CA1145114A - Method of purifying cyclic dichlorophosphazenes containing trace amounts of protic impurities - Google Patents
Method of purifying cyclic dichlorophosphazenes containing trace amounts of protic impuritiesInfo
- Publication number
- CA1145114A CA1145114A CA000384499A CA384499A CA1145114A CA 1145114 A CA1145114 A CA 1145114A CA 000384499 A CA000384499 A CA 000384499A CA 384499 A CA384499 A CA 384499A CA 1145114 A CA1145114 A CA 1145114A
- Authority
- CA
- Canada
- Prior art keywords
- cyclic
- boron trihalide
- reactor
- protic impurities
- dichlorophosphazene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 78
- 239000012535 impurity Substances 0.000 title claims abstract description 62
- 238000000034 method Methods 0.000 title claims description 53
- 229910052796 boron Inorganic materials 0.000 claims abstract description 66
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 65
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 37
- 239000013638 trimer Substances 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 40
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical group ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 21
- 239000011261 inert gas Substances 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 7
- 229910015844 BCl3 Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229920002632 poly(dichlorophosphazene) polymer Polymers 0.000 claims description 6
- 238000010926 purge Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 238000013019 agitation Methods 0.000 claims description 2
- 230000006872 improvement Effects 0.000 claims description 2
- 230000000977 initiatory effect Effects 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- -1 phosphorus compound Chemical class 0.000 claims description 2
- 239000002685 polymerization catalyst Substances 0.000 claims 2
- 229910001868 water Inorganic materials 0.000 abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 34
- 230000003197 catalytic effect Effects 0.000 abstract description 6
- 239000003054 catalyst Substances 0.000 description 48
- 230000008569 process Effects 0.000 description 14
- 239000007789 gas Substances 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- UNSWOJJUGYZOQV-UHFFFAOYSA-N trichloroborane;triphenyl phosphate Chemical compound ClB(Cl)Cl.C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 UNSWOJJUGYZOQV-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910000619 316 stainless steel Inorganic materials 0.000 description 2
- 239000003341 Bronsted base Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000004457 water analysis Methods 0.000 description 2
- IOZVKDXPBWBUKY-LQIBPGRFSA-N (1E,4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one Chemical compound C1=CC(OC)=CC=C1\C=C\C(=O)\C=C\C1=CC=C(OC)C=C1 IOZVKDXPBWBUKY-LQIBPGRFSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 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 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum 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
- 230000037048 polymerization activity Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/097—Compounds containing nitrogen and non-metals and optionally metals containing phosphorus atoms
- C01B21/098—Phosphonitrilic dihalides; Polymers thereof
- C01B21/0986—Phosphonitrilic dichlorides; Polymers thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/181,028 US4327063A (en) | 1980-08-25 | 1980-08-25 | Method of purifying cyclic dichlorophosphazenes containing trace amounts of protic impurities |
| US181,028 | 1980-08-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1145114A true CA1145114A (en) | 1983-04-26 |
Family
ID=22662602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000384499A Expired CA1145114A (en) | 1980-08-25 | 1981-08-24 | Method of purifying cyclic dichlorophosphazenes containing trace amounts of protic impurities |
Country Status (5)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3144751A1 (de) * | 1981-11-11 | 1983-05-19 | Hoechst Ag, 6230 Frankfurt | Verfahren zur reinigung von cyclischen chlorphosphazenen |
| US4544537A (en) * | 1984-12-17 | 1985-10-01 | The Firestone Tire & Rubber Company | Method for purifying cyclic dichlorophosphazene trimer of catalytic impurities |
| US4867957A (en) * | 1988-04-11 | 1989-09-19 | The United States Of America As Represented By The Secretary Of The Army | Process for making polyphosphazenes |
| IL95939A0 (en) * | 1989-10-20 | 1991-07-18 | Atochem | Process for compensating the harmful effects of impurities of n-dichlorophosphoryltrichlorophosphazene and its polycondensation product |
| FR2681061B1 (fr) * | 1991-09-11 | 1993-11-19 | Atochem | Procede de preparation de polydichlorophosphazenes a partir d'une composition precurseur a base d'hexachlorocyclotriphosphazene. |
| DE4221854A1 (de) * | 1992-07-03 | 1994-01-05 | Nuenchritz Chemie Gmbh | Phosphornitridchloride enthaltende Zusammensetzungen und Verfahren zu deren Herstellung |
| FR2697008B1 (fr) * | 1992-10-15 | 1994-12-09 | Elf Atochem | Procédé pour remédier à l'action de l'eau sur les polydichlorophosphazènes. |
| JP4837963B2 (ja) * | 2005-09-20 | 2011-12-14 | 濱中ナット株式会社 | ねじの弛み止め構造 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3952086A (en) * | 1974-10-07 | 1976-04-20 | The Firestone Tire & Rubber Company | Purification of crude chlorophosphazene compounds by treatment with Bronsted bases |
| NL173509C (nl) * | 1975-08-22 | 1984-02-01 | Firestone Tire & Rubber Co | Werkwijze voor het polymeriseren van cyclische fosfazenen. |
| JPS537100A (en) * | 1976-07-09 | 1978-01-23 | Hitachi Ltd | System for setting magnetic moment of artificial satellite |
| US4116891A (en) * | 1976-12-06 | 1978-09-26 | Armstrong Cork Company | Catalytic process for the preparation of phosphazene polymers |
| US4175113A (en) * | 1978-04-20 | 1979-11-20 | The Firestone Tire & Rubber Company | Purification of crude chlorophosphazene compounds by treatment with water |
| US4226840A (en) * | 1979-09-19 | 1980-10-07 | The Firestone Tire & Rubber Company | Process for the polymerization of cyclic polyhalophosphazenes using a catalyst composition of boron trihalide and oxygenated phosphorus compounds |
-
1980
- 1980-08-25 US US06/181,028 patent/US4327063A/en not_active Expired - Lifetime
-
1981
- 1981-08-21 EP EP81106526A patent/EP0046584B1/en not_active Expired
- 1981-08-21 DE DE8181106526T patent/DE3161594D1/de not_active Expired
- 1981-08-24 CA CA000384499A patent/CA1145114A/en not_active Expired
- 1981-08-25 JP JP56132234A patent/JPS5945602B2/ja not_active Expired
-
1984
- 1984-06-06 JP JP59114688A patent/JPS6027609A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0046584B1 (en) | 1983-12-07 |
| JPS5945602B2 (ja) | 1984-11-07 |
| EP0046584A1 (en) | 1982-03-03 |
| JPS6027609A (ja) | 1985-02-12 |
| DE3161594D1 (en) | 1984-01-12 |
| US4327063A (en) | 1982-04-27 |
| JPS5771808A (en) | 1982-05-04 |
| JPS623085B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-01-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |