CN1434016A - Method for producing perfume using ionol ester as raw material by thermo-wacking rectifying - Google Patents
Method for producing perfume using ionol ester as raw material by thermo-wacking rectifying Download PDFInfo
- Publication number
- CN1434016A CN1434016A CN03115146A CN03115146A CN1434016A CN 1434016 A CN1434016 A CN 1434016A CN 03115146 A CN03115146 A CN 03115146A CN 03115146 A CN03115146 A CN 03115146A CN 1434016 A CN1434016 A CN 1434016A
- Authority
- CN
- China
- Prior art keywords
- ionol
- raw material
- ester
- rectifying
- spices
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 ionol ester Chemical class 0.000 title claims abstract description 18
- 239000002994 raw material Substances 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 239000002304 perfume Substances 0.000 title abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000000926 separation method Methods 0.000 claims abstract description 6
- 238000009835 boiling Methods 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- PWDOJWCZWKWKSE-BQYQJAHWSA-N 4,7-Megastigmadien-9-ol Chemical group CC(O)\C=C\C1C(C)=CCCC1(C)C PWDOJWCZWKWKSE-BQYQJAHWSA-N 0.000 claims description 14
- PWDOJWCZWKWKSE-UHFFFAOYSA-N alpha-Ionol Natural products CC(O)C=CC1C(C)=CCCC1(C)C PWDOJWCZWKWKSE-UHFFFAOYSA-N 0.000 claims description 14
- 235000013599 spices Nutrition 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 13
- 238000010504 bond cleavage reaction Methods 0.000 claims description 9
- 230000007017 scission Effects 0.000 claims description 9
- 238000000066 reactive distillation Methods 0.000 claims description 8
- 235000019439 ethyl acetate Nutrition 0.000 claims description 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 229910001220 stainless steel Inorganic materials 0.000 claims description 2
- 239000010935 stainless steel Substances 0.000 claims description 2
- 229940070710 valerate Drugs 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004227 thermal cracking Methods 0.000 abstract description 3
- BWPHCNAZKLXPHW-RMKNXTFCSA-N 2-[(1e)-buta-1,3-dienyl]-1,3,3-trimethylcyclohexene Chemical compound CC1=C(\C=C\C=C)C(C)(C)CCC1 BWPHCNAZKLXPHW-RMKNXTFCSA-N 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 238000010183 spectrum analysis Methods 0.000 abstract 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 9
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 238000005336 cracking Methods 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 238000003556 assay Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
The present invention discloses a method for producing perfume using ionol ester as raw material through the processes of thermal cracking and rectification. Said invented method integrates the thermal cracking reaction and rectification separation into one body, makes the raw material undergo the processes of reaction and rectification to collect the fractions with different boiling ranges from tower top of the equipment so as to obtain the target products with different purities. The mass spectral analysis and chromatographic analysis show that the purity of the obtained megastigmatriene perfume is above 95%.
Description
Technical field
The present invention relates to a kind of production method of spices, particularly a kind of is the method for the edible or tobacco aromatics using of raw material production with the violet alcohol ester.
Background technology
The derivatization reaction of violet alcohol ester is a kind of important chemical reaction, with the violet alcohol ester is that raw material is sloughed ester group and can be made a series of important spices, at present, the derivatization reaction of known violet alcohol ester mainly contains two lines: a kind of is hydrolysis method, be United States Patent (USP) (U.S.3,211,157.U.S.3,268,589) disclosed; Another kind is the cracking of high temperature post, the rectifying extraction method, for United States Patent (USP) (U.S.4,753,924) disclosed.
Before a kind of method seem simply, but technology more complicated in fact, the production cycle is grown (time-consuming approximately tens of hours), condition is wayward, often is easy to generate a large amount of cyclisation by products, thereby has increased the aftertreatment difficulty.A kind of method in back need slowly drip raw material and react under the high temperature more than 400 ℃, not only treatment capacity is little, and energy consumption is big, and the product purity that generates is lower, and output is little, needs further to be purified by rectifier unit.
In a word, because existing is the existing shortcoming of method of raw material production spices with the violet alcohol ester, therefore branch of industry wishes that relevant engineering technical personnel are improved, provide that a kind of production is easy, the cycle is short, energy consumption is low, transformation efficiency is high and be easy to industrialized method, to promote the technical progress of perfume industry.
Summary of the invention
Purpose of the present invention is the above-mentioned shortcoming that overcomes prior art, providing a kind of is the method that spices is produced in the rectifying of raw material heat scission reaction with the violet alcohol ester, it has that production technique is simple, energy consumption is low, productive rate is high and advantage such as cost is few, helps large-scale industrial production and promotes the technical progress of perfume industry.
Design of the present invention is such:
The contriver finds that if can remove reaction product timely, then thermal cracking processes can carry out at a lower temperature fast in the ionol ester compound heat scission reaction process on the basis of being engaged in spices research preparation work for a long time.For this reason the contriver to have conceived a kind of be raw material with the violet alcohol ester, in a rectifier unit, thermo-cracking limit, limit rectifying separation product is produced the method for spices, in other words: this method is in rectifier unit, integrate scission reaction and rectifying separation, thereby reduce the scission reaction temperature greatly, accelerate speed of reaction, shorten the reaction times, and significantly improved the yield of target product.
The present invention also is achieved in that
Be provided with a stuffing rectification column on the still of heating unit outside one has, raw material places still to be heated gasification, enters limit cracking limit separation in the stuffing rectification column, from the overhead collection reaction product, regulates the reflux ratio of cat head, can obtain target product with high purity.In other words: the heat scission reaction of raw material and the rectifying separation of product are carried out in stuffing rectification column simultaneously.This method can periodical operation, also can operate continuously, and should keep the raw material of still into during operate continuously and go out material balance between the tower product.
Filler is the Stainless Steel Helices of different structure form in the said stuffing rectification column, as the Raschig ring type, and porous Raschig ring type, netted Raschig ring type, netted saddle-shape, a kind of in the spiral spring type or more than one.
The processing condition of heat scission reaction rectifying (hereinafter to be referred as reactive distillation) process are:
(1) reactive distillation processes carries out under high vacuum, the residual voltage (working pressure) in the adjustable device
Be 0.3～2.0Kpa, should under 0.3～1.0Kpa condition, operate;
(2) the rectifier unit temperature in the kettle is 80～160 ℃, and it is pressed with the difference and the interior operation of device of material
The difference of power and changing;
(3) the suitable first total reflux operation of device initial start stage is 1～2 hour, is 2～3 times in reflux ratio then
Operation;
(4) at the cut of 60～75 ℃ of overhead collection (overhead vapours temperature) boiling range scope, be this
Bright target product.
Said violet alcohol ester is α-ionol acetic ester, α-ionol propionic ester, α-ionol butyric ester, a kind of in α-ionol valerate, or their mixture.
Specific operation process is described below:
At first raw material violet alcohol ester is put into the tower still of reaction and rectification device, opening the vacuum apparatus vacuum pipeline of factory (or connect) is under the high vacuum state rectifier unit, then the tower still is carried out outer heating, residual voltage in the reaction and rectification device is 0.3～2.0Kpa, and temperature in the kettle is 80～160 ℃.2～3 times operations of reflux ratio are regulated in elder generation's total reflux operation 1～2 hour (should operate 1 hour) then, and the cut from 60～75 ℃ of boiling range scopes of overhead collection is target product.Products therefrom with look-matter combined instrument (be called for short GC-MS) and chromatographic instrument (being called for short GC) Analysis and Identification it.This method can periodical operation, also can operate continuously, should keep passing in and out the balance of tower material during operate continuously
Embodiment
Further set forth content of the present invention below in conjunction with embodiment, but these embodiment do not limit protection scope of the present invention.
Embodiment 1 α-ionol acetic ester is produced the huge beans triolefin of spices through reactive distillation:
(concentration is 85%wt to take by weighing 200g α-ionol acetic ester, all the other are other violet alcohol esters) and join in the rectifying still, install the rectification process device, vacuumize to make with vacuum pump and be in the rectifying tower under the high vacuum state, then the tower still is heated with oil bath.Residual voltage 0.3Kpa in the rectification process device, 90～130 ℃ of temperature in the kettle, elder generation's total reflux operation 1 hour, regulating reflux ratio then is 2.0, collect the cut of 60～66 ℃ (overhead vapours temperature), collected cut was huge beans triolefin after GC-MS and GC Analysis and Identification in 2 hours, content is 97%wt, and the yield of huge beans triolefin is 92%.
Embodiment 2 α-ionol acetic ester is through the huge beans triolefin of reactive distillation system spices:
(concentration is 85%wt to take by weighing 200g α-ionol acetic ester, all the other are other violet alcohol esters) and join in the rectifying still, install the rectification process device, vacuumize to make with vacuum pump and be in the rectifying tower under the high vacuum state, then the tower still is heated with oil bath.Residual voltage 1.0Kpa in the rectification process device, 106～144 ℃ of temperature in the kettle, elder generation's total reflux operation 1 hour, regulating reflux ratio is 2.5, collect the cut of 69～75 ℃ (overhead vapours temperature), collected cut was huge beans triolefin after GC-MS and GC assay determination in 2 hours, content is 97.5%wt, and the yield of huge beans triolefin is 93%.
Embodiment 3 α-ionol propionic ester is through the huge beans triolefin of reactive distillation system spices:
(concentration is 85%wt to take by weighing 180g α-ionol propionic ester, all the other are other violet alcohol esters) and join in the rectifying still, install the rectification process device, vacuumize to make with vacuum pump and be in the rectifying tower under the high vacuum state, then the tower still is heated with oil bath.Residual voltage 1.0Kpa in the rectification process device, 110～150 ℃ of temperature in the kettle, elder generation's total reflux operation 1 hour, regulating reflux ratio is 3, collect the cut of 60～66 ℃ (overhead vapours temperature), collected cut was huge beans triolefin after GC-MS and GC assay determination in 2 hours, content is 95%wt, and the yield of huge beans triolefin is 90%.
Claims (4)
1, be the method that spices is produced in the rectifying of raw material heat scission reaction with the violet alcohol ester, it is characterized in that: the heat scission reaction of raw material and the rectifying separation of product are finished in a stuffing rectification column simultaneously; The processing condition of reactive distillation processes are:
(1) reactive distillation processes carries out under high vacuum, and the working pressure in the rectifier unit is 0.3～2.0Kpa;
(2) temperature in the kettle of smart stream device is 80～160 ℃;
(3) the suitable first total reflux operation of device initial start stage is 1～2 hour, then in 2～3 times operations of reflux ratio;
(4), be target product of the present invention at the cut of 60～75 ℃ of boiling range scopes of overhead collection.
2, the method for production spices as claimed in claim 1, it is characterized in that: said violet alcohol ester is α-ionol acetic ester, α-ionol propionic ester, α-ionol butyric ester, a kind of in α-ionol valerate, or their mixture.
3, produce the method for spices according to claim 1, it is characterized in that: filler is various forms of Stainless Steel Helicess in the said stuffing rectification column, as the Raschig ring type, porous Raschig ring type, netted Raschig ring type, netted saddle-shape, a kind of in the spiral spring type or more than one.
4, produce the method for spices according to claim 1, it is characterized in that: said reactive distillation processes can be periodical operation, can be operate continuously also, should keep the material balance of in-out apparatus during operate continuously.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031151469A CN1205160C (en) | 2003-01-24 | 2003-01-24 | Method for producing perfume using ionol ester as raw material by thermo-wacking rectifying |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031151469A CN1205160C (en) | 2003-01-24 | 2003-01-24 | Method for producing perfume using ionol ester as raw material by thermo-wacking rectifying |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1434016A true CN1434016A (en) | 2003-08-06 |
| CN1205160C CN1205160C (en) | 2005-06-08 |
Family
ID=27634235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB031151469A Expired - Fee Related CN1205160C (en) | 2003-01-24 | 2003-01-24 | Method for producing perfume using ionol ester as raw material by thermo-wacking rectifying |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1205160C (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102140484A (en) * | 2010-12-16 | 2011-08-03 | 郑州奥利实业有限公司 | Synthesis method of 3-oxo-alpha-ionol esters |
| CN102286033A (en) * | 2011-09-05 | 2011-12-21 | 川渝中烟工业公司 | Monosaccharide beta-ionol carbonate diester compound as well as preparation method and application thereof |
| CN102617659A (en) * | 2012-03-09 | 2012-08-01 | 中国烟草总公司郑州烟草研究院 | Synthesis method for alpha-ionol glucoside, and application of alpha-ionol glucoside to flavoring of cigarettes |
| CN101671601B (en) * | 2009-09-23 | 2013-01-09 | 华宝食用香精香料（上海）有限公司 | Terpene essence for cigarettes, preparation method and use thereof |
| CN104830528A (en) * | 2015-04-23 | 2015-08-12 | 东莞波顿香料有限公司 | Preparation method and use method of aquilaria wood perfume |
| CN105559145A (en) * | 2015-12-17 | 2016-05-11 | 立场电子科技发展（上海）有限公司 | E-cigarette flavor and preparation method thereof |
| CN106478418A (en) * | 2016-10-09 | 2017-03-08 | 湖北中烟工业有限责任公司 | The cigarette preparation method and applications of latent perfume 3 cinnamic acid esters of monomer |
| CN113812668A (en) * | 2021-09-27 | 2021-12-21 | 浙江中烟工业有限责任公司 | Method for extracting rectified aroma substances by dry distillation of tobacco leaves |
-
2003
- 2003-01-24 CN CNB031151469A patent/CN1205160C/en not_active Expired - Fee Related
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101671601B (en) * | 2009-09-23 | 2013-01-09 | 华宝食用香精香料（上海）有限公司 | Terpene essence for cigarettes, preparation method and use thereof |
| CN102140484A (en) * | 2010-12-16 | 2011-08-03 | 郑州奥利实业有限公司 | Synthesis method of 3-oxo-alpha-ionol esters |
| CN102286033A (en) * | 2011-09-05 | 2011-12-21 | 川渝中烟工业公司 | Monosaccharide beta-ionol carbonate diester compound as well as preparation method and application thereof |
| CN102286033B (en) * | 2011-09-05 | 2014-05-07 | 川渝中烟工业有限责任公司 | Monosaccharide beta-ionol carbonate diester compound as well as preparation method and application thereof |
| CN102617659A (en) * | 2012-03-09 | 2012-08-01 | 中国烟草总公司郑州烟草研究院 | Synthesis method for alpha-ionol glucoside, and application of alpha-ionol glucoside to flavoring of cigarettes |
| CN104830528A (en) * | 2015-04-23 | 2015-08-12 | 东莞波顿香料有限公司 | Preparation method and use method of aquilaria wood perfume |
| CN105559145A (en) * | 2015-12-17 | 2016-05-11 | 立场电子科技发展（上海）有限公司 | E-cigarette flavor and preparation method thereof |
| CN106478418A (en) * | 2016-10-09 | 2017-03-08 | 湖北中烟工业有限责任公司 | The cigarette preparation method and applications of latent perfume 3 cinnamic acid esters of monomer |
| CN106478418B (en) * | 2016-10-09 | 2018-10-02 | 湖北中烟工业有限责任公司 | The preparation method and applications of the latent fragrant monomer 3- cinnamic acid esters of cigarette |
| CN113812668A (en) * | 2021-09-27 | 2021-12-21 | 浙江中烟工业有限责任公司 | Method for extracting rectified aroma substances by dry distillation of tobacco leaves |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1205160C (en) | 2005-06-08 |
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Assignee: Taicang Wenhua Industrial Co.,Ltd. Assignor: HUABAO XIANGHUA SCIENCE AND TE Contract fulfillment period: 2007.1.5 to 2022.1.5 Contract record no.: 2008320000037 Denomination of invention: Method for producing perfume using ionol ester as raw material by thermo-wacking rectifying Granted publication date: 20050608 License type: Exclusive license Record date: 20080806 |
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Owner name: YINGTAN HUABAO FLAVORS AND FRAGRANCES CO., LTD. Free format text: FORMER OWNER: TAICANG WENHUA INDUSTRIAL CO., LTD. Effective date: 20150107 |
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Free format text: CORRECT: ADDRESS; FROM: 215413 SUZHOU, JIANGSU PROVINCE TO: 335000 YINGTAN, JIANGXI PROVINCE |
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Effective date of registration: 20150107 Address after: 335000 Yingtan national hi tech Industrial Park, Longgang District, Jiangxi Patentee after: YINGTAN HUABAO FLAVORS AND FRAGRANCES CO.,LTD. Address before: 215413, No. 18, developed road, Banqiao Town, Jiangsu, Taicang Patentee before: Taicang Wenhua Industrial Co.,Ltd. |
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Address after: 335000 Yingtan national hi tech Industrial Park, Longgang District, Jiangxi Patentee after: YINGTAN HUABAO ESSENCE CO.,LTD. Address before: 335000 Yingtan national hi tech Industrial Park, Longgang District, Jiangxi Patentee before: YINGTAN HUABAO FLAVORS AND FRAGRANCES CO.,LTD. |
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Effective date of registration: 20170328 Address after: 224352 Jiangsu province Yancheng City Sheyang County Zhen bin Dong Cun Chiaki Patentee after: YANCHENG CITY CHUNZHU AROMA CO.,LTD. Address before: 335000 Yingtan national hi tech Industrial Park, Longgang District, Jiangxi Patentee before: YINGTAN HUABAO ESSENCE CO.,LTD. |
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Effective date of registration: 20170727 Address after: 201821 Shanghai Zhongke hi tech Industrial Park, No. 1305 Yecheng Road, Jiading District Patentee after: HUABAO XIANGHUA SCIENCE AND TE Address before: 224352 Jiangsu province Yancheng City Sheyang County Zhen bin Dong Cun Chiaki Patentee before: YANCHENG CITY CHUNZHU AROMA CO.,LTD. |
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