US3000977A - Method of stabilizing trichloroethyl- - Google Patents
Method of stabilizing trichloroethyl- Download PDFInfo
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- US3000977A US3000977A US3000977DA US3000977A US 3000977 A US3000977 A US 3000977A US 3000977D A US3000977D A US 3000977DA US 3000977 A US3000977 A US 3000977A
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- Prior art keywords
- trichloroethylene
- dimethylhydrazine
- isobutyl alcohol
- stabilizing
- phenol
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- 230000000087 stabilizing effect Effects 0.000 title description 17
- 238000000034 method Methods 0.000 title description 11
- -1 trichloroethyl- Chemical group 0.000 title 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 50
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 28
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 27
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 27
- 229940035429 isobutyl alcohol Drugs 0.000 claims description 25
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 13
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 12
- 238000000354 decomposition reaction Methods 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 150000002739 metals Chemical class 0.000 claims description 8
- 238000005238 degreasing Methods 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 6
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical class COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 claims 1
- 230000002195 synergetic effect Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- YBHFXIXJNDNBQG-UHFFFAOYSA-N 3-ethyl-4-methoxyphenol Chemical compound CCC1=CC(O)=CC=C1OC YBHFXIXJNDNBQG-UHFFFAOYSA-N 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 241000543381 Cliftonia monophylla Species 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- PFLUPZGCTVGDLV-UHFFFAOYSA-N acetone azine Chemical compound CC(C)=NN=C(C)C PFLUPZGCTVGDLV-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960003505 mequinol Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 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
- C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
- C23G1/02—Cleaning or pickling metallic material with solutions or molten salts with acid solutions
- C23G1/04—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors
- C23G1/06—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
- A62D3/36—Detoxification by using acid or alkaline reagents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/32—Organic compounds containing nitrogen
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/20—Organic substances
- A62D2101/22—Organic substances containing halogen
Definitions
- the present invention relates to a method of stabilizing trichloroethylene and to a stabilizing composition therefor.
- trichloroethylene is utilized industrially in various technical processes, particularly as a solvent for degreasing metals. Since trichloroethylene is an unstable chemical compound, the solvent is easily decomposed during such processes. The phenomena of decomposition of trichloroethylene are enhanced by the presence of air, light, moisture andheat, particularly.
- the objects of ourinvention are attained with the aid of our technically improved method of stabilizing tri ice ideneazine, and dimethylketazine, and is admixed to trichloroethylene in amounts of from 0.01% to 0.02% b weight approximately.
- the epoxide may be, for instance, one of the group comprising butylene oxide, propylene oxide, amylene oxide, or chloropropylene oxide and is added to trichloroethylene in amounts of'fromn0.2% to 0.3% by weight approximately.
- the alcohol may be one of the groupcomprising isobutyl alcohol, butyl alcohol, propyl alcohol, isopropyl alcohol, amyl alcohol, isoamyl alcohol, ethyl alcohol, and may be added to trichloroethylene in amounts of from 0.05% to 0.1% by weight approximately.
- the phenolic compound may be chosen from the grou comprising phenol, thymol, ortho-nitrophenol, eugenol, is0propyl-p-hydroxyanisol, ethyl-p-hydroxyanisol, and should be added to trichloroethylene preferably in quan tities of from 0.005 to 0.01% by weight approximately.
- the quantities of the components of the synergetic mixture may be chosen larger or smaller than the amounts given above depending upon the stabilizing effects to be attained and according to the other adjuvants which may be present in the solvent.
- the synergetic mixture according to the invention may contain one or several substances for each'type of the components mentioned further above, and. chosen-from the list of substances mentioned for each type. 1
- the group of the phenols may be represented the synergetic mixture not only by phenol itself, but may also consist of a mixture of phenol and th'ymol; as reprlesentative of the class of epoxides, a mixture of propyl ene oxide and butylene oxide may be added, and the' same applim to the other two groups, to be present as components in the synergetic mixture.
- Our invention is based on thediscovery that it is possible to produceasynergetib action of stabilizing trichloroethylene when a quaternary combination is added to trichloroeithylene, the mixture containing a hydrazine derivative, 'an epoxide, an alcohol and-a phenolic comw h"
- the hydrazine, derivative may .be one of the group werei NNiiPifllYlllYdWH? zae na i fl
- This stability test consists essentially in causing 200 m1. of trichloroethylene to. boil for 48 hours in a Pyr'ex flask of 500 ml.
- a glas'sltiibQe having: a diameter of 3 mmL at a speed of 10 61-2; bubbles per minute; a b x 2 x94 inch SAE, steel strip is suspended inthe vapor "phase whilefa A'x x inch SAE steel strip is introduced "intofthefflask .iiijthe liquid ase a 1'50 ,w.'- frosted light bulb is used.- but s he a agre nether At the end of the test, the acidity of the trichloroethylene isdetermined.
- the percentages of the various adjuvants are given by weight.
- the pH values are determined in the aqueous extracts of trichloroethylene after the completion of the stability test by using in each case the same ratio of waterztrichloroethylene of 1: 1. All of the tests were repeated two or three times and the results averaged.
- TEST SERIES I Examples 115 This test series was conducted to demonstrate the stabilizing action of the synergetic mixture of butylene oxide and isobutyl alcohol+phenol-l-N,N-dimethylhydrazine. Table I shows the results of the tests on the basis of Examples 1 through 15: Examples 1 to 4 were carried out with individual stabilizing compounds; Examples 5 to with binary mixture, Examples 11 to 14 with ternary mixtures and Example 15 finally with the quaternary mixture according to our present invention.
- N,N-dimethylhydrazine 0.01%+isobutyl alcohol N,N-dimethylhydrazine 0.01%+phenol 0.01% Butylene oxide 0.2%+isobutyl alcohol 0.07%- Butylene oxide 0.2%+phenol 0.01% Isobutyl alcohol 0.07%+phenol 0.01% N,N-dimethylhydrazine 0.01%,-
- a stabilizing composition for trichloroethylene comprised of a synergetic mixture, of from about 1 to portions by weight of N,N-dirnethylhydrazine, from about 10 to 100 portions by weight of isobutyl alcohol, from about 1 to 100 portions by weight-of phenol, and from 10 to 1000-portions by weight of butylene oxide.
- a stabilizing composition for trichloroethylene comprised of a synergetic mixture of item about 1 to 100 parts by weight of N,N-dimethylhydrazine, from about 10 to 100 parts by weight of isobutyl alcohol, fi'om about 1 to 100. parts by weight of o-nitrophenol and from 10 to 1000 parts by weight of propylene oxide.
- a method of stabilizing trichloroethylene for preventing its acidic decomposition, especially during the degreasing of metals comprising the step of intimately mixing to the trichloroethylene small quantities of a synergetic quaternary mixture of N,N-dimethy1hydrazine, isobutyl alcohol, butylene oxide and phenol.
- a method of stabilizing trichloroethylene for preventing its acidic decomposition, especially during the degreasing of metals comprising the step of intimately mixing to the trichloroethylene small quantities of a synergetic quaternary mixture of from about 1 to 100 parts by weight of N,N-dimethylhydrazine, from about 10 to 100 parts by weight of isobutyl alcohol, from about 1 to 100 parts by weight of phenol and from about 10 to 1000 parts by weight of butylene oxide.
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Business, Economics & Management (AREA)
- Emergency Management (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States PatentO METHOD OF STABILIZING TRICHLOROETHYL- AND STABILIZING COMPOSITION THERE- Germano Patron and Antonio Ferri, Milan, Italy,
assignors to Sicedison Sct., Milan, Italy No Drawing. Filed Dec. 17, 1958, Ser. No. 780,957 Claims priority, application Italy June 13, 1958 6 Claims. (Cl. 260652.5)
The present invention relates to a method of stabilizing trichloroethylene and to a stabilizing composition therefor.
It is known that trichloroethylene is utilized industrially in various technical processes, particularly as a solvent for degreasing metals. Since trichloroethylene is an unstable chemical compound, the solvent is easily decomposed during such processes. The phenomena of decomposition of trichloroethylene are enhanced by the presence of air, light, moisture andheat, particularly.
when the solvent is in contact with metallic surfaces, such as iron and aluminum- As these phenomenaar e'ofi'an autocatalytic nature, it is most important to effectively stabilize the solvent, especially in view of the fact-that the hydrochloric .acid formed by the decomposition of trichloroethylene develops fonexample in steel or alumi= num articles, which are beingpdegreased, thejchloridejof these metals," which chlorides, in turn, enhance very much thedecomposition process of "the solvent under' formation of more hydrochloric acid andlsubseque'nt strong corrosion of the metallic articles being degreas ed.
It is known in the art to use various types of organic substances for stabilizing trichloroethylene, such as the amines, phenols, alcohols, epoxides and esters; these subcomposition of thelatter vwhenus'ed in processes for, de-
greasing metals. s
It is another object of our invention toimprove the conditions of working with trichloroethyl'ene asla solvent by providing a method and stabilizing composition which suppress the accumulation of acid'products in trichldrb ethylene or neutralizesthe same when formed.
The objects of ourinvention are attained with the aid of our technically improved method of stabilizing tri ice ideneazine, and dimethylketazine, and is admixed to trichloroethylene in amounts of from 0.01% to 0.02% b weight approximately.
The epoxide may be, for instance, one of the group comprising butylene oxide, propylene oxide, amylene oxide, or chloropropylene oxide and is added to trichloroethylene in amounts of'fromn0.2% to 0.3% by weight approximately.
The alcohol may be one of the groupcomprising isobutyl alcohol, butyl alcohol, propyl alcohol, isopropyl alcohol, amyl alcohol, isoamyl alcohol, ethyl alcohol, and may be added to trichloroethylene in amounts of from 0.05% to 0.1% by weight approximately.
The phenolic compound may be chosen from the grou comprising phenol, thymol, ortho-nitrophenol, eugenol, is0propyl-p-hydroxyanisol, ethyl-p-hydroxyanisol, and should be added to trichloroethylene preferably in quan tities of from 0.005 to 0.01% by weight approximately.
The quantities of the components of the synergetic mixture may be chosen larger or smaller than the amounts given above depending upon the stabilizing effects to be attained and according to the other adjuvants which may be present in the solvent.
Such adjuvants are mentioned in our copendihg appii cation Serial No. 747,566, filed July 18, 1958, now abandoned, and maybe for instance, esters or alcohols" and the like compounds which may be added'tothe tiichloroethylene degreasing solvent without afiecting intrinsically or substantially the synergetic effect of the quaternary mixture of the present invention. i
The synergetic mixture according to the invention may contain one or several substances for each'type of the components mentioned further above, and. chosen-from the list of substances mentioned for each type. 1 For .example, the group of the phenols may be represented the synergetic mixture not only by phenol itself, but may also consist of a mixture of phenol and th'ymol; as reprlesentative of the class of epoxides, a mixture of propyl ene oxide and butylene oxide may be added, and the' same applim to the other two groups, to be present as components in the synergetic mixture.
The technical advantages achieved with the present in:
vention are illustrated by the following test series in which" samples of" trihlorqethyleryi, s ebi ils. b 'yasili me h: ods, are classified according to their stability properties as revealed on the basis of a 48-hour accelerated oxidation test as specified in U.S.A. Army-Navy-Aeronautical Specification MILT70 03 and Fede r al Specification OT- chloroethylene which makes use of a heretofore unknown synergetic mixture. 7
Our invention is based on thediscovery that it is possible to produceasynergetib action of stabilizing trichloroethylene when a quaternary combination is added to trichloroeithylene, the mixture containing a hydrazine derivative, 'an epoxide, an alcohol and-a phenolic comw h" The hydrazine, derivative may .be one of the group werei NNiiPifllYlllYdWH? zae na i fl This stability test consists essentially in causing 200 m1. of trichloroethylene to. boil for 48 hours in a Pyr'ex flask of 500 ml. with reflux condenser and causinga stream of gaseous oxygen saturated'with watertd bubble through the solvent in the flask byway ot a glas'sltiibQe having: a diameter of 3 mmL at a speed of 10 61-2; bubbles per minute; a b x 2 x94 inch SAE, steel strip is suspended inthe vapor "phase whilefa A'x x inch SAE steel strip is introduced "intofthefflask .iiijthe liquid ase a 1'50 ,w.'- frosted light bulb is used.- but s he a agre nether At the end of the test, the acidity of the trichloroethylene isdetermined. The percentages of the various adjuvants are given by weight. The pH values are determined in the aqueous extracts of trichloroethylene after the completion of the stability test by using in each case the same ratio of waterztrichloroethylene of 1: 1. All of the tests were repeated two or three times and the results averaged.
TEST SERIES I Examples 115 This test series was conducted to demonstrate the stabilizing action of the synergetic mixture of butylene oxide and isobutyl alcohol+phenol-l-N,N-dimethylhydrazine. Table I shows the results of the tests on the basis of Examples 1 through 15: Examples 1 to 4 were carried out with individual stabilizing compounds; Examples 5 to with binary mixture, Examples 11 to 14 with ternary mixtures and Example 15 finally with the quaternary mixture according to our present invention. It will be noted from the results shown in Table I that the pH value of the trichloroethylene samples stabilized with individual stabilizing compounds or with binary and ternary mixtures is much lower than 7.0 and thus noticeably acid, whereas the pH value of the sample stabilized with the quaternary mixture of butylene oxide+, isobutyl alcohol+phenol+N,N-dimethylhydrazine remains practically neutral after the completion of the stability test.
TABLE I pH of trlchloro- Sample ethylene No. Stabilizers added to trichloroethylene after accelerated oxidation N,N-dimethylhydrazine 0.01% 1-2 Butylene oxide 0.2% 7-2. Isobutyl alcohol 0.07% 7-2. Phenol 0.01% 0-2. p N,N-dimethylhydrazine 0.01%+butylene oxide 3-2.
0. 6; N ,N-dimethylhydrazine 0.01%+isobutyl alcohol N,N-dimethylhydrazine 0.01%+phenol 0.01% Butylene oxide 0.2%+isobutyl alcohol 0.07%- Butylene oxide 0.2%+phenol 0.01% Isobutyl alcohol 0.07%+phenol 0.01% N,N-dimethylhydrazine 0.01%,-|-buty1ene oxide 0.2%+isobutyl alcohol 0.07%. N,N-dimethylhydrazine 0.01%+butylene oxide 3. 4-3. 7
0.2%+phenol 0.01%. N,N-dimethylhydrazine 0.0l%+isobutyl al- 3.2-2.6
cohol 0.07%+phenol 0.01%. Buiiylenleooglige 0.2%+isobutyl alcohol 0.07%+ 2. 5-2. 8 p eno 15 N,N-dimethyl hydrazlne 0.01%+buty1ene oxide 6.6-7.0 0.2%+isobutyl alcohol 0.07%+phenol 0.01%.
TEST SERIE II Examples 16-30 TABLE II 1311 of trichloro- Sample ethylene No. Stabilizers added to trichloroethylene after accelerated oxidation test N,N-dimethylhydrazine 0.01% 1- Propylene oxide 0.2%. Isobutyl alcohol 0.07%.
2. 4 l. 2 1. 7 0 o-Nitrophenol 0.01% 2. 7- 9 N ,N iimethylhydrazine 0.01%+propylene oxide 2. 1- 4 0.2 NbN-Zdimethylhydrazine 0.01%+isobutyl alcohol 2. 3-2. 6
.0 N,N-d7imethy1hydrazine 0.01%+o-nitrophenol 2. 5-2. 8
0.01 Propylene oxide 0.2%+isobutyl alcohol 0.07%.-. 2. 9-3. 2 Propylene oxide 0.2%+n-nitrophenol 0.01% 1. 9-2. 2 Isobutyl alcohol 0.07%+o-nitrophenol-0.01%- 2. 0-2. 2 N,N-dimethylhydraziue 0.0l%+propylene oxide 3. 7-4. 0
0.2%+isobutyl alcohol 0.07%. N,N-dimethylhydrazine 0.01%+propylene oxide 4. 2-4. 5
0.2%+o-nitrophenol 0.01%. N,N-dimethylhydrazine 0.0l%+isobutyl alcohol 3. l-3. 3
0.07%+o-nitr0phenol 0.01%. Propylene oxide 0.2%+isobutyl alcohol 0.07%+ 2.1-2.3
o-nitrophenol 0.01%. N,N-dimethy1hydrazine 0.01%+propylene oxide 6. 5-7. 0
0.2%+isobutyl alcohol 0.07%+o-nitrophenol 0.01%.
We claim:
1. A trichloroethylene composition stabilized against acidic decomposition, particularly during its use for degreasingmetals, which comprises small quantities, intimately mixed and synergetically active, of N,N-dimethylhydrazine, isobutyl alcohol, butylene oxide, and phenol.
2. A stabilizing composition for trichloroethylene comprised of a synergetic mixture, of from about 1 to portions by weight of N,N-dirnethylhydrazine, from about 10 to 100 portions by weight of isobutyl alcohol, from about 1 to 100 portions by weight-of phenol, and from 10 to 1000-portions by weight of butylene oxide.
3. A trichloroethylene composition stabilized against acidic decomposition, particularly during its use for the degreasing of metals, which comprises small quantities, intimately mixed and synergetically active, of N,N-dimethylhydrazine, isobutyl alcohol, propylene oxide and onitrophenol.
4. A stabilizing composition for trichloroethylene comprised of a synergetic mixture of item about 1 to 100 parts by weight of N,N-dimethylhydrazine, from about 10 to 100 parts by weight of isobutyl alcohol, fi'om about 1 to 100. parts by weight of o-nitrophenol and from 10 to 1000 parts by weight of propylene oxide.
5. A method of stabilizing trichloroethylene for preventing its acidic decomposition, especially during the degreasing of metals, comprising the step of intimately mixing to the trichloroethylene small quantities of a synergetic quaternary mixture of N,N-dimethy1hydrazine, isobutyl alcohol, butylene oxide and phenol.
6. A method of stabilizing trichloroethylene for preventing its acidic decomposition, especially during the degreasing of metals, comprising the step of intimately mixing to the trichloroethylene small quantities of a synergetic quaternary mixture of from about 1 to 100 parts by weight of N,N-dimethylhydrazine, from about 10 to 100 parts by weight of isobutyl alcohol, from about 1 to 100 parts by weight of phenol and from about 10 to 1000 parts by weight of butylene oxide.
References Cited in the tile of this patent UNITED STATES PATENTS 2,008,680 Carlisle et a1. July 23, 1935 2,043,257 Missbach June 9,, 1936 2,371,644 Eetering et al. Mar. 20, 1945 2,797,250 Copelin June 25,1957
I FOREIGN PATENTS 787,726 Great Britain Dec. 1-1, 1957
Claims (2)
1. A TRICHLOROETHYLENE COMPOSITION STABILIZED AGAINST ACIDIC DECOMPOSITION, PARTICULARLY DURING ITS USE FOR DEGREASING METALS, WHICH COMPRISES SMALL QUANTITIES, INTIMATELY MIXED AND SYNERGETICALLY ACTIVE, OF N,N-DIMETHYLHYDRAZINE, ISOBUTYL ALCOHOL, BUTYLENE OXIDE, AND PHENOL.
3. A TRICHLOROETHYLENE COMPOSITION STABILIZED AGAINST ACIDIC DECOMPOSITION, PARTICULARLY DURING ITS USE FOR THE DEGREASING OF METALS, WHICH COMPRISES SMALL QUANTITIES, INTIMATELY MIXED AND SYNERGETICALLY ACTIVE, OF N,N-DIMETHYLHYDRAZINE, ISOBUTYL ACOHOL, PROPYLENE OXIDE AND ONITROPHENOL.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3000977A true US3000977A (en) | 1961-09-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US3000977D Expired - Lifetime US3000977A (en) | Method of stabilizing trichloroethyl- |
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| Country | Link |
|---|---|
| US (1) | US3000977A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3188355A (en) * | 1959-08-05 | 1965-06-08 | Detrex Chem Ind | Stabilization of trichlorethylene |
| US3197345A (en) * | 1960-03-21 | 1965-07-27 | Hooker Chemical Corp | Process and composition for phosphatizing metals |
| US3281480A (en) * | 1961-08-09 | 1966-10-25 | Pittsburgh Plate Glass Co | Stabilization of methyl chloroform |
| US3406213A (en) * | 1965-03-12 | 1968-10-15 | Montedison Spa | Process for stabilizing halogenated hydrocarbons |
| US3676507A (en) * | 1969-03-24 | 1972-07-11 | Ici Ltd | Stabilized trichloroethylene |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2008680A (en) * | 1931-03-03 | 1935-07-23 | Du Pont | Stabilization of halogenated hydrocarbons |
| US2043259A (en) * | 1933-10-09 | 1936-06-09 | Stauffer Chemical Co | Stabilized carbon tetrachloride |
| US2043257A (en) * | 1933-10-09 | 1936-06-09 | Stauffer Chemical Co | Preservation of chlorinated hydrocarbons |
| US2371644A (en) * | 1942-10-01 | 1945-03-20 | Westvaco Chlorine Products Cor | Degreasing process |
| US2797250A (en) * | 1954-05-13 | 1957-06-25 | Du Pont | Stabilization of chlorinated hydrocarbons |
| GB787726A (en) * | 1955-06-16 | 1957-12-11 | Columbia Southern Chem Corp | A method in or relating to stabilization of halogenated hydrocarbons |
-
0
- US US3000977D patent/US3000977A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2008680A (en) * | 1931-03-03 | 1935-07-23 | Du Pont | Stabilization of halogenated hydrocarbons |
| US2043259A (en) * | 1933-10-09 | 1936-06-09 | Stauffer Chemical Co | Stabilized carbon tetrachloride |
| US2043257A (en) * | 1933-10-09 | 1936-06-09 | Stauffer Chemical Co | Preservation of chlorinated hydrocarbons |
| US2371644A (en) * | 1942-10-01 | 1945-03-20 | Westvaco Chlorine Products Cor | Degreasing process |
| US2797250A (en) * | 1954-05-13 | 1957-06-25 | Du Pont | Stabilization of chlorinated hydrocarbons |
| GB787726A (en) * | 1955-06-16 | 1957-12-11 | Columbia Southern Chem Corp | A method in or relating to stabilization of halogenated hydrocarbons |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3188355A (en) * | 1959-08-05 | 1965-06-08 | Detrex Chem Ind | Stabilization of trichlorethylene |
| US3197345A (en) * | 1960-03-21 | 1965-07-27 | Hooker Chemical Corp | Process and composition for phosphatizing metals |
| US3281480A (en) * | 1961-08-09 | 1966-10-25 | Pittsburgh Plate Glass Co | Stabilization of methyl chloroform |
| US3406213A (en) * | 1965-03-12 | 1968-10-15 | Montedison Spa | Process for stabilizing halogenated hydrocarbons |
| US3676507A (en) * | 1969-03-24 | 1972-07-11 | Ici Ltd | Stabilized trichloroethylene |
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