CN104478666A - Method for preparing isoborneol through continuous saponification of isobornyl acetate - Google Patents
Method for preparing isoborneol through continuous saponification of isobornyl acetate Download PDFInfo
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- CN104478666A CN104478666A CN201410805472.4A CN201410805472A CN104478666A CN 104478666 A CN104478666 A CN 104478666A CN 201410805472 A CN201410805472 A CN 201410805472A CN 104478666 A CN104478666 A CN 104478666A
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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
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
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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
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
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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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
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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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/78—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by condensation or crystallisation
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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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
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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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/86—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
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Abstract
The invention discloses a method for preparing isoborneol through continuous saponification of isobornyl acetate. Sodiumhydroxide and the isobornyl acetate are used as raw materials, and white isoborneol crystals are prepared through steps of saponification, rectification, layering, water washing, crystallization and the like. Continuous operation of a saponification reaction can be realized in an oscillatory flow reactor, a static mixer or an ultrasonic mixer; a polar solvent is added during reaction, so that the saponification reaction is conducted at a homogeneous phase, the reaction time can be shortened, the reaction temperature can be reduced, the conversion rate of the isobornyl acetate exceeds 99%, and the product yield exceeds 95%; the method is low in energy consumption for production and high in product yield.
Description
Technical field
The invention belongs to chemical field, be specifically related to a kind of method that isocamphol is prepared in compounding acetic isoborneol ester continuous saponification.
Background technology
Isocamphol, also known as isocamphol, is elite stand Chemicals, is the epimer of borneol, molecular formula C
10h
18o.Isocamphol has special smell, can be used for spices and field of medicaments, is the intermediate of artificial camphor.
The synthetic method of current industrial isocamphol mainly contains indirect method and direct method two kinds of techniques.Direct method be under an acidic catalyst effect by amphene direct hydration generate isocamphol, its advantage is a simplified step, saves raw material, but transformation efficiency and selectivity relatively low.Indirect method generates compounding acetic isoborneol ester with amphene and acid esterification, then generate isocamphol with compounding acetic isoborneol ester saponification, and the method technique is more ripe.In current commercial synthesis adopt indirect method synthesis isocamphol more, but the shortcoming such as its saponification reaction is periodical operation, and have saponification process complexity, long reaction time, energy consumption is high, and yield is lower.Thus select suitable reactor, solubility promoter is the key improving compounding acetic isoborneol ester saponification reaction efficiency in indirect method.The invention provides that a kind of yield is higher, the reaction times is shorter, energy consumption and production cost lower, the industrial production method realizing the isocamphol of continuous operation, to meet the needs that modern industry is produced.
Summary of the invention
The object of the present invention is to provide a kind of compounding acetic isoborneol ester continuous saponification to prepare the method for isocamphol, be with sodium hydroxide and compounding acetic isoborneol ester for raw material, realize industrialization continuous saponification and prepare isocamphol.The method reaction conditions is gentle, the reaction times is short, the transformation efficiency of compounding acetic isoborneol ester more than 99%, product yield more than 95%, and can recycling polar solvent.
For achieving the above object, the present invention adopts following technical scheme:
A method for isocamphol is prepared in compounding acetic isoborneol ester continuous saponification, is that its preparation method comprises the step of saponification, rectifying, layering, washing, crystallization with sodium hydroxide and compounding acetic isoborneol ester for isocamphol prepared by raw material.
Specifically comprise the following steps:
1) stir after aqueous sodium hydroxide solution being mixed with polar solvent, be mixed with polar solvent;
2) respectively the polar solvent of compounding acetic isoborneol ester and step 1) is pumped into from one end of saponification reaction device, carry out saponification reaction;
3) respectively non-polar solvent and water are pumped into from the saponification reaction device the other end, after the solution after saponification reaction is mixed with non-polar solvent, water, export extraction reaction solution from saponification reaction device;
4) reaction solution is pumped in rectifying tower, adopt atmospheric distillation to reclaim the polar solvent in reaction solution; Gained polar solvent, from overhead extraction, can be reused, and all the other solution are from tower reactor extraction;
5) solution of tower reactor extraction is carried out layering, oil phase is the mixed solution containing isocamphol, and aqueous phase is sodium acetate aqueous solution;
6) wash with water after oil phase extraction, stratification, washing is until elutant pH is in neutral repeatedly;
7) adopt evaporative crystallization method, crystallization, filtration are carried out to the oil phase after washing, obtains white isocamphol crystal.
The mol ratio of aqueous sodium hydroxide solution described in step 1) and polar solvent is 1:1 ~ 6;
The massfraction of described aqueous sodium hydroxide solution is 30 ~ 46%;
Described polar solvent comprises acetone, methyl alcohol, acetonitrile, Virahol, dioxane.
Step 2) purity >=97% of described compounding acetic isoborneol ester.
Step 2) mol ratio of compounding acetic isoborneol ester and sodium hydroxide is 1:1.05 ~ 1.25 in described saponification reaction.
Step 2) described saponification reaction device is Oscillatory Flow Reactor, static mixer or ultrasonic mixer.
Step 2) reaction times of described saponification reaction is 10 ~ 60 min, temperature of reaction is 60 ~ 100 DEG C.
In step 3), the mol ratio of compounding acetic isoborneol ester, non-polar solvent and water is 1:1 ~ 2:2 ~ 6;
Described non-polar solvent is benzene kind solvent.
remarkable advantage of the present invention is:
(1) the present invention adopts polar solvent in saponification process, transfers two alternate saponification reactions to homogeneous reaction, makes the condition of saponification reaction more gentle, and makes the saponification reaction time foreshorten to 10 ~ 60min from 8 ~ 10h, shortens the reaction times greatly.
(2) saponification reaction of the present invention adopts oscillatory flow mixing tank, static mixer or ultrasonic mixer, and saponification reaction can be made to realize operate continuously.
(3) utilize the present invention to carry out the preparation of isocamphol, the transformation efficiency of its compounding acetic isoborneol ester more than 99%, product yield more than 95%.
(4) add the step of rectifying in preparation technology of the present invention, can reclaim polar solvent, and reusable, decrease the discharge of waste liquid, be conducive to ensured sustained development and produce.
Accompanying drawing explanation
Fig. 1 is the process flow sheet that isocamphol is prepared in embodiment 1 and embodiment 2 continuous saponification;
Wherein: 1-aqueous sodium hydroxide solution opening for feed, 2-polar solvent opening for feed, 3-compounding acetic isoborneol ester opening for feed, 4-non-polar solvent opening for feed, 5-water opening for feed, 6-polar solvent exports, 7-water opening for feed, 8-isocamphol discharge port; V-101-polar solvent storage tank, V-102-container for storing liquid, V-103-quantizer, V-104-washing kettle, P-101-vibrates pump, R-101-saponification reaction device, T-101-rectifying tower, D-101-crystallizer.
Fig. 2 is the process flow sheet that isocamphol is prepared in embodiment 3 continuous saponification;
Wherein: 1-aqueous sodium hydroxide solution opening for feed, 2-polar solvent opening for feed, 3-compounding acetic isoborneol ester opening for feed, 4-non-polar solvent opening for feed, 5-water opening for feed, 6-polar solvent exports, 7-water opening for feed, 8-isocamphol discharge port; V-101-polar solvent storage tank, V-102-container for storing liquid, V-103-quantizer, V-104-washing kettle, R-101-saponification reaction device, T-101-rectifying tower, D-101-crystallizer.
Embodiment
More being convenient to make content of the present invention understand, below in conjunction with embodiment, technical solutions according to the invention are described further, but the present invention being not limited only to this.
Embodiment 1
A method for isocamphol is prepared in compounding acetic isoborneol ester continuous saponification, specifically comprises the following steps:
1) by massfraction be 46% aqueous sodium hydroxide solution (1) and polar solvent acetone (2) pump into polar solvent storage tank V-101, stir after mixing, be mixed with polar solvent; The mol ratio of described aqueous sodium hydroxide solution and acetone is 1:3;
2) be 1:1.2 by the mol ratio of compounding acetic isoborneol ester and sodium hydroxide, respectively the polar solvent of compounding acetic isoborneol ester (3) and step 1) is pumped into the Oscillatory Flow Reactor R-101 as Fig. 1, circulating water temperature is stablized to 80 DEG C, open vibration pump P-101 simultaneously, regulate oscillation frequency 4Hz, oscillation amplitude 0.03m, saponification reaction 30 min; The purity of described compounding acetic isoborneol ester is 97.8%;
3) when in question response device, stock liquid height reaches non-polar solvent entrance height, be 1:1.5:5 by the mol ratio of compounding acetic isoborneol ester, non-polar solvent and water, respectively non-polar solvent dimethylbenzene (4) and water (5) are pumped into from reactor top, from reactor head extraction reaction solution after making the solution after saponification reaction mix with dimethylbenzene, water, pump into container for storing liquid V-102;
4) reaction solution in V-102 is pumped in rectifying tower T-101, adopt atmospheric distillation to reclaim the polar solvent in reaction solution, tower top temperature 55 DEG C, temperature 70 C in tower, bottom temperature 80 DEG C; Gained polar solvent (6) is from overhead extraction, and all the other solution, from tower reactor extraction, pump into quantizer V-103 and carry out layering, and gained oil phase is the mixed solution containing isocamphol, and aqueous phase is sodium acetate aqueous solution;
5) pump into washing kettle V-104 by after oil phase extraction, and pump into water (7) and carry out washing rear stratification, washing is until elutant pH is in neutral repeatedly;
6) oil phase after washing is pumped into crystallizer D-101, adopt evaporative crystallization method, crystallization, filtration are carried out to it, obtains white isocamphol crystal (8).
Adopt the content of gas chromatograph to compounding acetic isoborneol ester, isocamphol to analyze, in this product be obtained by reacting, isocamphol purity is 95.8%, compounding acetic isoborneol ester conversion rate 99.3%, isocamphol yield 95.4%.
Embodiment 2
A method for isocamphol is prepared in compounding acetic isoborneol ester continuous saponification, specifically comprises the following steps:
1) by massfraction be 40% aqueous sodium hydroxide solution (1) and polar solvent methyl alcohol (2) pump into polar solvent storage tank V-101, stir after mixing, be mixed with polar solvent; The mol ratio of described aqueous sodium hydroxide solution and methyl alcohol is 1:1.4;
2) be 1:1.15 by the mol ratio of compounding acetic isoborneol ester and sodium hydroxide, respectively the polar solvent of compounding acetic isoborneol ester (3) and step 1) is pumped into the Oscillatory Flow Reactor R-101 as Fig. 1, circulating water temperature is stablized to 70 DEG C, open vibration pump P-101 simultaneously, regulate oscillation frequency 3Hz, oscillation amplitude 0.05m, saponification reaction 25 min; The purity of described compounding acetic isoborneol ester is 97.3%;
3) when in question response device, stock liquid height reaches non-polar solvent entrance height, be 1:1.3:2 by the mol ratio of compounding acetic isoborneol ester, non-polar solvent and water, respectively non-polar solvent toluene (4) and water (5) are pumped into from reactor top, from reactor head extraction reaction solution after making the solution after saponification reaction mix with toluene, water, pump into container for storing liquid V-102;
4) reaction solution in V-102 is pumped in rectifying tower T-101, adopt atmospheric distillation to reclaim the polar solvent in reaction solution, tower top temperature 55 DEG C, temperature 70 C in tower, bottom temperature 80 DEG C; Gained polar solvent (6) is from overhead extraction, and all the other solution, from tower reactor extraction, pump into quantizer V-103 and carry out layering, and gained oil phase is the mixed solution containing isocamphol, and aqueous phase is sodium acetate aqueous solution;
5) pump into washing kettle V-104 by after oil phase extraction, and pump into water (7) and carry out washing rear stratification, washing is until elutant pH is in neutral repeatedly;
6) oil phase after washing is pumped into crystallizer D-101, adopt evaporative crystallization method, crystallization, filtration are carried out to it, obtains white isocamphol crystal (8).
Adopt the content of gas chromatograph to compounding acetic isoborneol ester, isocamphol to analyze, in this product be obtained by reacting, isocamphol purity is 96.15%, compounding acetic isoborneol ester conversion rate 99.5%, isocamphol yield 96.1%.
Embodiment 3
A method for isocamphol is prepared in compounding acetic isoborneol ester continuous saponification, specifically comprises the following steps:
1) by massfraction be 30% aqueous sodium hydroxide solution (1) and polar solvent Virahol (2) pump into polar solvent storage tank V-101, stir after mixing, be mixed with polar solvent; The mol ratio of described aqueous sodium hydroxide solution and Virahol is 1:6;
2) be 1:1.1 by the mol ratio of compounding acetic isoborneol ester and sodium hydroxide, respectively the polar solvent of compounding acetic isoborneol ester (3) and step 1) pumped into the static mixer R-101 as Fig. 2, circulating water temperature is stablized to 60 DEG C, saponification reaction 10 min; The purity of described compounding acetic isoborneol ester is 97.1%;
3) when in question response device, stock liquid height reaches non-polar solvent entrance height, be 1:2:6 by the mol ratio of compounding acetic isoborneol ester, non-polar solvent and water, respectively non-polar solvent diethylbenzene (4) and water (5) are pumped into from reactor top, from reactor head extraction reaction solution after making the solution after saponification reaction mix with diethylbenzene, water, pump into container for storing liquid V-102;
4) reaction solution in V-102 is pumped in rectifying tower T-101, adopt atmospheric distillation to reclaim the polar solvent in reaction solution, tower top temperature 55 DEG C, temperature 70 C in tower, bottom temperature 80 DEG C; Gained polar solvent (6) is from overhead extraction, and all the other solution, from tower reactor extraction, pump into quantizer V-103 and carry out layering, and gained oil phase is the mixed solution containing isocamphol, and aqueous phase is sodium acetate aqueous solution;
5) pump into washing kettle V-104 by after oil phase extraction, and pump into water (7) and carry out washing rear stratification, washing is until elutant pH is in neutral repeatedly;
6) oil phase after washing is pumped into crystallizer D-101, adopt evaporative crystallization method, crystallization, filtration are carried out to it, obtains white isocamphol crystal (8).
Adopt the content of gas chromatograph to compounding acetic isoborneol ester, isocamphol to analyze, in this product be obtained by reacting, isocamphol purity is 95.03%, compounding acetic isoborneol ester conversion rate 99.2%, isocamphol yield 95.2%.
The foregoing is only preferred embodiment of the present invention, all equalizations done according to the present patent application the scope of the claims change and modify, and all should belong to covering scope of the present invention.
Claims (8)
1. a method for isocamphol is prepared in compounding acetic isoborneol ester continuous saponification, it is characterized in that: with sodium hydroxide and compounding acetic isoborneol ester for isocamphol prepared by raw material, its preparation method comprises the step of saponification, rectifying, layering, washing, crystallization.
2. the method for isocamphol is prepared in compounding acetic isoborneol ester continuous saponification according to claim 1, it is characterized in that: specifically comprise the following steps:
1) stir after aqueous sodium hydroxide solution being mixed with polar solvent, be mixed with polar solvent;
2) respectively the polar solvent of compounding acetic isoborneol ester and step 1) is pumped into from one end of saponification reaction device, carry out saponification reaction;
3) respectively non-polar solvent and water are pumped into from the saponification reaction device the other end, after the solution after saponification reaction is mixed with non-polar solvent, water, export extraction reaction solution from saponification reaction device;
4) reaction solution is pumped in rectifying tower, adopt atmospheric distillation to reclaim the polar solvent in reaction solution; Gained polar solvent is from overhead extraction, and all the other solution are from tower reactor extraction;
5) solution of tower reactor extraction is carried out layering, gained oil phase is the mixed solution containing isocamphol, and aqueous phase is sodium acetate aqueous solution;
6) wash with water after oil phase extraction, stratification, washing is until elutant pH is in neutral repeatedly;
7) adopt evaporative crystallization method, crystallization, filtration are carried out to the oil phase after washing, obtains white isocamphol crystal.
3. the method for isocamphol is prepared in compounding acetic isoborneol ester continuous saponification according to claim 2, it is characterized in that: the mol ratio of aqueous sodium hydroxide solution described in step 1) and polar solvent is 1:1 ~ 6;
The massfraction of described aqueous sodium hydroxide solution is 30 ~ 46%;
Described polar solvent comprises acetone, methyl alcohol, acetonitrile, Virahol, dioxane.
4. the method for isocamphol is prepared in compounding acetic isoborneol ester continuous saponification according to claim 2, it is characterized in that: step 2) purity >=97% of described compounding acetic isoborneol ester.
5. the method for isocamphol is prepared in compounding acetic isoborneol ester continuous saponification according to claim 2, it is characterized in that: step 2) mol ratio of compounding acetic isoborneol ester and sodium hydroxide is 1:1.05 ~ 1.25 in described saponification reaction.
6. the method for isocamphol is prepared in compounding acetic isoborneol ester continuous saponification according to claim 2, it is characterized in that: step 2) described saponification reaction device is Oscillatory Flow Reactor, static mixer or ultrasonic mixer.
7. the method for isocamphol is prepared in compounding acetic isoborneol ester continuous saponification according to claim 2, it is characterized in that: step 2) reaction times of described saponification reaction is 10 ~ 60 min, temperature of reaction is 60 ~ 100 DEG C.
8. the method for isocamphol is prepared in compounding acetic isoborneol ester continuous saponification according to claim 2, it is characterized in that: in step 3), the mol ratio of compounding acetic isoborneol ester, non-polar solvent and water is 1:1 ~ 2:2 ~ 6;
Described non-polar solvent is benzene kind solvent.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410805472.4A CN104478666B (en) | 2014-08-25 | 2014-12-23 | The method of isocamphol is prepared in a kind of compounding acetic isoborneol ester continuous saponification |
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|---|---|---|---|
| CN201410419904.8A CN104193591A (en) | 2014-08-25 | 2014-08-25 | Method for preparing isoborneol by continuous saponification of isobornyl acetate |
| CN2014104199048 | 2014-08-25 | ||
| CN201410805472.4A CN104478666B (en) | 2014-08-25 | 2014-12-23 | The method of isocamphol is prepared in a kind of compounding acetic isoborneol ester continuous saponification |
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| CN104478666A true CN104478666A (en) | 2015-04-01 |
| CN104478666B CN104478666B (en) | 2016-03-09 |
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| CN201410419904.8A Withdrawn CN104193591A (en) | 2014-08-25 | 2014-08-25 | Method for preparing isoborneol by continuous saponification of isobornyl acetate |
| CN201410805472.4A Active CN104478666B (en) | 2014-08-25 | 2014-12-23 | The method of isocamphol is prepared in a kind of compounding acetic isoborneol ester continuous saponification |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105837435A (en) * | 2016-04-25 | 2016-08-10 | 福州大学 | Method for preparing isoborneol ester through continuous esterification |
| CN108250045A (en) * | 2018-03-11 | 2018-07-06 | 福建青松股份有限公司 | Method for preparing high-purity borneol from borneol oxalate |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101318880A (en) * | 2008-07-23 | 2008-12-10 | 嘉兴学院 | Green synthesis process for bornyl alcohol |
| CN102241567A (en) * | 2011-04-29 | 2011-11-16 | 南宁辰康生物科技有限公司 | One-step method for synthesizing fenchol with turpentine |
| CN102344343A (en) * | 2011-08-18 | 2012-02-08 | 福建青松股份有限公司 | Method for producing high-purity isoborneol |
| CN103483152A (en) * | 2013-09-22 | 2014-01-01 | 云南林缘香料有限公司 | Process for producing borneol by adopting alpha-pinene |
-
2014
- 2014-08-25 CN CN201410419904.8A patent/CN104193591A/en not_active Withdrawn
- 2014-12-23 CN CN201410805472.4A patent/CN104478666B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101318880A (en) * | 2008-07-23 | 2008-12-10 | 嘉兴学院 | Green synthesis process for bornyl alcohol |
| CN102241567A (en) * | 2011-04-29 | 2011-11-16 | 南宁辰康生物科技有限公司 | One-step method for synthesizing fenchol with turpentine |
| CN102344343A (en) * | 2011-08-18 | 2012-02-08 | 福建青松股份有限公司 | Method for producing high-purity isoborneol |
| CN103483152A (en) * | 2013-09-22 | 2014-01-01 | 云南林缘香料有限公司 | Process for producing borneol by adopting alpha-pinene |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105837435A (en) * | 2016-04-25 | 2016-08-10 | 福州大学 | Method for preparing isoborneol ester through continuous esterification |
| CN105837435B (en) * | 2016-04-25 | 2018-10-30 | 福州大学 | A kind of method that continuous esterification prepares compounding acetic isoborneol ester |
| CN108250045A (en) * | 2018-03-11 | 2018-07-06 | 福建青松股份有限公司 | Method for preparing high-purity borneol from borneol oxalate |
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| Publication number | Publication date |
|---|---|
| CN104193591A (en) | 2014-12-10 |
| CN104478666B (en) | 2016-03-09 |
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