GB821937A - New dithiophosphoric acids and derivatives thereof and process for their manufacture - Google Patents
New dithiophosphoric acids and derivatives thereof and process for their manufactureInfo
- Publication number
- GB821937A GB821937A GB2814755A GB2814755A GB821937A GB 821937 A GB821937 A GB 821937A GB 2814755 A GB2814755 A GB 2814755A GB 2814755 A GB2814755 A GB 2814755A GB 821937 A GB821937 A GB 821937A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- reacting
- dithiophosphoric
- acids
- dibutyl
- 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
- 239000002253 acid Substances 0.000 title abstract 25
- 150000007513 acids Chemical class 0.000 title abstract 15
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 7
- 150000002148 esters Chemical class 0.000 abstract 6
- 150000003839 salts Chemical class 0.000 abstract 5
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical class CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 2
- 125000003118 aryl group Chemical group 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
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000002480 mineral oil Substances 0.000 abstract 2
- 235000010446 mineral oil Nutrition 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 abstract 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 2
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 abstract 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-Phenylethanol Natural products OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 abstract 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910001385 heavy metal Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229920001021 polysulfide Polymers 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1652—Polyol derivatives esterified at least twice by thiophosphoric acid groups
-
- 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
- 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
- C10M2223/043—Ammonium or amine 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
- C10M2223/045—Metal containing thio derivatives
-
- 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
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Abstract
Mineral oil compositions contain dithiophosphoric acids of the general formula <FORM:0821937/III/1> wherein R represents an aliphatic, aromatic or aliphatic-aromatic residue containing not more than 20 carbon atoms, any of which may contain a halogen atom, R1 represents hydrogen or a residue as defined under R, and X represents an oxygen or sulphur atom, or salts of such acids such as the oleylamine salt, or di-, tri- or tetrasulphides derived from such acids by reaction with sulphuryl chloride, sulphur dichloride or sulphur monochloride respectively, or esters of such acids obtained by reacting the acids with alkylene oxides, or thiol-thionophosphoric acids obtained by reacting the aforesaid esters with phosphorus pentasulphide. It is preferred to add from 1 to 5% by weight of said compounds to the mineral oil. Typical compounds of the above general formula are b : b - di - (o : o - dibutyl - dithiophosphoric acid)-diethyl - tetrathiophosphoric acid, b : b - di(S : S - dibutyl - tetrathiophosphoric acid) - diethyl - tetrathiophosphoric acid, and b : b 1 - di(o : o - di - n - octyl - dithiophosphoric acid) - diethyl - thiolthionophosphoric acid, and a typical polysulphide is sym-bis-[1 : 11-di-(o : o-di - n - butyl - dithiophosphoric acid) - 3 : 31-dichlorodipropyl - 2 : 21 - thionophosphoric acid] tetra-sulphide.ALSO:The invention comprises dithiophosphoric acids of the general formula <FORM:0821937/IV (a)/1> wherein R represents an aliphatic, aromatic or aliphatic-aromatic residue containing not more than 20 carbon atoms, any of which may contain halogen, R1 represents hydrogen or a residue as defined under R, and X represents a oxygen or sulphur atom, and the preparation thereof by reacting a thiolthiono-phosphoric acid of the general formula <FORM:0821937/IV (a)/2> wherein R and X have the above significance, with the required ethylene oxide or sulphide and the resulting ester is reacted with phosphorus pentasulphide. The invention also comprises salts of the above dithiophosphoric acids, di-, tri- and penta-sulphides obtained by reacting the above dithiophosphoric acids with sulphuryl chloride, sulphur dichloride and sulphur mono-chloride respectively, esters of the above dithiophosphoric acids obtained by reacting the acids with alkylene oxides, and thiol-thionophosphoric acids obtained by reaction the above dithiophosphoric acids with phosphorus pentasulphide. Salts of the above dithiophosphoric acids may be the alkali metal, alkaline earth metal and heavy metal salts, and salts with amines such as oleylamine. In the examples: (1) b : b 1 - (O : O - di - n - butyl - dithiophosphoric acid) - diethyl - thiolthionophosphoric acid (the oleylamine salt is also referred to) is prepared by reacting ethyl oxide with O : O-din-butyl-thiolthionophosphoric acid, and reacting the resulting 1-(O : O-di-n-butyl-dithiophosphoric acid)-ethanol-(2) with phosphorus pentasulphide; (2) 1 : 11-di-(O : O-di-n-butyl-dithiophosphoric acid) - 3 : 31 - dichlorodipropyl (2 : 21)-thiolthionophosphoric acid is prepared by reacting O : O-di-n-butyl-thiolthionophosphoric acid and epichlorhydrin, and reacting the resulting 1 - (O : O - di - n - butyl - dithiophosphoric acid)-3-chloropropane-ol-(2) with phosphorus pentasulphide; the product may be converted into a tetrasulphide by reaction with the calculated quantity of sulphur monochloride, the tetrasulphide being described as sym.-bis[1 : 11 - di - (O : O - di - n - butyl - dithiophosphoric acid) - 3 : 31 - dichlorodipropyl - (2 : 21) - thiono - phosphoric acid] - tetrasulphide; (3) b : b 1 - di - [O : O - di - (4 - chlorophenyl) - dithiophosphoric acid] - a : a 1 - diphenyldiethyl - thiolthiono-phosphoric (the oleylamine salt is also referred to) is prepared as in (1), b -[O : O-di-(4-chlorophenyl) - thiolthionophosphoric acid] - a - phenyl-ethanol being the intermediate compound obtained by reacting phenyl-ethylene oxide with O : O - di - (4 - chlorophenyl) - thiolthionophosphoric acid; (4) b : b - di - (O : O - dibutyl - dithio - phosphoric acid) - diethyl - tetrathiophosphoric acid is prepared by reacting O : O-dibutyl-thiolthionophosphoric acid with ethylene sulphide to form O : O-dibutyl-dithiophosphoric acid S-(b -mercaptoethyl)-ester and reacting this ester with phosphorus pentasulphide; (5) b ,b -di-(S : S-dibutyl-tetrahiophosphoric acid)-diethyl-tetrathiophosphoric acid is prepared by reacting S : S-dibutyl-tetrathiophosphoric acid with ethylene sulphide to form S : S-dibutyl-tetrathiophosphoric acid S-(b -mercaptoethyl)-ester and reacting this ester with phosphorus pentasulphide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED0018787 | 1954-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB821937A true GB821937A (en) | 1959-10-14 |
Family
ID=25949268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2814755A Expired GB821937A (en) | 1954-10-03 | 1955-10-03 | New dithiophosphoric acids and derivatives thereof and process for their manufacture |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE948156C (en) |
| GB (1) | GB821937A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3006448A1 (en) * | 2014-10-08 | 2016-04-13 | Afton Chemical Corporation | Phosphorous-containing compunds and uses thereof |
| JP2017078156A (en) * | 2015-08-19 | 2017-04-27 | アフトン・ケミカル・コーポレーションＡｆｔｏｎ Ｃｈｅｍｉｃａｌ Ｃｏｒｐｏｒａｔｉｏｎ | Phosphorous containing compounds and uses thereof |
| US10329511B2 (en) * | 2016-10-31 | 2019-06-25 | Afton Chemical Corporation | Lubricant compositions comprising thiophosphates and thiophosphate derivatives |
| CN116903979A (en) * | 2023-09-13 | 2023-10-20 | 台州黄岩泽钰新材料科技有限公司 | Antistatic starch-based biodegradable material and preparation process thereof |
| CN118754911A (en) * | 2024-09-06 | 2024-10-11 | 青岛科技大学 | A kind of O,O-dialkyl dithiophosphate collector and its preparation method and application |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3197496A (en) * | 1961-08-09 | 1965-07-27 | Lubrizol Corp | Polyphosphorus ester derivatives of o, o-dihydrocarbyl-s-hydroxylalkyl phosphorodithioates |
| FR2586684B1 (en) * | 1985-09-04 | 1989-05-19 | Inst Francais Du Petrole | METAL DIHYDROCARBYL-DITHIOPHOSPHYL-DITHIOPHOSPHATES, THEIR PREPARATION AND THEIR USE AS LUBRICANT ADDITIVES |
| FR2651000B1 (en) * | 1989-08-21 | 1991-10-31 | Inst Francais Du Petrole | COPPER DIHYDROCARBYLDITHIOPHOSPHYLDITHIOPHOSPHATES, THEIR PREPARATION AND THEIR USE AS LUBRICANT ADDITIVES |
-
1954
- 1954-10-03 DE DED18787A patent/DE948156C/en not_active Expired
-
1955
- 1955-10-03 GB GB2814755A patent/GB821937A/en not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3006448A1 (en) * | 2014-10-08 | 2016-04-13 | Afton Chemical Corporation | Phosphorous-containing compunds and uses thereof |
| CN105541902A (en) * | 2014-10-08 | 2016-05-04 | 雅富顿化学公司 | Phosphorous-Containing Compounds and Uses Thereof |
| US9944879B2 (en) | 2014-10-08 | 2018-04-17 | Afton Chemical Corporation | Phosphorous-containing compounds and uses thereof |
| CN105541902B (en) * | 2014-10-08 | 2019-04-12 | 雅富顿化学公司 | Phosphorus-containing compound and its application |
| JP2017078156A (en) * | 2015-08-19 | 2017-04-27 | アフトン・ケミカル・コーポレーションＡｆｔｏｎ Ｃｈｅｍｉｃａｌ Ｃｏｒｐｏｒａｔｉｏｎ | Phosphorous containing compounds and uses thereof |
| US10329511B2 (en) * | 2016-10-31 | 2019-06-25 | Afton Chemical Corporation | Lubricant compositions comprising thiophosphates and thiophosphate derivatives |
| EP3532578A4 (en) * | 2016-10-31 | 2020-07-22 | Afton Chemical Corporation | LUBRICANT ADDITIVE COMPOSITIONS WITH PHOSPHORUS COMPOUNDS AND USES THEREOF |
| CN116903979A (en) * | 2023-09-13 | 2023-10-20 | 台州黄岩泽钰新材料科技有限公司 | Antistatic starch-based biodegradable material and preparation process thereof |
| CN116903979B (en) * | 2023-09-13 | 2023-12-08 | 台州黄岩泽钰新材料科技有限公司 | Antistatic starch-based biodegradable material and preparation process thereof |
| CN118754911A (en) * | 2024-09-06 | 2024-10-11 | 青岛科技大学 | A kind of O,O-dialkyl dithiophosphate collector and its preparation method and application |
Also Published As
| Publication number | Publication date |
|---|---|
| DE948156C (en) | 1956-08-30 |
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