CN109134539A - A kind of method and apparatus preparing tri-phenyl-ethyl phosphonium bromide - Google Patents

A kind of method and apparatus preparing tri-phenyl-ethyl phosphonium bromide Download PDF

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Publication number
CN109134539A
CN109134539A CN201811292584.9A CN201811292584A CN109134539A CN 109134539 A CN109134539 A CN 109134539A CN 201811292584 A CN201811292584 A CN 201811292584A CN 109134539 A CN109134539 A CN 109134539A
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China
Prior art keywords
phenyl
tri
phosphonium bromide
reaction
bromoethane
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张朵
龙健朝
刘宇
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Kent Jiangxi Chemical Co Ltd
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Kent Jiangxi Chemical Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/54Quaternary phosphonium compounds
    • C07F9/5442Aromatic phosphonium compounds (P-C aromatic linkage)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to tri-phenyl-ethyl phosphonium bromide preparation technical fields, more particularly to a kind of method and apparatus for preparing tri-phenyl-ethyl phosphonium bromide, the following steps are included: step 1, pretreatment: it is at 20-30 DEG C that bromoethane, which is placed in temperature, 45-55min is stood, then carries out microwave treatment, then again by triphenyl phosphonium at 30-40 DEG C, 25-35min is stood, it is spare;Bromoethane, triphenyl phosphonium in step 1 is added to absolute ethanol according to weight ratio 2:1, is subsequently sent in reaction kettle by step 2.Bromoethane first passes through pretreatment, improve the order of contact with triphenyl phosphonium, increase reaction effect, reaction kettle hybrid reaction then is added, yield and purity significantly improve, the mutual proportion between raw material, and pretreatment, reaction rate and reaction yield are improved, is greatly improved compared with the existing technology.

Description

A kind of method and apparatus preparing tri-phenyl-ethyl phosphonium bromide
Technical field
The present invention relates to tri-phenyl-ethyl phosphonium bromide preparation technical fields, and in particular to a kind of to prepare triphenyl ethyl phosphonium bromide The method and apparatus of Phosphonium.
Background technique
Tri-phenyl-ethyl phosphonium bromide is also known as Ethyltriphenylphosphonium brimide, and molecular formula is CHBrP, molecular weight are 371.2506, material incentive eyes, respiratory system and the skin, existing Chinese patent literature (publication number: CN106832795A) A kind of high-temperature resistant anti-corrosive vinylite is disclosed, according to parts by weight includes: 33-36 parts of bisphenol A formaldehyde epoxy resin, it is organic 10-12 parts of silicon modified epoxy resin, 2-4 parts of acrylic acid modified alkyd resin, 15-16 parts of methacrylic acid, acrylic acid 10-13 Part, 11-14 parts of fumaric acid, 15-18 parts of maleic anhydride, 0.5-1 parts of tri-phenyl-ethyl phosphonium bromide, hydroquinone 0.2-0.5 Part, 40-43 parts of styrene, high temperature modified dose 2-10 parts, Chinese patent literature (publication number: CN106832795A) discloses one kind Rapid photocuring vinylite.According to parts by weight include: Bisphenol F/47-50 parts of resorcinol copoly type epoxy resin, has 10-15 parts of machine silicon modified epoxy resin, 3-5 parts of butyl ether benzoguanamine resin, 15-16 parts of methacrylic acid, acrylic acid 14- 18 parts, 6-8 parts of fumaric acid, 9-15 parts of maleic anhydride, 0.5-1 parts of tri-phenyl-ethyl phosphonium bromide, hydroquinone 0.3-0.6 Part, it is 45-48 parts of styrene, 0.2-0.5 parts of photoinitiator, 2-5 parts of reactive diluent, light-initiated compounding agent 0.3-0.8, compound to change Property 5-8 parts of agent, the two document gives raw material of the tri-phenyl-ethyl phosphonium bromide as invention, but does not provide corresponding preparation Method.
Do not occur the preparation method of tri-phenyl-ethyl phosphonium bromide in existing literature also, therefore the present invention further studies preparation Preparation method out.
Summary of the invention
The purpose of the present invention is to provide a kind of method and apparatus for preparing tri-phenyl-ethyl phosphonium bromide, to solve above-mentioned back The problem of being proposed in scape technology.
To achieve the above object, the invention provides the following technical scheme:
A method of preparing tri-phenyl-ethyl phosphonium bromide, comprising the following steps:
Step 1, pretreatment: it is to stand 45-55min, then carry out microwave treatment at 20-30 DEG C that bromoethane, which is placed in temperature,
Then again by triphenyl phosphonium at 30-40 DEG C, 25-35min is stood, it is spare;
Bromoethane, triphenyl phosphonium in step 1 is added to absolute ethanol according to weight ratio 2:1, is subsequently sent to by step 2 In reaction kettle, reaction temperature is 90-110 DEG C, reacts 20-30min, then adds bromobenzene, and the reaction was continued 1-2h then will Temperature rises to 160-170 DEG C, keeps the temperature 20-30min to get tri-phenyl-ethyl phosphonium bromide of the invention.
It is as further scheme of the invention: the microwave treatment conditions are as follows: microwave frequency 300-400MHz, power are 700-780W, microwave treatment mode stops 1-2min after being microwave treatment 35-45s, then stops after carrying out microwave treatment 20-30s 45-55s, 2-3 times repeatedly.
It is as further scheme of the invention: the microwave treatment conditions are as follows: microwave frequency 350MHz, power are 740W, microwave treatment mode stops 1.5min after being microwave treatment 40s, then stops 50s after carrying out microwave treatment 25s, so anti- It is 3 times multiple.
Be as further scheme of the invention: bromobenzene weight is bromoethane, triphenyl phosphonium gross weight in the step 2 The 10-20% of amount.
Be as further scheme of the invention: bromobenzene weight is bromoethane, triphenyl phosphonium gross weight in the step 2 The 15% of amount.
The present invention also provides a kind of equipment for being used to prepare tri-phenyl-ethyl phosphonium bromide, the equipment includes that pretreatment is set Standby, pre-processing device includes first reactor and second reactor, and the pre-processing device is connected to reaction kettle.
It is as further scheme of the invention: is equipped with microwave reaction device in the first reactor.
Compared with prior art, the present invention has following the utility model has the advantages that bromoethane is first first passed through pretreatment by the present invention, The order of contact with triphenyl phosphonium is improved, increases reaction effect, then adds reaction kettle hybrid reaction, yield and purity obtain It significantly improves, the mutual proportion between raw material, and pretreatment, reaction rate and reaction yield is improved, relative to existing skill Art is greatly improved.
Detailed description of the invention
Fig. 1 is the device structure schematic diagram that the present invention prepares tri-phenyl-ethyl phosphonium bromide.
In figure: 1- pre-processing device;2- first reactor;3- second reactor;4- microwave reaction device;5- reaction kettle.
Specific embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete Site preparation description, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.It is based on Embodiment in the present invention, it is obtained by those of ordinary skill in the art without making creative efforts every other Embodiment shall fall within the protection scope of the present invention.
Embodiment 1:
Referring to Fig. 1, a kind of method for preparing tri-phenyl-ethyl phosphonium bromide of the present embodiment, comprising the following steps:
Step 1, pretreatment: it is to stand 45min, then carry out microwave treatment at 20 DEG C that bromoethane, which is placed in temperature,
Then again by triphenyl phosphonium at 30 DEG C, 25min is stood, it is spare;
Bromoethane, triphenyl phosphonium in step 1 is added to absolute ethanol according to weight ratio 2:1, is subsequently sent to by step 2 In reaction kettle, reaction temperature is 90 DEG C, reacts 20min, then adds bromobenzene, and the reaction was continued 1h then rises to temperature 160 DEG C, 20min is kept the temperature to get tri-phenyl-ethyl phosphonium bromide of the invention.
The microwave treatment conditions of the present embodiment are as follows: microwave frequency 300MHz, power 700-W, microwave treatment mode are micro- Stop 1min after wave processing 35s, then stops 45s after carrying out microwave treatment 20s, 2 times repeatedly.
In the step of the present embodiment two bromobenzene weight be bromoethane, triphenyl phosphonium total weight 10%.
A kind of equipment being used to prepare tri-phenyl-ethyl phosphonium bromide, the equipment include pre-processing device 1, pre-processing device 1 includes first reactor 2 and second reactor 3, and the pre-processing device is connected to reaction kettle 5.
Microwave reaction device 4 is equipped in the first reactor 2 of the present embodiment.
Embodiment 2:
A kind of method preparing tri-phenyl-ethyl phosphonium bromide of the present embodiment, comprising the following steps:
Step 1, pretreatment: it is to stand 55min, then carry out microwave treatment at 30 DEG C that bromoethane, which is placed in temperature,
Then again by triphenyl phosphonium at 40 DEG C, 35min is stood, it is spare;
Bromoethane, triphenyl phosphonium in step 1 is added to absolute ethanol according to weight ratio 2:1, is subsequently sent to by step 2 In reaction kettle, reaction temperature is 110 DEG C, reacts 30min, then adds bromobenzene, and the reaction was continued 2h then rises to temperature 170 DEG C, 30min is kept the temperature to get tri-phenyl-ethyl phosphonium bromide of the invention.
The microwave treatment conditions of the present embodiment are as follows: microwave frequency 400MHz, power 780W, microwave treatment mode are microwave Stop 2min after processing 45s, then stops 55s after carrying out microwave treatment 30s, 3 times repeatedly.
In the step of the present embodiment two bromobenzene weight be bromoethane, triphenyl phosphonium total weight 20%.
A kind of equipment being used to prepare tri-phenyl-ethyl phosphonium bromide, the equipment include pre-processing device 1, pre-processing device 1 includes first reactor 2 and second reactor 3, and the pre-processing device is connected to reaction kettle 5.
Microwave reaction device 4 is equipped in the first reactor 2 of the present embodiment.
Embodiment 3:
A kind of method preparing tri-phenyl-ethyl phosphonium bromide of the present embodiment, comprising the following steps:
Step 1, pretreatment: it is to stand 50min, then carry out microwave treatment at 25 DEG C that bromoethane, which is placed in temperature,
Then again by triphenyl phosphonium at 35 DEG C, 30min is stood, it is spare;
Bromoethane, triphenyl phosphonium in step 1 is added to absolute ethanol according to weight ratio 2:1, is subsequently sent to by step 2 In reaction kettle, reaction temperature is 100 DEG C, reacts 25min, then adds bromobenzene, the reaction was continued 1.5h, then by temperature liter To 165 DEG C, 25min is kept the temperature to get tri-phenyl-ethyl phosphonium bromide of the invention.
The microwave treatment conditions of the present embodiment are as follows: microwave frequency 350MHz, power 740W, microwave treatment mode are microwave Stop 1.5min after processing 40s, then stops 50s after carrying out microwave treatment 25s, 3 times repeatedly.
In the step of the present embodiment two bromobenzene weight be bromoethane, triphenyl phosphonium total weight 15%.
A kind of equipment being used to prepare tri-phenyl-ethyl phosphonium bromide, the equipment include pre-processing device 1, pre-processing device 1 includes first reactor 2 and second reactor 3, and the pre-processing device is connected to reaction kettle 5.
Microwave reaction device 4 is equipped in the first reactor 2 of the present embodiment.
Embodiment 4:
A kind of method preparing tri-phenyl-ethyl phosphonium bromide of the present embodiment, comprising the following steps:
Step 1, pretreatment: it is to stand 48min, then carry out microwave treatment at 24 DEG C that bromoethane, which is placed in temperature,
Then again by triphenyl phosphonium at 34 DEG C, 28min is stood, it is spare;
Bromoethane, triphenyl phosphonium in step 1 is added to absolute ethanol according to weight ratio 2:1, is subsequently sent to by step 2 In reaction kettle, reaction temperature is 98 DEG C, reacts 24min, then adds bromobenzene, the reaction was continued 1-2h, then by temperature liter To 164 DEG C, 24min is kept the temperature to get tri-phenyl-ethyl phosphonium bromide of the invention.
The microwave treatment conditions of the present embodiment are as follows: microwave frequency 330MHz, power 730W, microwave treatment mode are microwave Stop 1.5min after processing 39s, then stops 44s after carrying out microwave treatment 24s, 3 times repeatedly.
In the step of the present embodiment two bromobenzene weight be bromoethane, triphenyl phosphonium total weight 14%.
A kind of equipment being used to prepare tri-phenyl-ethyl phosphonium bromide, the equipment include pre-processing device 1, pre-processing device 1 includes first reactor 2 and second reactor 3, and the pre-processing device is connected to reaction kettle 5.
Microwave reaction device 4 is equipped in the first reactor 2 of the present embodiment.
Embodiment 5:
A kind of method preparing tri-phenyl-ethyl phosphonium bromide of the present embodiment, comprising the following steps:
Step 1, pretreatment: it is to stand 53min, then carry out microwave treatment at 28 DEG C that bromoethane, which is placed in temperature,
Then again by triphenyl phosphonium at 38 DEG C, 33min is stood, it is spare;
Bromoethane, triphenyl phosphonium in step 1 is added to absolute ethanol according to weight ratio 2:1, is subsequently sent to by step 2 In reaction kettle, reaction temperature is 108 DEG C, reacts 28min, then adds bromobenzene, the reaction was continued 1.8h, then by temperature liter To 168 DEG C, 28min is kept the temperature to get tri-phenyl-ethyl phosphonium bromide of the invention.
The microwave treatment conditions of the present embodiment are as follows: microwave frequency 380MHz, power 760W, microwave treatment mode are microwave Stop 1.8min after processing 43s, then stops 53s after carrying out microwave treatment 28s, 3 times repeatedly.
In the step of the present embodiment two bromobenzene weight be bromoethane, triphenyl phosphonium total weight 18%.
Referring to Fig. 1, a kind of equipment for being used to prepare tri-phenyl-ethyl phosphonium bromide, the equipment includes pre-processing device 1, Pre-processing device 1 includes first reactor 2 and second reactor 3, and the pre-processing device is connected to reaction kettle 5.
Microwave reaction device 4 is equipped in the first reactor 2 of the present embodiment.
It is obvious to a person skilled in the art that invention is not limited to the details of the above exemplary embodiments, Er Qie In the case where without departing substantially from spirit or essential attributes of the invention, the present invention can be realized in other specific forms.Therefore, no matter From the point of view of which point, the present embodiments are to be considered as illustrative and not restrictive, and the scope of the present invention is by appended power Benefit requires rather than above description limits, it is intended that all by what is fallen within the meaning and scope of the equivalent elements of the claims Variation is included within the present invention.
In addition, it should be understood that although this specification is described in terms of embodiments, but not each embodiment is only wrapped Containing an independent technical solution, this description of the specification is merely for the sake of clarity, and those skilled in the art should It considers the specification as a whole, the technical solutions in the various embodiments may also be suitably combined, forms those skilled in the art The other embodiments being understood that.

Claims (7)

1. a kind of method for preparing tri-phenyl-ethyl phosphonium bromide, which comprises the following steps:
Step 1, pretreatment: it is to stand 45-55min, then carry out microwave treatment at 20-30 DEG C that bromoethane, which is placed in temperature,
Then again by triphenyl phosphonium at 30-40 DEG C, 25-35min is stood, it is spare;
Bromoethane, triphenyl phosphonium in step 1 is added to absolute ethanol according to weight ratio 2:1, is subsequently sent to by step 2 In reaction kettle (5), reaction temperature is 90-110 DEG C, reacts 20-30min, then adds bromobenzene, the reaction was continued 1-2h, with Temperature is risen to 160-170 DEG C afterwards, keeps the temperature 20-30min to get tri-phenyl-ethyl phosphonium bromide of the invention.
2. a kind of method for preparing tri-phenyl-ethyl phosphonium bromide according to claim 1, which is characterized in that at the microwave Manage bar part are as follows: microwave frequency 300-400MHz, power 700-780W, microwave treatment mode stop after being microwave treatment 35-45s 1-2min, then stop 45-55s after carrying out microwave treatment 20-30s, 2-3 times repeatedly.
3. a kind of method for preparing tri-phenyl-ethyl phosphonium bromide according to claim 2, which is characterized in that at the microwave Manage bar part are as follows: microwave frequency 350MHz, power 740W, microwave treatment mode stop 1.5min after being microwave treatment 40s, then into Stop 50s after row microwave treatment 25s, 3 times repeatedly.
4. a kind of method for preparing tri-phenyl-ethyl phosphonium bromide according to claim 1, which is characterized in that the step 2 Middle bromobenzene weight is the 10-20% of bromoethane, triphenyl phosphonium total weight.
5. a kind of method for preparing tri-phenyl-ethyl phosphonium bromide according to claim 4, which is characterized in that the step 2 Middle bromobenzene weight be bromoethane, triphenyl phosphonium total weight 15%.
6. a kind of equipment for being used to prepare tri-phenyl-ethyl phosphonium bromide, which is characterized in that the equipment includes pre-processing device (1), pre-processing device (1) includes first reactor (2) and second reactor (3), and the pre-processing device and reaction kettle (5) are even It is logical.
7. a kind of equipment for being used to prepare tri-phenyl-ethyl phosphonium bromide according to claim 6, which is characterized in that described Microwave reaction device (4) are equipped in one reactor (2).
CN201811292584.9A 2018-11-01 2018-11-01 A kind of method and apparatus preparing tri-phenyl-ethyl phosphonium bromide Pending CN109134539A (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103374033A (en) * 2012-04-24 2013-10-30 宁波大学 Functionalized quaternary phosphonium salt ionic liquid of organic phosphine and preparation method thereof
CN107903288A (en) * 2017-12-27 2018-04-13 安徽金善化工科技有限公司 A kind of ethyltriphenylphosphonium bromide
CN107903287A (en) * 2017-12-27 2018-04-13 安徽金善化工科技有限公司 A kind of preparation method of ethyltriphenylphosphonium bromide
CN107930565A (en) * 2017-12-27 2018-04-20 安徽金善化工科技有限公司 A kind of reaction kettle prepared for ethyltriphenylphosphonium bromide
CN108084226A (en) * 2017-12-27 2018-05-29 安徽金善化工科技有限公司 A kind of preparation method of butyltriphenylphosphonium bromide phosphine
CN108101940A (en) * 2017-12-27 2018-06-01 安徽金善化工科技有限公司 A kind of butyltriphenylphosphonium bromide phosphine

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103374033A (en) * 2012-04-24 2013-10-30 宁波大学 Functionalized quaternary phosphonium salt ionic liquid of organic phosphine and preparation method thereof
CN107903288A (en) * 2017-12-27 2018-04-13 安徽金善化工科技有限公司 A kind of ethyltriphenylphosphonium bromide
CN107903287A (en) * 2017-12-27 2018-04-13 安徽金善化工科技有限公司 A kind of preparation method of ethyltriphenylphosphonium bromide
CN107930565A (en) * 2017-12-27 2018-04-20 安徽金善化工科技有限公司 A kind of reaction kettle prepared for ethyltriphenylphosphonium bromide
CN108084226A (en) * 2017-12-27 2018-05-29 安徽金善化工科技有限公司 A kind of preparation method of butyltriphenylphosphonium bromide phosphine
CN108101940A (en) * 2017-12-27 2018-06-01 安徽金善化工科技有限公司 A kind of butyltriphenylphosphonium bromide phosphine

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ZHANG HU 等: "Unique Triphenylphosphonium Derivatives for Enhanced Mitochondrial Uptake and Photodynamic Therapy", 《BIOCONJUGATE CHEM.》 *
尹晓刚 等: "微波辅助法合成季鏻盐", 《日用化学工业》 *

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