain the oxalic acid of (2-hydroxy-2,5,5,8a-tetramethyl-decalinyl)ethanol Diester, about 80% yield.

[0028] H NMR spectrum 1 HNMR (400MHz, CDCl 3 ): δ0.788(s, 12H, 4CH 3 ), 0.874(s, 6H, 2CH 3 ), 1.191(s, 6H, 2CH 3 ), 0.899-1.692 (m, 26H), 1.876-1.924 (m, 2H), 3.415-3.806 (m, 4H), 3.18-4.1...

Embodiment 2

[0032] Preparation of (2-hydroxy-2,5,5,8a-tetramethyl-decalinyl) ethyl oxalate

[0033]Add 0.02mol (2-hydroxy-2,5,5,8a-tetramethyl-decalinyl)ethanol, add 0.1g of sodium methoxide and 50ml of diethyl oxalate, and distill off the generated ethanol at 80°C under reduced pressure. After the reaction was completed, (2-hydroxy-2,5,5,8a-tetramethyl-decalinyl)ethanol ethyl oxalate was separated by column chromatography. Mass spectral data m / z (abundance): 354 (M+, <1), 236 (2), 221 (100), 195 (20), 177 (18), 151 (90), 123 (25), 95 ( 60), 69(40). The substance was confirmed to be ethyl (2-hydroxy-2,5,5,8a-tetramethyl-decalinyl)ethanol oxalate by analyzing its primary mass spectrum data.

Embodiment 3

[0035] The thermal analysis experiment of the oxalic acid diester of (2-hydroxy-2,5,5,8a-tetramethyl-decalinyl)ethanol shows that the low volatility of these compounds is extremely easy to completely decompose when heated chemical properties.

[0036] Thermal analysis experiment of oxalic acid diester of (2-hydroxy-2,5,5,8a-tetramethyl-decalinyl)ethanol

[0037] Accurately weigh about 10 mg of oxalic acid diester of (2-hydroxy-2,5,5,8a-tetramethyl-decalinyl)ethanol, and measure TG and DSC curves on a NETZSH-STA 449C thermal analyzer.

[0038] The thermal analysis curve of the oxalic acid diester of (2-hydroxy-2,5,5,8a-tetramethyl-decalinyl)ethanol is shown in figure 1 . Its melting point is measured to be 129.0-131.4°C, indicating that its volatility is low. This compound decomposes completely between 162-211°C, with a weight loss rate of 98.2%, indicating that it is almost completely decomposed when heated, and can be converted into other components very effectively when h...

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PUM

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Abstract

An application of the oxalate in preparing norambrether or releasing the norambrether to the smoke of cigaretter is disclosed. Said oxalate may be decahydro-2-hydroxy-2,5,5,8a-tetramethyl-naphthal eneethanol or 2-hydroxy-2,5,5,9-tetramethyl decalyl ethanol. It can be proportionally added to cigarette, or can be decomposed to obtain norambrether.

Description

technical field [0001] The present invention relates to a novel oxalate ester for preparing ambrox or releasing ambrox into cigarette smoke and its application. Background technique [0002] Respermoids are the key aroma components of oriental cigarettes, and Ambrox is one of the spices with a particularly prominent effect, which makes an important contribution to the smoke of mixed cigarettes. Ambrox is also widely used in flue-cured cigarettes and in the manufacture of perfumes. Because Ambrox has a small molecular weight and strong volatility, its boiling point is only 122-124°C, and its threshold value is low, it is easy to be lost during processing and storage, resulting in unstable quality of cigarettes. [0003] Ambrox is widely used in the flavoring of the cigarette industry and the flavoring of daily chemicals, especially in the manufacture of perfumes. There are many ways to prepare it. Some use ionone as a raw material, and some use sclareol or abbitol as a raw...

Claims

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Application Information

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IPC IPC(8): A24B15/34C07C69/738C07D307/77
Inventor 杨华武黎艳玲周宇邓昌健付见山
Owner CHINA TOBACCO HUNAN INDAL CORP
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