CN113831222A - Production method of binaphthol - Google Patents
Production method of binaphthol Download PDFInfo
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- CN113831222A CN113831222A CN202111206751.5A CN202111206751A CN113831222A CN 113831222 A CN113831222 A CN 113831222A CN 202111206751 A CN202111206751 A CN 202111206751A CN 113831222 A CN113831222 A CN 113831222A
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- China
- Prior art keywords
- binaphthol
- mixture
- producing
- test tube
- naphthol
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- DVWQNBIUTWDZMW-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalen-2-ol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=CC=CC2=C1 DVWQNBIUTWDZMW-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 45
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229950011260 betanaphthol Drugs 0.000 claims abstract description 16
- 238000005303 weighing Methods 0.000 claims abstract description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 10
- 238000001291 vacuum drying Methods 0.000 claims abstract description 10
- 239000013078 crystal Substances 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 238000000227 grinding Methods 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 6
- 239000004570 mortar (masonry) Substances 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 23
- 230000009286 beneficial effect Effects 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 4
- 239000010865 sewage Substances 0.000 abstract description 4
- 239000002910 solid waste Substances 0.000 abstract description 4
- 230000035484 reaction time Effects 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 9
- 230000007547 defect Effects 0.000 description 5
- 238000005265 energy consumption Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000009471 action Effects 0.000 description 3
- 238000007873 sieving Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000004075 alteration Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
Abstract
The invention relates to the technical field of binaphthol, and discloses a method for producing binaphthol, which comprises the following steps: weighing appropriate amount of beta-naphthol and FeCl according to proportion3·6H2O in a mortar; beta-naphthol and FeCl were mixed with pestle at room temperature3·6H2Finely grinding the mixture of O; transferring the ground mixture into a test tube, transferring the test tube into an oven and placing the test tube; cooling the mixture to room temperature, decomposing the mixture with dilute hydrochloric acid, filtering, washing and vacuum drying; recrystallizing the mixture by using aromatic hydrocarbon, and drying for a period of time in vacuum to obtain yellow binaphthol crystals. The method for producing binaphthol can simply and efficiently obtain high-quality binaphthol with the purity of more than 99 percent, greatly reduces byproducts, sewage and solid waste after the reaction is finished, has great progress, and also reduces the using amount of aromatic hydrocarbon; also, the reaction time is short, which is beneficial to increase of purity and increase of efficiency.
Description
Technical Field
The invention relates to the technical field of binaphthol, in particular to a method for producing binaphthol.
Background
The existing method for preparing binaphthol is generally an oxidation coupling method of 2-naphthol, the oxidant adopts metal salt, metal oxide or complex with high valence, the using amount is more than 1 equivalent relative to 2-naphthol, and because the oxidant with more than 1 equivalent is used, a large amount of metal salt and metal hydroxide can be produced as byproducts in the post-treatment process after the reaction is finished, a large amount of sewage and solid waste are produced, and the method has great defects.
The prior art has the following defects and shortcomings:
the method for preparing binaphthol in the prior art has the defects of poor reaction selectivity, low conversion rate, slow reaction rate, high pollution, high energy consumption, complex operation and the like.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a method for producing binaphthol, which can solve the problems of poor reaction selectivity, low conversion rate, slow reaction rate, large pollution, high energy consumption, complex operation and the like in the existing method for producing binaphthol; the invention adopts the solvent-free organic synthesis by arranging the production method of the binaphthol, and compared with the traditional reaction, the solvent-free organic reaction has the advantages of good reaction selectivity, high conversion rate, high reaction rate, small pollution, low energy consumption, simple operation and the like. The mechanism of the solventless reaction is the same as that of the reaction in solution, where the reaction occurs by diffusion contact of two reactant molecules to produce product molecules. At the moment, the generated product molecules are dispersed in a parent reactant as impurities and defects, when the product molecules are aggregated to a certain degree, crystal nuclei of the product appear, so that the nucleation process is completed, and then an independent crystal phase of the product appears along with the growth of the crystal nuclei.
In order to realize the purpose of the production method of the binaphthol, the invention provides the following technical scheme: a method for producing binaphthol comprises the following steps:
the method comprises the following steps: weighing appropriate amount of beta-naphthol and FeCl according to proportion3·6H2O in a mortar;
step two: beta-naphthol and FeCl were mixed with pestle at room temperature3·6H2Finely grinding the mixture of O;
step three: transferring the ground mixture into a test tube, transferring the test tube into an oven and placing the test tube;
step four: cooling the mixture to room temperature, decomposing the mixture with dilute hydrochloric acid, filtering, washing and vacuum drying;
step five: recrystallizing the mixture by using aromatic hydrocarbon, drying the mixture in vacuum for a period of time to obtain yellow binaphthol crystals, weighing the product, measuring the melting point, and calculating the yield.
Preferably, the beta-naphthol and FeCl weighed in the step one3·6H2The mass ratio of O is 1: 2.
Preferably, the mixture in step two is finely ground and then filtered using a fine filter sieve.
Preferably, the mixture is transferred into an oven and placed in the third step, the temperature of the oven is set to be 50 ℃, and the time for placing the mixture is 1.5 to 2 hours.
Preferably, the vacuum drying time in the fourth step is 1.5-2 h.
Preferably, in the step five, in the process of recrystallizing the mixture by using toluene, activated carbon is combined for treatment, so as to obtain the binaphthol.
Preferably, in the fifth step, the mixture is recrystallized by using aromatic hydrocarbon, and the aromatic hydrocarbon is one of toluene and xylene.
Preferably, the vacuum drying time in the fifth step is 16-20 h.
Compared with the prior art, the invention provides a production method of binaphthol, which has the following beneficial effects:
the production method of the binaphthol has the advantages that the high-quality binaphthol with the purity of more than 99 percent is simply and efficiently obtained, the byproducts, the sewage and the solid waste are greatly reduced after the reaction is finished, great progress is realized, and the using amount of aromatic hydrocarbon is also reduced; also, the reaction time is short, which is beneficial to increase of purity and increase of efficiency.
Drawings
FIG. 1 is a schematic diagram of a reaction formula for binaphthol synthesis according to the present invention;
FIG. 2 is a schematic diagram of the reaction formula of binaphthol synthesis of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Referring to fig. 1-2, the following embodiment is given:
a method for producing binaphthol comprises the following steps:
s1: weighing beta-naphthol 1g and FeCl3·6H2O3.8 g in a mortar;
s2: beta-naphthol and FeCl were mixed with pestle at room temperature3·6H2Finely grinding the mixture of O, and sieving the ground mixture;
s3: transferring the ground mixture into a test tube, transferring the test tube into a 50 ℃ oven, and standing for 1.5 h;
s4: cooling the mixture to room temperature, decomposing the mixture with dilute hydrochloric acid, filtering, washing, and vacuum drying for 1.5 h;
s5: and recrystallizing the mixture by using toluene, drying for 16h in vacuum to obtain yellow binaphthol crystals, weighing the product, measuring the melting point, and calculating the yield.
The following example II is given:
a method for producing binaphthol comprises the following steps:
s1: weighing beta-naphthol 1g and FeCl3·6H2O3.8 g in a mortar;
s2: beta-naphthol and FeCl were mixed with pestle at room temperature3·6H2Finely grinding the mixture of O, and sieving the ground mixture;
s3: transferring the ground mixture into a test tube, transferring the test tube into an oven at 50 ℃, and standing for 1.7 h;
s4: cooling the mixture to room temperature, decomposing the mixture with dilute hydrochloric acid, filtering, washing, and vacuum drying for 1.7 h;
s5: and recrystallizing the mixture by using toluene, drying for 18h in vacuum to obtain yellow binaphthol crystals, weighing the product, measuring the melting point, and calculating the yield.
The following gives a third embodiment:
a method for producing binaphthol comprises the following steps:
s1: weighing beta-naphthol 1g and FeCl3·6H2O3.8 g in a mortar;
s2: beta-naphthol and FeCl were mixed with pestle at room temperature3·6H2Finely grinding the mixture of O, and sieving the ground mixture;
s3: transferring the ground mixture into a test tube, transferring the test tube into a 50 ℃ oven, and standing for 2 hours;
s4: cooling the mixture to room temperature, decomposing the mixture with dilute hydrochloric acid, filtering, washing, and vacuum drying for 2 h;
s5: and recrystallizing the mixture by using toluene, drying for 20 hours in vacuum to obtain yellow binaphthol crystals, weighing the product, measuring the melting point, and calculating the yield.
The working use flow and the installation method of the invention are that when the method for producing the binaphthol is used, the solvent-free organic synthesis is adopted, and compared with the traditional reaction, the solvent-free organic reaction has the advantages of good reaction selectivity, high conversion rate, high reaction rate, small pollution, low energy consumption, simple operation and the like, the method for producing the binaphthol simply and efficiently obtains the high-quality binaphthol with the purity of more than 99 percent, and the by-product, the sewage and the solid waste are greatly reduced after the reaction is finished, so that the method has great progress and reduces the use amount of aromatic hydrocarbon; also, the reaction time is short, which is beneficial to increase of purity and increase of efficiency.
It is noted that, herein, relational terms such as first and second, and the like may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Also, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (8)
1. The production method of the binaphthol is characterized by comprising the following steps:
the method comprises the following steps: weighing appropriate amount of beta-naphthol and FeCl according to proportion3·6H2O in a mortar;
step two: beta-naphthol and FeCl were mixed with pestle at room temperature3·6H2Finely grinding the mixture of O;
step three: transferring the ground mixture into a test tube, transferring the test tube into an oven and placing the test tube;
step four: cooling the mixture to room temperature, decomposing the mixture with dilute hydrochloric acid, filtering, washing and vacuum drying;
step five: recrystallizing the mixture by using aromatic hydrocarbon, drying the mixture in vacuum for a period of time to obtain yellow binaphthol crystals, weighing the product, measuring the melting point, and calculating the yield.
2. The method for producing binaphthol according to step one of claim 1, wherein: the weighed beta-naphthol and FeCl3·6H2The mass ratio of O is 1: 2.
3. The method for producing binaphthol according to step two of claim 1, wherein: and finely grinding the mixture and then filtering by adopting a fine filter screen.
4. The method for producing binaphthol according to the third step of claim 1, wherein: and transferring the mixture into an oven for placing, wherein the temperature of the oven is set to be 50 ℃, and the placing time is 1.5-2 h.
5. The method for producing binaphthol according to the fourth step of claim 1, wherein: the vacuum drying time is 1.5-2 h.
6. The method for producing binaphthol according to step five of claim 1, wherein: and in the process of recrystallizing the mixture by using toluene, treating the mixture by combining activated carbon to obtain the binaphthol.
7. The method for producing binaphthol according to step five of claim 1, wherein: and recrystallizing the mixture by using aromatic hydrocarbon, wherein the aromatic hydrocarbon is one of toluene and xylene.
8. The method for producing binaphthol according to step five of claim 1, wherein: the vacuum drying time is 16-20 h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111206751.5A CN113831222A (en) | 2021-10-15 | 2021-10-15 | Production method of binaphthol |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111206751.5A CN113831222A (en) | 2021-10-15 | 2021-10-15 | Production method of binaphthol |
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| Publication Number | Publication Date |
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| CN113831222A true CN113831222A (en) | 2021-12-24 |
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| CN202111206751.5A Pending CN113831222A (en) | 2021-10-15 | 2021-10-15 | Production method of binaphthol |
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| Country | Link |
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| CN (1) | CN113831222A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115710162A (en) * | 2022-11-17 | 2023-02-24 | 沈阳化工研究院有限公司 | Method for preparing electronic-grade binaphthol by refining at lower temperature |
| CN116037053A (en) * | 2023-04-03 | 2023-05-02 | 江苏鸣翔化工有限公司 | High-efficiency binaphthol integrated production equipment and production method |
-
2021
- 2021-10-15 CN CN202111206751.5A patent/CN113831222A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| 杨思军等: "固相法合成1, 1′-联-2-萘酚", 中国医药工业杂志, vol. 29, no. 8, pages 376 - 377 * |
| 翁文等: "固相合成联萘酚中的双金属盐协同效应", 应用化工, vol. 31, no. 3, pages 20 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115710162A (en) * | 2022-11-17 | 2023-02-24 | 沈阳化工研究院有限公司 | Method for preparing electronic-grade binaphthol by refining at lower temperature |
| CN115710162B (en) * | 2022-11-17 | 2024-03-26 | 沈阳化工研究院有限公司 | Method for refining and preparing electronic cascade naphthol at lower temperature |
| CN116037053A (en) * | 2023-04-03 | 2023-05-02 | 江苏鸣翔化工有限公司 | High-efficiency binaphthol integrated production equipment and production method |
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