CN108822069A - A method of trienol is purified using chromatographic column - Google Patents
A method of trienol is purified using chromatographic column Download PDFInfo
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- CN108822069A CN108822069A CN201810599638.XA CN201810599638A CN108822069A CN 108822069 A CN108822069 A CN 108822069A CN 201810599638 A CN201810599638 A CN 201810599638A CN 108822069 A CN108822069 A CN 108822069A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
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Abstract
The present invention provides a kind of methods using chromatographic column purification trienol, and this approach includes the following steps：(1) the trienol crude product obtained after molecular distillation is selected, wherein triolefin phenol content is 30-70%；(2) column is filled：Stationary phase adsorbent is housed, stationary phase adsorbent is dipped in initial solvent in chromatographic column；(3) raw material is mixed with initial solvent, and the speed of 5%~10% upper prop material total amount is added to chromatographic column upper end with 30 DEG C~50 DEG C of temperature and per hour；(4) gradient elution is carried out to chromatographic column；(5) Fractional Collections are carried out to the material of elution；(6) product of each Fractional Collections, and the trienol that trienol component is merged to purify are evaporated under reduced pressure.Method provided by the invention is efficiently convenient, high financial profit, and the trienol purity is high of purification, overall process does not generate waste water, waste residue completely, is nearly free from exhaust gas after highly effective matched solvent recovery unit, hardly needs environmental protection facility processing.
Description
Technical field
The invention belongs to field of chemical engineering, and in particular to a method of trienol is purified using chromatographic column.
Background technique
Vitamin E (tocopherol) plays an important role in the different stages of growth of various animals, to reproduction, muscle, mind
Through and functional play of the systems such as immune be essential.Most effective ingredient is d- alpha tocopherol in vitamin E, activity
High, distribution is extensively, representative, and trienol has effect more stronger than d- alpha tocopherol, solid in anti-oxidant, anticancer, reduction gallbladder
Alcohol etc. is all better than d- alpha tocopherol.This is because trienol contains unsaturated terminal chain, can more effectively permeate in containing saturation
In the tissue of fatty-acid layer, to have extraordinary anti-oxidant and radicals scavenging efficiency, in addition, it there are also bio-compatibilities
Well, the advantages that safety is good, at low cost, can be widely applied in the industries such as beauty, medicine, has a vast market foreground.
The conventional method of trienol is purified, the first step is with Palm fatty acid distillates, rice bran oil deodorization distillate etc. one
The raw material containing trienol first carries out esterification or ester exchange reaction a bit, carries out molecular distillation later and trienol crude product is made, then
Trienol crude product is subjected to ion column or chromatographic column purification to obtain high-content trienol.The core process of this method is benefit
Trienol crude product is purified with ion column or chromatographic column, and after trienol is freed, ion column used and chromatographic column must
Need regenerate could be recycled, and the composite waste of a large amount of alkali waste waters and waste oil, subsequent environmental protection can be generated in regenerative process
It handles extremely difficult, and puts into larger, still can cause environmental pollution, it is both uneconomical or be unfavorable for environmental protection.
Summary of the invention
The purpose of the invention is to overcome the shortcomings of above-mentioned background technique, a kind of utilization chromatographic column purification trienol is provided
Method, this method is efficiently convenient, economic and environment-friendly, product high conversion efficiency, the trienol that is purified purity is high.
To achieve the object of the present invention, the present invention is included the following steps using the method for chromatographic column purification trienol：
(1) raw material is selected：The trienol crude product obtained after molecular distillation is selected, wherein triolefin phenol content is 30-70%；
(2) column is filled：Chromatography column diameter and height used is than being 1：8~10, it equipped with volume is chromatography cylinder in chromatographic column
The stationary phase adsorbent of product 30%~50%, the stationary phase adsorbent are dipped in initial solvent；
(3) upper prop：It is material quality by raw material and quality that quality is stationary phase adsorbent mass 3%~4% used
30%~60% initial solvent mixing, and with 30 DEG C~50 DEG C of temperature and per hour 5%~10% upper prop material total amount
Speed is added to chromatographic column upper end；
(4) it elutes：Gradient is carried out to chromatographic column with eluant, eluent with the speed of 20%~30% stationary phase adsorbent per hour
Elution keeps the elution time under the polarity to maintain 3~5 hours；
(5) it collects：70%-120% with stationary phase adsorbent mass used is that segmentation is segmented the material of elution
It collects；
(6) product post-processes：It is evaporated under reduced pressure the product of each Fractional Collections, and trienol component is merged up to purifying
Trienol.
In the present invention, the initial solvent can for petroleum ether, carbon tetrachloride, ether, ethyl acetate, n-butanol, acetone,
One of ethyl alcohol and methanol, such as petroleum ether.
In the present invention, the stationary phase adsorbent can be one of silica gel, aluminium oxide or quartz or a variety of mixing
Object.
In the present invention, the eluant, eluent can be petroleum ether, carbon tetrachloride, ether, ethyl acetate, n-butanol, acetone, second
Two or more of mixed solvents in alcohol, methanol.
Preferably, the eluant, eluent is petroleum ether and the mixed solvent of ethyl alcohol, the mixed solvent of petroleum ether and acetone, petroleum
The mixed solvent of ether and n-butanol, the mixed solvent of petroleum ether and ethyl acetate, petroleum ether and ethyl acetate and ethyl alcohol it is mixed
Bonding solvent.
In the present invention, obtained trienol purity is 95% or more in the step (6).
In the present invention, after material has eluted in chromatographic column in the step (5), cleaned with initial solvent, after cleaning
Vacuum distillation gained solvent can be recycled by shunting in gained solvent and step (6).
Gradient elution of the present invention is the ratio for changing various solvents in eluant, eluent, makes its polarity by weak to strong, shape
Polarity gradient, to elute to the different material in chromatographic column, every polarity for changing an eluant, eluent is kept under the polarity
Elution time maintain 3~5 hours.
Compared with prior art, the present invention has the following advantages：
1. the trienol purity is high obtained, high conversion efficiency, economic benefit are higher；
2. the present invention is in addition to the trienol of available high-purity, after acquired other same component merges in step (6)
Also the product of available high-purity；
3. overall process of the present invention does not chemically react, resulting product is all-natural product；
4. the solvent recovery unit that method of the invention can be highly effective matched, production cost are low；
5. method overall process of the invention does not generate waste water, waste residue completely, after highly effective matched solvent recovery unit almost
Exhaust gas is not generated, environmental protection facility processing is hardly needed, effect on environment is small.
Specific embodiment
In order to make the objectives, technical solutions, and advantages of the present invention clearer, with reference to embodiments, to the present invention
It is further elaborated.Additional aspect and advantage of the invention will be set forth in part in the description, partially will be under
Become obvious in the description in face, or practice through the invention is recognized.It is only used to explain this hair it should be appreciated that being described below
It is bright, it is not intended to limit the present invention.
To achieve the object of the present invention, the present invention is included the following steps using the method for chromatographic column purification trienol：
(1) raw material is selected：The trienol crude product obtained after molecular distillation is selected, wherein triolefin phenol content is 30-70%；
(2) column is filled：Chromatography column diameter and height used is than being 1：8~10, it equipped with volume is chromatography cylinder in chromatographic column
The stationary phase adsorbent of product 30%~50%, the stationary phase adsorbent are dipped in initial solvent；
(3) upper prop：It is material quality by raw material and quality that quality is stationary phase adsorbent mass 3%~4% used
30%~60% initial solvent mixing, and with 30 DEG C~50 DEG C of temperature and per hour 5%~10% upper prop material total amount
Speed is added to chromatographic column upper end；
(4) it elutes：Gradient is carried out to chromatographic column with eluant, eluent with the speed of 20%~30% stationary phase adsorbent per hour
Elution keeps the elution time under the polarity to maintain 3~5 hours；
(5) it collects：70%-120% with stationary phase adsorbent mass used is that segmentation is segmented the material of elution
It collects；
(6) product post-processes：It is evaporated under reduced pressure the product of each Fractional Collections, and trienol component is merged up to purifying
Trienol.
In the present invention, the initial solvent can for petroleum ether, carbon tetrachloride, ether, ethyl acetate, n-butanol, acetone,
One of ethyl alcohol and methanol, such as petroleum ether.
In the present invention, the stationary phase adsorbent can be one of silica gel, aluminium oxide or quartz or a variety of mixing
Object.
In the present invention, the eluant, eluent can be petroleum ether, carbon tetrachloride, ether, ethyl acetate, n-butanol, acetone, second
Two or more of mixed solvents in alcohol, methanol.
Preferably, the eluant, eluent is petroleum ether and the mixed solvent of ethyl alcohol, the mixed solvent of petroleum ether and acetone, petroleum
The mixed solvent of ether and n-butanol, the mixed solvent of petroleum ether and ethyl acetate, petroleum ether and ethyl acetate and ethyl alcohol it is mixed
Bonding solvent.
In the present invention, obtained trienol purity is 95% or more in the step (6).
In the present invention, after material has eluted in chromatographic column in the step (5), cleaned with initial solvent, after cleaning
Vacuum distillation gained solvent can be recycled by shunting in gained solvent and step (6).
Gradient elution of the present invention is the ratio for changing various solvents in eluant, eluent, makes its polarity by weak to strong, shape
Polarity gradient, to elute to the different material in chromatographic column, every polarity for changing an eluant, eluent is kept under the polarity
Elution time maintain 3~5 hours.
Term "comprising" used herein, " comprising ", " having ", " containing " or its any other deformation, it is intended that covering
Non-exclusionism includes.For example, composition, step, method, product or device comprising listed elements are not necessarily limited to those and want
Element, but may include not expressly listed other elements or such composition, step, method, product or device it is intrinsic
Element.
Equivalent, concentration or other values or parameter are excellent with range, preferred scope or a series of upper limit preferred values and lower limit
When the Range Representation that choosing value limits, this should be understood as specifically disclosing by any range limit or preferred value and any range
Any pairing of lower limit or preferred value is formed by all ranges, regardless of whether the range separately discloses.For example, when open
When range " 1 to 5 ", described range should be interpreted as including range " 1 to 4 ", " 1 to 3 ", " 1 to 2 ", " 1 to 2 and 4 to
5 ", " 1 to 3 and 5 " etc..When numberical range is described herein, unless otherwise stated, otherwise the range is intended to include its end
Value and all integers and score in the range.
Indefinite article "an" before element or component of the present invention (goes out the quantitative requirement of element or component with "one"
Occurrence number) unrestriction.Therefore "one" or "an" should be read as including one or at least one, and singular
Element or component also include plural form, unless the quantity obviously only refers to singular.
Moreover, technical characteristic involved in each embodiment of the present invention as long as they do not conflict with each other can
To be combined with each other.
Embodiment 1
Column diameter 1m, height 9m are chromatographed, chromatography column volume is 7.065m3, stationary phase adsorbent silica gel is filled in chromatographic column
3.5m3, 1500 ㎏ of quality, and be dipped in initial solvent petroleum ether；Take 50 ㎏ (its of trienol crude product obtained after molecular distillation
Middle triolefin phenol content be 35%), mixed with 25 ㎏ petroleum ethers, and with 35 DEG C of temperature and per hour the speed of 7 ㎏ from chromatographic column
Upper end is added；Gradient elution, elution time dimension are carried out to chromatographic column with 400 ㎏ speed eluent petroleum ethers per hour, ethyl alcohol
It holds 4 hours, Fractional Collections is carried out to elution material using 1200 ㎏ as number of fragments；It is evaporated under reduced pressure the product of each Fractional Collections, and
Trienol component is merged to the trienol for being 95.1% to get purity；After material has eluted in chromatographic column, initial solvent is used
Petroleum ether is cleaned, after cleaning gained solvent and product post-processing step in vacuum distillation gained solvent can be by shunting back
It receives and utilizes.
Embodiment 2
Column diameter 1m, height 9m are chromatographed, chromatography column volume is 7.065m3, stationary phase adsorbent aluminium oxide is filled in chromatographic column
3.5m3, 3000 ㎏ of quality, and be dipped in initial solvent petroleum ether；Take 100 ㎏ of trienol crude product obtained after molecular distillation
(wherein triolefin phenol content be 40%), mixed with 50 ㎏ petroleum ethers, and with 35 DEG C of temperature and per hour the speed of 10 ㎏ from layer
Column upper end is analysed to be added；Gradient elution carried out to chromatographic column with 700 ㎏ speed eluent petroleum ethers per hour, acetone, when elution
Between maintain 5 hours, using 2500 ㎏ be number of fragments to elution material carry out Fractional Collections；It is evaporated under reduced pressure the production of each Fractional Collections
Product, and trienol component is merged to the trienol for being 95.06% to get purity；After material has eluted in chromatographic column, with first
Beginning solvent petroleum ether is cleaned, after cleaning gained solvent and product post-processing step in vacuum distillation gained solvent can pass through
It shunts and recycles.
Embodiment 3
Column diameter 1m, height 9m are chromatographed, chromatography column volume is 7.065m3, dress stationary phase adsorbent quartz in chromatographic column
3.5m3, 5600 ㎏ of quality, and be dipped in initial solvent petroleum ether；Take 200 ㎏ of trienol crude product obtained after molecular distillation
(wherein triolefin phenol content be 45%), mixed with 100 ㎏ petroleum ethers, and with 45 DEG C of temperature and per hour the speed of 20 ㎏ from layer
Column upper end is analysed to be added；Gradient elution is carried out to chromatographic column with 1400 ㎏ speed eluent petroleum ethers, n-butanol per hour, is eluted
Time maintains 5 hours, carries out Fractional Collections to elution material using 4000 ㎏ as number of fragments；It is evaporated under reduced pressure the production of each Fractional Collections
Product, and trienol component is merged to the trienol for being 95.2% to get purity；After material has eluted in chromatographic column, with first
Beginning solvent petroleum ether is cleaned, after cleaning gained solvent and product post-processing step in vacuum distillation gained solvent can pass through
It shunts and recycles.
Embodiment 4
Column diameter 1m, height 9m are chromatographed, chromatography column volume is 7.065m3, stationary phase adsorbent silica gel is filled in chromatographic column
(volume ratio 1 is mixed with aluminium oxide：1)3.5m3, 2100 ㎏ of quality, and be dipped in initial solvent petroleum ether；It is obtained after taking molecular distillation
80 ㎏ of trienol crude product (wherein triolefin phenol content be 50%) arrived, mix with 40 ㎏ petroleum ethers, and with 50 DEG C of temperature with
The speed of 10 ㎏ is added from chromatographic column upper end per hour；With 500 ㎏ speed eluent petroleum ethers, ethyl acetate per hour to layer
It analyses column and carries out gradient elution, elution time maintains 4 hours, carries out Fractional Collections to elution material using 2000 ㎏ as number of fragments；
It is evaporated under reduced pressure the product of each Fractional Collections, and trienol component is merged, the triolefin that purity is 95.25% can be obtained
Phenol；It after material has eluted in chromatographic column, is cleaned with initial solvent petroleum ether, gained solvent and product post-processing step after cleaning
Vacuum distillation gained solvent can be recycled by shunting in rapid.
Embodiment 5
Column diameter 0.5m, height 5m are chromatographed, chromatography column volume is 0.981m3, stationary phase adsorbent silicon is filled in chromatographic column
Glue mixes (volume ratio 1 with quartz：1)0.39m3, 390 ㎏ of quality, and be dipped in initial solvent petroleum ether；It is obtained after taking molecular distillation
14 ㎏ of trienol crude product (wherein triolefin phenol content is 60%) arrived, mixes with 7 ㎏ petroleum ethers, and with 50 DEG C of temperature and often
The speed of 2 ㎏ of hour is added from chromatographic column upper end；With 100 ㎏ speed eluent petroleum ethers per hour, ethyl alcohol to chromatographic column into
Row gradient elution, elution time maintain 5 hours, carry out Fractional Collections to elution material using 400 ㎏ as number of fragments；Vacuum distillation
The product of each Fractional Collections, and trienol component is merged, the trienol that purity is 95.3% can be obtained；In chromatographic column
It after material has eluted, is cleaned with initial solvent petroleum ether, depressurizes steaming in gained solvent and product post-processing step after cleaning
Evaporating gained solvent can be recycled by shunting.
Embodiment 6
Column diameter 0.5m, height 5m are chromatographed, chromatography column volume is 0.981m3, stationary phase adsorbent oxygen is filled in chromatographic column
Change aluminium and mixes (volume ratio 1 with quartz：1)0.39m3, 468 ㎏ of quality, and be dipped in initial solvent petroleum ether；After taking molecular distillation
Obtained 16 ㎏ of trienol crude product (wherein triolefin phenol content be 68%), mix with 8 ㎏ petroleum ethers, and with 45 DEG C of temperature with
The speed of 2 ㎏ is added from chromatographic column upper end per hour；With 120 ㎏ speed eluent petroleum ethers, ethyl alcohol per hour to chromatographic column
Gradient elution is carried out, elution time maintains 4 hours, carries out Fractional Collections to elution material using 450 ㎏ as number of fragments；Decompression is steamed
The product of each Fractional Collections is evaporated, and trienol component is merged, the trienol that purity is 95.2% can be obtained；Chromatographic column
It after middle material has eluted, is cleaned with initial solvent petroleum ether, is depressurized in gained solvent and product post-processing step after cleaning
Distillation gained solvent can be recycled by shunting.
Embodiment 7
Column diameter 0.5m, height 5m are chromatographed, chromatography column volume is 0.981m3, stationary phase adsorbent silicon is filled in chromatographic column
Glue 0.39m3, 170 ㎏ of quality, and be dipped in initial solvent petroleum ether；Take 6 ㎏ of trienol crude product obtained after molecular distillation
(wherein triolefin phenol content be 65%), mixed with 3 ㎏ petroleum ethers, and with 40 DEG C of temperature and per hour the speed of 0.6 ㎏ from layer
Column upper end is analysed to be added；Gradient elution, elution time are carried out to chromatographic column with 40 ㎏ speed eluent petroleum ethers, ethyl alcohol per hour
It maintains 4.5 hours, Fractional Collections is carried out to elution material using 180 ㎏ as number of fragments；It is evaporated under reduced pressure the product of each Fractional Collections,
And merge trienol component, the trienol that purity is 95.1% can be obtained；After material has eluted in chromatographic column, with first
Beginning solvent petroleum ether is cleaned, after cleaning gained solvent and product post-processing step in vacuum distillation gained solvent can pass through
It shunts and recycles.
Embodiment 8
Column diameter 0.5m, height 5m are chromatographed, chromatography column volume is 0.981m3, stationary phase adsorbent silicon is filled in chromatographic column
Glue 0.39m3, 170 ㎏ of quality, and be dipped in initial solvent petroleum ether；Take 6 ㎏ of trienol crude product obtained after molecular distillation
(wherein triolefin phenol content be 65%), mixed with 3 ㎏ petroleum ethers, and with 40 DEG C of temperature and per hour the speed of 0.6 ㎏ from layer
Column upper end is analysed to be added；Gradient is carried out to chromatographic column with 40 ㎏ speed eluent petroleum ethers, ethyl acetate, ethyl alcohol per hour to wash
De-, elution time maintains 4.5 hours, carries out Fractional Collections to elution material using 120 ㎏ as number of fragments；It is evaporated under reduced pressure each segmentation
The product of collection, and trienol component is merged, the trienol that purity is 95.1% can be obtained；Material is washed in chromatographic column
It after having taken off, is cleaned with initial solvent petroleum ether, is evaporated under reduced pressure gained in gained solvent and product post-processing step after cleaning
Solvent can be recycled by shunting.
As it will be easily appreciated by one skilled in the art that the foregoing is merely illustrative of the preferred embodiments of the present invention, not to
The limitation present invention, any modifications, equivalent substitutions and improvements made within the spirit and principles of the present invention should all include
Within protection scope of the present invention.
Claims (8)
1. a kind of method using chromatographic column purification trienol, which is characterized in that this approach includes the following steps：
(1) raw material is selected：The trienol crude product obtained after molecular distillation is selected, wherein triolefin phenol content is 30-70%；
(2) column is filled：Chromatography column diameter and height used is than being 1：8~10, it equipped with volume is chromatography column volume in chromatographic column
30%~50% stationary phase adsorbent, the stationary phase adsorbent are dipped in initial solvent；
(3) upper prop：By raw material and quality that quality is stationary phase adsorbent mass 3%~4% used be material quality 30%~
60% initial solvent mixing, and the speed of 5%~10% upper prop material total amount adds with 30 DEG C~50 DEG C of temperature and per hour
Enter to chromatographic column upper end；
(4) it elutes：Gradient elution is carried out to chromatographic column with eluant, eluent with the speed of 20%~30% stationary phase adsorbent per hour,
The elution time under the polarity is kept to maintain 3~5 hours；
(5) it collects：70%-120% with stationary phase adsorbent mass used is that segmentation carries out Fractional Collections to the material of elution；
(6) product post-processes：It is evaporated under reduced pressure the product of each Fractional Collections, and trienol component is merged into three up to purification
Alkene phenol.
2. the method according to claim 1 using chromatographic column purification trienol, which is characterized in that the initial solvent is
One of petroleum ether, carbon tetrachloride, ether, ethyl acetate, n-butanol, acetone, ethyl alcohol and methanol.
3. the method according to claim 2 using chromatographic column purification trienol, which is characterized in that the initial solvent is
Petroleum ether.
4. the method according to claim 1 using chromatographic column purification trienol, which is characterized in that the stationary phase absorption
Agent is one of silica gel, aluminium oxide or quartz or a variety of mixtures.
5. the method according to claim 1 using chromatographic column purification trienol, which is characterized in that the eluant, eluent is stone
Oily ether, carbon tetrachloride, ether, ethyl acetate, n-butanol, acetone, ethyl alcohol, two or more of mixed solvents in methanol.
6. the method according to claim 5 using chromatographic column purification trienol, which is characterized in that the eluant, eluent is stone
The mixed solvent of oily ether and ethyl alcohol, the mixed solvent of petroleum ether and acetone, the mixed solvent of petroleum ether and n-butanol, petroleum ether and
Mixed solvent, petroleum ether and the ethyl acetate of ethyl acetate and the mixed solvent of ethyl alcohol.
7. the method according to claim 1 using chromatographic column purification trienol, which is characterized in that in the step (6)
Obtained trienol purity is 95% or more.
8. the method according to claim 1 using chromatographic column purification trienol, which is characterized in that in the step (5)
It after material has eluted in chromatographic column, is cleaned with initial solvent, is evaporated under reduced pressure gained in gained solvent and step (6) after cleaning
Solvent is recycled by shunting.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810599638.XA CN108822069A (en) | 2018-06-13 | 2018-06-13 | A method of trienol is purified using chromatographic column |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810599638.XA CN108822069A (en) | 2018-06-13 | 2018-06-13 | A method of trienol is purified using chromatographic column |
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| CN108822069A true CN108822069A (en) | 2018-11-16 |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632210A (en) * | 2015-11-03 | 2017-05-10 | 浙江医药股份有限公司新昌制药厂 | Method for preparing high-purity tocotrienols from tocols through separation and purification |
-
2018
- 2018-06-13 CN CN201810599638.XA patent/CN108822069A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632210A (en) * | 2015-11-03 | 2017-05-10 | 浙江医药股份有限公司新昌制药厂 | Method for preparing high-purity tocotrienols from tocols through separation and purification |
Non-Patent Citations (2)
| Title |
|---|
| 何东平等: "《米糠加工技术》", 30 April 2014, 中国轻工业出版社 * |
| 叶彦春等: "《有机化学实验》", 31 January 2018, 北京理工大学出版社 * |
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