WO2010003299A1 - A flavor enhancer and preparation method thereof - Google Patents
A flavor enhancer and preparation method thereof Download PDFInfo
- Publication number
- WO2010003299A1 WO2010003299A1 PCT/CN2008/073427 CN2008073427W WO2010003299A1 WO 2010003299 A1 WO2010003299 A1 WO 2010003299A1 CN 2008073427 W CN2008073427 W CN 2008073427W WO 2010003299 A1 WO2010003299 A1 WO 2010003299A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dimethyl
- isopropyl
- reaction
- trimethyl
- dioxan
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/88—Taste or flavour enhancing agents
Definitions
- the present invention relates to an organic compound and a process for the preparation thereof, and more particularly to a flavoring agent and a process for the preparation thereof.
- Cigarette products are a special consumer product, and the application of flavors and fragrances for cigarettes is regarded as one of the key technologies of cigarette products.
- the cigarette case When the cigarette case is opened, it can emit a fragrant and fragrant scent. When it is pumped, it can produce the odor and aroma of the mellow alcohol.
- the scent tends to become a smoking habit of the consumer, and it is also one of the leading factors guiding the consumption habit, and Adding flavor and flavor can also improve and conceal the bad taste and atmosphere brought by different tobacco leaves, and maintain the stable style of cigarette products. Therefore, the research on tobacco flavors and fragrances has become the core technology of cigarette enterprises, and it is also the main means for cigarette companies to attract and guide consumers.
- Tobacco flavors are mainly derived from natural and artificial chemical synthesis, and are generally classified into natural flavors and synthetic flavors.
- the synthetic perfume refers to a perfume compound obtained by artificial synthesis, and can be classified into alcohols, ethers, aldehydes, ketones, esters, acids, and heterocyclics according to the functional groups thereof. These materials can be classified into sweeteners, flavoring agents, sour agents, humectants, oxidizers, preservatives, and the like, depending on their function on the cigarette.
- flavoring agents have the advantages of enhancing and increasing the aroma of tobacco products, masking the gas, and often used to compensate the smoke, especially in low-tar cigarettes.
- the object of the present invention is to provide a 4-isopropyl-5,5-dimethyl-m-dioxan-2-one compound which has a scent-like and tobacco-like scent and is available.
- the aroma of food, soap, toothpaste, cosmetics, smoking products and detergents makes the aroma of this flavored product more gentle and pleasant.
- Another object of the invention is to provide a process for the preparation of this compound.
- the chemical name of the present invention is 4-isopropyl-5,5-dimethyl-m-dioxan-2-one (common name, cyclic carbonate), which has the following structure:
- the cyclic carbonate has a scent-like and tobacco-like scent. It is widely used for flavoring foods, soaps, toothpastes, cosmetics, smoking products and detergents.
- the aroma of the product is milder and more pleasant.
- the invention uses isobutyraldehyde as a starting material to synthesize a cyclic carbonate by aldol condensation and esterification reaction, and the product can enhance the aroma and aroma thereof in foods, smoking articles, etc., and the coumarin is given to the product.
- Isoindole 1-3- ⁇ 3 ⁇ 43-triple S3 ⁇ 4 3 ⁇ 44 trimethyl-1,3-J£T1 isobutyraldehyde having an ⁇ -active hydrogen atom due to its structural specificity, its own aldols under alkaline conditions
- the condensation reaction produces 2,2,4-trimethyl-3-hydroxyvaleraldehyde 0-hydroxyaldehyde:).
- the substance and isobutyraldehyde undergo an intermolecular redox reaction under alkaline conditions to form an ester compound monoisobutyrate (isobutyrate-3-hydroxy-2,2,3-trimethylpentyl ester) , saponification to form 2,2,4-trimethyl-1,3-pentanediol.
- Esterification reaction
- the compound of the invention belongs to a novel synthetic flavoring agent, has the advantages of simple synthetic route, no special equipment, easy availability of raw materials, no pollution of three wastes, and easy industrialization.
- the flavoring agent has the function of increasing the floral, fruity and woody notes in the cigarette, and can be used as a fragrance raw material for blending tobacco flavors, and can also be directly used in cigarettes. detailed description
- the homemade product and sodium hydroxide are arranged in a molar ratio of 1:1 into a mixed solution in the reaction bottle.
- the mixture is heated and stirred for several hours, and cooled, that is, the product crystallizes out, and the crystal obtained by filtration is washed with water to neutrality, dried, or purified by fractional distillation under reduced pressure to obtain 2,2,4-trimethyl-1,3- Pentylene glycol.
- Synthesis of glycol dicarboxylate will give 2,2,4-trimethyl-1,3-pentanediol to formic acid and sulfuric acid in a molar ratio of 1:4: 0.02 to the reaction flask, at 50- 52. Under C, the reaction was carried out for three hours.
- 2,2,4-Trimethyl-1,3-pentanediol dicarboxylate and dimethyl carbonate are subjected to transesterification to form a cyclic carbonate under the action of sodium alkoxide (molar ratio 1: 1.7: 0.1). Proportionally put the raw materials into the reaction flask, stir and heat the reaction until the methyl formate free.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Manufacture Of Tobacco Products (AREA)
Abstract
An organic compound and preparation method thereof, particularly a flavor enhancer and preparation method thereof, are disclosed. Its chemical name is 4-isopropyl-5,5-dimethyl-m-dioxan-2-one. It is prepared by the following method: starting from isobutyraldehyde, obtaining intermediate 2,2,4-thimethyl-1,3-pentanediol via self-aldol reaction of isobutyraldehyde, esterifying with formic acid to obtain 2,2,4-trimethyl-1,3-pentanediol bisformate, then transesterifying with dimethyl carbonate to obtain 4-isopropyl-5,5-dimethyl-m-dioxan-2-one. It is useful for enhancing the flavors of foodstuff, soap, toothpaste, cosmetic, cigarette, detergent and the like, such that the flavors could be more satisfied.
Description
一种增香剂及其制备方法 Flavoring agent and preparation method thereof
技术领域 Technical field
本发明涉及一种有机化合物及其制备方法， 具体地说是一种增香剂 及其制备方法。 The present invention relates to an organic compound and a process for the preparation thereof, and more particularly to a flavoring agent and a process for the preparation thereof.
背景技术 卷烟产品作为一种特殊的消费品， 烟用香精香料的应用被视为卷烟 产品的关键技术之一。 在打开烟盒时能发出芬芳馥郁的烟香， 在抽吸时 可产生津醇的吸味与香气， 其香味往往会成为消费者的吸食习惯， 也成 为引导消费习惯的主导因素之一， 而且加料加香也能改善和掩饰不同烟 叶而带来的不良吸味和气息， 保持卷烟产品风格的稳定。 因此， 烟用香 精香料的研究成为卷烟企业的核心技术， 也是卷烟企业吸引和引导消费 者的主要手段。 烟用香料主要来源于自然界和人工化学合成， 一般分为 天然香料和合成香料。 其中合成香料是指通过人工合成得到的香料化合 物， 按其官能团可分为醇类、 醚类、 醛类、 酮类、 酯类、 酸类和杂环类 等。 这些物质根据其对卷烟功能的不同可分类为甜味剂、 增香剂、 酸味 剂、 保润剂、 助燃剂和防腐剂等。 其中增香剂具有增强和增加烟草制品 的香味、 掩盖杂气， 常用来补偿烟香， 特别是在低焦油卷烟中应用更广 泛。 现有的增香剂品种很少， 一般使用香苴素作为增香剂， 因此香气比 较单一， 不能够满足不同消费者的需求。
发明内容 本发明的目的就是提供一种 4-异丙基 -5,5-二甲基-间-二氧六环 -2-酮 化合物， 它具有类似香苴素样及烟草样的气息， 可用于食品、 香皂、 牙 膏、 化妆品、 烟制品及洗涤剂等多种物质的加香， 从而使这种加香产品 的香气更加温和怡人。 本发明的另一目的就是提供该化合物的制备方法。 本发明的化学名称为 4-异丙基 -5,5-二甲基-间-二氧六环 -2-酮 （俗名， 环碳酸酯）， 它具有如下结构： BACKGROUND OF THE INVENTION Cigarette products are a special consumer product, and the application of flavors and fragrances for cigarettes is regarded as one of the key technologies of cigarette products. When the cigarette case is opened, it can emit a fragrant and fragrant scent. When it is pumped, it can produce the odor and aroma of the mellow alcohol. The scent tends to become a smoking habit of the consumer, and it is also one of the leading factors guiding the consumption habit, and Adding flavor and flavor can also improve and conceal the bad taste and atmosphere brought by different tobacco leaves, and maintain the stable style of cigarette products. Therefore, the research on tobacco flavors and fragrances has become the core technology of cigarette enterprises, and it is also the main means for cigarette companies to attract and guide consumers. Tobacco flavors are mainly derived from natural and artificial chemical synthesis, and are generally classified into natural flavors and synthetic flavors. The synthetic perfume refers to a perfume compound obtained by artificial synthesis, and can be classified into alcohols, ethers, aldehydes, ketones, esters, acids, and heterocyclics according to the functional groups thereof. These materials can be classified into sweeteners, flavoring agents, sour agents, humectants, oxidizers, preservatives, and the like, depending on their function on the cigarette. Among them, flavoring agents have the advantages of enhancing and increasing the aroma of tobacco products, masking the gas, and often used to compensate the smoke, especially in low-tar cigarettes. There are few varieties of flavoring agents available, and citronin is generally used as a flavoring agent, so the aroma is relatively simple and cannot meet the needs of different consumers. SUMMARY OF THE INVENTION The object of the present invention is to provide a 4-isopropyl-5,5-dimethyl-m-dioxan-2-one compound which has a scent-like and tobacco-like scent and is available. The aroma of food, soap, toothpaste, cosmetics, smoking products and detergents makes the aroma of this flavored product more gentle and pleasant. Another object of the invention is to provide a process for the preparation of this compound. The chemical name of the present invention is 4-isopropyl-5,5-dimethyl-m-dioxan-2-one (common name, cyclic carbonate), which has the following structure:
环碳酸酯具有类似香苴素样及烟草样的气息， 它的用途非常广泛， 可 用于食品， 香皂、 牙膏、 化妆品、 烟制品及洗涤剂等多种物质的加香， 从而使这种加香产品的香气更加温和怡人。 本发明以异丁醛为起始原料， 经醇醛缩合、 酯化反应合成环碳酸酯， 该产品在食品、 烟制品等中可增强其香气及香味， 并赋以该产品香豆素
间体 2,2,4-三甲基 -1,3-戊二醇，再经与甲酸的酯化反应得 2,2,4-三甲基 -1,3- 戊二醇二甲酸酯， 最后与碳酸二甲酯经酯交换反应而得最终产品环碳酸 The cyclic carbonate has a scent-like and tobacco-like scent. It is widely used for flavoring foods, soaps, toothpastes, cosmetics, smoking products and detergents. The aroma of the product is milder and more pleasant. The invention uses isobutyraldehyde as a starting material to synthesize a cyclic carbonate by aldol condensation and esterification reaction, and the product can enhance the aroma and aroma thereof in foods, smoking articles, etc., and the coumarin is given to the product. 2,2,4-trimethyl-1,3-pentanediol, which is then esterified with formic acid to give 2,2,4-trimethyl-1,3-pentanediol dicarboxylate Finally, transesterification reaction with dimethyl carbonate gives the final product ring carbonic acid
异 Τ1-3-ϋ·¾3-三甲 S¾ ¾4三甲基 -1,3-J£T1 具有一个 α活泼氢原子的异丁醛由于其结构上的特殊性， 在碱性条 件下发生自身醇醛缩合反应生成 2,2,4-三甲基 -3-羟基戊醛 0 -羟基醛：)。 该 物质和异丁醛在碱性条件下发生分子间的氧化还原反应， 而生成酯类化 合物单异丁酸酯 （异丁酸 -3-羟基 -2,2,3-三甲基戊酯）， 经皂化生成 2,2,4-三甲基 -1,3-戊二醇。 酯化反应 Isoindole 1-3-ϋ·3⁄43-triple S3⁄4 3⁄44 trimethyl-1,3-J£T1 isobutyraldehyde having an α-active hydrogen atom due to its structural specificity, its own aldols under alkaline conditions The condensation reaction produces 2,2,4-trimethyl-3-hydroxyvaleraldehyde 0-hydroxyaldehyde:). The substance and isobutyraldehyde undergo an intermolecular redox reaction under alkaline conditions to form an ester compound monoisobutyrate (isobutyrate-3-hydroxy-2,2,3-trimethylpentyl ester) , saponification to form 2,2,4-trimethyl-1,3-pentanediol. Esterification reaction
斗 2 0
Bucket 2 0
¾4三甲基 -l,3-l ¾二甲國
本发明的酯化反应过程中加入了苯或环己垸作为稳定剂， 这样反应 体系很稳定。 酯交换反应 3⁄44 trimethyl-l,3-l 3⁄4 dimethyl country In the esterification reaction of the present invention, benzene or cyclohexane is added as a stabilizer, so that the reaction system is stable. Transesterification
+ 2 H—— C + 2 H——C
oca 甲酸甲 g
Oca formic acid
本发明化合物属于一种新型合成增香剂， 具有合成工艺路线简单可 行、 无特殊设备、 原料易得、 基本无三废污染、 易于工业化。 该增香剂 具有增加卷烟中花香、 果香、 木香香韵的作用， 可作为调配烟用香精的 香原料， 亦可直接用于卷烟中。 具体实施方式 The compound of the invention belongs to a novel synthetic flavoring agent, has the advantages of simple synthetic route, no special equipment, easy availability of raw materials, no pollution of three wastes, and easy industrialization. The flavoring agent has the function of increasing the floral, fruity and woody notes in the cigarette, and can be used as a fragrance raw material for blending tobacco flavors, and can also be directly used in cigarettes. detailed description
2,2,4-三甲基 -1,3-戊二醇的合成 首先由异丁醛合成单异丁酸酯， 将异丁醛和氢氧化钠按照摩尔比 1 : 0.1配置成混合溶液， 于反应瓶中， 加热搅拌回流 2-3小时， 油层用饱和 盐水洗至中性， 油层减压蒸馏收集成品， 单异丁酸酯和二元醇， 即异丁 酸 -3-羟基 -2,2,3-3甲基戊酸和 2,2,4-三甲基 -1,3-戊二醇。再经过单酯皂化， 将自制的成品和氢氧化钠按照摩尔比 1 : 1配置成混合溶液，于反应瓶中
加热搅拌回流数小时， 冷却， 即有产物结晶析出， 过滤所得的晶体用水 洗至中性， 晾干，亦可用减压分馏提纯， 即得到 2,2,4-三甲基 -1,3-戊二醇。 二元醇二甲酸酯的合成 将得到 2,2,4-三甲基 -1,3-戊二醇与甲酸和硫酸按照摩尔比为 1： 4: 0.02 加到反应瓶中， 在 50-52。C下， 反应三小时。 采用经典的酯化法， 将适 量的苯或环己垸投入反应瓶， 搅拌下依次加入上述原料， 回流脱水至水 脱尽， 油层用饱和盐水洗至中性， 常压回收溶剂， 减压分馏得成品 — 2,2,4-三甲基 -1,3-戊二醇二甲酸酯， 无色透明液体， 带微弱的果香。 环碳酸酯的合成 Synthesis of 2,2,4-trimethyl-1,3-pentanediol First, monoisobutyrate was synthesized from isobutyraldehyde, and isobutyraldehyde and sodium hydroxide were mixed into a mixed solution at a molar ratio of 1:0.1. In the reaction flask, the mixture was heated and stirred for 2-3 hours, the oil layer was washed with saturated brine to neutrality, and the oil layer was distilled under reduced pressure to collect the finished product, monoisobutyrate and diol, ie, isobutyric acid-3-hydroxy-2. 2,3-3 methylvaleric acid and 2,2,4-trimethyl-1,3-pentanediol. After saponification of the monoester, the homemade product and sodium hydroxide are arranged in a molar ratio of 1:1 into a mixed solution in the reaction bottle. The mixture is heated and stirred for several hours, and cooled, that is, the product crystallizes out, and the crystal obtained by filtration is washed with water to neutrality, dried, or purified by fractional distillation under reduced pressure to obtain 2,2,4-trimethyl-1,3- Pentylene glycol. Synthesis of glycol dicarboxylate will give 2,2,4-trimethyl-1,3-pentanediol to formic acid and sulfuric acid in a molar ratio of 1:4: 0.02 to the reaction flask, at 50- 52. Under C, the reaction was carried out for three hours. Using the classical esterification method, an appropriate amount of benzene or cyclohexanil is put into the reaction flask, and the above raw materials are sequentially added under stirring, and the mixture is refluxed and dehydrated until the water is depleted. The oil layer is washed with saturated brine to neutrality, the solvent is recovered under normal pressure, and the solvent is distilled under reduced pressure. The finished product - 2,2,4-trimethyl-1,3-pentanediol dicarboxylate, a colorless, transparent liquid with a weak fruity aroma. Synthesis of cyclic carbonate
2,2,4-三甲基 -1,3-戊二醇二甲酸酯与碳酸二甲酯在醇钠 （摩尔比 1 : 1.7： 0.1 ) 作用下， 经酯交换反应生成环碳酸酯。 按比例将原料投入反应 瓶， 搅拌加热反应至无甲酸甲酯蒸出， 反应结束， 加入适量水， 分出水 层， 水层用少量环己垸萃取， 与油层合并， 用饱和盐水洗至中性， 常压 回收环己垸后， 减压分馏， 得无色透明液体， 略带微弱的木香、 香苴素 样、 烟草样的香气， 即得 4-异丙基 -5,5-二甲基-间-二氧六环 -2-酮。 应用实例 将所得的 4-异丙基 -5,5-二甲基-间-二氧六环 -2-酮样品按照 0.005% 加 到样品烟中， 请专门评吸人员按国家对卷烟的标准评吸方法和标准进行 评吸， 结果如下表 1。 经评吸， 样品烟丝较空白烟丝明显丰富烟香， 烟气 顺畅柔和， 杂气稍减， 口腔干净， 余味较舒适。 总体评价要优于后者。
表 1 : 加入环碳酸酯的烟丝（样品烟丝）与未加任何香料的烟丝（空白烟 丝） 的评吸结果比较 2,2,4-Trimethyl-1,3-pentanediol dicarboxylate and dimethyl carbonate are subjected to transesterification to form a cyclic carbonate under the action of sodium alkoxide (molar ratio 1: 1.7: 0.1). Proportionally put the raw materials into the reaction flask, stir and heat the reaction until the methyl formate free. After the reaction is finished, add appropriate amount of water, separate the aqueous layer, extract the aqueous layer with a small amount of cyclohexane, combine with the oil layer, wash with neutral saline to neutral After recovering the cyclohexane from atmospheric pressure, it is fractionated under reduced pressure to obtain a colorless transparent liquid with a slight woody, citron-like, tobacco-like aroma, which gives 4-isopropyl-5,5-dimethyl Base-m-dioxan-2-one. Application examples The sample of 4-isopropyl-5,5-dimethyl-m-dioxan-2-one obtained was added to the sample smoke according to 0.005%. Please refer to the national standard for cigarettes. The smoking method and standards were evaluated and the results are shown in Table 1. After sucking, the sample tobacco is obviously richer in smoke than the blank tobacco, the smoke is smooth and soft, the gas is slightly reduced, the mouth is clean, and the aftertaste is more comfortable. The overall evaluation is better than the latter. Table 1: Comparison of the smoking results of cut tobacco (sample cut tobacco) and cut tobacco without adding any flavor (white tobacco)
提取工艺 光泽 香 气 协调 杂 气 刺激性 余 味 Extraction process gloss aroma coordination miscellaneous gas irritation residual
5 32 6 12 20 25 计 空白烟丝 4 27.5 5 10 18 22 86.5 样品烟丝 4 28.5 5.5 10.5 18 23 89.5
5 32 6 12 20 25 Meter Blank tobacco 4 27.5 5 10 18 22 86.5 Sample cut tobacco 4 28.5 5.5 10.5 18 23 89.5
Claims
1. 一种增香剂， 它的化学名称为： 4-异丙基 -5,5-二甲基-间- -2-酮， 其具有如下结构： A flavoring agent having the chemical name: 4-isopropyl-5,5-dimethyl-m--2-one having the following structure:
2. 4-异丙基 -5,5-二甲基-间-二氧六环 -2-酮的制备方法， 它是以异丁醛 为起始原料， 经自身醇醛缩合反应得到中间体 2,2,4-三甲基 -1,3-戊二醇， 再经与甲酸进行酯化反应得 2,2,4-三甲基 -1,3-戊二醇二甲酸酯， 最后与碳 酸二甲酯经酯交换反应而得 4-异丙基 -5,5-二甲基-间-二氧六环 -2-酮。 2. A method for preparing 4-isopropyl-5,5-dimethyl-m-dioxan-2-one, which is obtained by using isobutyraldehyde as a starting material and obtaining an intermediate by its own aldol condensation reaction 2,2,4-trimethyl-1,3-pentanediol, which is then esterified with formic acid to give 2,2,4-trimethyl-1,3-pentanediol dicarboxylate, and finally The transesterification reaction with dimethyl carbonate gives 4-isopropyl-5,5-dimethyl-m-dioxan-2-one.
3. 根据权利要求 2所述的 4-异丙基 -5,5-二甲基-间-二氧六环 -2-酮的制 备方法， 所述的醇醛缩合反应的反应式如下： The method for producing 4-isopropyl-5,5-dimethyl-m-dioxan-2-one according to claim 2, wherein the reaction formula of the aldol condensation reaction is as follows:
异 Tl-:J-g¾^,3-三甲 ¾ 三甲基 -1，3-JT¾
Identical Tl-:J-g3⁄4^,3-trimethyl 3⁄4 trimethyl-1,3-JT3⁄4
4. 根据权利要求 2所述的 4-异丙基 -5,5- 备方法， 所述的酯化反应的反应式如下: 4. The 4-isopropyl-5,5-method according to claim 2, wherein the esterification reaction has the following reaction formula:
三甲基 二甲隨 Trimethyl dimethyl
；. 根据权利要求 2所述的 4-异丙基 -5,; 4-isopropyl-5 according to claim 2,
5- 备方法， 所述的酯交换反应的反应式如下: 5- Preparation method, the reaction formula of the transesterification reaction is as follows:
糊 Paste
6. 根据权利要求 2或 4所述的 4-异丙基 -5,5-二甲基-间-二氧六环 -2- 的制备方法， 所述的酯化反应过程中加入了苯或环己垸作为稳定剂。
The method for preparing 4-isopropyl-5,5-dimethyl-m-dioxane-2- according to claim 2 or 4, wherein benzene or benzene is added during the esterification reaction Cyclohexanide acts as a stabilizer.
7. 根据权利要求 2或 5所述的 4-异丙基 -5,5-二甲基-间-二氧六环 -2-酮 的制备方法， 所述的酯交换反应中加入了醇钠作为催化剂。 The method for preparing 4-isopropyl-5,5-dimethyl-m-dioxan-2-one according to claim 2 or 5, wherein sodium transester is added to the transesterification reaction As a catalyst.
8. 根据权利要求 2或 5所述的 4-异丙基 -5,5-二甲基-间-二氧六环 -2-酮 的制备方法， 所述的酯交换反应中二甲酸酯、 碳酸二甲酯和醇钠的摩尔 比为 1: 1.7: 0.1。
The method for producing 4-isopropyl-5,5-dimethyl-m-dioxan-2-one according to claim 2 or 5, wherein the diester ester in the transesterification reaction The molar ratio of dimethyl carbonate to sodium alkoxide is 1:1.7:0.1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810048354.8 | 2008-07-10 | ||
| CN200810048354A CN101624389A (en) | 2008-07-10 | 2008-07-10 | Flavoring agent and method for preparing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2010003299A1 true WO2010003299A1 (en) | 2010-01-14 |
Family
ID=41506659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CN2008/073427 WO2010003299A1 (en) | 2008-07-10 | 2008-12-10 | A flavor enhancer and preparation method thereof |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN101624389A (en) |
| WO (1) | WO2010003299A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107954871A (en) * | 2017-10-27 | 2018-04-24 | 江门谦信化工发展有限公司 | The preparation method of one kind 2,2,4- trimethyl -1,3- pentanediol mono isobutyrates |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101851226A (en) * | 2010-02-26 | 2010-10-06 | 湖北中烟工业有限责任公司 | Synthesis method and application of methyl4-isobutyl-5-methyl-5-ethyl-m-dioxane-2-one |
| CN103637398B (en) * | 2013-12-06 | 2015-07-01 | 川渝中烟工业有限责任公司 | Application method of compound 3,3',4',5,7-pentahydroxyflavone-3-rue glucoside |
| CN105132168A (en) * | 2015-08-18 | 2015-12-09 | 湖北中烟工业有限责任公司 | Preparation method of carbonyl compound-containing tobacco essence |
| CN106008157B (en) * | 2016-06-12 | 2019-07-02 | 江门谦信化工发展有限公司 | A kind of preparation method of 2,2,4- trimethyl -1,3- pentanediol diisobutyrate |
| CN111978178B (en) * | 2020-07-24 | 2023-03-28 | 润泰化学（泰兴）有限公司 | Preparation method of auxiliary film forming agent, film forming composition and preparation method of film forming composition |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4402985A (en) * | 1981-12-10 | 1983-09-06 | International Flavors & Fragrances Inc. | Flavoring with cyclic carbonate |
| WO2003089424A1 (en) * | 2002-04-16 | 2003-10-30 | Huntsman Petrochemical Corporation | 6-membered cyclic carbonates |
-
2008
- 2008-07-10 CN CN200810048354A patent/CN101624389A/en active Pending
- 2008-12-10 WO PCT/CN2008/073427 patent/WO2010003299A1/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4402985A (en) * | 1981-12-10 | 1983-09-06 | International Flavors & Fragrances Inc. | Flavoring with cyclic carbonate |
| WO2003089424A1 (en) * | 2002-04-16 | 2003-10-30 | Huntsman Petrochemical Corporation | 6-membered cyclic carbonates |
Non-Patent Citations (3)
| Title |
|---|
| LI, CHUN QIU: "Synthesis of cyclic carbonate", GUANGDONG CHEMICAL INDUSTRY, no. 2, 1986, pages 28 - 30 * |
| LIU, SA ET AL.: "Synthesis and application on foodstuff of 2,2,4-trimethyl-1,3-pentanediol", SCIENCE & TECHNOLOGY IN CHEMICAL INDUSTRY, vol. 9, no. 5, 2001, pages 27 - 29 * |
| SONG, XIAO RUI ET AL.: "Synthesis of 4-isopropyl-5,5-dimethyl-dioxan-one", MODERN CHEMICAL INDUSTRY, vol. 19, no. 2, 1999, pages 32 - 33 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107954871A (en) * | 2017-10-27 | 2018-04-24 | 江门谦信化工发展有限公司 | The preparation method of one kind 2,2,4- trimethyl -1,3- pentanediol mono isobutyrates |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101624389A (en) | 2010-01-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2010003299A1 (en) | A flavor enhancer and preparation method thereof | |
| US3879466A (en) | Bicyclo-{8 2.2.2{9 octa-5,7-dien-2-ones and a process for their preparation | |
| CN101589034B (en) | Pyran derivatives, process of preparation and use thereof in perfumery and flavouring | |
| CN102884034B (en) | Compounds with a woody note | |
| CN101589021A (en) | Use of campholenic derivatives as fragrant ingredients in perfumery and flavouring | |
| JP2002512609A (en) | Method for producing aromatic aldehyde | |
| CA1062904A (en) | Flavoring and fragrance compositions containing alpha-substituted acetaldehyde taken alone or taken together with ketone and methods for imparting, altering, modifying or enhancing the organoleptic properties of consumable materials using same | |
| JP6476475B2 (en) | Flavor and aroma mixture (I) | |
| CA1044700A (en) | Bicyclic fragrance materials and processes therefor | |
| EP2125767A2 (en) | Pyran derivatives, process of preparation and use thereof in perfumery and flavouring | |
| US4318934A (en) | Flavoring with branched chain olefinic alcohols | |
| JP4102412B2 (en) | Alcohol compounds | |
| EP0007486B1 (en) | Oxygenated compounds derived from tricyclo(6.2.1.0)undecane, their utilization as perfumes or fragrances, and compositions containing these compounds | |
| US4041084A (en) | Tricyclic alcohols | |
| US4031140A (en) | 4- AND 5-Phenyl pentenal acetals | |
| US3988487A (en) | Foodstuff flavoring compositions comprising alkylidene alkenals and processes for preparing same as well as flavoring compositions for use in such foodstuff | |
| JP2011037761A (en) | Aliphatic esters, perfume composition containing the compound and method for producing the compound | |
| US4036886A (en) | Processes for producing 4- and 5-phenyl pentenals | |
| US4157350A (en) | Process for preparing 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1,3-butanedione and intermediates | |
| CN104024202A (en) | Novel cycloalkane aldehydes, methods for preparing same, and use thereof in the perfume industry | |
| CA1058442A (en) | Flavoring and fragrance compositions and products | |
| US4399062A (en) | Branched chain olefinic alcohols, thiols, esters and ethers, organoleptic uses thereof, processes for preparing same and intermediates therefor | |
| JP3838714B2 (en) | Methyl (E) -4,7-octadienoate and process for producing the same | |
| US4021494A (en) | Process for preparing tricyclic alcohols | |
| CN101851226A (en) | Synthesis method and application of methyl4-isobutyl-5-methyl-5-ethyl-m-dioxane-2-one |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 08876541 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 08876541 Country of ref document: EP Kind code of ref document: A1 |