CN107556202A - A kind of fluoroalkyl aminated compounds and preparation method thereof - Google Patents

A kind of fluoroalkyl aminated compounds and preparation method thereof Download PDF

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CN107556202A
CN107556202A CN201710762903.7A CN201710762903A CN107556202A CN 107556202 A CN107556202 A CN 107556202A CN 201710762903 A CN201710762903 A CN 201710762903A CN 107556202 A CN107556202 A CN 107556202A
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万耀明
梁璐
熊瑜
张玉忠
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AECC Beijing Institute of Aeronautical Materials
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Abstract

The present invention is a kind of fluoroalkyl aminated compounds and preparation method thereof, belongs to organic compound synthesis technical field and technical field of coatings.Its method prepared is the fluothane hydrocarbon using the functional group of sulfuryl fluoride containing both-end as initial reactant, pass through group conversion reaction, sulfonyl fluoride group is progressively converted into sulfinate, halogen atom, halogenated alkyl hydrocarbon or alkyl p-methyl benzenesulfonic acid base and final end amido (primary amine or secondary amine), the fluothane hydrocarbon curing agent of both-end amino-contained is obtained, has important application prospect in coatings with high weatherability technical field.

Description

A kind of fluoroalkyl aminated compounds and preparation method thereof
Technical field
The present invention relates to a kind of fluoroalkyl aminated compounds and preparation method thereof, belong to technical field of chemistry.This kind of fluothane Base aminated compounds can be applied to fighter plane infrared stealth epoxy resin coating or other require high-weatherability energy coating.
Background technology
Infrared stealth coating is mainly by the functional filler with low-launch-rate and the macromolecule with infrared transparent Resin material forms.Adhesive of the resin as functional filler, it is the main film forming substance of coating, its performance quality is to hidden The regulation and control of body coatings emissivity are with stably having material impact.Substantial amounts of research shows, infrared stealth coating in use, The aging of coating resin can make infrared emittance have obvious ascendant trend and ultimately result in stealthy failure.Therefore, it is red in guarantee It is outer the transparency on the premise of further lifting resin ageing-resistant performance be in infrared stealth coating field one it is highly important Research topic.In recent years, with advances in technology, the existing commercialized product of the epoxy resin of weatherability, but weather-proof solid The progress in agent field then relatively slowly, the exploitation of the fluorine-containing curing agent particularly with excellent weathering resistance then phase To less.Fluorochemical has very high infrared transparent, disclosure satisfy that the requirement of infrared stealth coating, and it is weather-proof The best a kind of organic compound of performance.Curing agent made from fluorochemical is used for the solidification of weathe resistance epoxy resin, energy The excellent infrared stealth coating resin matrix of weather resistance is enough prepared, solves infrared stealth coating because resin binder is old Change and caused by infrared stealth hydraulic performance decline or lose the problem of, lifted China's military equipment infrared stealth performance long-term effect With stability, extend camouflage coating service life.
The content of the invention
The present invention is exactly to design for above-mentioned prior art situation and provide a kind of fluoroalkyl aminated compounds and its system Preparation Method, it can be made with excellent weathering resistance infrared stealth coating tree using this kind of compound and with reference to weathe resistance epoxy resin Aliphatic radical body, solve the problems, such as infrared stealth coating because resin binder aging and caused by infrared stealth hydraulic performance decline or lose.
The molecular structural formula of fluoroalkyl aminated compounds of the present invention is：
In formula, it is 1~10 that a, b, c, n, which can use number range,；
Z1、Z2For hetero atom or difluoro methylene, wherein hetero atom is O, S or Se；
R substituent is hydrogen, methyl, ethyl, propyl group, normal-butyl, the tert-butyl group, sec-butyl, amyl group, cyclohexyl, hexyl, benzene The aryl that base, benzyl or phenyl ring are substituted by other substituents.
The method for proposing to prepare this kind of fluoroalkyl aminated compounds in technical solution of the present invention is as follows the step of this method：
Step 1: being reacted to obtain intermediate II by compound I, reaction equation is as follows：
Course of reaction is will wait stoichiometric compound I, reducing agent and 2~10 times of stoichiometric solvents I, certain Through extracting, concentrating or be recrystallized to give intermediate II after certain reaction time under temperature conditionss, the solvent I be water, One or more of mixtures in ether, dichloromethane, dioxane, acetonitrile or tetrahydrofuran, temperature range are 25~150 DEG C, the reducing agent is sodium sulfite, and potassium sulfite, sodium borohydride or sodium dithionite, the reaction time is 2~12h；
Step 2: being reacted to obtain intermediate III by intermediate II, reaction equation is as follows：
Course of reaction is that will wait stoichiometric intermediate II, halide reagent and 2~10 times of stoichiometric polar solvents, React to obtain intermediate III in heating condition, the halide reagent is bromine, iodine, chlorine or sulfonic acid chloride, and polar solvent is second Nitrile, water, acetic acid, sulfonic acid chloride, dimethyl sulfoxide (DMSO), N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, tetrahydrofuran, methanol Or one or more of mixtures in ethanol, heating temperature range are 60~120 DEG C, post-reaction treatment is to add water stratification；
Step 3: being reacted to obtain intermediate compound IV by intermediate III, reaction equation is as follows：
Course of reaction for will wait stoichiometric intermediate III, allyl compound, diiodomethane or
Ethylidene periodide class compound, radical initiator and 2~10 times of stoichiometric solvents II, in certain temperature condition Lower reaction obtains intermediate compound IV, and the functional group Y of the allyl compound is chlorine, bromine, iodine ,-OTs ,-OMs ,-OTfOr-OH, from It is sodium dithionite, benzoyl peroxide, azodiisobutyronitrile, hydrogen peroxide, sodium hydrogensulfite or rongalite by base initiator, Solvent II be acetonitrile, water, N,N-dimethylformamide, dimethyl sulfoxide (DMSO), dichloromethane, chloroform, tetrahydrofuran, methanol or One or more of mixtures in ethanol, temperature range are 0~120 DEG C.
Step 4: intermediate compound IV reacts to obtain fluoroalkyl aminated compounds V, reaction equation is as follows：
Course of reaction be by etc. stoichiometric intermediate compound IV, the alkylamine containing R substituent and 2~10 times it is stoichiometric Solvent III, this kind of fluoroalkyl aminated compounds V, the R substituent are obtained by nucleophilic substitution under the conditions of certain temperature It is hydrogen, methyl, ethyl, propyl group, normal-butyl, the tert-butyl group, sec-butyl, amyl group, cyclohexyl, hexyl, phenyl, benzyl or phenyl ring by it The aryl of his substituent substitution, solvent III are acetonitrile, water, DMF, dimethyl sulfoxide (DMSO), dichloromethane, trichlorine One or more of mixtures in methane, tetrahydrofuran, methanol or ethanol, temperature range are 0~100 DEG C；
In the molecular structural formula of above-mentioned steps：
A, it is 1~10 that b, c, n, which can use number range,；
Z1、Z2For hetero atom or difluoro methylene, wherein hetero atom is O, S or Se；
R substituent is hydrogen, methyl, ethyl, propyl group, normal-butyl, the tert-butyl group, sec-butyl, amyl group, cyclohexyl, hexyl, benzene The aryl that base, benzyl or phenyl ring are substituted by other substituents；
X1, X2It may be selected from following functional group：Halogen, hydroxyl, carboxyl, amino, nitro, aldehyde radical, acyl group, sulfonamide, sulphonyl The common functional groups such as halogen, phosphoamide.
Fluorine-containing curing agent is prepared by the method for organic synthesis in technical solution of the present invention, and molecular weight is smaller, reactivity The designability of functional group is strong, good with resin compatible, and for the solidification of weathe resistance epoxy resin, weatherability can be prepared Can excellent infrared stealth coating resin matrix, solve infrared stealth coating because resin binder aging and caused by it is infrared hidden The problem of body hydraulic performance decline or forfeiture, long-term effect and the stability of the infrared stealth performance of China's military equipment are lifted, is extended hidden Body coating service life.
Embodiment
Technical solution of the present invention is described further below with reference to embodiment.
In the method for preparing described fluoroalkyl aminated compounds, step 1 is to react to obtain intermediate II by compound I, Reaction equation is as follows：
Course of reaction is will wait stoichiometric compound I, reducing agent and 2~10 times of stoichiometric solvents I, certain Through extracting, concentrating or be recrystallized to give intermediate II after certain reaction time under temperature conditionss, the solvent I be water, One or more of mixtures in ether, dichloromethane, dioxane, acetonitrile or tetrahydrofuran, temperature range are 25~150 DEG C, the reducing agent is sodium sulfite, and potassium sulfite, sodium borohydride or sodium dithionite, the reaction time is 2~12h；
The instantiation of the step 1 is as follows：
Step 1 example 1, the reaction of the example are as shown in Equation 1:
Formula 1:
The operating process of the reaction is：In 1L there-necked flask, 200ml acetonitrile, 200ml water, 140g are added The compound Ia, 70g in left side sodium dithionite (0.4mol) in the formula 1 of (0.2mol), the lower 6h of 80 DEG C of stirrings, fluorine spectrum detection Reaction is complete.The extraction of 300ml ethyl acetate is added, concentration, is recrystallized using n-butanol, obtains the intermediate II a120g of crude product, Yield 85%.
Step 1 example 2, the reaction of the example are as shown in Equation 2:
Formula 2:
The operating process of the reaction is：In 1L there-necked flask, 400ml tetrahydrofuran, 23g sodium borohydride are added (0.6mol), the compound Ib in left side in the formula 2 of lower instillation 140g (0.2mol) is stirred at room temperature, 2h, fluorine are reacted after being added dropwise Spectrum detection reaction is complete, pours into extraction in 200ml methanol and goes out and is spin-dried for, and is spin-dried for obtaining the intermediate of crude product after ethyl acetate extraction IIb 128g, yield 91%.
Step 1 example 3, the reaction of the example are as shown in Equation 3:
Formula 3:
The operating process of the reaction is：In 1L there-necked flask, 400ml DMSO is added, in 120g (0.2mol) formula 3 The compound Ic, 50g in left side sodium sulfite (0.4mol), the lower 6h of 100 DEG C of stirrings, fluorine spectrum detection reaction is complete, adds 300ml Ethyl acetate extracts, and concentration, is recrystallized using n-butanol, obtains the intermediate II c 109g of crude product, yield 90%.
Step 1 example 4, the reaction of the example are as shown in Equation 4：
Formula 4:
The operating process of the reaction is：In 1L there-necked flask, 200ml acetonitrile, 200ml water, 153g are added The compound Id, 70g in left side sodium dithionite (0.4mol) in the formula 4 of (0.2mol), the lower 6h of 80 DEG C of stirrings, fluorine spectrum detection Reaction is complete.The extraction of 500ml ethyl acetate is added, concentration, using recrystallisation from isopropanol, obtains the intermediate II d136g of crude product, Yield 88%.
In the method for preparing described fluoroalkyl aminated compounds, step 2 is to be reacted to obtain intermediate by intermediate II III, reaction equation are as follows：
Course of reaction is that will wait stoichiometric intermediate II, halide reagent and 2~10 times of stoichiometric polar solvents, React to obtain intermediate III in heating condition, the halide reagent is bromine, iodine, chlorine or sulfonic acid chloride, and polar solvent is second Nitrile, water, acetic acid, sulfonic acid chloride, dimethyl sulfoxide (DMSO), N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, tetrahydrofuran, methanol Or one or more of mixtures in ethanol, heating temperature range are 60~120 DEG C, post-reaction treatment is to add water stratification；
The instantiation of the step 2 is as follows：
Step 2 example 1, the reaction of the example are as shown in Equation 5：
Formula 5：
The operating process of the reaction is：In 500ML there-necked flask, 71g intermediate II a is added, after substituting nitrogen, The lower acetic acid for adding 100ml of nitrogen protection, 100ml water, 64g bromine, flow back 8h in a heated condition, fluorine spectrum detection, instead System is poured into after answering in 500ml water and be layered, removed layer liquid and wash 3 times, the intermediate of crude product is obtained after drying IIIa 59g, yield 85%.
Step 2 example 2, the reaction of the example are as shown in Equation 6：
Formula 6：
The operating process of the reaction is：In 500ml there-necked flask, 71g intermediate II b is added, after substituting nitrogen, The lower acetonitrile for adding 200ml of nitrogen protection, 54g sulfonic acid chloride, flow back 8h in a heated condition, fluorine spectrum detection, after completion of the reaction System is poured into 1000ml water and is layered, removed layer liquid and wash 3 times, the intermediate III b 48g of crude product are obtained after drying, Yield 80%.
Step 2 example 3, the reaction of the example are as shown in Equation 7：
Formula 7：
The operating process of the reaction is：In 500ml there-necked flask, 61g intermediate II c is added, after substituting nitrogen, The lower ethanol for adding 200ml of nitrogen protection, 102g iodine, flow back 8h in a heated condition, fluorine spectrum detection, after completion of the reaction by body System pours into 1000ml water and is layered, and removes layer liquid and washes 3 times, the intermediate III c 55g of crude product, yield are obtained after drying 80%.
Step 2 example 4, the reaction of the example are as shown in Equation 8：
Formula 8：
The operating process of the reaction is：In 500ml there-necked flask, 77g intermediate II d is added, after substituting nitrogen, The lower ethanol for adding 200ml of nitrogen protection, 102g iodine, flow back 8h in a heated condition, fluorine spectrum detection, after completion of the reaction by body System pours into 1000ml water and is layered, and removes layer liquid and washes 3 times, crude intermediate IIId 65g, yield are obtained after drying 75%.
In the method for preparing described fluoroalkyl aminated compounds, step 3 is to be reacted to obtain intermediate by intermediate III IV, reaction equation are as follows：
Course of reaction for will wait stoichiometric intermediate III, allyl compound, diiodomethane or
Ethylidene periodide class compound, radical initiator and 2~10 times of stoichiometric solvents II, in certain temperature condition Lower reaction obtains intermediate compound IV, and the functional group Y of the allyl compound is chlorine, bromine, iodine ,-OTs ,-OMs ,-OTfOr-OH, from It is sodium dithionite, benzoyl peroxide, azodiisobutyronitrile, hydrogen peroxide, sodium hydrogensulfite or rongalite by base initiator, Solvent II be acetonitrile, water, N,N-dimethylformamide, dimethyl sulfoxide (DMSO), dichloromethane, chloroform, tetrahydrofuran, methanol or One or more of mixtures in ethanol, temperature range are 0~120 DEG C.
The instantiation of the step 3 is as follows：
Step 3 example 1, the reaction of the example are as shown in Equation 9:
Formula 9:
The operating process of the reaction is：In 500ml there-necked flask, 17.4g (0.1mol) sodium dithionite, 8.4g The sodium acid carbonate of (0.1mol), 34.6g (0.05mol) intermediate III a, after substituting nitrogen, is added under nitrogen protection 4h is reacted in 200ml dimethyl sulfoxide (DMSO), 24.2g (0.2mol) allyl bromide, bromoallylene, 100ml water, control at room temperature, and reaction finishes Afterwards, ethyl acetate extraction organic phase, is dried, and concentration, obtains the intermediate compound IV a 27g of crude product, yield 70%.
Step 3 example 2, the reaction of the example are as shown in Equation 10:
Formula 10：
The operating process of the reaction is：In 500ml there-necked flask, 17.4g (0.1mol) sodium dithionite, 8.4g The sodium acid carbonate of (0.1mol), 30g (0.05mol) intermediate III b, after substituting nitrogen, adds 200ml under nitrogen protection Dimethyl sulfoxide (DMSO), 42.5g (0.2mol) pi-allyl p-methyl benzenesulfonic acid ester, react 8h at 50 DEG C, after completion of the reaction, acetic acid second Ester extracts organic phase, dries, and concentration, obtains the intermediate compound IV b 38g of crude product, yield 80%.
Step 3 example 3, the reaction of the example are as shown in Equation 11:
Formula 11：
The operating process of the reaction is：In 500ml there-necked flask, 17.4g (0.1mol) sodium dithionite, 8.4g The sodium acid carbonate of (0.1mol), 34g (0.05mol) intermediate III c, after substituting nitrogen, adds 200ml under nitrogen protection Acetonitrile, 42.5g (0.2mol) pi-allyl p-methyl benzenesulfonic acid ester, 4h is reacted at 20 DEG C, after completion of the reaction, ethyl acetate extraction has Machine phase, dry, concentration, column chromatography, obtain the intermediate compound IV c 28g of crude product, yield 65%.
Step 3 example 4, the reaction of the example are as shown in Equation 12:
Formula 12：
The operating process of the reaction is：In 500ml there-necked flask, 17.4g (0.1mol) sodium dithionite, 8.4g The sodium acid carbonate of (0.1mol), 34g (0.05mol) intermediate III d, after substituting nitrogen, adds 100ml under nitrogen protection Acetonitrile, 11.6g (0.2mol) allyl alcohol, 100ml water, 4h is reacted at 20 DEG C, after completion of the reaction, ethyl acetate extraction is organic Phase, dry, concentration, obtain the intermediate compound IV d 25g of crude product, yield 90%.
In the method for preparing described fluoroalkyl aminated compounds, step 4 is to be reacted to obtain fluoroalkyl amine by intermediate compound IV Class compound V, reaction equation are as follows：
Course of reaction be by etc. stoichiometric intermediate compound IV, the alkylamine containing R substituent and 2~10 times it is stoichiometric Solvent III, fluoroalkyl aminated compounds V is obtained by nucleophilic substitution under the conditions of certain temperature, the R substituent be hydrogen, Methyl, ethyl, propyl group, normal-butyl, the tert-butyl group, sec-butyl, amyl group, cyclohexyl, hexyl, phenyl, benzyl or phenyl ring are taken by other For base substitution aryl, solvent III be acetonitrile, water, DMF, dimethyl sulfoxide (DMSO), dichloromethane, chloroform, One or more of mixtures in tetrahydrofuran, methanol or ethanol, temperature range are 0~100 DEG C；
The instantiation of the step 4 is as follows：
Step 4 example 1, the reaction of the example are as shown in Equation 13:
Formula 13：
The operating process of the reaction is：In 250ml there-necked flask, 50ml ethanol, 4.4g (0.06mol) positive fourth are added Amine, 15.5g (0.02mol) intermediate compound IV a is dissolved in 50ml ethanol, 2h is slowly added dropwise under 10 DEG C of ice-water baths, afterwards Recover normal temperature, react 2h, after reaction terminates, extracted, washed with 300ml ethyl acetate, concentrated, dried, obtain 14.4g fluothane Base aminated compounds Va, yield 95%.
Step 4 example 2, the reaction of the example are as shown in Equation 14：
Formula 14：
The operating process of the reaction is：In 250ml there-necked flask, 50ml ethanol, 2.7g (0.06mol) second are added Amine, 15.5g (0.02mol) intermediate compound IV a is dissolved in 50ml ethanol, 2h is slowly added dropwise under 10 DEG C of ice-water baths, afterwards Recover normal temperature, react 2h, after reaction terminates, extracted, washed with 300ml ethyl acetate, concentrated, dried, obtain 12.7g fluothane Base aminated compounds Vb, yield 90%.
Step 4 example 3, the reaction of the example are as shown in Equation 15：
Formula 15：
The operating process of the reaction is：In the reaction under high pressure bottle of 200ml specifications, 19.2g (0.02mol) centre is added Body IVb, 100ml methanol, are put into autoclave, are passed through 10.2g (0.6mol) ammonia, and 4h is reacted under the conditions of 60 DEG C, reaction After, 200ml ethyl acetate is added, is extracted, washing, liquid separation, is dried, is concentrated to give 12.2g fluoroalkyl aminated compounds Vc, yield 94%.
Step 4 example 4, the reaction of the example are as shown in Equation 16：
Formula 16：
The operating process of the reaction is：In 250ml there-necked flask, 17.2g (0.02mol) intermediate compound IV c is added, 100ml ammoniacal liquor installs reflux, flow back 8h, liquid separation after completion of the reaction, ethyl acetate dissolving, water as solvent and reactant Wash, liquid separation, dry, be concentrated to give 10g fluoroalkyl aminated compounds Vd, yield 92%.
In above-mentioned molecular structural formula：A, it is 1~10 that b, c, n, which can use number range,；
Z1、Z2For hetero atom or difluoro methylene, wherein hetero atom is O, S or Se；
R substituent is hydrogen, methyl, ethyl, propyl group, normal-butyl, the tert-butyl group, sec-butyl, amyl group, cyclohexyl, hexyl, benzene The aryl that base, benzyl or phenyl ring are substituted by other substituents；
X1, X2It may be selected from following functional group：Halogen, hydroxyl, carboxyl, amino, nitro, aldehyde radical, acyl group, sulfonamide, sulphonyl The common functional groups such as halogen, phosphoamide.

Claims (2)

  1. A kind of 1. fluoroalkyl aminated compounds, it is characterised in that：The molecular structural formula of the fluoroalkyl aminated compounds V is：
    In formula, it is 1~10 that a, b, c, n, which can use number range,；
    Z1、Z2For hetero atom or difluoro methylene, wherein hetero atom is O, S or Se；
    R substituent is hydrogen, methyl, ethyl, propyl group, normal-butyl, the tert-butyl group, sec-butyl, amyl group, cyclohexyl, hexyl, phenyl, benzyl The aryl that base or phenyl ring are substituted by other substituents.
  2. 2. prepare the method for the fluoroalkyl aminated compounds described in claim 1, it is characterised in that：The step of this method, is as follows：
    Step 1: being reacted to obtain intermediate II by compound I, reaction equation is as follows：
    Course of reaction is will wait stoichiometric compound I, reducing agent and 2~10 times of stoichiometric solvents I, in certain temperature Under the conditions of after certain reaction time through extracting, concentrating or be recrystallized to give intermediate II, the solvent I be water, ether, One or more of mixtures in dichloromethane, dioxane, acetonitrile or tetrahydrofuran, temperature range are 25~150 DEG C, institute It is sodium sulfite to state reducing agent, and potassium sulfite, sodium borohydride or sodium dithionite, the reaction time is 2~12h；
    Step 2: being reacted to obtain intermediate III by intermediate II, reaction equation is as follows：
    Course of reaction is adding for that will wait stoichiometric intermediate II, halide reagent and 2~10 times of stoichiometric polar solvents Heat condition reacts to obtain intermediate III, and the halide reagent is bromine, iodine, chlorine or sulfonic acid chloride, polar solvent be acetonitrile, water, Acetic acid, sulfonic acid chloride, dimethyl sulfoxide (DMSO), N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, tetrahydrofuran, methanol or ethanol In one or more of mixtures, heating temperature range be 60~120 DEG C, post-reaction treatment for plus water stratification；
    Step 3: being reacted to obtain intermediate compound IV by intermediate III, reaction equation is as follows：
    Course of reaction for will wait stoichiometric intermediate III, allyl compound, diiodomethane or
    Ethylidene periodide class compound, radical initiator and 2~10 times of stoichiometric solvents II, it is anti-under the conditions of certain temperature Intermediate compound IV should be obtained, the functional group Y of the allyl compound is chlorine, bromine, iodine ,-OTs ,-OMs ,-OTfOr-OH, free radical Initiator is sodium dithionite, benzoyl peroxide, azodiisobutyronitrile, hydrogen peroxide, sodium hydrogensulfite or rongalite, solvent II is acetonitrile, water, N,N-dimethylformamide, dimethyl sulfoxide (DMSO), dichloromethane, chloroform, tetrahydrofuran, methanol or ethanol In one or more of mixtures, temperature range be 0~120 DEG C.
    Step 4: intermediate compound IV reacts to obtain fluoroalkyl aminated compounds V, reaction equation is as follows：
    Course of reaction be by etc. stoichiometric intermediate compound IV, the alkylamine containing R substituent and 2~10 times of stoichiometric solvents III, fluoroalkyl aminated compounds V is obtained by nucleophilic substitution under the conditions of certain temperature, the R substituent is hydrogen, first Base, ethyl, propyl group, normal-butyl, the tert-butyl group, sec-butyl, amyl group, cyclohexyl, hexyl, phenyl, benzyl or phenyl ring are substituted by other The aryl of base substitution, solvent III are acetonitrile, water, DMF, dimethyl sulfoxide (DMSO), dichloromethane, chloroform, four One or more of mixtures in hydrogen furans, methanol or ethanol, temperature range are 0~100 DEG C；
    In above-mentioned molecular structural formula：A, it is 1~10 that b, c, n, which can use number range,；
    Z1、Z2For hetero atom or difluoro methylene, wherein hetero atom is O, S or Se；
    R substituent is hydrogen, methyl, ethyl, propyl group, normal-butyl, the tert-butyl group, sec-butyl, amyl group, cyclohexyl, hexyl, phenyl, benzyl The aryl that base or phenyl ring are substituted by other substituents；
    X1, X2It may be selected from following functional group：Halogen, hydroxyl, carboxyl, amino, nitro, aldehyde radical, acyl group, sulfonamide, sulfonic acid halide, carbon The common functional groups such as acid amides.
CN201710762903.7A 2017-08-30 2017-08-30 A kind of fluoroalkyl aminated compounds and preparation method thereof Pending CN107556202A (en)

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Cited By (3)

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CN108863858A (en) * 2018-07-19 2018-11-23 常州市灵达化学品有限公司 Novel fluorine surfactant
CN110759805A (en) * 2018-07-26 2020-02-07 中国科学院上海有机化学研究所 Preparation method of fluoroalkyl iodide
RU2739762C1 (en) * 2020-06-26 2020-12-28 Федеральное государственное бюджетное учреждение науки Институт элементоорганических соединений им. А.Н. Несмеянова Российской академии наук (ИНЭОС РАН) Method of producing perfluoroalkyl iodides and bromides

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US5266650A (en) * 1990-10-11 1993-11-30 Minnesota Mining And Manufacturing Company Curing fluorocarbon elastomers

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US5266650A (en) * 1990-10-11 1993-11-30 Minnesota Mining And Manufacturing Company Curing fluorocarbon elastomers

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108863858A (en) * 2018-07-19 2018-11-23 常州市灵达化学品有限公司 Novel fluorine surfactant
CN110759805A (en) * 2018-07-26 2020-02-07 中国科学院上海有机化学研究所 Preparation method of fluoroalkyl iodide
CN110759805B (en) * 2018-07-26 2021-12-14 中国科学院上海有机化学研究所 Preparation method of fluoroalkyl iodide
RU2739762C1 (en) * 2020-06-26 2020-12-28 Федеральное государственное бюджетное учреждение науки Институт элементоорганических соединений им. А.Н. Несмеянова Российской академии наук (ИНЭОС РАН) Method of producing perfluoroalkyl iodides and bromides

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Application publication date: 20180109