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
- 150000003003 phosphines Chemical class 0.000 title 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- -1 naphtha Chemical compound 0.000 abstract 4
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 150000005840 aryl radicals Chemical class 0.000 abstract 3
- 239000000446 fuel Substances 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 235000010290 biphenyl Nutrition 0.000 abstract 2
- 239000004305 biphenyl Substances 0.000 abstract 2
- 125000006267 biphenyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 abstract 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- LAIZULYZLIEMOR-UHFFFAOYSA-N 1-phosphorosooctane Chemical compound CCCCCCCCP=O LAIZULYZLIEMOR-UHFFFAOYSA-N 0.000 abstract 1
- 101100305864 Alteromonas mediterranea (strain DSM 17117 / CIP 110805 / LMG 28347 / Deep ecotype) rph2 gene Proteins 0.000 abstract 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 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 101100135363 Yarrowia lipolytica (strain CLIB 122 / E 150) RIM101 gene Proteins 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- HUTDDBSSHVOYJR-UHFFFAOYSA-H bis[(2-oxo-1,3,2$l^{5},4$l^{2}-dioxaphosphaplumbetan-2-yl)oxy]lead Chemical compound [Pb+2].[Pb+2].[Pb+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O HUTDDBSSHVOYJR-UHFFFAOYSA-H 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- SWMBQMGPRYJSCI-UHFFFAOYSA-N octylphosphane Chemical compound CCCCCCCCP SWMBQMGPRYJSCI-UHFFFAOYSA-N 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- 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)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (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 |
|---|---|---|---|
| US4914960A | 1960-08-12 | 1960-08-12 | |
| US4914760A | 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 BE BE607168A patent/BE607168A/en unknown
- 1961-08-11 GB GB2903961A patent/GB965266A/en not_active Expired
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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