GB777718A - New organic compounds containing phosphorus and process for making them - Google Patents
New organic compounds containing phosphorus and process for making themInfo
- Publication number
- GB777718A GB777718A GB10897/54A GB1089754A GB777718A GB 777718 A GB777718 A GB 777718A GB 10897/54 A GB10897/54 A GB 10897/54A GB 1089754 A GB1089754 A GB 1089754A GB 777718 A GB777718 A GB 777718A
- Authority
- GB
- United Kingdom
- Prior art keywords
- groups
- formula
- products
- residues
- ethyl
- 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract 3
- 150000002894 organic compounds Chemical class 0.000 title abstract 3
- 239000011574 phosphorus Substances 0.000 title abstract 3
- 229910052698 phosphorus Inorganic materials 0.000 title abstract 3
- -1 2-butyloctyl Chemical group 0.000 abstract 12
- 150000001875 compounds Chemical class 0.000 abstract 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 7
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 6
- 125000001424 substituent group Chemical group 0.000 abstract 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 4
- 229910052783 alkali metal Inorganic materials 0.000 abstract 4
- 102000003914 Cholinesterases Human genes 0.000 abstract 3
- 108090000322 Cholinesterases Proteins 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 150000001340 alkali metals Chemical class 0.000 abstract 3
- 229940048961 cholinesterase Drugs 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 210000002966 serum Anatomy 0.000 abstract 3
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 241000607479 Yersinia pestis Species 0.000 abstract 2
- 239000013543 active substance Substances 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 230000002401 inhibitory effect Effects 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 229940125904 compound 1 Drugs 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 abstract 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 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
- C07F9/28—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
- C07F9/4025—Esters of poly(thio)phosphonic acids
- C07F9/404—Esters of poly(thio)phosphonic acids containing hydroxy substituents in the hydrocarbon radicals
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises as new products organic compounds containing phosphorus having the formula <FORM:0777718/IV(b)/1> in which R to R4 represent alkyl, cycloalkyl, aralkyl, aryl, or heterocyclic residues which may contain substituents, and etherified or esterified derivatives thereof. The alkyl residues may be straight or branched chain and may contain substituents, specified groups being methyl, ethyl, propyl, isopropyl, butyl, hexyl, 2-ethyl butyl, octyl, 2-butyloctyl, lauryl, octadecyl and 2-chloroethyl radicals, also alkyl groups substituted by thiocyano, cyano, or ester groups. The residues R to R4 may be the same or different. When they are aromatic residues they may be mononuclear or polynuclear and may contain nuclear substituents, specified aromatic residues being phenyl, 2- and 4-chlorophenyl, 2:4-dichlorophenyl, 4-methoxyphenyl, 4-nitrophenyl, naphthyl and 4-diphenyl groups. Other residues specified are benzyl, cyclohexyl, and tetrahydrofurfuryl. The products may be obtained by condensing a compound of the formula (R1O)(R2O)P(O).C(R)(O) with a compound of the formula H.P.(O)(OR3)(OR4) in the presence of an alkaline condensing agent, e.g. a tertiary amine such as triethylamine or tributylamine or an alkali metal or alkaline earth metal salt of a weak acid, e.g. potassium carbonate, barium acetate, or sodium acetate or an alkali metal alcoholate such as sodium methylate. Instead of using an alkaline condensing agent the compound H.P(O)(OR3)(OR4) may be used in the form of an alkali metal salt of the formula Me.P.(O)(OR3)(OR4) where Me is an alkali metal and the alcoholate first formed subsequently hydrolysed to the corresponding alcohol. The hydrolysis may be effected by passing a stream of humid air through the reaction mixture. When the radicals R1 to R4 are identical the products may be obtained by reacting two moles. of a compound of the formula (R1O)-(R2O)P(O)(Me where Me is a monovalent metal with one mole. of a carboxylic acid halide of the formula Hal.CO.R. and then hydrolysing the alcoholate first formed, e.g. with humid air, to the corresponding alcohol. The reactions may be carried out in an inert solvent, e.g. benzene, toluene, ether, dioxane, hexane, or low boiling benzine. Suitable reaction temperatures are 40-120 DEG C. and the products can be distilled off under reduced pressure. The hydroxyl group in the products may be converted to other groups, e.g. it may be esterified or etherified. Examples are given for the production of compounds of the above formula in which R1 to R4 are ethyl groups and (1) R is CH3; (2) R is -CH2.CH3; (3) R is C6H5 and the benzoyl ester of this product; (4) R is Cl.CH2-; (5) R is Cl2CH-; and (6) R is CCl3-. The product in which R1 to R4 are ethyl groups and R is CH3 is stated to have a strong inhibiting action on serum cholinesterase (see Group VI). It is stated that some of the products may be used as additives to lubricants and that some of the products can be incorporated as active substances in preparation for combating pests. The compounds of the formula (R1.O)(R2O)P(O).C(R)(O) may be obtained by reacting a compound of the formula (R1O)(R2O)P.OMe where Me is an atom of a monovalent metal with a carboxylic acid halide of the formula Hal-CO.R.ALSO:Some of the phosphorus-containing organic compounds corresponding to the general formula:- <FORM:0777718/VI/1> in which R to R4 represent alkyl, cycloalkyl, aralkyl, aryl, or heterocyclic residues which may contain substituents, and etherified or esterified derivatives thereof (see Group IVb) may be incorporated as active substances in preparations for p combating pests while others are stated to have utility in the pharmaceutical field, e.g. for inhibiting serum cholinesterase. The compound 1 : 1 - diphosphonic acid diethyl ester-ethanol, i.e. the compound of the above formula in which R1 to R4 are ethyl and R is CH3 on topical application to the eye strongly inhibits serum cholinesterase. The alkyl residues in the products may be straight or branched chain and may contain substituents, specified groups being methyl, ethyl, propyl, isopropyl, butyl, hexyl, 2 - ethyl butyl, octyl, 2 - butyloctyl, lauryl, octadecyl and 2 - chloroethyl radicals, also alkyl groups substituted by thiocyana, cyano, or ester groups. When the groups R to R4 are aromatic they may be mononuclear or polynuclear and may contain nuclear substituents, specified aromatic residues being phenyl, 2 - and - 4 - chlorophenyl, 2 : 4 - dichlorophenyl, 4 - methoxyphenyl, 4 - nitrophenyl, naphthyl and 4 - dipenyl groups. Other residues specified are benzyl, cyclohexyl, and tetra-hydrofurfuryl. Other products of the above general formula which are specified are those in which R1 to R4 are ethyl groups and (1) R - CH2, CH3; (2) R is C6 H5 and the benzoyl ester of this product; (3) R is Cl. CH2; (4) R is Cl2 CH-; and (5) is CCl3.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH777718X | 1953-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB777718A true GB777718A (en) | 1957-06-26 |
Family
ID=4535948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10897/54A Expired GB777718A (en) | 1953-04-20 | 1954-04-13 | New organic compounds containing phosphorus and process for making them |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB777718A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4141967A (en) | 1976-02-23 | 1979-02-27 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Cosmetic deodorant preparations containing alkane diphosphonic acid esters |
| US4254114A (en) * | 1979-01-02 | 1981-03-03 | The Proctor & Gamble Company | Control of pyrophosphate microorganisms with organophosphonates |
| US4268507A (en) * | 1979-02-13 | 1981-05-19 | Symphar S.A. | Monophosphonate compounds as hypoglycemic and/or antiartherogenic agents |
| US4416877A (en) | 1979-02-13 | 1983-11-22 | Symphar S.A. | Anti-atherosclerotic pharmaceutical compositions containing diphosphonate compounds |
| WO1996033199A1 (en) * | 1995-04-20 | 1996-10-24 | Merck & Co., Inc. | Process for making 1-hydroxybisphosphonates |
-
1954
- 1954-04-13 GB GB10897/54A patent/GB777718A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4141967A (en) | 1976-02-23 | 1979-02-27 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Cosmetic deodorant preparations containing alkane diphosphonic acid esters |
| US4254114A (en) * | 1979-01-02 | 1981-03-03 | The Proctor & Gamble Company | Control of pyrophosphate microorganisms with organophosphonates |
| US4268507A (en) * | 1979-02-13 | 1981-05-19 | Symphar S.A. | Monophosphonate compounds as hypoglycemic and/or antiartherogenic agents |
| US4416877A (en) | 1979-02-13 | 1983-11-22 | Symphar S.A. | Anti-atherosclerotic pharmaceutical compositions containing diphosphonate compounds |
| WO1996033199A1 (en) * | 1995-04-20 | 1996-10-24 | Merck & Co., Inc. | Process for making 1-hydroxybisphosphonates |
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