CN107698630A - A kind of preparation method of tribenoside - Google Patents
A kind of preparation method of tribenoside Download PDFInfo
- Publication number
- CN107698630A CN107698630A CN201711220450.1A CN201711220450A CN107698630A CN 107698630 A CN107698630 A CN 107698630A CN 201711220450 A CN201711220450 A CN 201711220450A CN 107698630 A CN107698630 A CN 107698630A
- Authority
- CN
- China
- Prior art keywords
- tribenoside
- preparation
- added
- phase
- glucose
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention discloses a kind of preparation method of tribenoside, comprise the following steps：Single acetone glucose and phase transfer catalyst are added in benzyl chloride, inorganic alkali solution is added dropwise in control system reaction temperature, obtain tribenzyl list acetone glucose crude product, purified again by three-level molecular distillation, obtain high-purity tribenzyl list acetone glucose, this is added in acidic alcohol again, tribenoside is made.The building-up process of the present invention is simply efficient, and operation is easy, and rational technology, impurity is less, easy to operate, and combined coefficient is high, and high income, purity content is higher, can directly reach European Pharmacopoeia standard.
Description
Technical field
The invention belongs to chemical synthesis and pharmaceutical technology field, more particularly to it is a kind of preparation method of tribenoside.
Background technology
Tribenoside is the hemorrhoid of Ciba companies initiative, and technological development is introduced by military field drug company in Japan, main
Do anti-inflammatory agent, it may also be used for the raw material of a variety of anti-inflammatory drugs, suitable for the bleeding and swelling of internal piles.
In existing technology, single acetone glucose is added in benzyl chloride, oil bath pan heating, control temperature 85 ~
At 95 DEG C, potassium hydroxide solid is slowly added under stirring, exothermic heat of reaction, controls and adds speed, after the completion of question response, system drop
Temperature, water and organic solvent stratification, organic layer is added dropwise and is washed with water, be evaporated under reduced pressure to without outflow, obtaining intermediate, then by centre
Body is dissolved in ethanol, is passed through hydrogen chloride gas and is reacted to obtain tribenoside.The method reaction temperature is higher, adds potassium hydroxide and puts
Popular drama is strong, and temperature is difficult to control, and easily produces impurity, and a large amount of hydrogen chloride gas are passed through in industrial production and danger be present to people and equipment etc.
Evil, and need to install device for absorbing tail gas additional in addition.
The content of the invention
The purpose of the present invention is to improve the deficiency of existing operation, optimizes the proportioning of raw material, adds phase catalyst simultaneously
Reduce the temperature of reaction so that technique is more reasonable, and the impurity of each step generation is less, purifies, obtains by molecular distillation
Purity be more than 90% tribenzyl list acetone glucose, by subsequently synthesize purification produce content more than 96% tribenoside into
Product.
The present invention to achieve the above object, using following technical scheme：A kind of preparation method of tribenoside of the present invention,
Comprise the following steps：
（1）Single acetone glucose and phase transfer catalyst are added in benzyl chloride, control temperature is added dropwise inorganic at 70 ~ 80 DEG C
Aqueous slkali A, drips off rear stirring reaction 4 ~ 5 hours；
（2）Reaction solution is cooled to 20 DEG C~30 DEG C, organic solvent B extraction is added, takes supernatant liquor, drink washing 2 ~ 4 times, satisfy
Washed 1 ~ 2 time with salt, depressurize and steam organic solvent B；
（3）Above-mentioned material is distilled with three-level Molecular Devices, the three-level Molecular Devices are first order molecular distiller, two level
Molecular still and three-level molecular still, vacuum is 10Pa ~ 100Pa in molecular distillation, the first order molecular distiller, two
The temperature of level molecular still and three-level molecular still is respectively set as 65 DEG C, 125 DEG C and 160 DEG C, and the three-level molecule is set
It is divided into light phase and heavy phase, the mixed liquor of described light phase recovery phenmethylol, methyl phenyl ethers anisole and benzyl chloride after standby distilling material, heavy phase is
Tribenzyl list acetone glucose；
（4）Tribenzyl list acetone glucose is added in 1 ~ 4N hydrochloride ethanol liquids, reacts at room temperature 18h；It is molten to remove ethanol under reduced pressure
Agent, petroleum ether dissolution, sodium bicarbonate solution washing, liquid separation are used at 25 DEG C~35 DEG C；
（5）5 DEG C~10 DEG C are cooled to, releases the grease of precipitation, ensures that grease accounts for the 10 ~ 20% of finished product total amount；
（6）The activated carbon of inventory 1% ~ 5% is added in organic phase, is heated up 25 DEG C~35 DEG C, 0.5h is stirred, filters out activated carbon, is filtered
Liquid is concentrated under reduced pressure dry, and tribenoside finished product is made.
Further, in step（1）In, described phase transfer catalyst is benzyltriethylammoinium chloride, tetrabutyl phosphonium bromide
The combination of one or both of ammonium, tetrabutylammonium chloride, 4-butyl ammonium hydrogen sulfate.
Further, in step（1）In, described single acetone glucose, inorganic alkali solution A, phase transfer catalyst and chlorine
The ratio for changing the amount of the material of benzyl is 1： 3.0~5.0： 0.01~0.05： 3.0~7.0.
Further, in step（1）In, described phase transfer catalyst is tetrabutylammonium chloride or tetrabutyl hydrogen sulfate
The combination of one or both of ammonium.
Further, in step（1）In, described inorganic base A is sodium hydroxide, potassium hydroxide, cesium hydroxide, hydroxide
The combination of one or both of lithium, barium hydroxide.
Further, in step（1）In, described inorganic base A is one or both of sodium hydroxide or potassium hydroxide
Combination.
Further, in step（2）In, described organic solvent B be benzene, chloroform, carbon tetrachloride, n-hexane,
One or more combinations in normal heptane or petroleum ether.
Further, in step（2）In, described organic solvent B be n-hexane, normal heptane or petroleum ether in one kind or
Two kinds of combination.
Further, in step（4）In, the material that feeds intake of described tribenzyl list acetone glucose and hydrochloride ethanol liquid
The ratio of amount is 1：10~15.
Further, in step（5）In, the grease of precipitation, ensure that grease accounts for the 15 ~ 20% of finished product total amount.
Beneficial effect：The building-up process of the present invention is simply efficient, and operation is easy, and rational technology, impurity is less, operation
Convenient, combined coefficient is high, and high income, purity content is higher, can directly reach European Pharmacopoeia standard.
Compared with prior art, the invention has the advantages that：
（1）Phase transfer catalyst, combined coefficient, high income have been used in reaction；Molecular distillation purification mode can remove common high temperature
The inexpungible impurity of institute is evaporated under reduced pressure, while accessory substance can be reclaimed；From charge ratio, reaction temperature, material uses, production
Operation, method of purification are angularly set out.
（2）Reaction condition is gentle, and it is inexpungible miscellaneous that molecular distillation purification mode can remove common high-temperature pressure-reduction distillation institute
Matter, while accessory substance can be reclaimed；Reaction condition is gentle, utilizes impurity caused by the preferable removal of the solubility property of solvent.
Brief description of the drawings
Fig. 1 is the spectrogram of the high performance liquid chromatography of tribenzyl list acetone glucose in case study on implementation 1 of the present invention.
Fig. 2 is the spectrogram of the high performance liquid chromatography of tribenoside in case study on implementation 1 of the present invention.
Embodiment
Following examples only exist in illustrative purpose, without being intended to limit the scope of the present invention.
Embodiment 1
A kind of preparation method of tribenoside of the present invention, comprises the following steps：
（1）Single acetone glucose and phase transfer catalyst are added in benzyl chloride, inorganic base is added dropwise at 70 DEG C in control temperature
Solution A, drips off rear stirring reaction 4 hours；Described phase transfer catalyst is benzyltriethylammoinium chloride.Described inorganic base A
For the combination of two kinds of sodium hydroxide and potassium hydroxide.Described single acetone glucose, inorganic alkali solution A, phase transfer catalyst with
The ratio of the amount of the material of benzyl chloride is 1： 3.0： 0.05：6.0.
（2）Reaction solution is cooled to 30 DEG C, organic solvent B extraction is added, takes supernatant liquor, drinks washing 4 times, saturation food
Salt is washed 1 time, is depressurized and is steamed organic solvent B；Described organic solvent B is benzene.
（3）Above-mentioned material is distilled with three-level Molecular Devices, the three-level Molecular Devices be first order molecular distiller,
Secondary molecules distiller and three-level molecular still, the molecular distillation vacuum of the three-level Molecular Devices are 100Pa, described one
The temperature of level molecular still, secondary molecules distiller and three-level molecular still is respectively set as 65 DEG C, 125 DEG C and 160 DEG C,
It is divided into light phase and heavy phase, described light phase recovery phenmethylol, methyl phenyl ethers anisole and benzyl chloride after the three-level Molecular Devices distilling material
Mixed liquor, heavy phase is tribenzyl list acetone glucose, sampling HPLC detection, as a result as shown in figure 1, purity be 90.75%, contain
Amount 92.11%, yield 83%.
（4）Tribenzyl list acetone glucose is added in 4N hydrochloride ethanol liquids, reacts at room temperature 18h；Remove ethanol under reduced pressure
Solvent, petroleum ether dissolution, sodium bicarbonate solution washing, liquid separation are used at 35 DEG C；Described tribenzyl list acetone glucose and hydrochloric acid
The ratio of the amount of the material that feeds intake of ethanol is 1：10.
（5）5 DEG C are cooled to, the grease of precipitation, ensures that grease accounts for the 20% of finished product total amount.
（6）The activated carbon of inventory 5% is added in organic phase, is heated up 35 DEG C, 0.5h is stirred, filters out activated carbon, filtrate decompression
Concentration is dry, and tribenoside finished product is made, sampling HPLC detections, as a result as shown in Fig. 2 purity is 94.75%, content 97.62%, receives
Rate is 76%.
Fig. 1 is that the spectrogram of the high performance liquid chromatography of tribenzyl list acetone glucose in the embodiment of the present invention 1 is understood, tribenzyl
The purity of single acetone glucose is 90.75%, content 92.11%, yield 83%.Fig. 2 is tribenoside in the embodiment of the present invention 1
The spectrogram of high performance liquid chromatography understand that the purity of tribenoside is 94.75%, content 97.62%, yield 76%.
Embodiment 2
The difference of embodiment 2 and embodiment 1 is：A kind of preparation method of tribenoside of the present invention, comprises the following steps：
（1）Single acetone glucose and phase transfer catalyst are added in benzyl chloride, inorganic base is added dropwise at 75 DEG C in control temperature
Solution A, drips off rear stirring reaction 5 hours；Described phase transfer catalyst is in TBAB and tetrabutylammonium chloride
Two kinds of combination.Described inorganic base A is cesium hydroxide.Described single acetone glucose, inorganic alkali solution A, phase transfer catalysis (PTC)
The ratio of the amount of the material of agent and benzyl chloride is 1：5.0： 0.01： 3.0.
（2）Reaction solution is cooled to 20 DEG C, organic solvent B extraction is added, takes supernatant liquor, drinks washing 2 times, saturation food
Salt is washed 1.5 times, is depressurized and is steamed organic solvent B；Described organic solvent B is in chloroform, carbon tetrachloride and normal heptane
Three kinds of combination.
（3）Above-mentioned material is distilled with three-level Molecular Devices, the three-level Molecular Devices be first order molecular distiller,
Secondary molecules distiller and three-level molecular still, the molecular distillation vacuum of the three-level Molecular Devices is 80Pa, such as Fig. 1 institutes
Show, light phase and heavy phase, described light phase recovery phenmethylol, methyl phenyl ethers anisole and chlorination are divided into after the three-level Molecular Devices distilling material
The mixed liquor of benzyl, heavy phase are tribenzyl list acetone glucose；
（4）Tribenzyl list acetone glucose is added in 3N hydrochloride ethanol liquids, reacts at room temperature 18h；Remove alcohol solvent under reduced pressure,
Petroleum ether dissolution, sodium bicarbonate solution washing, liquid separation are used at 25 DEG C；Described tribenzyl list acetone glucose and hydrochloride ethanol liquid
The material that feeds intake amount ratio be 1： 15.
（5）10 DEG C are cooled to, releases the grease of precipitation, ensures that grease accounts for the 15% of finished product total amount.
（6）The activated carbon of inventory 1% is added in organic phase, is heated up 25 DEG C, 0.5h is stirred, filters out activated carbon, filtrate decompression
Concentration is dry, and tribenoside finished product is made.
Embodiment 3
The difference of embodiment 3 and embodiment 1 is：A kind of preparation method of tribenoside of the present invention, comprises the following steps：
（1）Single acetone glucose and phase transfer catalyst are added in benzyl chloride, inorganic base is added dropwise at 80 DEG C in control temperature
Solution A, drips off rear stirring reaction 4.5 hours；Described phase transfer catalyst is 4-butyl ammonium hydrogen sulfate and TBAB
Combination.Described inorganic base A is the combination of two kinds of lithium hydroxide and barium hydroxide.Described single acetone glucose, inorganic base
The ratio of the amount of the material of solution A, phase transfer catalyst and benzyl chloride is 1： 4.0： 0.03： 7.0.
（2）Reaction solution is cooled to 25 DEG C, organic solvent B extraction is added, takes supernatant liquor, drinks washing 3 times, saturation food
Salt is washed 2 times, is depressurized and is steamed organic solvent B；Described organic solvent B is two kinds of combination in n-hexane and petroleum ether.
（3）Above-mentioned material is distilled with three-level Molecular Devices, the three-level Molecular Devices be first order molecular distiller,
Secondary molecules distiller and three-level molecular still, the molecular distillation vacuum of the three-level Molecular Devices is 10Pa,
（4）Tribenzyl list acetone glucose is added in 1N hydrochloride ethanol liquids, reacts at room temperature 18h；Remove alcohol solvent under reduced pressure,
Petroleum ether dissolution, sodium bicarbonate solution washing, liquid separation are used at 32 DEG C；Described tribenzyl list acetone glucose and hydrochloride ethanol liquid
The material that feeds intake amount ratio be 1：12.
（5）8 DEG C are cooled to, releases the grease of precipitation, ensures that grease accounts for the 10% of finished product total amount.
（6）The activated carbon of inventory 4% is added in organic phase, is heated up 28 DEG C, 0.5h is stirred, filters out activated carbon, filtrate decompression
Concentration is dry, and tribenoside finished product is made.
General principle, principal character and the advantages of the present invention of the present invention has been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the simply explanation described in above-described embodiment and specification is originally
The principle of invention, without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, the present invention
Claimed scope is by appended claims, specification and its equivalent thereof.
Claims (10)
1. a kind of preparation method of tribenoside, it is characterised in that comprise the following steps：
（1）Single acetone glucose and phase transfer catalyst are added in benzyl chloride, control temperature is added dropwise inorganic at 70 ~ 80 DEG C
Aqueous slkali A, drips off rear stirring reaction 4 ~ 5 hours；
（2）Reaction solution is cooled to 20 DEG C~30 DEG C, organic solvent B extraction is added, takes supernatant liquor, drink washing 2 ~ 4 times, satisfy
Washed 1 ~ 2 time with salt, depressurize and steam organic solvent B；
（3）Above-mentioned material is distilled with three-level Molecular Devices, the three-level Molecular Devices are first order molecular distiller, two level
Molecular still and three-level molecular still, vacuum is 10Pa ~ 100Pa in molecular distillation, the first order molecular distiller, two
The temperature of level molecular still and three-level molecular still is respectively set as 65 DEG C, 125 DEG C and 160 DEG C, and the three-level molecule is set
It is divided into light phase and heavy phase, the mixed liquor of described light phase recovery phenmethylol, methyl phenyl ethers anisole and benzyl chloride after standby distilling material, heavy phase is
Tribenzyl list acetone glucose；
（4）Tribenzyl list acetone glucose is added in 1 ~ 4N hydrochloride ethanol liquids, reacts at room temperature 18h；It is molten to remove ethanol under reduced pressure
Agent, petroleum ether dissolution, sodium bicarbonate solution washing, liquid separation are used at 25 DEG C~35 DEG C；
（5）5 DEG C~10 DEG C are cooled to, releases the grease of precipitation, ensures that grease accounts for the 10 ~ 20% of finished product total amount；
（6）The activated carbon of inventory 1% ~ 5% is added in organic phase, is heated up 25 DEG C~35 DEG C, 0.5h is stirred, filters out activated carbon, is filtered
Liquid is concentrated under reduced pressure dry, and tribenoside finished product is made.
2. the preparation method of tribenoside according to claim 1, it is characterised in that：In step（1）In, described phase turns
Shifting catalyst be benzyltriethylammoinium chloride, TBAB, tetrabutylammonium chloride, one kind in 4-butyl ammonium hydrogen sulfate or
Two kinds of combination.
3. the preparation method of tribenoside according to claim 1, it is characterised in that：In step（1）In, described single third
Ketone glucose, inorganic alkali solution A, the weight ratio of phase transfer catalyst and benzyl chloride are 1： 3.0~5.0： 0.01~0.05： 3.0
~7.0。
4. the preparation method of tribenoside according to claim 2, it is characterised in that：In step（1）In, described phase turns
Shifting catalyst is the combination of one or both of tetrabutylammonium chloride or 4-butyl ammonium hydrogen sulfate.
5. the preparation method of tribenoside according to claim 1, it is characterised in that：In step（1）In, described is inorganic
Alkali A is the combination of one or both of sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide, barium hydroxide.
6. the preparation method of tribenoside according to claim 5, it is characterised in that：In step（1）In, described is inorganic
Alkali A is the combination of one or both of sodium hydroxide or potassium hydroxide.
7. the preparation method of tribenoside according to claim 1, it is characterised in that：In step（2）In, described is organic
Solvent B is one or more combinations in benzene, chloroform, carbon tetrachloride, n-hexane, normal heptane or petroleum ether.
8. the preparation method of tribenoside according to claim 7, it is characterised in that：In step（2）In, described is organic
Solvent B is the combination of one or both of n-hexane, normal heptane or petroleum ether.
9. the preparation method of tribenoside according to claim 1, it is characterised in that：In step（4）In, three described benzyls
The weight ratio of the inventory of base list acetone glucose and hydrochloride ethanol liquid is 1：10~15.
10. the preparation method of the tribenoside according to any one of claim 1 to 9, it is characterised in that：In step（5）In,
The grease of precipitation, ensure that grease accounts for the 15 ~ 20% of finished product total amount.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711220450.1A CN107698630A (en) | 2017-11-29 | 2017-11-29 | A kind of preparation method of tribenoside |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711220450.1A CN107698630A (en) | 2017-11-29 | 2017-11-29 | A kind of preparation method of tribenoside |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107698630A true CN107698630A (en) | 2018-02-16 |
Family
ID=61181171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711220450.1A Pending CN107698630A (en) | 2017-11-29 | 2017-11-29 | A kind of preparation method of tribenoside |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107698630A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112028950A (en) * | 2019-06-03 | 2020-12-04 | 鲁南制药集团股份有限公司 | Preparation method of tribenoside |
| CN113200823A (en) * | 2021-04-29 | 2021-08-03 | 南京威尔生物科技有限公司 | Preparation method of benzyl alcohol with low peroxide value |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS276904B6 (en) * | 1988-08-18 | 1992-09-16 | Vyzk Ustav Farm Biochem Sp | Process for preparing crystalline 3,5,6-tri-0-benzyl-alpha-d-glucofuranose |
| CN104478955A (en) * | 2014-12-09 | 2015-04-01 | 济南卡博唐生物科技有限公司 | Preparation method of 3, 5, 6-tri-oxo-benzyl-1, 2-isopropylidene-D-glucose |
| CN106046067A (en) * | 2016-03-15 | 2016-10-26 | 山东康曼生物科技有限公司 | Synthetic method for 1,2-di-O-isopropylidene-3,5,6-tri-O-benzyl-D-glucofuranose |
| CN106589015A (en) * | 2016-10-20 | 2017-04-26 | 利安隆（天津）实业有限公司 | Synthetic method of tribenoside |
| CN107365332A (en) * | 2016-05-11 | 2017-11-21 | 浙江合糖科技有限公司 | The preparation method of-O- benzyl-alpha-D- glucofuranose the glycosides of 1,2- isopropylidenes -3,5,6- three |
-
2017
- 2017-11-29 CN CN201711220450.1A patent/CN107698630A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS276904B6 (en) * | 1988-08-18 | 1992-09-16 | Vyzk Ustav Farm Biochem Sp | Process for preparing crystalline 3,5,6-tri-0-benzyl-alpha-d-glucofuranose |
| CN104478955A (en) * | 2014-12-09 | 2015-04-01 | 济南卡博唐生物科技有限公司 | Preparation method of 3, 5, 6-tri-oxo-benzyl-1, 2-isopropylidene-D-glucose |
| CN106046067A (en) * | 2016-03-15 | 2016-10-26 | 山东康曼生物科技有限公司 | Synthetic method for 1,2-di-O-isopropylidene-3,5,6-tri-O-benzyl-D-glucofuranose |
| CN107365332A (en) * | 2016-05-11 | 2017-11-21 | 浙江合糖科技有限公司 | The preparation method of-O- benzyl-alpha-D- glucofuranose the glycosides of 1,2- isopropylidenes -3,5,6- three |
| CN106589015A (en) * | 2016-10-20 | 2017-04-26 | 利安隆（天津）实业有限公司 | Synthetic method of tribenoside |
Non-Patent Citations (2)
| Title |
|---|
| 叶勇，等: "《制药工艺学》", 28 February 2014 * |
| 大连理工大学: "《化工原理（下册）》", 31 December 2002 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112028950A (en) * | 2019-06-03 | 2020-12-04 | 鲁南制药集团股份有限公司 | Preparation method of tribenoside |
| CN113200823A (en) * | 2021-04-29 | 2021-08-03 | 南京威尔生物科技有限公司 | Preparation method of benzyl alcohol with low peroxide value |
| CN113200823B (en) * | 2021-04-29 | 2024-02-06 | 南京威尔生物科技有限公司 | Preparation method of benzyl alcohol with low peroxide value |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108840310B (en) | Device and process for producing hydrogen chloride by deep analysis from dilute hydrochloric acid | |
| CN107698630A (en) | A kind of preparation method of tribenoside | |
| CN104649300A (en) | Method for recovering and refining sodium bromide from dipropyl cyanoacetate mixture | |
| CN107245045A (en) | A kind of preparation method for the ground ostelin that ends | |
| CN111349049A (en) | Favipiravir and synthesis process of intermediate thereof | |
| CN102898422B (en) | Method for preparing difenoconazole | |
| CN104045669A (en) | Separation method suitable for chemical synthesis of salidroside for industrial production | |
| CN105152851A (en) | Method for separating and purifying hexachloroethane | |
| CN110668918A (en) | Chemical synthesis method of 3-chloro-1-propanol | |
| CN103497097A (en) | Substituted fluorenone and preparation method thereof | |
| CN103086845A (en) | Method for preparing L-menthol | |
| CN110343113B (en) | Preparation method of tofacitinib intermediate | |
| CN102391128A (en) | Production method of antibiotic pharmaceutical intermediate mono-p-nitro benzyl malonate | |
| CN111533688A (en) | Method for synthesizing pitavastatin calcium intermediate by using microchannel reactor | |
| CN104592003B (en) | The decoloring method of thick stearyl chloride | |
| CN103086907B (en) | Aceclofenac preparation method | |
| CN110357925A (en) | Alkaline cage compound, preparation method and catalyst | |
| CN105523915B (en) | A kind of method that high yield gas phase catalysis cracking prepares two fluoracyl fluorides | |
| CN102924255A (en) | Method for preparing 9-fluorenone through liquid-phase oxidation | |
| CN110387279B (en) | Recovery method of hydrophilic ionic liquid for removing sulfur in coal | |
| CN102363614B (en) | Method for synthesizing 2-bromothiophene | |
| CN112266364A (en) | Preparation method of tetrahydroquinoxaline compound | |
| CN106318988A (en) | Preparation method of LCZ696 key intermediate | |
| CN206279107U (en) | A kind of Steam soak dehydration technique is used for the device of synthesizing citric acid triethyl | |
| CN106588984B (en) | A kind of preparation method of 6- phosphoryls substitution phenanthridines analog derivative |
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 | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20180216 |