CN116925132B - Preparation method of fine-particle-size dialkyl phosphinate - Google Patents
Preparation method of fine-particle-size dialkyl phosphinate Download PDFInfo
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- CN116925132B CN116925132B CN202310804518.XA CN202310804518A CN116925132B CN 116925132 B CN116925132 B CN 116925132B CN 202310804518 A CN202310804518 A CN 202310804518A CN 116925132 B CN116925132 B CN 116925132B
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- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000002585 base Substances 0.000 claims abstract description 18
- 239000010419 fine particle Substances 0.000 claims abstract description 15
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 9
- 239000000243 solution Substances 0.000 claims description 76
- 238000006243 chemical reaction Methods 0.000 claims description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 28
- 239000000725 suspension Substances 0.000 claims description 24
- 239000002244 precipitate Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- 238000001556 precipitation Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 239000002798 polar solvent Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 159000000007 calcium salts Chemical class 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 159000000021 acetate salts Chemical class 0.000 claims description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 150000003751 zinc Chemical class 0.000 claims 1
- -1 alkali metal salt Chemical class 0.000 abstract description 3
- 230000001276 controlling effect Effects 0.000 abstract description 2
- 230000001105 regulatory effect Effects 0.000 abstract description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002245 particle Substances 0.000 description 45
- 239000000047 product Substances 0.000 description 39
- 235000019441 ethanol Nutrition 0.000 description 20
- 238000009826 distribution Methods 0.000 description 15
- 238000005406 washing Methods 0.000 description 11
- 238000005054 agglomeration Methods 0.000 description 8
- 230000002776 aggregation Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 239000012266 salt solution Substances 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000004321 preservation Methods 0.000 description 4
- 238000001878 scanning electron micrograph Methods 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- 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 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
- 230000006911 nucleation Effects 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JLDSOYXADOWAKB-UHFFFAOYSA-N aluminium nitrate Chemical compound [Al+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O JLDSOYXADOWAKB-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- DRDKFCAHTAHYER-UHFFFAOYSA-N bis(2-methylpropyl)phosphinic acid Chemical compound CC(C)CP(O)(=O)CC(C)C DRDKFCAHTAHYER-UHFFFAOYSA-N 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- KTLIMPGQZDZPSB-UHFFFAOYSA-N diethylphosphinic acid Chemical compound CCP(O)(=O)CC KTLIMPGQZDZPSB-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010979 pH adjustment Methods 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- NTMNCAUULJCPPH-UHFFFAOYSA-M sodium;bis(2-methylpropyl)phosphinate Chemical compound [Na+].CC(C)CP([O-])(=O)CC(C)C NTMNCAUULJCPPH-UHFFFAOYSA-M 0.000 description 2
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 2
- 229940007718 zinc hydroxide Drugs 0.000 description 2
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 2
- RZLVQBNCHSJZPX-UHFFFAOYSA-L zinc sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Zn+2].[O-]S([O-])(=O)=O RZLVQBNCHSJZPX-UHFFFAOYSA-L 0.000 description 2
- XNDZQQSKSQTQQD-UHFFFAOYSA-N 3-methylcyclohex-2-en-1-ol Chemical compound CC1=CC(O)CCC1 XNDZQQSKSQTQQD-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000519995 Stachys sylvatica Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 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 description 1
- AMVQGJHFDJVOOB-UHFFFAOYSA-H aluminium sulfate octadecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O AMVQGJHFDJVOOB-UHFFFAOYSA-H 0.000 description 1
- 239000001164 aluminium sulphate Substances 0.000 description 1
- 235000011128 aluminium sulphate Nutrition 0.000 description 1
- JGDITNMASUZKPW-UHFFFAOYSA-K aluminium trichloride hexahydrate Chemical compound O.O.O.O.O.O.Cl[Al](Cl)Cl JGDITNMASUZKPW-UHFFFAOYSA-K 0.000 description 1
- 229940009861 aluminum chloride hexahydrate Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- WCOATMADISNSBV-UHFFFAOYSA-K diacetyloxyalumanyl acetate Chemical compound [Al+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WCOATMADISNSBV-UHFFFAOYSA-K 0.000 description 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- WMDPJKZHARKRQI-UHFFFAOYSA-N dipropylphosphinic acid Chemical compound CCCP(O)(=O)CCC WMDPJKZHARKRQI-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 1
- 229940061634 magnesium sulfate heptahydrate Drugs 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- TZPNUVYGCPWJKV-UHFFFAOYSA-M sodium dipropylphosphinate Chemical compound C(CC)P([O-])(=O)CCC.[Na+] TZPNUVYGCPWJKV-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- LPFYDEANGXVAOA-UHFFFAOYSA-M sodium;diethylphosphinate Chemical compound [Na+].CCP([O-])(=O)CC LPFYDEANGXVAOA-UHFFFAOYSA-M 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
The invention provides a preparation method of fine particle size dialkyl phosphinate, which comprises the steps of regulating and controlling pH value by using a solution integrating dialkyl phosphinic acid and alkali metal salt in an alcohol-water system, and sequentially completing double decomposition reaction and acid-base neutralization reaction in the solution system to obtain the fine particle size dialkyl phosphinate with higher yield and purity.
Description
Technical Field
The invention belongs to the field of organic hypophosphite flame retardants, and particularly relates to a preparation method of fine particle size dialkyl phosphinate with extremely low swelling and good dispersion compatibility in a coating resin system.
Background
The dialkylphosphinate has high heat stability, high phosphorus content, high whiteness, low density and high flame retardant efficiency, is widely applied to polyamide, polyester, polyurethane, acrylic resin and epoxy resin materials, and has specific physical and electrical properties (high CTI and high glow wire ignition temperature) in polyamide and polyester materials, high flame retardance, low smoke density and high oxygen index in polyurethane and acrylic resin, and is different from the requirements of coarse particle diameter and good blanking in engineering plastic application, and the flame retardant has the requirements of fine particle diameter, easy dispersion uniformity and good compatibility in polyurethane or acrylic resin. However, the fine particle size product requires a controlled particle size distribution and controls the content interval of the minimum particle size (D10) and the maximum particle size (D100) at the same time. The finest particle size ratio is easy to agglomerate in the resin distribution process, the viscosity of the base material resin is excessively high, the subsequent processing is not facilitated, the particle size is excessively thick, and the finished product (such as TPU cable and fabric leather product) is easy to have granular feel or white spots, so that the particle size distribution needs to be accurately controlled, the flame retardant is better applied to the coating resin and the elastomer, and the invention prepares fine particle size powder with good particle size distribution and low agglomeration through the reaction process control and the alcohol water system, thereby realizing low swelling, good compatibility and dispersibility in the resin system.
The preparation of fine particle size dialkylphosphinate products generally has two methods, namely, crushing the prepared crude dialkylphosphinate to prepare a fine particle size product; secondly, the particle size is controlled in the synthetic crystallization process. In the first method, the content of the maximum and minimum particle size ranges is difficult to control to meet the requirement, and the agglomeration problem is easy to occur when the content of the superfine particle size is higher, so that the particle size distribution is controlled by adopting the second method.
The dialkylphosphinic acid salts are prepared by double decomposition reaction of alkali metal dialkylphosphinate salts and precipitated metal salts, or by acid-base neutralization of dialkylphosphinic acid and hydroxide or metal oxide. The pH adjustment and the removal and washing of byproducts are taken into consideration in the double decomposition reaction, the particle size of the product is larger, the distribution is wider in neutral or weak alkaline environment, the purity of the product is higher, the particle size is finer and the distribution is narrower in weak acidic pH environment, but strong acid such as sulfuric acid or phosphoric acid is often adopted in the pH adjustment process, new anionic impurities can be introduced by adding the strong acid, excessive acid is difficult to thoroughly wash after being attached to the product precipitate, and other phosphate precipitates can be introduced by the phosphoric acid, so that the purity and the yield of the product are not high due to the factors; in the acid-base neutralization process, the solubility of hydroxide or metal oxide as the base in a solvent is low, and the hydroxide or metal oxide is usually added directly into a solid powder or added into a suspension to participate in the reaction, wherein alkali particles need to be sufficiently dispersed in the suspension to effectively participate in the reaction, and the generated precipitate products can coat the alkali particles, so that the reaction is insufficient and the product is mixed with the base, particularly when the concentration of the suspension is high, which severely limits the production efficiency and purity of the acid-base reaction method.
On the other hand, in the prior art, when preparing nano materials, an alcohol-water method can be used for controlling the particle size, and the principle of preparing ultrafine particle size crystals by the alcohol-water method is that solid particles are generated in a liquid phase through the processes of nucleation, growth, coalescence and agglomeration, and the size of the particles is in a direct proportion relation with the dielectric constant of the solution, so that the size of the particle nucleation can be controlled by changing the dielectric constant of the solution. Alcohol-water processes utilize alcohols, which generally have a lower dielectric constant than water, to reduce the solubility and solubility of the crystal products in alcohol-water solutions, allowing them to become supersaturated and nucleate, thereby producing fine particles. In addition, the existence of alcohol groups in the reaction process can prevent the non-bridging hydroxyl groups from being connected with the surfaces of the particles through hydrogen bonds to form hard agglomeration, and meanwhile, the steric hindrance effect of the alcohol can also reduce the collision probability of the particles so as to reduce the formation of soft agglomeration, so that the method is favorable for producing the particles with small particles, good narrowness and good dispersibility.
Dialkylphosphinate products have not been reported to be prepared by the alcohol-water process.
Disclosure of Invention
According to the invention, the pH value is regulated and controlled by adopting the integrated solution of the dialkylphosphinic acid and the alkali metal salt, the double decomposition reaction and the acid-base neutralization reaction are successively completed in a solution system, new anions are not introduced into the dialkylphosphinic acid, excessive acid is not required to be washed after the double decomposition reaction, the excessive acid is removed through the acid-base neutralization reaction, the product is continuously generated on the other hand, the yield is improved, and the concentration of the residual acid is low, so that the added alkali suspension is low in concentration, easy to disperse and not easy to be coated by the product, and the defects of the double decomposition reaction and the acid-base neutralization reaction are overcome in the process.
In another aspect, the present invention prepares a high quality, narrow particle size distribution and low swelling dialkylphosphinate product using a polar solvent, particularly an alcohol-water reaction system, depending on the specifics of the dialkylphosphinate crystallization process.
The technical scheme of the invention is as follows:
a preparation method of dialkyl phosphinate with fine particle size is characterized in that:
Step one: dissolving dialkylphosphinic acid and alkali metal dialkylphosphinate salts selected from sodium or potassium in a solvent to prepare a solution ①, said alkyl groups being selected from C1-C6 alkyl groups, preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl;
Step two: dissolving a metal salt in water to prepare a solution ②, wherein the metal salt is selected from soluble aluminum salt, magnesium salt and calcium salt;
the soluble aluminium, magnesium and calcium salts are selected from the group consisting of chloride, sulphate, nitrate or acetate salts of the above metals, particularly preferably from the group consisting of aluminium chloride, aluminium sulphate, aluminium nitrate, aluminium acetate, magnesium sulphate, magnesium nitrate, magnesium acetate, magnesium chloride, calcium chloride or calcium nitrate;
Wherein the ratio of dialkylphosphinic acid to alkali metal dialkylphosphinate in solution ① is 1:1-10.
Wherein the solid concentration of the solution ② metal salt solution is 10-50%, preferably 10-30%;
Step three: dispersing an alkaline substance in a solvent to prepare a suspension ③, wherein the alkaline substance is selected from hydroxide or oxide of magnesium, aluminum, zinc, calcium or barium;
Preferably, the concentration of solids in the suspension ③ is 10-50%, more preferably 10-30%.
Step four: fully mixing the solution ① and the solution ② to start double decomposition reaction until precipitation is complete, and slowly adding the suspension ③ to complete acid-base neutralization reaction;
Preferably, in the fourth step, the reaction is started in a manner of adding the solution ① and the solution ② simultaneously, the precipitation reaction temperature is 50-90 degrees, preferably 70-80 degrees, the adding time of the solution ① and the solution ② is 1-5 h, the reaction time is 1-6 h after the adding is completed, and the precipitation is complete, preferably the adding manner is dropwise adding.
Step five: separating and purifying the precipitate to obtain the dialkylphosphinate.
Preferably, the molar ratio of alkali metal dialkylphosphinate in solution ① to metal salt solution in solution ② is from 1:2 to 6, depending on the valence of the selected metal salt; likewise the molar ratio of dialkylphosphinic acid in solution ① to basic material in solution ③ is 1:2-3, depending on the valence of the selected metal salt.
Further, the reaction is carried out in an alcohol polar solvent-water system;
specifically, at least one solvent of the solution ① and the suspension ③ is an alcohol-based polar solvent or an alcohol-based polar solvent-water mixed solvent, and preferably both, more preferably the solution ① is an alcohol-based polar solvent-water solution, and the suspension ③ is an alcohol-based polar solvent-water suspension.
When the solution ① is an alcohol polar solvent-aqueous solution, the addition amount of the alcohol polar solvent is 5-20% of the total water amount, and the addition amount of the alcohol polar solvent is related to the dialkylphosphinic acid, because the dialkylphosphinic acid has good solubility in the alcohol polar solvent.
Preferably the polar alcoholic solvent is selected from methanol, ethanol or propanol.
The invention adopts a mode of combining double decomposition reaction and acid-base neutralization reaction, and successfully overcomes the defects in the prior art.
Drawings
FIG. 1 is a graph showing the particle size distribution of a dialkylphosphinate salt prepared according to the present invention;
FIG. 2 is a graph showing the particle size distribution of dialkylphosphinate prepared according to the present invention;
FIG. 3 is a graph showing the particle size distribution of dialkylphosphinate prepared according to the present invention;
FIG. 4 is a graph of the particle size distribution of a sample fine particle size (D50 3.541 μm) dialkylphosphinate;
FIG. 5 is a particle SEM image of a dialkylphosphinate prepared according to the present invention;
FIG. 6 is a particle SEM image of a sample fine particle size (D50 3.541 μm) dialkylphosphinate.
Detailed Description
In the examples below, each of the dialkylphosphinic acid and the sodium salt of dialkylphosphinic acid was prepared in the laboratory; the metal compounds such as aluminum sulfate, zinc sulfate, aluminum hydroxide, zinc hydroxide, ethanol, propanol, etc. are all conventional chemicals purchased from Amara Ding Shiji net or Michelin reagent
Example 1
Diethyl phosphinic acid (1.05 mol,128.3 g, homemade) and sodium diethyl phosphinate (5 mol,721 g, homemade) are dissolved in 3128 g pure water, after complete dissolution, industrial absolute ethanol 245 g is added, an aqueous alcohol solution ① is prepared, and the pH of the solution is measured; aluminum nitrate nonahydrate (1.67 mol,625.22 g) is dissolved in 2500 g water to prepare a metal salt solution ②; dispersing aluminum hydroxide (0.33 mol, 26 g) in 94 g water, adding 9.4 g industrial absolute ethyl alcohol, stirring and dispersing uniformly to prepare suspension ③; and (3) simultaneously dropwise adding the solution ① and the solution ② to start the reaction, wherein the stirring speed of a reaction system is 300 rpm, the reaction temperature is 70 ℃, the dropwise adding of the solution ① and the solution ② in 1 h is completed, the heat preservation reaction is continued for 2 hours until the precipitation is complete, then the prepared suspension ③ is slowly poured into a reaction container to complete the acid-base neutralization reaction, the heat preservation reaction is carried out for 2 hours until the precipitation is complete, and the reaction completion degree is detected according to the pH value and the ion concentration of the solution. And after the reaction is finished, filtering out a precipitate while the precipitate is hot, washing the precipitate with hot water until the filtrate meets the requirement, and after the washing is finished, putting the precipitate into a 130-DEG oven for drying to obtain a finished product 745 g. The yield was about 95.4%.
Particle size measurement the particle size of the product was measured by a laser diffraction particle size meter (equipment model BT-9300 ST): d10 1.061 μm, D50.45 μm, D95.33 μm, D100.26.43 μm;
The bulk density of the product was measured by a bulk densitometer (bulk densitometer model BT-100), and the bulk density was measured: 0.30 g/ml;
The particle size diagram of the product is shown in figure 1; the particle size distribution of the product of the present invention is narrower relative to the particle size distribution of the sample fine particle size (D50 3.541 μm) dialkylphosphinate (see figure 4).
The SEM image of the product is shown in figure 5, and compared with the SEM image of the particles of the dialkylphosphinate with the external sample fine particle diameter (D50 3.541 mu m) (see figure 6), the microscopic morphology of the product is shown under 10000 times magnification (5 mu m scale reference), the particles of the product are independent and uniform in size, the morphology between the block shape and the rod shape is shown, the nucleation crystallization morphology is consistent, the performance dispersibility is good, and the agglomeration problem is avoided; the commercial external samples have obvious chip agglomeration and accumulation, which indicates that agglomeration occurs in the process of testing sample preparation and the appearance difference is large.
Example 2
Dipropylphosphinic acid (1.05 mol,157.7 g, homemade) and sodium dipropylphosphinate (4 mol,688.8 g, homemade) were dissolved in 3541 g pure water, after complete dissolution, industrial isopropanol 315 g was added, an aqueous alcohol solution ① was prepared, and the pH of the solution was measured; aluminum chloride hexahydrate (1.33 moles, 321.9 g) was dissolved in 1466 g water to prepare a metal salt solution ②; dispersing aluminum hydroxide (0.33 mol, 26 g) in 94 g water, adding 9.4 g industrial isopropanol, stirring and dispersing uniformly to prepare a suspension ③; the solution ① and the solution ② are added dropwise at the same time to start the reaction, the stirring speed of the reaction system is 400 rpm, the reaction temperature is 75 ℃, the dropwise addition of the solution ① and the solution ② in 1 h is completed, the heat-preserving reaction is continued for 1.5: 1.5 h until the precipitation is complete, then the prepared suspension ③ is slowly poured into a reaction container to complete the acid-base neutralization reaction, the heat-preserving reaction is carried out for 2 hours until the precipitation is complete, and the reaction completion degree is detected according to the pH value and the ion concentration of the solution. And after the reaction is finished, filtering out a precipitate while the precipitate is hot, washing the precipitate with hot water until the filtrate meets the requirement, and putting the precipitate into a 130-DEG oven for drying after the washing is finished, thus obtaining the finished product 740 g. The yield was about 93.6%.
Measuring the particle size of the product: d10 1.066 μm, D50.57 μm, D95.15.47 μm, D100.45 μm;
product bulk density was measured: 0.31 g/ml;
the particle size diagram of the product is shown in figure 2.
Example 3
Diethyl phosphinic acid (2.05 mol,250.5 g, self-made) and diethyl phosphinic acid potassium (8 mol,1282.3 g, self-made) are dissolved in 6482 g pure water, after complete dissolution, industrial methanol 500 g is added, an aqueous alcohol solution ① is prepared, and the pH of the solution is determined to be 3.5; aluminum sulfate octadeca hydrate (1.33 mol,888 g) was dissolved in 4045 g water to prepare a metal salt solution ②; dispersing aluminum hydroxide (0.68 mol, 26 g) in 218 g water, adding industrial anhydrous methanol 24 g, stirring and dispersing uniformly to prepare suspension ③; and (3) simultaneously dropwise adding the solution ① and the solution ② to start the reaction, wherein the stirring speed of a reaction system is 200 rpm, the reaction temperature is 70 ℃, dropwise adding the solution ① and the solution ② in 1h is completed, the heat-preserving reaction is continued for 1h until the precipitation is complete, then the prepared suspension ③ is slowly poured into a reaction container to complete the acid-base neutralization reaction, the heat-preserving reaction is carried out for 2h until the precipitation is complete, and the reaction completion degree is detected according to the pH value and the ion concentration of the solution. And after the reaction is finished, filtering out a precipitate while the precipitate is hot, washing the precipitate with hot water until the filtrate meets the requirement, namely, washing is finished, and putting the precipitate into a 130-DEG oven for drying to obtain a finished product 1240 g. The yield was about 95.3%.
Measuring the particle size of the product: d10 1.01 μm, D50.49 μm, D95.12.45 μm, D100.58 μm;
Product bulk density was measured: 0.29 g/ml;
The particle size diagram of the product is shown in figure 3.
Example 4
Diisobutylphosphinic acid (1.05 mol,186.9 g, homemade) and sodium diisobutylphosphinate (5 mol,1000 g, homemade) are dissolved in 4373 g pure water, after complete dissolution, industrial ethanol 374 g is added, an aqueous alcohol solution ① is prepared, and the pH of the solution is measured; zinc sulfate heptahydrate (2.5 mol,718.8 g) was dissolved in 2875 g water to prepare a metal salt solution ②; zinc hydroxide (0.525 mol, 52.18 g) is dispersed in 188 and g water, and then industrial absolute ethyl alcohol 20 g is added, and the mixture is stirred and dispersed uniformly to prepare a suspension ③; the solution ① and the solution ② are added dropwise at the same time to start the reaction, the stirring speed of the reaction system is 300 rpm, the reaction temperature is 80 ℃, the dropwise addition of the solution ① and the solution ② is completed within 1.5 hours, the heat preservation reaction is continued for 1 hour until the precipitation is complete, then the prepared suspension ③ is slowly poured into a reaction container to complete the acid-base neutralization reaction, the heat preservation reaction is carried out for 2 hours until the precipitation is complete, and the reaction completion degree is detected according to the pH value and the ion concentration of the solution. And after the reaction is finished, filtering out a precipitate while the precipitate is hot, washing with cold water until the filtrate meets the requirement, namely, washing is finished, and putting the filtrate into a 130-DEG oven for drying to obtain a finished product 1158 g. The yield was about 92.0%.
Measuring the particle size of the product: d10 1.21 μm, D50.62 μm, D95.12.75 μm, D100.21 μm;
product bulk density was measured: 0.31 g/ml.
Example 5
Diisobutylphosphinic acid (1.55 mol,275.9 g, self-made) and sodium diisobutylphosphinate (6 mol,1200 g, self-made) are dissolved in 5351 g pure water, after complete dissolution, propanol 550 g is added, an aqueous alcohol solution ① is prepared, and the pH of the solution is measured; magnesium sulfate heptahydrate (3 mol,739.4 g) was dissolved in 2957 g water to prepare a metal salt solution ②; magnesium hydroxide (0.775 mol, 45.2 g) is dispersed in 162-g water, then propanol 18-g is added, and the mixture is stirred and dispersed uniformly to prepare a suspension ③; the solution ① and the solution ② are added dropwise at the same time to start the reaction, the stirring speed of a reaction system is 300 rpm, the reaction temperature is 80 ℃, the dropwise addition of the solution ① and the solution ② in 1 h is completed, the heat-preserving reaction is continued for 1.5: 1.5 h until the precipitation is complete, then the prepared suspension ③ is slowly poured into a reaction container to complete the acid-base neutralization reaction, the heat-preserving reaction is 2: 2h until the precipitation is complete, and the reaction completion degree is detected according to the pH value and the ion concentration of the solution. And after the reaction is finished, filtering out a precipitate while the precipitate is hot, washing with cold water until the filtrate meets the requirement, namely, washing is finished, and putting the filtrate into a 130-DEG oven for drying to obtain a finished product 1050 g. The yield was about 92.5%.
Measuring the particle size of the product: d10 1.24 μm, D50.91 μm, D95.41 μm, D100.46 μm;
product bulk density was measured: 0.32 g/ml.
From the above examples, it can be seen that the process of the present invention overcomes the disadvantages of metathesis and acid-base neutralization reactions and produces a dialkyl phosphinate product of high quality, narrow particle size distribution and low swelling.
Claims (10)
1. A preparation method of dialkyl phosphinate with fine particle size is characterized in that:
Step one: dissolving dialkylphosphinic acid and alkali metal dialkylphosphinate salt selected from sodium or potassium in a solvent to prepare a solution ①, wherein the alkyl group is selected from C1-C6 alkyl;
Step two: dissolving a metal salt in water to prepare a solution ②, wherein the metal salt is selected from soluble aluminum salt, zinc salt, magnesium salt and calcium salt;
Step three: dispersing an alkaline substance in a solvent to prepare a suspension ③, wherein the alkaline substance is selected from hydroxide or oxide of magnesium, aluminum, zinc, calcium or barium;
Step four: fully mixing the solution ① and the solution ② to start double decomposition reaction until precipitation is complete, and slowly adding the suspension ③ to complete acid-base neutralization reaction;
Step five: separating and purifying the precipitate to obtain the dialkylphosphinate;
The molar ratio of the alkali metal dialkylphosphinate in the solution ① to the metal salt in the solution ② is 1:2-6, and the molar ratio of the dialkylphosphinic acid in the solution ① to the alkaline substance in the solution ③ is 1:2-3;
The reaction of the method is carried out in an alcohol polar solvent-water system.
2. The method of claim 1, wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.
3. The method of claim 1, wherein the soluble aluminum, magnesium, and calcium salts are selected from the group consisting of chloride, sulfate, nitrate, and acetate salts of the above metals.
4. The method of claim 1, wherein the ratio of dialkylphosphinic acid to alkali metal dialkylphosphinate in the solution ① is 1:1-10.
5. The method of claim 1, wherein the concentration of solids in the solution ② is 10-50%.
6. The method of claim 1, wherein the concentration of solids in the suspension ③ is 10-50%.
7. The method according to claim 1, wherein in the fourth step, the reaction is started by adding the solution ① and the solution ② simultaneously, the precipitation reaction temperature is 50-90 degrees, the adding time of the solution ① and the solution ② is 1-5 hours, the reaction time is 1-6 hours after the addition is completed, and the precipitation is complete.
8. The method according to claim 1, wherein the solvent of at least one of the solution ① and the suspension ③ is an alcohol polar solvent or an alcohol polar solvent-water mixed solvent.
9. The method of claim 8, wherein the solution ① is an alcohol polar solvent-water solution, the solution ② is an aqueous solution, and the suspension ③ is an alcohol polar solvent-water suspension.
10. The method of claim 8, wherein the polar alcohol solvent is methanol, ethanol or propanol.
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| CN102746334A (en) * | 2012-07-13 | 2012-10-24 | 南开大学 | Preparation method of diisobutyl phosphinic acid aluminum |
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| DE10359815A1 (en) * | 2003-12-19 | 2005-07-28 | Clariant Gmbh | Process for the preparation of dialkylphosphinic salts |
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