US2966524A - Process for the stabilization of chlorinated hydrocarbons - Google Patents

Process for the stabilization of chlorinated hydrocarbons Download PDF

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Publication number
US2966524A
US2966524A US838047A US83804759A US2966524A US 2966524 A US2966524 A US 2966524A US 838047 A US838047 A US 838047A US 83804759 A US83804759 A US 83804759A US 2966524 A US2966524 A US 2966524A
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US
United States
Prior art keywords
primary
picoline
stabilization
chloroethylene
gram
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Expired - Lifetime
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US838047A
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English (en)
Inventor
Daras Nestor
Ryckaert Andre
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Solvay SA
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Solvay SA
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C23—COATING 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
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/028—Cleaning 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
    • C23G5/02854—Cleaning 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
    • C23G5/02883—Nitrogen-containing compounds
    • C23G5/0289—N-heterocyclics
    • 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

  • the present invention concerns a process for stabilizing chlorinated hydrocarbons, particularly perchlorethylene, with a view to avoiding decomposition of these products and the simultaneous formation of acid during storage or when being used.
  • chlorinated hydrocarbons undergo an oxidation which is catalyzed by different agents such as light and certain metal salts such as salts of aluminum, iron and magneslum.
  • the present invention concerns a new combination of reagents for stabilizing chlorinated hydrocarbons, such combination giving surprising results.
  • chlorinated hydrocarbons and particularly perchlorethylene are stabilized by adding thereto small quantities of a primary pentanol or a mixture of primary pentanols and of a nitrogen base chosen from the group comprising pyridine, a-picoline (Z-methylpyridine) and morpholine (tetrahydro-l,4-oxazine).
  • u-Picoline is preferably used.
  • the primary pentanols there may be cited: primary n-amyl alcohol, primary isoamyl alcohol (3-methyl-2-butanol), and primary active amyl alcohol (2 methyl-l-butanol).
  • An example of a mixture of primary pentanols is fermentation amyl alcohol which contains essentially primary isoamyl alcohol and primary active amyl alcohol.
  • Oxygen is bubbled through the perchlorethylene by means of a thin tube of 3 mm. inside diameter, extending into the flask to within 6 mm. of the bottom.
  • a steel test-bar is suspended from said tube, at the base of the 2,966,524 Patented Dec. 27, 1960 cooler; another, smaller, is placed at the bottom of the flask.
  • the flow of oxygen is regulated to from 10 to 12 bubbles per minute, by means of a tube extending into a water valve. apparatus.
  • the perchlorethylene is heated to boiling and kept boiling with reflux for 48 hours by means of a w. frosted glass incandescent lamp, fixed in a stainless steel cylinder of mm. height and 100 mm. inside diameter.
  • the steel wall of said cylinder is 1 mm. thick.
  • On the top of this cylinder there is mounted a ring of 132 mm. outside diameter, 82 mm. inside diameter and 2 mm. thickness.
  • the bottom of the flask, resting on this ring is thus 30 mm. from the lamp.
  • Four diametrically opposed openings, 40 mm. high and 20 mm. wide, are provided This bubbler is placed upstream of the test in the lower part of the cylinder in order to ensure suitable ventilation of the apparatus. 7
  • the apparatus should be heat insulated.
  • the Erlenmeyer flask is surrounded by a covering constituted by a glass cylinder, of 121 mm. inside diameter, 147 mm. height and 3 mm. thickness, lined inside and outside with asbestos paper and filled with glass wool.
  • the assembly is covered with a square piece of asbestos-board provided with a central hole for the neck of the flask. This heat insulation reduces the losses of heat to a minimum, thus enabling regular boiling of the perchlorethylene and improving reproduction of the results.
  • Acidity in Percent by Test No. Stabilizer ing/l. weight of HCl formed 0. 0640 500 0. 0068 500 0.0280 500 0.0220 500 0. 0126 6 a-PiCOlil'lO 100 0. 0140 7. Mornhnlinp 100 0.0261 8 Pyridine 100 0.0288
  • the quantity of stabilizing material to be used in the process according to the present invention may generally be from 0.1 to g. of primary pentanol and from 0.05 to 0.5 g. of nitrogen bases, per liter of chlorinated hydrocarbon to be stabilized. Preferably there will be used 0.3 to 2 g. of pentanol and 0.1 to 0.2 g. of nitrogen base per liter of chlorinated hydrocarbon.
  • compositions described above show themselves to be particularly efficient in the stabilization of perchlorethylene, they can also be used for the stabilization of other chlorinated solvents such as trichlorethylene, carbon tetrachloride, dichlorethane, trichlorethane, etc.
  • a process for the stabilization of a chloroethylene which comprises incorporating in said chloroethylene per liter thereof 0.1 to 10 grams of a primary pentanol and 0.05 to 0.5 gram of a nitrogen base selected from the group consisting of morpholine, pyridine, and picoline.
  • a process for the stabilization of a chloroethylene which comprises incorporating in said chloroethylene per liter thereof 0.1 to 10 grams of a primary pentanol selected from the group consisting of normal amyl alcohol, primary active amyl alcohol, and primary isoamyl alcohol, and 0.05 to 0.5 gram of a nitrogen base selected from the group consisting of morpholine, pyridine, and picoline.
  • a process for the stabilization of a chloroethylene which comprises incorporating in said chloroethylene per liter thereof 0.1 to 10 grams of a primary pentanol and 0.05 to 0.5 gram of picoline.
  • a process for the stabilization of a chloroethylene which comprises incorporating in said chloroethylene per liter thereof 0.1 to 10 grams of normal amyl alcohol and 0.05 to 0.5 gram of picoline.
  • a process for the stabilization of a chloroethylene which comprises incorporating in said chloroethylene per liter thereof 0.1 to 10 grams of a primary pentanol and 0.05 to 0.5 gram of a nitrogen base selected from the group consisting of morpholine, pyridine, and picoline, and 0.005 to 0.02 gram of phenol.
  • a process for the stabilization of a perchloroethylene which comprises incorporating in said perchloroethylene per liter thereof 0.1 to 10 grams of a primary pentanol and 0.05 to 0.5 gram of a nitrogen base selected from the group consisting of morpholine, pyridine, and picoline.
  • a stabilized composition comprising a chloroethylene normally subject to degradation and per liter thereof 0.1 to 10 grams of a primary pentanol and 0.05 to 0.5 gram of a nitrogen base selected from the group consisting of morpholine, pyridine, and picoline.
  • a stabilized composition comprising a chloroethylene normally subject to degradation and per liter thereof 0.1 to 10 grams of a primary pentanol selected from the group consisting of normal amyl alcohol, primary isoamyl alcohol, and 0.05 to 0.5 gram of a nitrogen base selected from the group consisting of morpholine, pyridine, and picoline.
  • a stabilized composition comprising a chloroethylene normally subject to degradation and per liter thereof 0.1 to 10 grams of a primary pentanol and 0.05 to 0.5 gram of picoline.
  • a stabilized composition comprising a chloroethylene normally subject to degradation and per liter thereof 0.1 to 10 grams of normal amyl alcohol and 0.05 to 0.5 gram of picoline.
  • a stabilized composition comprising a chloroethylene normally subject to degradation and per liter thereof 0.1 to 10 grams of a primary pentanol and 0.05 to 0.5 gram of a nitrogen base selected from the group consisting of morpholine, pyridine, and picoline and 0.005 to 0.02 gram of phenol.
  • a stabilized composition comprising a chloroethylene normally subject to degradation and per liter thereof 0.1 to 10 grams of a primary pentanol and 0.05 to 0.5 gram of a nitrogen base selected from the group consisting of morpholine, pyridine, and picoline.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US838047A 1958-09-10 1959-09-04 Process for the stabilization of chlorinated hydrocarbons Expired - Lifetime US2966524A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BE451933 1958-09-10

Publications (1)

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US2966524A true US2966524A (en) 1960-12-27

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US838047A Expired - Lifetime US2966524A (en) 1958-09-10 1959-09-04 Process for the stabilization of chlorinated hydrocarbons

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US (1) US2966524A (en(2012))
BE (1) BE571104A (en(2012))
CH (1) CH386404A (en(2012))
DE (1) DE1115237B (en(2012))
ES (1) ES251692A1 (en(2012))
FR (1) FR1234929A (en(2012))
NL (1) NL101709C (en(2012))

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB493875A (en) * 1937-04-16 1938-10-17 John William Croom Crawford Stabilisation of chlorinated hydrocarbons
GB551584A (en) * 1941-08-25 1943-03-02 Distillers Co Yeast Ltd Improvements in or relating to the stabilisation of vinylidene chloride
US2338297A (en) * 1938-10-19 1944-01-04 Mugdan Martin Process for polymerizing trichlorethylene
US2371644A (en) * 1942-10-01 1945-03-20 Westvaco Chlorine Products Cor Degreasing process

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB493875A (en) * 1937-04-16 1938-10-17 John William Croom Crawford Stabilisation of chlorinated hydrocarbons
US2338297A (en) * 1938-10-19 1944-01-04 Mugdan Martin Process for polymerizing trichlorethylene
GB551584A (en) * 1941-08-25 1943-03-02 Distillers Co Yeast Ltd Improvements in or relating to the stabilisation of vinylidene chloride
US2371644A (en) * 1942-10-01 1945-03-20 Westvaco Chlorine Products Cor Degreasing process

Also Published As

Publication number Publication date
CH386404A (fr) 1965-01-15
DE1115237B (de) 1961-10-19
ES251692A1 (es) 1959-11-16
FR1234929A (fr) 1960-07-01
NL101709C (en(2012))
BE571104A (en(2012))

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