US2371645A - Degreasing process - Google Patents
Degreasing process Download PDFInfo
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- US2371645A US2371645A US502648A US50264843A US2371645A US 2371645 A US2371645 A US 2371645A US 502648 A US502648 A US 502648A US 50264843 A US50264843 A US 50264843A US 2371645 A US2371645 A US 2371645A
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- solvent
- decomposition
- ethers
- metal
- chlorinated
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- 238000005238 degreasing Methods 0.000 title description 19
- 238000000034 method Methods 0.000 title description 8
- 230000008569 process Effects 0.000 title description 4
- 239000002904 solvent Substances 0.000 description 64
- 229910052751 metal Inorganic materials 0.000 description 31
- 239000002184 metal Substances 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 238000000354 decomposition reaction Methods 0.000 description 29
- 150000002170 ethers Chemical class 0.000 description 22
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 11
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 10
- 239000004519 grease Substances 0.000 description 9
- 229910045601 alloy Inorganic materials 0.000 description 7
- 239000000956 alloy Substances 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- -1 trichlorethylene Chemical class 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- 239000012808 vapor phase Substances 0.000 description 4
- 230000035508 accumulation Effects 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000002939 deleterious effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 150000002927 oxygen compounds Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013527 degreasing agent Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000000452 restraining effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- VSYMNDBTCKIDLT-UHFFFAOYSA-N [2-(carbamoyloxymethyl)-2-ethylbutyl] carbamate Chemical compound NC(=O)OCC(CC)(CC)COC(N)=O VSYMNDBTCKIDLT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical class NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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
- 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
- C23G5/02877—Ethers
Definitions
- This invention relates to animprovement in degreasing processes and other processes wherein chlorinated solvents are used as solvent media.
- It comprises particularly a method of. degreasing' articles with surfaces of a metal having a decomposing efiect on chlorinated grease solvents, such as aluminum goods, wherein grease is removed from such a metal surface by a chlorinated sol- I vent of a type normally subject to such decomposition, containing a minor amount of certain oxygen-containing organic compounds, advantageously ethers and oxides, which restrain such decomposition.
- the metal article to be degreased is brought into contact with the solvent in the liquid phase. This may be accomplished by immersing the article in a large body of the solvent, or by spraying the solvent on the surface of the article.
- vapor-phase degreasing a body of solvent is maintained at the boiling oint andin communication with a chamber adapted to contain a large body of the solvent vapor.
- the article to be degreased is brought into contact with this body of' vapor, and causes condensation of the solvent on the greasy metal surface.
- the condensed solvent removes grease and oil from the metal surface and drips oii, usually returning to the boiling body of the solvent. With it goes dirt, adhering to the greasy surface. This dirt often includes metal chips.
- it is conventional to provide cooling coils or some equivalent arrangement near the top of the solvent vapor chamber to prevent or minimize the escape of -vapors and loss of solvent from the system; Solvent condensed by such cooling coils is generally substantially uncontaminated by either grease or dirt, and is usually returned to a clean solvent reservoir, which, in many cases,
- solvents of the chlorinated hydrocarbon type including I .both saturated compounds such as carbon tetrachloride, ethylene dichloride. et cetera, and unsaturated compounds such as trichlorethylene, 'perchlorethylene, et cetera, have been widely employed because of their high grease-solvent capacity and their low inflammability. Several of these chlorinated compounds are considered noninflammable. Of the available solvents of this type, trichlorethylene is probably most widely used in degreasing. However, it is seldom used v without the addition of some stabilizer, adaptused for the purpose of inhibiting this decomposition. I
- the present invention is based on our discovery that this metal-induced decomposition of chlorinated solvents, with production of hydrochloric acid and other deleterious decomposition products, is p v nt y t addition to the group, or a substituted ali hatic or aryl group.
- chlorinated hydrocarbon solvents of certain oxy- As noted below R and B may be substituted with gen-containing organic compoun Such as hydroxy, alkoxy. or with other substitutes such ganic oxides and ethers. For instance, that. all? as amino groups.
- hatio ethers or oxides are particular y sui a e 5 For this purpose.
- certain derivatives of complex and 03nd these ethers and oxides such as amino-ethers, Ethyl Cellosolve hydroxy ethers, et cetera, may be employed with advantage in stabilizing chlorinated hydrocarbon HJFOH solvents against metal-induced decomposition.
- the ethers and oxides also have other advan- Butyl 99110501 tages for the present purposes.
- r othey are readily soluble in chlorinated hydrocarmake ⁇ ! bons and are completely compatible with such awe-idol solvents under service conditions. Under ordi- 5 nary conditions they do not react with the chlorinated hydrocarbons to form sludge or other deleterious by-products.
- the ethers and G 1 d oxides do not attack metals since they are neither lycer he methyl ether alkaline nor acidic.
- the aliphatic ethers o CH'OCHI and oxides are themselves substantially inert and HOB stable under most conditions. In other words, HOCH,
- R and B may be the same or may 3K 0 be different radicals. 0 no on 5-0 1] II 1 no on Inner ethers or oaiides or CH ii a Propylene oxide o Ha I Hr-O moxane In the broad practice of our invention, we may 0 employ a wide variety of ethers and oxides as Q noted above. The simple symmetrical and the C CH?
- unsymmetrical ethers the inner ethers or oxides,v m m substituted ethers and oxides particularly those containing hydroxy and-alkoxy, amino groups, Isobutylene oxide and the complex ethers having a number or sub- 0 on; stltuents but all containing the ether linkage are 1126/ all efiective.
- oxygen-containing compgund are gesalnerglltylemplioyedfili minor avanageouy eorero perceno e mphenylene oxide 0 amount of chlorinated solvent by weight.
- the particular percentage incorporated in the chlorinated hydrocarbon solvent may be 66
- These ethers have the generic type formula varied to obtain the stabilization desired. Ordinarily it-is advantageous to add definite molar 0 Q percentages ofthe ether or oxides to the chlorior nated hydrocarbon solvents. However, for puro 10 poses oi the present invention, the more ether or oxide compound present, the more efiective the ⁇ o/ composition in restraining this metal-induced decomposition, This seems tobe true .because where R.
- R may be a divalent aliphatic radi these oxygen compounds unite chemically with cal, either saturated or unsaturated, or an aryl (I the aluminum compounds that appear to cause asvaocs the metal-induced decomposition and thus the more oxygen compound present the more stabilization obtained;
- metal induced decomposition claimed in this application it is generally advantageous to use about 1 mol of oxygen compound per 99 mols of chlorhydrocarbon. However, this amount may be increased with propdrtionately greater stabilization againstinetalinduced decomposition.
- the chlorinated hydrocarbon. solvent in addition to the stabilizers described, may also contain oneof the known stabilizers against normal decomposition, as previously mentioned,
- propyl ether is employed as the oxygen-containing'organic compound.
- This ether is especially suited for the purpose, because in small amounts it tends to vaporize with the trichlorethylene, and therefore tends to remain with the solvent,
- a degreesing solvent was prepared containing 99.0 parts by weight of stabilized trichlorethylene, and 1 part by weight of propyl other. This solvent was used in a vapor-phase degreasing operation of the type previously described for degreasing aluminum surdegreasing solvent, as described hereinabove, is
- This waste metal accumulating in the liquid solvent has large effective surface areas which are highly reactive, especially at the increased boiling temperature of thedirty solvent. It may be that the large metal surface catalyzes the decomposition, or it is possible that aluminum chloride forms at the surface of the metal and that this compound is the active decomposing agent.
- chlorinated solvents such as trichlorethylene, containing minor amounts of ethers or oxides,*are particularly adapted'for use in degreasing aluminum and its alloys.
- Such solvents are also useful in degreasing other metals, including zinc and magnesium and'their alloys as well as iron, steel, copper, et cetera.,
- the improve-t ment which comprises maintaining, in admixture with such chlorinated solvents, a minor amount of an organic inner ether to inhibit such metal-"1 induced decomposition thereof.
- oi metals of the class consisting of aluminum and its alloys having a decomposing effect on chlorinated hydrocarbon grease solvents which comprises establishing a body of grease solvent in communication with a space adapted to receive vapors therefrom, said solvent comprising a maior proportion of chlorinated hydrocarbon solvent, i normally subjectto decomposition in the presence of such metal surfaces, and a minor proportion of an organic ether having the property of restraining decomposition of such solvents in the presence of saidmetal surfaces, boiling said body of grease solvent and thereby maintaining a body of vapors thereof in said vapor space,. contacting the metal surface to be decreased with said body of vapors and returning the solvent condensed ADAM G.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Chemistry (AREA)
- Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
- Detergent Compositions (AREA)
Description
Patented Mar. 20, 1945 DEGBEASING PROCESS Adam G. 'Aitehison, Westfleld, and Wilbur H.
Peterlng, Metuchen, N. 1., assignors to Westvaco Chlorine Products Corporation, New York, N. Y.. a corporation of Delaware No Drawing. Application September 16, 1943,
Serial No. 502,648
11 Glalms.
This invention relates to animprovement in degreasing processes and other processes wherein chlorinated solvents are used as solvent media.
It comprises particularly a method of. degreasing' articles with surfaces of a metal having a decomposing efiect on chlorinated grease solvents, such as aluminum goods, wherein grease is removed from such a metal surface by a chlorinated sol- I vent of a type normally subject to such decomposition, containing a minor amount of certain oxygen-containing organic compounds, advantageously ethers and oxides, which restrain such decomposition.
This application is a continuation-in-part of our copending application, Serial Number 386,544, filed April 2, 1941.
. Theremoval of grease iilms from metal surfaces by the application of grease solvents has been widely practiced during recent years. Numerous solvents have been employed, and numerous variations of the degreasing procedure have been suggested. In one method of operating, the metal article to be degreased is brought into contact with the solvent in the liquid phase. This may be accomplished by immersing the article in a large body of the solvent, or by spraying the solvent on the surface of the article. In another common method of degreasing, known generally as vapor-phase degreasing, a body of solvent is maintained at the boiling oint andin communication with a chamber adapted to contain a large body of the solvent vapor. The article to be degreased is brought into contact with this body of' vapor, and causes condensation of the solvent on the greasy metal surface. The condensed solvent removes grease and oil from the metal surface and drips oii, usually returning to the boiling body of the solvent. With it goes dirt, adhering to the greasy surface. This dirt often includes metal chips. In vapor-phase degreasers of this type, it is conventional to provide cooling coils or some equivalent arrangement near the top of the solvent vapor chamber to prevent or minimize the escape of -vapors and loss of solvent from the system; Solvent condensed by such cooling coils is generally substantially uncontaminated by either grease or dirt, and is usually returned to a clean solvent reservoir, which, in many cases,
is arranged to overflow into the solvent boiling compartment. In some cases, even when employing vaporphase degreasing, the article to be degreased is preliminarily dipped in a body of liquid solvent. When hot solvent is employed for this purpose, there is sometimesa subsequent dip in in degreasing operations. Among these, solvents of the chlorinated hydrocarbon type, including I .both saturated compounds such as carbon tetrachloride, ethylene dichloride. et cetera, and unsaturated compounds such as trichlorethylene, 'perchlorethylene, et cetera, have been widely employed because of their high grease-solvent capacity and their low inflammability. Several of these chlorinated compounds are considered noninflammable. Of the available solvents of this type, trichlorethylene is probably most widely used in degreasing. However, it is seldom used v without the addition of some stabilizer, adaptused for the purpose of inhibiting this decomposition. I
These previously known stabilizers are effective when present in minute amounts in preventing decomposition of trichlorethylene, for example during storage and during the usual degreasin operations applied to ferrous metals and several other metals. However, when the metal to be degreased is aluminum or an aluminum alloy, it
has been found that a. different type of decomposition of the solvent is encountered, and that this type of decomposition may occur even in the presence of stabilizers which are effective in all other cases. This form of decomposition of chlorinated solvents in contact with metallic aluminum or its alloys is evidenced by a rapid rise in acidity (largely hydrochloric acid), by pronounced discoloration of the solvent, and,jin the advanced stages of decomposition, by the formation of a tarry or gummy mass in the solvent.
Efforts have been made heretofore to eliminate or this type of decomposition by various special practices. In some instances, these practices have been partially successful, in that they have reduced formation of the above-men tioned tarry and gummy masses from the solvent, for example. However, when such results have been obtained, they have been accompanied by-undeslrable results of other types, such as increased acid development. It does not appear that prior to this invention there has been any satisfactory solution to the problem of decomposition encountered with the chlorinated solvents which are susceptible thereto, such as trichlorethylene, perchlorethylene, et cetera, when they ar kept in contact with aluminum ,or its alloys having a decomposing influence at high temperatures.
The present invention is based on our discovery that this metal-induced decomposition of chlorinated solvents, with production of hydrochloric acid and other deleterious decomposition products, is p v nt y t addition to the group, or a substituted ali hatic or aryl group. chlorinated hydrocarbon solvents of certain oxy- As noted below R and B may be substituted with gen-containing organic compoun Such as hydroxy, alkoxy. or with other substitutes such ganic oxides and ethers. For instance, that. all? as amino groups.
hatio ethers or oxides are particular y sui a e 5 For this purpose. Likewise, certain derivatives of complex and 03nd these ethers and oxides, such as amino-ethers, Ethyl Cellosolve hydroxy ethers, et cetera, may be employed with advantage in stabilizing chlorinated hydrocarbon HJFOH solvents against metal-induced decomposition. l a
The ethers and oxides also have other advan- Butyl 99110501 tages for the present purposes. First, as a class, r othey are readily soluble in chlorinated hydrocarmake}! bons and are completely compatible with such awe-idol solvents under service conditions. Under ordi- 5 nary conditions they do not react with the chlorinated hydrocarbons to form sludge or other deleterious by-products. Likewise, the ethers and G 1 d oxides do not attack metals since they are neither lycer he methyl ether alkaline nor acidic. In fact, the aliphatic ethers o CH'OCHI and oxides are themselves substantially inert and HOB stable under most conditions. In other words, HOCH,
the aliphatic ethers and oxides effectively stabmze chlorinated hydrocarbons against metal Glycerineamonomethyl ether induced decomposition without any deleterious x mon action, both during storage and under. service conditions. mocm We have used both straight chain and branched-chain ethers and oxides and obtained y r yl a cohol effective stabilization against metal-induced de- 30 '0 composition of the chlorinated solvents; The following ethers are illustrative of the types or ethers 1 that are eflective in the practice of our invention: PC3103 simple ethers Glycerine formal 36 0 Diethyl ether DialLvl ether onion Di-n-propyl ether Di-n-butyl ether l Di-isopropyl ether Diphenyl ether Hon on, or CH Ethers may be-used which have the general CH 0 type formula ROR where R and R mag be an aliphatic radical, either saturated or unsa ated, or an aryl group, or a substituted aliphatic or Glycenne Mural aryl radical. R and B may be the same or may 3K 0 be different radicals. 0 no on 5-0 1] II 1 no on Inner ethers or oaiides or CH ii a Propylene oxide o Ha I Hr-O moxane In the broad practice of our invention, we may 0 employ a wide variety of ethers and oxides as Q noted above. The simple symmetrical and the C CH? unsymmetrical ethers, the inner ethers or oxides,v m m substituted ethers and oxides particularly those containing hydroxy and-alkoxy, amino groups, Isobutylene oxide and the complex ethers having a number or sub- 0 on; stltuents but all containing the ether linkage are 1126/ all efiective. These oxygen-containing compgund: are gesalnerglltylemplioyedfili minor avanageouy eorero perceno e mphenylene oxide 0 amount of chlorinated solvent by weight. However, as the efiectiveness or these stabilizers varies to someextent with the type of compopnd employed, the particular percentage incorporated in the chlorinated hydrocarbon solvent may be 66 These ethers have the generic type formula varied to obtain the stabilization desired. Ordinarily it-is advantageous to add definite molar 0 Q percentages ofthe ether or oxides to the chlorior nated hydrocarbon solvents. However, for puro 10 poses oi the present invention, the more ether or oxide compound present, the more efiective the \o/ composition in restraining this metal-induced decomposition, This seems tobe true .because where R. and R may be a divalent aliphatic radi these oxygen compounds unite chemically with cal, either saturated or unsaturated, or an aryl (I the aluminum compounds that appear to cause asvaocs the metal-induced decomposition and thus the more oxygen compound present the more stabilization obtained; For "metal induced" decomposition claimed in this application it is generally advantageous to use about 1 mol of oxygen compound per 99 mols of chlorhydrocarbon. However, this amount may be increased with propdrtionately greater stabilization againstinetalinduced decomposition.
In the practice of our invention, many and various embodimentsthereof may be employed.
For instance, the chlorinated hydrocarbon. solvent, in addition to the stabilizers described, may also contain oneof the known stabilizers against normal decomposition, as previously mentioned,
such as aralkyl ethers of hydroquinone, described I in Pitman Patent 2,319,261.
'In one useful embodiment of the invention, propyl ether is employed as the oxygen-containing'organic compound. This ether is especially suited for the purpose, because in small amounts it tends to vaporize with the trichlorethylene, and therefore tends to remain with the solvent,
both as liquid and as vapor, during degreasing operations and purification of the solvent in solvent-extraction, dry-cleaning, and similar operations. For example, on distilling the solvent out of the boiling compartment, little, if any of this volatile ether is lost. The etherevaporates and rec'ondenses with the solvent. The propyl ether is highly effective in preventing the metal-induced type of decomposition of trichlorethylene and similar chlorinated solvents, and its moderate cost is another favorable factor. In general,
when working with any specific chlorinated solvent,- it is desirable to employ an ether or oxide forming a mixture which may be distilled with out loss of stabilizer.
One specific advantage resulting from the addition of suitable ethers and oxides to chlorinated embodiment of the present invention, a degreesing solvent was prepared containing 99.0 parts by weight of stabilized trichlorethylene, and 1 part by weight of propyl other. This solvent was used in a vapor-phase degreasing operation of the type previously described for degreasing aluminum surdegreasing solvent, as described hereinabove, is
that thepresence of a minor amount of the ether .or'oxide, with the resulting decrease in metalinduced decomposition, permits operation of the degreasing equipment for a longer period without the necessity of shutting down to clean out accumulations in the boiling compartment. As previously noted, the reactions involved in this metal-induced decomposition are somewhat ob-' scure. One explanation of these reactions is that th accumulation of non-volatile oils removed from the work during the degreasing operation, may raise the boiling point (or range) of the liquid in the boiling compartment of the degreaser to such an extent that reaction sets in between the chlorinated solvent and the finely divided aluminum or. other metal which has also been washed off the. work. This waste metal accumulating in the liquid solvent has large effective surface areas which are highly reactive, especially at the increased boiling temperature of thedirty solvent. It may be that the large metal surface catalyzes the decomposition, or it is possible that aluminum chloride forms at the surface of the metal and that this compound is the active decomposing agent.
Whatever the mechanism of the metal-induced decomposition, it has been necessary in the past to remove the accumulation of oily material and finely divided metal and metal compounds from the, boiling compartment at frequent intervals. This involves additional labor, loss of production during the cleaning period, and loss of solvent. These difiiculties are largely eliminated by operface's. No objectionable decomposition was en-' countered, ,even after continuing the operations without cleaning out the boiling compartment of the degreaser for considerably longer than had beenpossible before the use of the ether in accordance with this invention.
In the operation justdescribed, it was found that the ether vaporized with the trichlorethylene, was condensed, and returned to the liquid compartments with the trichlorethylene.
These chlorinated solvents, such as trichlorethylene, containing minor amounts of ethers or oxides,*are particularly adapted'for use in degreasing aluminum and its alloys. Such solvents are also useful in degreasing other metals, including zinc and magnesium and'their alloys as well as iron, steel, copper, et cetera.,
While we have particularly described our invention hereinabove with respect to certain ethers and oxides, it will be obvious to the skilled in the art that the invention is not limited to the specific examples shown, but may be practiced and embodied within the scope of the claims hereinafter made.
What weclaim is:
1. As an improvement in degreasing surfaces .of aluminum and its alloys with chlorinated hydrocarbon solvents normally subject to deterioration in the presence of aluminum, the improvement which comprises maintaining, inadmixture s with such chlorinated solvents, a minor amount of an organic ether to inhibit such metal-induced decomposition thereof.
2'. As an improvement in degreasing surfaces of aluminum and its alloys with chlorinated hydrocarbon solvents normally subject to deterioration in the presence of aluminum,.the improve-t ment which comprises maintaining, in admixture with such chlorinated solvents, a minor amount of an organic inner ether to inhibit such metal-"1 induced decomposition thereof.
3. As an improvement in degreasing surfaces is propyl ether.
oi metals of the class consisting of aluminum and its alloys having a decomposing effect on chlorinated hydrocarbon grease solvents, which comprises establishing a body of grease solvent in communication with a space adapted to receive vapors therefrom, said solvent comprising a maior proportion of chlorinated hydrocarbon solvent, i normally subjectto decomposition in the presence of such metal surfaces, and a minor proportion of an organic ether having the property of restraining decomposition of such solvents in the presence of saidmetal surfaces, boiling said body of grease solvent and thereby maintaining a body of vapors thereof in said vapor space,. contacting the metal surface to be decreased with said body of vapors and returning the solvent condensed ADAM G. AITCHISON. wmaon H. PE'IERING.
Priority Applications (1)
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US502648A US2371645A (en) | 1943-09-16 | 1943-09-16 | Degreasing process |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US502648A US2371645A (en) | 1943-09-16 | 1943-09-16 | Degreasing process |
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US2371645A true US2371645A (en) | 1945-03-20 |
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US502648A Expired - Lifetime US2371645A (en) | 1943-09-16 | 1943-09-16 | Degreasing process |
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Cited By (59)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2423343A (en) * | 1945-04-27 | 1947-07-01 | Westvaco Chlorine Products Cor | Process of degreasing aluminum and magnesium surfaces |
US2517895A (en) * | 1946-05-13 | 1950-08-08 | Du Pont | Stabilized chlorohydrocarbon cleaning composition |
US2517893A (en) * | 1946-05-13 | 1950-08-08 | Du Pont | Stabilized chlorohydrocarbon cleaning composition |
US2517894A (en) * | 1946-05-13 | 1950-08-08 | Du Pont | Metal degreasing composition |
US2643961A (en) * | 1948-05-22 | 1953-06-30 | Anaconda Wire & Cable Co | Cleaning cupreous articles |
US2740734A (en) * | 1949-10-11 | 1956-04-03 | Detrex Corp | Methods for cleaning food containers and the like |
US2742509A (en) * | 1954-07-23 | 1956-04-17 | Du Pont | Stabilization of chlorinated hydrocarbons |
US2795623A (en) * | 1954-11-15 | 1957-06-11 | Du Pont | Stabilization of chlorinated hydrocarbons |
US2802885A (en) * | 1954-08-16 | 1957-08-13 | Air Reduction | Stabilization of chlorinated hydrocarbons with 3, 3-dimethoxy-2-methyl-butan-2-ol |
US2811252A (en) * | 1954-03-30 | 1957-10-29 | Dow Chemical Co | Methyl chloroform inhibited with dioxane |
US2818446A (en) * | 1956-09-18 | 1957-12-31 | Du Pont | Stabilization of chlorinated hydrocarbons |
US2838458A (en) * | 1955-09-30 | 1958-06-10 | Dow Chemical Co | Inhibited methyl chloroform |
US2857922A (en) * | 1951-10-09 | 1958-10-28 | Shell Dev | Apparatus for cleaning tube bundles |
US2868851A (en) * | 1954-07-26 | 1959-01-13 | Diamond Alkali Co | Stabilization of chlorinated hydrocarbons with acetylenic ethers |
US2870094A (en) * | 1955-09-28 | 1959-01-20 | Eastman Kodak Co | Photographic film cleaning solutions |
US2904600A (en) * | 1956-04-04 | 1959-09-15 | Du Pont | Stabilization of chlorinated hydrocarbons |
US2923747A (en) * | 1958-04-07 | 1960-02-02 | Dow Chemical Co | Prevention of corrosion |
US2970113A (en) * | 1957-05-31 | 1961-01-31 | Dow Chemical Co | Stabilization of 1, 1, 1-trichloroethane |
US2981759A (en) * | 1956-02-08 | 1961-04-25 | Air Reduction | Stabilization of chlorinated hydrocarbons with a synergistic combination of a tertiary acetylenic alcohol, dioxane, and a volatile basic organic nitrogen-containing organic compound |
US2998461A (en) * | 1959-04-15 | 1961-08-29 | Hooker Chemical Corp | Stabilization of trichloroethylene |
US3008999A (en) * | 1959-10-08 | 1961-11-14 | Argus Chem | Stabilization of methylchloroform |
US3025331A (en) * | 1958-10-31 | 1962-03-13 | Pittsburgh Plate Glass Co | Stabilization of liquid halogenated aliphatic hydrocarbons |
US3043888A (en) * | 1959-02-09 | 1962-07-10 | Pittsburgh Plate Glass Co | Stabilization |
US3049571A (en) * | 1960-03-18 | 1962-08-14 | Dow Chemical Co | Stabilized degreasing solvent |
US3070634A (en) * | 1960-03-01 | 1962-12-25 | Pittsburgh Plate Glass Co | Stabilization of methylchloroform |
US3074890A (en) * | 1958-10-27 | 1963-01-22 | Ethyl Corp | Stable solvent composition |
US3099694A (en) * | 1960-05-27 | 1963-07-30 | Ethyl Corp | Stable methylchloroform compositions |
US3113156A (en) * | 1960-05-27 | 1963-12-03 | Ethyl Corp | Chlorinated solvents stabilized with mixture of a dioxolane compound and a nitroaliphatic compound |
US3113154A (en) * | 1960-05-27 | 1963-12-03 | Ethyl Corp | Stable methylchloroform compositions |
US3113155A (en) * | 1960-05-27 | 1963-12-03 | Ethyl Corp | Chlorinated solvents stabilized with mixtures of a dioxolane compound, a nitro-aliphatic compound, and an aliphatic carboxylic acid ester |
US3120567A (en) * | 1960-07-15 | 1964-02-04 | Pittsburgh Plate Glass Co | Stabilization of perchloroethylene with a mixture of an epoxide and an alkoxynitrile |
US3128315A (en) * | 1961-03-13 | 1964-04-07 | Pittsburgh Plate Glass Co | Methylchloroform stabilized with dialkylethers of alkylene glycols |
US3133885A (en) * | 1954-07-23 | 1964-05-19 | Detrex Chem Ind | Method of inhibiting metal corrosion by amine-stabilized unsaturated chlorinated hydrocarbons |
US3278397A (en) * | 1963-07-18 | 1966-10-11 | Monsanto Co | Removal of hci from vinyl chloride by distillation in the presence of styrene oxide and a pyridine |
US3278615A (en) * | 1963-04-08 | 1966-10-11 | Dow Chemical Co | Stabilization of haloalkanes with fluoroethers of the type |
US3285857A (en) * | 1961-10-30 | 1966-11-15 | Ici Ltd | Stabilized methyl chloroform composition |
US3360575A (en) * | 1963-11-20 | 1967-12-26 | Dow Chemical Co | Stabilized solvent system |
US3397246A (en) * | 1966-04-26 | 1968-08-13 | Solvay | Stabilized chlorinated hydrocarbons |
US3475503A (en) * | 1967-12-01 | 1969-10-28 | Dow Chemical Co | Stabilization of 1,1,1-trichloroethane |
US3496241A (en) * | 1966-07-21 | 1970-02-17 | Fmc Corp | Stabilization of chlorinated hydrocarbons |
US3499047A (en) * | 1958-02-03 | 1970-03-03 | Ppg Industries Inc | Stabilized compositions |
US3505415A (en) * | 1963-05-18 | 1970-04-07 | Dynamit Nobel Ag | Process for stabilizing 1,1,1-trichlorethane |
US3519694A (en) * | 1965-10-22 | 1970-07-07 | Dow Chemical Co | Stabilization of methyl chloroform |
US3532761A (en) * | 1969-05-07 | 1970-10-06 | Ppg Industries Inc | Stabilization of methyl chloroform |
US3535392A (en) * | 1958-02-03 | 1970-10-20 | Ppg Industries Inc | Stabilized methylchloroform |
JPS4987606A (en) * | 1972-12-15 | 1974-08-22 | ||
US3839087A (en) * | 1972-11-17 | 1974-10-01 | Diamond Shamrock Corp | Perchloroethylene vapor degreasing process |
US3876712A (en) * | 1972-08-10 | 1975-04-08 | Ethyl Corp | Stabilized halogenated hydrocarbons |
US4687523A (en) * | 1985-08-16 | 1987-08-18 | Mobil Oil Corporation | Method for cleaning a core sample from a subterranean formation of solid contaminant particles |
EP0609004A1 (en) * | 1993-01-25 | 1994-08-03 | Dipsol Chemical Co., Ltd | Deterging solvent composition and a method for washing an article with the same |
US5665170A (en) * | 1995-11-01 | 1997-09-09 | Albemarle Corporation | Solvent system |
US5665173A (en) * | 1996-02-29 | 1997-09-09 | Albemarle Corporation | Movie film cleaning process |
US5669985A (en) * | 1996-02-29 | 1997-09-23 | Albemarle Corporation | Movie film cleaning process |
US5679632A (en) * | 1996-02-29 | 1997-10-21 | Albemarle Corp | Movie film cleaning solvent comprising n-propylbromide |
US5690862A (en) * | 1995-11-01 | 1997-11-25 | Albemarle Corporation | No flash point solvent system containing normal propyl bromide |
US5707954A (en) * | 1996-03-01 | 1998-01-13 | Albemarle Corporation | Stabilized brominated alkane solvent |
US5792277A (en) * | 1997-07-23 | 1998-08-11 | Albemarle Corporation | N-propyl bromide based cleaning solvent and ionic residue removal process |
US5824162A (en) * | 1995-12-29 | 1998-10-20 | Lawrence Industries, Inc. | Molecular level cleaning of contaminates from parts utilizing an environmentally safe solvent |
JP2007509111A (en) * | 2003-10-24 | 2007-04-12 | アルケマ フランス | Stabilization of trans-1,2-dichloroethylene |
-
1943
- 1943-09-16 US US502648A patent/US2371645A/en not_active Expired - Lifetime
Cited By (65)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2423343A (en) * | 1945-04-27 | 1947-07-01 | Westvaco Chlorine Products Cor | Process of degreasing aluminum and magnesium surfaces |
US2517895A (en) * | 1946-05-13 | 1950-08-08 | Du Pont | Stabilized chlorohydrocarbon cleaning composition |
US2517893A (en) * | 1946-05-13 | 1950-08-08 | Du Pont | Stabilized chlorohydrocarbon cleaning composition |
US2517894A (en) * | 1946-05-13 | 1950-08-08 | Du Pont | Metal degreasing composition |
US2643961A (en) * | 1948-05-22 | 1953-06-30 | Anaconda Wire & Cable Co | Cleaning cupreous articles |
US2740734A (en) * | 1949-10-11 | 1956-04-03 | Detrex Corp | Methods for cleaning food containers and the like |
US2857922A (en) * | 1951-10-09 | 1958-10-28 | Shell Dev | Apparatus for cleaning tube bundles |
US2811252A (en) * | 1954-03-30 | 1957-10-29 | Dow Chemical Co | Methyl chloroform inhibited with dioxane |
US3133885A (en) * | 1954-07-23 | 1964-05-19 | Detrex Chem Ind | Method of inhibiting metal corrosion by amine-stabilized unsaturated chlorinated hydrocarbons |
US2742509A (en) * | 1954-07-23 | 1956-04-17 | Du Pont | Stabilization of chlorinated hydrocarbons |
US2868851A (en) * | 1954-07-26 | 1959-01-13 | Diamond Alkali Co | Stabilization of chlorinated hydrocarbons with acetylenic ethers |
US2802885A (en) * | 1954-08-16 | 1957-08-13 | Air Reduction | Stabilization of chlorinated hydrocarbons with 3, 3-dimethoxy-2-methyl-butan-2-ol |
US2795623A (en) * | 1954-11-15 | 1957-06-11 | Du Pont | Stabilization of chlorinated hydrocarbons |
US2870094A (en) * | 1955-09-28 | 1959-01-20 | Eastman Kodak Co | Photographic film cleaning solutions |
US2838458A (en) * | 1955-09-30 | 1958-06-10 | Dow Chemical Co | Inhibited methyl chloroform |
US2981759A (en) * | 1956-02-08 | 1961-04-25 | Air Reduction | Stabilization of chlorinated hydrocarbons with a synergistic combination of a tertiary acetylenic alcohol, dioxane, and a volatile basic organic nitrogen-containing organic compound |
US2904600A (en) * | 1956-04-04 | 1959-09-15 | Du Pont | Stabilization of chlorinated hydrocarbons |
US2818446A (en) * | 1956-09-18 | 1957-12-31 | Du Pont | Stabilization of chlorinated hydrocarbons |
US2970113A (en) * | 1957-05-31 | 1961-01-31 | Dow Chemical Co | Stabilization of 1, 1, 1-trichloroethane |
US3499047A (en) * | 1958-02-03 | 1970-03-03 | Ppg Industries Inc | Stabilized compositions |
US3535392A (en) * | 1958-02-03 | 1970-10-20 | Ppg Industries Inc | Stabilized methylchloroform |
US2923747A (en) * | 1958-04-07 | 1960-02-02 | Dow Chemical Co | Prevention of corrosion |
US3074890A (en) * | 1958-10-27 | 1963-01-22 | Ethyl Corp | Stable solvent composition |
US3025331A (en) * | 1958-10-31 | 1962-03-13 | Pittsburgh Plate Glass Co | Stabilization of liquid halogenated aliphatic hydrocarbons |
US3043888A (en) * | 1959-02-09 | 1962-07-10 | Pittsburgh Plate Glass Co | Stabilization |
US2998461A (en) * | 1959-04-15 | 1961-08-29 | Hooker Chemical Corp | Stabilization of trichloroethylene |
US3008999A (en) * | 1959-10-08 | 1961-11-14 | Argus Chem | Stabilization of methylchloroform |
US3070634A (en) * | 1960-03-01 | 1962-12-25 | Pittsburgh Plate Glass Co | Stabilization of methylchloroform |
US3049571A (en) * | 1960-03-18 | 1962-08-14 | Dow Chemical Co | Stabilized degreasing solvent |
US3099694A (en) * | 1960-05-27 | 1963-07-30 | Ethyl Corp | Stable methylchloroform compositions |
US3113156A (en) * | 1960-05-27 | 1963-12-03 | Ethyl Corp | Chlorinated solvents stabilized with mixture of a dioxolane compound and a nitroaliphatic compound |
US3113154A (en) * | 1960-05-27 | 1963-12-03 | Ethyl Corp | Stable methylchloroform compositions |
US3113155A (en) * | 1960-05-27 | 1963-12-03 | Ethyl Corp | Chlorinated solvents stabilized with mixtures of a dioxolane compound, a nitro-aliphatic compound, and an aliphatic carboxylic acid ester |
US3120567A (en) * | 1960-07-15 | 1964-02-04 | Pittsburgh Plate Glass Co | Stabilization of perchloroethylene with a mixture of an epoxide and an alkoxynitrile |
US3128315A (en) * | 1961-03-13 | 1964-04-07 | Pittsburgh Plate Glass Co | Methylchloroform stabilized with dialkylethers of alkylene glycols |
US3285857A (en) * | 1961-10-30 | 1966-11-15 | Ici Ltd | Stabilized methyl chloroform composition |
US3278615A (en) * | 1963-04-08 | 1966-10-11 | Dow Chemical Co | Stabilization of haloalkanes with fluoroethers of the type |
US3505415A (en) * | 1963-05-18 | 1970-04-07 | Dynamit Nobel Ag | Process for stabilizing 1,1,1-trichlorethane |
US3303107A (en) * | 1963-07-18 | 1967-02-07 | Monsanto Co | Purification of vinyl chloride containing hci as an impurity by distillation in the presence of an epoxy compound |
US3278397A (en) * | 1963-07-18 | 1966-10-11 | Monsanto Co | Removal of hci from vinyl chloride by distillation in the presence of styrene oxide and a pyridine |
US3360575A (en) * | 1963-11-20 | 1967-12-26 | Dow Chemical Co | Stabilized solvent system |
US3519694A (en) * | 1965-10-22 | 1970-07-07 | Dow Chemical Co | Stabilization of methyl chloroform |
US3397246A (en) * | 1966-04-26 | 1968-08-13 | Solvay | Stabilized chlorinated hydrocarbons |
US3496241A (en) * | 1966-07-21 | 1970-02-17 | Fmc Corp | Stabilization of chlorinated hydrocarbons |
US3475503A (en) * | 1967-12-01 | 1969-10-28 | Dow Chemical Co | Stabilization of 1,1,1-trichloroethane |
US3532761A (en) * | 1969-05-07 | 1970-10-06 | Ppg Industries Inc | Stabilization of methyl chloroform |
US3876712A (en) * | 1972-08-10 | 1975-04-08 | Ethyl Corp | Stabilized halogenated hydrocarbons |
US3839087A (en) * | 1972-11-17 | 1974-10-01 | Diamond Shamrock Corp | Perchloroethylene vapor degreasing process |
JPS4987606A (en) * | 1972-12-15 | 1974-08-22 | ||
US4687523A (en) * | 1985-08-16 | 1987-08-18 | Mobil Oil Corporation | Method for cleaning a core sample from a subterranean formation of solid contaminant particles |
US5492645A (en) * | 1993-01-25 | 1996-02-20 | Dipsol Chemicals Co., Ltd. | Deterging solvent composition with n-or iso-propyl bromide, a nitroalkane, and an ethylene glycol monoalkyl ether |
US5665172A (en) * | 1993-01-25 | 1997-09-09 | Dipsol Chemicals Co., Ltd. | Method for washing an article with composition having a brominated hydrocarbon and stabilizer |
EP0609004A1 (en) * | 1993-01-25 | 1994-08-03 | Dipsol Chemical Co., Ltd | Deterging solvent composition and a method for washing an article with the same |
US5665170A (en) * | 1995-11-01 | 1997-09-09 | Albemarle Corporation | Solvent system |
US5690862A (en) * | 1995-11-01 | 1997-11-25 | Albemarle Corporation | No flash point solvent system containing normal propyl bromide |
US5824162A (en) * | 1995-12-29 | 1998-10-20 | Lawrence Industries, Inc. | Molecular level cleaning of contaminates from parts utilizing an environmentally safe solvent |
US6176942B1 (en) | 1995-12-29 | 2001-01-23 | Lawrence Industries, Inc | Solvent mixture for use in a vapor degreaser and method of cleaning an article in a vapor degreaser utilizing said solvent |
US5938859A (en) * | 1995-12-29 | 1999-08-17 | Lawrence Industries, Inc. | Molecular level cleaning of contaminants from parts utilizing an environmentally safe solvent |
US5679632A (en) * | 1996-02-29 | 1997-10-21 | Albemarle Corp | Movie film cleaning solvent comprising n-propylbromide |
US5669985A (en) * | 1996-02-29 | 1997-09-23 | Albemarle Corporation | Movie film cleaning process |
US5665173A (en) * | 1996-02-29 | 1997-09-09 | Albemarle Corporation | Movie film cleaning process |
US5707954A (en) * | 1996-03-01 | 1998-01-13 | Albemarle Corporation | Stabilized brominated alkane solvent |
US5792277A (en) * | 1997-07-23 | 1998-08-11 | Albemarle Corporation | N-propyl bromide based cleaning solvent and ionic residue removal process |
JP2007509111A (en) * | 2003-10-24 | 2007-04-12 | アルケマ フランス | Stabilization of trans-1,2-dichloroethylene |
JP4764824B2 (en) * | 2003-10-24 | 2011-09-07 | アルケマ フランス | Stabilization of trans-1,2-dichloroethylene |
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