CN102718624A - Method for synthesizing triphenylchloromethane - Google Patents
Method for synthesizing triphenylchloromethane Download PDFInfo
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- CN102718624A CN102718624A CN2012102115161A CN201210211516A CN102718624A CN 102718624 A CN102718624 A CN 102718624A CN 2012102115161 A CN2012102115161 A CN 2012102115161A CN 201210211516 A CN201210211516 A CN 201210211516A CN 102718624 A CN102718624 A CN 102718624A
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- hydrogen chloride
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Abstract
The invention discloses a method for synthesizing triphenylchloromethane. The method comprises the following steps of: (1) mixing aluminum powder and pure benzene, and introducing hydrogen chloride gas to act on the aluminum powder till the hydrogen chloride is not absorbed any more, and thus obtaining benzene suspension of aluminum trichloride; (2) slowly adding carbon tetrachloride into the benzene suspension of the aluminum trichloride, stirring till hydrogen chloride gas is not released any more, and thus obtaining a reaction solution of an aluminum trichloride complex containing the triphenylchloromethane, wherein the hydrogen chloride gas released in the reaction process is recycled; and (3) performing post treatment on the reaction solution obtained in the (2), and thus obtaining the triphenylchloromethane. According to the method, the aluminum powder is used as an initial raw material, and only a small amount of anhydrous aluminum trichloride is required for supplementing the loss of the hydrogen chloride in the production process, so that the whole production process can be continuously implemented, equivalently most of the aluminum trichloride required to be consumed in the conventional production method is replaced by the same mole of aluminum powder, and the atom economy of the whole synthetic route is improved.
Description
(1) technical field
The present invention relates to a kind of compound method of triphenylmethyl chloride.
(2) background technology
Triphenylmethyl chloride is an important Organic Chemicals, and its main application is to be used for forming trityl ether with primary hydroxyl, realizes the selective protection of primary hydroxyl.
About the prior synthesizing method of triphenylmethyl chloride, reference Organic Syntheses, Coll.Vol.3; P.841 (1955) provide a kind of comparatively practical triphenylmethyl chloride preparation method; This method is catalyzer with the aluminum trichloride (anhydrous), is raw material with tetracol phenixin, purified petroleum benzin, and Friedel-Crafts reaction takes place; Produce the complex compound of triphenylmethyl chloride and aluminum chloride, aftertreatment obtains triphenylmethyl chloride.This method is a kind of method commonly used at present.
Because aluminum chloride and triphenylmethyl chloride form the 1:1 complex compound in the reaction process; Aluminum chloride is because of the complexing inactivation simultaneously; Therefore need on this theoretical method to consume at least 1 normal aluminum chloride, promptly produce the per kilogram the finished product and need consume 0.48 kilogram of aluminum trichloride (anhydrous).
(3) summary of the invention
The object of the invention provides a kind of improved triphenylmethyl chloride compound method; Utilize tetracol phenixin and purified petroleum benzin generation Friedel-Crafts reaction are produced in its production process by-product hydrogen chloride and aluminium powder reaction; Prepare aluminum trichloride (anhydrous), the gained aluminum trichloride (anhydrous) is used for the Friedel-Crafts reaction of catalysis tetracol phenixin and purified petroleum benzin again.
Concrete technical scheme of the present invention is:
A kind of compound method of triphenylmethyl chloride, said method comprises the steps:
(1), aluminium powder is mixed with purified petroleum benzin, feed hydrogen chloride gas and aluminium powder reaction to absorbing hydrogen chloride (pressure is in decline after promptly feeding hydrogen chloride gas) no longer, obtain the benzene suspension-s of aluminum chloride;
(2), in the benzene suspension-s of the aluminum chloride that step (1) obtains, slowly add tetracol phenixin, be stirred to and no longer emit hydrogen chloride gas, obtain containing the reaction solution of the aluminum chloride complex compound of triphenylmethyl chloride; The hydrogen chloride gas of emitting in the reaction process is recovery set usefulness then, the raw material of step (1) when the feeding gas reservoir prepares as next batch;
(3), the described reaction solution of step (2) is carried out aftertreatment, obtain triphenylmethyl chloride.
Further, the weight ratio that feeds intake of aluminium powder and purified petroleum benzin described in the step (1) is 1:13 ~ 18.
Further, step (1) can also be added aluminum trichloride (anhydrous) alternatively and mixes with aluminium powder and purified petroleum benzin, and adding of said aluminum trichloride (anhydrous) can be added alternatively.
Further, the weight ratio of adding aluminum trichloride (anhydrous) and aluminium powder in the step (1) is 0 ~ 2:1, and the implication of 0:1 is all to use aluminium powder here.
Further, step (1) is no more than at pressure reacts extremely no longer absorbing hydrogen chloride gas (pressure remains unchanged after promptly feeding hydrogen chloride gas) under the 0.5MPa condition, obtain the benzene suspension-s of aluminum chloride.
Further, the middle aluminium powder of the add-on of tetracol phenixin and step (1) is 0.98 ~ 1.1 with the total molar ratio of adding of aluminum chloride (being the theoretical molar amount of the aluminum chloride in the aluminum chloride suspension-s) in the step (2), preferred 1.0 ~ 1.1:1.
Further, under 20 ~ 60 ℃ temperature condition, add tetracol phenixin described in the step (2).
Further, the typical post-treating method of reaction solution is in the step (3): step (2) gained reaction solution is cooled to 30 ℃, adds the purified petroleum benzin dilute reaction solution, then suction 2N hydrochloric acid; Insulated and stirred 30min, standing demix is removed lower aqueous layer; Add sulfur oxychloride reflux 30min to the upper strata organic layer, add gac processings of decolouring again, filtration; Filtrate decompression concentrates and removes the solvent of 50% quality, and liquid concentrator is cooled to 10 ℃, is incubated 10 ~ 15 ℃ of crystallizations 1 hour; Filter, filter cake to constant weight, obtains triphenylmethyl chloride in 50 ℃ of vacuum-dryings; The purified petroleum benzin weight that said dilution is used is 4.0 ~ 4.2 times of tetracol phenixin charging capacity weight; Preferred 4 times; The weight of the 2N hydrochloric acid that adds is 3.4 ~ 3.5 times of tetracol phenixin charging capacity weight, and preferred 3.5 times, the weight of the gac of adding is 0.026 times of tetracol phenixin charging capacity weight; The sulfur oxychloride weight that adds is 0.77 ~ 0.79 times of tetracol phenixin charging capacity weight, preferred 0.77 times.
Further, the compound method of triphenylmethyl chloride according to the invention recommends to carry out as follows: (1) adds purified petroleum benzin, aluminium powder in the pressure reaction still with mass ratio 1:12 ~ 19, is cooled to 15 ℃ under stirring fast; Hydrogen chloride gas in the gas reservoir is fed reaction kettle, reach 0.5MPa (gauge pressure), stop to feed hydrogenchloride then until the still internal pressure; Airtight stirring 20 minutes, pressure no longer obviously descend, and continue to stir 10 minutes; Drive relief valve and emit gas reactor, the surplus hydrogenchloride of gas water absorption of residual of emitting prepares 2N hydrochloric acid, the operation that repetition " feeds hydrogen chloride gas-venting release " 10 ~ 12 times; The still internal pressure no longer descends after feeding hydrogen chloride gas this moment; Show no longer absorbing hydrogen chloride gas, promptly react completely, obtain the benzene suspension-s of aluminum chloride;
(2) in the benzene suspension-s of above-mentioned aluminum chloride, slowly add tetracol phenixin; The control temperature of reaction kettle is 20 ~ 60 ℃ in the adition process; Adding in about 2 hours finishes; Continue insulated and stirred to no longer emitting hydrogen chloride gas, the hydrogen chloride gas that produces in the reaction process all gets into air pump and imports the hydrogen chloride gas storage tank through the reaction kettle pneumatic outlet, so that recycle;
(3) step (2) reaction solution is transferred in another reaction kettle, is cooled to 30 ℃, suction purified petroleum benzin dilute reaction solution, suction 2N hydrochloric acid then; Stir standing demix after 30 minutes, divide the sub-cloud water layer, in reaction kettle, add sulfur oxychloride, reflux 30 minutes; Add gac, reflux decolour was handled 0.5 hour, filtered; Filtrate decompression concentrates steams the solvent that removes 50% quality, and the gained liquid concentrator is cooled to 10 ℃, is incubated 10 ~ 15 ℃ of stirred crystallization 1 hour; Filter, filter cake to constant weight, obtains triphenylmethyl chloride in 50 ℃ of vacuum-dryings; The purified petroleum benzin weight that said dilution is used is 4 times of tetracol phenixin charging capacity weight; The weight of the 2N hydrochloric acid that adds is 3.5 times of institute's tetracol phenixin charging capacity weight; The weight of the gac that adds is 0.026 times of tetracol phenixin charging capacity weight, and the sulfur oxychloride weight of adding is 0.77 times of tetracol phenixin charging capacity weight.
Triphenylmethyl chloride compound method according to the invention is raw material with the aluminium powder; Add a small amount of aluminum chloride alternatively; Obtain aluminum trichloride (anhydrous) with the hydrogen chloride gas precursor reactant; Then be used for the reaction of catalysis tetracol phenixin and purified petroleum benzin, the gas chlorination hydrogen that this reaction is emitted is used to prepare aluminum chloride after collecting with gas reservoir, and reaction formula is:
Compared with prior art; Beneficial effect of the present invention is mainly reflected in: novel process of the present invention uses aluminium powder to be starting raw material; Only need consume a small amount of aluminum trichloride (anhydrous) in order to replenish the hydrogenchloride loss in the production process; Can make that whole process of production can continue to carry out, the major part that is equivalent in the aluminum chloride of the required consumption of conventional production methods is replaced by equimolar aluminium powder, has improved the Atom economy of whole synthetic route.
(4) embodiment
Below in conjunction with specific embodiment the present invention is described further, but protection scope of the present invention is not limited in this:
Embodiment 1
Purified petroleum benzin 88.0kg, aluminium powder 6.8kg are added in the 300L pressure reaction still, be cooled to 15 ℃ under stirring fast.Hydrogen chloride gas in the gas reservoir is fed reaction kettle, reach 0.5MPa (gauge pressure), stop to feed hydrogenchloride then until the still internal pressure, airtight stirring 20 minutes, pressure no longer obviously descends, and continues to stir 10 minutes.Drive relief valve and emit gas reactor, the surplus hydrogenchloride of gas water absorption of residual of emitting prepares 2N hydrochloric acid.Repeat the operation 12 times of " feeding hydrogen chloride gas-venting release ", feed hydrogen chloride gas at this moment after the still internal pressure no longer descend, show no longer absorbing hydrogen chloride gas, promptly react completely, obtain the benzene suspension-s of aluminum chloride.
In the benzene suspension-s of above-mentioned aluminum chloride, slowly add tetracol phenixin 38.0kg, the control temperature of reaction kettle is 40 ~ 50 ℃ in the adition process, and adding in about 2 hours finishes, and continues insulated and stirred 6 hours, no longer emits hydrogen chloride gas this moment.The hydrogen chloride gas that produces in the reaction process all gets into air pump and imports the hydrogen chloride gas storage tank through the reaction kettle pneumatic outlet, so that recycle.
Reaction solution is transferred in another 500L reaction kettle, is cooled to 30 ℃, suction purified petroleum benzin 160kg dilute reaction solution, suction 2N hydrochloric acid 130kg then; Stir standing demix after 30 minutes, divide the sub-cloud water layer, in reaction kettle, add 30.2kg sulfur oxychloride, reflux 30 minutes; Add the 1.0kg gac, reflux decolour was handled 0.5 hour, filtered, and filtrate decompression concentrates to steam removes the 150kg solvent; The gained liquid concentrator is cooled to 10 ℃, is incubated 10 ~ 15 ℃ of stirred crystallization 1 hour, filter, filter cake in 50 ℃ of vacuum-dryings to constant weight; Obtain triphenylmethyl chloride 57.1kg, yield 83% (by tetracol phenixin), HPLC purity 99.1%.
Embodiment 2
Purified petroleum benzin 88.0kg, aluminium powder 6.2kg are added in the 300L reaction kettle, add the 3.0kg aluminum chloride, be cooled to 15 ℃ under stirring fast.Hydrogen chloride gas in the gas reservoir is fed reaction kettle, reach 0.5MPa (gauge pressure), stop to feed hydrogenchloride then until the still internal pressure, airtight stirring 20 minutes, pressure no longer obviously descends, and continues to stir 10 minutes.Drive relief valve and emit gas reactor, the surplus hydrogenchloride of gas water absorption of residual of emitting prepares 2N hydrochloric acid.Repeat the operation 11 times of " feeding hydrogen chloride gas-venting release ", feed hydrogen chloride gas at this moment after the still internal pressure no longer descend, show no longer absorbing hydrogen chloride gas, promptly react completely, obtain the benzene suspension-s of aluminum chloride.
In the benzene suspension-s of above-mentioned aluminum chloride, slowly add tetracol phenixin 38.0kg, the control temperature of reaction kettle is 20 ~ 30 ℃ in the adition process, and adding in about 2.5 hours finishes, and continues insulated and stirred 12 hours, no longer emits hydrogen chloride gas this moment.The hydrogen chloride gas that produces in the reaction process all gets into air pump and imports the hydrogen chloride gas storage tank through the reaction kettle pneumatic outlet, so that recycle.
Post-processing operation finally obtains triphenylmethyl chloride 58.5kg with embodiment 1, yield 85%, HPLC purity 99.3%.
Embodiment 3
Purified petroleum benzin 88.0kg, aluminium powder 6.6kg are added in the 300L reaction kettle, add the 1.0kg aluminum chloride, be cooled to about 15 ° of C under stirring fast.Hydrogen chloride gas in the gas reservoir is fed reaction kettle, reach 0.5MPa (gauge pressure), stop to feed hydrogenchloride then until the still internal pressure, airtight stirring 20 minutes, pressure no longer obviously descends, and continues to stir 10 minutes.Drive relief valve and emit gas reactor, the surplus hydrogenchloride of gas water absorption of residual of emitting prepares 2N hydrochloric acid.Repeat the operation 11 times of " feeding hydrogen chloride gas-venting release ", feed hydrogen chloride gas at this moment after the still internal pressure no longer descend, show no longer absorbing hydrogen chloride gas, promptly react completely, obtain the benzene suspension-s of aluminum chloride.
In the benzene suspension-s of above-mentioned aluminum chloride, slowly add tetracol phenixin 38.0kg, the control temperature of reaction kettle is 50 ~ 60 ℃ in the adition process, and adding in about 2 hours finishes, and continues insulated and stirred 6 hours, no longer emits hydrogen chloride gas this moment.The hydrogen chloride gas that produces in the reaction process all gets into air pump and imports the hydrogen chloride gas storage tank through the reaction kettle pneumatic outlet, so that recycle.
Post-processing operation finally obtains triphenylmethyl chloride 55.0kg with embodiment 1, yield 80%, HPLC purity 99.0%.
Embodiment 4
Purified petroleum benzin 88.0kg, aluminium powder 4.8kg are added in the 300L reaction kettle, add the 10.0kg aluminum chloride, be cooled to about 15 ° of C under stirring fast.Hydrogen chloride gas in the gas reservoir is fed reaction kettle, reach 0.5MPa (gauge pressure), stop to feed hydrogenchloride then until the still internal pressure, airtight stirring 20 minutes, pressure no longer obviously descends, and continues to stir 10 minutes.Drive relief valve and emit gas reactor, the surplus hydrogenchloride of gas water absorption of residual of emitting prepares 2N hydrochloric acid.Repeat the operation 10 times of " feeding hydrogen chloride gas-venting release ", feed hydrogen chloride gas at this moment after the still internal pressure no longer descend, show no longer absorbing hydrogen chloride gas, promptly react completely, obtain the benzene suspension-s of aluminum chloride.
In the benzene suspension-s of above-mentioned aluminum chloride, slowly add tetracol phenixin 42.8kg, the control temperature of reaction kettle is 40 ~ 50 ℃ in the adition process, and adding in about 2.5 hours finishes, and continues insulated and stirred 6 hours, no longer emits hydrogen chloride gas this moment.The hydrogen chloride gas that produces in the reaction process all gets into air pump and imports the hydrogen chloride gas storage tank through the reaction kettle pneumatic outlet, so that recycle.
Post-processing operation finally obtains triphenylmethyl chloride 62.0kg, yield 80%, HPLC purity 99.0% with embodiment 1 (consumption of other material is also with embodiment 1).
Claims (8)
1. the compound method of a triphenylmethyl chloride is characterized in that said method comprises the steps:
(1), aluminium powder is mixed with purified petroleum benzin, feed extremely no longer absorbing hydrogen chloride of hydrogen chloride gas and aluminium powder reaction, obtain the benzene suspension-s of aluminum chloride;
(2), in the benzene suspension-s of the aluminum chloride that step (1) obtains, slowly add tetracol phenixin, be stirred to and no longer emit hydrogen chloride gas, obtain containing the reaction solution of the aluminum chloride complex compound of triphenylmethyl chloride; The hydrogen chloride gas of emitting in the reaction process then reclaims and repeats to apply mechanically;
(3), the described reaction solution of step (2) is carried out aftertreatment, obtain triphenylmethyl chloride.
2. the compound method of triphenylmethyl chloride according to claim 1, it is characterized in that: the weight ratio that feeds intake of aluminium powder and purified petroleum benzin is 1:13 ~ 18 in the step (1).
3. the compound method of triphenylmethyl chloride according to claim 1, it is characterized in that: step (1) comprises that also adding aluminum trichloride (anhydrous) mixes with aluminium powder and purified petroleum benzin.
4. like the compound method of the said triphenylmethyl chloride of claim 3, it is characterized in that the aluminum trichloride (anhydrous) that said step (1) is added and the weight ratio of aluminium powder are 0 ~ 2:1.
5. the compound method of triphenylmethyl chloride according to claim 1, it is characterized in that: step (1) is no more than under the 0.5MPa condition at pressure reacts.
6. the compound method of triphenylmethyl chloride according to claim 1 is characterized in that: the add-on of tetracol phenixin and the said aluminium powder of step (1) and the total molar ratio of aluminum chloride added are 1 ~ 1.1:1 in the step (2).
7. the compound method of triphenylmethyl chloride according to claim 1 is characterized in that: under 20 ~ 60 ℃ of temperature condition, add tetracol phenixin in the step (2).
8. like the compound method of the said triphenylmethyl chloride of claim 6, it is characterized in that: the post-treating method of reaction solution is in the step (3): step (2) gained reaction solution is cooled to 30 ℃, adds the purified petroleum benzin dilute reaction solution, then suction 2N hydrochloric acid; Insulated and stirred 30min, standing demix is removed lower aqueous layer; In the organic layer of upper strata, add sulfur oxychloride reflux 30min, add gac processings of decolouring again, filtration; Filtrate decompression concentrates and removes the solvent of 50% quality, and liquid concentrator is cooled to 10 ℃, is incubated 10 ~ 15 ℃ of crystallizations 1 hour; Filter, filter cake to constant weight, obtains triphenylmethyl chloride in 50 ℃ of vacuum-dryings; The purified petroleum benzin weight that said dilution is used is 4 times of tetracol phenixin charging capacity weight; The weight of the 2N hydrochloric acid that adds is 3.5 times of institute's tetracol phenixin charging capacity weight; The weight of the gac that adds is 0.026 times of tetracol phenixin charging capacity weight, and the sulfur oxychloride weight of adding is 0.77 times of tetracol phenixin charging capacity weight.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107935813A (en) * | 2017-11-03 | 2018-04-20 | 苏州艾缇克药物化学有限公司 | A kind of preparation method of triphenylchloromethane |
| CN112979411A (en) * | 2021-03-09 | 2021-06-18 | 江西华飞医药科技有限公司 | Process for preparing triphenylchloromethane |
| CN113748099A (en) * | 2019-06-05 | 2021-12-03 | 临海市华南化工有限公司 | Preparation method of triphenylchloromethane |
| CN116730798A (en) * | 2023-01-29 | 2023-09-12 | 江苏飞宇医药科技股份有限公司 | Synthesis method of triphenylchloromethane |
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| JPS6357540A (en) * | 1986-08-29 | 1988-03-12 | Daicel Chem Ind Ltd | Production of triphenylchloromethane |
| WO2002042246A1 (en) * | 2000-11-27 | 2002-05-30 | Tessenderlo Chemie N.V. | Method for the preparation of dichlorodiarylmethanes |
| CN101717324A (en) * | 2009-12-07 | 2010-06-02 | 浙江工业大学 | Green synthesizing method of triphenylchloromethane |
| CN101759523A (en) * | 2010-01-12 | 2010-06-30 | 广德县中信化工厂 | Preparation method for triphenylchloromethane |
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2012
- 2012-06-21 CN CN201210211516.1A patent/CN102718624B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6357540A (en) * | 1986-08-29 | 1988-03-12 | Daicel Chem Ind Ltd | Production of triphenylchloromethane |
| WO2002042246A1 (en) * | 2000-11-27 | 2002-05-30 | Tessenderlo Chemie N.V. | Method for the preparation of dichlorodiarylmethanes |
| CN101717324A (en) * | 2009-12-07 | 2010-06-02 | 浙江工业大学 | Green synthesizing method of triphenylchloromethane |
| CN101759523A (en) * | 2010-01-12 | 2010-06-30 | 广德县中信化工厂 | Preparation method for triphenylchloromethane |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107935813A (en) * | 2017-11-03 | 2018-04-20 | 苏州艾缇克药物化学有限公司 | A kind of preparation method of triphenylchloromethane |
| CN113748099A (en) * | 2019-06-05 | 2021-12-03 | 临海市华南化工有限公司 | Preparation method of triphenylchloromethane |
| CN112979411A (en) * | 2021-03-09 | 2021-06-18 | 江西华飞医药科技有限公司 | Process for preparing triphenylchloromethane |
| CN116730798A (en) * | 2023-01-29 | 2023-09-12 | 江苏飞宇医药科技股份有限公司 | Synthesis method of triphenylchloromethane |
| CN116730798B (en) * | 2023-01-29 | 2024-03-19 | 江苏飞宇医药科技股份有限公司 | Synthesis method of triphenylchloromethane |
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Effective date of registration: 20170914 Address after: 317016 Zhejiang 317000 coastal Toumen Port District Du Sichuan Road No. 32 Patentee after: Zhejiang state rich Biotechnology Co., Ltd. Address before: 318000 rock head industrial zone, Jiaojiang District, Zhejiang, Taizhou Patentee before: Taizhou City Hwasun Pharmacuetical and Chemical Co., Ltd. |