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
  • C07F9/025—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
  • C07F9/16—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

Definitions

• This invention relates to a process for reducing the objectionable odor of a malodorous phosphorodithioate compound. More particularly, it relates to a process for the removal of odor from a malodorous phosphoro- Patented Apr. 18, 1961' ice cedure develops a strong obnoxious odor after storagefor several months. To the present, there is lacking a simple, inexpensive and expeditious process for removing the objectionable odor found in phosphorodithioate insecticides.
• Phosphorodithioate insecticides of the type with which the present invention is concerned are usually esters and may be represented by the general formula in which R; and R are each selected from the group consistingot aliphatic and aromatic hydrocarbon radi:
• V cals, and R and 'R' are selected from the group consistin which R and R have the meaning shown above, with an unsaturated compound of the formula pncooaz asses;
• a typical ester is O,O-dimethy1-S-( 1,2-dicarbethoxyethyl)- phosphorodithioate which is commercially availableas malathio'n insecticide.
• Phosphorodithioate insecticides of the type hereinbefore described have achieved a recognized place in the art as eXtremly useful insecticides byjvir-tuevof thefact of their relatively low mammalian toxicity. Such phos-.
• phorodithioate insecticides find usefor the control of asphids, spider mites, scales, house flies as well as a wide range of other sucking and chewing insects.
• phosphorodithioate inwhiqh i lu he use of i u Qx dtzin suhsances.
• Such an insecticide substantially devoid of malodor, is in contrast to both the crude or technical grade of in:
• secticide and a refined grade of phosphorodithioate in secticide Such an insecticide may be advantageouslyemployed, for example, in fly sprays and in suitable-solvents for the impregnation of textiles,.particularly arti. cles of clothing, to provide insecticidal activity. It may' be used with advantage for the control of numerous Further, the treatment renders the insecticide for even wider use, as, for ex-- ample, in grain storage elevators and the like.
• the in ⁇ secticide after having been subjected to the treatment. with ozone is substantially free from malodor and ac-' ceptable for use by the householder, gardener and others who have disapproved of the heretofore available in- However,. none of the active properties applicable for the destructionof insects have been lost by the treatment.
• The; treatment of' the present invention further improves the: insecticide in that even after prolonged storage under" variousconditions little or no objectionable odor is noted.
• the present process therefore, involves the passing of.
• ozone or an ozone containing gas, through or in contact: with theinsecticide soas to reduce'the objectionable odor of amalodorous phosphorodithioate insecticide.
• the ozone used in the presentprocess may be admixed with oxygen, air or other non-reactive diluent gases without affecting the efiiciency of the proc-- ess.
• an ozone concentration of from about 0.05 to about 3.5 weight percent in these gases is ef-- fective. It has been found that'as little as 0.1 weight percent of ozone based upon the weight, of insecticide Y ,may.
• inert and non-reactive gas such as air, oxygen, nitrogen or the like may be used to sweep out volatiles, such as residual ozone and the oxidation products produced .during the treatment, which have been expelled from the malodorous insecticide.
• the process may be carried out over a considerably Wide temperature range.
• the insecticide to be deodorized is a liquid, temperatures from about 25 C. to about 90 C. may be effectively employed.
• a liquid phosphorodithioate insecticide may be treated with ozone or an ozonecontaining gas in the absence of solvent at these process temperatures, it is also possible to efiect a reduction of objectionable'odor when a solvent for the insecticide is employed.
• solvents suitable for the phosphorodithioate insecticides may be mentioned esters, alcohols, ketones, hydrocarlions, and other suitable solvents which are non-reactive with the insecticides and with ozone.
• EXAMPLE II Ina continuously stirred pot reactor are charged 100 parts of technical grade liquid O,O-dimethyl-S-(1,2-dicarbethoxyethyl)-phosphorodithioate having some malodor. An ozone-oxygen mixture, in which the amount j t a le and obnoxious odor customarily foundwith a the insecticide. t a
• any such dithiophosphate ester for example, 0,0- dimethyl S (1,2 dicarbomethoxyethyl) phosphorodithioate, 0,0 dimethyl S (1,2 dicarbo n propoxyethyl) phosphorodithioate, 0,0 dimethyl S- l,2 dicarbisopropoxyethyl) phosphorodithioate, 0,0- die'thyl S (1,2 dicarbornethoxyethyl) phosphorodithioate, 0,0 diethyl S (1,2 dicarbethoxyethyD- phosphorodithioate, 0,0 diethyl S (1,2 dicarbon propoxyethyl) phosphorodithioate, 7 0,0 diethyl- S (1,2 dicarbisopropoxyethyl) phosphorodithioate,
• a process for reducing the objectionable odor of a malodorous phosphorodithioate compound which comprises subjecting said compound to the action of ozone 'in an amount from about 0.1 percent to about 3.5 percent by weight of said compound.
• a process for reducing the objectionable odor of a malodorous phosphorodithioate compound which comprises subjecting said compound to the action of a nonreactive gas containing ozone, the amount of ozone being 1 from about 0.1, percent to' about 3.5 percent by weight of said compound.
• R and R are each selected from the group:
• R and R are each selected from the group consisting of hydrogen, aliphatic and aromatic v hydrocarbon radicals whichcomprisessubjecting said compound to? the'actionof ozone in. 'an amount fromxabout 0.1..percent 4.
• a process as'in claim 3 in which said compound is -iri which RL-and-R areeach selectedfmm the group consisting of aliphatic and aromatic hydrocarbon radicals and R and R are each selected from the group consist- 6.
• R R R and R are each selected from the 2,57 52 Cassaday 1 1951 group consisting of aliphatic and aromatic hydrocarbons 2,344, 20 Escobar July 22, 195 which comprises subjecting said compound to the action 2,379 234 Too et 1 Man 24, 1959 of ozone in an amount from about 0.1 percent to about 10 3.5 percent by weight of said compound and subsequently OTHER REFERENCES passing an inert gas through the so-treated compound hackhs Chemical Dictionary, third edition, 1944, the to expel volatiles therefrom. Blakiston Co., Philadelphia, Pa., page 609.

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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)
• Luminescent Compositions (AREA)
• Treating Waste Gases (AREA)

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Cited By (7)

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Citations (3)

• 0
  • BE BE626519D patent/BE626519A/xx unknown
• 1959
  • 1959-06-16 US US820591A patent/US2980723A/en not_active Expired - Lifetime
• 1960
  • 1960-05-31 GB GB19195/60A patent/GB897332A/en not_active Expired
  • 1960-06-13 DE DEA34876A patent/DE1154094B/de active Pending

Patent Citations (3)

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