US2925419A - Process for stabilising esters of acids of phosphorus and stable compositions of esters of acids of phosphorus - Google Patents

Process for stabilising esters of acids of phosphorus and stable compositions of esters of acids of phosphorus Download PDF

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Publication number
US2925419A
US2925419A US696921A US69692157A US2925419A US 2925419 A US2925419 A US 2925419A US 696921 A US696921 A US 696921A US 69692157 A US69692157 A US 69692157A US 2925419 A US2925419 A US 2925419A
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United States
Prior art keywords
esters
ester
parts
acids
stabilising
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Expired - Lifetime
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US696921A
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English (en)
Inventor
Diriwachter Hans
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Novartis AG
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JR Geigy AG
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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/16Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165Esters of thiophosphoric acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/025Purification; Separation; Stabilisation; Desodorisation of organo-phosphorus compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/08Esters of oxyacids of phosphorus
    • C07F9/09Esters of phosphoric acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6509Six-membered rings
    • C07F9/6512Six-membered rings having the nitrogen atoms in positions 1 and 3
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S260/00Chemistry of carbon compounds
    • Y10S260/15Antistatic agents not otherwise provided for
    • Y10S260/16Antistatic agents containing a metal, silicon, boron or phosphorus

Definitions

  • the present invention concerns a proces's forthe stabilising of. phosphoric acid estersf 'which can hefused, I
  • ananalogous composition in which: 1 part of xylene has been replaced by 1 part 0t epichlorohydrin, remains j stable, i. e.- there is no loss; oflcontent of the thiophosphoric acid, ester named.
  • esters of all acids of pentavalent and 7 also trivalent phosphorus are meant by phosphoric ;acid
  • esters thus, for example, apart from the esters of ""rtho phosphoric acid alsothose.
  • thiophosphoric :acid-[2-isopropyl-4- V methyl-pyrimidyl;@llfdiethyl ester has sunk to 20 parts whereas in this case also,- thecontent: of the thiophosphorie acid ester named remainsunchanged when can analogous composition containing 3 parts .of epichlorothose of phosphorous acid and of phosphonic and phos- I phinic acids are to be understood.
  • the invention is particularly concerned, however, with the stabilising of thiophosphoric acid l2-isopropyl-4-methyl-pyrimidyl-(6)1- diethyl ester and phosphoric acid-l3-methyl-pyrazolyl- (5)1-diethyl ester.
  • active ingredients for'pesticides .of all types as pure substances, as technical crude substances, as ready-for-use preparationsor as solid, semi-solid or liquid concentrates for the production of the latter are meant by phosphoric acid esters to be stabilised.
  • additives to lubricants and fuels can also be, for example, additives to lubricants and fuels, antistatic agents and flame-proofing a as xylene, benzene, diesel oil, kerosene, spindle oil or a petrolatum product, and 2-30% (calculated on the weight h dr n: .in t adlvi 3 par s "9f. Y sizc ns sat Product is-stored mh ane c u i enw I Y i YQ EJEampIe'3 jan alkyd.
  • phenol-ethylene" ""oiiid'e” condeils condensation product of 1 mol of nonyl-,'octy1- or isooetyl-phenolwith 5-10 mols of ethylene oxide
  • parts of'xylene is stored for 130 days at At the end of this time, the content of phosphoric acid-[3- methyl-pyrazolyl-(S)l-diethyl ester has'sunk to 10 parts.
  • Example 1 An emulsifiable solution for the preparation of insecticidal emulsions consisting of I V 20 parts of thiophosphoric -acid-.l2 isopropyl-4 rnethylpyrirnidyl-(6)l-diethyl'ester- 35 parts, of an alkylphenol-ethylene oxide condensation has been replaced by 1 part of epichlorohydrin, remains unchanged after storing under the same conditions.
  • Example 6 The solution of Example 5 can also be stabilised if I 4 parts of cyclohexene oxide are usedinstead of 4 parts product (condensation product of 1 molvof nonylof propylene oxide.
  • Example 7 r emulsified stabilised solutionaccording to the V uti omhaving i a high concentration present invention which canibe used forthe preparation of an insecticidal emulsion is obtained by dissolving I 40 parts of thiophosphoric acid-[2-isopropyl-4-methylpyrimid yl- (6 )']-diethyl es ter, 2 y,pa-rts ot an -alkyl phenol-ethylene oxide condensation product (condensation product of 1 mol of nonyl-, octylor iso-octyl-phenol with -10 mols of ethylene oxide) and 12 parts of styrol oxide in 28 parts of xylene.
  • Example '8 Another emulsifiable stabilised solution according to the present invention isobtained by dissolving 25 parts of thiophosphoric acid[2#isopropyl 4 methyl-pyrimidyl- (6)1-diethyl ester, 1 0 parts 'of 'en alkyl' phenohethylene oxide condensation product (condensation product of 1 mol of nonyl-,roctyl-, or is ooctyl-p henol with 5-10 mols of ethylene oxide) and 0.5 part "of cyclohexene oxide in 64.5 parts of benzene. r
  • aphosphoric acid dialkyl ester selected from the group consisting of thiophosphoric acid-[Z-isopropyl 4 methyl-pyrimidyl-(6) 1- diethyl ester and phosphoric acid-[3-methyl-pyrazoly1- (5)]-diethyl ester, which comprises adding to'sa'id ester from 2% to 30%, calculated ,on the weight of said ester, of a stabilising agent-selected from th e grou consisting 4.
  • composition of matter comprising a phosphoric acid dialkyl ester selected from the group consisting of thiophospho'ric acid-[2i'sopropyl 4 methyl pyrimidyl- (6)]-diethyl ester and phosphoric a'cid-[3-methyl-pyrazolyl-(S)]-diethyl ester,' and from 2% to calculated on the weight of said esters, of a stabilising agent selected from the group consisting of epichlorohydrin, cyclohexene oxide, propylene oxide and styrol oxide.
  • a stabilising agent selected from the group consisting of epichlorohydrin, cyclohexene oxide, propylene oxide and styrol oxide.
  • composition of matter comprising thiophosphori'c acid-[2-isopropyl-4methyl-pyrimidyl-( 6) 1 -diethyl ester, and from 2% to 30%, calculated on the, weight of said ester, of .the stabilising :agent epichlorohydrin.
  • composition of matter comprising phosphoric 'acid-[3-methyl pyrazolyl-(5)l-diethyl ester,- and from 2 %'to 30%,.calculated onthe weight of the said ester,

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  • 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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US696921A 1956-11-30 1957-11-18 Process for stabilising esters of acids of phosphorus and stable compositions of esters of acids of phosphorus Expired - Lifetime US2925419A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH848485X 1956-11-30

Publications (1)

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US2925419A true US2925419A (en) 1960-02-16

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US696921A Expired - Lifetime US2925419A (en) 1956-11-30 1957-11-18 Process for stabilising esters of acids of phosphorus and stable compositions of esters of acids of phosphorus

Country Status (5)

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US (1) US2925419A (de)
CH (1) CH348284A (de)
DE (1) DE1107228B (de)
FR (1) FR1187378A (de)
GB (1) GB848485A (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3258463A (en) * 1961-08-29 1966-06-28 Stauffer Chemical Co Phosphoro sulfenates
CN113861131A (zh) * 2021-11-08 2021-12-31 深圳菲斯生物科技有限公司 一种西替利嗪杂质c的制备方法

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3439068A (en) * 1965-05-21 1969-04-15 Olin Mathieson Process for stabilizing a polyol phosphorus by adding limonene dioxide,vinylcyclohexene dioxide or dicyclodiepoxy carboxylate and composition
DE2411764A1 (de) * 1973-03-16 1974-09-26 Sandoz Ag Stabilisierte biozide mittel mit dem wirkstoff 0,0-dimethyl-0-chinoxylinyl-(2)thionophosphat
US4634541A (en) * 1985-01-28 1987-01-06 Standard Oil Company Color stabilizers for zinc dithiophosphates
US5288918A (en) * 1992-09-29 1994-02-22 Union Carbide Chemicals & Plastics Technology Corporation Hydroformylation process
US5364950A (en) * 1992-09-29 1994-11-15 Union Carbide Chimicals & Plastics Technology Corporation Process for stabilizing phosphite ligands in hydroformylation reaction mixtures
US5756855A (en) * 1994-08-19 1998-05-26 Union Carbide Chemicals & Plastics Technology Corporation Stabilization of phosphite ligands in hydroformylation process

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB690585A (en) * 1950-03-01 1953-04-22 Standard Oil Dev Co Improvements in or relating to insecticidal compositions

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB690585A (en) * 1950-03-01 1953-04-22 Standard Oil Dev Co Improvements in or relating to insecticidal compositions

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3258463A (en) * 1961-08-29 1966-06-28 Stauffer Chemical Co Phosphoro sulfenates
CN113861131A (zh) * 2021-11-08 2021-12-31 深圳菲斯生物科技有限公司 一种西替利嗪杂质c的制备方法
CN113861131B (zh) * 2021-11-08 2024-04-19 深圳菲斯生物科技有限公司 一种西替利嗪杂质c的制备方法

Also Published As

Publication number Publication date
DE1107228B (de) 1961-05-25
CH348284A (de) 1960-08-15
GB848485A (en) 1960-09-21
FR1187378A (fr) 1959-09-10

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