CN110372745B - Preparation method of flame-retardant compound - Google Patents

Preparation method of flame-retardant compound Download PDF

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CN110372745B
CN110372745B CN201910724650.3A CN201910724650A CN110372745B CN 110372745 B CN110372745 B CN 110372745B CN 201910724650 A CN201910724650 A CN 201910724650A CN 110372745 B CN110372745 B CN 110372745B
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杨旭锋
刘亭亭
于探来
武国兴
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Luliang University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4075—Esters with hydroxyalkyl compounds
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C08K5/5333—Esters of phosphonic acids
    • C08K5/5353—Esters of phosphonic acids containing also nitrogen
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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    • C08L2201/02—Flame or fire retardant/resistant
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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    • C08L2201/22—Halogen free composition

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Abstract

The invention provides a flame retardant compound and a preparation method and application thereof, belonging to the technical field of flame retardants. The flame-retardant compound provided by the invention has the structure shown in formula 1, is a brand-new flame-retardant variety, has good compatibility with a high-molecular material, is a high-efficiency halogen-free intumescent flame retardant, has excellent flame retardant performance, and can enable the oxygen index of a PVC material to reach 29.5% and the vertical burning UL94 to reach V0 level when the addition amount is 10%. The preparation method provided by the invention has the advantages of low cost and high yield, and can realize industrial production. The invention also provides application of the flame-retardant compound in the flame-retardant field.

Description

Preparation method of flame-retardant compound
Technical Field
The invention relates to the technical field of flame retardants, in particular to a flame retardant compound and a preparation method thereof.
Background
The phosphonate flame retardant is an important variety of phosphorus flame retardants, has the advantages of small addition amount, good compatibility with high polymer materials, small influence on the mechanical properties of the materials after flame retardant modification and the like, and is a green flame retardant with wide application prospect. In addition, the structure of the flame retardant is rich in P-C bonds, and the flame retardant is not easy to hydrolyze, so that the flame retardant has high thermal stability and hydrolytic stability, and is widely applied to flame retardant modification of high polymer materials such as polyurethane soft foam, epoxy resin and the like. Provides more new flame retardants and plays a great promoting role in the development of the flame retardants.
Disclosure of Invention
The invention aims to provide a novel flame-retardant compound, a preparation method and application thereof.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a flame retardant compound, which has a structure shown in a formula 1:
Figure GDA0003191633670000011
the invention provides a preparation method of the flame retardant compound in the scheme, which comprises the following steps:
carrying out Arbuzov reaction on 4 ', 4' -trihalotriphenylamine and trimethyl phosphite to obtain a flame-retardant compound with a structure shown in a formula 1;
Figure GDA0003191633670000021
preferably, the molar ratio of 4 ', 4 ", 4'" -trihalotriphenylamine to trimethyl phosphite is 1: (40-60).
Preferably, the 4 ', 4 ", 4'" -trihalotriphenylamine is 4 ', 4 ", 4'" -triiodotriphenylamine or 4 ', 4 ", 4'" -tribromotriphenylamine.
Preferably, the temperature of the Arbuzov reaction is 145-155 ℃.
Preferably, the Arbuzov reaction time is 4-6 h.
Preferably, the Arbuzov reaction is carried out under the condition of a catalyst, and the catalyst is palladium chloride, bis (triphenylphosphine) palladium dichloride, palladium acetate or anhydrous nickel chloride.
Preferably, the molar ratio of the 4 ', 4' -trihalotriphenylamine to the catalyst is 1 (0.15-0.30).
Preferably, the Arbuzov reaction is carried out in the presence of an inert gas.
The invention provides application of the flame-retardant compound in the scheme in the flame-retardant field.
The invention provides a flame retardant compound, which has a structure shown in a formula 1:
Figure GDA0003191633670000022
the flame-retardant compound is a brand-new flame-retardant variety, has good compatibility with high polymer materials, is an efficient halogen-free intumescent flame retardant, and has excellent flame retardant property. When the addition amount of the flame retardant compound is 10%, the oxygen index of the PVC material can reach 29.5%, and the vertical burning UL94 reaches the V0 level.
The preparation method of the flame-retardant compound provided by the invention has the advantages of low cost and high yield, and can realize industrial production.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of example 1.
Detailed Description
The invention provides a flame retardant compound, which has a structure shown in a formula 1:
Figure GDA0003191633670000031
according to the IUPAC nomenclature convention, the name of the compound having the structure shown in formula 1 is: 4 ', 4 ", 4'" -methyl triphosphonate triphenylamine.
The invention provides a preparation method of the flame retardant compound in the scheme, which comprises the following steps:
arbuzov reaction of 4 ', 4 ", 4' -trihalotriphenylamine with trimethyl phosphite gave a compound having
A flame retardant compound having a structure represented by formula 1;
Figure GDA0003191633670000032
in the present invention, the molar ratio of 4 ', 4 ", 4'" -trihalotriphenylamine to trimethyl phosphite is preferably 1: (40-60), and more preferably 1: 50. In the present invention, the 4 ', 4 ", 4'" -trihalotriphenylamine is preferably 4 ', 4 ", 4'" -triiodotriphenylamine or 4 ', 4 ", 4'" -tribromotriphenylamine, and since 4 ', 4 ", 4'" -tribromotriphenylamine has a greater reaction difficulty than 4 ', 4 ", 4'" -triiodotriphenylamine, 4 ', 4 ", 4'" -triiodotriphenylamine is more preferably used in the present invention.
In the present invention, the structure of the 4 ', 4 ", 4'" -triiodotriphenylamine is shown as formula 2:
Figure GDA0003191633670000041
the source of the 4 ', 4 ", 4'" -trihalotriphenylamine of the present invention is not particularly limited and may be commercially available or prepared by itself, as is well known to those skilled in the art. The invention is preferably prepared by self to reduce the production cost. When prepared by itself, the 4 ', 4 ", 4'" -triiodotriphenylamine is preferably prepared according to the method disclosed in the Chemistry of materials,2005,17(11): 3031-: sequentially adding triphenylamine, potassium iodide and acetic acid into a three-neck flask provided with a spherical condenser and a stirrer, heating to 115-125 ℃ for refluxing, then adding potassium iodate into a reaction bottle in batches, reacting at a constant temperature for 3-5 h, changing the reaction liquid from colorless to brown, finally changing the reaction liquid into colorless, stopping heating, cooling to room temperature, rotationally evaporating to remove acetic acid, adding a saturated sodium thiosulfate solution and dichloromethane for extraction, drying an organic phase with anhydrous sodium sulfate, concentrating to obtain a light yellow solid, and recrystallizing ethyl acetate to obtain light yellow sheet crystals, namely 4 ', 4' -triiodo triphenylamine. The specific amounts of the respective substances are referred to the above-mentioned documents and are not described in detail here.
In the invention, the temperature of the Arbuzov reaction is preferably 145-155 ℃, and more preferably 150 ℃; the Arbuzov reaction time is preferably 4-6 h, and more preferably 5 h.
In the present invention, the Arbuzov reaction is preferably carried out under catalytic conditions.
In the present invention, the catalyst is preferably palladium chloride, bis (triphenylphosphine) palladium dichloride, palladium acetate or anhydrous nickel chloride, and is more preferably bis (triphenylphosphine) palladium dichloride. The source of the catalyst is not particularly limited in the present invention, and it can be prepared by commercially available methods well known in the art or by methods well known in the art. When the catalyst is bis triphenylphosphine palladium dichloride, the catalyst is preferably prepared by a method known in the art so as to reduce the production cost. In the invention, the mole ratio of the 4 ', 4' -trihalotriphenylamine to the catalyst is preferably 1 (0.15-0.30).
In the present invention, the Arbuzov reaction is preferably carried out in the presence of an inert gas. The invention has no special requirement on the type of the inert gas, and the inert gas known to a person skilled in the art can be adopted, specifically, nitrogen, argon and the like can be adopted, and nitrogen is preferred for saving the cost.
In the present invention, the Arbuzov reaction is preferably carried out under stirring conditions. The stirring speed of the invention has no special requirement, and the stirring speed which is conventional in the field can be adopted.
After the Arbuzov reaction, the invention preferably further comprises cooling the reaction product system to room temperature, and separating the reaction product system to obtain the flame retardant compound with the structure shown in formula 1. In the present invention, the separation preferably comprises the steps of: and filtering the catalyst, removing redundant trimethyl phosphite by rotary evaporation to obtain light yellow viscous liquid, and performing column chromatography separation on the light yellow viscous liquid to obtain the flame-retardant compound with the structure shown in the formula 1.
The invention provides application of the flame-retardant compound in the scheme in the flame-retardant field. The invention has no special requirements for the mode of application, and can be applied by the mode of application well known in the field.
The flame retardant compounds provided by the present invention, and the preparation method and application thereof, will be described in detail with reference to the following examples, which should not be construed as limiting the scope of the present invention.
The raw materials used in examples 1 to 5 are shown in Table 1.
TABLE 1 summary of the sources of the raw materials used in the examples
Figure GDA0003191633670000051
Example 1
Preparation of 4 ', 4 ", 4'" -Triiodotriphenylamine (Compound of formula 2)
Adding triphenylamine 2.45g, potassium iodide 3.65g and acetic acid 100mL into a 250mL three-neck flask provided with a spherical condenser and a stirrer in sequence, heating to reflux, then adding 2.35g of potassium iodate into a reaction bottle in 6 batches, adding about 0.6g into each batch, reacting at constant temperature for 4h, changing the reaction liquid from colorless to brown, finally changing the reaction liquid to colorless, stopping heating, cooling to room temperature, removing acetic acid by spinning, adding 100mL of saturated sodium thiosulfate solution and 150mL of dichloromethane for extraction, drying an organic phase by using anhydrous sodium sulfate, concentrating to obtain a light yellow solid 6.11g, recrystallizing ethyl acetate to obtain 5.80g of light yellow plate crystals, and obtaining the yield of 93.00%. (Mp:169 ℃ C.)
Preparation of 4 ', 4 ", 4'" -Triphenyl methyl triphosphonate (Compound of formula 1)
In a 50mL three-necked flask equipped with a bulb-shaped condenser and a stirrer were placed 2g of 4 ', 4' -triiodotriphenylamine, 20mL of trimethyl phosphite and 0.34g of Pd (PPh) in this order3)2Cl2Reacting at constant temperature of 150 ℃ for 5h under nitrogen atmosphere, cooling to room temperature after the reaction is finished, filtering out the catalyst, removing redundant trimethyl phosphite by rotary evaporation to obtain 2g of light yellow viscous liquid, and performing column chromatography to obtain 1.47g of a target product with the yield of 81%. The nuclear magnetic hydrogen spectrum test of the obtained product is shown in figure 1, and the specific data are as follows:
1H NMR(DCCl3,δ,ppm):7.7(dd,6H,J＝7.62Hz),7.2(dd,6H,J＝16.86Hz),3.8(d,18H,J＝22.14Hz)；
the test result proves that the product is the flame-retardant compound with the structure shown in the formula 1.
Example 2
Preparation of 4 ', 4 ", 4'" -Triiodotriphenylamine (Compound of formula 2)
In a 250mL three-neck flask with a spherical condenser and a stirrer, 2.45g of triphenylamine, 3.65g of potassium iodide and 100mL of acetic acid are sequentially added, the mixture is heated to reflux, then 3.20g of potassium iodate is added into the reaction flask in batches, the reaction is carried out at constant temperature for 4h, the reaction liquid is firstly changed from colorless to brown and finally is changed into colorless, the heating is stopped, the reaction liquid is cooled to room temperature, the acetic acid is removed by spinning, saturated sodium thiosulfate solution and dichloromethane are added for extraction, the organic phase is dried by anhydrous sodium sulfate, the concentration is carried out to obtain 6.20g of light yellow solid, and ethyl acetate is recrystallized to obtain 5.85g of light yellow plate crystals, wherein the yield is 93.90%. (Mp:169 ℃ C.)
Preparation of 4 ', 4 ", 4'" -Triphenyl methyl triphosphonate (Compound of formula 1)
In a 50mL three-necked flask equipped with a bulb-shaped condenser and a stirrer were placed 2g of 4 ', 4' -triiodotriphenylamine, 20mL of trimethyl phosphite and 0.17g of PdCl in this order2Reacting at constant temperature of 150 ℃ for 4h under nitrogen atmosphere, cooling to room temperature after the reaction is finished, filtering out the catalyst, removing redundant trimethyl phosphite by rotary evaporation to obtain 1.93g of light yellow viscous liquid, and performing column chromatography to obtain 1.27g of a target product with the yield of 70%.
Example 3
Preparation of 4 ', 4 ", 4'" -Triiodotriphenylamine (Compound of formula 2)
Adding 4.90g of triphenylamine, 7.30g of potassium iodide and 200mL of acetic acid into a 500mL three-neck flask provided with a spherical condenser and a stirrer in sequence, heating to reflux, then adding 6.40g of potassium iodate into a reaction bottle in batches, reacting at constant temperature for 4h, changing the reaction liquid from colorless to brown, finally changing the reaction liquid to colorless, stopping heating, cooling to room temperature, removing the acetic acid by spinning, adding saturated sodium thiosulfate solution and dichloromethane for extraction, drying an organic phase by using anhydrous sodium sulfate, concentrating to obtain 12.50g of light yellow solid, and recrystallizing by using ethyl acetate to obtain 11.77g of light yellow plate crystals, wherein the yield is 94.50%. (Mp:169 ℃ C.)
Preparation of 4 ', 4 ", 4'" -Triphenyl methyl triphosphonate (Compound of formula 1)
In a 50mL three-necked flask equipped with a bulb-shaped condenser and a stirrer were placed 2.00g of 4 ', 4' -triiodotriphenylamine, 20mL of trimethyl phosphite and 0.12g of anhydrous NiCl in this order2Reacting at constant temperature of 150 ℃ for 5h in nitrogen atmosphere, cooling to room temperature after the reaction is finished, filtering out the catalyst, removing redundant trimethyl phosphite by rotary evaporation to obtain 2g of light yellow viscous liquid, and performing column chromatography to obtain 1.31g of a target product with the yield of 72%.
Example 4
Preparation of 4 ', 4 ", 4'" -Triiodotriphenylamine (Compound of formula 2)
In a 500mL three-neck flask equipped with a spherical condenser and a stirrer, 4.9g of triphenylamine, 6.63g of potassium iodide and 200mL of acetic acid are sequentially added, the mixture is heated to reflux, then 4.28g of potassium iodate is added into the reaction flask in batches, the reaction is carried out at constant temperature for 4h, the reaction liquid is firstly changed from colorless to brown and finally changed into colorless, the heating is stopped, the reaction liquid is cooled to room temperature, the acetic acid is removed by rotation, saturated sodium thiosulfate solution and dichloromethane are added for extraction, the organic phase is dried by anhydrous sodium sulfate, the concentration is carried out to obtain 10.21g of light yellow solid, and ethyl acetate is recrystallized to obtain 9.51g of light yellow plate crystals, wherein the yield is 76.32%. (Mp:169 ℃ C.)
Preparation of 4 ', 4 ", 4'" -Triphenyl methyl triphosphonate (Compound of formula 1)
In a 50mL three-necked flask equipped with a bulb condenser and a stirrer were placed 2.00g of 4 ', 4' -triiodotriphenylamine, 20mL of trimethyl phosphite and 0.13g of Pd (OAc) in this order2Reacting at constant temperature of 150 ℃ for 5h in nitrogen atmosphere, cooling to room temperature after the reaction is finished, filtering out the catalyst, removing redundant trimethyl phosphite by rotary evaporation to obtain 2.10g of light yellow viscous liquid, and performing column chromatography to obtain 1.42g of a target product with yield of 78%.
Example 5
Preparation of 4 ', 4 ", 4'" -Triiodotriphenylamine (Compound of formula 2)
In a 250mL three-neck flask with a spherical condenser and a stirrer, 3.0g of triphenylamine, 4.45g of potassium iodide and 200mL of acetic acid are sequentially added, the mixture is heated to reflux, then 2.82g of potassium iodate is added into the reaction flask in batches, the reaction is carried out at constant temperature for 4h, the reaction liquid is firstly changed from colorless to brown and finally changed into colorless, the heating is stopped, the reaction liquid is cooled to room temperature, the acetic acid is removed by spinning, saturated sodium thiosulfate solution and dichloromethane are added for extraction, the organic phase is dried by anhydrous sodium sulfate, the concentration is carried out to obtain 7.11g of light yellow solid, ethyl acetate is recrystallized to obtain 6.92g of light yellow plate crystals, and the yield is 91.00%. (Mp:169 ℃ C.)
Preparation of 4 ', 4 ", 4'" -Triphenyl methyl triphosphonate (Compound of formula 1)
In which the ball is arrangedA100 mL three-necked flask equipped with a condenser and a stirrer was charged with 4.0g of 4 ', 4' -triiodotriphenylamine, 30mL of trimethyl phosphite, and 0.68g of Pd (PPh) in this order3)2Cl2Reacting at constant temperature of 150 ℃ for 5h in nitrogen atmosphere, cooling to room temperature after the reaction is finished, filtering out the catalyst, removing redundant trimethyl phosphite by rotary evaporation to obtain 4.2g of light yellow viscous liquid, and performing column chromatographic separation to obtain 3.02g of a target product with the yield of 83%.
The product of example 1 is used as a standard substance, and the TLC (thin layer chromatography) and the product of example 1 are adopted for comparison verification in examples 2-5, so that the products of examples 2-5 are all the flame retardant compounds with the structure of formula 1.
The flame retardant compounds obtained in examples 1 to 5 were mixed, and subjected to a flame retardant property test, and the test results showed that: when the addition amount of the flame retardant compound is 10%, the oxygen index of the PVC material can reach 29.5%, and the vertical burning UL94 reaches the V0 level, which shows that the flame retardant compound provided by the invention has excellent flame retardant property.
The embodiments show that the invention provides a new flame retardant compound, which has good compatibility with high polymer materials, is an efficient halogen-free intumescent flame retardant and has excellent flame retardant performance.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.

Claims (6)

1. A method of preparing a flame retardant compound, comprising the steps of:
carrying out Arbuzov reaction on 4 ', 4' -trihalotriphenylamine and trimethyl phosphite to obtain a flame-retardant compound with a structure shown in a formula 1;
Figure FDA0003191633660000011
the temperature of the Arbuzov reaction is 145-155 ℃;
the Arbuzov reaction is carried out under the condition of a catalyst, and the catalyst is palladium chloride, bis (triphenylphosphine) palladium dichloride, palladium acetate or anhydrous nickel chloride.
2. The method of claim 1, wherein the molar ratio of 4 ', 4 ", 4'" -trihalotriphenylamine to trimethyl phosphite is 1: (40-60).
3. A method of preparation according to claim 1 or 2, wherein the 4 ', 4 ", 4'" -trihalotriphenylamine is 4 ', 4 ", 4'" -triiodotriphenylamine or 4 ', 4 ", 4'" -tribromotriphenylamine.
4. The preparation method according to claim 1, wherein the Arbuzov reaction time is 4-6 h.
5. The method according to claim 1, wherein the molar ratio of 4 ', 4 ", 4'" -trihalotriphenylamine to the catalyst is 1 (0.15-0.30).
6. The process according to claim 1, wherein the Arbuzov reaction is carried out in the presence of an inert gas.
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