GB791526A - Improvements in or relating to new dimethyl-(phenyl)-phosphates for use as fuel additives - Google Patents
Improvements in or relating to new dimethyl-(phenyl)-phosphates for use as fuel additivesInfo
- Publication number
- GB791526A GB791526A GB21446/55A GB2144655A GB791526A GB 791526 A GB791526 A GB 791526A GB 21446/55 A GB21446/55 A GB 21446/55A GB 2144655 A GB2144655 A GB 2144655A GB 791526 A GB791526 A GB 791526A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- phenyl
- chlorine
- compounds
- phosphates
- 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
- 229910019142 PO4 Inorganic materials 0.000 title abstract 5
- 239000002816 fuel additive Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 8
- 239000000446 fuel Substances 0.000 abstract 8
- 239000000460 chlorine Substances 0.000 abstract 6
- 229910052801 chlorine Inorganic materials 0.000 abstract 6
- 239000000654 additive Substances 0.000 abstract 5
- -1 p - tolyl Chemical group 0.000 abstract 5
- 239000000203 mixture Substances 0.000 abstract 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- CVNMBKFJYRAHPO-UHFFFAOYSA-N [chloro(methyl)phosphoryl]methane Chemical compound CP(C)(Cl)=O CVNMBKFJYRAHPO-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052794 bromium Chemical group 0.000 abstract 3
- 125000001246 bromo group Chemical group Br* 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 3
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical group CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 abstract 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 239000003350 kerosene Substances 0.000 abstract 2
- 239000010687 lubricating oil Substances 0.000 abstract 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- AAWYDKUOFDTBER-UHFFFAOYSA-N (3-chloro-2-methylphenyl) dihydrogen phosphate Chemical compound CC1=C(C=CC=C1Cl)OP(=O)(O)O AAWYDKUOFDTBER-UHFFFAOYSA-N 0.000 abstract 1
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 abstract 1
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 abstract 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 abstract 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 abstract 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- ZCIXEVMBAGQLKB-UHFFFAOYSA-N [4-(chloromethyl)phenyl] dihydrogen phosphate Chemical class OP(O)(=O)OC1=CC=C(CCl)C=C1 ZCIXEVMBAGQLKB-UHFFFAOYSA-N 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 239000006079 antiknock agent Substances 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- RLEMIFPVSKAYPE-UHFFFAOYSA-M bromo(triethyl)plumbane Chemical compound CC[Pb](Br)(CC)CC RLEMIFPVSKAYPE-UHFFFAOYSA-M 0.000 abstract 1
- 238000003442 catalytic alkylation reaction Methods 0.000 abstract 1
- 238000001833 catalytic reforming Methods 0.000 abstract 1
- 239000002131 composite material Substances 0.000 abstract 1
- VCJZTATVUDMNLU-UHFFFAOYSA-N dibromomethylbenzene Chemical class BrC(Br)C1=CC=CC=C1 VCJZTATVUDMNLU-UHFFFAOYSA-N 0.000 abstract 1
- OLOAJSHVLXNSQV-UHFFFAOYSA-N diethyl(dimethyl)plumbane Chemical compound CC[Pb](C)(C)CC OLOAJSHVLXNSQV-UHFFFAOYSA-N 0.000 abstract 1
- YLFBFPXKTIQSSY-UHFFFAOYSA-N dimethoxy(oxo)phosphanium Chemical compound CO[P+](=O)OC YLFBFPXKTIQSSY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- KHQJREYATBQBHY-UHFFFAOYSA-N ethyl(trimethyl)plumbane Chemical compound CC[Pb](C)(C)C KHQJREYATBQBHY-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 238000002407 reforming Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- XOOGZRUBTYCLHG-UHFFFAOYSA-N tetramethyllead Chemical group C[Pb](C)(C)C XOOGZRUBTYCLHG-UHFFFAOYSA-N 0.000 abstract 1
- WBJSMHDYLOJVKC-UHFFFAOYSA-N tetraphenyllead Chemical compound C1=CC=CC=C1[Pb](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WBJSMHDYLOJVKC-UHFFFAOYSA-N 0.000 abstract 1
- SMHNCYOTIYFOKL-UHFFFAOYSA-N tetrapropylplumbane Chemical compound CCC[Pb](CCC)(CCC)CCC SMHNCYOTIYFOKL-UHFFFAOYSA-N 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 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
- C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
- C10L1/2641—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) oxygen bonds only
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
The invention comprises dimethyl-(phenyl)-phosphates of formula <FORM:0791526/IV (b)/1> wherein X is chlorine or bromine, R, R1 and R11 are alkyl or haloalkyl radicals having 1 or 2 chlorine or bromine atoms, a, b, x, y and z are 0 or 1, at least one being 1, and the total number of carbon atoms in the R groups is not more than 6. The compounds may be prepared by reacting dimethyl phosphoryl chloride with the appropriate sodium phenoxide formed in aqueous solution. The dimethyl phosphoryl chloride may be obtained by reacting dimethyl hydrogen phosphite with chlorine gas. In examples: (1) dimethyl phosphoryl chloride prepared as described above was added to an aqueous solution of m-cresol in sodium hydroxide to give dimethyl-(m-tolyl)-phosphate; (2) the following compounds were prepared as in (1) using the appropriate substituted phenol:-dimethyl - (p - tolyl) - or - (3 : 5 - dimethylphenyl)- or -(p-ethylphenyl)- or -(m-sec.-butylphenyl)- or -(3 : 5-diethylphenyl)- or -(2 : 4 : 5-trimethylphenyl)- or -(2 : 4-di-n-propyl-phenyl)-or -(2 - methyl - 4 - isopropyl - 5 - ethylphenyl)-or -(o- or m- or p-chlorophenyl)- or -(o-bromophenyl)- or -(monochlorotolyl)- or -(4-chloro-3-methylphenyl)- or -(p-chloromethylphenyl)-phosphates. Further substituted phenol starting materials are specified and an extensive list of the compounds of the invention is given.ALSO:Dimethyl-(phenyl)-phosphates of formula <FORM:0791526/III/1> wherein X is chlorine or bromine, R, R1 and R11 are alkyl or haloalkyl radicals having 1 or 2 chlorine or bromine atoms, a, b, x, y and z are 0 or 1, at least one being 1, and the total number of carbon atoms in the R groups is not more than 6 (see Group IV (b)) are used as additives in liquid fuel compositions and lubricating oils. Specified fuels are gasoline stocks such as straight run or cracked fuels, or other fuels obtained by reforming, catalytic reforming or alkylation. When used in fuel compositions the compounds reduce deposit-induced autoignition. The compounds may be used in fuel compositions together with organolead antiknock agents such as tetramethyl-, tetraethyl-or tetrapropyl-lead, dimethyldiethyl-lead, trimethylethyl-lead, tetraphenyl-lead and triethyl-lead bromide. The fuel compositions may also contain organic halide scavengers such as trichlorobenzene and dibromotoluenes. The specified additives may be combined as composite additives together with a blending agent such as kerosene, dyes, antioxidants, rust-inhibitors, anti-icing agents, &c. The compounds may be used as additives to lubricating oils, in particular those have a viscosity from about 30 SUS. at 100 DEG F. to about 250 SUS. at 210 DEG F. In examples the following compounds of the invention were added to various gasoline fuel stocks: dimethyl- (o- or m-tolyl)- or -(p-ethylphenyl)- or -(p-chloro- or -bromophenyl)- or -(monochloro-tolyl)- or (3-chloro-2-methyl-phenyl)-phosphate. Other additives specified in the examples are tetraethyl-lead, ethylene dibromide, ethylene dichloride and kerosene.ALSO:Vinyl polymers, e.g. polyvinyl chloride, are plasticized with dimethyl-(phenyl-phosphates of formula: <FORM:0791526/IV (a)/1> wherein X is chlorine or bromine, R, R1 and R11 are alkyl or haloalkyl radicals having 1 or 2 chlorine or bromine atoms, a, b, x, y and z are 0 or 1, at least one being 1, and the total number of carbon atoms in the R groups is not more than 6 (see Group IV (b)). Many compounds of the above formula such as dimethyl-(m or p-tolyl) - or (3:5 - dimethylphenyl) - or (p-ethylphenyl) - or (m - sec. butyl - phenyl) - or (3:5 - diethylphenyl) - or (2 : 4 : 5 - trimethylphenyl) - or (2 : 4 - di - n - propyl - phenyl) - or (2 - methyl - 4 - isopropyl - 5 - ethylphenyl) - or (o -, m - or p - chlorophenyl) - or (o - bromophenyl) - or (monochlorotolyl) - or (4 - chloro-3 - methylphenyl) - or (p - chloromethylphenyl)-phosphates are specified.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US791526XA | 1954-07-26 | 1954-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB791526A true GB791526A (en) | 1958-03-05 |
Family
ID=22148765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21446/55A Expired GB791526A (en) | 1954-07-26 | 1955-07-25 | Improvements in or relating to new dimethyl-(phenyl)-phosphates for use as fuel additives |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1134156A (en) |
| GB (1) | GB791526A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3034877A (en) * | 1957-08-05 | 1962-05-15 | Exxon Research Engineering Co | Leaded gasolines |
| US3047372A (en) * | 1957-11-29 | 1962-07-31 | Exxon Research Engineering Co | Anti-knock gasoline |
| US3052528A (en) * | 1958-07-01 | 1962-09-04 | Shell Oil Co | Gasoline composition |
| US3007783A (en) * | 1958-11-18 | 1961-11-07 | Atlantic Refining Co | Motor fuel compositions |
| US3038791A (en) * | 1959-07-16 | 1962-06-12 | Ethyl Corp | Phenyl phosphate compositions |
| US3056667A (en) * | 1959-09-02 | 1962-10-02 | Sinclair Research Inc | Leaded gasoline containing phosphorus and phosphate |
-
1955
- 1955-07-25 GB GB21446/55A patent/GB791526A/en not_active Expired
- 1955-07-26 FR FR1134156D patent/FR1134156A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1134156A (en) | 1957-04-08 |
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