US3049571A - Stabilized degreasing solvent - Google Patents

Stabilized degreasing solvent Download PDF

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Publication number
US3049571A
US3049571A US15821A US1582160A US3049571A US 3049571 A US3049571 A US 3049571A US 15821 A US15821 A US 15821A US 1582160 A US1582160 A US 1582160A US 3049571 A US3049571 A US 3049571A
Authority
US
United States
Prior art keywords
methyl chloroform
solvent
zinc
percent
dioxane
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
Application number
US15821A
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English (en)
Inventor
Winston E Brown
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Chemical Co
Original Assignee
Dow Chemical Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to NL261754D priority Critical patent/NL261754A/xx
Priority to NL113941D priority patent/NL113941C/xx
Application filed by Dow Chemical Co filed Critical Dow Chemical Co
Priority to US15821A priority patent/US3049571A/en
Priority to DED35049A priority patent/DE1173306B/de
Priority to GB868/61A priority patent/GB916129A/en
Priority to FR855774A priority patent/FR1284254A/fr
Application granted granted Critical
Publication of US3049571A publication Critical patent/US3049571A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C23G5/02861—Oxygen-containing compounds
    • C23G5/0288—Epoxy compounds
    • 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 solvent comprising methyl chloroform containing a mixture of inhibitors effective to prevent decomposition of the methyl chloroform when the vapors thereof are in contact with metallic zinc surfaces and to prevent corrosion of the zinc and zinc alloys.
  • Methyl chloroform is recognized as an excellent solvent and there has been a continuing need to render it inert to the presence of metals under the conditions of vapor degreasing.
  • Stabilizers are known which are effective in stabilizing methyl chloroform against decomposition induced by contact with iron and aluminum even at elevated temperatures. It is now known, however, that while pure uninhibited methyl chloroform at elevated temperatures is relatively inert to the presence of zinc, methyl chloroform which is stabilized against decomposition due to contact with other metals, particularly iron and aluminum, tends to decompose badly in the presence of zinc and cause substantial corrosive attack on the Zinc metal.
  • Methyl chloroform may be used in the cold degreasing of metals until it becomes saturated with dirt, grease and other impurities from the metal being cleaned.
  • Spent solvent without the stabilizer system hereinafter proposed cannot be recovered by distillation in the zinc-lined stills commonly used in the industry without damage to the lining thereof.
  • Methyl chloroform where used as a vapor degreasing solvent contains minor amounts of certain additives or stabilizers to prevent decomposition of the solvent induced by its contact with metals such as aluminum and iron.
  • Inhibitors such as 1,4-di0xane alone or in combination with nitromethane, secondary butyl alcohol, or monohydric acetylenic alcohols are commonly employed.
  • stabilizers are quite effective in rendering the solvent inert to attack of the metal by the degradation products, but greatly increase the ability of zinc, in the boiling solvent vapors, to cause degradation of the solvent and concomitantly increased attack of the metal.
  • This undesirable property of the solvent may be eliminated, however, by the addition thereto of a vicinal inonoepoxide in the amount of from about 0.01 to 5.0 percent by Weight of the solvent mixture. It is preferred to employ the epoxide in the amount of from about 0.10 to 1.5 percent by Weight, however. If an amount less than 0.01 percent is employed no effective stabilization is achieved. Amounts greater than 5 percent may be employed but no advantage is achieved thereby.
  • Vicinal epoxides refers to aliphatic epoxides containing an ethylene oxide group. While many vicinal monoepoxides are operable to some extent it is desirable to employ vicinal monoepoxides containing from 4 to 6 carbon atoms, for example, 1,2-butylene oxide, isobutylene oxide, cis-2,3- and trans-2,3-butylene oxide, 3,4- epoxybutene transand cis-2,3-pentene oxide, Z-methyl- 2,3-epoxybutane, 1,2-epoxycyclopentene and 2,3-dimethyl2,3epoxybutane.
  • 1,2-butylene oxide isobutylene oxide
  • cis-2,3- and trans-2,3-butylene oxide 3,4- epoxybutene transand cis-2,3-pentene oxide
  • Z-methyl- 2,3-epoxybutane 1,2-epoxycyclopentene and 2,3-dimethyl2,3ep
  • Example 1 To demonstrate the relative stability of uninhibited methyl chloroform to zinc a test run was made as follows:
  • a flask was partly filled with uninhibited methyl chloformed due to decomposition of the solvent and ZnCl formed by corrosive action of the solvent on the zinc.
  • Example 2 In the same equipment, and under the same conditions employed in Example 1, a sample (1) of methyl chloroform containing 4 percent by Weight of 1,4-dioxane, a sample (2) of methyl chloroform containing 4 percent by weight of 1,4-dioxane and 0.05 percent by weight of secondary butyl alcohol and a sample (3) of methyl chloroform containing 4 percent by weight of 1,4-dioxane and 0.5 percent by weight of nitromethane were boiled for seven days. The test strips in every case were found to be badly corroded. The methyl chloroform, sample (1) was found to contain 110 p.p.m. chloride, sample (2) Was found to contain 150 p.p.m. chloride, and sample (3) was found to contain p.p.m. chloride. However, the zinc strips in sample (3) were corroded more severely than in the other two test strips.
  • Example 3 In the same equipment and under the same conditions employed in Example 1, samples of methyl chloroform were tested employing vicinal monoepoxides in combination With various stabilizers as shown in the following table:
  • composition of matter comprising methyl chloroform containing a minor amount of 1,4-dioxane and having dissolved therein a stabilizing amount of a vicinal monoepoxide having from 4 to 6 carbon atoms.
  • a composition of matter comprising methyl chloroform containing a minor amount of 1,4-dioxane and a minor amount of a compound selected from the group consisting of nitromethane, secondary butyl alcohol and a lower monohydric acetylenic alcohol and having dissolved therein a stabilizing amount of a vicinal aliphatic monoepoxide having from 4 to 6 carbon atoms.
  • composition of matter comprising methyl chloroform containing a minor amount of nitromethane and dissolved therein a stabilizing amount of a vicinal monoepoxide having from 4 to 6 carbon atoms.
  • composition of matter comprising methyl chloroform containing a minor amount of secondary butyl alcohol and having dissolved therein a stabilizing amount of a vicinal monoepoxide having from 4 to 6 carbon atoms.
  • a vapor degreasing solvent composition comprising methyl chloroform containing a small stabilizing amount of 1,4-dioxane and having dissolved therein from 0.05 to 5 percent by Weight of a vicinal monoepoxide having from 4 to 6 carbon atoms.
  • a vapor degreasing solvent composition comprising methyl chloroform containing stabilizing amounts of 1,4- dioxane and nitromethane and having dissolved therein from 0.05 to 5 percent by weight of a vicinal monoepoxide having from 4 to 6 carbon atoms.
  • a vapor degreasing solvent composition comprising methyl chloroform containing stabilizing amounts of 1,4- dioxane and secondary butyl alcohol having dissolved therein from 0.05 to 5 percent by weight of a vicinal monoepoxide having from 4 to 6 carbon atoms.
  • a vapor degreasing solvent composition comprising methyl chloroform containing stabilizing amounts of 1,4- dioxane and a monohydric acetylene alcohol having dissolved therein from 0.05 to 5 percent by weight of a vicinal monoepoxide having from 4 to 6 carbon atoms.
  • composition of matter comprising methyl chloroform containing a stabilizing amount of 1,4-dioxane and from 0.10 to 1.5 percent by weight butylene oxide.
  • composition of matter comprising methyl chlorofor-m containing a stabilizing amount of 1,4-dioxane and from 0.10 to 1.5 weight percent of amylene oxide.
  • composition of matter comprising methyl chloroform containing a stabilizing amount of 1,4-dioxane and from 0.10 to 1.5 weight percent of hexylene oxide.
  • composition of matter comprising methyl chloroform containing a stabilizing amount of nitrornethane and from 0.10 to 1.5 weight percent of butylene oxide.
  • a composition of matter comprising methyl chloroform containing a stabilizing amount of nitromethane and from 0.10 to 1.5 weight percent of amylene oxide.
  • composition of matter comprising methyl chloroform containing a stabilizing amount of secondary butyl alcohol and from 0.10 to 1.5 weight percent of butylene oxide.
  • a composition of matter comprising methyl chloroform containing a stabilizing amount of a secondary butyl alcohol and from 0.10 to 1.5 weight percent of amylene oxide.
  • composition of matter comprising methyl chloroform containing a stabilizing amount of secondary butyl alcohol and from 0.10 to 1.5 weight percent of hexylene oxide.

Landscapes

  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
US15821A 1960-03-18 1960-03-18 Stabilized degreasing solvent Expired - Lifetime US3049571A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
NL261754D NL261754A (de) 1960-03-18
NL113941D NL113941C (de) 1960-03-18
US15821A US3049571A (en) 1960-03-18 1960-03-18 Stabilized degreasing solvent
DED35049A DE1173306B (de) 1960-03-18 1960-12-27 Gegen Zersetzung bei Beruehrung mit Metallen stabilisiertes 1, 1, 1-Trichloraethan
GB868/61A GB916129A (en) 1960-03-18 1961-01-09 Stabilized methyl chloroform
FR855774A FR1284254A (fr) 1960-03-18 1961-03-16 Solvant dégraissant stabilisé

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US15821A US3049571A (en) 1960-03-18 1960-03-18 Stabilized degreasing solvent

Publications (1)

Publication Number Publication Date
US3049571A true US3049571A (en) 1962-08-14

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ID=21773819

Family Applications (1)

Application Number Title Priority Date Filing Date
US15821A Expired - Lifetime US3049571A (en) 1960-03-18 1960-03-18 Stabilized degreasing solvent

Country Status (5)

Country Link
US (1) US3049571A (de)
DE (1) DE1173306B (de)
FR (1) FR1284254A (de)
GB (1) GB916129A (de)
NL (2) NL261754A (de)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3281480A (en) * 1961-08-09 1966-10-25 Pittsburgh Plate Glass Co Stabilization of methyl chloroform
DE1246702B (de) * 1962-10-18 1967-08-10 Dynamit Nobel Ag Stabilisierung von 1, 1, 1-Trichloraethan
US3536766A (en) * 1968-12-26 1970-10-27 Dow Chemical Co Stabilized methyl chloroform composition
US3681469A (en) * 1970-09-21 1972-08-01 Dow Chemical Co Stabilization of 1,1,1-trichloroethane
US3878256A (en) * 1962-10-18 1975-04-15 Dynamit Nobel Ag Stabilization of 1,1,1-trichloroethane with a four component system
US3959397A (en) * 1962-10-18 1976-05-25 Dynamit Nobel Aktiengesellschaft Stabilization of 1,1,1-trichloroethane with a three component system
US4069265A (en) * 1962-10-18 1978-01-17 Dynamit Nobel Aktiengesellschaft Stabilization of 1,1,1-trichloroethane with a four component system
EP0044111A1 (de) * 1980-07-15 1982-01-20 SOLVAY & Cie (Société Anonyme) Stabilisierte 1,1,1-Trichlorethanzusammensetzungen
US4327232A (en) * 1981-02-19 1982-04-27 The Dow Chemical Company Cyclopropane ring-containing compounds as inhibitor components in methylchloroform
US4351973A (en) * 1980-10-06 1982-09-28 The Dow Chemical Company Stabilized methylchloroform
FR2503697A1 (fr) * 1981-04-13 1982-10-15 Solvay Compositions stabilisees de 1,1,1-trichloroethane
US4356038A (en) * 1979-07-25 1982-10-26 Imperial Chemical Industries Limited Stabilization of chlorinated aliphatic hydrocarbons and use of stabilized composition in cleaning articles
US4394284A (en) * 1981-02-03 1983-07-19 The Dow Chemical Company Stabilized methylchloroform composition
US4597890A (en) * 1985-02-15 1986-07-01 The Dow Chemical Company Solvent blend for removing flux residues
US5759985A (en) * 1995-07-21 1998-06-02 Advanced Chemical Design, Inc. Compositions for the stabilization of bromochloromethane
US5801136A (en) * 1994-08-19 1998-09-01 Advanced Chemical Design, Inc. Stabilized solvents and method for cleaning metallic, electrical and plastic substrates utilizing environmentally safe solvent materials

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA737892A (en) * 1963-12-12 1966-07-05 W. Bauer Albert Cleaning composition
CA1008087A (en) * 1972-08-16 1977-04-05 Wesley L. Archer Stabilized methylchloroform
DE2717322A1 (de) * 1977-04-19 1978-10-26 Wacker Chemie Gmbh Stabilisiertes von 1,1,1-trichloraethan

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2371645A (en) * 1943-09-16 1945-03-20 Westvaco Chlorine Products Cor Degreasing process
GB773187A (en) * 1955-12-08 1957-04-24 Hoechst Ag Method of stabilizing halogenated methanes
US2811252A (en) * 1954-03-30 1957-10-29 Dow Chemical Co Methyl chloroform inhibited with dioxane
US2838458A (en) * 1955-09-30 1958-06-10 Dow Chemical Co Inhibited methyl chloroform
US2923747A (en) * 1958-04-07 1960-02-02 Dow Chemical Co Prevention of corrosion

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2364588A (en) * 1943-04-19 1944-12-05 Shell Dev Stabilization of halobutenes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2371645A (en) * 1943-09-16 1945-03-20 Westvaco Chlorine Products Cor Degreasing process
US2811252A (en) * 1954-03-30 1957-10-29 Dow Chemical Co Methyl chloroform inhibited with dioxane
US2838458A (en) * 1955-09-30 1958-06-10 Dow Chemical Co Inhibited methyl chloroform
GB773187A (en) * 1955-12-08 1957-04-24 Hoechst Ag Method of stabilizing halogenated methanes
US2923747A (en) * 1958-04-07 1960-02-02 Dow Chemical Co Prevention of corrosion

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3281480A (en) * 1961-08-09 1966-10-25 Pittsburgh Plate Glass Co Stabilization of methyl chloroform
DE1246702B (de) * 1962-10-18 1967-08-10 Dynamit Nobel Ag Stabilisierung von 1, 1, 1-Trichloraethan
US3878256A (en) * 1962-10-18 1975-04-15 Dynamit Nobel Ag Stabilization of 1,1,1-trichloroethane with a four component system
US3959397A (en) * 1962-10-18 1976-05-25 Dynamit Nobel Aktiengesellschaft Stabilization of 1,1,1-trichloroethane with a three component system
US4069265A (en) * 1962-10-18 1978-01-17 Dynamit Nobel Aktiengesellschaft Stabilization of 1,1,1-trichloroethane with a four component system
US3536766A (en) * 1968-12-26 1970-10-27 Dow Chemical Co Stabilized methyl chloroform composition
US3681469A (en) * 1970-09-21 1972-08-01 Dow Chemical Co Stabilization of 1,1,1-trichloroethane
US4356038A (en) * 1979-07-25 1982-10-26 Imperial Chemical Industries Limited Stabilization of chlorinated aliphatic hydrocarbons and use of stabilized composition in cleaning articles
FR2486967A1 (fr) * 1980-07-15 1982-01-22 Solvay Compositions stabilisees de 1,1,1-trichloroethane
EP0044111A1 (de) * 1980-07-15 1982-01-20 SOLVAY & Cie (Société Anonyme) Stabilisierte 1,1,1-Trichlorethanzusammensetzungen
US4351973A (en) * 1980-10-06 1982-09-28 The Dow Chemical Company Stabilized methylchloroform
US4394284A (en) * 1981-02-03 1983-07-19 The Dow Chemical Company Stabilized methylchloroform composition
US4327232A (en) * 1981-02-19 1982-04-27 The Dow Chemical Company Cyclopropane ring-containing compounds as inhibitor components in methylchloroform
FR2503697A1 (fr) * 1981-04-13 1982-10-15 Solvay Compositions stabilisees de 1,1,1-trichloroethane
US4795837A (en) * 1981-04-13 1989-01-03 Solvay & Cie (Societe Anonyme) Stabilized compositions of 1,1,1-trichloroethane
US4597890A (en) * 1985-02-15 1986-07-01 The Dow Chemical Company Solvent blend for removing flux residues
US5801136A (en) * 1994-08-19 1998-09-01 Advanced Chemical Design, Inc. Stabilized solvents and method for cleaning metallic, electrical and plastic substrates utilizing environmentally safe solvent materials
US5759985A (en) * 1995-07-21 1998-06-02 Advanced Chemical Design, Inc. Compositions for the stabilization of bromochloromethane

Also Published As

Publication number Publication date
GB916129A (en) 1963-01-23
NL261754A (de)
FR1284254A (fr) 1962-02-09
NL113941C (de)
DE1173306B (de) 1964-07-02

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