CN108440689B - Xanthenes alcohol modified resin and its preparation method and application - Google Patents
Xanthenes alcohol modified resin and its preparation method and application Download PDFInfo
- Publication number
- CN108440689B CN108440689B CN201810475169.0A CN201810475169A CN108440689B CN 108440689 B CN108440689 B CN 108440689B CN 201810475169 A CN201810475169 A CN 201810475169A CN 108440689 B CN108440689 B CN 108440689B
- Authority
- CN
- China
- Prior art keywords
- resin
- oxoxanthone
- modified resin
- hydroxyl
- wine
- 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.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/26—Removing halogen atoms or halogen-containing groups from the molecule
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Analytical Chemistry (AREA)
- Non-Alcoholic Beverages (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
A kind of xanthenes alcohol modified resin of the present invention and its preparation method and application; hydroxyl Oxoxanthone and Anhydrous potassium carbonate are uniformly mixed by this method first; mixture is obtained, mixture is then dissolved in dimethyl acetamide, then under protection of argon gas; it is stirred to react; then macromolecule resin is added to stir evenly, the reaction was continued, filters after being cooled to room temperature; washing, vacuum drying, obtain solid matter；Solid matter, sodium borohydride, anhydrous lithium chloride are dissolved in tetrahydrofuran and are uniformly mixed, is reacted at room temperature, is filtered after being cooled to room temperature, is washed to get xanthenes alcohol modified resin is arrived.The present invention can remove already present EC in wine, can also remove the precursor substance urea of EC in wine, and urea is prevented to be converted into new EC in drinks drink storage, to ensure the security quality of inebriant.
Description
Technical field
The present invention relates to modified resins, and in particular to a kind of xanthenes alcohol modified resin and its preparation method and application.
Background technique
Generally existing urethanes (EC) in alcoholic beverage, especially EC content is higher in yellow rice wine.EC is proved to have
There are carcinogenesis, international cancer research institution's specialists meeting (International Agency for Research on
Cancer the carcinogenic risk of EC) is classified as 2A class carcinogenic substance (the higher substance of a possibility that human carcinogen).2002, connection
EC content must not exceed 20 μ gL in He Guo food and agricultural organization regulation food-1.Investigation display China's yellow rice wine in EC contents level compared with
Height, EC average content is about 160 μ gL in commercially available yellow rice wine-1Left and right (Fu et al 2010, Wu et al 2012).Beverage wine
Storage time it is longer, EC content is higher.Therefore EC content in alcoholic beverage is reduced, to guarantee people's health meaning weight
Greatly.
The study found that EC is mainly to pass through urea and ethanol synthesis generation in drinks drink.Therefore the urine in removal wine
Element is the important channel for reducing EC content in wine.At present there is the main method of urea content in control wine: reducing and urinates in supplementary material
Cellulose content, breeding high-yield urea saccharomyces cerevisiae, addition urase decompose the urea in wine liquid；Pass through the direct Adsorption urine of material
Element.But all there is its shortcoming in above method, such as refine liquor-making raw material, same although urea content in raw material can be reduced
When will cause the passage of rice nutrition ingredient, while thering is new urea largely to be generated again in subsequent fermentations.It is preferred that low
Although produce urea yellow wine yeast can reduce urea content in wine, due to use different saccharomyces cerevisiaes, liquor output and
Flavor changes very big (2011, the Chen Sheng such as Song Xulei 2012, Zhu Xuya 2012)；Although urase can effectively catalyzing urea degrade,
For urase in application, due to being influenced by ethyl alcohol in Wine drink, efficiency becomes extremely low, or even loses enzymatic activity (Wu Zhaohui
2010)；Although EC degrading enzyme can directly decompose EC, the presence of the organic matters such as acidic environment condition and ethyl alcohol can make zymoprotein
Deactivation；Urea is removed by physical absorption using adsorbent material, it is easy to operate.
But report that the material of test lacks specificity to the absorption of urea so far, effect is unstable, while to wine
Flavor has an impact.Therefore research and develop selective adsorbent material remove EC in drinks drink and urea have it is bright before
Scape.
Summary of the invention
It is an object of the invention to overcome the deficiencies of the prior art and provide a kind of xanthenes alcohol modified resin and its preparation sides
Method and application.To which EC and its precursor substance urea to be adsorbed on resin by the chemical reaction of selectivity, then lead to
Urea and EC in wine can be reduced by crossing simple filtration.This method can remove already present EC in wine, can also remove in wine
The precursor substance urea of EC prevents urea to be converted into new EC in drinks drink storage, to ensure inebriant
Security quality.
To achieve the above object, a kind of xanthenes alcohol modified resin designed by the present invention, the structural formula of the modified resin are as follows:
Wherein, P is macromolecule resin,
Further, the P is merrifield resin, the structural formula of the merrifield resin are as follows:
And the structural formula of the xanthenes alcohol modified resin are as follows:
Still further, any one in the structural formula difference following structural formula of the modified resin:
The method for preparing above-mentioned xanthenes alcohol modified resin, comprising the following steps:
1) 1 part of hydroxyl Oxoxanthone, 0.5~3 part of Anhydrous potassium carbonate, 0.2~3 part of macromolecule are weighed by above-mentioned weight fraction ratio
Resin reaction, obtained solid are further reacted with 0.2~1 part of sodium borohydride and 0.2~1 part of anhydrous lithium chloride；
2) hydroxyl Oxoxanthone and Anhydrous potassium carbonate are uniformly mixed first, obtain mixture, mixture is then dissolved in two
Then under protection of argon gas methylacetamide is 70~90 DEG C in temperature and is stirred to react 3~5h, macromolecule resin is then added
It stirs evenly, the reaction was continued 20~30h is filtered after being cooled to room temperature, washed, is dried in vacuo, obtain solid matter；
3) solid matter, sodium borohydride, anhydrous lithium chloride are dissolved in tetrahydrofuran and are uniformly mixed, at room temperature
10~16h is reacted, 35~45 DEG C of 20~48h of reaction is then heated to, is filtered after being cooled to room temperature, is washed to get xanthenes alcohol is arrived
Modified resin.
Preferably, the macromolecule resin is merrifield resin.(English name: Merrifield
Resin, Chinese nickname: Chloromethyl polystyrene；1-chloro-4-methyl-benzene-divinyl benzene styrene copolymer)
Preferably, the hydroxyl Oxoxanthone be 1- hydroxyl Oxoxanthone, 2- hydroxyl Oxoxanthone, 3- hydroxyl Oxoxanthone and
Any one in 4- hydroxyl Oxoxanthone.
The present invention provides a kind of application of above-mentioned xanthenes alcohol modified resin in absorption EC and urea.
The application method: xanthenes alcohol modified resin being added into wine, is stirred to react under room temperature, and centrifugation obtains supernatant
Liquid；
Wherein, wine and xanthenes alcohol modified resin mass ratio are 24~96:1.
Further, the wine is yellow rice wine.
Beneficial effects of the present invention:
Xanthenes alcohol modified resin of the present invention has the function of while reducing EC and its precursor urea in inebriant, in this way
New EC is no longer generated during long-term storage convenient for drinks, to ensure wine safety in storage.
Xanthenes alcohol modified resin of the invention simultaneously uses simply, by mixing wine with xanthenes alcohol modified resin, simply
Filtering can be realized, or wine is passed through the pillar equipped with the resin.
Detailed description of the invention
Fig. 1 is the bonding reaction figure of Oxoxanthone and Merrifield resin in Examples 1 to 4；
Wherein, when Oxoxanthone is divided into 1- hydroxyl Oxoxanthone, 2- hydroxyl Oxoxanthone, 3- hydroxyl Oxoxanthone and 4- hydroxyl xanthenes
Ketone；Xanthone-1-O-P, Xanthone-2-O-P, Xanthone-3-O-P and Xanthone-4-O-P is prepared；
Fig. 2 is the reduction reaction figure that Oxoxanthone-Merrifield is bonded resin in embodiment 5~8；
Wherein, when Oxoxanthone is divided into 1- hydroxyl Oxoxanthone, 2- hydroxyl Oxoxanthone, 3- hydroxyl Oxoxanthone and 4- hydroxyl xanthenes
Ketone；Xanthydrol-1-O-P, Xanthydrol-2-O-P, Xanthydrol-3-O-P and Xanthydrol-4- is prepared
O-P；
The FT-IR that Fig. 3 is Xanthone-1-O-P schemes；
The FT-IR that Fig. 4 is Xanthone-2-O-P schemes；
The FT-IR that Fig. 5 is Xanthone-3-O-P schemes；
The FT-IR that Fig. 6 is Xanthone-4-O-P schemes；
The FT-IR that Fig. 7 is xanthenes alcohol modified resin Xanthydrol-1-O-P schemes；
The FT-IR that Fig. 8 is xanthenes alcohol modified resin Xanthydrol-2-O-P schemes；
The FT-IR that Fig. 9 is xanthenes alcohol modified resin Xanthydrol-3-O-P schemes；
The FT-IR that Figure 10 is xanthenes alcohol modified resin Xanthydrol-4-O-P schemes；
Specific embodiment
The present invention is described in further detail in the following with reference to the drawings and specific embodiments, so as to those skilled in the art
Understand.
Embodiment 1
1- hydroxyl Oxoxanthone is bonded (Xanthone-1-O-P) with merrifield resin
It takes 1.6g 1- hydroxyl Oxoxanthone in 150mL twoport flask, adds 1.1g Anhydrous potassium carbonate, add 20mL dimethylacetamide
Amine makees solvent, under argon gas protection after 80 DEG C are stirred to react 4h, by 0.75g merrifield resin and 25mL dimethylacetamide
Amine injects flask after mixing, and the reaction was continued stops reaction afterwards for 24 hours, filters after being cooled to room temperature, and successively uses 30mL methanol, and 50mL is super
Pure water, 30mL methanol wash respectively, solid vacuum drying.
Embodiment 2
2- hydroxyl Oxoxanthone is bonded (Xanthone-2-O-P) with merrifield resin
It takes 1.6g 2- hydroxyl Oxoxanthone in 150mL twoport flask, adds 3.3g Anhydrous potassium carbonate, add 20mL dimethylacetamide
Amine makees solvent, under argon gas protection after 70 DEG C are stirred to react 3h, by 1.5g merrifield resin and 25mL dimethyl acetamide
Flask is injected after mixing, stops reaction after the reaction was continued 20h, filters after being cooled to room temperature, successively uses 30mL methanol, and 50mL is ultrapure
Water, 30mL methanol wash respectively, solid vacuum drying.
Embodiment 3
3- hydroxyl Oxoxanthone is bonded (Xanthone-3-O-P) with merrifield resin
It takes 1.6g 3- hydroxyl Oxoxanthone in 150mL twoport flask, adds 2.2g Anhydrous potassium carbonate, add 20mL dimethylacetamide
Amine makees solvent, under argon gas protection after 90 DEG C are stirred to react 3h, by 4.8g merrifield resin and 25mL dimethyl acetamide
Flask is injected after mixing, stops reaction after the reaction was continued 30h, filters after being cooled to room temperature, successively uses 30mL methanol, and 50mL is ultrapure
Water, 30mL methanol wash respectively, solid vacuum drying.
Embodiment 4
4- hydroxyl Oxoxanthone is bonded (Xanthone-4-O-P) with merrifield resin
It takes 1.6g 4- hydroxyl Oxoxanthone in 150mL twoport flask, adds 4.8g Anhydrous potassium carbonate, add 20mL dimethylacetamide
Amine makees solvent and mixes 1g merrifield resin and 25mL dimethyl acetamide under argon gas protection after 80 DEG C are stirred to react 4h
Flask is injected after even, is stopped reaction after the reaction was continued 30h, is filtered after being cooled to room temperature, successively use 30mL methanol, 50mL is ultrapure
Water, 30mL methanol wash respectively, solid vacuum drying.
Embodiment 5
The preparation of xanthenes alcohol -1-O-merrifield resin (Xanthydrol-1-O-P)
Obtained resin 1g adds 0.34g sodium borohydride and the anhydrous chlorine of 0.39g in 100mL single-necked flask in Example 1
Change lithium, 25mL tetrahydrofuran after reacting at room temperature 12h, is warming up to 40 DEG C of reaction 48h and stops reaction, filter after being cooled to room temperature, Gu
Body is successively washed with 30mL methanol, 50mL ultrapure water, 30mL methanol, and obtained solid is xanthenes alcohol modified resin remodeling resin
Xanthydrol-1-O-P。
Embodiment 6
The preparation of xanthenes alcohol -2-O-merrifield resin (Xanthydrol-2-O-P)
Obtained resin 1g adds 1g sodium borohydride and 1g anhydrous lithium chloride in 100mL single-necked flask in Example 2,
25mL tetrahydrofuran after reacting at room temperature 12h, is warming up to 40 DEG C of reaction 20h and stops reaction, filter after being cooled to room temperature, solid is first
It is washed afterwards with 30mL methanol, 50mL ultrapure water, 30mL methanol, obtained solid is xanthenes alcohol modified resin remodeling resin
Xanthydrol-2-O-P。
Embodiment 7
The preparation of xanthenes alcohol -3-O-merrifield resin (Xanthydrol-3-O-P)
Obtained resin 1g adds 0.8g sodium borohydride and the anhydrous chlorination of 0.6g in 100mL single-necked flask in Example 3
Lithium, 25mL tetrahydrofuran after reacting at room temperature 10h, are warming up to 40 DEG C of reaction 20h and stop reaction, filter after being cooled to room temperature, solid
It is successively washed with 30mL methanol, 50mL ultrapure water, 30mL methanol, obtained solid is xanthenes alcohol modified resin remodeling resin
Xanthydrol-3-O-P。
Embodiment 8
The preparation of xanthenes alcohol -4-O-merrifield resin (Xanthydrol-4-O-P)
Obtained resin 1g adds 0.2g sodium borohydride and the anhydrous chlorination of 0.2g in 100mL single-necked flask in Example 4
Lithium, 25mL tetrahydrofuran after reacting at room temperature 16h, are warming up to 40 DEG C of reaction 48h and stop reaction, filter after being cooled to room temperature, solid
It is successively washed with 30mL methanol, 50mL ultrapure water, 30mL methanol, obtained solid is xanthenes alcohol modified resin remodeling resin
Xanthydrol-4-O-P。
Embodiment 9
Removal of the xanthenes alcohol modified resin to EC and urea in yellow rice wine analog sample
Weigh respectively each 0.1g of xanthenes alcohol modified resin (Xanthydrol-1-O-P, Xanthydrol-2-O-P,
Xanthydrol-3-O-P, Xanthydrol-4-O-P) in 10mL plastic centrifuge tube, 1.2mL is then respectively adding containing 100 μ
Mol/L EC or 100 μm of ol/L Urea yellow rice wine analog sample (6.0g lactic acid is weighed to be dissolved in the ethanol water of 1L 20%,
The solution is yellow rice wine analog sample), stop reaction after stirring 12h at room temperature, 8000r/min is centrifuged 5min, takes supernatant 600
μ L detects unreacted EC/Urea (Abreu 2005) in solution according to literature method HPLC-FLD.
Control group is the yellow rice wine analog sample that resin treatment is not added.
Experimental result is as shown in table 1 below
Removal rate of the 1 xanthenes alcohol modified resin of table to EC and Urea in yellow rice wine analog sample
Note: a): EC concentration is 100 μm of ol/L；B): Urea concentration is 100 μm of ol/L；The matter of resin and yellow rice wine analog sample
Amount is than being 1:12；Adsorption time 12h.
Xanthydrol-4-O-P is most strong to the removal ability of EC and Urea as can be seen from the table.It is to yellow rice wine analog sample
Middle EC removal rate is 61%, and the removal rate to Urea is 59%.
Embodiment 10
Removal of the Xanthydrol-4-O-P to EC and Urea in true yellow rice wine
Xanthydrol-4-O-P resin 0.05g is weighed in 10mL plastic centrifuge tube, 1.2mL yellow rice wine sample is then added
(through detecting, the sample itself 3.43 μm of ol/L containing EC, 86.70 μm of ol/L containing Urea) stops instead after stirring 12h at room temperature
Answer, 8000r/min be centrifuged 5min, take 600 μ L supernatants, according to literature method with HPLC-FLD detect solution in it is unreacted
EC/Urea(Abreu 2005)。
After Xanthydrol-4-O-P is handled, EC removal rate is 65.9%；Urea removal rate is 66.6%.China's export
Yellow rice wine require EC be no more than 100 μ g/L (1.12 μm of ol/L).And after the processing of xanthenes alcohol modified resin, brand yellow rice wine EC
Content is 1.17 μm of ol/L, can satisfy export requirement.
Embodiment 11
Removal of the Xanthydrol-4-O-P to EC and Urea in true yellow rice wine
Weigh Xanthydrol-4-O-P resin 0.5g (high 10cm, diameter 1cm) in the glass column of belt switch, then plus
Enter 12mL yellow rice wine sample (through detecting, the sample itself 3.43 μm of ol/L containing EC, 86.70 μm of ol/L containing Urea), open knob,
It allows yellow rice wine to ooze, controls 1 drop/sec of flow velocity, collect the yellow rice wine of outflow, sample, and examined according to literature method with HPLC-FLD
Survey unreacted EC/Urea (Abreu 2005) in solution.
After treatment by using the treatment method, EC removal rate is 63.8%；Urea removal rate is 64.2%.
Embodiment 12
Removal of the Xanthydrol-4-O-P to EC and Urea in the yellow rice wine sample of addition EC/Urea
0.05g Xanthydrol-4-O-P is weighed in 10mL plastic centrifuge tube, is separately added into 1.2mL, 2.4mL and 4.8mL
Add the yellow rice wine of EC (3.0 μm of ol/L, 6.0 μm of ol/L and 12.0 μm of ol/L) or Urea (108.0 μm of ol/L and 500.0 μm of ol/L)
Solution is stirred to react at room temperature, is stopped reaction after 12h and is taken 600 μ L supernatants after 8000r/min is centrifuged 5min, in solution not
The EC/Urea of reaction is tested and analyzed (Abreu 2005) with HPLC-FLD by literature method.
Table 2 is the removal effect of resin after adding EC, as seen from table, when EC addition concentration is 3 μm of ol/L, resin and yellow rice wine
Mass ratio when being 1:24, be 62.24% to the removal rate of EC；When the mass ratio of resin and yellow rice wine is higher than 1:48, to EC and
The removal rate of Urea maintains 62% or so；When the mass ratio of resin and yellow rice wine is 1:96, to addition 3,6,12 μm of ol/ of EC concentration
It is respectively 51.36%, 47.0%, 36.61% to EC removal rate for the yellow rice wine of L；And Urea contained by yellow rice wine itself is gone
Except rate is respectively 39.76%, 35.64%, 35.24%.
Removal rate of 2 Xanthydrol-4-O-P of table to the true yellow rice wine sample of addition EC
Note: a): the concentration containing EC itself is 3.43 μm of ol/L in this yellow rice wine, the concentration containing Urea itself is 86.70 μ
mol/L；The Adsorption time is 12h；The removal rate (%) of A:EC；The removal rate (%) of B:Urea
Table 3 is the application effect of resin after adding Urea, as seen from table, when the concentration for additionally adding Urea in yellow rice wine is
When 108 μm of ol/L, when the quality of resin and yellow rice wine is 1:24, EC removal rate is that 54.77%, Urea removal rate is 58.78%；When
When the concentration for adding Urea in yellow rice wine is 500 μm of ol/L, when the quality of resin and yellow rice wine is 1:24, EC removal rate is 53.96%,
Urea removal rate is 45.2%.
Removal rate of 3 Xanthydrol-4-O-P of table to the true yellow rice wine sample of addition Urea
Note: a): the concentration containing EC itself is 3.43 μm of ol/L in this yellow rice wine, the concentration containing Urea itself is 86.70 μ
mol/L；The Adsorption time is 12h；The removal rate (%) of A:EC；The removal rate (%) of B:Urea
Embodiment 13
To the influence of the physical and chemical index and flavor of yellow rice wine after the processing of xanthenes alcohol modified resin
Xanthenes alcohol modified resin and yellow rice wine (being 86.70 μm of ol/L containing Urea containing 3.43 μm of ol/L of EC) are pressed into quality
Than being mixed for 1:48, after handling 12h, related assays are carried out, specific assay method is as follows:
The measurement of alcoholic strength, total acid, total reducing sugar, amino-acid nitrogen is referring to GB/T 13662-2008 yellow rice wine (GB 2008).
The flavor substance assay of yellow rice wine: it draws wine sample 8mL and is placed in the ml headspace bottle of 20mL, 3g sodium chloride is added, insert
Enter solid phase micro-extracting head (DVB/CAR/PDMS, 50/30 μm), 50 DEG C of preheating 5min, extraction absorption 45min, GC desorb 5min.GC
Condition are as follows: chromatographic column is TG-SQC capillary column (column length 15m, internal diameter 0.32mm, 0.25 μm of film thickness)；250 DEG C of injector temperature；
Temperature program is to be warming up to 80 DEG C in 35 DEG C of holding 5min with 2 DEG C/min, keeps 1min, then rise to 230 DEG C with 4 DEG C/min, protects
Hold 5min；Carrier gas is helium, flow velocity 1mL/min；Splitless injecting samples, the fractionation time is not 10min.MS condition are as follows: ion source
For electron bombardment ionization source (EI), 230 DEG C of ion source temperature, ionizing energy 70eV, scanning range 45.00~500.00.
Gained specific experiment the results are shown in Table 4.As can be seen from the table, flavor substance overall loss is smaller before and after the processing, main
The physical and chemical index wanted is also close with former wine sample.Illustrate to handle yellow rice wine using the resin, to the main physical and chemical index of wine body
It is little with the influence of flavor substance content.
Influence of 4 modified resin of the table processing to yellow rice wine main physical and chemical index and flavor substance
Other unspecified parts are the prior art.Although above-described embodiment is made that the present invention and retouches in detail
State, but it is only a part of the embodiment of the present invention, rather than whole embodiments, people can also according to the present embodiment without
Other embodiments are obtained under the premise of creativeness, these embodiments belong to the scope of the present invention.
Claims (7)
1. a kind of xanthenes alcohol modified resin, it is characterised in that: the structural formula of the modified resin are as follows:
Wherein, P is merrifield resin, the structural formula of the merrifield resin are as follows:
And the structural formula of the xanthenes alcohol modified resin are as follows:
2. xanthenes alcohol modified resin according to claim 1, it is characterised in that: under the structural formula of the modified resin is respectively
State any one in structural formula:
3. the method for preparing xanthenes alcohol modified resin described in claim 1, it is characterised in that: the following steps are included:
1) 1 part of hydroxyl Oxoxanthone, 0.5~3 part of Anhydrous potassium carbonate, 0.2~3 part of merrifield tree are weighed by ratio of weight and the number of copies
Rouge, 0.2~1 part of sodium borohydride and 0.2~1 part of anhydrous lithium chloride；
2) hydroxyl Oxoxanthone and Anhydrous potassium carbonate are uniformly mixed first, obtain mixture, mixture is then dissolved in dimethyl
Then under protection of argon gas acetamide is 70~90 DEG C in temperature and is stirred to react 3~5h, merrifield resin is then added
It stirs evenly, the reaction was continued 20~30h is filtered after being cooled to room temperature, washed, is dried in vacuo, obtain solid matter；
3) solid matter, sodium borohydride, anhydrous lithium chloride are dissolved in tetrahydrofuran and are uniformly mixed, reacted at room temperature
10~16h then heats to 35~45 DEG C of 20~48h of reaction, filters after being cooled to room temperature, and washing is to get modified to xanthenes alcohol
Resin.
4. according to the method described in claim 3, it is characterized by: the hydroxyl Oxoxanthone is 1- hydroxyl Oxoxanthone, 2- hydroxyl
Any one in Oxoxanthone, 3- hydroxyl Oxoxanthone and 4- hydroxyl Oxoxanthone.
5. a kind of application of the xanthenes alcohol modified resin described in claim 1 in absorption urethanes and urea.
6. application according to claim 5, it is characterised in that: the application method: the modified tree of xanthenes alcohol being added into wine
Rouge is stirred to react under room temperature, and centrifugation obtains supernatant；
Wherein, wine and xanthenes alcohol modified resin mass ratio are 24~96:1.
7. application according to claim 6, it is characterised in that: the wine is yellow rice wine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810475169.0A CN108440689B (en) | 2018-05-17 | 2018-05-17 | Xanthenes alcohol modified resin and its preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810475169.0A CN108440689B (en) | 2018-05-17 | 2018-05-17 | Xanthenes alcohol modified resin and its preparation method and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108440689A CN108440689A (en) | 2018-08-24 |
| CN108440689B true CN108440689B (en) | 2019-08-20 |
Family
ID=63203919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810475169.0A Expired - Fee Related CN108440689B (en) | 2018-05-17 | 2018-05-17 | Xanthenes alcohol modified resin and its preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108440689B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101328164A (en) * | 2007-06-22 | 2008-12-24 | 上海五洲药厂二分厂 | Method for preparing xanthydrol from xanthones as raw material |
| CN102353728A (en) * | 2011-06-29 | 2012-02-15 | 中国食品发酵工业研究院 | Rapid detection method for production process quality control of yellow wine |
| CN103760266A (en) * | 2014-01-16 | 2014-04-30 | 深圳市华测检测技术股份有限公司 | Method for detecting content of urea in brewed wine by using high performance liquid chromatography |
| CN107698551A (en) * | 2017-11-28 | 2018-02-16 | 陕西启源科技发展有限责任公司 | The preparation method of xanthene alcohol |
-
2018
- 2018-05-17 CN CN201810475169.0A patent/CN108440689B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101328164A (en) * | 2007-06-22 | 2008-12-24 | 上海五洲药厂二分厂 | Method for preparing xanthydrol from xanthones as raw material |
| CN102353728A (en) * | 2011-06-29 | 2012-02-15 | 中国食品发酵工业研究院 | Rapid detection method for production process quality control of yellow wine |
| CN103760266A (en) * | 2014-01-16 | 2014-04-30 | 深圳市华测检测技术股份有限公司 | Method for detecting content of urea in brewed wine by using high performance liquid chromatography |
| CN107698551A (en) * | 2017-11-28 | 2018-02-16 | 陕西启源科技发展有限责任公司 | The preparation method of xanthene alcohol |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108440689A (en) | 2018-08-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102898566B (en) | Preparation method of metal organic framework molecularly imprinted polymer used for enriching trace amounts of Metolcarb | |
| CN105837643B (en) | A kind of method that D-Glucose isomerization prepares D-Fructose | |
| CN105861235A (en) | Method for reducing urea in fermented grains of Luzhou-flavor liquor | |
| CN106497996A (en) | The enzyme catalysiss preparation method of chiral alcohol | |
| JP2021519106A (en) | How to extract citrulline from watermelon | |
| CN108440689B (en) | Xanthenes alcohol modified resin and its preparation method and application | |
| CN101831475A (en) | Method for producing high-purity oligomate | |
| CN105754983A (en) | Immobilized enzyme for preparing Ezetimibe midbody and preparation method of immobilized enzyme | |
| US20200299140A1 (en) | Method for preparing nitrogen-containing activated carbon through ammonia activation | |
| KR102407724B1 (en) | An Enzyme for ginsenoside bioconversion | |
| Ji et al. | Co-immobilised 7α-and 7β-HSDH as recyclable biocatalyst: High-performance production of TUDCA from waste chicken bile | |
| CN105968042A (en) | Preparation method of migltol | |
| KR101477693B1 (en) | A preparation method of galactooligosaccharides with enhanced galactosyllactose which is a ingredient of mother's milk | |
| CN109254104A (en) | The detection method of residues of organophosphate pesticides in a kind of grape wine | |
| CN112493484B (en) | Preparation method of mume fructus essence rich in mume fructus extract and high-purity mume fructus extract | |
| CN115353982A (en) | High-yield phenolic acid-yield aureobasidium ramosum and application thereof in fen-flavor Xiaoqu liquor | |
| CN105733909B (en) | A kind of method of urea in reduction yellow rice wine | |
| Kopečný et al. | The effect of yellow affinity substance on cellulases of Ruminococcus flavefaciens | |
| CN101270351B (en) | Method for purifying velardon by using metallic affinity membrane | |
| CN102816054A (en) | Environment-friendly method for preparing adipic acid by catalytic oxidation | |
| CN113754526A (en) | High-purity coenzyme Q10 purification process | |
| CN101342483B (en) | Synthesis of selective separation functional material for dichlorvos | |
| CN102516340A (en) | Method for separating and purifying hydroxycobalamin by using D150 macroporous resin | |
| CN101545002A (en) | Method for improving the concentration of substrate in biological resolution L-menthol reaction | |
| CN105669612B (en) | A kind of methyl 2 of 3 hydroxyl 4（5 hydrogen）The preparation method of furanone |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20190820 |