GB992377A - Process for the production of phosphonitriles - Google Patents
Process for the production of phosphonitrilesInfo
- Publication number
- GB992377A GB992377A GB416/64A GB41664A GB992377A GB 992377 A GB992377 A GB 992377A GB 416/64 A GB416/64 A GB 416/64A GB 41664 A GB41664 A GB 41664A GB 992377 A GB992377 A GB 992377A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trimer
- tetramer
- solvent
- pentane
- nh4cl
- 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
- 238000000034 method Methods 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 8
- 239000013638 trimer Substances 0.000 abstract 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 6
- 239000002904 solvent Substances 0.000 abstract 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 5
- 235000019270 ammonium chloride Nutrition 0.000 abstract 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 3
- 238000000605 extraction Methods 0.000 abstract 3
- 238000001640 fractional crystallisation Methods 0.000 abstract 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000002245 particle Substances 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 238000000746 purification Methods 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 229910052786 argon Inorganic materials 0.000 abstract 1
- DNKYMRIVXIQCFO-UHFFFAOYSA-N benzene pentane Chemical compound CCCCC.CCCCC.C1=CC=CC=C1 DNKYMRIVXIQCFO-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 abstract 1
- LFHISGNCFUNFFM-UHFFFAOYSA-N chloropicrin Chemical compound [O-][N+](=O)C(Cl)(Cl)Cl LFHISGNCFUNFFM-UHFFFAOYSA-N 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 229920005565 cyclic polymer Polymers 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 239000001307 helium Substances 0.000 abstract 1
- 229910052734 helium Inorganic materials 0.000 abstract 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000000779 smoke Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- JRJVWTRZBBWEDZ-UHFFFAOYSA-N tetrachloro(phenyl)-$l^{5}-phosphane Chemical compound ClP(Cl)(Cl)(Cl)C1=CC=CC=C1 JRJVWTRZBBWEDZ-UHFFFAOYSA-N 0.000 abstract 1
- 229950011008 tetrachloroethylene Drugs 0.000 abstract 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
- C07F9/6581—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 nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65814—Cyclic phosphazenes [P=N-]n, n>=3 n = 3 or 4
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/025—Polyphosphazenes
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
2,4,6 - Trichloro - 2,4,6 - triphenyltriphosphonitrile, and 2,4,6,8 - tetrachloro - 2,4,6,8 - tetraphenyl tetraphosphonitrile, of the respective formulae <FORM:0992377/C2/1> and <FORM:0992377/C2/2> where #f represents phenyl, are prepared by reacting phenyltetrachlorophosphorane with solid NH4Cl of particle size below 10m , in an inert solvent for the phosphorane, at 60-140 DEG C. Suitable solvents are hydrocarbons or halogenated hydrocarbons of boiling-point at least 60 DEG C. (e.g. n-heptane, CCl4, tetrachloroethylene, chlorobenzene, or chloropicrin) and preferred quantities of reactants are 0.1 to 1 mol. of NH4Cl/litre of solvent to less than 0.02 mols. of phosphorane/litre of solvent. The NH4Cl is suspended in the solvent, suitably by passing HCl and NH3 into it simultaneously, or passing in a smoke of NH4Cl in an inert gas (e.g. N2, argon or helium), to give a dispersion of particles of size between 1m and 10m . The phosphorane is suitably added to the refluxing suspension at such a rate as to maintain the desired reactant concentration. The trimer and tetramer formed may be separated by: (a) fractional crystallization from suitable solvent pairs (e.g. benzene-pentane or CHCl3-hexane), after purification of the reaction products by extraction at 60-140 DEG C. with a mixture of water and a solvent for the trimer and tetramer that itself has an aqueous solubility below 1% (e.g. n-heptane, hexane, pentane, CCl4, or benzene), when the water hydrolyses higher linear polymers to water-soluble products, and the trimer and tetramer are taken up in the non-aqueous phase; (b) by continuous extraction of the purified trimer-tetramer mixture with an aliphatic hydrocarbon of up to six contiguous carbon atoms, boiling below about 90 DEG C. (e.g. pentane, or hexane), when the trimer is extracted first. Cis and trans forms of the trimer may be separated by fractional crystallization from benzene, the cis form crystallizing first as a lesser soluble benzene adduct. Examples are given for the preparation of the trimer and tetramer in (1) chlorobenzene at various reaction temperatures; (2) chlorobenzene, using granular NH4Cl as a comparison; (3) heptane; also for purification of the reaction mixture by the above hydrolytic process; separation of the trimer-tetramer by (a) crystallization from chlorobenaene, followed by recrystallization from chloraform-pentane; (b) continuous extraction with pentane; separation of the cis and trans trimers by fractional crystallization from benzene. The cyclic polymers are useful for the preparation of thermally stable polymers by ammoniation and condensation at temperatures above 200 DEG C. Specification 981,821 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27826563A | 1963-05-06 | 1963-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB992377A true GB992377A (en) | 1965-05-19 |
Family
ID=23064332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB416/64A Expired GB992377A (en) | 1963-05-06 | 1964-01-03 | Process for the production of phosphonitriles |
Country Status (2)
| Country | Link |
|---|---|
| DE (2) | DE1242227B (en) |
| GB (1) | GB992377A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023239321A1 (en) * | 2022-06-06 | 2023-12-14 | Sallanti Ali | Low density ammonium nitrate production method in granular form |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6038307A (en) * | 1983-08-11 | 1985-02-27 | Nippon Daigaku | Composite material for plugging |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB905314A (en) * | 1958-04-25 | 1962-09-05 | Albright & Wilson Mfg Ltd | The production of cyclic phosphonitrilic chloride polymers |
-
1964
- 1964-01-03 GB GB416/64A patent/GB992377A/en not_active Expired
- 1964-02-26 DE DEG43249A patent/DE1242227B/en active Pending
- 1964-02-26 DE DEG39946A patent/DE1223382B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023239321A1 (en) * | 2022-06-06 | 2023-12-14 | Sallanti Ali | Low density ammonium nitrate production method in granular form |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1242227B (en) | 1967-06-15 |
| DE1223382B (en) | 1966-08-25 |
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