CN113214324A - Preparation method of substituted aryl organic phosphate nucleating agent - Google Patents
Preparation method of substituted aryl organic phosphate nucleating agent Download PDFInfo
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- CN113214324A CN113214324A CN202110402473.4A CN202110402473A CN113214324A CN 113214324 A CN113214324 A CN 113214324A CN 202110402473 A CN202110402473 A CN 202110402473A CN 113214324 A CN113214324 A CN 113214324A
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- reaction
- substituted aryl
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- 229910019142 PO4 Inorganic materials 0.000 title claims abstract description 27
- 239000010452 phosphate Substances 0.000 title claims abstract description 27
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title claims abstract description 24
- 239000002667 nucleating agent Substances 0.000 title claims abstract description 19
- 125000003107 substituted aryl group Chemical group 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 53
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 39
- -1 polypropylene Polymers 0.000 claims abstract description 37
- 239000002253 acid Substances 0.000 claims abstract description 32
- 239000002904 solvent Substances 0.000 claims abstract description 31
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000011230 binding agent Substances 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 238000010438 heat treatment Methods 0.000 claims abstract description 18
- 239000000047 product Substances 0.000 claims abstract description 18
- 239000000243 solution Substances 0.000 claims abstract description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000007864 aqueous solution Substances 0.000 claims abstract description 14
- 229910052751 metal Inorganic materials 0.000 claims abstract description 13
- 238000001816 cooling Methods 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 239000012043 crude product Substances 0.000 claims abstract description 10
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 10
- 239000002184 metal Substances 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 239000002421 finishing Substances 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 30
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 claims description 10
- 238000001953 recrystallisation Methods 0.000 claims description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 239000008399 tap water Substances 0.000 claims description 7
- 235000020679 tap water Nutrition 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000005804 alkylation reaction Methods 0.000 claims description 6
- 230000018044 dehydration Effects 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 5
- 238000004458 analytical method Methods 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 238000006366 phosphorylation reaction Methods 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- JGDITNMASUZKPW-UHFFFAOYSA-K aluminium trichloride hexahydrate Chemical compound O.O.O.O.O.O.Cl[Al](Cl)Cl JGDITNMASUZKPW-UHFFFAOYSA-K 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000004321 preservation Methods 0.000 claims description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
- 239000002351 wastewater Substances 0.000 claims description 3
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 claims description 2
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 claims description 2
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 claims description 2
- SNKLPZOJLXDZCW-UHFFFAOYSA-N 4-tert-butyl-2-methylphenol Chemical compound CC1=CC(C(C)(C)C)=CC=C1O SNKLPZOJLXDZCW-UHFFFAOYSA-N 0.000 claims description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 2
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000012267 brine Substances 0.000 claims description 2
- 229960001701 chloroform Drugs 0.000 claims description 2
- 239000003712 decolorant Substances 0.000 claims description 2
- 238000004945 emulsification Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 2
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 239000004743 Polypropylene Substances 0.000 abstract description 4
- 229920001155 polypropylene Polymers 0.000 abstract description 4
- 238000001514 detection method Methods 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 239000012266 salt solution Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000007710 freezing Methods 0.000 description 6
- 230000008014 freezing Effects 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000005086 pumping Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 229930185605 Bisphenol Natural products 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 229910001463 metal phosphate Inorganic materials 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- VVSMKOFFCAJOSC-UHFFFAOYSA-L disodium;dodecylbenzene;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1 VVSMKOFFCAJOSC-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65744—Esters of oxyacids of phosphorus condensed with carbocyclic or heterocyclic rings or ring systems
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
-
- 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
- C08K5/0091—Complexes with metal-heteroatom-bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/24—Crystallisation aids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
The invention relates to a preparation method of a polypropylene nucleating agent substituted aryl organic phosphate metal salt. The method effectively solves the problems of low production efficiency, poor continuity, poor safety and low yield of the existing production method. The preparation method comprises the following specific steps: mixing substituted aryl phenol and formaldehyde aqueous solution in a solvent, adding an emulsifier and acid, heating to 80-100 ℃ under the protection of nitrogen, carrying out reflux reaction, and finishing the reaction after the detection is qualified. Adding demulsifier to separate water layer and dewatering solvent layer; step two, cooling the solution to 10-50 ℃, adding phosphorus oxychloride, stirring and dropwise adding an acid-binding agent, keeping the temperature and detecting the solution to be qualified after the dropwise adding is finished, adding water to dissolve generated hydrochloride of the acid-binding agent, removing a water layer, dissociating the water layer by using liquid alkali, dehydrating and recovering the acid-binding agent, and keeping a solvent feed liquid layer; and step three, heating the solvent feed liquid to 40-70 ℃, dropwise adding a metal alkali or salt solution, finishing the reaction, and cooling to obtain a target product crude product. And step four, dissolving the crude product obtained from the target product by using a solvent, decoloring and recrystallizing to obtain the target product. The preparation process is simple and short, and the obtained product has high purity and yield.
Description
Technical Field
The invention relates to a preparation method of an organic compound, in particular to an industrial preparation process of a disubstituted aryl organic metal phosphate of a polypropylene nucleating agent.
Background
The substituted aryl organic metal phosphate nucleating agent can promote the formation of a large number of crystal nuclei, promote the crystallization of polypropylene resin and greatly improve the rigidity and transparency of polypropylene.
The existing method for synthesizing the metal salt of the substituted diaryl organic phosphate is to obtain a solid of the substituted diaryl phenol by alkylation reaction of the substituted phenol and aldehyde in water, centrifugation and drying; the substituted diaryl phenol and phosphorus oxychloride are esterified in a solvent medium by taking organic amine as an acid-binding agent, after the esterification is finished, a hydrolysis-promoting agent is added for full hydrolysis, the mixture is centrifuged and dried to obtain substituted diaryl organic phosphate, and the substituted diaryl organic phosphate is dropwise added into water or an organic solvent to form a salt forming agent to synthesize a crude product of the substituted diaryl organic phosphate. And re-dissolving the crude product of the substituted diaryl organic metal phosphate in a solvent for recrystallization, and drying to obtain a finished product. At present, each part of the process needs to take out solids, even a large amount of water for reaction, the labor intensity is high, the production is more complicated, and the yield is not high.
Therefore, a new industrialized solution is needed to solve the above problems.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide an industrial preparation method of a substituted aryl organic phosphate nucleating agent, which has the advantages of less working procedures, no need of taking out products in each step independently, green and environment-friendly recovery of all solvents, higher yield and excellent purity of the prepared product, lower cost and accordance with the requirement of industrial large-scale production.
The preparation method of the substituted aryl organic phosphate nucleating agent comprises the following steps:
in the first step, alkylation reaction: respectively adding substituted aryl phenol raw materials and formaldehyde aqueous solution into a solvent, starting stirring, adding an emulsifier and acid, starting nitrogen protection, starting steam, heating to 80-100 ℃, preserving heat, reacting for 1-2 hours to generate substituted diaryl phenol, ensuring that the reaction analysis is qualified, stopping steam, adding the demulsifier, stopping stirring, standing and separating a water layer. Stirring the solvent layer, starting steam, heating to reflux and remove water in the system, and completely removing water to obtain the solution of the substituted diaryl phenol.
Step two, esterification reaction: under the protection of nitrogen, starting circulating water or frozen brine to cool to 10-50 ℃, adding phosphorus oxychloride, dropwise adding an acid-binding agent at constant temperature, finishing the dropwise addition, keeping the temperature, reacting for 3-8 hours to generate substituted diaryl organic phosphoryl chloride, and adding tap water to rapidly dissolve the acid-binding agent hydrochloride generated by the reaction at the temperature, wherein the reaction analysis is qualified. The stirring is turned off, the mixture is kept stand for 10 minutes to separate out a water layer, and the solution of the diaryl organic phosphoryl chloride is replaced for standby. Neutralizing the water layer with excessive liquid alkali, separating to remove wastewater, dehydrating the upper acid-binding agent, drying to no water, and continuously recycling and applying to production.
Step three, salt forming reaction: heating the obtained substituted diaryl organic phosphoryl chloride solution to 60-80 ℃ for heat preservation, dripping the salt forming agent for reaction, preserving the heat for 3-5 hours after finishing dripping, generating substituted diaryl organic phosphate metal salt through reaction, cooling and centrifuging to obtain a crude product of the substituted diaryl organic phosphate metal salt. The solvent is simply distilled and recycled for the first step of synthesis.
Fourthly, recrystallization: and adding the centrifuged crude product of the substituted diaryl organic phosphate into methanol or ethanol, heating for dissolving, adding activated carbon for decoloring, filtering, cooling for cold separation, recrystallizing and drying to obtain the qualified product of the substituted diaryl organic phosphate.
The structure of the substituted aryl phenol of the raw material in the first step is shown as the following (I):
wherein R1 represents a hydrogen atom or an alkyl group having from C1 to C6, R2 represents a hydrogen atom or an alkyl group having from C1 to C6, and R1 and R2 are the same or different.
The reaction solvent is at least one of the following: dichloromethane, trichloromethane, cyclohexane, heptane, benzene, toluene, xylene, 1-dichloroethane, 1, 2-dichloroethane, 120# petroleum ether, 150# petroleum ether.
The acid used is at least one of the following: sulfuric acid, hydrochloric acid, p-toluenesulfonic acid.
The emulsifier is at least one of the following: sodium dodecylbenzene sulfonate and sodium lauryl sulfate.
The demulsifier is at least one of the following: tetrabutylammonium bromide, tetramethylammonium bromide, tetrabutylammonium chloride, tetramethylammonium chloride, triethylamine and dimethylamine aqueous solution.
In the first step, the substituted aryl phenol is preferably: p-methylphenol, p-ethylphenol, p-tert-butylphenol, 2, 4-dimethylphenol, 2, 4-di-tert-butylphenol, 4-methyl-2-tert-butylphenol, 4-tert-butyl-2-methylphenol.
In the first step, every 1kg of substituted aryl phenol corresponds to 3-7L of solvent; preferably 3-5L, the excessive reaction time of the solvent is prolonged, and the feeding amount is reduced, so that the method is uneconomical.
In the first step, monophenol substitute is generated due to excessive addition of formaldehyde, addition of the emulsifier is controlled, a too small system cannot be completely emulsified, and a large amount of foam is generated in an excessive reaction process to influence the reaction. 0.5-0.7 mol of formaldehyde is required to be added in each mol of substituted phenol reaction, and the formaldehyde is preferably a formaldehyde water solution with the mass of 37%; the mass of the acid is 0.5-1% of the weight of the substituted phenol; 0.001-0.01 kg of emulsifier is added to each 1L of solvent; the using molar weight ratio of the demulsifier to the emulsifier is 1-1.5: 1.
in the first step, the alkylation reaction temperature is 80-100 ℃, preferably 80-85 ℃, the layering temperature is 80-100 ℃, preferably 80-90 ℃, and the dehydration temperature is the boiling point of the solvent.
In the first step, side reactions increase when the alkylation time is too long, and the reaction time is preferably 1 to 3 hours.
The method has the advantages that the material feeding is carried out by adopting a one-pot method, the operation is simple, a large amount of water is replaced by a solvent for reaction, the emulsification and layering are directly carried out after the reaction, the process of washing the product by water is reduced, the labor intensity of workers is greatly reduced, the reaction time is greatly shortened, and the product yield is high.
In the first step, the structure of the generated substituted diaryl phenol is shown as the following (II):
wherein R1 represents a hydrogen atom or an alkyl group having from C1 to C6, R2 represents a hydrogen atom or an alkyl group having from C1 to C6, and R1 and R2 are the same or different.
In the second step, the acid-binding agent is at least one of the following: triethylamine, N-dimethylaniline, N-diisopropylethylamine;
in the second step, phosphorus oxychloride is added once, so that the weak acidity of the reaction process of the system can be maintained, bisphenol is not easy to oxidize, the appearance of the product is good, and the acid-binding agent is adopted for dropwise adding reaction in the reaction.
In the second step, phosphorus oxychloride can volatilize when the reaction temperature is too high, the reaction is too slow when the temperature is too low, the reaction temperature is preferably 20-30 ℃, and the dripping time of the acid-binding agent is controlled according to the temperature.
In the second step, the heat preservation time is preferably 3-8 hours after the dropwise addition.
In the second step, the post-treatment of the disubstituted aryl phosphoryl chloride generated after the phosphorylation reaction is finished is to quickly add tap water, quickly dissolve the generated acid-binding agent hydrochloride and remove the acid-binding agent hydrochloride by layers, and simultaneously ensure that the disubstituted aryl phosphoryl chloride is not hydrolyzed.
In the second step, the molar ratio of the usage amount of the phosphorus oxychloride to the substituted phenol in the first step is 0.5-0.8: 1, preferably 0.6 to 0.7: 1, the molar ratio of the use amount of the acid-binding agent to phosphorus oxychloride is 2-3: 1, preferably 2.5-3: 1.
in the second step, the post-treatment temperature after the reaction is 10-50 ℃, preferably 30-40 ℃, and the volume ratio of the post-treatment water amount to the initial solvent is 0.5-1: 1, the post-treatment time is strictly controlled.
In the second step, recovering the acid-binding agent, wherein the molar ratio of the alkali to the acid-binding agent is 1-1.5: 1, preferably 1.2 to 1.5: 1, a water removal method of an acid binding agent, which is carried out by adopting reflux dehydration and caustic soda flakes drying together.
In the second step, the acid-binding agent hydrochloride is removed by washing, and the next step of reaction can be carried out without hydrolyzing into corresponding substituted aryl phosphate after the reaction is finished, so that the acid-binding agent is directly recovered, the time is saved, and the economic benefit is greatly improved by recovering and reusing the acid-binding agent.
In the second step, the structure of the generated substituted diaryl organic phosphoryl chloride is shown as the following (III):
wherein R1 represents a hydrogen atom or an alkyl group having from C1 to C6, R2 represents a hydrogen atom or an alkyl group having from C1 to C6, and R1 and R2 are the same or different.
Thirdly, the salt forming agent is at least one of the following substances: sodium hydroxide, potassium hydroxide, lithium hydroxide, aluminum trichloride hexahydrate, aluminum sulfate, lithium chloride;
in the third step, the salt forming temperature is too low, the reaction is too slow, the temperature of the salt forming reaction is preferably 60-80 ℃, and the temperature is kept for 3-5 hours after the reaction is finished.
In the third step, the salt forming agent needs to completely react the substituted aryl phosphoryl chloride in the second step, otherwise, the generated substituted aryl phosphate affects the quality and application of the final product, and the usage amount of the salt forming agent is preferably 1-3 times of the theoretical molar usage amount.
In the third step, after salt formation is finished, the centrifuged solvent is continuously recycled to the synthesis in the first step through simple distillation.
The structural formula of the synthesized substituted diaryl organic phosphate metal salt in the third step is shown as the following (IV) or (V):
wherein, in the structure (IV), M represents one of the following metal elements: sodium, lithium, potassium; wherein in the structure (V), M represents the following metal elements: aluminum;
in the fourth step, the solvent used for recrystallization is methanol, ethanol or their aqueous solution and mixed solution, and each 1kg of crude product corresponds to 3-5L of solvent for recrystallization.
In the fourth step, in order to achieve better effect, the decolorant used is preferably weakly alkaline activated carbon.
In the fourth step, the solvent for recrystallization centrifugation is distilled or rectified according to the use requirement and is mechanically applied to the recrystallization step.
The invention has the following beneficial effects:
according to the invention, the organic solvent is adopted to replace the traditional water reaction in the first step, and the reaction is finished, so that the centrifugation and a large amount of water washing are avoided by direct layering, and the method is green and environment-friendly; according to the three-step synthesis reaction, materials do not need to be taken out in the process, so that the contact of a manual process and corresponding waste are avoided, the labor force is saved, the reaction yield of the method is high, the purity of the final product is high, the process is short, all process solvents and the like are recycled and reused, the requirement of industrial batch production is met, the requirement on equipment is low, and the whole method has good applicability. The invention optimizes the use amount of materials synthesized by each part of the reaction, and the prepared finished product has high yield and high purity.
Detailed Description
Example 1: a preparation method of a substituted aryl organic phosphate nucleating agent comprises the following specific steps:
firstly, 2800L of toluene is pumped into a 5000L reaction kettle, 412kg of 2, 4-di-tert-butylphenol and 90kg of 37% formaldehyde aqueous solution are sequentially added, 1kg of sodium dodecyl benzene sulfonate and 3kg of concentrated sulfuric acid are added, nitrogen is introduced for protection, steam is started to rapidly heat to 80 ℃, the temperature is controlled to be 80-85 ℃ by utilizing steam and circulating water, sampling analysis is carried out after 2.5 hours of reaction, the HPLC content is 97%, and the raw material residue is 0.2%, and the reaction is finished. Adding 1.5kg of tetrabutylammonium bromide, stirring for 15 minutes, standing for 30 minutes, and removing a lower water layer to treat sewage. Heating the upper layer to 110 ℃, refluxing and dehydrating, observing that the water separator does not have water to be azeotroped out, and closing steam after dehydration.
And secondly, starting freezing the solution, cooling to 20 ℃, pumping 200kg of phosphorus oxychloride, dropwise adding 320kg of triethylamine at a constant temperature, stopping the dropwise adding within 3 hours, stopping freezing, keeping the temperature for 8 hours, analyzing the HPLC content, and stopping the reaction of the bisphenol content of 0.4% in the first step. At the temperature of 40 ℃, 1000L of tap water is quickly added, the mixture is kept stand for 10 minutes after the addition, and the hydrochloric acid solution on the lower layer is quickly separated to enter a triethylamine recovery working section.
And thirdly, heating the solution on the upper layer to 60 ℃, preserving the temperature, dropwise adding 625kg of 32% liquid caustic soda for 2 hours, preserving the temperature for 5 hours after the dropwise adding is finished, cooling to 25 ℃, centrifuging, and distilling the toluene mother liquor for reuse. The material content is 99.3 percent, and the dry weight is 467.8 kg.
Fourthly, the materials are recrystallized and dried by 1400L of methanol water to obtain 438kg of finished product of 2, 2' -methylene-bis (4, 6-di-tert-butylphenyl) sodium phosphate with the content of 99.8 percent and the yield of 86.2 percent.
Example 2: a preparation method of a substituted aryl organic phosphate nucleating agent comprises the following specific steps:
firstly, pumping 1200L of 1, 2-dichloroethane into a 3000L reaction kettle, sequentially adding 412kg of 2, 4-di-tert-butylphenol and 90kg of 37% formaldehyde aqueous solution, adding 1kg of sodium dodecyl benzene sulfate and 3kg of concentrated sulfuric acid, introducing nitrogen for protection, starting steam, rapidly heating to 80 ℃, controlling the temperature to be 80-85 ℃ by utilizing the steam and circulating water, reacting for 2.5 hours, sampling and analyzing, wherein the HPLC content is 95%, and the raw material residue is 0.8%, and finishing the reaction. Adding 1kg of tetramethylammonium chloride, stirring for 15 minutes, standing for 30 minutes, removing the lower layer feed liquid to a synthesis kettle, starting steam, heating to 87 ℃, refluxing and dehydrating, observing that the water separator does not have water to be azeotroped out, and closing the steam after the dehydration is finished.
And secondly, starting freezing the solution, cooling to 20 ℃, pumping 220kg of phosphorus oxychloride, dropwise adding 300kg of triethylamine at a constant temperature, stopping the dropwise adding within 3 hours, stopping freezing, keeping the temperature for 3 hours, analyzing the HPLC content, and stopping the reaction of the bisphenol content of 0.1% in the first step. At the temperature of 40 ℃, 1000L of tap water is quickly added, the mixture is kept stand for 10 minutes after the addition, and the mixture is quickly separated into lower-layer material liquid to be sent to a synthesis kettle.
And thirdly, heating the feed liquid of the 1, 2-dichloroethane to 60 ℃, preserving heat, dropwise adding an aqueous solution of aluminum trichloride hexahydrate (67 kg of the weight of the aluminum trichloride), dropwise adding for 4 hours, finishing dropwise adding, preserving heat for 6 hours, adding an aqueous solution of 10% sodium hydroxide to adjust the pH value to about 6, preserving heat for 1 hour, cooling to 25 ℃, centrifuging, and distilling the 1, 2-dichloroethane mother liquor for reuse. The material content is 99.3 percent, and the weight on dry basis is 463.2 kg.
Fourthly, recrystallizing and drying the materials by using 1400L of absolute ethyl alcohol to obtain a finished product of 2, 2' -methylene-bis (4, 6-di-tert-butyl phenyl phosphate) basic aluminum, wherein the total weight is 430kg, the content is 99.4 percent, and the yield is 84.8 percent.
Example 3: a preparation method of a substituted aryl organic phosphate nucleating agent comprises the following specific steps:
firstly, pumping 1200L of dimethylbenzene into a 3000L reaction kettle, sequentially adding 412kg of 2, 4-di-tert-butylphenol and 90kg of 37% formaldehyde aqueous solution, adding 1kg of sodium dodecyl benzene sulfonate and 5kg of p-toluenesulfonic acid, introducing nitrogen for protection, starting steam, rapidly heating to 80 ℃, controlling the temperature to 80-85 ℃ by utilizing the steam and circulating water, reacting for 2 hours, sampling and analyzing, wherein the HPLC content is 97.5%, and the raw material residue is 0.1%, and the reaction is finished. Adding 7kg of triethylamine, stirring for 15 minutes, standing for 30 minutes, separating lower-layer wastewater, starting steam, heating to 140 ℃, refluxing and dehydrating, observing that no water is azeotroped out from a water separator, and closing the steam after the dehydration is finished.
And secondly, starting freezing the solution, cooling to 30 ℃, pumping 220kg of phosphorus oxychloride, dropwise adding 300kg of triethylamine at a constant temperature, stopping the dropwise adding within 3 hours, stopping freezing, keeping the temperature for 7 hours, analyzing the HPLC content, and stopping the reaction of the bisphenol content of 0.8% in the first step. At the temperature of 45 ℃, 1000L of tap water is quickly added, the mixture is kept stand for 10 minutes after the addition, and the hydrochloric acid solution on the lower layer is quickly separated to enter a triethylamine recovery working section.
And thirdly, heating the xylene feed liquid to 60 ℃, preserving the temperature, dropwise adding 10% lithium hydroxide aqueous solution for 4 hours, preserving the temperature for 6 hours after the dropwise adding is finished, cooling to 25 ℃, centrifuging, and distilling the xylene mother liquid for reuse. The material content is 99.8 percent, and the dry weight is 450 kg.
Fourthly, recrystallizing and drying the materials by using 1500L of methanol to obtain a finished product of the 2, 2' -methylene (4, 6-di-tert-butylphenyl) lithium phosphate, wherein the total amount of the finished product is 410kg, the content is 99.9 percent, and the yield is 83.3 percent.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solutions of the present invention and not for limiting the same, and although the present invention is described in detail with reference to the above embodiments, those of ordinary skill in the art should understand that: modifications and equivalents may be made to the embodiments of the invention without departing from the spirit and scope of the invention, which is to be covered by the claims.
It will be appreciated by those skilled in the art that the invention may be embodied in other specific forms without departing from the spirit or essential characteristics thereof. The embodiments disclosed above are therefore to be considered in all respects as illustrative and not restrictive. All changes which come within the scope of or equivalence to the invention are intended to be embraced therein.
Claims (10)
1. A preparation method of a substituted aryl organic phosphate nucleating agent is characterized by comprising the following steps:
in the first step, alkylation reaction: respectively adding substituted aryl phenol raw materials and a formaldehyde aqueous solution into a solvent, starting stirring, adding an emulsifier and acid, starting nitrogen protection, starting steam, heating to 80-100 ℃, preserving heat, reacting for 1-5 hours to generate substituted diaryl phenol, ensuring that the reaction analysis is qualified, stopping steam, adding an emulsion breaker, stopping stirring, standing and separating a water layer; stirring the solvent layer, starting steam, heating to reflux and remove water in the system, and removing water to obtain a solution of substituted diaryl phenol;
the structure of the raw material substituted aryl phenol is shown as the following (I):
wherein R1 represents a hydrogen atom or an alkyl group having from C1 to C6, R2 represents a hydrogen atom or an alkyl group having from C1 to C6, and R1 and R2 are the same or different;
the solvent is at least one of the following: dichloromethane, trichloromethane, cyclohexane, heptane, benzene, toluene, xylene, 1-dichloroethane, 1, 2-dichloroethane, 120# petroleum ether, 150# petroleum ether;
the acid is at least one of the following: sulfuric acid, hydrochloric acid, p-toluenesulfonic acid;
the emulsifier is at least one of the following: sodium dodecylbenzene sulfonate and sodium dodecyl sulfate;
the demulsifier is at least one of the following: tetrabutylammonium bromide, tetramethylammonium bromide, tetrabutylammonium chloride, tetramethylammonium chloride, triethylamine and dimethylamine aqueous solution;
the structure of the obtained substituted diaryl phenol is shown as the following (II):
and step two, phosphorylation reaction: under the protection of nitrogen, starting circulating water or frozen brine to cool the substituted diaryl phenol (II) solution to 10-50 ℃, adding phosphorus oxychloride, dropwise adding an acid-binding agent at constant temperature, finishing the dropwise adding, carrying out heat preservation reaction for 3-8 hours to generate substituted diaryl organic phosphorus oxychloride, and adding tap water to quickly dissolve the acid-binding agent hydrochloride generated by the reaction at the temperature, wherein the reaction analysis is qualified; stopping stirring, standing for 10 minutes, separating out a water layer, and replacing the solution of diaryl organic phosphoryl chloride for later use; neutralizing the water layer with excessive liquid alkali, separating to remove wastewater, dehydrating the upper acid-binding agent, drying until no water exists, and continuously recycling and applying to production;
the acid-binding agent is at least one of the following components: triethylamine, N-dimethylaniline, N-diisopropylethylamine;
the structure of the obtained substituted diaryl organic phosphoryl chloride is shown as the following (III):
step three, salt forming reaction: heating the obtained substituted diaryl organic phosphoryl chloride solution to 60-80 ℃, preserving heat, dropwise adding a salt forming agent for reaction, preserving heat for 3-5 hours after dropwise adding, generating substituted diaryl organic phosphate metal salt through reaction, cooling and centrifuging to obtain a crude product of the substituted diaryl organic phosphate metal salt;
the salt forming agent is at least one of the following: sodium hydroxide, potassium hydroxide, lithium hydroxide, aluminum trichloride hexahydrate, aluminum sulfate, lithium chloride;
the structural formula of the obtained substituted diaryl organic phosphate metal salt is shown as the following (IV) or (V):
wherein, in the structure (IV), M represents one of the following metal elements: sodium, lithium, potassium; wherein in the structure (V), M represents the following metal elements: aluminum;
fourthly, recrystallization: and adding the centrifuged crude product of the substituted diaryl organic phosphate into methanol or ethanol, heating for dissolving, adding activated carbon for decoloring, filtering, cooling for cold separation, recrystallizing and drying to obtain the qualified product of the substituted diaryl organic phosphate.
2. The method of preparing a substituted aryl organophosphate nucleating agent as claimed in claim 1, wherein in the first step the substituted aryl phenol is: p-methylphenol, p-ethylphenol, p-tert-butylphenol, 2, 4-dimethylphenol, 2, 4-di-tert-butylphenol, 4-methyl-2-tert-butylphenol, 4-tert-butyl-2-methylphenol; the substituted aryl phenol and formaldehyde aqueous solution are subjected to two-phase emulsification reaction in an organic solvent.
3. The method for preparing a nucleating agent for substituted aryl organophosphates according to claim 1, wherein, in the first step, after the alkylation reaction is finished, the generated substituted diaryl phenol is subjected to post-treatment, directly demulsified and separated into water layers, and then dehydrated; 3-7L of solvent is used for each 1kg of substituted aryl phenol.
4. The method for preparing the nucleating agent of substituted aryl organophosphate as claimed in claim 1, wherein in the first step, 0.5 to 0.7 mol of formaldehyde is added per mol of substituted aryl phenol; the mass of the acid is 0.5-1% of the weight of the substituted phenol; 0.001-0.01 kg of emulsifier is added to each 1L of solvent; the using molar weight ratio of the demulsifier to the emulsifier is 1-1.5: 1.
5. the method of claim 1, wherein in the first step, the reaction temperature is 80 ℃ to 100 ℃, the layering temperature is 80 ℃ to 100 ℃, and the dehydration temperature is the boiling point of the solvent.
6. The method for preparing a nucleating agent for substituted aryl organophosphates as claimed in claim 1, wherein in the second step, the secondary aryl phosphoryl chloride generated after the phosphorylation reaction is finished is post-treated, tap water is added, and the product acid-binding agent hydrochloride is removed by rapid washing.
7. The method for preparing a nucleating agent for substituted aryl organophosphates according to claim 1, wherein in the second step, the molar ratio of the amount of phosphorus oxychloride used to the amount of substituted aryl phenol in the first initial step is 0.5 to 0.8: 1, the molar ratio of the acid-binding agent to the phosphorus oxychloride is 2-3: 1.
8. the method for preparing a nucleating agent for substituted aryl organophosphates according to claim 1, wherein in the second step, the temperature of the phosphorylation reaction is 10 ℃ to 50 ℃ and the reaction time is 3 to 8 hours; and (3) after the reaction is finished, carrying out post-treatment at the temperature of 10-50 ℃, wherein the volume ratio of the post-treated water quantity to the initial solvent is 0.5-1: 1.
9. the preparation method of the substituted aryl organic phosphate nucleating agent according to claim 1, characterized in that, in the third step, the temperature of salt forming reaction is 60-80 ℃, and the temperature is kept for 3-5 hours after the reaction; the usage amount of the salt forming agent is 1-3 times of the theoretical molar usage amount.
10. The method for preparing a nucleating agent for substituted aryl organophosphates according to claim 1, wherein in the fourth step, the solvent used for recrystallization is methanol, ethanol or their aqueous solutions and mixed solutions, and 3 to 5L of the solvent used for recrystallization per 1kg of crude product; the decolorant is alkalescent active carbon, and the recrystallization temperature is 60-80 ℃.
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