CN113999260A - Alkyl diphenyl phosphate - Google Patents
Alkyl diphenyl phosphate Download PDFInfo
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- CN113999260A CN113999260A CN202110814275.9A CN202110814275A CN113999260A CN 113999260 A CN113999260 A CN 113999260A CN 202110814275 A CN202110814275 A CN 202110814275A CN 113999260 A CN113999260 A CN 113999260A
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- -1 Alkyl diphenyl phosphate Chemical compound 0.000 title claims abstract description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 56
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 51
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims abstract description 40
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000002994 raw material Substances 0.000 claims abstract description 40
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims abstract description 40
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 36
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 239000007788 liquid Substances 0.000 claims abstract description 29
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910052938 sodium sulfate Inorganic materials 0.000 claims abstract description 18
- 235000011152 sodium sulphate Nutrition 0.000 claims abstract description 18
- 235000011121 sodium hydroxide Nutrition 0.000 claims abstract description 17
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims abstract description 15
- 235000017550 sodium carbonate Nutrition 0.000 claims abstract description 15
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 15
- 230000005484 gravity Effects 0.000 claims abstract description 8
- 239000002244 precipitate Substances 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 18
- 238000004321 preservation Methods 0.000 claims description 16
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical class ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 9
- 150000002191 fatty alcohols Chemical class 0.000 claims description 9
- 238000005086 pumping Methods 0.000 claims description 9
- 238000005070 sampling Methods 0.000 claims description 9
- 241001550224 Apha Species 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 4
- 238000004458 analytical method Methods 0.000 claims description 4
- 238000003556 assay Methods 0.000 claims description 4
- 238000005303 weighing Methods 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 239000012267 brine Substances 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 238000007599 discharging Methods 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 239000005457 ice water Substances 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 238000003825 pressing Methods 0.000 claims description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- 229940127554 medical product Drugs 0.000 abstract description 9
- 238000004806 packaging method and process Methods 0.000 abstract description 9
- 231100000053 low toxicity Toxicity 0.000 abstract description 8
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract description 6
- 239000003063 flame retardant Substances 0.000 abstract description 6
- 239000004014 plasticizer Substances 0.000 abstract description 3
- 239000012774 insulation material Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- BYEVBITUADOIGY-UHFFFAOYSA-N ethyl nonanoate Chemical compound CCCCCCCCC(=O)OCC BYEVBITUADOIGY-UHFFFAOYSA-N 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical compound [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 1
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Classifications
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
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Abstract
The invention discloses alkyl diphenyl phosphate, and relates to the technical field of flame retardant plasticizers. The feed comprises the following raw materials in parts by weight: M-N parts of dichloronium salt; 6.5-7.8 parts of phenol, 7.5-9.5 parts of water, 11.2-12.6 parts of caustic soda liquid, 0.01-0.015 part of TEBA, 0.865-1.12 parts of anhydrous sodium sulphate and 0.865-1.12 parts of soda ash; half of the dichloride salt is prepared from the following raw materials: 10-12 parts of phosphorus oxychloride, 6.3-7.45 parts of dodecanol and 6.3-7.45 parts of tetradecanol. The alkyl diphenyl phosphate prepared by the invention is colorless and transparent liquid in appearance, has no suspended matters and precipitates, has the specific gravity of 1.028-1.044, the refractive index of 1.494-1.502 degrees, the water content of less than or equal to 0.1 percent, the acidity of less than or equal to 0.2 percent, the chroma of less than or equal to 50APHA, has low toxicity and can be used for food packaging and medical products.
Description
Technical Field
The invention belongs to the technical field of flame retardant plasticizers, and particularly relates to alkyl diphenyl phosphate.
Background
The molecular formula of the alkyl diphenyl phosphate is as follows: c24H35O4P。
The traditional heat insulation material is mainly an inorganic heat insulation material and an organic heat insulation material, the heat conductivity coefficient of the inorganic heat insulation material is larger, and the heat insulation effect is slightly poor; the heat conductivity coefficient of the organic heat-insulating material is lower, the heat-insulating effect is better, but the existing heat-insulating material has good fireproof performance and poor heat-insulating performance; good thermal insulation performance and poor flame retardant performance, and the two are difficult to meet simultaneously. At present, inorganic-organic composite materials become the focus of research at present, and the flame retardant property of the thermal insulation material is improved by adding alkyl diphenyl phosphate when preparing the thermal insulation material, for example, chinese patent CN107512925A discloses a cold-resistant thermal insulation material and a preparation method thereof, wherein alkyl diphenyl phosphate, ethyl nonanoate and the like are added, and the flame retardant property of the thermal insulation material is further optimized by drying, melt extrusion and granulation under specific conditions.
Alkyl diphenyl phosphate is colorless transparent liquid, is slightly soluble in hot water, is easily soluble in organic solvents such as alcohol, chloroform and the like, can be used as a flame retardant plasticizer, has low toxicity, can be used for food packaging and medical products, is mainly used for human bodies, is directly related to human life and health, and generally has the requirements on the performance: safety: for example, as disclosed in chinese patent CN104448677A, a medical antibacterial ABS material and a preparation method thereof are prepared by weighing ABS, alkyl diphenyl phosphate, nano zirconium phosphate silver-carrying antibacterial agent, magnesium hydroxide, etc. according to a weight ratio, mixing them uniformly, and extruding and granulating.
And the like, and alkyl diphenyl phosphoric acid is widely used in the fields of food packaging, medical products, and the like. Alkyl diphenyl phosphate and a preparation method thereof are provided for preparing the alkyl diphenyl phosphate.
Disclosure of Invention
The invention aims to provide alkyl diphenyl phosphate, which improves the yield and quality of the alkyl diphenyl phosphate by adjusting raw materials and the proportion thereof and optimizing the preparation process.
In order to solve the technical problems, the invention is realized by the following technical scheme:
the invention relates to alkyl diphenyl phosphate, which comprises the following raw materials in parts by weight:
and (2) component A: M-N parts of dichloronium salt;
and (B) component: 6.5-7.8 parts of phenol, 7.5-9.5 parts of water, 11.2-12.6 parts of caustic soda liquid, 0.01-0.015 part of TEBA, 0.865-1.12 parts of anhydrous sodium sulphate and 0.865-1.12 parts of soda ash;
half of the dichloride salt is prepared from the following raw materials in parts by weight: 10-12 parts of phosphorus oxychloride, 6.3-7.45 parts of dodecanol and 6.3-7.45 parts of tetradecanol.
Further, the alkyl diphenyl phosphate comprises the following raw materials in parts by weight:
and (2) component A: s parts of a dichlorohydrin salt; wherein M < S < N;
and (B) component: 7.3 parts of phenol, 9.1 parts of water, 12.04 parts of caustic soda liquid, 0.0112 part of TEBA, 1 part of anhydrous sodium sulphate and 1 part of soda ash;
half of the dichloride salt is prepared from the following raw materials in parts by weight: 11.5 parts of phosphorus oxychloride, 6.8 parts of dodecanol and 6.8 parts of tetradecanol.
Further, the alkyl diphenyl phosphate comprises the following raw materials in parts by weight:
and (2) component A: m parts of a dichlorohydrin salt;
and (B) component: 6.5 parts of phenol, 7.5 parts of water, 11.2 parts of caustic soda liquid, 0.01 part of TEBA, 0.865 part of anhydrous sodium sulphate and 0.865 part of calcined soda;
half of the dichloride salt is prepared from the following raw materials in parts by weight: 10 parts of phosphorus oxychloride, 6.3 parts of dodecanol and 6.3 parts of tetradecanol.
Further, the alkyl diphenyl phosphate comprises the following raw materials in parts by weight:
and (2) component A: n parts of dichlorohydrin;
and (B) component: 7.8 parts of phenol, 9.5 parts of water, 12.6 parts of caustic soda liquid, 0.015 part of TEBA, 1.12 parts of anhydrous sodium sulphate and 1.12 parts of sodium carbonate;
half of the dichloride salt is prepared from the following raw materials in parts by weight: 12 parts of phosphorus oxychloride, 7.45 parts of dodecanol and 7.45 parts of tetradecanol; the specification of each raw material is as follows:
further, the preparation method of the alkyl diphenyl phosphate comprises the following steps:
preparing alkyl diphenyl phosphate from the raw materials according to the parts by weight of any one of claims 1 to 4;
step S1: and (3) oxidation: preparing a dichloride salt by phosphorus oxychloride, dodecanol and tetradecanol;
step S2: condensation, distillation, filter pressing and mixed splicing:
step S21: putting water into a four-neck flask, starting a stirrer to stir, pumping molten phenol into a reaction kettle, stirring for 20-30 minutes, and pouring into a dropping funnel for later use after the molten phenol is completely liquefied;
step S22: pouring half of the amount of the dichloride salt prepared in the step S1 into a dropping funnel for standby;
step S23: pumping water and caustic soda liquid into a four-mouth flask, starting a stirrer to stir, cooling and stirring for 15-20 minutes, and sampling and analyzing when the material temperature is lower than 15 ℃;
step S24: after sampling and analyzing to be qualified, slowly dripping the phenol liquefied liquid, wherein the temperature is controlled to be 5-20 ℃ during dripping; after the phenol liquid is dripped, keeping the temperature for 2 hours;
step S25: after the heat preservation is finished, dropwise adding dichlorohydrin at the temperature of 0-15 ℃, wherein the dropwise adding time is 4-5 hours;
step S26: after the dichlorohydrin is dripped, the reaction is carried out for 1 hour under the condition of heat preservation at the temperature of 0-15 ℃, after the heat preservation is finished, the temperature is naturally raised to 25-30 ℃, and the reaction is carried out for 4 hours under the condition of heat preservation;
step S27: after the heat preservation reaction is finished, standing and layering for 5-6 hours, then removing a lower alkaline water layer, and pumping a material layer into a flask for dehydration;
step S28: in a flask, firstly heating to remove moisture in materials, then cooling, adding sodium carbonate and anhydrous sodium sulphate, stirring for 1 hour, and then carrying out suction filtration;
step S29: and (5) after the product is analyzed and tested to be qualified, obtaining a finished product.
Further, the specific preparation process of the dichloride salt is as follows:
step S11: pouring molten dodecanol and tetradecanol into a heat-preserving dropping funnel to prepare mixed fatty alcohol to be dropped;
step S12: putting phosphorus oxychloride into a dry and clean four-neck flask, starting a stirrer to stir, and simultaneously cooling by adopting brine ice;
step S13: when the temperature of the materials in the four-mouth flask is cooled to 45-60 ℃, slowly dripping the mixed fatty alcohol prepared in the step S11, simultaneously opening a valve of a tail gas absorption device, and controlling the dripping temperature to be 0-10 ℃;
step S14: after the mixed fatty alcohol is dripped, reacting for 2 hours at the temperature of 0-15 ℃, removing ice water, naturally heating to 20-25 ℃, and vacuumizing for 5-6 hours under reduced pressure at the temperature; step S15: after the hydrogen chloride gas is completely pulled out, discharging, weighing and recording, and dividing the produced dichlorinate into two parts for later use.
Further, the sampling analysis method in step S23 includes:
and (4) taking the product obtained in the step S23, and determining that the product is qualified when the alkali content of the product is 18-19%.
Further, the method for analyzing and testing in step S29 is as follows:
analyzing the water content of the material, and if the water content is more than 0.1%, dehydrating until the water content is less than or equal to 0.1%;
the water content is qualified, and the finished product is obtained after the water content is qualified through testing;
the qualified standard of the assay is:
appearance: colorless transparent liquid, no suspended matter and precipitate;
specific gravity: 1.028 to 1.044;
the folding rate is as follows: 1.494-1.502 degrees;
acidity: less than or equal to 0.2 percent;
chroma: less than or equal to 50 APHA.
Further, the water in the step S21 and the water in the step S23 are respectively in parts by weight:
water in step S21: 1.5-2 parts;
water in step S23: 6 to 7.5 portions.
Further, the chemical reaction process of the alkyl diphenyl phosphate ester is as follows:
the invention has the following beneficial effects:
the alkyl diphenyl phosphate prepared by the invention is colorless and transparent liquid in appearance, has no suspended matters and precipitates, has the specific gravity of 1.028-1.044, the refractive index of 1.494-1.502 degrees, and contains water: less than or equal to 0.1 percent, acidity: less than or equal to 0.2 percent, chroma: has APHA content of 50 or less and low toxicity, and can be used for food packaging and medical products.
Of course, it is not necessary for any product in which the invention is practiced to achieve all of the above-described advantages at the same time.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings used in the description of the embodiments will be briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art that other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a process flow diagram for preparing alkyl diphenyl phosphate according to the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The first embodiment is as follows:
the alkyl diphenyl phosphate comprises the following raw materials in parts by weight:
and (2) component A: M-N parts of dichloronium salt;
and (B) component: 6.5-7.8 parts of phenol, 7.5-9.5 parts of water, 11.2-12.6 parts of caustic soda liquid, 0.01-0.015 part of TEBA, 0.865-1.12 parts of anhydrous sodium sulphate and 0.865-1.12 parts of soda ash;
half of the dichloride salt is prepared from the following raw materials in parts by weight: 10-12 parts of phosphorus oxychloride, 6.3-7.45 parts of dodecanol and 6.3-7.45 parts of tetradecanol, and the alkyl diphenyl phosphate prepared by adopting the raw materials has low toxicity and can be used for food packaging and medical products.
Example two:
the alkyl diphenyl phosphate comprises the following raw materials in parts by weight:
and (2) component A: s parts of a dichlorohydrin salt; wherein M < S < N;
and (B) component: 7.3 parts of phenol, 9.1 parts of water, 12.04 parts of caustic soda liquid, 0.0112 part of TEBA, 1 part of anhydrous sodium sulphate and 1 part of soda ash;
half of the dichloride salt is prepared from the following raw materials in parts by weight: 11.5 parts of phosphorus oxychloride, 6.8 parts of dodecanol and 6.8 parts of tetradecanol, wherein the alkyl diphenyl phosphate prepared by adopting the raw materials in parts by weight and the preparation method of the alkyl diphenyl phosphate provided by the invention is colorless and transparent liquid without suspended matters and precipitates, has the specific gravity of 1.0369, the refractive index of 1.46 degrees, the moisture of 0.069 percent, the acidity of 0.168 percent and the chroma of 50 APHA.
Example three:
the alkyl diphenyl phosphate comprises the following raw materials in parts by weight:
and (2) component A: m parts of a dichlorohydrin salt;
and (B) component: 6.5 parts of phenol, 7.5 parts of water, 11.2 parts of caustic soda liquid, 0.01 part of TEBA, 0.865 part of anhydrous sodium sulphate and 0.865 part of calcined soda;
half of the dichloride salt is prepared from the following raw materials in parts by weight: 10 parts of phosphorus oxychloride, 6.3 parts of dodecanol and 6.3 parts of tetradecanol, wherein the specifications of the raw materials are as follows:
the alkyl diphenyl phosphate prepared by the raw materials in parts by weight and the preparation method of the alkyl diphenyl phosphate provided by the invention has the advantages of specific gravity of 1.0294, refractive index of 1.494 degrees, water content of 0.095 percent, acidity of 0.2 percent, chromaticity of 50APHA, low toxicity and suitability for food packaging and medical products.
Example four:
the alkyl diphenyl phosphate comprises the following raw materials in parts by weight:
and (2) component A: n parts of dichlorohydrin;
and (B) component: 7.8 parts of phenol, 9.5 parts of water, 12.6 parts of caustic soda liquid, 0.015 part of TEBA, 1.12 parts of anhydrous sodium sulphate and 1.12 parts of sodium carbonate;
half of the dichloride salt is prepared from the following raw materials in parts by weight: the alkyl diphenyl phosphate prepared by adopting the raw materials in parts by weight and the preparation method of the alkyl diphenyl phosphate provided by the invention has low toxicity, can be used for food packaging and medical products, and has the yield of 90.2%.
Example five:
the alkyl diphenyl phosphate comprises the following raw materials in parts by weight:
365g of phenol, 455g of water, 602g of caustic soda liquid, 0.56g of TEBA, 50g of anhydrous sodium sulphate and 50g of soda ash;
575g of phosphorus oxychloride, 340g of dodecanol and 340g of tetradecanol are adopted to prepare the dichloride salt, half of the dichloride salt is taken as a raw material, and the raw material in parts by weight and the alkyl diphenyl phosphate prepared by the preparation method of the alkyl diphenyl phosphate have low toxicity, can be used for food packaging and medical products, and has the yield of 89-90.2%.
Example six:
a preparation method of alkyl diphenyl phosphate comprises the following steps:
575g of phosphorus oxychloride, 340g of dodecanol and 340g of tetradecanol are adopted to prepare dichloride salt, and half of the dichloride salt, 365g of phenol, 455g of water, 602g of liquid alkali, 0.56g of TEBA, 50g of anhydrous sodium sulphate and 50g of sodium carbonate are taken as raw materials, and the raw materials in parts by weight are used for preparing alkyl diphenyl phosphate;
step S1: and (3) oxidation: preparing a dichloride salt by phosphorus oxychloride, dodecanol and tetradecanol;
step S2: condensation, distillation, filter pressing and mixed splicing:
step S21: putting 90g of water into a 2000ml four-neck flask, starting a stirrer to stir, pumping 365g of molten phenol into a reaction kettle, stirring for 20-30 minutes, and pouring into an 800ml dropping funnel for later use after the phenol is completely liquefied;
step S22: pouring half of the amount of the dichloride salt prepared in the step S1 into an 800ml dropping funnel for standby;
step S23: pumping 365g of water and 602g of liquid caustic soda into a 3000ml four-neck flask, starting a stirrer to stir, cooling and stirring for 15-20 minutes, and sampling and analyzing when the temperature of the material is lower than 15 ℃;
step S24: after sampling and analyzing to be qualified, slowly dripping the phenol liquefied liquid, wherein the temperature is controlled to be 5-20 ℃ during dripping; after the phenol liquid is dripped, keeping the temperature for 2 hours;
step S25: after the heat preservation is finished, dropwise adding dichlorohydrin at the temperature of 0-15 ℃, wherein the dropwise adding time is 4-5 hours;
step S26: after the dichlorohydrin is dripped, the reaction is carried out for 1 hour under the condition of heat preservation at the temperature of 0-15 ℃, after the heat preservation is finished, the temperature is naturally raised to 25-30 ℃, and the reaction is carried out for 4 hours under the condition of heat preservation;
step S27: after the heat preservation reaction is finished, standing and layering for 5-6 hours, then removing a lower alkaline water layer, and pumping a material layer into a flask for dehydration;
step S28: in a flask, firstly heating to remove moisture in the materials, then cooling, adding 60g of soda ash and 60g of anhydrous sodium sulphate, stirring for 1 hour, and then carrying out suction filtration;
step S29: after the product is analyzed and tested to be qualified, the finished product is obtained, and the yield of the alkyl diphenyl phosphate prepared by the method is up to 89.33%.
As an embodiment provided by the present invention, preferably, the water in step S21 and the water in step S23 are, by weight:
water in step S21: 1.5-2 parts;
water in step S23: 6 to 7.5 portions.
As an embodiment provided by the present invention, preferably, the sampling analysis method in step S23 includes:
and (4) taking the product obtained in the step S23, and determining that the product is qualified when the alkali content of the product is 18-19%.
As an embodiment provided by the present invention, preferably, the method for analyzing and assaying in step S29 includes:
analyzing the water content of the material, and if the water content is more than 0.1%, dehydrating until the water content is less than or equal to 0.1%;
the water content is qualified, and the finished product is obtained after the water content is qualified through testing;
the qualified standard of the assay is:
appearance: colorless transparent liquid, no suspended matter and precipitate;
specific gravity: 1.028 to 1.044;
the folding rate is as follows: 1.494-1.502 degrees;
acidity: less than or equal to 0.2 percent;
chroma: less than or equal to 50 APHA.
As an embodiment provided by the present invention, preferably, the chemical reaction process of the alkyl diphenyl phosphate ester is as follows:
example seven:
the specific preparation process of the dichloride salt is as follows:
step S11: pouring molten dodecanol and tetradecanol into a 1000ml heat-preservation dropping funnel to prepare mixed fatty alcohol to be dropped;
step S12: putting phosphorus oxychloride into a dry and clean 2000ml four-neck flask, starting a stirrer to stir, and simultaneously cooling by adopting brine ice;
step S13: when the temperature of the materials in the four-neck flask is cooled to 45-605 ℃ O, slowly dripping the mixed fatty alcohol prepared in the step S11, simultaneously opening a valve of a tail gas absorption device, and controlling the dripping temperature to be 0-10 ℃;
step S14: after the mixed fatty alcohol is dripped, reacting for 2 hours at the temperature of 0-15 ℃, removing ice water, naturally heating to 20-25 ℃, and vacuumizing for 5-6 hours under reduced pressure at the temperature; step S15: after the hydrogen chloride gas is completely pulled out, discharging, weighing and recording, and dividing the produced dichlorinate into two parts for later use.
The alkyl diphenyl phosphate prepared by the method is colorless transparent liquid in appearance, has no suspended matters and precipitates, has the specific gravity of 1.028-1.044, the refractive index of 1.494-1.502 degrees and contains water: less than or equal to 0.1 percent, acidity: less than or equal to 0.2 percent, chroma: has APHA content of 50 or less and low toxicity, and can be used for food packaging and medical products; the invention has simple production condition, higher yield and simple post-treatment process.
In the description herein, references to the description of "one embodiment," "an example," "a specific example" or the like are intended to mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The preferred embodiments of the invention disclosed above are intended to be illustrative only. The preferred embodiments are not intended to be exhaustive or to limit the invention to the precise embodiments disclosed. Obviously, many modifications and variations are possible in light of the above teaching. The embodiments were chosen and described in order to best explain the principles of the invention and the practical application, to thereby enable others skilled in the art to best utilize the invention. The invention is limited only by the claims and their full scope and equivalents.
Claims (10)
1. The alkyl diphenyl phosphate is characterized by comprising the following raw materials in parts by weight:
and (2) component A: M-N parts of dichloronium salt;
and (B) component: 6.5-7.8 parts of phenol, 7.5-9.5 parts of water, 11.2-12.6 parts of caustic soda liquid, 0.01-0.015 part of TEBA, 0.865-1.12 parts of anhydrous sodium sulphate and 0.865-1.12 parts of soda ash;
half of the dichloride salt is prepared from the following raw materials in parts by weight: 10-12 parts of phosphorus oxychloride, 6.3-7.45 parts of dodecanol and 6.3-7.45 parts of tetradecanol.
2. The alkyl diphenyl phosphate according to claim 1, wherein the alkyl diphenyl phosphate comprises the following raw materials in parts by weight:
and (2) component A: s parts of a dichlorohydrin salt; wherein M < S < N;
and (B) component: 7.3 parts of phenol, 9.1 parts of water, 12.04 parts of caustic soda liquid, 0.0112 part of TEBA, 1 part of anhydrous sodium sulphate and 1 part of soda ash;
half of the dichloride salt is prepared from the following raw materials in parts by weight: 11.5 parts of phosphorus oxychloride, 6.8 parts of dodecanol and 6.8 parts of tetradecanol.
3. The alkyl diphenyl phosphate according to claim 1, wherein the alkyl diphenyl phosphate comprises the following raw materials in parts by weight:
and (2) component A: m parts of a dichlorohydrin salt;
and (B) component: 6.5 parts of phenol, 7.5 parts of water, 11.2 parts of caustic soda liquid, 0.01 part of TEBA, 0.865 part of anhydrous sodium sulphate and 0.865 part of calcined soda;
half of the dichloride salt is prepared from the following raw materials in parts by weight: 10 parts of phosphorus oxychloride, 6.3 parts of dodecanol and 6.3 parts of tetradecanol.
4. The alkyl diphenyl phosphate according to claim 1, wherein the alkyl diphenyl phosphate comprises the following raw materials in parts by weight:
and (2) component A: n parts of dichlorohydrin;
and (B) component: 7.8 parts of phenol, 9.5 parts of water, 12.6 parts of caustic soda liquid, 0.015 part of TEBA, 1.12 parts of anhydrous sodium sulphate and 1.12 parts of sodium carbonate;
half of the dichloride salt is prepared from the following raw materials in parts by weight: 12 parts of phosphorus oxychloride, 7.45 parts of dodecanol and 7.45 parts of tetradecanol.
5. The alkyl diphenyl phosphate according to any one of claims 1 to 4, wherein the preparation method of the alkyl diphenyl phosphate comprises the following steps:
preparing alkyl diphenyl phosphate from the raw materials according to the parts by weight of any one of claims 1 to 4;
step S1: and (3) oxidation: preparing a dichloride salt by phosphorus oxychloride, dodecanol and tetradecanol;
step S2: condensation, distillation, filter pressing and mixed splicing:
step S21: putting water into a four-neck flask, starting a stirrer to stir, pumping molten phenol into a reaction kettle, stirring for 20-30 minutes, and pouring into a dropping funnel for later use after the molten phenol is completely liquefied;
step S22: pouring half of the amount of the dichloride salt prepared in the step S1 into a dropping funnel for standby;
step S23: pumping water and caustic soda liquid into a four-mouth flask, starting a stirrer to stir, cooling and stirring for 15-20 minutes, and sampling and analyzing when the material temperature is lower than 15 ℃;
step S24: after sampling and analyzing to be qualified, slowly dripping the phenol liquefied liquid, wherein the temperature is controlled to be 5-20 ℃ during dripping; after the phenol liquid is dripped, keeping the temperature for 2 hours;
step S25: after the heat preservation is finished, dropwise adding dichlorohydrin at the temperature of 0-15 ℃, wherein the dropwise adding time is 4-5 hours;
step S26: after the dichlorohydrin is dripped, the reaction is carried out for 1 hour under the condition of heat preservation at the temperature of 0-15 ℃, after the heat preservation is finished, the temperature is naturally raised to 25-30 ℃, and the reaction is carried out for 4 hours under the condition of heat preservation;
step S27: after the heat preservation reaction is finished, standing and layering for 5-6 hours, then removing a lower alkaline water layer, and pumping a material layer into a flask for dehydration;
step S28: in a flask, firstly heating to remove moisture in materials, then cooling, adding sodium carbonate and anhydrous sodium sulphate, stirring for 1 hour, and then carrying out suction filtration;
step S29: and (5) after the product is analyzed and tested to be qualified, obtaining a finished product.
6. The alkyl diphenyl phosphate as claimed in claim 5, wherein the specific preparation process of said dichloride salt is as follows:
step S11: pouring molten dodecanol and tetradecanol into a heat-preserving dropping funnel to prepare mixed fatty alcohol to be dropped;
step S12: putting phosphorus oxychloride into a dry and clean four-neck flask, starting a stirrer to stir, and simultaneously cooling by adopting brine ice;
step S13: when the temperature of the materials in the four-mouth flask is cooled to 45-60 ℃, slowly dripping the mixed fatty alcohol prepared in the step S11, simultaneously opening a valve of a tail gas absorption device, and controlling the dripping temperature to be 0-10 ℃;
step S14: after the mixed fatty alcohol is dripped, reacting for 2 hours at the temperature of 0-15 ℃, removing ice water, naturally heating to 20-25 ℃, and vacuumizing for 5-6 hours under reduced pressure at the temperature;
step S15: after the hydrogen chloride gas is completely pulled out, discharging, weighing and recording, and dividing the produced dichlorinate into two parts for later use.
7. The alkyl diphenyl phosphate according to claim 5, wherein the sampling analysis in step S23 is performed by:
and (4) taking the product obtained in the step S23, and determining that the product is qualified when the alkali content of the product is 18-19%.
8. The alkyl diphenyl phosphate as claimed in claim 5, wherein the analysis and assay in step S29 is performed by:
analyzing the water content of the material, and if the water content is more than 0.1%, dehydrating until the water content is less than or equal to 0.1%;
the water content is qualified, and the finished product is obtained after the water content is qualified through testing;
the qualified standard of the assay is:
appearance: colorless transparent liquid, no suspended matter and precipitate;
specific gravity: 1.028 to 1.044;
the folding rate is as follows: 1.494-1.502 degrees;
acidity: less than or equal to 0.2 percent;
chroma: less than or equal to 50 APHA.
9. The alkyl diphenyl phosphate as claimed in claim 5, wherein the weight portions of water in step S21 and water in step S23 are respectively:
water in step S21: 1.5-2 parts;
water in step S23: 6 to 7.5 portions.
10. The alkyl diphenyl phosphate as claimed in claim 1, wherein the chemical reaction process of the alkyl diphenyl phosphate is as follows:
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2557089A (en) * | 1948-01-02 | 1951-06-19 | Monsanto Chemicals | Compositions comprising a polymerized vinyl chloride resin plasticized with monoalkyl diaryl phosphate esters |
| GB656471A (en) * | 1947-01-04 | 1951-08-22 | Monsanto Chemicals | Improvements in or relating to the preparation of organic phosphates |
| EP0478527A2 (en) * | 1990-09-28 | 1992-04-01 | Monsanto Company | Phosphate ester plasticizer |
-
2021
- 2021-07-19 CN CN202110814275.9A patent/CN113999260A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB656471A (en) * | 1947-01-04 | 1951-08-22 | Monsanto Chemicals | Improvements in or relating to the preparation of organic phosphates |
| US2557089A (en) * | 1948-01-02 | 1951-06-19 | Monsanto Chemicals | Compositions comprising a polymerized vinyl chloride resin plasticized with monoalkyl diaryl phosphate esters |
| EP0478527A2 (en) * | 1990-09-28 | 1992-04-01 | Monsanto Company | Phosphate ester plasticizer |
Non-Patent Citations (1)
| Title |
|---|
| H. R. GAMRATH等: "Chemical and Physical Properties of Alkyl Aryl Phosphates", INDUSTRIAL AND ENGINEERING CHEMISTRY, vol. 46, no. 1, pages 208 - 212 * |
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