US3364270A - Stabilization of methyl chloroform - Google Patents

Stabilization of methyl chloroform Download PDF

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Publication number
US3364270A
US3364270A US505419A US50541965A US3364270A US 3364270 A US3364270 A US 3364270A US 505419 A US505419 A US 505419A US 50541965 A US50541965 A US 50541965A US 3364270 A US3364270 A US 3364270A
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Prior art keywords
methyl chloroform
stabilization
cyano
benzaldehyde
percent
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US505419A
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Milton J Blankenship
Mccarthy Ralph
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Dow Chemical Co
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Dow Chemical Co
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    • 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 the stabilization of methyl chloroform. More particularly, the present invention relates to the stabilization of methyl chloroform in the presence of aluminum.
  • this reaction may be substantially retarded or prevented by incorporating an inhibiting amount of a cyano-benzaldehyde compound into the methyl chloroform.
  • Ortha-, paraand meta-cyanobenzaldehyde may each be used alone or in any combination. Only an amount of cyano benzaldehyde compound sufiicient to retard or stop the reaction of aluminum and methyl chloroform is required. Ordinarily, amounts of from about 0.5 to 1015 percent by weight (based on the total weight of the composition) of cyano-benzaldehyde compound may be incorporated into the methyl chloroform.
  • the preferred concentration of cyano-benzaldehyde compound in the methyl chloroform is from about 1.0 to 5.0 percent by weight (based on the total weight of the composition).
  • cyano-benzaldehyde inhibitor compounds of the invention may be used alone or in combination with other non-reactive conventional inhibitors. Such cyanobenzaldehyde compounds are superior inhibitors when compared with related aldehydes, such as benzaldehyde.
  • Examples 1 and II 'Dilferent amounts of cyano-benzaldehyde compounds were added to 10 milliliter samples of 1,1,l-trichloroethane. Concentrations were calculated as weight percents.
  • An aluminum coupon [designated alloy 1100, 18 gage 0.20 percent Cu (maximum) 0.05 percent Mn (maximum) 0.1
  • a composition inhibited against attack by aluminum which comprises methyl chloroform and an inhibiting amount of a cyano-benzaldehyde.
  • An inhibited composition according to claim 1 which contains 0.5 to 15 percent by weight of ortho-cyano'benzaldehyde.
  • An inhibited composition according to claim 1 which contains 0.5 to 15 percent by weight of para-cyano-benzaldehyde.
  • An inhibited composition according to claim 1 which contains 0.5 to 15 percent by weight of meta-cyano-benzaldehyde.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

United States Patent 3,364,270 STABILIZATION OF METHYL 'CHLOROFORM Milton 3. Blankenship, Midland, and Ralph McCarthy,
Bay City, Mich, assignors to The Dow Chemical Company, Midland, Mich, a corporation of Delaware No Drawing. Filed Oct. 27, 1965, Ser. No. 505,419 4 Claims. (Cl. 260-6525) ABSTRACT OF THE DESCLGSURE Methyl chloroform is stabilized in the presence of aluminum by incorporating in the solvent an inhibiting amount of a cyanobenzaldehyde.
This invention relates to the stabilization of methyl chloroform. More particularly, the present invention relates to the stabilization of methyl chloroform in the presence of aluminum.
It is known that methyl chloroform reacts violently with aluminum to form tars and gaseous reaction products.
It has now been found that this reaction may be substantially retarded or prevented by incorporating an inhibiting amount of a cyano-benzaldehyde compound into the methyl chloroform. Ortha-, paraand meta-cyanobenzaldehyde may each be used alone or in any combination. Only an amount of cyano benzaldehyde compound sufiicient to retard or stop the reaction of aluminum and methyl chloroform is required. Ordinarily, amounts of from about 0.5 to 1015 percent by weight (based on the total weight of the composition) of cyano-benzaldehyde compound may be incorporated into the methyl chloroform. The preferred concentration of cyano-benzaldehyde compound in the methyl chloroform is from about 1.0 to 5.0 percent by weight (based on the total weight of the composition).
The cyano-benzaldehyde inhibitor compounds of the invention may be used alone or in combination with other non-reactive conventional inhibitors. Such cyanobenzaldehyde compounds are superior inhibitors when compared with related aldehydes, such as benzaldehyde.
The following examples are submitted for the purpose of illustration only and are not to be construed as limiting the scope of the invention in any way.
Examples 1 and II 'Dilferent amounts of cyano-benzaldehyde compounds were added to 10 milliliter samples of 1,1,l-trichloroethane. Concentrations were calculated as weight percents. An aluminum coupon [designated alloy 1100, 18 gage 0.20 percent Cu (maximum) 0.05 percent Mn (maximum) 0.1
2. 3. 4. 5. 0 percent Zn (maximum) "ice (approximately 0.04 to 0.05 inch thick by 2 /2 inches by /2 inch)] was immersed in each test solution and scratched with a sharp tool beneath the surface of the test liquid. The coupon was observed visually and the results recorded in Table 1 according to the following standards:
Key number: Indicated result We claim as our invention:
1. A composition inhibited against attack by aluminum which comprises methyl chloroform and an inhibiting amount of a cyano-benzaldehyde.
2. An inhibited composition according to claim 1 which contains 0.5 to 15 percent by weight of ortho-cyano'benzaldehyde.
3. An inhibited composition according to claim 1 which contains 0.5 to 15 percent by weight of para-cyano-benzaldehyde.
4. An inhibited composition according to claim 1 which contains 0.5 to 15 percent by weight of meta-cyano-benzaldehyde.
References Cited UNITED STATES .PATENTS 2,997,507 8/1961 Monroe et al 260652.5 3,128,315 4/1964 Hardies 260652.5
OTHER REFERENCES Every et al.: Materials Protection, vol. 3 (9), pp. 46 and 47 (1964).
LEON ZITVER, Primary Examiner.
M. JACOB, Assistant Examiner.
US505419A 1965-10-27 1965-10-27 Stabilization of methyl chloroform Expired - Lifetime US3364270A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3444247A (en) * 1967-12-01 1969-05-13 Dow Chemical Co Stabilization of 1,1,1-trichloroethane

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2997507A (en) * 1958-12-03 1961-08-22 Dow Chemical Co Metallic corrosion inhibition of polyhalogenated hydrocarbons with propargyldiisopropylamine
US3128315A (en) * 1961-03-13 1964-04-07 Pittsburgh Plate Glass Co Methylchloroform stabilized with dialkylethers of alkylene glycols

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2997507A (en) * 1958-12-03 1961-08-22 Dow Chemical Co Metallic corrosion inhibition of polyhalogenated hydrocarbons with propargyldiisopropylamine
US3128315A (en) * 1961-03-13 1964-04-07 Pittsburgh Plate Glass Co Methylchloroform stabilized with dialkylethers of alkylene glycols

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3444247A (en) * 1967-12-01 1969-05-13 Dow Chemical Co Stabilization of 1,1,1-trichloroethane

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