US3551505A - Stabilized chlorinated hydrocarbon - Google Patents

Stabilized chlorinated hydrocarbon Download PDF

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Publication number
US3551505A
US3551505A US791486*A US3551505DA US3551505A US 3551505 A US3551505 A US 3551505A US 3551505D A US3551505D A US 3551505DA US 3551505 A US3551505 A US 3551505A
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US
United States
Prior art keywords
chlorinated hydrocarbon
diaziridine
stabilizing
stabilized
group
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
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US791486*A
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English (en)
Inventor
Andre Ryckaert
Julien Mulders
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Solvay SA
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Solvay SA
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Publication date
Application filed by Solvay SA filed Critical Solvay SA
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Publication of US3551505A publication Critical patent/US3551505A/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/42—Use of additives, e.g. for stabilisation

Definitions

  • This invention relates to a process for stabilizing chlorinated hydrocarbons and to the stabilized chlorinated hydrocarbon composition. More particularly, the present invention is directed to an improvement over the process for stabilizing chlorinated hydrocarbons described in Canadian Pat. No. 792,807 which issued onAug. 20, 1968 which corresponds to U.S. patent application Ser. No. 676,620, filed Oct. 19, 1967, now Pat. No. 3,479,414, and which is assigned to Solvay et Cie.
  • alkyl derivative thereof such as 1,2-diethyl diaziridine. It is specified in the patent, that combinations of the above compounds may be used as stabilizers; similarly, diaziridine or its alkyl derivatives may be used with other known stabilizing agents.
  • N- alkyl derivatives of pyrrole for example, N-methylpyrrole or N-ethylpyrrole
  • the stabilizing amounts should be comprised between 0.001 and 1% by weight.
  • the present invention is directed to a process for stabilizing chlorinated hydrocarbons by the addition of N- heterocyclic compounds selected from the group consisting of diaziridine and/ or alkyl derivatives thereof, according to U.S. patent application No. 676,620, now Pat. No. 3,479,414, in which there is used simultaneously a co-stabilizer having a synergistic effect, comprising one or more bases having a pyrrole nucleus, such as pyrrole or the N- alkyl derivatives.
  • the present invention is also directed to stabilized chlorinated hydrocarbon containing both of these stabilizing compounds.
  • the stabilizing amounts of diaziridine or the alkyl derivatives thereof and of the bases having a pyrrole nucleus "ice are each preferably comprised between 0.025 and 0.5 gper liter of chlorinated hydrocarbon.
  • diaziridine and/or N,N-dialkyldiaziridine in which the alkyl groups contain 1 to 3 carbon atoms.
  • the combination of the aforementioned diaziridine compound and pyrrole and/ or N-alkylpyrrole, most preferably wherein the alkyl group contains 1 to 3 carbon atoms yields a chlorinated hydrocarbon composition of exceptional stability.
  • the invention is not limited to the above specific examples with respect to the nature of the co-stabilizers and the amounts utilized. Similarly, the invention may be used not only for the stabilization of trichloroethylene, but also for the stabilization of perchloroethylene, carbon tetrachloride, dichloroethanes, trichloroethanes and other analogous chlorinated solvents, as well as mixtures of such solvents.
  • a plurality of stabilizers of the diaziridine group and/or of the group comprising bases having pyrrole nucleus may be used.
  • other stabilizers which are well known may be used simultaneously as those according to the present invention.
  • Stabilized chlorinated hydrocarbon composition wherein said chlorinated hydrocarbon is selected from the group consisting of perchloroethylene, trichloroethylene, carbon tetrachloride, a dichloroethane, a trichloroethane and mixtures thereof containing a heterocyclic compound selected from the group consisting of diaziridine, a lower alkyl diaziridine and mixtures thereof in a stabilizing amount of about 0.025 to 0.5 g. per liter of said chlorinated hydrocarbon, and a base selected from the group consisting of pyrrole, and N-alkylpyrrole wherein the alkyl group contains 1 to 3 carbon atoms in a stabilizing amount of about 0.025 to 5 g. per liter of said chlorinated hydrocarbon.
  • Stabilized chlorinated hydrocarbon according to claim 1 containing a synergistic stabilizing composition consisting of at least one compound selected from the group consisting of diaziridine and N,N-dialkyldiaziridine 4 wherein the alkyl group contains 1 to 3 carbon atoms and 3,269,953 8/1966 Boothman 260652.5 at least one compound selected from the group consisting 3,314,892 4/1967 Graham II 260652.5X of pyrrole and N-alkylpyrrole wherein the alkyl group 3,328,474 6/1967 Blankenship 260-6525 contains 1 to 3 carbon atoms. 3,397,246 8/ 1968 Ryckaert et a1 260652.5 3.
  • a synergistic stabilizing composition consisting of at least one compound selected from the group consisting of diaziridine and N,N-dialkyldiaziridine 4 wherein the alkyl group contains 1 to 3 carbon atoms and 3,269,953 8/1966

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US791486*A 1968-01-17 1969-01-15 Stabilized chlorinated hydrocarbon Expired - Lifetime US3551505A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BE53435 1968-01-17

Publications (1)

Publication Number Publication Date
US3551505A true US3551505A (en) 1970-12-29

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ID=3840863

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US791486*A Expired - Lifetime US3551505A (en) 1968-01-17 1969-01-15 Stabilized chlorinated hydrocarbon

Country Status (5)

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US (1) US3551505A (fr)
AT (1) AT287660B (fr)
CA (1) CA937583A (fr)
DE (1) DE1816390A1 (fr)
FR (1) FR2000321A6 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4293433A (en) * 1980-06-02 1981-10-06 Diamond Shamrock Corporation Perchloroethylene dielectric fluid containing pyrrole and phenol

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4293433A (en) * 1980-06-02 1981-10-06 Diamond Shamrock Corporation Perchloroethylene dielectric fluid containing pyrrole and phenol

Also Published As

Publication number Publication date
CA937583A (en) 1973-11-27
FR2000321A6 (fr) 1969-09-05
DE1816390A1 (de) 1969-08-21
AT287660B (de) 1971-02-10

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