CN104276947B - A kind of method that natural d-borneol prepares dextrorotation Bronyl acetate - Google Patents
A kind of method that natural d-borneol prepares dextrorotation Bronyl acetate Download PDFInfo
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- CN104276947B CN104276947B CN201410482083.2A CN201410482083A CN104276947B CN 104276947 B CN104276947 B CN 104276947B CN 201410482083 A CN201410482083 A CN 201410482083A CN 104276947 B CN104276947 B CN 104276947B
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- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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Abstract
The invention discloses a kind of method that utilization natural d-borneol prepares dextrorotation Bronyl acetate.It is the ratio 1～2 of the amount that acetic anhydride and natural d-borneol are pressed material with natural d-borneol and acetic anhydride as raw material:1 is dosed in reaction dissolvent petroleum ether, and natural d-borneol is 1 with the solid-liquid ratio of petroleum ether：10～15g/ml, contains P in reaction dissolvent2O5Or P2O5‑H3PO4Used as catalyst, the consumption of catalyst is the 5%～10% of natural borneol quality, and reaction temperature is 55 DEG C～75 DEG C, esterification 4h～10h under condition of normal pressure, obtains dextrorotation Bronyl acetate after purification.The dextrorotation Bronyl acetate that percentage contents are not less than 97% can be obtained using the method for the present invention.Meanwhile, after reaction terminates, the mixed solution of recoverable reaction system remaining solvent, acetic acid and acetic anhydride.The present invention direct effect be：In the synthetic product for being obtained, dextrorotation Bronyl acetate purity is high, and feed stock conversion is high, chemical reaction yield is high, and reaction selectivity is high.
Description
Technical field：
The invention belongs to technical field of fine, and in particular to a kind of natural d-borneol prepares dextrorotation Bronyl acetate
Method.
Background technology：
Bronyl acetate is also called borneolacetate, is colourless liquid and crystalline solid.There is antidiarrheal, analgesia, suppress intestines to put down
The effects such as sliding muscle spasmus, wherein analgesic activity is more obvious.And room spray spices, bath spices, the important set of talcum powder
Point.Natural acetic acid is found in canella ox Pan Shu current leaf, the leaf of zingiberaceous plant amomum viosum and the volatile oil of seed
Borneol acetate, is generally present with levo form form.
Under conventional process conditions, it is raw material through sulphuric acid catalysis, lactate synthesis Bronyl acetate generally with australene.Simultaneously
As reaction system adds the concentrated sulfuric acid to make catalyst, as the concentrated sulfuric acid makees catalyst while having esterification, dehydration, oxidation etc. to make
With, causing the generation of serial side reaction, cause esterification yield low, reaction selectivity is poor, and accessory substance is more, and separating-purifying is difficult, sewage
Discharge capacity is big, and significant loss is big, the problems such as severe corrosion equipment.Also paper report urges using rare-earth dust
Agent prepares Bronyl acetate, but the preparation process of catalyst is complicated, and solid acid post-processing step is complicated, acetic acid in synthetic product
Borneol ester content is not high.
Content of the invention：
It is an object of the invention to provide a kind of feed stock conversion is high, reaction yield is high, reaction selectivity is high, can be easily separated pure
Change, the method that the natural d-borneol that dextrorotation Bronyl acetate purity is high in synthetic product prepares dextrorotation Bronyl acetate.
The method that the utilization natural d-borneol of the present invention prepares dextrorotation Bronyl acetate, it is characterised in that including following
Step：
With natural d-borneol and acetic anhydride as raw material, acetic anhydride and natural d-borneol are pressed the ratio 1 of the amount of material～
2:1 is dosed in reaction dissolvent petroleum ether, and natural d-borneol is 1 with the solid-liquid ratio of petroleum ether：10～15g/ml, reaction dissolvent
In contain P2O5Or P2O5-H3PO4Used as catalyst, the consumption of catalyst is the 5%～10% of natural d-borneol quality, reaction
Temperature is 55 DEG C～75 DEG C, esterification 4h～10h under condition of normal pressure, obtains dextrorotation Bronyl acetate after purification.
Described petroleum ether is preferably the petroleum ether of 60 DEG C～90 DEG C of boiling range.
The dextrorotation Bronyl acetate that percentage contents are not less than 97% can be obtained using the method for the present invention.Meanwhile,
After reaction terminates, the mixed solution of recoverable reaction system remaining solvent, acetic acid and acetic anhydride.The direct effect of the present invention
It is really：In the synthetic product for being obtained, dextrorotation Bronyl acetate purity is high, and feed stock conversion is high, chemical reaction yield is high, reaction
Selective high.Purpose compound dextrorotation Bronyl acetate has optical activity, and biology, medicine and pharmacology Utilization prospects are extensive.
Specific embodiment：
Following examples are that the present invention is further illustrated, rather than limitation of the present invention.
Embodiment 1：
Acetic anhydride and natural d-borneol, with natural d-borneol and acetic anhydride as raw material, are pressed the ratio 2 of the amount of material:1
It is dosed in reaction dissolvent petroleum ether (60 DEG C～90 DEG C of boiling range), natural d-borneol is 1 with the solid-liquid ratio of petroleum ether：10g/
Ml, contains P in reaction dissolvent2O5Used as catalyst, the consumption of catalyst is natural borneol quality 10%, and natural d-borneol fills
After dividing dissolving, adjustment reaction temperature is 75 DEG C, and acetic anhydride time for adding 0.5h, aceticanhydride are added dropwise 75 DEG C of process control temp.Aceticanhydride
After drop finishes, reactant continues at reaction 10h at 75 DEG C.Reaction pressure is under condition of normal pressure.After reaction terminates, 30% hydrogen-oxygen is first used
Change sodium solution to wash to system pH>7, it is washed with water to system pH=7.Steam solvent and residual moisture in system.Course of reaction
GC detections are carried out every 2h.As a result as shown in table 1：
Table 1
As it can be seen from table 1 in the presence of a catalyst, can just obtain percentage contents in 4-8 hours and be not less than
97% dextrorotation Bronyl acetate.
Embodiment 2
Acetic anhydride and natural d-borneol, with natural d-borneol and acetic anhydride as raw material, are pressed the ratio 2 of the amount of material:1
It is dosed in reaction dissolvent petroleum ether (60 DEG C～90 DEG C of boiling range), natural d-borneol is 1 with the solid-liquid ratio of petroleum ether：10g/
Ml, contains P in reaction dissolvent2O5Used as catalyst, the consumption of catalyst is the 10% of natural borneol quality, and raw material fully dissolves
Afterwards, adjustment system temperature is to 75 DEG C.Acetic anhydride time for adding 0.5h, acetic anhydride are added dropwise 75 DEG C of process control temp.Acetic anhydride drips
Bi Hou, reactant continue at reaction 6h at 75 DEG C.After reaction terminates, first washed to system pH with 30% sodium hydroxide solution>7,
It is washed with water to system pH=7.Solvent and residual moisture in system is steamed, synthetic product GC-MS testing results are as shown in table 2：
Table 2
Embodiment 3
Acetic anhydride and natural d-borneol, with natural d-borneol and acetic anhydride as raw material, are pressed the ratio 2 of the amount of material:1
It is dosed in reaction dissolvent petroleum ether (60 DEG C～90 DEG C of boiling range), natural d-borneol is 1 with the solid-liquid ratio of petroleum ether：10g/
Ml, contains P in reaction dissolvent2O5Used as catalyst, the consumption of catalyst is the 10% of natural borneol quality, and raw material fully dissolves
Afterwards, 75 DEG C of system temperature is adjusted.Aceticanhydride time for adding 0.5h, aceticanhydride are added dropwise 75 DEG C of process control temp.After aceticanhydride drop finishes, reaction
Thing continue with 75 DEG C at react 6h.After reaction terminates, under the conditions of low vacuum, recycling design is separately recovered solvent to 110 DEG C of temperature
The mixed solution (reclaiming solution reusable edible) of petroleum ether, acetic anhydride and acetic acid.Residue first uses 30% sodium hydroxide solution
Wash to system pH>7, it is washed with water to system pH=7.Steam solvent and residual moisture in system, product GC-MS testing results
Such as table 3：
Table 3
Embodiment 4
With P2O5With H3PO4Mass ratio 1：10 are stirred well to solution clear under the conditions of 35 DEG C, prepare P2O5-H3PO4
Composite catalyst.
Acetic anhydride and natural d-borneol, with natural d-borneol and acetic anhydride as raw material, are pressed the ratio 2 of the amount of material:1
It is dosed in reaction dissolvent petroleum ether (60 DEG C～90 DEG C of boiling range), natural d-borneol is 1 with the solid-liquid ratio of petroleum ether：10g/
Ml, contains P in reaction dissolvent2O5-H3PO4Used as catalyst, the consumption of catalyst is natural borneol quality to composite catalyst
10%, after raw material borneol fully dissolves, adjust 75 DEG C of system temperature.Acetic anhydride time for adding 0.5h, acetic anhydride was added dropwise program control
75 DEG C of temperature processed.Acetic anhydride drop finish after, reactant continue with 75 DEG C at react 6h.After reaction terminates, 30% NaOH is first used
Solution is washed to system pH>7, it is washed with water to system pH=7.Steam solvent and residual moisture in system, synthetic product GC-MS
Testing result such as table 4：
Table 4
Embodiment 5
With natural d-borneol and acetic anhydride as raw material, 1.84g P in 18.4g natural d-borneols, are added2O5, then plus
184g petroleum ethers (60～90 DEG C of boiling range) make reaction system solvent.Adjustment system temperature, is opened to 75 DEG C after material is completely dissolved
Begin 24.4g acetic anhydride is added dropwise.Acetic anhydride time for adding 0.5h, acetic anhydride are added dropwise 75 DEG C of process control system temperature.Aceticanhydride drop finishes
Afterwards, reactant continue with 75 DEG C at react 6h.After reaction terminates, first washed to system PH with 30% sodium hydroxide solution>7, then
Wash with water to system PH=7.Solvent and residual moisture in system is steamed, dextrorotation Bronyl acetate crude product 23.2g is obtained.Yield
97%, d-Bomeol conversion ratio 99.8%, reaction selectivity 97.2%, synthetic product specific rotatory power [α]20 D=+34.2 ° of products
Through GC-MS testing results such as table 5 below：
Table 5
Embodiment 6：
Acetic anhydride and natural d-borneol, with natural d-borneol and acetic anhydride as raw material, are pressed the ratio 1 of the amount of material:1
It is dosed in reaction dissolvent petroleum ether (60 DEG C～90 DEG C of boiling range), natural d-borneol is 1 with the solid-liquid ratio of petroleum ether：15g/
Ml, contains P in reaction dissolvent2O5Used as catalyst, the consumption of catalyst is the 5% of natural borneol quality, and raw material fully dissolves
Afterwards, system temperature 50 C is adjusted.Acetic anhydride time for adding 0.5h, acetic anhydride are added dropwise 50 DEG C of process control temp.Acetic anhydride drop finishes
Afterwards, reactant continues at reaction 10h at 55 DEG C.After reaction terminates, under the conditions of low vacuum recycling design to 110 DEG C of temperature, respectively
The mixed solution (reclaiming solution reusable edible) of recycling design petroleum ether, acetic anhydride and acetic acid.Residue first uses 30% hydrogen-oxygen
Change sodium solution to wash to system pH>7, it is washed with water to system pH=7.Steam solvent and residual moisture in system, product GC-MS
Testing result such as table 6：
Table 6
Claims (6)
1. a kind of method that utilization natural d-borneol prepares dextrorotation Bronyl acetate, it is characterised in that comprise the following steps：With
Natural d-borneol and acetic anhydride are raw material, and acetic anhydride and natural d-borneol are pressed the ratio 2 of the amount of material：1 is dosed to reaction
In solvent petroleum ether, natural d-borneol is 1 with the solid-liquid ratio of petroleum ether：10g/ml, contains P in reaction dissolvent2O5As catalysis
Agent, the consumption of catalyst is natural borneol quality 10%, and after natural d-borneol fully dissolves, adjustment reaction temperature is 75 DEG C,
Acetic anhydride time for adding 0.5h, aceticanhydride are added dropwise 75 DEG C of process control temp；After aceticanhydride drop finishes, reactant is continued at
10h；Reaction pressure is under condition of normal pressure；After reaction terminates, first washed to system pH with 30% sodium hydroxide solution>7, then use water
It is washed till system pH=7；Steam solvent and residual moisture in system.
2. a kind of method that utilization natural d-borneol prepares dextrorotation Bronyl acetate, it is characterised in that comprise the following steps：With
Natural d-borneol and acetic anhydride are raw material, and acetic anhydride and natural d-borneol are pressed the ratio 2 of the amount of material：1 is dosed to reaction
In solvent petroleum ether, natural d-borneol is 1 with the solid-liquid ratio of petroleum ether：10g/ml, contains P in reaction dissolvent2O5As catalysis
Agent, the consumption of catalyst is the 10% of natural borneol quality, and after raw material fully dissolves, adjustment system temperature is to 75 DEG C；Acetic anhydride
Time for adding 0.5h, acetic anhydride are added dropwise 75 DEG C of process control temp；After acetic anhydride drop finishes, reactant is continued at
6h；After reaction terminates, first washed to system pH with 30% sodium hydroxide solution>7, it is washed with water to system pH=7；Steam system
Middle solvent and residual moisture.
3. a kind of method that utilization natural d-borneol prepares dextrorotation Bronyl acetate, it is characterised in that comprise the following steps：With
Natural d-borneol and acetic anhydride are raw material, and acetic anhydride and natural d-borneol are pressed the ratio 2 of the amount of material：1 is dosed to reaction
In solvent petroleum ether, natural d-borneol is 1 with the solid-liquid ratio of petroleum ether：10g/ml, contains P in reaction dissolvent2O5As catalysis
Agent, the consumption of catalyst is the 10% of natural borneol quality, after raw material fully dissolves, adjusts 75 DEG C of system temperature；Aceticanhydride is added dropwise
Time 0.5h, aceticanhydride are added dropwise 75 DEG C of process control temp；After aceticanhydride drop finishes, reactant continues at reaction 6h at 75 DEG C；Reaction knot
Shu Hou, under the conditions of low vacuum, to 110 DEG C of temperature, the mixing for being separately recovered solvent petroleum ether, acetic anhydride and acetic acid is molten for recycling design
Liquid；Residue is first washed to system pH with 30% sodium hydroxide solution>7, it is washed with water to system pH=7；Steam molten in system
Agent and residual moisture.
4. a kind of method that utilization natural d-borneol prepares dextrorotation Bronyl acetate, it is characterised in that comprise the following steps：With
P2O5With H3PO4Mass ratio 1：10 are stirred well to solution clear under the conditions of 35 DEG C, prepare P2O5-H3PO4Composite catalyzing
Agent；Acetic anhydride and natural d-borneol, with natural d-borneol and acetic anhydride as raw material, are pressed the ratio 2 of the amount of material：1 is dosed to
In reaction dissolvent petroleum ether, natural d-borneol is 1 with the solid-liquid ratio of petroleum ether：10g/ml, contains P in reaction dissolvent2O5-
H3PO4Used as catalyst, the consumption of catalyst is the 10% of natural borneol quality to composite catalyst, after raw material borneol fully dissolves,
75 DEG C of system temperature of adjustment；Acetic anhydride time for adding 0.5h, acetic anhydride are added dropwise 75 DEG C of process control temp；After acetic anhydride drop finishes,
Reactant continues at reaction 6h at 75 DEG C；After reaction terminates, first washed to system pH with 30% sodium hydroxide solution>7, then use water
It is washed till system pH=7；Steam solvent and residual moisture in system.
5. a kind of method that utilization natural d-borneol prepares dextrorotation Bronyl acetate, it is characterised in that comprise the following steps：With
Natural d-borneol and acetic anhydride are raw material, add 1.84g P in 18.4g natural d-borneols2O5, then plus 184g petroleum ethers work
Reaction system solvent；Adjustment system temperature, starts 24.4g acetic anhydride is added dropwise to 75 DEG C after material is completely dissolved；Acetic anhydride drips
0.5h between the added-time, acetic anhydride are added dropwise 75 DEG C of process control system temperature.After aceticanhydride drop finishes, reactant is continued at
6h；After reaction terminates, first washed to system PH with 30% sodium hydroxide solution>7, it is washed with water to system PH=7；Steam system
Middle solvent and residual moisture.
6. a kind of method that utilization natural d-borneol prepares dextrorotation Bronyl acetate, it is characterised in that comprise the following steps：With
Natural d-borneol and acetic anhydride are raw material, and acetic anhydride and natural d-borneol are pressed the ratio 1 of the amount of material：1 is dosed to reaction
In solvent petroleum ether, natural d-borneol is 1 with the solid-liquid ratio of petroleum ether：15g/ml, contains P in reaction dissolvent2O5As catalysis
Agent, the consumption of catalyst is the 5% of natural borneol quality, after raw material fully dissolves, adjusts system temperature 50 C；Acetic anhydride is added dropwise
Time 0.5h, acetic anhydride are added dropwise 50 DEG C of process control temp；After acetic anhydride drop finishes, reactant continues at reaction 10h at 55 DEG C；Instead
After should terminating, under the conditions of low vacuum, recycling design is separately recovered the mixed of solvent petroleum ether, acetic anhydride and acetic acid to 110 DEG C of temperature
Close solution；Residue is first washed to system pH with 30% sodium hydroxide solution>7, it is washed with water to system pH=7；Steam system
Middle solvent and residual moisture.
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Inventor after: Yang Haikuan Inventor after: Wang Zhaoying Inventor after: Song Xiaochen Inventor after: Xu Haining Inventor after: Yu Lin Inventor after: Zeng Wei Inventor after: Xiong Zhenyu Inventor after: Zhang Ting Inventor after: Jiang Xiangmei Inventor after: Xiao fuming Inventor after: Dai Xiaoying Inventor after: Qiu Fengying Inventor after: Wu Yanfang Inventor after: Wang Xindong Inventor before: Yang Haikuan Inventor before: Song Xiaochen Inventor before: Xu Haining Inventor before: Yu Lin Inventor before: Zeng Wei Inventor before: Zhang Ting Inventor before: Jiang Xiangmei Inventor before: Xiao Fuming Inventor before: Dai Xiaoying Inventor before: Qiu Fengying Inventor before: Wu Yanfang Inventor before: Wang Xindong Inventor before: Wang Zhaoying |
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Effective date of registration: 20221102 Address after: 344800 Zone C, Jinxi Industrial Park, Fuzhou City, Jiangxi Province Patentee after: JIANGXI SPICE CHEMICAL INDUSTRIAL Co.,Ltd. Address before: Room 101, Scientific Research Building, Jiangxi Academy of Forestry Sciences, No. 1629, Fenglin West Avenue, Changbei District, Nanchang City, Jiangxi Province 330032 Patentee before: JIANGXI ACADEMY OF FORESTRY |