CN116925141A - Synthesis and research of novel organophosphorus flame retardant - Google Patents

Synthesis and research of novel organophosphorus flame retardant Download PDF

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Publication number
CN116925141A
CN116925141A CN202210346974.XA CN202210346974A CN116925141A CN 116925141 A CN116925141 A CN 116925141A CN 202210346974 A CN202210346974 A CN 202210346974A CN 116925141 A CN116925141 A CN 116925141A
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reaction
flame retardant
series
diphenyl
phosphoryl
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胡朗希
丁浩宇
王智刚
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Shenzhen Youwei Technology Holding Co ltd
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Shenzhen Youwei Technology Holding Co ltd
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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
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5341—Organo-phosphine oxides or thioxides containing a P-P bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K21/00—Fireproofing materials
    • C09K21/06—Organic materials
    • C09K21/12—Organic materials containing phosphorus

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)

Abstract

The application relates to the field of fine chemical materials, in particular to a mild and efficient synthesis and application research of a novel phosphorus flame retardant. The phosphorus flame retardant is used as a halogen-free flame retardant, has the characteristics of good thermal stability and no generation of corrosive smoke, and has the advantages of durable effect, small dosage, high efficiency, wide application range and wide prospect in industrial application, thus attracting attention. The intermediate state generated by the reaction of substituted diphenyl phosphorus chloride and substituted diphenyl ethyl phosphite under the high temperature condition is subjected to Arbuzov rearrangement reaction to obtain a phosphate structure, and the phosphate structure is further oxidized to obtain a phosphoryl structure, wherein the phosphate structure and the phosphoryl structure can be used as excellent flame retardants.

Description

Synthesis and research of novel organophosphorus flame retardant
Technical Field
The application relates to the field of fine chemical flame retardant materials, in particular to synthesis and application of phosphorus esters and phosphorus acyl flame retardants. The process prepares the substituted diphenyl ethylene phosphite by substituting diphenyl phosphorus chloride, then the substituted diphenyl phosphorus chloride and the substituted diphenyl ethylene phosphite undergo Arbuzov rearrangement reaction under high temperature condition to generate phospholipid structure, and the phospholipid structure is further oxidized into phosphoryl structure. In the process of producing the photo initiator TPO, tetraphenyl phospholipids structure impurities are generated due to improper process control, and the product is applied to a paint formula, so that the initiation efficiency of the initiator is not affected, and the paint is stronger in fire resistance, and proved to be a good flame retardant because of the tetraphenyl phospholipids structure, so that research is developed.
Background
The flame retardant mechanism of the phosphorus flame retardant mainly comprises the formation of a separation film to achieve the flame retardant effect, and the manner of forming the separation film is 2.
(1) The thermal degradation product of the flame retardant is utilized to promote the rapid dehydration and carbonization of the polymer surface, thereby forming a carbonized layer. The simple substance carbon does not carry out evaporation combustion and decomposition combustion for generating flame, so the flame-retardant protective effect is achieved. The flame retarding effect of the phosphorus flame retardant on the oxygen-containing polymer is achieved in this way. The reason for this is that the final product obtained by thermal decomposition of the phosphorus-containing compound is polymetaphosphoric acid, which is a strong dehydrating agent.
(2) The phosphorus flame retardant is decomposed at the burning temperature to form non-volatile glass-like substances, the non-volatile glass-like substances are coated on the surface of the polymer, and the compact protective layer plays a role of an isolating layer.
(3) Flame retardant type: the common phosphorus flame retardant phosphine oxide is a very stable organic phosphorus compound, can be used as a flame retardant of polyester, and the obtained flame retardant polyester has good color and luster and good mechanical property, and is continuously developed into new varieties in recent years. Flame retardant polyesters, polycarbonates, epoxy resins, polyurethanes, and the like can be made by blending and copolymerizing phosphine oxide monomers containing reactive functional groups. Phosphine oxide is an effective flame retardant for polyphenylene oxide, which is comparable to phosphate flame retardants, and because of the high phosphorus content, the amount of flame retardant to be added is small when the same flame retardant level is achieved. The main species are n-butylbis (hydroxypropyl) phosphine oxide (FR-D), trishydroxypropyl phosphine oxide (FR-T), cyclooctylhydroxypropyl phosphine oxide (CODPPO), p-bis (22 cyanoethyl phosphinomethyl) tetramethyl benzene (RF 2699). The phosphorus-containing monomers are bonded to the molecules of the synthetic material by a reaction that imparts permanent flame retardancy to the material. For example: the bis (p-carboxyphenyl) phenylphosphine oxide is used as a reactive flame retardant or flame retardant monomer for various polymers such as polyamide, polyester, polybenzimidazole and the like, and can simultaneously endow the polymer with better flame retardance, antistatic property, dyeing property, higher thermal and oxygen stability, higher glass transition temperature and the like. The phosphate series is the main series of flame retardants, and they are mostly additive flame retardants. The phosphate has rich resources, low price and good compatibility with high polymers, so that the phosphate has the most wide application in the organophosphorus flame retardant. The phosphate is prepared by reacting corresponding alcohol or phenol with phosphorus oxychloride, or by reacting corresponding alcohol or phenol with phosphorus trichloride and then chloridizing and hydrolyzing. Typical varieties thereof are triphenyl phosphate, tricresyl phosphate, tris (dibromopropyl) phosphate, tris (beta-chloroethyl) phosphate, and the like. The phosphate esters are characterized by having dual functions of flame retardance and plasticization. It can realize no halogenation of the flame retardant. The plasticizing function can improve the flow processability of the plastic during molding and can suppress the residue after combustion. The toxic gas and corrosive gas generated are less than halogen flame retardant.
The halogen-containing phosphate contains two elements, namely halogen and phosphorus, so that the flame retardant plays a role in the same gas phase and condensation, and has ideal flame retardant effect.
Disclosure of Invention
The application finds that the substituted diphenyl phosphorus chloride is used as an initial raw material to prepare the substituted diphenyl ethyl phosphite, then the substituted diphenyl phosphorus chloride reacts with the substituted diphenyl phosphorus chloride under a certain condition to generate a series of phospholipid structures, and a series of phosphoryl structures are obtained through oxidation, so that the substituted diphenyl phosphorus chloride is an excellent flame retardant. The main reactions are as follows:
in the above equation, R 1 ，R 2 Each independently is a compound having 1 to 8 carbon atoms (hereinafter referred to as C 1 -C 8 ) The linear or branched alkyl groups of (a) may be 1 to 6 non-continuous oxygen atoms, nitrogen atoms, sulfur atoms, halogen atoms, double bonds, triple bonds; r is R 1 ，R 2 May be ortho, meta or para to the benzene ring.
Conditions refer to any one of Conditions such as alkali, catalyst, heat, vacuum or pressure, solvent, or a combination of any two or more of the above, and are not specificAre not limited. The organic base is a fatty or aromatic tertiary amine type compound including tertiary amines containing a c=n double bond; the inorganic base is an alkali metal, alkaline earth metal, or transition metal hydroxide, oxide, sulfide, carbonate, carboxylate, or sulfonate; the catalyst or promoter refers to a lewis acid or basic compound. The reaction temperature is 80-400 degrees celsius, preferably 100-300 degrees celsius, more preferably 120-180 degrees celsius. The reaction pressure may be 0.001 to 50 atmospheres, preferably 0.01 to 20 atmospheres, more preferably 0.05 to 10 atmospheres. The solvent can be aromatic or aliphatic hydrocarbon, halogenated aromatic or aliphatic hydrocarbon, or various esters, ethers, nitriles, ketones, amides, sulfones, carbonates; or a mixed solvent system of any two or more of the above. The use of a solvent is preferred but not required, and under certain conditions, the reaction raw materials may be directly mixed and then reacted under heating or a gas phase condition without using a solvent. The oxidant can be oxygen, ozone, halogen, hydrogen peroxide, potassium permanganate, potassium dichromate, potassium chlorate, hypochlorous acid, and p-chloroperoxybenzoic acid; preferentially selecting oxygen, ozone, hydrogen peroxide and halogen; more preferably oxygen and hydrogen peroxide. The feeding mode adopts dripping and heating up adopts stage heating up. The series of phospholipid compounds are prepared from the following series of substituted diphenyl phosphorus chloride and substituted diphenyl ethyl phosphite under proper conditionsCFurther preparing a series of phosphoryl compoundsD；
An exemplary synthesis is the preparation of the corresponding product from diphenyl phosphorus chloride and diphenyl ethyl phosphite. Diphenyl phosphorus chloride is used as raw material, and the following reaction is carried out to synthesize the phospholipid and phosphoryl flame retardant. The process has the advantages of easily obtained raw materials, low cost, environment friendliness, safe process and high yield, and the generated product can be matched with the photo-initiator TPO to effectively reduce yellowing, greatly improve the fire resistance of the coating, and has the advantages of larger research and development of methyl ester and outstanding economic competitive advantage.
Exemplary, but non-limiting, compounds of the phosphorus esters and phosphoryl type that can be prepared via the disclosed techniques are, for example, the following structures:
we will further describe in the examples.
[ description of the drawings ]
The specification and the drawings contain phospholipid compounds with structures shown in the following figures 1 An H spectrum of the sample, 13 c-spectrum and P-spectrum. Wherein figure 1 is the compound 1 H spectrum, FIG. 2 shows the compound 13 Spectrum C and figure 3 shows the P spectrum of this compound.
[ detailed description ] of the application
The gist of the present application is further described below with reference to specific examples:
embodiment one:
under the protection of nitrogen, 22 g of diphenyl phosphorus chloride and 150 ml of toluene are added into a reaction bottle, the temperature is raised to 140 ℃, 25g of diphenyl ethyl phosphite and 50 ml of toluene are mixed, slowly added into the reaction bottle in a dropwise manner, the reaction is carried out while dropwise, the temperature is raised to 150 ℃ after the addition, the heat preservation is continued for 2 hours, the liquid phase is used for detecting that the diphenyl phosphorus chloride is completely reacted, and the reaction is stopped. The reaction solution was cooled to 50℃or less, and then poured into 100 ml of water to quench the reaction, followed by phase separation, alkali washing, water washing, desolventizing, and crystallization with 70% ethanol to obtain 35.1g of a white solid, with a yield of 90.6% and a purity of 98.8%. 1 H MNR（CDCl 3 400，HMz），δH：7.34-7.43（m，8H，），7.45-7.49（m，4H），7.70-7.75（m，4H），7.90-7.94（m，4H）。
The reaction liquid is not desolventized, 15g of 28% hydrogen peroxide is directly and slowly added into the reaction liquid, stirring is continued for 30 minutes after the addition, the liquid phase detection reaction is complete, the reaction is ended, phase separation, water washing, sodium hydrosulfite solution washing, organic phase concentration and 70% ethanol crystallization are carried out, and 35.8g of white solid is obtained, the yield is 89%, and the purity is 99.1%.
Embodiment two:
under the protection of nitrogen, 25g of diphenyl phosphorus chloride and 150 ml of toluene are added into a reaction bottle, the temperature is raised to 140 ℃, 25g of diphenyl ethyl phosphite and 50 ml of toluene are mixed and slowly added into the reaction bottle in a dropwise manner, the reaction is carried out while dropwise, the temperature is raised to 150 ℃ after the addition, the heat preservation is continued for 2 hours, the liquid phase is used for detecting that the diphenyl phosphorus chloride is completely reacted, and the reaction is stopped. The reaction solution was cooled to 50℃or less, and then poured into 100 ml of water to quench the reaction, followed by phase separation, alkali washing, water washing, desolventizing, and crystallization with 70% ethanol to obtain 37.9g of a white solid, yield 91.5% and purity 99.0%.
The reaction liquid is not desolventized, 15g of 28% hydrogen peroxide is directly and slowly added into the reaction liquid, stirring is continued for 30 minutes after the addition, the liquid phase detection reaction is complete, the reaction is ended, phase separation, water washing, sodium hydrosulfite solution washing, organic phase concentration and 70% ethanol crystallization are carried out, and 39.2g of white solid is obtained, the yield is 91.1%, and the purity is 99.2%.
Embodiment III:
under the protection of nitrogen, 25.5 g of diphenyl phosphorus chloride and 150 ml of toluene are added into a reaction bottle, the temperature is raised to 140 ℃, 25g of diphenyl ethyl phosphite and 50 ml of toluene are mixed, slowly added into the reaction bottle in a dropwise manner, the reaction is carried out while dropwise, the temperature is raised to 150 ℃ after the addition, the heat preservation is continued for 2 hours, the liquid phase is used for detecting that the diphenyl phosphorus chloride is completely reacted, and the reaction is stopped. The reaction solution was cooled to 50℃or less, and then poured into 100 ml of water to quench the reaction, followed by phase separation, alkali washing, water washing, desolventizing, and crystallization with 70% ethanol to obtain 34.1g of a white solid, 80.8% yield and 98.2% purity.
The reaction liquid is not desolventized, 15g of 28% hydrogen peroxide is directly and slowly added into the reaction liquid, stirring is continued for 30 minutes after the addition, the liquid phase detection reaction is complete, the reaction is ended, phase separation, water washing, sodium hydrosulfite solution washing, organic phase concentration and 70% ethanol crystallization are carried out, and 35.3g of white solid is obtained, the yield is 80.6%, and the purity is 99.0%.
Embodiment four:
under the protection of nitrogen, 29 g of diphenyl phosphorus chloride and 150 ml of toluene are added into a reaction bottle, the temperature is raised to 140 ℃, 25g of diphenyl ethyl phosphite and 50 ml of toluene are mixed, slowly added into the reaction bottle in a dropwise manner, the reaction is carried out while dropwise, the temperature is raised to 150 ℃ after the addition, the heat preservation is continued for 2 hours, the liquid phase is used for detecting that the diphenyl phosphorus chloride is completely reacted, and the reaction is stopped. The reaction solution was cooled to 50℃or less, and then poured into 100 ml of water to quench the reaction, followed by phase separation, alkali washing, water washing, desolventizing, and crystallization with 70% ethanol to obtain 35.1g of a white solid, yield 77.1% and purity 98.5%.
The reaction liquid is not desolventized, 15g of 28% hydrogen peroxide is directly and slowly added into the reaction liquid, stirring is continued for 30 minutes after the addition, the liquid phase detection reaction is complete, the reaction is ended, phase separation, water washing, sodium hydrosulfite solution washing, organic phase concentration and 70% ethanol crystallization are carried out, and 36.2g of white solid is obtained, the yield is 76.8%, and the purity is 98.8%.
Fifth embodiment:
under the protection of nitrogen, 29 g of diphenyl phosphorus chloride and 150 ml of toluene are added into a reaction bottle, the temperature is raised to 140 ℃, 25g of diphenyl ethyl phosphite and 50 ml of toluene are mixed, slowly added into the reaction bottle in a dropwise manner, the reaction is carried out while dropwise, the temperature is raised to 150 ℃ after the addition, the heat preservation is continued for 2 hours, the liquid phase is used for detecting that the diphenyl phosphorus chloride is completely reacted, and the reaction is stopped. The reaction solution was cooled to 50℃or less, and then poured into 100 ml of water to quench the reaction, followed by phase separation, alkali washing, water washing, desolventizing, and crystallization with 70% ethanol to obtain 35.1g of a white solid, yield 77.1% and purity 98.5%.
The reaction liquid is not desolventized, 15g of 28% hydrogen peroxide is directly and slowly added into the reaction liquid, stirring is continued for 30 minutes after the addition, the liquid phase detection reaction is complete, the reaction is ended, phase separation, water washing, sodium hydrosulfite solution washing, organic phase concentration and 70% ethanol crystallization are carried out, and 36.2g of white solid is obtained, the yield is 76.8%, and the purity is 98.8%.
Example six:
under the protection of nitrogen, 27 g of diphenyl phosphorus chloride and 150 ml of toluene are added into a reaction bottle, the temperature is raised to 140 ℃, 25g of diphenyl ethyl phosphite and 50 ml of toluene are mixed and slowly added into the reaction bottle in a dropwise manner, the reaction is carried out while dropwise, the temperature is raised to 150 ℃ after the addition, the heat preservation is continued for 2 hours, the liquid phase is used for detecting that the diphenyl phosphorus chloride is completely reacted, and the reaction is stopped. The reaction solution was cooled to 50℃or less, and poured into 100 ml of water to quench the reaction, followed by phase separation, alkali washing, water washing, desolventizing, and crystallization with 70% ethanol to obtain 34.8g of a white solid, yield 79.8% and purity 98.7%.
The reaction liquid is not desolventized, 15g of 28% hydrogen peroxide is directly and slowly added into the reaction liquid, stirring is continued for 30 minutes after the addition, the liquid phase detection reaction is complete, the reaction is ended, phase separation, water washing, sodium hydrosulfite solution washing, organic phase concentration and 70% ethanol crystallization are carried out, and 35.7g of white solid is obtained, the yield is 79%, and the purity is 98.9%.
Embodiment seven:
under the protection of nitrogen, 25g of diphenyl phosphorus chloride and 150 ml of toluene are added into a reaction bottle, the temperature is raised to 140 ℃, 32g of diphenyl ethyl phosphite and 50 ml of toluene are mixed, slowly added into the reaction bottle in a dropwise manner, the reaction is carried out while dropwise, the temperature is raised to 150 ℃ after the addition, the heat preservation is continued for 2 hours, the liquid phase is used for detecting that the diphenyl phosphorus chloride is completely reacted, and the reaction is stopped. The reaction solution was cooled to 50℃or less, poured into 100 ml of water to quench the reaction, and subjected to phase separation, alkali washing, water washing, desolventizing, and 70% ethanol crystallization to obtain 45.2g of a white solid, 95.4% yield and 99.4% purity.
The reaction liquid is not desolventized, 15g of 28% hydrogen peroxide is directly and slowly added into the reaction liquid, stirring is continued for 30 minutes after the addition, the liquid phase detection reaction is complete, the reaction is ended, phase separation, water washing, sodium hydrosulfite solution washing, organic phase concentration and 70% ethanol crystallization are carried out, and 46.3g of white solid is obtained, the yield is 94.5%, and the purity is 99.3%.
It should be emphasized that the above examples are merely illustrative and not limiting, and that any adjustments or variations in reaction conditions or parameters, etc. that may be commonly employed by practitioners based on the disclosure of this application, should not depart from the gist of the present application, and that the scope of this patent shall be subject to the relevant claim recitations.

Claims (10)

1. Reaction technology described by equation, structural formulaAThe shown disubstituted phenyl phosphorus chloride raw material and structural formulaBThe shown disubstituted ethyl phenylphosphite can be used for preparing a series of structural formulas under the action of proper ConditionsCThe target product is shown as a product of the reaction,Coxidized under proper conditions to obtain a series ofDThe target product is shown;CandDthe target products can be used as a novel flame retardant;
in the above equation, R 1 ，R 2 Each independently is a compound having 1 to 8 carbon atoms (hereinafter referred to as C 1 -C 8 ) Straight or branched chain of (2)An alkyl group which may be 1 to 6 non-consecutive oxygen atoms, nitrogen atoms, sulfur atoms, halogen atoms, double bonds, triple bonds; r is R 1 ，R 2 Can be ortho, meta or para to the benzene ring;
conditions refer to any one of Conditions such as alkali, catalyst, heat, vacuum or pressure, solvent, etc., or a combination of any two or more of the above, and are not particularly limited.
2. The process as described in claim (1), wherein the organic base is a tertiary aliphatic or aromatic amine compound comprising a tertiary amine containing a c=n double bond; the inorganic base is an alkali metal, alkaline earth metal, or transition metal hydroxide, oxide, sulfide, carbonate, carboxylate, or sulfonate; the catalyst or promoter refers to a lewis acid or basic compound.
3. The process as described in claim (1), wherein the reaction temperature is 80-400 degrees celsius, preferably 100-300 degrees celsius, more preferably 120-180 degrees celsius.
4. The process as described in claim (1), wherein the reaction pressure is 0.001 to 50 atm, preferably 0.01 to 20 atm, more preferably 0.05 to 10 atm.
5. The process according to claim (1), wherein the solvent is aromatic or aliphatic hydrocarbon, halogenated aromatic or aliphatic hydrocarbon, or various esters, ethers, nitriles, ketones, amides, sulfones, carbonates; or a mixed solvent system of any two or more of the above; the use of a solvent is preferred but not required, and under certain conditions, the reaction raw materials may be directly mixed and then reacted under heating or a gas phase condition without using a solvent.
6. The process as described in claim (1), wherein the oxidizing agent is oxygen, ozone, halogen, hydrogen peroxide, potassium permanganate, potassium dichromate, potassium chlorate, hypochlorous acid, p-chloroperoxybenzoic acid; preferentially selecting oxygen, ozone, hydrogen peroxide and halogen; more preferably oxygen and hydrogen peroxide.
7. According to the process described in the claim (1), the feeding mode adopts dripping and the heating adopts stage heating.
8. According to the process described in claim (1), the series of phospholipids is prepared from the following series of substituted diphenyl phosphorus chloride and substituted diphenyl ethyl phosphite under proper conditionsCFurther preparing a series of phosphoryl compoundsD；
。
9. According to the process described in claim (1), tetraphenyl and phospholipids are prepared from diphenyl phosphorus chloride and diphenyl ethyl phosphite under suitable conditions, and tetraphenyl phosphoryl is further prepared;
。
10. according to the process described in claim (1), the following phospholipids are prepared, and further phosphoryl compounds are prepared:
。
CN202210346974.XA 2022-04-01 2022-04-01 Synthesis and research of novel organophosphorus flame retardant Pending CN116925141A (en)

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