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 PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- esters
- ester
- parts
- acids
- stabilising
- 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 - Lifetime
Links
- 150000002148 esters Chemical class 0.000 title claims description 21
- 230000003019 stabilising effect Effects 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 title description 8
- 239000000203 mixture Substances 0.000 title description 8
- 150000007513 acids Chemical class 0.000 title description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title description 3
- 229910052698 phosphorus Inorganic materials 0.000 title description 3
- 239000011574 phosphorus Substances 0.000 title description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 5
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 3
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- 239000007859 condensation product Substances 0.000 description 7
- -1 methyl-pyrimidyl Chemical group 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 229960004838 phosphoric acid Drugs 0.000 description 5
- 235000011007 phosphoric acid Nutrition 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004264 Petrolatum Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 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
-
- 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
- C07F9/025—Purification; Separation; Stabilisation; Desodorisation of organo-phosphorus 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- 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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
-
- Y—GENERAL 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/15—Antistatic agents not otherwise provided for
- Y10S260/16—Antistatic 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,
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH848485X | 1956-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2925419A true US2925419A (en) | 1960-02-16 |
Family
ID=4542065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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)
| Country | Link |
|---|---|
| US (1) | US2925419A (de) |
| CH (1) | CH348284A (de) |
| DE (1) | DE1107228B (de) |
| FR (1) | FR1187378A (de) |
| GB (1) | GB848485A (de) |
Cited By (2)
| 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)
| 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)
| 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 |
-
1956
- 1956-11-30 CH CH348284D patent/CH348284A/de unknown
-
1957
- 1957-11-18 US US696921A patent/US2925419A/en not_active Expired - Lifetime
- 1957-11-29 GB GB37210/57A patent/GB848485A/en not_active Expired
- 1957-11-29 FR FR1187378D patent/FR1187378A/fr not_active Expired
- 1957-11-29 DE DEG23446A patent/DE1107228B/de active Pending
Patent Citations (1)
| 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)
| 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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