CN109851470A - A method of the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- is prepared using micro passage reaction - Google Patents
A method of the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- is prepared using micro passage reaction Download PDFInfo
- Publication number
- CN109851470A CN109851470A CN201910206806.9A CN201910206806A CN109851470A CN 109851470 A CN109851470 A CN 109851470A CN 201910206806 A CN201910206806 A CN 201910206806A CN 109851470 A CN109851470 A CN 109851470A
- Authority
- CN
- China
- Prior art keywords
- hexafluoro
- micro passage
- butylene
- chloro
- reaction
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
2- chloro- 1,1,1 is prepared using micro passage reaction the invention discloses a kind of, the method of 4,4,4- hexafluoro -2- butylene, include the following steps: (1) activation of catalyst: liquid-phase fluorination catalyst and anhydrous HF being passed through micro passage reaction, the catalyst and HF mixture activated;(2) fluorination reaction: being back to step (1) micro passage reaction for activated catalyst made of step (1) and HF mixture, while anhydrous HF and hexachlorobutadiene entered micro passage reaction by the second road and third road respectively, will reflect mixture by pump and is delivered to rectifying column, overhead extraction 2- chloro- 1,1,1,4,4,4- hexafluoro -2- butylene and HF mixture are simultaneously layered, lower layer is 2- chloro- 1,1,1,4,4,4- hexafluoro -2- butylene, upper layer HF.The present invention prepares that the method high conversion rate of the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2-, selectivity is high, impurity is few, catalyst activity greatly prolongs.Using the silicon carbide microchannel reactor reaction time is short, super strong acid resistant burn into reaction mass transfer excellent heat transfer properties can make catalyst keep prolonged high activity.
Description
Technical field
The invention belongs to organic synthesis fields, and in particular to a kind of use micro passage reaction preparation 2- chloro- 1,1, Isosorbide-5-Nitrae,
The method of 4,4- hexafluoro -2- butylene.
Background technique
The present invention relates to be that basic raw material prepares forth generation foaming agent 1,1,1,4,4,4- hexafluoro -2- fourth with hexachlorobutadiene
First step reaction hexachlorobutadiene liquid-phase fluorination on alkene (HFO-1336mzz) prepares the chloro- 1,1,1,4,4,4- hexafluoro -2- fourth of 2-
The process of alkene is improved.
1,1, Isosorbide-5-Nitrae, 4,4- hexafluoro -2- butylene, ODP 0, GWP 5 is non-combustible, and thermal coefficient is close to HFC-365mfc
And HFC-245fa.1,1, Isosorbide-5-Nitrae, 4,4- hexafluoro -2- butylene have along anti-two kinds of isomers, wherein cis- hexafluoro -2- butylene (Z-type)
Boiling point is 33~34 DEG C, is mainly used for substitution HCFC-141b and uses as foaming agent.Trans- hexafluoro -2- butylene (E type) boiling point is
6~8 DEG C, it is mainly used for using with other ODS substitute mixtures as refrigerant, foaming agent and extinguishing chemical.
But liquid-phase fluorination uses and generates corrosive compound, such as hydrogen fluoride, hydrogen chloride and lewis acid catalyst
Super acid can be formed.These super acids tend to corrode the reactor vessel wherein being reacted, even by resistant material example
Such as reactor of Inconel600, HastelloyC composition.The corrosion-damaged structural intergrity of reactor of reactor, subtracts
Its few service life.Therefore, it is necessary to reduce reactor corrosion to the greatest extent.In liquid phase reactor, especially when reactive component is unmixing
Or when partial miscibility, the mixability of reaction mass influences conversion ratio, yield and selectivity.Effective for reaction system mixes
It closes, leads to conventional whisk, but in corrosive environment, even if the reactor being usually coated through fluoropolymer is equally limited by corrosion and leads
The bulge of the poly- material of interior Fluorine-lined such as of losing of the structural intergrity of reactor and blender is caused to fall off, the corrosion of machinery sealing material
Damage etc., these have the danger etc. for causing corrosivity or the leakage of poisonous and harmful material.As patent CN104072333A discloses one
Kind liquid-phase fluorination preparation 2- chloro- 1,1, Isosorbide-5-Nitrae, the method for 4,4- hexafluoro -2- butylene, this method are stirred to react using autoclave
Device, it is clear that there are equipment etching problems, and react and need 3~12h, and reaction efficiency is relatively low.
Therefore, to avoid the possible material of stirred reactor disclosure risk out of control, current domestic production liquid phase fluorine
Change reaction and mainly or using safer anhydrous HF recycles bubbling style reactor.Obvious this reactor is some strongly exothermic
Liquid phase fluorination reaction in that there are mass-and heat-transfers is poor, cause material polymer there are hot localised points in reaction mass and generate packet
Wrap up in catalyst and fluorination catalyst such as SbClxF5-xThermal decomposition is so that Sb5+It makes a price reduction to inactive Sb3+, so as to cause catalyst
Stability is poor.
Microchannel flow reactor is the pipeline reactor continuously flowed, and the type reactor has micron order size
Reaction channel.Compared to traditional chemical industry equipment, micro passage reaction inner passage size is small, and distance is extremely short between thin layer of fluid, leads to
Jie for crossing fluid micellar sees viscous yielding and molecule spreads the quick microcosmic mixing that can be achieved between reaction mass;Micro passage reaction
With great specific surface area, between fluid and wall, there is sufficient contact area between fluid and fluid, so make heat exchange, reaction
Efficiency significantly improves.And the micro passage reaction of silicon carbide material is used to can be very good to accomplish resistance to anhydrous hydrofluoric acid and hydrofluoric acid
The corrosion of the super acid formed with liquid-phase fluorination catalyst.
Summary of the invention
Hexachlorobutadiene preparation by liquid-phase fluorization is carried out using silicon carbide microchannel reactor it is an object of that present invention to provide a kind of
Standby 2- chloro- 1,1, Isosorbide-5-Nitrae, the method for 4,4- hexafluoro -2- butylene make liquid phase fluorination reaction more efficient, resistance to using the reactor
Material corrosion, catalyst keep high activity and stability.
In order to solve the above-mentioned technical problem, the present invention adopts the following technical scheme:
It is a kind of that 2- chloro- 1,1, Isosorbide-5-Nitrae, the method for 4,4- hexafluoro -2- butylene are prepared using micro passage reaction, it is characterised in that
Include the following steps:
(1) activation of catalyst: liquid-phase fluorination catalyst and anhydrous HF are passed through micro passage reaction, the catalysis activated
Agent and HF mixture;
(2) activated catalyst made of step (1) and HF mixture fluorination reaction: are back to step (1) microchannel plate
Device is answered, while anhydrous HF and hexachlorobutadiene are entered into micro passage reaction by the second road and third road respectively, will be reflected
Mixture rectifying column is delivered to by pump, overhead extraction 2- chloro- 1,1, Isosorbide-5-Nitrae, 4,4- hexafluoro -2- butylene and HF mixture and point
Layer, lower layer are 2- chloro- 1,1, Isosorbide-5-Nitrae, 4,4- hexafluoro -2- butylene, upper layer HF.
Preferably, a top is connected between micro passage reaction and rectifying column equipped with the condensation for filling Kazakhstan C alloy filler
The gas-liquid separation storage tank of device.In reaction (1) step, gas-liquid separation storage tank is used to release HCl gas, to obtain completing activation
Catalyst and HF mixture.Liquid portion is delivered in rectifying column in reaction (2) step, gas-liquid separation storage tank.
Preferably, the top of the distillation column obtains in step (2) HF returns to micro passage reaction, catalyst that tower bottom obtains,
It is continuous that the mixture of the complete hexachlorobutadiene of unreacted, midbody product and a small amount of HF is recycled back to micro passage reaction
It applies.The complete feedstock circulation of reaction intermediate and unreacted is increased to the conversion ratio of reaction to micro passage reaction.
Preferably, liquid-phase fluorination catalyst is one of Antimony pentachloride, titanium tetrachloride, tin tetrachloride or a variety of.
Preferably, micro passage reaction is to be composed in series by multiple silicon carbide modular units.Silicon carbide material is resistance to anhydrous non-
The corrosion for the super acids that hydrofluoric acid and hydrofluoric acid and liquid-phase fluorination catalyst are formed.
Preferably, the quantity of concatenated silicon carbide modular unit is 6, and mixed material is in each silicon carbide modular unit
The reaction time is stopped no more than 0.4 minute, mixed material stops the reaction time preferably 0.08 in each silicon carbide modular unit
~0.4 minute, with guarantee mixed material each silicon carbide modular unit quickly through.
Preferably, 100 DEG C~150 DEG C of activation temperature in step (1), 1~1.5Mpa of reaction pressure.
Preferably, reaction mixture fluid flow 20ml/min~100ml/min in step (2), reaction mass mole are matched
Than for HF: hexachlorobutadiene: catalyst=10 of activation~30:1~2:1.
Preferably, 100 DEG C~150 DEG C of reaction temperature in step (2), 1~1.5Mpa of reaction pressure.
Preferably, chlorine was individually passed through micro passage reaction every 2 hours and carries out activating and regenerating to catalyst in step (2)
10 minutes, chlorine gas flow 0.005ml/min.Chlorine is passed through so that part Sb5+The Sb that price reduction inactivation generates3+It reverts to
Sb5+。
Due to the adoption of the above technical scheme, the invention has the following advantages:
Compared with traditional bubbling column reactor, the reaction of liquid phase fluorination reaction is carried out using silicon carbide microchannel reactor
Time is short, resistance to HF or liquid-phase catalyst combine the super acids burn into reaction mass transfer excellent heat transfer properties to be formed with HF and can make to be catalyzed
Agent keeps prolonged high activity.The present invention prepares the method high conversion rate of the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2-, choosing
Selecting property is high, impurity is few, catalyst activity greatly prolongs.
Specific embodiment
Below by embodiment, the invention will be further described.
Embodiment 1
Activation of catalyst:
By SbCl5(molar ratio 1:10) is passed through with 20ml/min to the concatenated silicon carbide mould of 6 8ml after anhydrous HF mixing
The micro passage reaction that block is combined into is activated, and 100 DEG C of activation temperature, pressure 1MPa, the residence time 2.4 minutes, material went out
Enter the gas-liquid separation storage tank that the condenser of C alloy filler is breathed out on a top equipped with filling after coming, releases HCl gas, collect
To the catalyst and HF mixture for completing activation.
Fluorination reaction:
Step 1 is completed into a part of liquid catalyst of activation and anhydrous HF mixture is returned again to micro passage reaction,
Meanwhile anhydrous HF enters the 1st reactor module by the 2nd road and the 3rd tunnel respectively with hexachlorobutadiene and mixes with catalyst, passes through
Reactor mixture fluid flow 20ml/min, material mol ratio are HF: hexachlorobutadiene: SbClxF5-x=10:1:1, instead
Answer 100 DEG C of temperature, pressure 1MPa, reaction time 2.4 minutes.The material that reactor comes out breathes out C equipped with filling by one
The gas-liquid separation storage tank of the condenser of alloy packing releases HCl gas, then is delivered to rectifying column, overhead extraction product by pump
2- chloro- 1,1, Isosorbide-5-Nitrae, 4,4- hexafluoro -2- butylene and HF mixture are simultaneously layered, and the HF of inorganic layer returns to micro passage reaction, tower bottom
The mixture of the complete hexachlorobutadiene of catalyst, unreacted, midbody product and a small amount of HF is recycled back to reactor company
It is continuous to apply.Chlorine was individually passed through reactor and carries out activating and regenerating 10 minutes to catalyst every 2 hours, chlorine gas flow
0.005ml/min.Sample chromatography, hexachlorobutadiene conversion ratio 94%, 2- chloro- 1,1, Isosorbide-5-Nitrae, the choosing of 4,4- hexafluoro -2- butylene
Selecting property 96% is reacted after continuing 500h, and catalyst activity loses decline.
Embodiment 2
Activation of catalyst:
By SbCl5(molar ratio 1:20) is passed through with 100ml/min to 6 concatenated silicon carbide of 8ml after anhydrous HF mixing
Block combiner at micro passage reaction activated, 150 DEG C of activation temperature, pressure 1.5MPa, the residence time 0.48 minute, object
Material enters the gas-liquid separation storage tank that the condenser of C alloy filler is breathed out on a top equipped with filling after coming out, release HCl gas, receives
Collection obtains completing the catalyst and HF mixture of activation.
Fluorination reaction:
Step 1 is completed into a part of liquid catalyst of activation and anhydrous HF mixture is returned again to micro passage reaction,
Meanwhile anhydrous HF enters the 1st reactor module by the 2nd road and the 3rd tunnel respectively with hexachlorobutadiene and mixes with catalyst, passes through
Reactor mixture fluid flow 100ml/min, material mol ratio are HF: hexachlorobutadiene: SbClxF5-x=30:2:1, instead
Answer 150 DEG C of temperature, pressure 1.5MPa, reaction time 0.48 minute.The material that reactor comes out is by one equipped with condensation
The gas-liquid separation storage tank of device releases HCl gas, then is delivered to rectifying column by pumping, overhead extraction product 2- chloro- 1,1, Isosorbide-5-Nitrae, and 4,
4- hexafluoro -2- butylene and HF mixture are simultaneously layered, and inorganic layer HF returns to micro passage reaction, and tower bottom catalyst, unreacted are complete
The mixture of hexachlorobutadiene, midbody product and a small amount of HF is recycled back to reactor and continuously applies.Chlorine is small every 2
When, it is individually passed through reactor and catalyst is carried out activating and regenerating 10 minutes, chlorine gas flow 0.005ml/min.Sample chromatography
Analysis, hexachlorobutadiene conversion ratio 96%, 2- chloro- 1,1, Isosorbide-5-Nitrae, 4,4- hexafluoro -2- butylene selectivity 96% react and continue 500h
Afterwards, catalyst activity loses decline.
Embodiment 3
Activation of catalyst:
By TiCl4(molar ratio 1:15) is passed through with 50ml/min to the concatenated silicon carbide mould of 6 8ml after anhydrous HF mixing
The micro passage reaction that block is combined into is activated, and 120 DEG C of activation temperature, pressure 1.2MPa, the residence time 0.96 minute, material
Enter the gas-liquid separation storage tank that the condenser of C alloy filler is breathed out on a top equipped with filling after out, releases HCl gas, collect
Obtain completing the catalyst and HF mixture of activation.
Fluorination reaction:
Step 1 is completed into a part of liquid catalyst of activation and anhydrous HF mixture is returned again to micro passage reaction,
Meanwhile anhydrous HF enters the 1st reactor module by the 2nd road and the 3rd tunnel respectively with hexachlorobutadiene and mixes with catalyst, passes through
Reactor mixture fluid flow 50ml/min, material mol ratio are HF: hexachlorobutadiene: TiClxF4-x=15:1:1, instead
Answer 120 DEG C of temperature, pressure 1.2MPa, reaction time 0.96 minute.The material that reactor comes out is equipped with by a top
The gas-liquid separation storage tank of the condenser of C alloy filler is breathed out in filling, releases HCl gas, then be delivered to rectifying column by pump, tower top is adopted
Chloro- 1 product 2- out, 1, Isosorbide-5-Nitrae, 4,4- hexafluoro -2- butylene and HF mixture are simultaneously layered, and inorganic layer HF returns to micro passage reaction,
The mixture of the complete hexachlorobutadiene of tower bottom catalyst, unreacted, midbody product and a small amount of HF is recycled back to reactor
Continuously apply.Chlorine was individually passed through reactor and carries out activating and regenerating 10 minutes to catalyst every 2 hours, chlorine gas flow
0.005ml/min.Sample chromatography, hexachlorobutadiene conversion ratio 93%, 2- chloro- 1,1, Isosorbide-5-Nitrae, the choosing of 4,4- hexafluoro -2- butylene
Selecting property 96% is reacted after continuing 300h, and catalyst activity loses decline.
Embodiment 4
It is SnCl by the catalyst change in embodiment 34, remaining method is the same as embodiment 3, acquired results hexachlorobutadiene turn
Rate 90%, 2- chloro- 1,1, Isosorbide-5-Nitrae, 4,4- hexafluoro -2- butylene selectivity 97% are reacted after continuing 300h, catalyst activity loses
Decline.
Comparative example 1
In 2.5L bubble tower type reaction kettle (draw ratio 8:1, top is with the blowdown condenser for breathing out C alloy filler) respectively
299g (1mol) SbCl is added5, 400g (20mol) HF, HF from reaction tower bottom by distributor bubbling, be warming up to 90 degree of work
Change, centre persistently releases HCl, maintains reaction pressure 1MPa, and 1h post activation is completed.Then chlordene dibutene is continuously passed through with HF
Reaction kettle, molar ratio of material HF: hexachlorobutadiene: SbClxF5-x=30:2:1,90 DEG C of reaction temperature, pressure 1MPa, reaction
Residence time 4h, while reaction product material is delivered to rectifying column from bottom portion with pump, overhead extraction product 2- chloro- 1,1, Isosorbide-5-Nitrae,
4,4- hexafluoro -2- butylene and HF mixture are simultaneously layered, and inorganic layer HF returns to bubble tower type reaction kettle, rectifying column bottom catalyst, not
The mixture of reacted hexachlorobutadiene, midbody product and a small amount of HF is recycled back to reaction kettle and continuously applies.Chlorine
Every 2 hours, individually it is passed through reactor and catalyst is carried out activating and regenerating 10 minutes, chlorine gas flow 0.005ml/min.It takes
Sample chromatography, hexachlorobutadiene conversion ratio 88%, 2- chloro- 1,1, Isosorbide-5-Nitrae, 4,4- hexafluoro -2- butylene selectivity 92%, reaction is held
After continuous 240h, hexachlorobutadiene conversion ratio 67%, 2- chloro- 1,1, Isosorbide-5-Nitrae, 4,4- hexafluoro -2- butylene selectivity 81%, material color
Jaundice retrogradation, there is high-boiling components generation.
The above is only specific embodiments of the present invention, but technical characteristic of the invention is not limited thereto.It is any with this hair
Based on bright, to solve essentially identical technical problem, essentially identical technical effect is realized, made ground simple change, etc.
With replacement or modification etc., all it is covered by among protection scope of the present invention.
Claims (10)
1. a kind of prepare 2- chloro- 1,1, Isosorbide-5-Nitrae, the method for 4,4- hexafluoro -2- butylene using micro passage reaction, it is characterised in that packet
Include following steps:
(1) activation of catalyst: being passed through micro passage reaction for liquid-phase fluorination catalyst and anhydrous HF, the catalyst activated and
HF mixture;
(2) activated catalyst made of step (1) and HF mixture fluorination reaction: are back to step (1) described microchannel plate
Device is answered, while anhydrous HF and hexachlorobutadiene are entered into the micro passage reaction by the second road and third road respectively, will be reacted
Mixture out is delivered to rectifying column, overhead extraction 2- chloro- 1,1, Isosorbide-5-Nitrae, 4,4- hexafluoro -2- butylene and HF mixture by pump
And be layered, lower layer is 2- chloro- 1,1, Isosorbide-5-Nitrae, 4,4- hexafluoro -2- butylene, upper layer HF.
2. a kind of according to claim 1 prepare the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- using micro passage reaction
Method, it is characterised in that: breathe out C alloy equipped with filling and fill out in top of connecting between the micro passage reaction and the rectifying column
The gas-liquid separation storage tank of the condenser of material.
3. a kind of according to claim 1 prepare the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- using micro passage reaction
Method, it is characterised in that: the HF that the top of the distillation column obtains in the step (2) returns to micro passage reaction, and what tower bottom obtained urges
The mixture of the complete hexachlorobutadiene of agent, unreacted, midbody product and a small amount of HF is recycled back to microchannel plate and answers
Device is continuously applied.
4. a kind of according to claim 1 prepare the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- using micro passage reaction
Method, it is characterised in that: the liquid-phase fluorination catalyst is one of Antimony pentachloride, titanium tetrachloride, tin tetrachloride or a variety of.
5. a kind of according to claim 1 prepare the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- using micro passage reaction
Method, it is characterised in that: the micro passage reaction is to be composed in series by multiple silicon carbide modular units.
6. a kind of according to claim 5 prepare the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- using micro passage reaction
Method, it is characterised in that: the quantity of the concatenated silicon carbide modular unit is 6, and mixed material is in each silicon carbide module
The reaction time is stopped in unit no more than 0.4 minute.
7. a kind of according to claim 1 prepare the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- using micro passage reaction
Method, it is characterised in that: 100 DEG C~150 DEG C of activation temperature, 1~1.5Mpa of reaction pressure in the step (1).
8. a kind of according to claim 1 prepare the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- using micro passage reaction
Method, it is characterised in that: reaction mixture fluid flow 20ml/min~100ml/min in the step (2), reaction mass rub
Your proportion is HF: hexachlorobutadiene: catalyst=10 of activation~30:1~2:1.
9. a kind of according to claim 8 prepare the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- using micro passage reaction
Method, it is characterised in that: 100 DEG C~150 DEG C of reaction temperature, 1~1.5Mpa of reaction pressure in the step (2).
10. a kind of according to claim 1 prepare the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- using micro passage reaction
Method, it is characterised in that: in the step (2) chlorine every 2 hours individually be passed through micro passage reaction to catalyst carry out
Activating and regenerating 10 minutes, chlorine gas flow 0.005ml/min.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910206806.9A CN109851470A (en) | 2019-03-19 | 2019-03-19 | A method of the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- is prepared using micro passage reaction |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910206806.9A CN109851470A (en) | 2019-03-19 | 2019-03-19 | A method of the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- is prepared using micro passage reaction |
Publications (1)
Publication Number | Publication Date |
---|---|
CN109851470A true CN109851470A (en) | 2019-06-07 |
Family
ID=66901200
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910206806.9A Pending CN109851470A (en) | 2019-03-19 | 2019-03-19 | A method of the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- is prepared using micro passage reaction |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109851470A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110283042A (en) * | 2019-07-26 | 2019-09-27 | 西安近代化学研究所 | A method of the synthesis chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- |
CN111013614A (en) * | 2019-11-06 | 2020-04-17 | 浙江师范大学 | Catalyst carrier and catalyst for preparing chlorine by oxidizing hydrogen chloride, and preparation method and application thereof |
CN113880978A (en) * | 2021-08-31 | 2022-01-04 | 泰兴梅兰新材料有限公司 | Method and device for preparing microchannel of fluoropolyether carboxylic acid for fluorinated ethylene propylene |
CN114031492A (en) * | 2021-12-13 | 2022-02-11 | 上海簇睿低碳能源技术有限公司 | Process system for synthesizing acetic acid or acetic anhydride by using microchannel reactor and preparation method |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107983277A (en) * | 2017-12-29 | 2018-05-04 | 山东金德新材料有限公司 | Silicon carbide reactor pipe and the micro passage reaction being made of the reaction tube |
US20190031582A1 (en) * | 2017-07-27 | 2019-01-31 | The Chemours Company Fc, Llc | Process for Preparing (Z)-1,1,1,4,4,4-Hexafluoro-2-Butene |
-
2019
- 2019-03-19 CN CN201910206806.9A patent/CN109851470A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20190031582A1 (en) * | 2017-07-27 | 2019-01-31 | The Chemours Company Fc, Llc | Process for Preparing (Z)-1,1,1,4,4,4-Hexafluoro-2-Butene |
CN107983277A (en) * | 2017-12-29 | 2018-05-04 | 山东金德新材料有限公司 | Silicon carbide reactor pipe and the micro passage reaction being made of the reaction tube |
Non-Patent Citations (2)
Title |
---|
M.霍特列斯基: "《有机氟化合物的化学》", 30 April 1965, 上海科学技术出版社 * |
徐克: "《精细有机化工原料及中间体手册》", 30 June 1998, 化学工业出版社 * |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110283042A (en) * | 2019-07-26 | 2019-09-27 | 西安近代化学研究所 | A method of the synthesis chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- |
CN110283042B (en) * | 2019-07-26 | 2022-05-24 | 西安近代化学研究所 | Method for synthesizing 2-chloro-1, 1,1,4,4, 4-hexafluoro-2-butene |
CN111013614A (en) * | 2019-11-06 | 2020-04-17 | 浙江师范大学 | Catalyst carrier and catalyst for preparing chlorine by oxidizing hydrogen chloride, and preparation method and application thereof |
CN111013614B (en) * | 2019-11-06 | 2023-01-13 | 浙江师范大学 | Catalyst carrier and catalyst for preparing chlorine by oxidizing hydrogen chloride, and preparation method and application thereof |
CN113880978A (en) * | 2021-08-31 | 2022-01-04 | 泰兴梅兰新材料有限公司 | Method and device for preparing microchannel of fluoropolyether carboxylic acid for fluorinated ethylene propylene |
CN114031492A (en) * | 2021-12-13 | 2022-02-11 | 上海簇睿低碳能源技术有限公司 | Process system for synthesizing acetic acid or acetic anhydride by using microchannel reactor and preparation method |
CN114031492B (en) * | 2021-12-13 | 2023-08-29 | 上海簇睿低碳能源技术有限公司 | Process system for synthesizing acetic acid or acetic anhydride by adopting microchannel reactor and preparation method |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN109851470A (en) | A method of the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- is prepared using micro passage reaction | |
CN103274895B (en) | The preparation method of fluorinated organic compounds | |
CN103172488B (en) | Prepare the method for fluorinated organic compounds | |
CN1852880B (en) | Process for the manufacture of 1,3,3,3- tetrafluoropropene | |
US9061957B2 (en) | Method for producing fluorinated organic compounds | |
CN101835729A (en) | Method for producing fluorinated olefins | |
JP2019196312A (en) | Manufacturing method of 1,2-difluoroethylene and/or 1,1,2-trifluoroethane | |
CN101351426B (en) | Method for producing fluorinated organic compounds | |
CN101687731A (en) | Process for the manufacture of hydrofluoroolefins | |
EP2348007A1 (en) | Method for producing fluorinated organic compounds | |
WO2016090744A1 (en) | Process for the joint preparation of 1, 3, 3, 3-tetrafluoropropene and 2, 3, 3, 3-tetrafluoropropene | |
US8987534B2 (en) | Process for the manufacture of hydrochlorofluoroolefins | |
CN104710274A (en) | Process for co-producing 1,3,3,3-tetrafluoropropene and/or 2,3,3,3-tetrafluoropropene | |
CN106946647B (en) | A kind of method that the isomerization of mixture room temperature prepares trans-1,3,3,3-tetrafluoropropene | |
CN101913983B (en) | Preparation method of 1,1,1,3,3-pentafluoropropane | |
CN103508842B (en) | The preparation method of chloro-3,3, the 3-trifluoro propenes of 1,2-bis- | |
CN102211974A (en) | Preparation method of 1,3,3,3-tetrafluoropropylene | |
CN110283043A (en) | A method of preparing the chloro- 1,1,1,4,4,4- hexafluoro -2- butylene of 2- | |
CN104140353A (en) | Method for preparing 1,1,1-halothane through liquid phase one-step fluorination of vinylidene chloride | |
Manzer et al. | The key role of catalysis in the phase-out of chlorofluorocarbons (CFCs) | |
CN112537997B (en) | Method and device for co-production of 3,3, 3-trifluoropropene and 2-chloro-3, 3, 3-trifluoropropene | |
CN103524293B (en) | Method for preparing 2,3-dichlone-1,1,1,2-tetrachlorofluoropropane | |
CN108610233B (en) | Preparation method of 3, 3, 3-trifluoropropene | |
JP6197637B2 (en) | (E) Method for producing 1,3,3,3-tetrafluoropropene | |
CN100582068C (en) | Method of producing hydrofluorocarbons |
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: 20190607 |