DE847897C - Verfahren zur Herstellung von Dithiophosphorsaeuretriestern - Google Patents
Verfahren zur Herstellung von DithiophosphorsaeuretriesternInfo
- Publication number
- DE847897C DE847897C DEA12971A DEA0012971A DE847897C DE 847897 C DE847897 C DE 847897C DE A12971 A DEA12971 A DE A12971A DE A0012971 A DEA0012971 A DE A0012971A DE 847897 C DE847897 C DE 847897C
- Authority
- DE
- Germany
- Prior art keywords
- dithiophosphoric acid
- acid
- carried out
- ester
- hydroquinone
- 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
- -1 dithiophosphoric acid triesters Chemical class 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Chemical class 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000007788 liquid Substances 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 16
- IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical compound CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 7
- 239000011976 maleic acid Substances 0.000 description 7
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CZGGKXNYNPJFAX-UHFFFAOYSA-N Dimethyldithiophosphate Chemical group COP(S)(=S)OC CZGGKXNYNPJFAX-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000011132 calcium sulphate Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- UEKQGZQLUMSLNW-UHFFFAOYSA-N Propyl isome Chemical compound C1=C2C(C(=O)OCCC)C(C(=O)OCCC)C(C)CC2=CC2=C1OCO2 UEKQGZQLUMSLNW-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- NKYPKIVMIGIWOB-UHFFFAOYSA-N [amino(methoxy)phosphinothioyl]oxymethane Chemical compound COP(N)(=S)OC NKYPKIVMIGIWOB-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- LHLHWDNRHALZNF-FPLPWBNLSA-N (z)-2,3-di(propan-2-yl)but-2-enedioic acid Chemical compound CC(C)C(\C(O)=O)=C(/C(C)C)C(O)=O LHLHWDNRHALZNF-FPLPWBNLSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- ROPXFXOUUANXRR-YPKPFQOOSA-N bis(2-ethylhexyl) (z)-but-2-enedioate Chemical compound CCCCC(CC)COC(=O)\C=C/C(=O)OCC(CC)CCCC ROPXFXOUUANXRR-YPKPFQOOSA-N 0.000 description 1
- RSRICHZMFPHXLE-AATRIKPKSA-N bis(2-methylpropyl) (e)-but-2-enedioate Chemical compound CC(C)COC(=O)\C=C\C(=O)OCC(C)C RSRICHZMFPHXLE-AATRIKPKSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 125000003901 ceryl 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])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 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- FNMTVMWFISHPEV-WAYWQWQTSA-N dipropan-2-yl (z)-but-2-enedioate Chemical compound CC(C)OC(=O)\C=C/C(=O)OC(C)C FNMTVMWFISHPEV-WAYWQWQTSA-N 0.000 description 1
- 239000008396 flotation agent Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- OXFUXNFMHFCELM-UHFFFAOYSA-N tripropan-2-yl phosphate Chemical compound CC(C)OP(=O)(OC(C)C)OC(C)C OXFUXNFMHFCELM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/167—Phosphorus-containing compounds
- C23F11/1673—Esters of phosphoric or thiophosphoric acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
-
- 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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/5398—Phosphorus bound to sulfur
-
- 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
- C10M2223/047—Thioderivatives not containing metallic elements
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Materials Engineering (AREA)
- Pest Control & Pesticides (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dentistry (AREA)
- General Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US147325A US2578652A (en) | 1950-03-02 | 1950-03-02 | Addition product of diester of dithiophosphoric acid and maleic acid and its esters, and method of preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE847897C true DE847897C (de) | 1952-08-28 |
Family
ID=22521112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA12971A Expired DE847897C (de) | 1950-03-02 | 1951-03-01 | Verfahren zur Herstellung von Dithiophosphorsaeuretriestern |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US2578652A (es) |
| BE (1) | BE501609A (es) |
| CH (1) | CH292795A (es) |
| DE (1) | DE847897C (es) |
| ES (1) | ES196779A1 (es) |
| FR (1) | FR1033275A (es) |
| GB (1) | GB699522A (es) |
| NL (2) | NL80825C (es) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE942988C (de) * | 1953-12-11 | 1956-05-09 | Bayer Ag | Verfahren zur Herstellung von Thiolphosphorsaeuretriestern |
| DE951717C (de) * | 1953-12-19 | 1956-10-31 | Bayer Ag | Verfahren zur Herstellung von Thiono-thiol-phosphorsaeuretriestern |
| DE956503C (de) * | 1953-07-22 | 1957-01-17 | Geigy Ag J R | Verfahren zur Herstellung neuer Phosphor- bzw. Thiophosphorsaeureester |
| DE1006854B (de) * | 1955-02-10 | 1957-04-25 | Bayer Ag | Verfahren zur Herstellung von Thionophosphorsaeureestern |
| DE1011416B (de) * | 1955-02-10 | 1957-07-04 | Bayer Ag | Verfahren zur Herstellung von 0, 0-Dialkyl-thiol- und -thiol-thiono-phosphorsaeuretriestern |
| DE1011660B (de) * | 1953-02-18 | 1957-07-04 | American Cyanamid Co | Schaedlingsbekaempfungsmittel |
| DE1063154B (de) * | 1950-05-09 | 1959-08-13 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern |
| DE1136528B (de) * | 1958-11-07 | 1962-09-13 | Rhone Poulenc Sa | Mittel zum Bekaempfen von Schaedlingen, insbesondere von Insekten und Milben |
| DE1177153B (de) * | 1961-08-18 | 1964-09-03 | Stauffer Chemical Co | Verfahren zur Herstellung von Alkyldithio-phosphonsaeure-S-[1, 2-bis-(alkoxycarbonyl)-aethyl]-O-alkylestern |
| DE1188859B (de) * | 1960-12-10 | 1965-03-11 | Basf Ag | Mittel zur Bekaempfung von Insekten |
| DE1252960B (de) * | 1960-12-10 | 1967-10-26 | Basf Ag | Mittel zur Bekaempfung von Insekten |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2675321A (en) * | 1951-06-12 | 1954-04-13 | American Cyanamid Co | Coated pigment and mineral oil ink containing same |
| US2632020A (en) * | 1951-07-07 | 1953-03-17 | American Cyanamid Co | Dithiophosphate esters |
| US2644002A (en) * | 1951-08-29 | 1953-06-30 | American Cyanamid Co | Thiophosphatosuccinimides |
| US2630451A (en) * | 1951-12-08 | 1953-03-03 | American Cyanamid Co | Dithiophosphate esters |
| US2802856A (en) * | 1953-09-08 | 1957-08-13 | Lubrizol Corp | Methods of preparing tri-esters of thiophosphoric acids |
| NL92943C (es) * | 1954-09-08 | |||
| US2976308A (en) * | 1954-10-13 | 1961-03-21 | Lubrizol Corp | Preparation of phosphorodithioate triesters |
| US2876244A (en) * | 1954-12-30 | 1959-03-03 | Union Carbide Corp | Production of heterocyclic dithiophosphoric esters |
| FR1125317A (fr) * | 1955-04-12 | 1956-10-29 | Procédé de désodorisation de l'o, o-diméthyl-dithiophosphate de diéthyl mercaptosuccinate | |
| US2879284A (en) * | 1955-08-12 | 1959-03-24 | American Cyanamid Co | Odor removal and stabilization of phosphate-containing pesticides |
| US2911335A (en) * | 1955-09-27 | 1959-11-03 | Allied Chem | Thiophosphate ester fungicides |
| US2876156A (en) * | 1956-05-03 | 1959-03-03 | Pfizer & Co C | Insecticides-derivatives of itaconic acid |
| DE1112338B (de) * | 1956-05-03 | 1961-08-03 | Pfizer & Co C | Schaedlingsbekaempfungsmittel mit insekticider und insbesondere miticider Wirkung |
| US2861093A (en) * | 1956-09-24 | 1958-11-18 | Eastman Kodak Co | Reaction products of dialkyl phosphorothiolothionates and mucohalic acids |
| DE1034612B (de) * | 1956-09-28 | 1958-07-24 | Basf Ag | Verfahren zur Herstellung von Estern der Phosphorsaeure und Thiophosphorsaeure |
| US2948682A (en) * | 1956-12-24 | 1960-08-09 | Pure Oil Co | Formyl triesters of dithiophosphoric acid and lubricating oil compositions containing same |
| US2947775A (en) * | 1957-11-25 | 1960-08-02 | Eastman Kodak Co | O, o-dialkyl s-(2-acetoxy-2-cyanoethyl) phosphorothiolothionates |
| US2957019A (en) * | 1958-02-14 | 1960-10-18 | Eastman Kodak Co | O, o-dialkyl s-(2-cyano-haloalkyl) phosphorothiolothionates |
| US3136686A (en) * | 1958-10-31 | 1964-06-09 | Ciba Ltd | Omicron, omicron-dialkyl s-alkenyl phosphorothioates and insecticidal compositions and methods employing same |
| US3074990A (en) * | 1958-12-29 | 1963-01-22 | Universal Oil Prod Co | Alkylthiophosphoric acid salt of polymeric condensation product and use thereof |
| BE626519A (es) * | 1959-06-16 | |||
| US3030264A (en) * | 1960-03-11 | 1962-04-17 | Monsanto Chemicals | 1, 2-bis (oxycarbonyl) ethyl phosphinothioates |
| US3048517A (en) * | 1960-05-12 | 1962-08-07 | Monsanto Chemicals | 2-nitroalkyl phosphorothioates |
| US3109770A (en) * | 1961-04-10 | 1963-11-05 | Stauffer Chemical Co | Dialkoxyphosphinyl carbalkoxyalkyl disulfide pesticides |
| US3092543A (en) * | 1961-05-09 | 1963-06-04 | Velsicol Chemical Corp | Allyl phthalate pesticidal compositions |
| DE1198360B (de) * | 1961-08-03 | 1965-08-12 | Imperial Chemical Industries Limited, London | Verfahren zur Herstellung von o-Alkyl-S-(l-phenyl-2-alkoxycarbonyl-äthyl) - alkylthiophosphonaten |
| US3515782A (en) * | 1964-11-27 | 1970-06-02 | American Cyanamid Co | Method for controlling insects |
| US3359203A (en) * | 1965-09-01 | 1967-12-19 | Exxon Research Engineering Co | Ashless dithiophosphoric acid derivatives |
| US3440305A (en) * | 1965-09-30 | 1969-04-22 | American Cyanamid Co | Process for upgrading malathion |
| US3470272A (en) * | 1966-10-24 | 1969-09-30 | Mobil Oil Corp | Process for making phosphorothioates |
| US3463841A (en) * | 1966-11-01 | 1969-08-26 | American Cyanamid Co | Malathion manufacture |
| CH569416A5 (es) * | 1972-04-27 | 1975-11-28 | Ciba Geigy Ag | |
| US4058605A (en) * | 1975-06-11 | 1977-11-15 | Sun Ventures, Inc. | Insecticides from dimethylmuconic acid |
| DE2715924A1 (de) * | 1977-04-09 | 1978-10-12 | Basf Ag | Neue phosphorsaeurederivate |
| DE2746057A1 (de) * | 1977-10-13 | 1979-04-26 | Basf Ag | Neue phosphor(phosphon)-saeureester |
| US5614203A (en) * | 1995-01-30 | 1997-03-25 | Environmentally Safe Systems, Inc. | Environmentally safe pesticide and plant growth accelerator |
| US5646133A (en) * | 1996-03-14 | 1997-07-08 | Donlar Corporation | Polyaspartic acid and its analogues in combination with insecticides |
| US6046144A (en) * | 1997-06-02 | 2000-04-04 | R.T. Vanderbilt Co., Inc. | Combination of phosphate based additives and sulfonate salts for hydraulic fluids and lubricating compositions |
| DE19953775A1 (de) | 1999-11-09 | 2001-05-10 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10015310A1 (de) * | 2000-03-28 | 2001-10-04 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| US8012498B2 (en) | 2004-07-12 | 2011-09-06 | Sandhya Goyal | Topical gel formulation comprising organophosphate insecticide and preparation thereof |
| US8158139B2 (en) * | 2004-07-12 | 2012-04-17 | Taro Pharmaceuticals North America, Inc. | Topical gel formulation comprising organophosphate insecticide and preparation thereof |
| US7560445B2 (en) | 2005-07-06 | 2009-07-14 | Taro Pharmaceuticals North America, Inc. | Process for preparing malathion for pharmaceutical use |
| WO2009007998A1 (en) | 2007-07-09 | 2009-01-15 | Suven Life Sciences Limited | Process for the preparation of malathion and its intermediate |
| EP2360132B1 (en) | 2010-01-20 | 2014-06-11 | W.R. Grace & Co.-Conn. | High curing inducing surface applied setting retarder |
| HUE065408T2 (hu) * | 2018-09-27 | 2024-05-28 | Cheminova As | Malation katalizált és zöld elõállítási eljárása |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2528732A (en) * | 1947-01-31 | 1950-11-07 | Socony Vacuum Oil Co Inc | Reaction products of diesters of dithiophosphoric acid and mineral oil compositions containing the same |
-
0
- NL NL7604840.A patent/NL159376B/xx unknown
- NL NL80825D patent/NL80825C/xx active
- BE BE501609D patent/BE501609A/xx unknown
-
1950
- 1950-03-02 US US147325A patent/US2578652A/en not_active Expired - Lifetime
-
1951
- 1951-02-16 GB GB3808/51A patent/GB699522A/en not_active Expired
- 1951-03-01 CH CH292795D patent/CH292795A/fr unknown
- 1951-03-01 DE DEA12971A patent/DE847897C/de not_active Expired
- 1951-03-01 FR FR1033275D patent/FR1033275A/fr not_active Expired
- 1951-03-01 ES ES0196779A patent/ES196779A1/es not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1063154B (de) * | 1950-05-09 | 1959-08-13 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern |
| DE1011660B (de) * | 1953-02-18 | 1957-07-04 | American Cyanamid Co | Schaedlingsbekaempfungsmittel |
| DE956503C (de) * | 1953-07-22 | 1957-01-17 | Geigy Ag J R | Verfahren zur Herstellung neuer Phosphor- bzw. Thiophosphorsaeureester |
| DE942988C (de) * | 1953-12-11 | 1956-05-09 | Bayer Ag | Verfahren zur Herstellung von Thiolphosphorsaeuretriestern |
| DE951717C (de) * | 1953-12-19 | 1956-10-31 | Bayer Ag | Verfahren zur Herstellung von Thiono-thiol-phosphorsaeuretriestern |
| DE1006854B (de) * | 1955-02-10 | 1957-04-25 | Bayer Ag | Verfahren zur Herstellung von Thionophosphorsaeureestern |
| DE1011416B (de) * | 1955-02-10 | 1957-07-04 | Bayer Ag | Verfahren zur Herstellung von 0, 0-Dialkyl-thiol- und -thiol-thiono-phosphorsaeuretriestern |
| DE1136528B (de) * | 1958-11-07 | 1962-09-13 | Rhone Poulenc Sa | Mittel zum Bekaempfen von Schaedlingen, insbesondere von Insekten und Milben |
| DE1188859B (de) * | 1960-12-10 | 1965-03-11 | Basf Ag | Mittel zur Bekaempfung von Insekten |
| DE1252960B (de) * | 1960-12-10 | 1967-10-26 | Basf Ag | Mittel zur Bekaempfung von Insekten |
| DE1177153B (de) * | 1961-08-18 | 1964-09-03 | Stauffer Chemical Co | Verfahren zur Herstellung von Alkyldithio-phosphonsaeure-S-[1, 2-bis-(alkoxycarbonyl)-aethyl]-O-alkylestern |
Also Published As
| Publication number | Publication date |
|---|---|
| ES196779A1 (es) | 1953-04-01 |
| FR1033275A (fr) | 1953-07-09 |
| BE501609A (es) | |
| US2578652A (en) | 1951-12-18 |
| NL159376B (nl) | |
| GB699522A (en) | 1953-11-11 |
| NL80825C (es) | |
| CH292795A (fr) | 1953-08-31 |
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