CN109096027A - The synthetic method of triphenyl methane - Google Patents
The synthetic method of triphenyl methane Download PDFInfo
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- CN109096027A CN109096027A CN201810933278.2A CN201810933278A CN109096027A CN 109096027 A CN109096027 A CN 109096027A CN 201810933278 A CN201810933278 A CN 201810933278A CN 109096027 A CN109096027 A CN 109096027A
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- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
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Abstract
The invention discloses a kind of synthetic methods of triphenyl methane, successively the following steps are included: under the protection of inert gas, higher fatty acids or higher fatty acid salt are added in organic solvent and sodium is added；Halogeno-benzene is added dropwise again to be reacted with the mixed solution of organic solvent；Reaction gained drop, which is added in acetonitrile and the mixed solution of organic solvent, to be continued to react；Then acid solution is added or weak acid saline solution is quenched, then stand liquid separation, take organic phase that organic solvent is evaporated off, rectification under vacuum obtains triphenyl methane.Triphenyl methane is synthesized using method of the invention, raw material availability is high, avoids the use of high catalyst, not only reduces three waste discharge, reduces production cost, while product purity is high, and high income has good industrial application value.
Description
Technical field
The present invention relates to the synthetic methods of organic compound triphenyl methane.
Background technique
Triphenyl methane is important fine-chemical intermediate, is mainly used in environmental protection catalyst, photoinitiator, medicine
Intermediate, acid dyes etc..
The current synthetic method in relation to triphenyl methane has very much, there are mainly four types of:
1, phenyl boric acid synthetic method.Document (Beilstein Journal of Organic Chemistry, 2016,12,
496-504) using chlorobenzene as solvent, phenyl boric acid and benzhydrol are synthesized into triphenyl under the catalysis of trifluoromethayl sulfonic acid copper (II)
Methane, reaction yield 78%.This method reaction raw materials price is higher compared with product, and uses metal salt catalyst, and post-processing is not
It is convenient, it is difficult to realize that industrialization is used.
2, Grignard Reagent synthetic method.Document (Tetrahedron Letters, 2017,58,4,305-308) proposes halogen
Generation triphenyl methane, yield 66% are reacted with diphenyl-chloromethane under CuI catalytic action for the Grignard Reagent of benzene.Using lattice
It is low that family name's reaction prepares triphenyl methane yield, needs to use catalyst, severe reaction conditions, magnesium dosage is larger, and solid waste is difficult.
3, Friedel-Crafts reaction synthetic method.Document (Letters in Organic Chemistry, 2014,11,3,203-207)
With document (Chemische Berichte, 1925,58,1916) etc. using benzhydrol or benzoic acid in a certain amount of AlCl3's
Lower react with benzene of catalysis generates triphenyl methane.Aluminum trichloride (anhydrous) is used in reaction, its own is corrosive, and operation processing has danger
It is dangerous；Since it and product directly form the complex compound of equimolar amounts in acylation reaction, therefore the dosage in reacting is super rubs
That equivalent；Meeting water decomposition is highly exothermic reaction, and reaction product is complicated, discharges a large amount of hydrogen chloride gas, causes organic contamination, is hydrolyzed
The acid solution rich in aluminium is generated afterwards to be industrially difficult to handle.
4, catalysis synthesis process.Document (Journal of the American Chemical Society, 2014,136,
Diphenyl methane and chlorobenzene 17,6276-6287) are synthesized into triphenyl methane in organic palladium catalyst reaction 12h.This method
Reaction time is more long, needs to use organo-metallic catalyst, it is difficult to realize that industrialization is used.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of efficient, economical, green, being suitable for industrialization production requirements three
The synthetic method of phenylmethane.
In order to solve the above technical problem, the present invention provides the synthetic methods of triphenyl methane, successively the following steps are included:
(1), using following either type:
Mode one, under the protection of inert gas, it is (high that higher fatty acids or higher fatty acid salt are added in organic solvent
Grade fatty acid or higher fatty acid salt are a small amount of) and sodium (metallic sodium) is added, first it is heated to reflux (about 90~140
DEG C) 30~60min of stirring, then stop heating, high-speed stirred is until be cooled to room temperature；
Mode two, under the protection of inert gas, in solvent I be added sodium (metallic sodium), be first heated to reflux and stir
30~60min is mixed, heating is then stopped, until being cooled to room temperature, filtering obtains graininess sodium (sodium sand) high-speed stirred；Institute
State and organic solvent be added in graininess sodium (sodium sand), and be added higher fatty acids or higher fatty acid salt (higher fatty acids or
Higher fatty acid salt is a small amount of)；
(2), under the protection of inert gas, be added dropwise into liquid obtained by step (1) (being slowly added dropwise) halogeno-benzene with it is organic molten
The mixed solution of agent, in 20~40 DEG C (preferably 20~30 DEG C) 1~2h of reaction after being added dropwise；
The molar ratio of sodium is 1:1.6~2.2 (preferably 1:1.9~2) in halogeno-benzene and step (1)；
(3), under the protection of inert gas, drop obtained by step (2) is added and (is slowly added dropwise) to acetonitrile and organic solvent
Mixed solution in, after being added dropwise under -20~40 DEG C (preferably 10~20 DEG C) react 1~3h；
The molar ratio of halogeno-benzene and acetonitrile in step (2) is 1:0.3~0.6 (preferably 1:0.4~0.5)；
(4), acid solution is added in the resulting reaction solution of step (3) or weak acid saline solution (such as aqueous ammonium chloride solution) is quenched
It goes out；
(5), liquid obtained by step (4) is stood into liquid separation, takes organic phase (being located at upper layer) that organic solvent, rectification under vacuum is evaporated off
(196 DEG C, 10Torr) obtain triphenyl methane (yellow solid).
Remarks explanation: the standing resulting water phase of liquid separation is sodium salt (for example, NaCl) aqueous solution.
The improvement of synthetic method as triphenyl methane of the invention:
In the step 2), the temperature of control reaction system is no more than 40 DEG C during being added dropwise；
In the step 3), time for adding is 30 ± 10min.
The further improvement of synthetic method as triphenyl methane of the invention:
Halogeno-benzene in the step (2) is chlorobenzene, bromobenzene, iodobenzene.
The further improvement of synthetic method as triphenyl methane of the invention:
In the step (1),
Higher fatty acids is oleic acid, dodecyl benzene sulfonic acid, stearic acid, linolenic acid；
Higher fatty acid salt is enuatrol, dodecyl sodium sulfate, odium stearate；
The higher fatty acid salt of 2~4g of higher fatty acids or adapted of 2~4ml of organic solvent adapted of every 300mL；
The sodium of 0.5~1.5mol of organic solvent adapted (preferably 1mol) of every 300mL；
In the step (2), the organic solvent of 50~80mL of every 0.5~0.6mol halogeno-benzene adapted；
In the step (3), the organic solvent of 30~50mL of every 0.2~0.25mol acetonitrile adapted；
In the step (4), acid solution or weak acid saline solution: organic molten in step (1), step (2) and step (3)
The volume ratio of the sum of dosage of agent=1:3.5~6 (preferably 1:3.8~4.2).
The further improvement of synthetic method as triphenyl methane of the invention:
In the step (4), acid solution is that mass concentration is 8~12% (preferably 10%) aqueous hydrochloric acid solutions, salt of weak acid
Aqueous solution is the aqueous ammonium chloride solution that mass concentration is 18~22% (preferably 20%).
The further improvement of synthetic method as triphenyl methane of the invention:
In the step (1):
Organic solvent used in mode one is toluene, dimethylbenzene, Isosorbide-5-Nitrae-dioxane, normal heptane, is had used in mode two
Solvent is tetrahydrofuran, ether；
Organic solvent used in the same step of organic solvent (1) used in the step (2), (3).
The further improvement of synthetic method as triphenyl methane of the invention:
In the mode two of the step (1): the sodium of I 0.5~1.5mol of adapted of solvent of every 300mL；Solvent I be toluene,
Dimethylbenzene, 1,4- dioxane, normal heptane.
The further improvement of synthetic method as triphenyl methane of the invention:
In the step (1), the revolving speed of high-speed stirred is 500~1500 revs/min.
In the present invention, under the protection of inert gas, that is, representing is in anhydrous, anaerobic and to have the item of inert gas shielding
Under part；The preferred nitrogen of inert gas.
Triphenyl methane prepared by the present invention, MS map are as shown in Figure 1.
The present invention is synthesized using sodium metal reaction, and price is cheap compared with magnesium, is reacted solid waste NaCl of generation etc. and is easier to recycling benefit
With；It joined a small amount of higher fatty acids or higher fatty acid salt in reaction, make emulsifier and catalyst, keep reaction more stable,
The generation of biphenyl and polyphenyls is reduced, reaction conversion ratio and selectivity are high.The higher fatty acids or higher aliphatic that this method uses
Hydrochlorate is easier to obtain, cheap, and required temperature condition is easier to reach, and energy consumption is smaller, and industrial applications prospect can
It sees.Use acetonitrile and chlorobenzene for raw material, cost of material is lower.
Compared with prior art, the present invention having following technical advantage:
(1) processing step is simply clear, post-processes more convenient；
(2) green, metallic sodium can be reacted completely, and waste discharge is few；
(3) reaction process energy consumption is small, and synthesis under normal pressure is lower to equipment requirement.
In conclusion synthesizing triphenyl methane using method of the invention, raw material availability is high, avoids high catalyst
Use, not only reduce three waste discharge, reduce production cost, while product purity is high, high income has industry well
Application value.
Detailed description of the invention
Specific embodiments of the present invention will be described in further detail with reference to the accompanying drawing.
Fig. 1 is the MS map of triphenyl methane.
Upper figure is sample introduction mass spectrogram；Middle figure is database matching mass spectrogram, and the following figure is matter of matching structural formula.
Specific embodiment
The present invention is described further combined with specific embodiments below, but protection scope of the present invention is not limited in
This.
In following embodiments: under the protection of inert gas (nitrogen), that is, representing is in anhydrous, anaerobic and to have nitrogen protection
Under conditions of；The stirring that do not inform clearly is 150~300 revs/min of conventional rotating speed；High-speed stirred refer to >=500 turns/
The stirring of component velocity revolving speed.
Embodiment 1, the synthetic method of triphenyl methane, successively follow the steps below:
(1), under the protection of inert gas (nitrogen), into reaction unit be added 23g (1mol) sodium, 300mL toluene,
4mL oleic acid is warming up to (110 DEG C) of reflux stirrings, stops heating after the 1h that flows back, high-speed stirred is until be cooled to room temperature.
(2), under the protection of inert gas (nitrogen), 56g (0.5mol) chlorobenzene is slowly added dropwise into liquid obtained by step (1)
With 50mL toluene mixed solution, the temperature of control reaction system is no more than 40 DEG C during being added dropwise；In 30 DEG C after being added dropwise, instead
Answer 2h.
(3), under the protection of inert gas (nitrogen), liquid obtained by step (2) is slowly added dropwise to 10g (0.25mol) second
In the mixed solution of nitrile and 30mL toluene, time for adding 30min is maintained at 10 DEG C of reaction 3h, that is, stops after being added dropwise.
(4), 100mL20% aqueous ammonium chloride solution is added in the resulting reaction solution of step (3) to be quenched.
(5), liquid obtained by step (4) is stood into liquid separation, takes organic phase (being located at upper layer) to be evaporated off toluene (110 DEG C), decompression essence
It evaporates (196 DEG C, 10Torr) and obtains triphenyl methane (yellow solid).
Yield is 85.8%, purity 98.5%.
Note: the resulting water phase of liquid separation is purified, nanofiltration, minimizing, the post-processing of evaporative crystallization, and purity >=99% can be obtained
NaCl.
Embodiment 2, the synthetic method of triphenyl methane, successively follow the steps below:
(1), under the protection of inert gas (nitrogen), into reaction unit be added 23g (1mol) sodium, 300mL dimethylbenzene,
2g odium stearate is warming up to (137 DEG C) of reflux stirrings, stops heating after the 1h that flows back, stirring is until be cooled to room temperature at high speed.
(2), under the protection of inert gas (nitrogen), 56g (0.5mol) chlorobenzene is slowly added dropwise into liquid obtained by step (1)
With 50mL dimethylbenzene mixed solution, the temperature of control reaction system is no more than 40 DEG C during being added dropwise；In 30 DEG C after being added dropwise,
React 2h.
(3), under the protection of inert gas (nitrogen), liquid obtained by step (2) is slowly added dropwise to 8g (0.2mol) acetonitrile
In the mixed solution of 30mL dimethylbenzene, time for adding 30min is maintained at 10 DEG C of reaction 3h, that is, stops after being added dropwise.
(4), 100mL10% hydrochloric acid solution is added in the resulting reaction solution of step (3) to be quenched.
(5), liquid obtained by step (4) is stood into liquid separation, takes organic phase (being located at upper layer) to be evaporated off dimethylbenzene (137 DEG C), depressurizes
Rectifying (196 DEG C, 10Torr) obtains triphenyl methane (yellow solid).
Yield is 80.3%, purity 98.0%.
Embodiment 3, the synthetic method of triphenyl methane, successively follow the steps below:
(1), under the protection of inert gas (nitrogen), into reaction unit be added 23g (1mol) sodium, 300mL toluene,
4mL oleic acid is warming up to (110 DEG C) of reflux stirrings, stops heating after the 1h that flows back, high-speed stirred is until be cooled to room temperature.
(2), under the protection of inert gas (nitrogen), 78.5g (0.5mol) bromine is slowly added dropwise into liquid obtained by step (1)
Benzene and 80mL toluene mixed solution, the temperature of control reaction system is no more than 40 DEG C during being added dropwise；In 30 DEG C after being added dropwise,
React 2h.
(3), under the protection of inert gas (nitrogen), liquid obtained by step (2) is slowly added dropwise to 10g (0.25mol) second
In the mixed solution of nitrile and 30mL toluene, time for adding 30min is maintained at 10 DEG C of reaction 3h after being added dropwise, that is, stops anti-
It answers.
(4), 100mL20% aqueous ammonium chloride solution is added in the resulting reaction solution of step (3) to be quenched.
(5), liquid obtained by step (4) is stood into liquid separation, takes organic phase (being located at upper layer) to be evaporated off toluene (110 DEG C), decompression essence
It evaporates (196 DEG C, 10Torr) and obtains triphenyl methane (yellow solid).
Yield is 84.8%, purity 98.1%.
Embodiment 4, the synthetic method of triphenyl methane, successively follow the steps below:
(1), under the protection of inert gas (nitrogen), 23g (1mol) sodium, 300mL toluene, 2g are added into reaction unit
Neopelex is warming up to (110 DEG C) of reflux stirrings, stops heating after the 1h that flows back, high-speed stirred is until be cooled to room temperature.
(2), under the protection of inert gas (nitrogen), 67.2g (0.6mol) chlorine is slowly added dropwise into liquid obtained by step (1)
Benzene and 70mL toluene mixed solution, the temperature of control reaction system is no more than 40 DEG C during being added dropwise；In 30 DEG C after being added dropwise,
React 2h.
(3), under the protection of inert gas (nitrogen), liquid obtained by step (2) is slowly added dropwise to 8g (0.2mol) acetonitrile
In the mixed solution of 30mL toluene, time for adding 30min is maintained at 10 DEG C of reaction 3h, that is, stops after being added dropwise.
(4), 100mL10% hydrochloric acid solution is added in the resulting reaction solution of step (3) to be quenched.
(5), liquid obtained by step (4) is stood into liquid separation, takes organic phase (being located at upper layer) to be evaporated off toluene (110 DEG C), decompression essence
It evaporates (196 DEG C, 10Torr) and obtains triphenyl methane (yellow solid).
Yield is 82.3%, purity 98.2%.
Embodiment 5, the synthetic method of triphenyl methane, successively follow the steps below:
(1), under the protection of inert gas (nitrogen), 23g (1mol) sodium, 300mL toluene are added into reaction unit, rises
Temperature stops heating after the 1h that flows back, after high-speed stirred is until be cooled to room temperature, filters out sodium sand particle to (110 DEG C) stirrings of reflux,
300mL tetrahydrofuran, 4g odium stearate are added in sodium sand particle.
(2), under the protection of inert gas (nitrogen), 56g (0.5mol) chlorobenzene is slowly added dropwise into liquid obtained by step (1)
With 50mL tetrahydrofuran mixed solution, the temperature of control reaction system is no more than 40 DEG C during being added dropwise；In 20 after being added dropwise
DEG C, react 2h.
(3), under the protection of inert gas (nitrogen), liquid obtained by step (2) is slowly added dropwise to 10g (0.25mol) second
In the mixed solution of nitrile and 30mL tetrahydrofuran, time for adding 30min is maintained at 10 DEG C of reaction 3h, that is, stops after being added dropwise
Only react.
(4), 100mL20% aqueous ammonium chloride solution is added in the resulting reaction solution of step (3) to be quenched.
(5), liquid obtained by step (4) is stood into liquid separation, takes organic phase (being located at upper layer) to be evaporated off tetrahydrofuran (66 DEG C), depressurizes
Rectifying (196 DEG C, 10Torr) obtains triphenyl methane (yellow solid).
Yield is 84.9%, purity 98.9%.
Embodiment 6, the synthetic method of triphenyl methane, successively follow the steps below:
(1), under the protection of inert gas (nitrogen), 23g (1mol) sodium, 300mL1,4- bis- are added into reaction unit
Six ring of oxygen, 2mL oleic acid are warming up to (101 DEG C) of reflux stirrings, stop heating after the 1h that flows back, high-speed stirred is until be cooled to room temperature.
(2), under the protection of inert gas (nitrogen), 67.2g (0.6mol) chlorine is slowly added dropwise into liquid obtained by step (1)
Benzene and 70mL1,4- dioxane mixed solution, the temperature of control reaction system is no more than 40 DEG C during being added dropwise；It is added dropwise
Afterwards in 30 DEG C, 2h is reacted.
(3), under the protection of inert gas (nitrogen), liquid obtained by step (2) is slowly added dropwise to 10g (0.25mol) second
Nitrile and 30mL1, in the mixed solution of 4- dioxane, time for adding 30min is maintained at 10 DEG C of reaction 3h after being added dropwise,
Stop reaction.
(4), 100mL20% aqueous ammonium chloride solution is added in the resulting reaction solution of step (3) to be quenched.
(5), liquid obtained by step (4) is stood into liquid separation, takes organic phase (being located at upper layer) that Isosorbide-5-Nitrae-dioxane (101 is evaporated off
DEG C), rectification under vacuum (196 DEG C, 10Torr) obtains triphenyl methane (yellow solid).
Yield is 83.8%, purity 98.4%.
Comparative example 1,
Cancel " reaction for being warming up to reflux " in 1 step of embodiment (1),
That is, step (2) is changed to following content: under the protection of inert gas (nitrogen), being added into reaction unit
23g (1mol) sodium, 300mL toluene, 4mL oleic acid, are then directly slowly added dropwise 56g (0.5mol) chlorobenzene and 50mL to reaction unit
Toluene mixed solution；Reaction condition is constant, i.e., are as follows: the temperature of control reaction system is no more than 40 DEG C during being added dropwise；It drips
In 30 DEG C after finishing, 2h is reacted.Remaining is equal to embodiment 1.
Acquired results are as follows: yield 38.2%, purity 88.1%.
Comparative example 2,
Cancel the use of " the 4mL oleic acid " in 1 step of embodiment (1), remaining is equal to embodiment 1.
Acquired results are as follows: yield 63.5%, purity 86.3%.
Comparative example 3,
Cancel the protection of 1 step of embodiment (1), (2), inert gas (nitrogen) in (3)；Remaining is equal to embodiment 1.
Acquired results are as follows: yield 77.7%, purity 96.6%.
Comparative example 4,
" the 100mL10% hydrochloric acid solution " of step (4) in embodiment 2 is changed to conventional concentrated hydrochloric acid, the mole dosage of HCL
It remains unchanged；Remaining is equal to embodiment 2.
Acquired results are as follows: yield 73.5%, purity 97.3%.
The above list is only a few specific embodiments of the present invention for finally, it should also be noted that.Obviously, this hair
Bright to be not limited to above embodiments, acceptable there are many deformations.Those skilled in the art can be from present disclosure
All deformations for directly exporting or associating, are considered as protection scope of the present invention.
Claims (8)
1. the synthetic method of triphenyl methane, it is characterized in that successively the following steps are included:
(1), using following either type:
Mode one, under the protection of inert gas, higher fatty acids or higher fatty acid salt, Yi Jijia are added in organic solvent
Enter sodium, be first heated to 30~60min of return stirring, then stop heating, high-speed stirred is until be cooled to room temperature；
Mode two, under the protection of inert gas, sodium is added in solvent I, is first heated to 30~60min of return stirring,
Then stop heating, for high-speed stirred until being cooled to room temperature, filtering obtains graininess sodium；Being added in the graininess sodium has
Solvent, and higher fatty acids or higher fatty acid salt is added；
(2), under the protection of inert gas, the mixed solution of halogeno-benzene and organic solvent, drop are added dropwise into liquid obtained by step (1)
In 20~40 DEG C of 1~2h of reaction after adding；
The molar ratio of sodium is 1:1.6~2.2 in halogeno-benzene and step (1)；
(3), under the protection of inert gas, drop obtained by step (2) is added in the mixed solution of acetonitrile and organic solvent, is dripped
1~3h is reacted after adding at -20~40 DEG C；
The molar ratio of halogeno-benzene and acetonitrile in step (2) is 1:0.3~0.6；
(4), acid solution is added in the resulting reaction solution of step (3) or weak acid saline solution is quenched；
(5), liquid obtained by step (4) is stood into liquid separation, takes organic phase that organic solvent is evaporated off, rectification under vacuum obtains triphenyl methane.
2. the synthetic method of triphenyl methane according to claim 1, it is characterized in that:
In the step 2), the temperature of control reaction system is no more than 40 DEG C during being added dropwise；
In the step 3), time for adding is 30 ± 10min.
3. the synthetic method of triphenyl methane according to claim 1 or 2, it is characterized in that:
Halogeno-benzene in the step (2) is chlorobenzene, bromobenzene, iodobenzene.
4. the synthetic method of triphenyl methane according to claim 3, it is characterized in that:
In the step (1),
Higher fatty acids is oleic acid, dodecyl benzene sulfonic acid, stearic acid, linolenic acid；
Higher fatty acid salt is enuatrol, dodecyl sodium sulfate, odium stearate；
The higher fatty acid salt of 2~4g of higher fatty acids or adapted of 2~4ml of organic solvent adapted of every 300mL；
The sodium of 0.5~1.5mol of organic solvent adapted of every 300mL；
In the step (2), the organic solvent of 50~80mL of every 0.5~0.6mol halogeno-benzene adapted；
In the step (3), the organic solvent of 30~50mL of every 0.2~0.25mol acetonitrile adapted；
In the step (4), acid solution or weak acid saline solution: step (1), step (2) and the organic solvent in step (3)
The sum of dosage=1:3.5~6 volume ratio.
5. the synthetic method of triphenyl methane according to claim 3, it is characterized in that:
In the step (4), acid solution is that mass concentration is 8~12% aqueous hydrochloric acid solutions, and weak acid saline solution is mass concentration
For 18~22% aqueous ammonium chloride solution.
6. the synthetic method of triphenyl methane according to claim 3, it is characterized in that:
In the step (1):
Organic solvent used in mode one is toluene, dimethylbenzene, Isosorbide-5-Nitrae-dioxane, normal heptane, organic molten used in mode two
Agent is tetrahydrofuran, ether；
Organic solvent used in the same step of organic solvent (1) used in the step (2), (3).
7. the synthetic method of triphenyl methane according to claim 6, it is characterized in that:
In the mode two of the step (1): the sodium of I 0.5~1.5mol of adapted of solvent of every 300mL；Solvent I is toluene, diformazan
Benzene, 1,4- dioxane, normal heptane.
8. the synthetic method of triphenyl methane according to claim 3, it is characterized in that:
In the step (1), the revolving speed of high-speed stirred is 500~1500 revs/min.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101759523A (en) * | 2010-01-12 | 2010-06-30 | 广德县中信化工厂 | Preparation method for triphenylchloromethane |
| WO2016066835A1 (en) * | 2014-10-30 | 2016-05-06 | Córdova Armando | A mild catalytic reduction of c-o bonds and c=o bonds using a recyclable catalyst system |
| WO2016093175A1 (en) * | 2014-12-12 | 2016-06-16 | 国立大学法人名古屋大学 | Method for producing tri(hetero)arylacetonitrile compound |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101759523A (en) * | 2010-01-12 | 2010-06-30 | 广德县中信化工厂 | Preparation method for triphenylchloromethane |
| WO2016066835A1 (en) * | 2014-10-30 | 2016-05-06 | Córdova Armando | A mild catalytic reduction of c-o bonds and c=o bonds using a recyclable catalyst system |
| WO2016093175A1 (en) * | 2014-12-12 | 2016-06-16 | 国立大学法人名古屋大学 | Method for producing tri(hetero)arylacetonitrile compound |
Non-Patent Citations (2)
| Title |
|---|
| JINGSONG YOU ET AL.: "P(i-BuNCH2CH2)3N: An Efficient Ligand for the Direct r-Arylation of Nitriles with Aryl Bromides", 《JOURNAL OF ORGANIC CHEMISTRY》 * |
| 陈慧晴等: "过渡金属配合物催化乙腈碳碳单键断裂的研究进展", 《无机化学学报》 * |
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