GB894152A - New phosphorus-nitrilo compounds - Google Patents
New phosphorus-nitrilo compoundsInfo
- Publication number
- GB894152A GB894152A GB81359A GB81359A GB894152A GB 894152 A GB894152 A GB 894152A GB 81359 A GB81359 A GB 81359A GB 81359 A GB81359 A GB 81359A GB 894152 A GB894152 A GB 894152A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amine
- mixture
- formula
- branched chain
- compounds
- 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
- 150000001412 amines Chemical class 0.000 abstract 10
- 239000000203 mixture Substances 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000000470 constituent Substances 0.000 abstract 2
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical class CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 abstract 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- RVFBZLFHKFSPRE-UHFFFAOYSA-N N(Cl)(Cl)Cl.[P] Chemical compound N(Cl)(Cl)Cl.[P] RVFBZLFHKFSPRE-UHFFFAOYSA-N 0.000 abstract 1
- 238000005576 amination reaction Methods 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000003729 cation exchange resin Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000012263 liquid product Substances 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000013638 trimer Substances 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
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 comprises amine derivatives of phosphorus-nitrilo compounds of the formula PnNnX2n in which n is at least 3 at least one of the constituents X has the structure NR1R2 in which R1 is a branched chain alkyl group or a branched chain aralkyl group and R2 is either hydrogen or an alkyl or aralkyl group and any of the radicals X which do not have the said structure NR1R2 are halogen atoms, e.g. chlorine atoms. Preferred compounds are those of the formula PnNn(NR1R2)2n and particularly those in which n is 3. The compounds may be obtained by reacting a compound of the formula PnNnX2n in which n is at least 3 and X is a halogen atom, preferably chlorine with an amine of the formula NHR1R2 in which R1 and R2 are as defined above. The process may be effected at room temperature but an elevated temperature, e.g. about 80 DEG C. is preferred. An excess of the amine reactant is conveniently used and the reaction is preferably effected in the solution, e.g. in a solvent such as ether in which the amine hydrohalide formed is substantially insoluble, or in a solvent such as benzene in which the amine hydrohalide formed is moderately soluble. In the latter case the liquid product of the reaction may be passed through a column of a cation exchange resin to convert the amine hydrohalide to free amine and excess amine and solvent then distilled off to leave the desired product. An example is given for the production of the compound [PN(NHC13H27)2]3 from a mixture o branched chain isomeric tridecylamines (prepared as below) and phosphorus nitrilo chloride trimer. Products in which one or more of the X constituents are halogen atoms are produced by using the stoichiometric proportion of amine there being substantially no unreacted amine to be distilled off. The products are useful as heat stable and radiation resistant lubricants. The mixture of branched chain isomeric tridecylamines used above is obtained by oxonation of mixed isomeric propylene tetramers to yield a mixture of tridecanols branched at any point in the chain except the a -carbon atom, amination of the said mixture and distillation of the product to yield a mixture of boiling range 126 DEG C. to 134 DEG C./25 mm. Hg.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB81359A GB894152A (en) | 1959-01-08 | 1959-01-08 | New phosphorus-nitrilo compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB81359A GB894152A (en) | 1959-01-08 | 1959-01-08 | New phosphorus-nitrilo compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB894152A true GB894152A (en) | 1962-04-18 |
Family
ID=9710944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB81359A Expired GB894152A (en) | 1959-01-08 | 1959-01-08 | New phosphorus-nitrilo compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB894152A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3284185A (en) * | 1962-09-14 | 1966-11-08 | Koopman Harmannus | Method of defoliating plants |
| US3351456A (en) * | 1962-09-14 | 1967-11-07 | Philips Corp | Method of destroying undesired plant growth |
| US3392214A (en) * | 1964-03-02 | 1968-07-09 | Hooker Chemical Corp | Cyclotriphosphazatriene compounds and process for making same |
-
1959
- 1959-01-08 GB GB81359A patent/GB894152A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3284185A (en) * | 1962-09-14 | 1966-11-08 | Koopman Harmannus | Method of defoliating plants |
| US3351456A (en) * | 1962-09-14 | 1967-11-07 | Philips Corp | Method of destroying undesired plant growth |
| US3392214A (en) * | 1964-03-02 | 1968-07-09 | Hooker Chemical Corp | Cyclotriphosphazatriene compounds and process for making same |
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