GB804141A - Phosphorus-containing esters containing sulphone groups and a process for their production - Google Patents
Phosphorus-containing esters containing sulphone groups and a process for their productionInfo
- Publication number
- GB804141A GB804141A GB25427/55A GB2542755A GB804141A GB 804141 A GB804141 A GB 804141A GB 25427/55 A GB25427/55 A GB 25427/55A GB 2542755 A GB2542755 A GB 2542755A GB 804141 A GB804141 A GB 804141A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- sulphonyl
- diethyl ester
- acid diethyl
- ester
- 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 4
- 150000002148 esters Chemical class 0.000 title abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- 125000001174 sulfone group Chemical group 0.000 title 1
- -1 aliphatic radical Chemical class 0.000 abstract 5
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- FZAJEGWDPOYEEC-UHFFFAOYSA-N 1-[ethoxy(ethylsulfonylmethyl)phosphoryl]oxyethane Chemical compound CCOP(=O)(OCC)CS(=O)(=O)CC FZAJEGWDPOYEEC-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 239000003791 organic solvent mixture Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract 1
- 239000012286 potassium permanganate Substances 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003021 water soluble solvent Substances 0.000 abstract 1
Classifications
-
- 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
-
- 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- 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
- C10M2223/047—Thioderivatives not containing metallic elements
-
- 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
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (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)
Abstract
The invention comprises compounds of the general formula <FORM:0804141/IV (b)/1> wherein R, R1 and R2 each represents a lower aliphatic radical having from 1 to 4 carbon atoms and n is an integer from 1-4 and a process for the production of compounds of the general formula <FORM:0804141/IV (b)/2> in which R represents an alkyl, aralkyl or aryl radical, n is an integer from 1 to 4, X represents an oxygen or sulphur atom or a direct C-P bond and Y represents an oxygen atom or X represents an oxygen or sulphur atom and Y represents a sulphur atom, and R1 and R2 represent lower alkyl radicals containing from 1 to 4 carbon atoms which comprises oxidizing an ester of the general formula <FORM:0804141/IV (b)/3> in which R, n, X, Y, R1 and R2 have the meanings given last above, in an aqueous solution with an alkali metal permanganate in the presence of such an amount of an acid that a substantially neutral solution is obtained after the oxidation. Where the thioether starting materials are sparingly soluble in water aqueous dioxane or acetone, suitable organic water-soluble solvents or aqueous organic solvent mixtures may be employed as reaction medium. In examples, b -ethyl-sulphonyl-ethyl phosphonic acid diethyl ester is obtained by dropping b -ethyl mercapto-ethyl phosphonic acid diethyl ester into aqueous potassium permanganate solution acidified with sulphuric acid (1); similarly are obtained ethyl-sulphonyl-methyl phosphonic acid diethyl ester (2); b -ethyl sulphonyl-ethyl phosphorothiolic acid diethyl ester (3); ethyl-sulphonyl-methyl-phosphorothiolic acid diethyl ester (4), ethyl-sulphonyl-ethyl-phosphorothiolic acid dimethyl ester (5), phenyl - sulphonyl - ethyl - phosphorothiolic acid diethyl ester (6), b -ethyl-sulphonyl ethyl phosphoric acid diethyl ester (7) and b -ethyl-sulphonyl-ethyl-phosphorothionic acid diethyl ester are obtained by similar processes for oxidizing the corresponding thio ether esters. Additional compounds prepared by analogous processes from the corresponding thioether esters are b -methyl and b -ethyl-sulphonyl-ethyl phosphorothionothiolic dimethyl esters, b -ethyl-sulphonyl-ethyl phosphorothiono-thiolic diethyl ester and b -ethyl-sulphonyl-methyl-phosphorothionothiolic dimethyl ester. Starting materials of the kind defined above in which X represents a direct C-P bond may be obtained by reacting chloroalkyl alkyl thioethers with sodium dialkyl phosphites. Specification 697,120 and German Specifications 786,692, 830,509, 871,448 and 876,691 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE804141X | 1954-09-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB804141A true GB804141A (en) | 1958-11-12 |
Family
ID=6722046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25427/55A Expired GB804141A (en) | 1954-09-04 | 1955-09-05 | Phosphorus-containing esters containing sulphone groups and a process for their production |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB804141A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3112268A (en) * | 1960-02-15 | 1963-11-26 | Shell Oil Co | Lubricating oil composition |
| US3112269A (en) * | 1960-12-23 | 1963-11-26 | Shell Oil Co | Lubricating compositions containing sulfoxy alkyl phosphono compounds |
| US3112271A (en) * | 1959-04-13 | 1963-11-26 | Shell Oil Co | Liquid hydrocarbon composition |
| US3126314A (en) * | 1961-10-18 | 1964-03-24 | S-chlorophenylsblfonylmethyl - o | |
| US3161596A (en) * | 1959-12-14 | 1964-12-15 | Shell Oil Co | Liquid lubricant composition |
| US4090959A (en) * | 1974-01-07 | 1978-05-23 | Hooker Chemicals & Plastics Corp. | Process for sequestering metal ions |
| US5550276A (en) * | 1990-01-18 | 1996-08-27 | Ciba-Geigy Corporation | Phosphonic acid derivatives and thionophosphonic acid derivatives |
-
1955
- 1955-09-05 GB GB25427/55A patent/GB804141A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3112271A (en) * | 1959-04-13 | 1963-11-26 | Shell Oil Co | Liquid hydrocarbon composition |
| US3161596A (en) * | 1959-12-14 | 1964-12-15 | Shell Oil Co | Liquid lubricant composition |
| US3112268A (en) * | 1960-02-15 | 1963-11-26 | Shell Oil Co | Lubricating oil composition |
| US3112269A (en) * | 1960-12-23 | 1963-11-26 | Shell Oil Co | Lubricating compositions containing sulfoxy alkyl phosphono compounds |
| US3126314A (en) * | 1961-10-18 | 1964-03-24 | S-chlorophenylsblfonylmethyl - o | |
| US4090959A (en) * | 1974-01-07 | 1978-05-23 | Hooker Chemicals & Plastics Corp. | Process for sequestering metal ions |
| US5550276A (en) * | 1990-01-18 | 1996-08-27 | Ciba-Geigy Corporation | Phosphonic acid derivatives and thionophosphonic acid derivatives |
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