US3723331A - Stabilization of saturated halogenated aliphatic hydrocarbons - Google Patents

Stabilization of saturated halogenated aliphatic hydrocarbons Download PDF

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Publication number
US3723331A
US3723331A US00120739A US3723331DA US3723331A US 3723331 A US3723331 A US 3723331A US 00120739 A US00120739 A US 00120739A US 3723331D A US3723331D A US 3723331DA US 3723331 A US3723331 A US 3723331A
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United States
Prior art keywords
percent
weight
trioxane
amount
range
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Expired - Lifetime
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US00120739A
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English (en)
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Y Correia
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Produits Chimiques Pechiney Saint Gobain
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Produits Chimiques Pechiney Saint Gobain
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/02Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
    • D06L1/04Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/38Separation; Purification; Stabilisation; Use of additives
    • C07C17/42Use of additives, e.g. for stabilisation
    • CCHEMISTRY; METALLURGY
    • C23COATING 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
    • C23GCLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/028Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
    • C23G5/02854Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons characterised by the stabilising or corrosion inhibiting additives
    • C23G5/02861Oxygen-containing compounds
    • C23G5/02877Ethers

Definitions

  • the present invention relates to the stabilization of halogenated aliphatic hydrocarbons saturated in C, to C, and particularly trichloro-l ,1 ,l ethane.
  • trioxane it is also known to use trioxane as a stabilizer.
  • the interval of stabilization time preceding the appearance 'of acid vapors or of a coloration varies from only minutes to 48 hours, which is insufficient for the prolonged use of trichloro-l,1,l ethane in degreasing or cleaning of metal or other objects.
  • the objective of this invention is to remedy the inconvenience cited above by allowing efficient and prolonged stabilization of the aliphatic halogenated hydrocarbons and thus the carrying out of the grease removal and/or cleaning of metal parts, plastics, textile or other materials, without noticing any degradation of the solvent and of the materials to be treated.
  • the stabilization of the aliphatic saturated halogenated solvents in C, to C, and particularly of trichloro-l,l,l ethane is accomplished by incorporating therein trioxane associated with an aliphatic alcohol, particularly tertio butanol and/or an epoxide which is liquid at ordinary temperature, particularly butylene oxide.
  • trioxane is associated with from 0.1 to 7.5 percent of said aliphatic alcohol and/or from 0.1 to 4 percent of said epoxide.
  • the combination is then incorporated into the halogenated solvent.
  • thiol such as alkyl orthoformate, alkyl orthoacetate, aliphatic or cyclic acetal, aliphatic organic acid
  • imino-ether such as N-alkyl alkoxy-l ethanimine and ketimine such as N- alkyl isopropanimine
  • an oxygen containing heterocyclic nucleus such as pyrannic heterocycle and/or a nitrogen containing heterocyclic nucleus such as pyrrolic, pyrrolinic and morpholinic heterocycle
  • the aforementioned alkyl groupings have from one to four carbon atoms and the boiling points of the compounds associated with trioxane and used in the stabilization formulas should not differ by more than 50, and preferably by not more than 25 C, from the boiling point of the halogenated saturated aliphatic hydrocarbon in question.
  • the foregoing materials may be associated with the trioxane in an amount within the range of 0.1 to 4 percent by weight and preferably in an amount within the range of 0.3 to 2 percent by weight, based upon the solvent composition.
  • the following list of compounds may be cited, but this list cannot be considered as limiting: dichloroethanes, trichloroethanes, and particularly trichloro-l, 1,1 ethane, tetrachloroethanes, dichloro-1,2 propane, dichloro-l,2 and -2,3 butanes, tribromo ethanes and dibromo-l ,2-propane.
  • the invention relates also to the stabilized compounds comprising one or several halogenated saturated aliphatic hydrocarbons in C, to C,, particularly trichloro-l,l ,1 ethane containing from 0.001 to 15 percent by weight of trioxane associated with 0.1 to 7.5 percent by weight of an aliphatic alcohol, particularly tertio butanol, and/or with 0.1 to 4 percent by weight of an expoxide liquid at ordinary temperature, particularly butylene oxide.
  • These compounds may also contain an alkyl nitrile in C, to C,, such as acetonitrile, propionitrile and butyronitrile, in an amount within the range of 0.1 to 4 percent by weight and preferably 0.3 to 2 percent by weight, and/or nitroalkane in C, to C,, such as nitromethane, nitroethane, nitropropane, and nitrobutane, in an amount within the range of 0.1 to 4 percent by weight and preferably 0.3 to 2 percent by weight.
  • an alkyl nitrile in C, to C such as acetonitrile, propionitrile and butyronitrile
  • nitroalkane in C, to C, such as nitromethane, nitroethane, nitropropane, and nitrobutane
  • 40 ml trichloro-1,l,l ethane are placed in a reflux condenser along with the stabilizer in the form of an aluminum plate of 99.9 percent purity, 1 mm thick, mm long and 12 mm wide. This plate is partly immersed into the trichloro-l,l,l ethane.
  • the heating time in the reflux condenser preceding the release of acid vapors and/or the buildup of a coloration of trichloro-l ,l ,1 ethane indicates the stabilization aptitude of the tested stabilizer combination.
  • compositions were prepared with 1,1,l-trichloroethane containing the components as set forth in the following table and the compositions were submitted to tests for stabilization as in Example 4.
  • a method for stabilizing halogenated saturated aliphatic hydrocarbon solvents having from one to four carbon atoms comprising the steps of forming a combination consisting essentially of trioxane, associated with at least one member selected from the group consisting of a lower alcohol and a liquid epoxide and adding said combination to the hydrocarbon, wherein 0.001 to 15 percent by weight of trioxane is associated with from 0.1 to 7.5 percent by weight of the alcohol when present and 0.1 to 4 percent by weight of the liquid epoxide when present.
  • halogenated hydrocarbon is selected from the group consisting of dichloroethanes, trichloroethanes, tetrachloroethanes, 1,2-dichloropropanes, 1,2-dichloro and 2,3-dichlorobutanes, tribromoethanes and 1,2- dibromopropane.
  • a stabilized composition consisting essentially of a halogenated saturated aliphatic hydrocarbon having from one to four carbon atoms containing from 0.001 to 15 percent by weight of trioxane and at least one member comprising from 0.1 to 7.5 percent by weight of a lower alcohol and from 0.1 to 4 percent by weight of a liquid epoxide.
  • composition as claimed in claim 9 containing in addition a compound selected from the group consisting of a C, to C, alkyl nitrile and a C, to C nitroalkane in which the compound is present in an amount within the range of 0.1 to 4 percent by weight.
  • composition asclaimed in claim in which the alkyl nitrile is acetonitrile and the nitroalkane is nitromethane.
  • a stabilized composition consisting essentially of a halogenated saturated C to C aliphatic hydrocarbon solvent stabilized with trioxane present in an amount within the range of 0.001 to l5 percent by weight, at least one of the members selected from the group consisting of a lower alcohol and a liquid epoxide and mixtures thereof in which the alcohol is present in an amount within the range of 0.1 to 7.5 percent by weight when present, and the liquid epoxide is present in an amount within the range of 0.1 to 4 percent by weight when present, and at least one compound selected from the group consisting of a C to C alkyl nitrile'and a C 1,2-dichloropropanes, 1,2-dichloro and 2,3- dichlorobutanes, tribromoethanes and 1,2- dibromopropane.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
US00120739A 1967-11-17 1971-03-03 Stabilization of saturated halogenated aliphatic hydrocarbons Expired - Lifetime US3723331A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR128693 1967-11-17
US12073971A 1971-03-03 1971-03-03

Publications (1)

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US3723331A true US3723331A (en) 1973-03-27

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US00120739A Expired - Lifetime US3723331A (en) 1967-11-17 1971-03-03 Stabilization of saturated halogenated aliphatic hydrocarbons

Country Status (7)

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US (1) US3723331A (de)
BE (1) BE719662A (de)
CH (1) CH489448A (de)
DE (1) DE1793235C3 (de)
FR (1) FR1567940A (de)
GB (1) GB1198583A (de)
NL (1) NL159647B (de)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3864413A (en) * 1970-01-22 1975-02-04 Norman L Beckers Stabilized metal chloroform
US4018837A (en) * 1972-08-16 1977-04-19 The Dow Chemical Company Stabilized methylchloroform
US4324757A (en) * 1979-07-02 1982-04-13 The Dow Chemical Company Halogenated hydrocarbons inhibited against denickelification with lower alkylcyanide compounds
US4973420A (en) * 1989-05-04 1990-11-27 Hoechst Celanese Corporation Stripper composition for removal of protective coatings
US6010997A (en) * 1998-06-25 2000-01-04 Alliedsignal Inc. Compositions of 1-bromopropane, nitromethane or acetonitrile and an alcohol
US6048832A (en) * 1998-06-25 2000-04-11 Alliedsignal Inc. Compositions of 1-bromopropane, 4-methoxy-1,1,1,2,2,3,3,4,4-nonafluorobutane and an organic solvent
US6103684A (en) * 1998-06-25 2000-08-15 Alliedsignal Inc. Compositions of 1-bromopropane and an organic solvent

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3694368A (en) * 1971-02-26 1972-09-26 Allied Chem Ternary azeotropic compositions
FR2437392A1 (fr) * 1978-06-30 1980-04-25 Rhone Poulenc Ind Stabilisation du trichloro-1,1,1 ethane

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3251891A (en) * 1962-01-18 1966-05-17 Pittsburgh Plate Glass Co Stabilized compositions
US3326988A (en) * 1964-07-13 1967-06-20 Pittsburgh Plate Glass Co Stabilized methyl chloroform compositions with improved evaporation characteristics
US3564061A (en) * 1965-08-17 1971-02-16 Pechiney Saint Gobain Stabilization of halogenated solvents
US3564063A (en) * 1958-02-03 1971-02-16 Ppg Industries Inc Stabilized methylchloroform compositions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3564063A (en) * 1958-02-03 1971-02-16 Ppg Industries Inc Stabilized methylchloroform compositions
US3251891A (en) * 1962-01-18 1966-05-17 Pittsburgh Plate Glass Co Stabilized compositions
US3326988A (en) * 1964-07-13 1967-06-20 Pittsburgh Plate Glass Co Stabilized methyl chloroform compositions with improved evaporation characteristics
US3564061A (en) * 1965-08-17 1971-02-16 Pechiney Saint Gobain Stabilization of halogenated solvents

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3864413A (en) * 1970-01-22 1975-02-04 Norman L Beckers Stabilized metal chloroform
US4018837A (en) * 1972-08-16 1977-04-19 The Dow Chemical Company Stabilized methylchloroform
US4324757A (en) * 1979-07-02 1982-04-13 The Dow Chemical Company Halogenated hydrocarbons inhibited against denickelification with lower alkylcyanide compounds
US4973420A (en) * 1989-05-04 1990-11-27 Hoechst Celanese Corporation Stripper composition for removal of protective coatings
US6010997A (en) * 1998-06-25 2000-01-04 Alliedsignal Inc. Compositions of 1-bromopropane, nitromethane or acetonitrile and an alcohol
US6048832A (en) * 1998-06-25 2000-04-11 Alliedsignal Inc. Compositions of 1-bromopropane, 4-methoxy-1,1,1,2,2,3,3,4,4-nonafluorobutane and an organic solvent
US6103684A (en) * 1998-06-25 2000-08-15 Alliedsignal Inc. Compositions of 1-bromopropane and an organic solvent
US6365565B1 (en) 1998-06-25 2002-04-02 Honeywell International Inc. Compositions of 1-bromopropane and an organic solvent

Also Published As

Publication number Publication date
NL6811831A (de) 1969-05-20
DE1793235C3 (de) 1979-10-04
DE1793235A1 (de) 1971-12-16
CH489448A (fr) 1970-04-30
GB1198583A (en) 1970-07-15
NL159647B (nl) 1979-03-15
DE1793235B2 (de) 1979-02-15
FR1567940A (de) 1969-05-23
BE719662A (de) 1969-02-19

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