CN102603528A - Method for preparing n-amyl cinnamate by transesterification reaction catalyzed by ionic liquid - Google Patents
Method for preparing n-amyl cinnamate by transesterification reaction catalyzed by ionic liquid Download PDFInfo
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Abstract
The invention belongs to the technical field of chemistry and chemical engineering, and discloses a method for preparing n-amyl cinnamate by a transesterification reaction catalyzed by ionic liquid. The method comprises the following steps of: mixing methyl cinnamate, 1-butyl-3-methylimidazole p-toluenesulfonate 14-16% of the weight of methyl cinnamate, and n-amyl alcohol evenly, performing radiation with 100-500W microwave for 5-60 min at a set temperature of 90-137 DEG C, and carrying out separation to obtain n-amyl cinnamate, wherein the conversion rate of methyl cinnamate reaches 29.45%. The method provided by the invention adopts a novel technique of a microwave assisted transesterification reaction catalyzed by 1-butyl-3-methylimidazole p-toluenesulfonate ionic liquid to synthesize n-amyl cinnamate, and the method has the advantages of high heating efficiency, greatly shortened reaction time, low energy consumption, high efficiency, simple process, easiness in post treatment, recyclable catalyst, environmental friendliness and the like. The method is consistent with the concept of sustainable development, is an environment-friendly energy-saving green chemical method, and has a good industrialization prospect.
Description
Technical field
The invention belongs to technical field of chemistry and chemical engineering; Relate to the method that a kind of ionic liquid-catalyzed transesterification reaction prepares Pentyl cinnamate, particularly a kind of microwave cooperating 1-butyl-ionic liquid-catalyzed methyl cinnamate of 3-Methylimidazole tosilate and Pentyl alcohol transesterification reaction prepare the method for Pentyl cinnamate.
Background technology
Laurate is one type of important synthetic perfume, is widely used in because of peat-reek in the batching of food flavour and daily chemical essence with fruit or fragrance of a flower, and also be important organic synthesis raw material simultaneously.Pentyl cinnamate is a kind of fragrant ester with cocoa aroma, in industry, is widely used in allotment edible and daily chemical essence.
The compound method of laurate is mainly the conventional heating of traditional strong acid catalysis esterification synthesis method at present; Promptly by styracin and alcohol esterification taking place prepares; Adopt conventional type of heating to make this method have long reaction time, side reaction is many, productive rate low with shortcoming such as production cost height.
Simultaneously; The catalyzer of this compound method can be sulfuric acid, hydrochloric acid etc.; But such catalyzer exists catalyzer that equipment corrosion is seriously reached the pollution problem of waste liquid, and when using the vitriol oil simultaneously, regular meeting makes the side reactions such as alcohol generation intramolecularly and intermolecular dehydration in the reactant after its consumption surpasses certain value; Cause product yield to descend color burn.And separable solid acid catalyst just under study for action, comprises tosic acid, strongly acidic cationic exchange resin, ferric chloride (FeCl36H2O) and heteropolyacid etc., (Yang Shuijin, Yu Xieqing, Liang Yongguang, TiSiW such as Yang Shuijin
12O
40/ TiO
2Catalysis synthesizing cinnamic acid n-pentyl ester, chemical science and technology, 2002,10 (1): 8-10) adopt with solid-carrying heteropolyacid salt TiSiW
12O
40/ TiO
2Esterification for heterogeneous catalyst catalysis styracin and Pentyl alcohol; Investigated the influence to reaction result such as molar ratio of alcohol to acid, reaction times, temperature of reaction, catalyst levels, but there are the deficiencies such as separation and purification complicated operation of complex equipments, long reaction time and product in this reaction process.
Transesterification reaction is important organic synthesis, is widely used in medicine and synthesizes fields such as reaching organic chemistry, and also be the important method of synthesizing ester.And the microwave-assisted organic synthesis is the novel green synthesis method of development in recent years; It is the research focus of at present domestic and international organic synthesis; Ionic-liquid catalyst then is to have non-corrosiveness, nontoxic, novel environmentally friendly solvent and the liquid catalyst that are difficult for advantages such as oxidation, catalytic activity are high, product is easily separated, is programmable green catalyst and solvent.At present, no-trump microwave control still and ionic-liquid catalyst are used for system's correlative study of ester-exchange reaction jointly.
Summary of the invention
In order to solve the weak point that exists in the above-mentioned existing laurate synthetic technology; Primary and foremost purpose of the present invention is to provide a kind of ionic liquid-catalyzed transesterification reaction to prepare the method for Pentyl cinnamate, is the method that a kind of microwave cooperating 1-butyl-ionic liquid-catalyzed methyl cinnamate of 3-Methylimidazole tosilate and Pentyl alcohol transesterification reaction prepare Pentyl cinnamate.
The object of the invention is realized through following technical proposals:
A kind of ionic liquid-catalyzed transesterification reaction prepares the method for Pentyl cinnamate, comprises following operation steps:
In the microwave reaction jar, add methyl cinnamate, catalyzer 1-butyl-3-Methylimidazole tosilate and Pentyl alcohol, fully mixing obtains reaction raw materials; The mol ratio of said methyl cinnamate and Pentyl alcohol is 1: 6～1: 12; Reaction raw materials is carried out microwave exposure 5～60min, and microwave power is set at 100～500W, and the microwave exposure temperature is set at 90～137 ℃, and the microwave exposure after product obtains Pentyl cinnamate after separating.
In order to realize the present invention better, the consumption of said 1-butyl-3-Methylimidazole tosilate is 14～16% of a methyl cinnamate quality; The consumption of said 1-butyl-3-Methylimidazole tosilate is preferably 16% of methyl cinnamate quality.
The mol ratio of said methyl cinnamate and Pentyl alcohol is preferably 1: 8.
The time of said microwave exposure is preferably 30min.
Said microwave power is preferably 400W.
Said microwave exposure temperature is preferably 110 ℃.
Principle of the present invention is:
Ionic liquid is meant the liquid of under room temperature or nearly room temperature, being made up of the yin, yang ion fully, generally by specific, that volume is relatively large, that the asymmetric organic cation of structure and the less relatively organic or inorganic negatively charged ion of volume are formed one type of organic salt.Ionic liquid is a kind of novel environmentally friendly solvent and liquid catalyst; Ionic liquid self as reaction medium has particular performances; Not only can catalyse organic reaction; And in organic synthesis and separation and purification the instead organic solvent; It has as solvent that steam forces down and advantage such as not volatile; Have the high-density reactive behavior site of the non-volatility and the liquid acid of solid acid simultaneously as catalyzer, have non-corrosiveness, nontoxic, be difficult for that oxidation, liquid wide ranges, soluble end are wide, good stability, catalytic activity is high, product is easily separated and a series of peculiar properties such as reusable edible, has been widely used in fields such as chemosynthesis, separation engineering and nano material preparation.The difference of ionic liquid and traditional solvent and catalyzer is that mainly its acid and solvability etc. can regulate through the structure of change zwitterion; So ionic liquid is programmable green catalyst and solvent, bring hope for solving difficult problems such as traditional chemical reaction high pollution, low-yield and difficult separates.
Based on this; The present invention adopts the transesterification reaction of microwave cooperating 1-butyl-ionic liquid-catalyzed methyl cinnamate of 3-Methylimidazole tosilate and Pentyl alcohol to prepare Pentyl cinnamate, have the reaction times short, energy consumption is low, process is simple, aftertreatment is easy, catalyzer reusable edible and environment amenable characteristics.
The present invention compares with prior art, has following advantage and beneficial effect:
Ionic liquid is as the rare trial in transesterification reaction of catalyzer synthesis of organic substance at present; The present invention utilizes microwave-ionic liquid concerted catalysis transesterification reaction; Merged the advantage of ionic liquid and microwave heating technique, this method has following good characteristic in organic synthesis:
(1) ionic liquid is the higher and organic salt that in room temperature range, is in a liquid state of boiling point; Even be heated to comparatively high temps; Stability in reaction system is still good, makes its applied range, for promoting that microwave method provides brand-new thinking in the application of high-temperature liquid-phase the field of chemical synthesis.
(2) in the transesterification reaction of microwave-ionic liquid concerted catalysis methyl cinnamate; 1-butyl-ion liquid consumption of 3-Methylimidazole tosilate is 14～16% of a methyl cinnamate quality; And 1-butyl-3-Methylimidazole tosilate is both as catalyst for reaction; Alternative partial solvent has reduced cost simultaneously; Improved the microwave absorbing efficient of reaction system as its strong polarity of ionic liquid of organic salt, accelerated speed of reaction, can effectively cut down the consumption of energy.
(3) easily separated, purifying and recovery; Because product ester class and ionic liquid polarity differ greatly; Can leave standstill AUTOMATIC ZONING; The solvent that also can select to be fit to extracts product, and crude product can get target product after refining, and reacted ionic liquid can at room temperature wash the regeneration of dry back with organic solvents such as ethers.
(4) easy to operate and safe, reaction conditions is realized easily, can adopt standard method of analysis quantification sign products such as LC-MS in the building-up process, and tracking reaction process and analytical reaction mechanism are for the research transesterification reaction provides approach effectively accurately.
In addition; The present invention adopts the novel process of the positive butyl ester of transesterification reaction synthesizing cinnamic acid of microwave cooperating 1-butyl-ionic liquid-catalyzed methyl cinnamate of 3-Methylimidazole tosilate and Pentyl alcohol; Has the heating efficiency height; Reaction times is short, energy consumption is low, process is simple, aftertreatment is easy, catalyzer reusable edible and characteristics such as environmentally friendly; Be one and meet the environment amenable energy-saving Green Chemistry novel method of Sustainable development, particularly face now under the increasingly serious energy starved situation and have more the good industrialized prospect in China.
Embodiment
Below in conjunction with embodiment the present invention is described in further detail, but embodiment of the present invention is not limited thereto.
The material that following examples adopted is:
Methyl cinnamate (two fragrant auxiliary reagent factories, Shanghai, purity is greater than 98%); Pentyl cinnamate standard substance (the big spices in Guangzhou company, purity is greater than 98%); 1-butyl-3-Methylimidazole tosilate ionic liquid (go up the prompt chemical ltd of marine origin, purity is greater than 99%); Other reagent are analytical pure (Guangzhou Chemical Reagent Factory).
The instrument that following examples adopted is:
WF-4000 normal pressure microwave quick-reaction system (Shanghai stand erect Yao's instrumental analysis ltd); WAY-1 type Abbe refractometer (optical instrument factory, Shanghai), SHIMADZU-LC-MS-2010A type electrospray mass spectrometer (day island proper Tianjin instrument company), Agilent 7890A-5975C GC-MS type gas chromatography-mass spectrometry chromatogram appearance (hewlette-packard).
Embodiment 1
(down together) adding 1.6219g (0.01mol) methyl cinnamate and 0.2595g 1-butyl-3-Methylimidazole tosilate in the microwave reaction jar of WF-4000 normal pressure microwave quick-reaction system; Add the 0.1mol Pentyl alcohol again; Fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 45min, and microwave power is set at 200W, and the microwave exposure temperature is set at 137 ℃, obtains colourless product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 27.43%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), consistent with literature value (Ding Liangzhong, Yu Shanxin, Wen Ruiming. SE ferric trichloride catalytic catalytic Synthesis of Cinnamate [J]. University Of Shanxi's journal, 2001,24 (2): 133-135. is down together).
2, infared spectrum data: with the ir spectra of KBr liquid-film method mensuration product, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713; 1637,1578,1496,1310,1170; 979,864,767,710 and 684, with document (Ding Liangzhong; Yu Shanxin, Wen Ruiming. SE ferric trichloride catalytic catalytic Synthesis of Cinnamate [J]. University Of Shanxi's journal, 2001,24 (2): 133-135. down with) contrast shows that this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
Embodiment 2
In the microwave reaction jar, add 1.6219g (0.01mol) methyl cinnamate and 0.2595g 1-butyl-3-Methylimidazole tosilate, add the 0.1mol Pentyl alcohol again, fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 30min, and microwave power is set at 400W, and the microwave exposure temperature is set at 137 ℃, obtains faint yellow product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 29.45%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), and consistent with literature value.
2, infared spectrum data: with the ir spectra of KBr liquid-film method mensuration product, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713,1637,1578,1496,1310,1170,979,864,767,710 and 684, show that with the document contrast this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
Embodiment 3
In the microwave reaction jar, add 1.6219g (being 0.01mol) methyl cinnamate and 0.2271g 1-butyl-3-Methylimidazole tosilate, add the 0.08mol Pentyl alcohol again, fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 30min, and microwave power is set at 400W, and the microwave exposure temperature is set at 110 ℃, obtains faint yellow product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 19.72%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), and consistent with literature value.
2, infared spectrum data: with the ir spectra of KBr liquid-film method mensuration product, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713,1637,1578,1496,1310,1170,979,864,767,710 and 684, show that with the document contrast this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
Embodiment 4
In the microwave reaction jar, add 1.6219g (0.01mol) methyl cinnamate and 0.2595g 1-butyl-3-Methylimidazole tosilate, add the 0.1mol Pentyl alcohol again, fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 30min, and microwave power is set at 500W, and the microwave exposure temperature is set at 137 ℃, obtains faint yellow product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 25.62%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), and consistent with literature value.
2, infared spectrum data: with the ir spectra of KBr liquid-film method mensuration product, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713,1637,1578,1496,1310,1170,979,864,767,710 and 684, show that with the document contrast this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
Embodiment 5
In the microwave reaction jar, add 1.6219g (0.01mol) methyl cinnamate and 0.2595g 1-butyl-3-Methylimidazole tosilate, add the 0.1mol Pentyl alcohol again, fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 60min, and microwave power is set at 200W, and the microwave exposure temperature is set at 137 ℃, obtains colourless product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 26.77%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), and consistent with literature value.
2, infared spectrum data: measure the ir spectra of product respectively with the KBr liquid-film method, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713,1637,1578,1496,1310,1170,979,864,767,710 and 684, show that with the document contrast this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
Embodiment 6
In the microwave reaction jar, add 1.6219g (0.01mol) methyl cinnamate and 0.2595g 1-butyl-3-Methylimidazole tosilate, add the 0.1mol Pentyl alcohol again, fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 5min, and microwave power is set at 200W, and the microwave exposure temperature is set at 137 ℃, obtains colourless product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 8.27%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), and consistent with literature value.
2, infared spectrum data: with the ir spectra of KBr liquid-film method mensuration product, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713,1637,1578,1496,1310,1170,979,864,767,710 and 684, show that with the document contrast this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
Embodiment 7
In the microwave reaction jar, add 1.6219g (0.01mol) methyl cinnamate and 0.2595g 1-butyl-3-Methylimidazole tosilate, add the 0.06mol Pentyl alcohol again, fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 30min, and microwave power is set at 200W, and the microwave exposure temperature is set at 137 ℃, obtains faint yellow product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 21.04%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), and consistent with literature value.
2, infared spectrum data: with the ir spectra of KBr liquid-film method mensuration product, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713,1637,1578,1496,1310,1170,979,864,767,710 and 684, show that with the document contrast this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
Embodiment 8
In the microwave reaction jar, add 1.6219g (0.01mol) methyl cinnamate and 0.2595g 1-butyl-3-Methylimidazole tosilate, add the 0.08mol Pentyl alcohol again, fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 30min, and microwave power is set at 200W, and the microwave exposure temperature is set at 137 ℃, obtains faint yellow product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 28.21%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), and consistent with literature value.
2, infared spectrum data: with the ir spectra of KBr liquid-film method mensuration product, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713,1637,1578,1496,1310,1170,979,864,767,710 and 684, show that with the document contrast this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
Embodiment 9
In the microwave reaction jar, add 1.6219g (0.01mol) methyl cinnamate and 0.2595gl-butyl-3-Methylimidazole tosilate, add the 0.12mol Pentyl alcohol again, fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 30min, and microwave power is set at 200W, and the microwave exposure temperature is set at 137 ℃, obtains faint yellow product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 20.87%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), and consistent with literature value.
2, infared spectrum data: with the ir spectra of KBr liquid-film method mensuration product, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713,1637,1578,1496,1310,1170,979,864,767,710 and 684, show that with the document contrast this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
Embodiment 10
In the microwave reaction jar, add 1.6219g (0.01mol) methyl cinnamate and 0.2595g 1-butyl-3-Methylimidazole tosilate, add the 0.1mol Pentyl alcohol again, fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 30min, and microwave power is set at 200W, and the microwave exposure temperature is set at 137 ℃, obtains colourless product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 27.54%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), and consistent with literature value.
2, infared spectrum data: with the ir spectra of KBr liquid-film method mensuration product, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713,1637,1578,1496,1310,1170,979,864,767,710 and 684, show that with the document contrast this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
Embodiment 11
In the microwave reaction jar, add 1.6219g (0.01mol) methyl cinnamate and 0.2595g 1-butyl-3-Methylimidazole tosilate, add the 0.1mol Pentyl alcohol again, fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 30min, and microwave power is set at 200W, and the microwave exposure temperature is set at 90 ℃, obtains faint yellow product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 18.17%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), and consistent with literature value.
2, infared spectrum data: with the ir spectra of KBr liquid-film method mensuration product, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713,1637,1578,1496,1310,1170,979,864,767,710 and 684, show that with the document contrast this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
Embodiment 12
In the microwave reaction jar, add 1.6219g (being 0.01mol) methyl cinnamate and 0.2595g 1-butyl-3-Methylimidazole tosilate, add the 0.1mol Pentyl alcohol again, fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 30min, and microwave power is set at 200W, and the microwave exposure temperature is set at 110 ℃, obtains faint yellow product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 28.86%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), and consistent with literature value.
2, infared spectrum data: with the ir spectra of KBr liquid-film method mensuration product, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713,1637,1578,1496,1310,1170,979,864,767,710 and 684, show that with the document contrast this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
Embodiment 13
In the microwave reaction jar, add 1.6219g (0.01mol) methyl cinnamate and 0.2595g 1-butyl-3-Methylimidazole tosilate, add the 0.1mol Pentyl alcohol again, fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 30min, and microwave power is set at 100W, and the microwave exposure temperature is set at 137 ℃, obtains faint yellow product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 12.11%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), and consistent with literature value.
2, infared spectrum data: with the ir spectra of KBr liquid-film method mensuration product, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713,1637,1578,1496,1310,1170,979,864,767,710 and 684, show that with the document contrast this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
Embodiment 14
In the microwave reaction jar, add 1.6219g (0.01mol) methyl cinnamate and 0.2595g 1-butyl-3-Methylimidazole tosilate, add the 0.1mol Pentyl alcohol again, fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 30min, and microwave power is set at 300W, and the microwave exposure temperature is set at 137 ℃, obtains faint yellow product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 28.37%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), and consistent with literature value.
2, infared spectrum data: with the ir spectra of KBr liquid-film method mensuration product, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713,1637,1578,1496,1310,1170,979,864,767,710 and 684, show that with the document contrast this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
Embodiment 15
In the microwave reaction jar, add 1.6219g (being 0.01mol) methyl cinnamate and 0.2595g 1-butyl-3-Methylimidazole tosilate, add the 0.1mol Pentyl alcohol again, fully mixing obtains reaction raw materials; Reaction raw materials is carried out microwave exposure 30min, and microwave power is set at 200W, and the microwave exposure temperature is set at 120 ℃, obtains faint yellow product behind the microwave exposure.The utilization GC-MS carries out qualitative and quantitative analysis to carrying out products therefrom, and the transformation efficiency that calculates methyl cinnamate is 27.91%.
Products therefrom is carried out following mensuration:
1, the mensuration of physical constant: carry out index determination after product is purified, its refractive index is 1.5384 (30 ℃), and is consistent with the mensuration numerical value of standard substance; Boiling point is: 205-207 ℃ (2000Pa), and consistent with literature value.
2, infared spectrum data: with the ir spectra of KBr liquid-film method mensuration product, main absorption peak (cm
-1) as follows: 3062,3029,2956,2871,1713,1637,1578,1496,1310,1170,979,864,767,710 and 684, show that with the document contrast this product is a Pentyl cinnamate.
3, electrospray ionization mass spectrum: product is done electrospray ionization mass spectrum after being dissolved in anhydrous methanol, and main molecules quasi-molecular ions ownership is (M=218): m/e 218.9 [M+H] as follows
+, m/e 251 [M+CH
3OH+H]
+, explain that institute's synthetic product is the title product Pentyl cinnamate.
The foregoing description is a preferred implementation of the present invention; But embodiment of the present invention is not restricted to the described embodiments; Other any do not deviate from change, the modification done under spirit of the present invention and the principle, substitutes, combination, simplify; All should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (7)
1. an ionic liquid-catalyzed transesterification reaction prepares the method for Pentyl cinnamate, it is characterized in that comprising following operation steps:
In the microwave reaction jar, add methyl cinnamate, catalyzer 1-butyl-3-Methylimidazole tosilate and Pentyl alcohol, fully mixing obtains reaction raw materials; The mol ratio of said methyl cinnamate and Pentyl alcohol is 1: 6～1: 12; Reaction raw materials is carried out microwave exposure 5～60min, and microwave power is set at 100～500W, and the microwave exposure temperature is set at 90～137 ℃, and the microwave exposure after product obtains Pentyl cinnamate after separating.
2. a kind of catalysis methyl cinnamate transesterification reaction according to claim 1 prepares the method for Pentyl cinnamate, it is characterized in that: the quality of said 1-butyl-3-Methylimidazole tosilate is 14～16% of a methyl cinnamate quality.
3. a kind of ionic liquid-catalyzed transesterification reaction according to claim 2 prepares the method for Pentyl cinnamate, it is characterized in that: the quality of said 1-butyl-3-Methylimidazole tosilate is 16% of a methyl cinnamate quality.
4. a kind of ionic liquid-catalyzed transesterification reaction according to claim 1 prepares the method for Pentyl cinnamate, it is characterized in that: the mol ratio of said methyl cinnamate and propyl carbinol is 1: 8.
5. a kind of ionic liquid-catalyzed transesterification reaction according to claim 1 prepares the method for Pentyl cinnamate, it is characterized in that: the time of said microwave exposure is 30min.
6. a kind of ionic liquid-catalyzed transesterification reaction according to claim 1 prepares the method for Pentyl cinnamate, it is characterized in that: said microwave power is set at 400W.
7. a kind of ionic liquid-catalyzed transesterification reaction according to claim 1 prepares the method for Pentyl cinnamate, it is characterized in that: said microwave exposure temperature is set at 110 ℃.
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| CN111269115A (en) * | 2020-02-26 | 2020-06-12 | 陕西科技大学 | Preparation method of cinnamate in eutectic solvent |
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