GB965266A - New organic phosphines and their preparation - Google Patents
New organic phosphines and their preparationInfo
- Publication number
- GB965266A GB965266A GB2903961A GB2903961A GB965266A GB 965266 A GB965266 A GB 965266A GB 2903961 A GB2903961 A GB 2903961A GB 2903961 A GB2903961 A GB 2903961A GB 965266 A GB965266 A GB 965266A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cycloalkyl
- cyclotetraphosphines
- phosphine
- alkyl
- reacting
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/26—Organic compounds containing phosphorus
- C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
-
- 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
- C07F9/50—Organo-phosphines
- C07F9/504—Organo-phosphines containing a P-P bond
-
- 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
- C07F9/6568—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 atoms as the only ring hetero atoms
- C07F9/65683—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 atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
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)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
Abstract
The invention comprises cyclotetraphosphines of the general formula: <FORM:0965266/C1/1> wherein each R is the same or different alkyl, cycloalkyl, alkenyl or aryl radical. The compounds in which R is alkyl, cycloalkyl, or aryl may be obtained (a) by heating at from 50 DEG C. to 100 DEG C. in an inert atmosphere one or more primary phosphine oxides of the formula R.P(O)H2 wherein R is an alkyl, cycloalkyl or aryl radical, (b) by reacting at from 25 DEG C. to 100 DEG C. in an inert organic solvent a phosphine of the formula RPH2 with a dihalophosphine of the formula RP(Halogen)2 wherein R is alkyl, cycloalkyl or aryl or (c) by reacting the above specified dihalophosphine RP(Halogen)2 at from -80 DEG C. to + 100 DEG C. with a reducing metal, e.g. sodium, potassium, lithium or magnesium. The products in which R is an alkenyl group may be obtained by reacting phosphorus pentachloride with an a -olefin and then removing hydrochloric acid from the product by treatment with a base. Suitable inert organic solvents for method (b) above and which may also be present in the other defined reactions are benzene, toluene, xylene, naphtha, hexane, ether, dioxane, tetrahydrofuran, and the dimethyl ether of diethylene glycol. Several examples are given and the products are useful as additives for motor fuels (see Division C5). The primary phosphine oxides used as starting materials may be obtained by reacting a ketone with phosphine in the presence of a mineral acid, e.g. hydrochloric acid, sulphuric acid or phosphoric acid or by oxidising a primary phosphine in a polar solvent, e.g. alcohol, at a temperature not exceeding 0 DEG C., thus octyl phosphine may be converted to octylphosphine oxide by treating it with 30% aqueous hydrogen peroxide at 0 DEG C. in alcohol.ALSO:A motor fuel comprises gasoline, tetraethyl lead in an amount sufficient to impart anti-knock properties to the fuel and from about 5% to about 200% by weight of the amount theoretically required to convert all the tetraethyl lead to lead orthophosphate of one or more cyclotetraphosphines of the general formula <FORM:0965266/C4-C5/1> wherein each R is the same or different alkyl, cycloalkyl, alkenyl or aryl radical (see Division C2). Specified cyclotetraphosphines used in the examples given are tetra 3-pentyl-, tetra n-octyl-, tetramethyl, tetraphenyl-, tetracyclohexyl-, tetrabutenyl-, diphenyl di-n-octyl-, diphenyl diisobutyl-, and diethyl dicyclohexyl cyclotetraphosphines. The cyclic phosphines are stated to suppress pre-ignition to a significant extent.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4914760A | 1960-08-12 | 1960-08-12 | |
| US4914960A | 1960-08-12 | 1960-08-12 | |
| US114643A US3032591A (en) | 1961-06-05 | 1961-06-05 | Substituted cyclotetraphosphines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB965266A true GB965266A (en) | 1964-07-29 |
Family
ID=27367488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2903961A Expired GB965266A (en) | 1960-08-12 | 1961-08-11 | New organic phosphines and their preparation |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE607168A (en) |
| GB (1) | GB965266A (en) |
| NL (1) | NL268004A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2306478A (en) * | 1995-09-28 | 1997-05-07 | Clariant Finance Bvi Ltd | Substituted biphosphines and 3-12 membered cyclic phosphines, process for their preparation and their use as stabilising additives in polymer compositions |
-
0
- NL NL268004D patent/NL268004A/xx unknown
-
1961
- 1961-08-11 GB GB2903961A patent/GB965266A/en not_active Expired
- 1961-08-11 BE BE607168A patent/BE607168A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2306478A (en) * | 1995-09-28 | 1997-05-07 | Clariant Finance Bvi Ltd | Substituted biphosphines and 3-12 membered cyclic phosphines, process for their preparation and their use as stabilising additives in polymer compositions |
| GB2306478B (en) * | 1995-09-28 | 1998-12-09 | Clariant Finance Bvi Ltd | Phosphorus compounds |
| ES2152760A1 (en) * | 1995-09-28 | 2001-02-01 | Clariant Finance Bvi Ltd | Substituted biphosphines and 3-12 membered cyclic phosphines, process for their preparation and their use as stabilising additives in polymer compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| NL268004A (en) | |
| BE607168A (en) | 1962-02-12 |
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