GB902802A - Organic dithiophosphinic compounds and the preparation thereof - Google Patents
Organic dithiophosphinic compounds and the preparation thereofInfo
- Publication number
- GB902802A GB902802A GB42166/59A GB4216659A GB902802A GB 902802 A GB902802 A GB 902802A GB 42166/59 A GB42166/59 A GB 42166/59A GB 4216659 A GB4216659 A GB 4216659A GB 902802 A GB902802 A GB 902802A
- Authority
- GB
- United Kingdom
- Prior art keywords
- product
- substituted
- metal
- unsubstituted
- cationic group
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 8
- 239000002184 metal Substances 0.000 abstract 8
- -1 aliphatic hydrocarbon radicals Chemical class 0.000 abstract 7
- 125000002091 cationic group Chemical group 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 229920006395 saturated elastomer Polymers 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 229910052705 radium Inorganic materials 0.000 abstract 3
- 229910052701 rubidium Inorganic materials 0.000 abstract 3
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- 150000001721 carbon Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- 125000004437 phosphorous atom Chemical group 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- ILDOJCPFGWBYOL-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)-1,3,5-dioxaphosphinane Chemical compound CC(C)C1OC(C(C)C)PC(C(C)C)O1 ILDOJCPFGWBYOL-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005248 alkyl aryloxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 150000004292 cyclic ethers Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910001385 heavy metal Inorganic materials 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 229910052753 mercury Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium compounds
-
- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
-
- 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
- C07F9/6571—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 and oxygen atoms as the only ring hetero atoms
- C07F9/657163—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 and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
-
- 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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- 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
-
- 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
- C10M2223/061—Metal salts
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/06—Groups 3 or 13
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/14—Group 7
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/16—Groups 8, 9, or 10
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
Secondary dithiophosphinic acids, esters and salts of the general formula <FORM:0902802/IV (b)/1> wherein Y is hydrogen, a substituted or unsubstituted ammonium cationic group, a metal cationic group, or an organic ester-forming group and X is <FORM:0902802/IV (b)/2> wherein Ra and Rb are the same or different and are substituted or unsubstituted saturated or unsaturated branched or straight chain aliphatic hydrocarbon radicals in which any given linear carbon chain of said radicals contains from 1 to 18 carbon atoms, and, preferably, said substituted aliphatic hydrocarbon radicals have their substituents on a carbon atom at least 3 carbon atoms removed from the phosphorus atom, saturated or unsaturated substituted or unsubstituted alicyclic radicals, substituted or unsubstituted aryl radicals, and Ra and Rb respectively are attached directly to the phosphorus atom through a carbon atom and wherein R1 to R6 are the same or different and are alkyl groups of 1 to 10 carbon atoms are obtained by (1) contacting a secondary phosphine of the formula: <FORM:0902802/IV (b)/3> with a mixture of sulphur, water and an appropriate basic reagent to form the product in which Y is a substituted or unsubstituted ammonium cationic group or a metal cationic group, (2) and then if desired treating the product of step (1) with acid to form the product in which Y is hydrogen, and if desired converting the product so formed with a basic metallic reagent to form the product in which Y is a metal cationic group, or alternatively, if desired treating the product of step (1) with a metal salt in a cationic exchange reaction to form a product in which Y is a different metal cationic group, (3) and if desired either treating the product in which Y is hydrogen with an ethylenically unsaturated compound or treating the product in which Y is a metal cation with an organic halide to form the product in which Y is an ester group. The invention also includes the cyclic dithiophosphinic acids, esters and salts of the formula <FORM:0902802/IV (b)/4> wherein Y and R1 to R6 are as defined above. Th organic ester-forming group which Y may represent may be a substituted or unsubstituted saturated or unsaturated branched or straight chain aliphatic hydrocarbon radical, or a substituted or unsubstituted saturated or unsaturated alicyclic radical or a substituted or unsubstituted aryl radical. The reaction in step (1) is usually effected at 0-100 DEG C., preferably 15 DEG to 75 DEG C. and suitable acids for treating the salt product are HCl, dilute sulphuric acid and methane sulphonic acid; the treatment being generally effected at -30 DEG to 75 DEG C., preferably 10 DEG to 50 DEG C. The metal cationic group Y may be an alkali metal, e.g. Li, K or Na; an alkaline earth metal, a heavy metal, e.g. Cu, Hg or Ni or another metal, e.g. Al or Mg. Suitable bases for use in step (1) are alkali metal hydroxides, alkaline earth metal hydroxides and carbonates and ammonium hydroxide and an inert water-soluble organic solvent e.g. a lower aliphatic alcohol, a cyclic ether, or methyl ethyl ketone may be present. Atmospheric pressure is normally used in step (1) but higher or lower pressures are also suitable. Specified substituents which may be present in the radicals Ra and Rb are alkoxy, halogen, e.g. Cl, aryloxy, aralkoxy, alkaryloxy, amino, nitro, ureido, sulfo, hydroxyl, carbamyl, acyloxy, carbalkoxy, carboxy and aryl. Examples are given and the products are useful as oil additives and as pre-emergence herbicides. An example is also given for the preparation of 2,4,6-triisopropyl-1,3-dioxa-5-phosphacyclohexane by the procedure described in Specification 902,801.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78066958A | 1958-12-16 | 1958-12-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB902802A true GB902802A (en) | 1962-08-09 |
Family
ID=25120286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB42166/59A Expired GB902802A (en) | 1958-12-16 | 1959-12-11 | Organic dithiophosphinic compounds and the preparation thereof |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1163813B (en) |
| FR (1) | FR1244020A (en) |
| GB (1) | GB902802A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3541603A1 (en) * | 1984-11-28 | 1986-05-28 | American Cyanamid Co., Wayne, N.J. | METHOD FOR PRODUCING DIORGANOMONOTHIOPHOSPHINATES |
| US4661278A (en) * | 1984-11-28 | 1987-04-28 | American Cyanamid Company | Monothiophosphinates as acid, neutral, or mildly alkaline circuit sulfide collectors and process for using same |
| US5240622A (en) * | 1990-06-26 | 1993-08-31 | Ciba-Geigy Corporation | Dioxaphosphorinane compounds as stabilizers for organic materials |
| US8764880B2 (en) | 2006-06-14 | 2014-07-01 | Cytec Canada Inc. | Phosphinic acids and their sulfur derivatives and methods for their preparation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2797238A (en) * | 1954-01-26 | 1957-06-25 | Lubrizol Corp | Method for preparing organic phosphinodithioic compounds |
-
1959
- 1959-12-11 GB GB42166/59A patent/GB902802A/en not_active Expired
- 1959-12-16 FR FR813163A patent/FR1244020A/en not_active Expired
- 1959-12-16 DE DEA33540A patent/DE1163813B/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3541603A1 (en) * | 1984-11-28 | 1986-05-28 | American Cyanamid Co., Wayne, N.J. | METHOD FOR PRODUCING DIORGANOMONOTHIOPHOSPHINATES |
| US4661278A (en) * | 1984-11-28 | 1987-04-28 | American Cyanamid Company | Monothiophosphinates as acid, neutral, or mildly alkaline circuit sulfide collectors and process for using same |
| FR2593506A1 (en) * | 1984-11-28 | 1987-07-31 | American Cyanamid Co | PROCESS FOR THE SYNTHESIS OF DIORGANOMONOTHIOPHOSPHINATES |
| US5240622A (en) * | 1990-06-26 | 1993-08-31 | Ciba-Geigy Corporation | Dioxaphosphorinane compounds as stabilizers for organic materials |
| US8764880B2 (en) | 2006-06-14 | 2014-07-01 | Cytec Canada Inc. | Phosphinic acids and their sulfur derivatives and methods for their preparation |
| US9102695B2 (en) | 2006-06-14 | 2015-08-11 | Cytec Technology Corp. | Phosphinic acids and their sulfur derivatives and methods for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1163813B (en) | 1964-02-27 |
| FR1244020A (en) | 1960-10-21 |
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