WO2002036530A1 - Processus de production de telomere de iodure perfluoroalkyle - Google Patents

Processus de production de telomere de iodure perfluoroalkyle Download PDF

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Publication number
WO2002036530A1
WO2002036530A1 PCT/JP2001/009533 JP0109533W WO0236530A1 WO 2002036530 A1 WO2002036530 A1 WO 2002036530A1 JP 0109533 W JP0109533 W JP 0109533W WO 0236530 A1 WO0236530 A1 WO 0236530A1
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WO
WIPO (PCT)
Prior art keywords
reaction
filter
reactor
catalyst
telogen
Prior art date
Application number
PCT/JP2001/009533
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English (en)
Japanese (ja)
Inventor
Yoshio Funakoshi
Tatsuya Ohtsuka
Original Assignee
Daikin Industries, Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Daikin Industries, Ltd. filed Critical Daikin Industries, Ltd.
Priority to JP2002539292A priority Critical patent/JP4158522B2/ja
Publication of WO2002036530A1 publication Critical patent/WO2002036530A1/fr

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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
    • 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

Definitions

  • the present invention relates to a method for continuously producing perfluoroalkyl iodide telomer and a reactor used for such a method.
  • Perfluoroalkyl iodide telomers having a linear or branched perfluoroalkyl group having about 6 to 12 carbon atoms are useful as a raw material for surfactants and as a raw material for water- and oil-repellent treatment agents for fibers. Compound.
  • Perfluoroalkyl iodide telomers generally have the formula 1:
  • R f is a perfluoroalkyl group having 1 to 6 carbon atoms, and n is an integer of 1 to 4.
  • telomerization reaction Since this telomerization reaction is an endothermic reaction, it is necessary to heat the reaction to advance the reaction.However, if the temperature is excessively high, the reaction proceeds excessively, and in the reaction represented by the formula 1, n Unintended telomers with a value of 5 or more may be produced. Therefore, a method using various catalysts for the purpose of preventing an excessively high temperature and performing a reaction at a relatively low temperature is known in the prior art. Disclosure of the invention
  • Dit Patent Publication No. 1,444,517 states that in a tubular reactor, at a temperature in the range of 250-800 ° C and a pressure in the range of 2 mmHg to 5 atmospheres. A method of reacting with a residence time of 1 hour or less is disclosed. This reaction is carried out at a high temperature, and the perfluoroalkyl radical generated is liable to dimerize. However, there is a problem that perfluoroalkane, which is a dimer of perfluoroalkyl radical, is produced in a large amount.
  • U.S. Patent No. 5,068,471 discloses a telomerization reaction initiated with a free radical generator. This reaction is based on the formula 2 where the free radical generator used is used as a telogen:
  • R f ′ is a perfluoroalkyl group having 1 to 6 carbon atoms.
  • the number of taxogens added to one molecule of telogen is larger than a desired value, and a telomer having a chain length longer than a desired chain length, for example, the following formula 4:
  • R f ′ is the same as in Formula 2, and m is an integer of 5 or more.
  • JP-A-8-239335 and JP-A-8-239336 disclose zinc, magnesium, vanadium, rhodium, rhenium, silver, or zinc as a catalyst for the telomerization reaction. It is described that a catalyst obtained by adding a small amount of transition metal to the above-mentioned metal is used. In these methods, a catalyst in which a metal is supported on a carrier such as alumina or zeolite is used, and the raw material is passed through a tubular reactor filled with such a catalyst by a relatively simple method. However, there is an advantage that the telomerization reaction can be continuously performed.
  • the present invention relates to a method for producing a perfluoroalkyl iodide telomer by a telomerization reaction using perfluoroalkyl iodide as a telogen and tetrafluoroethylene as a taxogene. It is an object of the present invention to solve such various problems and to provide a method which can be carried out continuously on an industrial scale.
  • batch type J means that after a telomerization reaction is performed using a predetermined amount of raw materials in a reaction apparatus, the reaction is terminated. To remove the reaction product.
  • continuous means that the reaction product is taken out without interrupting the telomerization reaction while introducing the raw materials into the reactor. '
  • Another object of the present invention is to provide a reactor used for carrying out a method for producing a perfluoroalkyliodide telomer which does not have the above-mentioned problems.
  • the present invention provides a method for preparing a compound of formula 5 as a telogen in a reactor in which a catalyst is present:
  • R f is a perfluoroalkyl group having 1 to 6 carbon atoms.
  • R f is the same as in Formula 5, and n is an integer of 1 to 4.
  • the reaction solution is filtered using a filter arranged so as to be immersed in a reaction solution containing a perfluoroalkyl iodide telomer obtained by the telomerization reaction and a catalyst.
  • a filter arranged so as to be immersed in a reaction solution containing a perfluoroalkyl iodide telomer obtained by the telomerization reaction and a catalyst.
  • the reaction solution containing the perfluoroalkylalkylide telomer and the catalyst obtained by the telomerization reaction contains the starting materials telogen (usually in liquid phase) and taxogen (usually in liquid phase and Z or gas phase). And telogen and taxogen not consumed in the reaction, and perfluoroalkyl iodide telomer product formed by the telomerization reaction (usually a liquid phase, n And the catalyst used for this telomerization reaction, as well as any other by-products that may be formed.
  • the present invention provides a reactor for use in the above-described telomerization reaction method, comprising: a stirrer; at least one conduit for introducing a raw material; A filter selected from the group consisting of a filter, a sintered wire mesh filter, a porous ceramic filter, a wire slit filter, a metal membrane filter and a metal fiber filter; and a conduit for discharging a liquid phase passing through the filter. It is characterized by having a reaction device provided.
  • FIG. 1 schematically shows an apparatus for implementing one preferred embodiment of the present invention.
  • FIG. 2 is a diagram schematically showing an apparatus for carrying out another preferred embodiment of the present invention.
  • FIG. 3 is a diagram schematically showing one preferred embodiment of the filter used in the present invention.
  • FIG. 4 is a diagram schematically showing another preferred embodiment of the filter used in the present invention.
  • FIG. 1 shows a schematic diagram of an apparatus implementing one preferred embodiment of the present invention.
  • the reactor 1 is equipped with a stirrer 11 and the reactor 1 is equipped with conduits 2 and 3 for introducing raw materials and a conduit 5 for discharging the filtered liquid phase.
  • a filter 4 is connected to one end of the conduit 5, and the filter 14 is detached or damaged even if the liquid substance is agitated at a portion where the liquid substance is immersed in the reactor 1 in a predetermined amount.
  • the reactor 1 is preferably a caro-pressure sealed type so that tetrafluoroethylene (taxogen), which is a raw material in a gas phase, can be introduced and subjected to a reaction in the reactor 1.
  • taxogen tetrafluoroethylene
  • the flow rate of the gaseous tetrafluoroethylene, which is a taxogen, is adjusted from a tank or the like (not shown) by a valve or the like, and is supplied to the reactor 1 through the conduit 2.
  • the liquid phase perfluoroalkyl iodide, which is a telogen, is supplied to the reactor 1 through the conduit 3 at a controlled flow rate by, for example, a pump 30.
  • the catalyst is, for example, of a predetermined quality and quantity introduced into the reactor before starting the reaction.
  • a preferred catalyst for use in the present invention is copper powder.
  • the catalyst particles have a particle size of 0.1 / m to 1 mm, preferably 20 ⁇ to 0.3 mm, and 20 ⁇ ! Those having an average particle diameter of from 200 m to 200 m, preferably from 45 m to 100 m are used.
  • the form of the particles is not particularly limited, and the form of the particles obtained by physically processing a copper lump, such as cutting or pulverization, and the electrical and / or chemical conversion from an electrolyte containing copper ions. It may be in various forms such as the form of particles obtained by precipitation.
  • a copper powder for example, a copper powder called first-grade copper powder 325 mesh which is commercially available as a reagent from Kishida Chemical Co., Ltd. can be used.
  • the particle size and average particle size of the catalyst particles are not always determined to a specific value or range, but are determined by a relative relationship with the maximum pore size of the filter used. Therefore, it is actually selected in combination with the final letter to be used.
  • telomerization reaction to be carried out in the present invention can be used as a catalyst.
  • materials include, for example, zinc, magnesium, vanadium, rhenium, rhodium, ruthenium, platinum, silver, or a material obtained by adding a small amount of transition metal to these metals, such as an alloy having such a composition. .
  • a mixture of the copper powder and these substances can be used as a catalyst.
  • the particle diameter and average particle diameter as described above for copper powder are used. It is necessary to have
  • telomerization reaction After introducing a catalyst of a predetermined quality and quantity into the reactor 1 and setting the inside of the reactor 1 to a predetermined condition, by introducing telogen and Z or taxogen of the original family, A telomerization reaction can be opened.
  • the catalyst to be used and a predetermined amount of telogen are first charged to the reactor 1 ⁇ , and the taxogen is supplied through the conduit 2, thereby completing the batch type telomerization reaction as an initial state. .
  • a predetermined ratio of the telomer is present in the reactor 1.
  • the raw materials taxogen and telogen are supplied to the reactor 1 at predetermined flow rates through the conduits 2 and 3, respectively, while continuing to stir the reactor.
  • the raw materials taxogen and telogen are supplied to the reactor 1 at predetermined flow rates through the conduits 2 and 3, respectively, while continuing to stir the reactor.
  • the reaction solution containing the raw material, the catalyst, and the product flows into the filter 4 installed in the reactor 1, and the catalyst Is separated by the filtering action of the filter 4 and is left outside the filter 14, and the liquid phase of the reaction solution containing the raw material and the product can pass through the inside of the filter 4.
  • the taxogen is introduced into the reactor 1 in such a ratio as to be used for the reaction in a relatively short time when the taxogen is introduced into the reactor 1, in a quantitative ratio to the telogen. It can be considered that taxogen is not substantially contained in the reaction solution permeating into the inside. Therefore, the raw material in the reaction liquid flowing into the inside of the filter 4 can be considered to be substantially telogen.
  • the liquid phase flowing into the filter 4 is taken out of the reactor 1 through the conduit 5 by, for example, a pump (not shown), and sent to, for example, a distillation unit (not shown) to obtain the target perfluoroelastomer.
  • the product is separated into low alkyl iodide telomer products and unreacted tetangen as raw materials, and each substance is collected and sent to a specified storage tank. Or sent to a designated line (not shown) for recycling.
  • the concentration of the taxogen in the reaction solution can be made relative to the concentration of the lipogen. It is possible to form a state in which the value is kept within a certain low range, and the state can be maintained for a long time.
  • the reaction conditions in which a telomer having a desired molecular weight range (accordingly, the degree of polymerization) is easily generated in the reaction solution can be maintained for a long time.
  • the telomere having a desired molecular weight range (and thus the degree of polymerization) can have a relatively high conversion rate.
  • high yields can be achieved for telomers having the desired molecular weight range.
  • the method of the present invention is particularly advantageous when applied to a continuous reaction, but can also be used for a batch reaction.
  • the operation of separating the catalyst from the reaction solution containing the reaction product can be performed without using a separate filtration device, so that the filtration step is omitted. Equipment and labor can be saved.
  • the type of perfluoroalkyl iodide telomer which is the product, is determined by the type of telogen and taxogen used.
  • telogen / taxogen for example, the following combination:
  • 1-Edoperfluoretane From the combination of tetrafluoroethylene, 1-Edoperfluorene, 1 _Edoperfurnoleohexane, 1-Edoperfluorooctane, 1-Ed Puff, leolodecane,
  • telogen of the present invention pure telogen alone, a mixture of telogen and lower telomer, or a mixture of lower telomers is used. By using the mixture, the desired perfluoroalkyl iodide can be obtained.
  • Certain conditions for carrying out the method according to the invention as described above include: 60 to 200 ° C., preferably 120 to: L 60 ° C., 0.1 to 5 MPa , Preferably 1.0 to 3.0 OMPa.
  • the conditions for filtering the reaction solution are set so that the linear velocity of the reaction solution per unit area per unit area of the filter is usually 0.01 to 10 mZhr, especially 0.6 to 6 mZhr. Is preferred. If the filtration linear velocity of the reaction solution is 0.01 m / hr or less, an undesired long-chain telomer is likely to be generated due to an increase in the residence time of the reaction solution, which is not preferable. When the filtration linear velocity is 10 m / hr or more, the ratio of the raw material that flows out unreacted becomes too large, and the catalyst is easily accumulated on the filtration surface of the filter. It is not preferable because it causes a rise in
  • the substances involved in the telomerization reaction of the present invention dissolve copper catalyst as a solid phase, taxogen as a gas phase or a liquid phase (depending on pressure conditions), telogen and taxogen as a liquid phase.
  • Telogen, telomer as liquid phase telomere A mixture of the telomer and the telogen as a liquid phase. Therefore, when the taxogen is supplied to the reactor as a gas phase, it is a three-phase reaction of a gas phase, a liquid phase and a solid phase, and a mixture obtained by dissolving the taxogen in the telogen is supplied to the reactor. In this case, it is a two-phase reaction with one liquid phase and one solid phase.
  • the filter used in the method for producing a perfluoroalkyl iodide telomer of the present invention has pores with an opening degree that does not substantially pass through a solid phase (catalyst particles) and a solid phase (catalyst particles).
  • a porous filter is used in which clogging of pores due to) is substantially prevented.
  • the filter has pores with an opening degree that does not substantially pass through the solid phase (catalyst particles), and clogging of the pores by the solid phase (catalyst particles) is substantially prevented.
  • the maximum value of the opening size in the pores of the filter is set to a size smaller than the minimum value of the size of the catalyst particles to be separated, preferably a very small size. Therefore, it is important to select the opening size in the pores of the filter for use in the present invention according to the size of the catalyst particles to be used.
  • the catalyst particles are subjected to an operation such as classification in advance, and the minimum value of the particle size is set so as to be equal to or greater than a predetermined value.
  • the setting includes preparing the catalyst particles as described above and confirming that the catalyst particles already have such dimensions.
  • the solid phase (catalyst particles) is formed on the surface of the filter and in the Z or wall. Due to the accumulation and clogging of the filter, the pressure loss in the solid-liquid separation (filtration) operation becomes large, and the product cannot be taken out of the reactor, so that the telomerization reaction can be continuously performed. It is possible to prevent a situation where the operation cannot be performed.
  • the above-mentioned filter is disposed so as to be immersed in the reaction solution in the reaction apparatus throughout the period in which the telomerization reaction is performed.
  • the reaction solution is stirred by the stirring device 11 inside the reaction device 1, so that it once reaches the filter surface together with the reaction solution, and only the liquid phase of the reaction solution is filtered.
  • the catalyst particles are left on the surface of the filter by permeation into the interior of the filter, and the catalyst particles left on the surface of the filter are removed from the surface of the filter by the force exerted by the flow of the agitated liquid. And dispersed again in the reaction solution.
  • a predetermined force is applied to the filter by the flowing liquid, the filter itself is prevented from being deformed or damaged by such a force.
  • One such filter is a sintered metal filter, a sintered wire mesh filter, a porous ceramic filter, a wire slit filter, a metal membrane filter, and a finoletter selected from the group of metal fiber filters.
  • the material forming the filter whether a metal material, an inorganic material, or an organic material, does not adversely affect the telomerization reaction of the present invention. Is selected.
  • a metal material SUS-304, SUS-316, copper-tin alloy, etc.
  • a material for the finoletor can be selected from PTFE finoleta and the like.
  • FIG. 3 shows one preferred embodiment of the filter, which is formed in a cylindrical shape.
  • This shows a sintered metal filter in which the entire outer wall portion is formed by sintering metal particles.
  • This filter is formed in a cylindrical shape as a whole, and the entire wall including the side and bottom surfaces is formed of sintered metal particles, so that the entire wall is porous. I have. Thus, the entire wall of the filter is used for filtration.
  • the maximum size of the pores of the filter thus formed can be controlled, for example, by appropriately selecting the particle size of the metal material and / or the inorganic material used for sintering and the sintering conditions. .
  • the use of such a filter has the advantage that a filter having desired pores can be easily and inexpensively manufactured.
  • FIG. 4 shows another preferred embodiment of the filter, which is a cylindrical filter having cylindrical side surfaces and a top surface formed of, for example, non-porous ceramic, and a sintered wire mesh on a bottom portion thereof. Shows the filter to which the component is attached.
  • the sintered wire mesh member on the bottom surface of the filter has the porosity required for the filter used in the present invention as described above. Therefore, in this filter, the bottom surface is used for filtration. By using such a filter, accumulation of the catalyst on the filter filtration surface can be prevented. Further, even if the liquid level of the reaction solution in the reaction apparatus may be lowered, the advantage is obtained that the method of the present invention can be carried out as long as the bottom surface of the cylindrical filter is below the height of the liquid level. .
  • the filters shown in FIGS. 3 and 4 are merely preferred examples of filters, and the shape or form of the filter may be a fixed one such as a sphere, a spheroid (the shape of a rugby pole), a cube, or a rectangular parallelepiped. Not only shapes represented by geometric names, but also various shapes or forms, such as combinations of these various geometric shapes or various geometric shapes in whole and / or portions, may be employed. it can.
  • a configuration as shown in FIG. 2 can be adopted.
  • the tip of the conduit 2 does not reach the inside of the reactor 1, and the conduit 2 is connected to the conduit 3 in a portion 31 of the conduit 3 upstream of the reactor 1. Therefore, the taxogen supplied through the conduit 2 is introduced into the conduit 3 via the connection 31 and mixed with the telogen sent from the left side of the conduit in the conduit 3 to react. Sent to location 1.
  • a valve such as a check valve may be provided as necessary between the conduit 2 and the connection portion 31 and upstream of the connection portion 31 in the Z or the conduit 3 so that the taxogene or the It is also possible to supply only one of the substances to the reactor 1.
  • telomerization reaction of the present invention since the introduction rate or flow rate of telogen and taxogen as raw materials and the discharge rate or flow rate of the reaction solution fluctuate depending on the required telomer distribution, it is necessary to maintain a constant flow rate. Can not be determined.
  • the average residence time of telogen and taxogene in the reactor 1 and the telogen present in the reactor 1 are considered to be suitable for generating the target telomerization reaction product in the reactor 1.
  • the introduction flow rate of telogen and taxogen as raw materials and the discharge flow rate of the reaction solution can be selected.
  • the average residence time of telogen and taxogen in the reactor 1 can be determined in advance by preliminary experiments, and the average residence time depends on the speed or flow rate of the reaction solution flowing out of the reactor 1 through the conduit 5. By adjusting, it can be easily adjusted. Therefore, it is preferable to supply the raw materials such that the amount of the reaction solution in the reactor 1 is kept substantially constant according to the outflow speed of the reaction solution.
  • Examples and Comparative Examples of the telomerization reaction of the present invention will be described in more detail.
  • Example 1 The telomerization reaction was performed using the reactor shown in FIG.
  • the stirring tank type reaction apparatus 1 an autoclave apparatus having a capacity of 25 Om1 and having a stirrer was used.
  • the filter 4 a filter formed into a cylindrical shape as shown in FIG. 3, having a diameter of 12 mm and a height of 17 mm, and having a wall formed of a sintered metal was used.
  • the reactor 1 was supplied with 1-node perfluoroethane at a flow rate of 240 g / hr through the conduit 2 and tetrafluoroethylene at a flow rate of 8.48 g / hr through the conduit 3. And conducted a telomerization reaction.
  • the distribution of the degree of polymerization of the telomer product [the value of n in (C 2 F 5 (CF 2 CF 2 ) n I)] at 6 hours after the start of the introduction of the taxogen was measured. The results are shown in Table 1. Analysis of telomers was performed by gas chromatography after the reaction was cooled.
  • telogen 1-d-perfluoroyl loethane
  • 10 grams of copper powder were charged into reactor 1, and the same temperature conditions and pressures as in Example 1 were used.
  • a telomerization reaction was performed under the conditions.
  • tetrafluoroethylene was introduced while maintaining the pressure in the reactor at 1.9 MPa, but only tetrafluoroethylene consumed by the reaction was sequentially replenished.
  • the reaction was stopped when 8.6 g of tetrafluoroethylene was introduced, and the distribution of the degree of polymerization of the telomer product [the value of n in (C 2 F 5 (CF 2 CF 2 ) n I)) at that point was measured. .
  • the results are shown in Table 1.
  • telogen 1-doped perfluoroethane
  • copper powder a reagent manufactured by Kishida Chemical Co., Ltd., first grade copper powder 325mesh
  • TFE tetrafluoroethylene
  • the reaction was performed continuously for a maximum of 670 hours, but no clogging of the filter occurred, and the telomerization reaction to be performed in the present invention could be smoothly performed throughout the reaction. .

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un processus de production de télomère de iodure perfluoroalkyle qui consiste à soumettre une iodure perfluoroalkyle en tant que télogène et du tétrafluoroéthylène à une réaction de télomérisation dans un réacteur contenant un catalyseur. Ce processus est caractérisé par le fait qu'un mélange de réaction liquide contenant un télomère de iodure perfluoroalkyle de produit de réaction, le catalyseur et les matériaux bruts sont filtrés à l'aide d'un filtre agencé de façon à pouvoir être immergé dans le mélange de réaction, et le catalyseur séparé est recyclé dans le système de réaction, pendant le retrait d'une phase liquide ne contenant sensiblement plus de catalyseur vers l'extérieur du réacteur. Les matériaux bruts sont séparés de la phase liquide à l'extérieur du réacteur et recyclés dans ce réacteur.
PCT/JP2001/009533 2000-11-02 2001-10-31 Processus de production de telomere de iodure perfluoroalkyle WO2002036530A1 (fr)

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JP2002539292A JP4158522B2 (ja) 2000-11-02 2001-10-31 パーフルオロアルキルアイオダイドテロマーの製造方法

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JP2000-335709 2000-11-02
JP2000335709 2000-11-02

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002316956A (ja) * 2001-04-17 2002-10-31 Daikin Ind Ltd パーフルオロアルキルアイオダイドテロマーの製造方法
US7888538B1 (en) 2009-11-04 2011-02-15 E.I. Du Pont De Nemours And Company Catalyzed olefin insertion
US7951983B2 (en) 2009-11-04 2011-05-31 E.I. Du Pont De Nemours And Company Catalyzed olefin insertion
WO2013157329A1 (fr) 2012-04-19 2013-10-24 ダイキン工業株式会社 Procédé de production d'un mélange d'iodures de fluoroalkyle
CN103373895A (zh) * 2012-04-19 2013-10-30 大金工业株式会社 氟烷基碘化物的制造方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0433988A2 (fr) * 1989-12-21 1991-06-26 Hoechst Aktiengesellschaft Procédé de telomérisation continue
JPH0568869A (ja) * 1991-09-10 1993-03-23 Asahi Chem Ind Co Ltd 懸濁触媒系の反応方法
EP0718262A1 (fr) * 1994-12-24 1996-06-26 Hoechst Aktiengesellschaft Procédé pour la préparation de télomères d'iodure de perfluoroalkyle
US5639923A (en) * 1994-12-24 1997-06-17 Hoechst Aktiengesellschaft Metal-catalyzed preparation of perfluoroalkyl iodide telomers

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0433988A2 (fr) * 1989-12-21 1991-06-26 Hoechst Aktiengesellschaft Procédé de telomérisation continue
JPH0568869A (ja) * 1991-09-10 1993-03-23 Asahi Chem Ind Co Ltd 懸濁触媒系の反応方法
EP0718262A1 (fr) * 1994-12-24 1996-06-26 Hoechst Aktiengesellschaft Procédé pour la préparation de télomères d'iodure de perfluoroalkyle
US5639923A (en) * 1994-12-24 1997-06-17 Hoechst Aktiengesellschaft Metal-catalyzed preparation of perfluoroalkyl iodide telomers

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002316956A (ja) * 2001-04-17 2002-10-31 Daikin Ind Ltd パーフルオロアルキルアイオダイドテロマーの製造方法
US7888538B1 (en) 2009-11-04 2011-02-15 E.I. Du Pont De Nemours And Company Catalyzed olefin insertion
US7951983B2 (en) 2009-11-04 2011-05-31 E.I. Du Pont De Nemours And Company Catalyzed olefin insertion
WO2013157329A1 (fr) 2012-04-19 2013-10-24 ダイキン工業株式会社 Procédé de production d'un mélange d'iodures de fluoroalkyle
JP2013221026A (ja) * 2012-04-19 2013-10-28 Daikin Industries Ltd フルオロアルキルアイオダイドの混合物の製造方法
CN103373895A (zh) * 2012-04-19 2013-10-30 大金工业株式会社 氟烷基碘化物的制造方法
CN104245643A (zh) * 2012-04-19 2014-12-24 大金工业株式会社 氟烷基碘的混合物的制造方法
KR20150004370A (ko) 2012-04-19 2015-01-12 다이킨 고교 가부시키가이샤 플루오로알킬 요오다이드의 혼합물의 제조 방법
US9212110B2 (en) 2012-04-19 2015-12-15 Daikin Industries, Ltd. Method for producing mixture of fluoroalkyl iodides

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