CN106946901A - A kind of plain precursor of rosin and its synthetic method - Google Patents
A kind of plain precursor of rosin and its synthetic method Download PDFInfo
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- CN106946901A CN106946901A CN201710216739.XA CN201710216739A CN106946901A CN 106946901 A CN106946901 A CN 106946901A CN 201710216739 A CN201710216739 A CN 201710216739A CN 106946901 A CN106946901 A CN 106946901A
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- reaction
- rosin
- consumption
- vanillic aldehyde
- maleate
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- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims abstract description 29
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 title claims abstract description 29
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 239000002243 precursor Substances 0.000 title claims abstract description 24
- 238000010189 synthetic method Methods 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims abstract description 20
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000002808 molecular sieve Substances 0.000 claims abstract description 17
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052772 Samarium Inorganic materials 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052751 metal Inorganic materials 0.000 claims abstract description 11
- 239000002184 metal Substances 0.000 claims abstract description 11
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims abstract description 9
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims abstract description 9
- 239000000843 powder Substances 0.000 claims abstract description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims abstract description 4
- 238000011084 recovery Methods 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000004090 dissolution Methods 0.000 claims abstract description 3
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 claims description 2
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 5
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 description 6
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229930014626 natural product Natural products 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000576429 Forsythia suspensa Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 244000167222 Acanthopanax sessiliflorus Species 0.000 description 1
- 235000017615 Acanthopanax sessiliflorus Nutrition 0.000 description 1
- 244000296912 Ageratum conyzoides Species 0.000 description 1
- 235000004405 Ageratum conyzoides Nutrition 0.000 description 1
- 241001093951 Ailanthus altissima Species 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- HGXBRUKMWQGOIE-UHFFFAOYSA-N COc1cc(C2OCC3C(c(cc4OC)ccc4O)OCC23)ccc1O Chemical compound COc1cc(C2OCC3C(c(cc4OC)ccc4O)OCC23)ccc1O HGXBRUKMWQGOIE-UHFFFAOYSA-N 0.000 description 1
- 235000016535 Capraria biflora Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000197960 Galium verum Species 0.000 description 1
- 235000000911 Galium verum Nutrition 0.000 description 1
- 235000017309 Hypericum perforatum Nutrition 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- 241000207960 Pedaliaceae Species 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000010523 cascade reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 235000021018 plums Nutrition 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006578 reductive coupling reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Developing Agents For Electrophotography (AREA)
Abstract
Directly promote the method that vanillic aldehyde and maleate single step reaction prepare the plain precursor of dilactone type rosin using samarium metal in the presence of cuprous iodide and molecular sieve the invention discloses a kind of.Under stirring by vanillic aldehyde and maleate in the dry tetrahydrofuran of prior water removal mixed dissolution, then sequentially add samarium metal powder, cuprous iodide powder, molecular sieve.Reaction system is carried out under conditions of absolute.It is stirred at room temperature down until reaction is complete.Resulting reaction mixture carries out solvent recovery, after residue is post-treated, the plain precursor sterling of the isolated dilactone type rosin of chromatographic column.
Description
Technical field
The invention belongs to organic chemical synthesis field, and in particular to one kind is prepared double using vanillic aldehyde and maleate simplicity
The method of lactone type rosin element precursor.
Background technology
Rosin element, natural products is widely present in the root of Araliaceae Panax sessiliflorus, Pedaliaceae plant sesame seed or
In seed oil, the various plants such as goatweed royal paulownia woody part, be the capsule of weeping forsythia, it is blue or green stick up, one of the active ingredient of a variety of medicinal materials [text
Offer 1:Liu Donglei, Xu Suixu, Wang Wei virtue .Journal of Chinese Pharmaceutical Sciences 1998,7,
49-51；Document 2:Cold light, Wang Haiou, Ming Dongsheng Mountain Western Medicine S University journal, 2003,3,227-228；Document 3:Wang Jin plums
He'nan University, Master's thesis in 2008].Rosin element has stronger antioxidation activity, in vivo with reduction serum courage
A variety of physiologically actives [document 4 such as sterol, regulating lipid metabolism, stabilizing blood pressure and anticancer:Hair prestige capsules of weeping forsythia chemical composition and its
The research of antitumor activity, Hubei College Of Traditional Chinese Medicine, Master's thesis in 2009；Document 5:The super fruits of Ailanthus altissima of Zhao Chun and Galium verum chemistry
Composition and bioactivity research, Shenyang Pharmaceutical University, thesis for the doctorate in 2007].Generally to be extracted as rosin from natural products
Plain main source [document 6:Zhang Xianzhong, Huanghai Sea intelligence, Zhong Liezhou, Sun Yujing, the Chinese grain and oil journals of the emerging universe of leaf, 2012,27,122-
128], price is costly.Dilactone type structural framework is often the important feature unit of Lignanoids compounds.According to document
Report [document 3.K.K.Rana, C.Guin and S.C.Roy, Tetrahedron Letters, 2000,41,9337-
9338], rosin element can be prepared by reducing the plain dilactone type precursor of rosin.Therefore, it is possible to cost-effectively prepare in double
Ester type rosin element precursor, is to synthesize one of critical path of rosin element.But, the plain existing synthesis side of precursor of dilactone type rosin
Often there is many limitations in method, such as operation is complicated, yield is relatively low, reagent cost is high, substrate be less susceptible to or route it is superfluous
It is long etc..
Samarium is one kind of rare earth element.Samarium diodide was introduced organic first by french chemist Kagan since 1980
Since in synthesis, samarium reagents have obtained application widely in organic synthesis, and it can promote polytype chemical reaction
With the conversion of functional group, and have been successfully applied for a variety of natural products synthesis [M.Szostak,
N.J.Fazakerley,D.Parmar,D.J.Procter,Chemical Reviews,2014,114,5959-6039].No
Cross, samarium diodide is existed in place of some shortcomings in use, such as very sensitive to air, thus preserves relatively difficult for a long time,
It is usually existing to be made with existing.On the other hand, samarium diodide only make use of an electricity in use as single electron transfer reagent
Son.These all limit its application on extensive prepare.Comparatively speaking, samarium metal is relatively stablized in atmosphere, it is easy to operate,
Price is also relatively cheap, and has more electronics to be effectively utilized.Therefore, samarium metal is directly used for organic conjunction
Into with more preferable prospect.There are abundant rare earth resources in China, accounts for more than the 90% of world saving, develops rare earth resources tool
It is of great importance.
Directly promote vanillic aldehyde and horse using samarium metal in the presence of cuprous iodide and molecular sieve the invention discloses one kind
Carry out the method that acid esters single step reaction prepares the plain precursor of dilactone type rosin, this method is there is not yet domestic and foreign literature is reported.
The content of the invention
The plain precursor of dilactone type rosin is prepared it is an object of the invention to provide a kind of use vanillic aldehyde and maleate
Short-cut method.
Technical scheme is as follows：
In the presence of cuprous iodide and molecular sieve, using samarium metal, by vanillic aldehyde and maleate, reductive coupling is simultaneously at room temperature
Original flavor condensation is the plain precursor of dilactone type rosin, and its reaction expression is shown below：
In formula, the preferred CH of R3, C2H5；The preferred 3A molecular sieves of molecular sieve, 4A molecular sieves.
Technical scheme is as follows：By vanillic aldehyde and maleate in the dry tetrahydrofuran of prior water removal under stirring
Middle mixed dissolution, then sequentially adds samarium metal powder, cuprous iodide powder, molecular sieve.Wherein, maleate consumption is vanillic aldehyde
0.5-5 times of the mol ratio of consumption；Samarium powder consumption is 0.5-5 times of the mol ratio of vanillic aldehyde consumption；Cuprous iodide consumption is used for samarium powder
0.5-5 times of the mol ratio of amount；Molecular sieve consumption is 2-20 times of vanillic aldehyde quality；Tetrahydrofuran consumption is vanillic aldehyde quality
10-100 times；Reaction system is carried out under conditions of absolute.
It is stirred at room temperature down until reaction is complete.Resulting reaction mixture carries out solvent recovery, and residue is post-treated
Afterwards, the plain precursor sterling of the isolated dilactone type rosin of chromatographic column, yield 60-90%.
Advantages and positive effects of the present invention：Synthetic route of the present invention is simply efficient, only need to pass through cascade reaction one-step method
The plain precursor of dilactone type rosin is can obtain, operating procedure is few, without separation of intermediates, greatly simplifies operation and requires；This
Invention reaction condition is easily achieved, and can directly operate in atmosphere, it is to avoid anaerobic, low temperature, high temperature, illumination, biology
The particular/special requirements such as catalysis；The raw material of the present invention is simple and easy to get, and vanillic aldehyde, maleate are basic chemical industry product, it is easy to obtain；
Samarium metal used of the invention is rare earth metal, and the rare earth resources of China account for more than the 90% of the world, therefore effective exploitation utilizes dilute
Earth metal is significant to China；The plain precursor yield of rosin that the present invention is synthesized is high, and last handling process is simple, locates after product
It is easily isolated during reason；Solvents tetrahydrofurane used can fully recovery, and thus make reaction cost enter one in the present invention
Step declines.
Embodiment
Following synthesis example is used for further illustrating the present invention, but is not intended to limit the present invention.
Example 1
The samarium metal powder of 3g brand-news is sequentially added into reaction vessel, then cuprous iodide 3.9g, KI 6.8g add
100mL removes water dry tetrahydrofuran, magnetic agitation in advance.Add vanillic aldehyde 3g, dimethyl maleate 5mL, 4A molecular sieve 5g.
Reaction solution darkens in 2h, continues to react 8h.Add 50mL watery hydrochloric acid (2molL-1) terminating reaction, reaction mixture warp
Post processing obtains crude product, then further by chromatography, obtains the plain precursor of dilactone type rosin, yield 80%.
White solid, fusing point>250℃.1HNMR(500MHz,CDCl3)δppm 9.85(s,2H),7.09-6.94(m,
2H),6.87-6.75(m,4H),6.03-6.02(m,1H),5.97(m,1H),3.96-3.93(m,6H),3.77-3.74(m,
2H)；13C NMR(125MHz,CDCl3)δppm 177.6,173.2,139.4,137.6,137.1,136.5,133.1,132.2,
130.0,126.8,125.9,124.0,123.3,102.2,81.8,80.8,51.9,46.6；IR(KBr/cm-1)ν3298,
3037,2945,1772,1763,1509,1460.
Example 2
By the method for example 1,4A molecular sieves are replaced using 3A molecular sieves, the plain precursor of dilactone type rosin, yield 73% is obtained.
Example 3
By the method for example 1, dimethyl maleate is replaced using diethyl maleate, the plain precursor of dilactone type rosin is obtained,
Yield 61%.
Claims (5)
1. a kind of simple and easy method for synthesizing the plain precursor of rosin, it is characterised in that in the presence of cuprous iodide and molecular sieve, use gold
Category samarium promotes vanillic aldehyde and maleate single step reaction to prepare the plain precursor of dilactone type rosin, and its preparation process includes following step
Suddenly：
Be stirred at room temperature it is lower by vanillic aldehyde and maleate in the dry tetrahydrofuran of prior water removal mixed dissolution, then successively plus
Enter samarium metal powder, cuprous iodide powder, molecular sieve, be stirred at room temperature down until reaction is complete, resulting reaction mixture is carried out
Solvent recovery, after residue is post-treated, the plain precursor sterling of the isolated dilactone type rosin of chromatographic column.
2. a kind of simple and easy method for synthesizing the plain precursor of rosin according to claim 1, it is characterised in that the Malaysia used
Acid esters consumption is 0.5-5 times of the mol ratio of vanillic aldehyde consumption；Samarium powder consumption is 0.5-5 times of the mol ratio of vanillic aldehyde consumption；Iodate
Cuprous consumption is 0.5-5 times of the mol ratio of samarium powder consumption；Molecular sieve consumption is 2-20 times of vanillic aldehyde quality；Tetrahydrofuran consumption
For 10-100 times of vanillic aldehyde quality.
3. a kind of simple and easy method for synthesizing the plain precursor of rosin according to claim 1, it is characterised in that used Malaysia
Acid esters is methyl maleate, the one or more of ethyl maleate.
4. a kind of simple and easy method for synthesizing the plain precursor of rosin according to claim 1, it is characterised in that used molecule
Sieve preferred 3A molecular sieves, the one or more of 4A molecular sieves.
5. a kind of simple and easy method for synthesizing the plain precursor of rosin according to claim 1, it is characterised in that course of reaction is one
Pot method single step reaction, reaction temperature is room temperature, and reaction dissolvent can be reclaimed, reaction yield 60-90%.
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| CN201710216739.XA CN106946901A (en) | 2017-04-06 | 2017-04-06 | A kind of plain precursor of rosin and its synthetic method |
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| CN201710216739.XA CN106946901A (en) | 2017-04-06 | 2017-04-06 | A kind of plain precursor of rosin and its synthetic method |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108689880A (en) * | 2018-07-16 | 2018-10-23 | 青岛科技大学 | Solventless method prepares diphenyl hydroxypropionitrile |
| CN114573790A (en) * | 2022-03-17 | 2022-06-03 | 宁波锋成先进能源材料研究院有限公司 | Bio-based degradable epoxy resin, preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105663110A (en) * | 2014-11-18 | 2016-06-15 | 复旦大学 | Application of lignan compound 4-keto pinoresinol in preparing anti-hepatitis B virus medicine |
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2017
- 2017-04-06 CN CN201710216739.XA patent/CN106946901A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105663110A (en) * | 2014-11-18 | 2016-06-15 | 复旦大学 | Application of lignan compound 4-keto pinoresinol in preparing anti-hepatitis B virus medicine |
Non-Patent Citations (3)
| Title |
|---|
| MICHAEL ANTOLOVICH等: "LC-MS Investigation of Oxidation Products of Phenolic Antioxidants", 《J. AGRIC. FOOD CHEM.》 * |
| U. KRINGS,等: "Phenyl propenoic side chain degradation of ferulic acid by Pycnoporus cinnabarinus — elucidation of metabolic pathways using [5-2H]-ferulic acid", 《JOURNAL OF BIOTECHNOLOGY》 * |
| 田广: "Sm/CuI/KI催化a-β-不饱和化合物双加成反应的研究", 《青岛科技大学硕士学位论文》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108689880A (en) * | 2018-07-16 | 2018-10-23 | 青岛科技大学 | Solventless method prepares diphenyl hydroxypropionitrile |
| CN108689880B (en) * | 2018-07-16 | 2020-12-22 | 青岛科技大学 | Solvent-free method for preparing diphenyl hydroxyl propionitrile |
| CN114573790A (en) * | 2022-03-17 | 2022-06-03 | 宁波锋成先进能源材料研究院有限公司 | Bio-based degradable epoxy resin, preparation method and application thereof |
| CN114573790B (en) * | 2022-03-17 | 2023-11-17 | 宁波锋成绿能环保科技有限公司 | Bio-based degradable epoxy resin, preparation method and application thereof |
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