CN104151142A - Preparation method of isoborneol - Google Patents
Preparation method of isoborneol Download PDFInfo
- Publication number
- CN104151142A CN104151142A CN201410396803.3A CN201410396803A CN104151142A CN 104151142 A CN104151142 A CN 104151142A CN 201410396803 A CN201410396803 A CN 201410396803A CN 104151142 A CN104151142 A CN 104151142A
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- reactant
- amphene
- still kettle
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- isocamphol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/20—All rings being cycloaliphatic the ring system containing seven carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of isoborneol. The preparation method comprises the following steps: mixing a camphene mixture containing over 95 percent of camphene, a solvent and water in a ratio of 1:(2-5):(0.36-0.72); feeding the mixture into a distillation kettle for heating and distilling; after an azeotropic temperature is reached, condensing a distillation product rising to the tower top of the distillation kettle to form distillate; making the distillate reflow into the distillation kettle through a fixed bed catalytic reactor; 8 hours later, sampling a reactant in the distillation kettle for analysis, and stopping heating till the content of the camphene in the reactant is less than or equal to 3 percent; and cooling the reactant to a temperature below 40 DEG C, and discharging the reactant. Compared with the prior art, the preparation method has the advantages that the problems of high production cost, low efficiency and high pollution in the conventional isoborneol can be solved.
Description
Technical field
The present invention relates to turps deep process technology field, especially a kind of method of amphene one-step synthesis isocamphol.
Background technology
Along with China is to utilizing turps to extract going deep into of synthetic perfume research, the research of α-pinene gets most of the attention more, and camphor, isocamphol be one of them of the large deep processed product of α-pinene especially.Existing enterprise is when being used turps to produce isocamphol, camphor, by amphene, to isocamphol, be substantially all to adopt two-step approach to realize, first pass through esterification synthesis of acetic acid Isobornyl, carry out again saponification and obtain isocamphol, like this, owing to using acetic acid to cause certain corrosion to equipment, but also increased by a procedure, increased manpower and materials, height production cost, and production efficiency is not high yet.
Summary of the invention
Problem to be solved by this invention is to provide a kind of preparation method of isocamphol, and high to solve the production cost of existing isocamphol, efficiency is low, heavy-polluted problem.
In order to address the above problem, technical scheme of the present invention is: the preparation method of this isocamphol comprises the following steps: by amphene content, be more than 95% amphene mixture, solvent and water are pressed the weight ratio of 1:2～5:0.36～0.72 and are mixed, drop into still kettle and add thermal distillation, reach after azeotropic temperature, the product of distillation that the rises to described still kettle tower top formation distillate that is condensed, described distillate flows back in described still kettle by fixed catalytic bed, after 8 hours, start the reactant in described still kettle to carry out sampling analysis, until stop heating in described reactant after amphene content≤3%, be cooled to 40 ℃ with bottom discharge, described azeotropic temperature: 60 ℃～80 ℃, described fixed catalytic bed temperature of reaction: 50 ℃～80 ℃, described solvent is Virahol, and described fixed catalytic bed catalyzer is solid acid catalyst.
Owing to having adopted technique scheme, the present invention compared with prior art has following beneficial effect:
Present method provides and can a kind of preparation method by isocamphol adopt efficient solvent and amphene and water to form azeotrope, is evaporated to condenser and is back to the catalyst fixed bed synthetic isocamphol of hydration reaction that carries out again.Isocamphol is prepared in present method one step hydration, compare existing esterification, saponification two step synthesis isocamphol, the present invention has reduced single step reaction than original technique, reduced production cost, do not need to use acetic acid, the corrosion and the water that have reduced equipment pollute, and have improved production efficiency, and the present invention is the green synthesis process without any pollutant emission without waste water especially.
Embodiment
Below by embodiment, the invention will be further described:
Embodiment mono-:
Use present method processing isocamphol, carry out according to the following steps: in the still kettle with thermometer, add the amphene mixture that 100 grams of amphene content are 96.1%, add 500 grams of solvent Virahols, 72 grams of deionized waters, start heating, in still kettle, after material arrival azeotropic temperature, distill produce and be evaporated to tower top, by overhead condenser by the product of distillation formation distillate that cools down, the distillate that condensation is got off is back to and the fixed catalytic bed of catalyzer is housed flow back in still kettle, and now still kettle azeotropic temperature is 60 ℃; Fixed catalytic bed temperature of reaction is 50 ℃, and catalyzer is solid acid catalyst; Evaporation back flow reaction starts the reactant in still kettle to carry out sampling analysis amphene content after 8 hours, in reactant, during amphene content≤3%, stop heating, and tower reactor cools to 40 ℃, and discharging obtains the isocamphol of 100 grams.Isocamphol is analyzed: amphene content is: 1.7%, and isocamphol content is: 88.1%, transformation efficiency is: 98.2%, selectivity is: 93.3%.The rear product of purifying respectively detects index and is: outward appearance is white powder crystal; Whiteness 87 %; 206 ℃ of fusing points; Water content detection: 10%(W/V) petroleum ether solution is Clear & Transparent; Content: 95.1%.Reach isocamphol quality standard.
Embodiment bis-:
Use present method processing isocamphol, carry out according to the following steps: in the still kettle with thermometer, add the amphene mixture that 500 grams of amphene content are 95.8%, add 1600 grams of solvent Virahols, 250 grams of deionized waters, start heating, after in still kettle, material arrives azeotropic temperature, product of distillation is evaporated to tower top, by overhead condenser by the product of distillation formation distillate that cools down, the distillate that condensation is got off is back to and the fixed catalytic bed of catalyzer is housed flow back in still kettle, and now still kettle azeotropic temperature is 68 ℃; Fixed catalytic bed temperature of reaction is 62 ℃, and catalyzer is solid acid catalyst; Evaporation back flow reaction starts the reactant in still kettle to carry out sampling analysis amphene content after 8 hours, in reactant, during amphene content≤3%, stop heating, and tower reactor cools to 40 ℃, and discharging obtains the isocamphol of 500 grams.Isocamphol is analyzed: amphene content is: 2.5%, and isocamphol content is: 87.2%, transformation efficiency is: 97.4%, selectivity is: 93.5%.The rear product of purifying respectively detects index and is: outward appearance is white powder crystal; Whiteness 86 %; 205 ℃ of fusing points; Water content detection: 10%(W/V) petroleum ether solution is Clear & Transparent; Content: 95.0%.Reach isocamphol quality standard.
Embodiment tri-:
Use present method processing isocamphol, carry out according to the following steps: in the still kettle with thermometer, add the amphene mixture that 1500 grams of amphene content are 95.6%, add 3000 grams of solvent Virahols, 540 grams of deionized waters, start heating, after in still kettle, material arrives azeotropic temperature, product of distillation is evaporated to tower top, by overhead condenser by the product of distillation formation distillate that cools down, the distillate that condensation is got off is back to and the fixed catalytic bed of catalyzer is housed flow back in still kettle, and now still kettle azeotropic temperature is 80 ℃; Fixed catalytic bed temperature of reaction is 80 ℃, and catalyzer is solid acid catalyst; Evaporation back flow reaction starts the reactant in still kettle to carry out sampling analysis amphene content after 8 hours, in reactant, during amphene content≤3%, stop heating, and tower reactor cools to 40 ℃, and discharging obtains the isocamphol of 1500 grams.Isocamphol is analyzed: amphene content is: 2.1%, and isocamphol content is: 87.8%, transformation efficiency is: 97.8%, selectivity is: 93.9%.The rear product of purifying respectively detects index and is: outward appearance is white powder crystal; Whiteness 87 %; 206 ℃ of fusing points; Water content detection: 10%(W/V) petroleum ether solution is Clear & Transparent; Content: 95.2%.Reach isocamphol quality standard.
Claims (1)
1. the preparation method of an isocamphol, it is characterized in that comprising the following steps: by amphene content, be more than 95% amphene mixture, solvent and water are pressed the weight ratio of 1:2～5:0.36～0.72 and are mixed, drop into still kettle and add thermal distillation, reach after azeotropic temperature, the product of distillation that the rises to described still kettle tower top formation distillate that is condensed, described distillate flows back in described still kettle by fixed catalytic bed, after 8 hours, start the reactant in described still kettle to carry out sampling analysis, until stop heating in described reactant after amphene content≤3%, be cooled to 40 ℃ with bottom discharge,
Described azeotropic temperature: 60 ℃～80 ℃; Described fixed catalytic bed temperature of reaction: 50 ℃～80 ℃, described solvent is Virahol, and described fixed catalytic bed catalyzer is solid acid catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410396803.3A CN104151142A (en) | 2014-08-13 | 2014-08-13 | Preparation method of isoborneol |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410396803.3A CN104151142A (en) | 2014-08-13 | 2014-08-13 | Preparation method of isoborneol |
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| Publication Number | Publication Date |
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| CN104151142A true CN104151142A (en) | 2014-11-19 |
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| CN201410396803.3A Pending CN104151142A (en) | 2014-08-13 | 2014-08-13 | Preparation method of isoborneol |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116375562A (en) * | 2023-03-31 | 2023-07-04 | 福州大学 | Refining method for preparing isoborneol by camphene hydration |
| CN116375562B (en) * | 2023-03-31 | 2024-05-31 | 福州大学 | Refining method for preparing isoborneol by camphene hydration |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB190126619A (en) * | 1901-12-30 | 1902-11-20 | August Zimmermann | The Manufacture of Camphene. |
| CN85104105A (en) * | 1985-05-29 | 1986-11-26 | 南开大学 | Preparation of camphor by resin catalized direct hydration of camphene |
| CN1049842A (en) * | 1990-06-05 | 1991-03-13 | 中国科学院广州化学所 | Synthetic method of isoborneol by catalyzing camphenic water with resin |
| CN103739447A (en) * | 2013-12-31 | 2014-04-23 | 南京运华立太能源科技有限公司 | Isoborneol production method |
-
2014
- 2014-08-13 CN CN201410396803.3A patent/CN104151142A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB190126619A (en) * | 1901-12-30 | 1902-11-20 | August Zimmermann | The Manufacture of Camphene. |
| CN85104105A (en) * | 1985-05-29 | 1986-11-26 | 南开大学 | Preparation of camphor by resin catalized direct hydration of camphene |
| CN1049842A (en) * | 1990-06-05 | 1991-03-13 | 中国科学院广州化学所 | Synthetic method of isoborneol by catalyzing camphenic water with resin |
| CN103739447A (en) * | 2013-12-31 | 2014-04-23 | 南京运华立太能源科技有限公司 | Isoborneol production method |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116375562A (en) * | 2023-03-31 | 2023-07-04 | 福州大学 | Refining method for preparing isoborneol by camphene hydration |
| CN116375562B (en) * | 2023-03-31 | 2024-05-31 | 福州大学 | Refining method for preparing isoborneol by camphene hydration |
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Application publication date: 20141119 |
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