CN107759442A - A kind of synthetic method of medium chain perfluoroalkyl iodide telomer - Google Patents
A kind of synthetic method of medium chain perfluoroalkyl iodide telomer Download PDFInfo
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- CN107759442A CN107759442A CN201610693413.1A CN201610693413A CN107759442A CN 107759442 A CN107759442 A CN 107759442A CN 201610693413 A CN201610693413 A CN 201610693413A CN 107759442 A CN107759442 A CN 107759442A
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- medium chain
- synthetic method
- perfluor
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
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Abstract
The invention belongs to technical field of organic synthesis, and in particular to a kind of synthetic method of medium chain perfluoroalkyl iodide telomer.It comprises the following steps：Polymerized monomer CF is added into reaction vessel2=CR1R2, telogen RfI, metallic catalyst and co-catalyst carry out polymerisation and obtain the perfluoroalkyl iodide telomer that carbon number is 3~14, and it has below formula：Rf(CF2CR1R2)nI, wherein, RfFor C1‑8Perfluoroalkyl；R1、R2It may be the same or different, each be selected from fluorine atom, C1‑4Saturation perfluoroalkyl；The integers of n=1 6；The co-catalyst is PR1R2R3, R1、R2、R3It may be the same or different, selected from alkyl and aryl.This method is suitable for industrialization large-scale production, can effectively produce medium chain full-fluorine alkyl iodide at low temperature, produces seldom impurity, and target compound narrow molecular weight distribution, yield are high.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of synthesis of medium chain perfluoroalkyl iodide telomer
Method.
Background technology
It is well known that full-fluorine alkyl iodide is the alkylating conjunction of single iodo perfluoro that hydrogen atom is substituted completely by fluorine atom
Thing, typically it is made up of a series of perfluoroalkyl of different chain lengths, the mainly carbon number with application value is the complete of 6-12
The perfluor iodo-octane performance that halothane test, wherein carbon number are 8 is optimal.Perfluoroalkyl iodides are production fluorine finishing agent, fluorine-containing table
The key intermediate of face activating agent and other fluoride-containing PMMAs, downstream product light-water extinguishing chemical, magnetic pipe recording material,
Water and oil repellant fabric finishing agent, paper finishing agent, oilfield chemistry, photosensitive material, high-grade releasing agent, metallic anti-rust paint, plastics rubber
Glue auxiliary agent and medical material etc. have important purposes.
Be telogen with PFEI, seven fluorine isopropyl iodides, tetrafluoroethene or hexafluoropropene be polymerized monomer light,
It is known that heat, free radical or catalysis, which trigger lower progress telomerisation,.
United States Patent (USP) US5650545 describes a kind of thermal initiation that carried out in 344 DEG C of tubular reactor and prepares perfluor alkane
The method of base iodine.This method is passed through by tetrafluoroethene in the port of reactor and from reactor head for the intake of 2/3 pipe range,
High carbon number product can be reduced, but the shortcomings that thermal initiation be at high temperature the easy initial ring consor of tetrafluoroethene into octafluorocyclobutane,
Accumulation causes tetrafluoroethene conversion ratio low in the reactor, and accessory substance is more under high temperature, and the selectivity of target product declines, molecule
Amount distribution is wide.
EP1380557 describes one kind in tubular reactor, with copper powder, copper and tin composite powder, sintered copper powder and copper powder
The technique for triggering perfluoroalkyl iodide telomerization with the mixed catalyst of glass putty.Although this method can improve to obtain the relative of telomer
Molecular vibrational temperature, and the content of product is low, but the yield of this method also leaves some room for improvement.
US3226449 describes a kind of with the initiations such as alkyl peroxide, propylene peroxide, acetone peroxide preparation
The telomerization method of perfluoroalkyl iodides, this method need to react at high temperature under high pressure, and system is explosive, introduces hydrocarbon group, by-product
Thing is more and molecular weight distribution is wide.
CN1379008A describes a kind of method that light-initiated telomerization prepares alkyl iodide, and this method is by C2F5I and tetrafluoro
The mixture of ethene, add the reactor using low-voltage light source as initiation source and carry out telomerisation, although this method is with relatively low
Pressure and higher reaction rate, but light source is easily covered by polymer, can not be further continued for carrying out initiation reaction and causing
Production capacity is small, can not realize large-scale industrial production.
Therefore, it is necessary to develop a kind of suitable industrialization large-scale production, without the complete of HTHP or light-initiated equipment
The production method of fluoroalkyl iodide, to be made with the perfluoroalkyl iodate that purity is high, narrow molecular weight distribution and yield are high
Thing.
The content of the invention
In view of the shortcomings of the prior art, the main object of the present invention is to provide one kind and by telomerisation synthesizes medium chain
The method of perfluoroalkyl iodide telomer, it is suitable for industrialization large-scale production, can effectively produces medium chain at low temperature
Full-fluorine alkyl iodide, seldom impurity is produced, and target compound narrow molecular weight distribution, yield are high.
A kind of synthetic method of medium chain perfluoroalkyl iodide telomer, comprises the following steps：
Polymerized monomer CF is added into reaction vessel2=CR1R2, telogen RfI, metallic catalyst and co-catalyst are carried out
Polymerisation obtains the perfluoroalkyl iodide telomer that carbon number is 3~14, and it has below formula：Rf(CF2CR1R2)nI, wherein,
RfFor C1-8Perfluoroalkyl；R1、R2It may be the same or different, each be selected from fluorine atom, C1-4Saturation perfluoroalkyl；N=1-6 integers；Institute
It is PR to state co-catalyst1R2R3, R1、R2、R3It may be the same or different, selected from alkyl and aryl.
The C1-4The not limiting example of saturation perfluoroalkyl has perfluoro-methyl, perfluoro-ethyl, perfluor n-propyl, perfluor
Isopropyl, perfluoro-n-butyl group, perfluor isobutyl group and perfluoro-t-butyl.Preferably perfluoro-methyl and perfluoro-ethyl.
It is adapted to the polymerized monomer CF of the inventive method2=CR1R2Not limiting example have, such as tetrafluoroethene, hexafluoro third
Alkene, 2- trifluoromethyls perfluoropropene, α-perfluor hexene, 2- trifluoromethyl-alphas-perfluorobuttene etc..Preferably tetrafluoroethene or hexafluoro
Propylene.
RfPreferably C1-6Perfluoroalkyl, more preferably C1-4Perfluoroalkyl.It is suitable for the R of the inventive methodfGroup it is non-limiting
Property example have, it is such as perfluoro-methyl, perfluoro-ethyl, perfluor n-propyl, perfluoroisopropyl, perfluoro-n-butyl group, perfluor isobutyl group, complete
The fluorine tert-butyl group, perfluor n-pentyl, perfluor isopentyl, perfluor n-hexyl and perfluor dissident's base etc..It is preferably perfluoro-ethyl, perfluor
N-propyl, perfluoro-n-butyl group, perfluor n-hexyl.
In an example of the present invention, medium chain perfluoroalkyl iodide telomer is selected from Rf(CF2CF(CF3))nI and Rf
(CF2C(CF3)(CF3))nI, wherein RfIt is C1-8Perfluoroalkyl, preferably C1-6Perfluoroalkyl, more preferably C1-4Perfluoroalkyl, n are
1-6 integers；Preferably 1-4 integers.
In another example of the present invention, medium chain perfluoroalkyl iodide telomer is selected from CF3(CF2CF2)nI、CF3CF2
(CF2CF2)nI、CF3(CF2CF(CF3))nI、CF3CF2(CF2CF(CF3))nI、CF3CF2(CF2C(CF3)(CF3))nI、CF3(CF2C
(CF3)(CF3))nI, wherein n are 1-6 integers；Preferably 1-4 integers.
The ratio of telogen and polymerized monomer depends on specifically applicable telogen and polymerized monomer, reaction time etc..Institute
The mol ratio for stating polymerized monomer and telogen is 1：99-15：85, preferably 5：95-10：90.
Being adapted to the species of the metallic catalyst of the inventive method does not have special limitation, as long as it can actually be exchanged
Poly- reaction has catalytic action.The non-limiting examples of the catalyst have, for example, metallic copper, tin, zinc, vanadium, rhenium, rhodium, ruthenium,
Platinum, silver, two or more alloys formed in them, the alloy can contain that a small amount of (such as content accounts for 10 weight %, preferably
Account for more than 5 weight %) itself there is no the metal such as iron, nickel, chromium, molybdenum, tungsten, titanium of catalytic activity.
In an example of the present invention, lived using copper, tin as catalyst with improving the catalysis of medium chain polymer
Property and selectivity.
It is increase catalyst reaction area so as to improve its catalytic efficiency, the above-mentioned metal powder preferably produced using electrolysis
End is used as catalyst.The average grain diameter of the metal dust is 1~200 μm, is preferably 10~100 μm, more preferably 30~80 μ
m。
Catalyst amount is without particular limitation, as long as can effectively play catalytic action and polymerisation is had no adverse effect
.In an example of the present invention, the dosage of the catalyst is 0.5~10%, preferably the 1~5% of telogen quality.
The co-catalyst can provide coordination and have certain space steric hindrance, preferably triphenylphosphine and tributyl
Phosphine；Co-catalyst can improve the conversion ratio of reaction to the coordination of reaction intermediate, and adjust its space for substituting group
Steric hindrance can efficiently control the distribution of reaction product chain length.
Based on the metallic catalyst, the dosage of co-catalyst is 10-50 weight %, preferably 15-30 weight %, more preferably
For 20-28 weight %.
Polymeric reaction temperature can be suitable for any ordinary temperature of polymerisation in the inventive method, as long as polymerization is single
Obvious side reaction does not occur for body.For example, when monomer is tetrafluoroethene, the polymeric reaction temperature should not make tetrafluoroethene
Substantially aggregate into octafluorocyclobutane.In an example of the present invention, the polymeric reaction temperature is 60-150 DEG C, and temperature is preferred
For 90-110 DEG C.
Polymerization pressure can be suitable for any normal pressures of polymerisation in the inventive method, as long as the reaction
Pressure will not cause polymerization reaction monomer that obvious side reaction occurs.In an example of the present invention, the polymerization is anti-
The pressure answered is 0.5-5MPa, preferably 1-3MPa.
The beneficial effects of the invention are as follows：The conversion ratio that described co-catalyst is effectively improved reaction is introduced in the reaction
With the selectivity to medium chain product, this is due to that co-catalyst can improve reaction to the coordination of reaction intermediate
Conversion ratio, and the steric hindrance for adjusting its substituted radical can efficiently control the distribution of reaction product chain length.
Embodiment
The present invention is described in more detail with reference to embodiment.
Embodiment 1
600mL stainless steel vertical response kettles, electrolytic copper powder 8g, triphenyl phosphorus 2g are added after drying water removal.After kettle is evacuated
Deoxygenation is replaced with drying nitrogen again, oxygen content reaches below 10ppm.Used additives pump adds C into kettle at room temperature2F5I 780g,
Stirring is opened, tetrafluoroethene is passed through, is warming up to and starts to react, pressure is about 2MPa when being increased to 110 DEG C, is treated in kettle under pressure
When being down to 1.8MPa, it is 2MPa to be passed through tetrafluoroethene to pressure again, is repeated several times, reacts to pressure and no longer change, and is cooled, and is returned
Receive unreacted C2F5I, obtain product C2F5(CF2CF2)nThe common 190g of I.Product passes through alkali cleaning, is joined after dewater treatment using makings
1 is shown in Table with each component and its ratio in analysis product.
The analysis result of table 1
| Chain length (n) | Ratio (%) |
| 2 | 37 |
| 3 | 30 |
| Other | 33 |
Other parts are mainly tetrafluoroethene oligomer.
Comparative example 1
600mL stainless steel vertical response kettles, electrolytic copper powder 8g is added after drying water removal.Drying nitrogen is used after kettle is evacuated again
Deoxygenation is replaced, oxygen content reaches below 10ppm.Used additives pump adds C into kettle at room temperature2F5I 780g, stirring is opened, led to
Enter tetrafluoroethene, be warming up to and start to react, pressure is about 2MPa when being increased to 110 DEG C, treats that pressure drops to 1.8MPa in kettle
When, it is 2MPa to be passed through tetrafluoroethene to pressure again, is repeated several times, reacts to pressure and no longer change, cooling, and recovery is unreacted
C2F5I, obtain product C2F5(CF2CF2)nThe common 125g of I.Product passes through alkali cleaning, and Gc-mss product is used after dewater treatment
Middle each component and its ratio are shown in Table 2.
The analysis result of table 2
| Chain length (n) | Ratio (%) |
| 2 | 31 |
| 3 | 19 |
| Other | 50 |
Other parts are mainly n>3 product.
Comparative example 1 and comparative example 1 it may be clearly seen that, in the case where other conditions are essentially identical, when add three
After phenyl phosphorus catalyst, the yield of perfluoroalkyl iodide telomer is brought up to 190 grams of embodiment 1 by the 125g of comparative example 1, together
When medium chain C2F5(CF2CF2)nI (n=2-3) content also greatly improves, it was demonstrated that co-catalyst is effectively improved reaction
Conversion ratio and the selectivity to medium chain product.
Embodiment 2
600mL stainless steel vertical response kettles, glass putty 8g, tributylphosphine 2g are added after drying water removal.Used again after kettle is evacuated
Drying nitrogen replaces deoxygenation, and oxygen content reaches below 10ppm.Used additives pump adds C into kettle at room temperature2F5I 800g, open
Stirring, is passed through tetrafluoroethene, is warming up to and starts to react, pressure is about 2MPa when being increased to 95 DEG C, treats that pressure drops in kettle
During 1.7MPa, it is 1.9MPa to be passed through tetrafluoroethene to pressure again, is repeated several times, reacts to pressure and no longer change, and is cooled, recovery
Unreacted C2F5I, obtain product C2F5(CF2CF2)nThe common 186g of I.Product passes through alkali cleaning, and gas chromatography mass spectrometry is used after dewater treatment
Each component and its ratio are shown in Table 3 in analysis product.
The analysis result of table 3
| Chain length (n) | Ratio (%) |
| 2 | 43 |
| 3 | 20 |
| Other | 34 |
Other parts are mainly n>3 product.
Comparative example 2
600mL stainless steel vertical response kettles, glass putty 8g is added after drying water removal.Replaced again with drying nitrogen after kettle is evacuated
Deoxygenation, oxygen content reach below 10ppm.Used additives pump adds C into kettle at room temperature2F5I 800g, stirring is opened, is passed through four
PVF, it is warming up to and starts to react, when being increased to 110 DEG C, pressure is about 2MPa, when pressure drops to 1.8MPa in kettle, then
Secondary tetrafluoroethene to the pressure that is passed through is 2MPa, is repeated several times, reacts to pressure and no longer change, and cooling, reclaims unreacted C2F5I,
Obtain product C2F5(CF2CF2)nThe common 100g of I.Product passes through alkali cleaning, and each group in Gc-mss product is used after dewater treatment
Divide and its ratio is shown in Table 4.
The analysis result of table 4
| Chain length (n) | Ratio (%) |
| 2 | 27 |
| 3 | 14 |
| Other | 49 |
Other parts are mainly n>3 product.
Comparative example 2 and comparative example 2 can be clearly seen that, in the case where other conditions are essentially identical, when addition three
After butyl phosphine co-catalyst, the yield of perfluoroalkyl iodide telomer by 100 grams of comparative example 2 bring up to embodiment 2 186 grams,
Increase 86 weight %, while the C of medium chain2F5(CF2CF2)nI (n=2-3) content also greatly improves.
Claims (10)
1. a kind of synthetic method of medium chain perfluoroalkyl iodide telomer, it is characterised in that comprise the following steps：Hold to reaction
Polymerized monomer CF is added in device2=CR1R2, telogen RfI, metallic catalyst and co-catalyst carry out polymerisation and obtain carbon atom
Number is 3~14 perfluoroalkyl iodide telomer, and it has below formula：Rf(CF2CR1R2)nI, wherein, RfFor C1-8Perfluoroalkyl；
R1、R2It may be the same or different, each be selected from fluorine atom, C1-4Saturation perfluoroalkyl；N=1-6 integers；The co-catalyst is
PR1R2R3, R1、R2、R3It may be the same or different, selected from alkyl and aryl.
A kind of 2. synthetic method of medium chain perfluoroalkyl iodide telomer according to claim 1, it is characterised in that Rf
For C1-4Perfluoroalkyl, n=1-4 integers.
3. a kind of synthetic method of medium chain perfluoroalkyl iodide telomer according to claim 1 or 2, its feature exist
In the C1-4Saturation perfluoroalkyl be selected from perfluoro-methyl, perfluoro-ethyl, perfluor n-propyl, perfluoroisopropyl, perfluoro-n-butyl group,
One kind in perfluor isobutyl group and perfluoro-t-butyl.
A kind of 4. synthetic method of medium chain perfluoroalkyl iodide telomer according to claim 3, it is characterised in that institute
State polymerized monomer be selected from tetrafluoroethene, hexafluoropropene, 2- trifluoromethyls perfluoropropene, α-perfluor hexene and 2- trifluoromethyl-alphas-
One kind in perfluorobuttene.
5. a kind of synthetic method of medium chain perfluoroalkyl iodide telomer according to claim 1 or 2, its feature exist
In the RfSelected from perfluoro-methyl, perfluoro-ethyl, perfluor n-propyl, perfluoroisopropyl, perfluoro-n-butyl group, perfluor isobutyl group, complete
One kind in the fluorine tert-butyl group, perfluor n-pentyl, perfluor isopentyl, perfluor n-hexyl and perfluor dissident's base.
6. a kind of synthetic method of medium chain perfluoroalkyl iodide telomer according to claim 1 or 2, its feature exist
In the mol ratio of the polymerized monomer and telogen is 1：99-15：85, preferably 5：95-10：90.
7. a kind of synthetic method of medium chain perfluoroalkyl iodide telomer according to claim 1 or 2, its feature exist
In the dosage of the catalyst is 0.5~10%, preferably the 1~5% of telogen quality.
8. a kind of synthetic method of medium chain perfluoroalkyl iodide telomer according to claim 1 or 2, its feature exist
In the co-catalyst is triphenylphosphine or tributylphosphine.
9. a kind of synthetic method of medium chain perfluoroalkyl iodide telomer according to claim 1 or 2, its feature exist
In based on the metallic catalyst, the dosage of co-catalyst is 10-50 weight %, preferably 15-30 weight %, more preferably 20-
28 weight %.
10. a kind of synthetic method of medium chain perfluoroalkyl iodide telomer according to claim 1 or 2, its feature exist
In polymeric reaction temperature is 60-150 DEG C, pressure 0.5-5MPa.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113388243A (en) * | 2021-06-24 | 2021-09-14 | 华南理工大学 | Antibacterial polycarbonate and preparation method and application thereof |
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| CN103880588A (en) * | 2014-02-26 | 2014-06-25 | 巨化集团技术中心 | Method for preparing perfluoroalkyl iodine through catalytic distillation telomerization |
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| CN1275969A (en) * | 1997-10-14 | 2000-12-06 | 纳幕尔杜邦公司 | Thermal process for preparation of telomeric alkyl iodide |
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| CN113388243A (en) * | 2021-06-24 | 2021-09-14 | 华南理工大学 | Antibacterial polycarbonate and preparation method and application thereof |
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Application publication date: 20180306 |