US3546304A - Process for stabilizing against decomposition halogenated hydrocarbons,and in particular chlorinated aliphatic hydrocarbons - Google Patents
Process for stabilizing against decomposition halogenated hydrocarbons,and in particular chlorinated aliphatic hydrocarbons Download PDFInfo
- Publication number
- US3546304A US3546304A US722808A US3546304DA US3546304A US 3546304 A US3546304 A US 3546304A US 722808 A US722808 A US 722808A US 3546304D A US3546304D A US 3546304DA US 3546304 A US3546304 A US 3546304A
- Authority
- US
- United States
- Prior art keywords
- hydrocarbons
- trichloroethylene
- perchloroethylene
- weight
- decomposition
- 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
Links
- 238000000354 decomposition reaction Methods 0.000 title description 17
- 230000000087 stabilizing effect Effects 0.000 title description 15
- 150000008282 halocarbons Chemical class 0.000 title description 8
- 238000000034 method Methods 0.000 title description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 title description 3
- 239000002904 solvent Substances 0.000 description 21
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 18
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 17
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 17
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 12
- 238000005238 degreasing Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229910000831 Steel Inorganic materials 0.000 description 6
- 239000005844 Thymol Substances 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- 229960000790 thymol Drugs 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 150000008280 chlorinated hydrocarbons Chemical group 0.000 description 5
- 230000006641 stabilisation Effects 0.000 description 5
- 238000011105 stabilization Methods 0.000 description 5
- -1 di-isobutylene Chemical compound 0.000 description 4
- 230000002045 lasting effect Effects 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 238000005108 dry cleaning Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 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 group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- XJHDWSFEGCYSFP-UHFFFAOYSA-N C=C.ClC(Cl)=O Chemical group C=C.ClC(Cl)=O XJHDWSFEGCYSFP-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000696021 Taophila mars Species 0.000 description 1
- 241000246358 Thymus Species 0.000 description 1
- 235000007303 Thymus vulgaris Nutrition 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- KVIPHDKUOLVVQN-UHFFFAOYSA-N ethene;hydrate Chemical compound O.C=C KVIPHDKUOLVVQN-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000008095 trichloroethylene stabilized Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
- C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
- C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
- C23G5/02854—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons characterised by the stabilising or corrosion inhibiting additives
- C23G5/02883—Nitrogen-containing compounds
Definitions
- the present invention relates to the stabilization of halogenated hydrocarbons against decomposition. More particularly it relates to the stabilization against decomposition of chlorinated hydrocarbons, and especially chlorinated aliphatic hydrocarbons such as trichloroethylene and perchloroethylene, useful as solvents in various industrial processes.
- chlorinated hydrocarbons and more particularly trichloroethylene and perchloroethylene, are widely used in various technical processes. These are especially useful as solvents for fats and other organic substances, for instance in degreasing processes for metals, in processes for the extraction of oils and fats, in the drycleaning of fabrics, etc.
- this decomposition is accelerated through the presence of metals or metal salts as Well as by the direct or indirect products of the decomposition itself, the decomposition thereby proceeding autocatalytically.
- the stabilizing system must furthermore be such as to ensure the neutrality of the solvent even under the most severe conditions (alkalinity of the solvent when imparted by stabilizers having a strong basic character is just as harmful as acidity, because such alkalinity makes the solvent quite unsuited for the degreasing of amphoteric metals such as aluminum and zinc) and furthermore the stabilizing system must exert a lasting stabilizing action both in the liquid phase as well as in the vapor phase customarily encountered during degreasing processes.
- the object of this invention is that of providing a new and efficient stabilizing agent for halogenated hydrocarbons, particularly suited for chlorinated solvents to be used in the degreasing of metals, which, besides exerting a sure and lasting anti-oxidizing action, that is, such as to ensure the inhibition of the formation of phosgene and hydrochloric acid, will also guarantee the neutrality of the solvent even under the most severe operational conditions.
- a stabilizing action of a sure and lasting effectiveness against the decomposition of halogenated hydrocarbons, and in particular of chlorinated hydrocarbons used as solvents in the degreasing of metals is achieved by adding to the halogenated hydrocarbon solvent a stabilizing composition based on the combination of butylene oxide, di-isobutylene, thymol and dimethylbenzalhydrazone.
- the above-mentioned composition may be used alone or in admixture with other stabilizers of previously known yp
- the quantity of stabilizing composition to be added to the halogenated hydrocarbon solvent depends on the type of solvent to be stabilized, on the expected use of the solvent, on the degree of stabilization desired, and on the possible presence of other additives.
- concentrations are preferably used varying from 0.1 to 0.4% by Weight of butylene oxide, from 0.01 to 0.1% by weight of di-isobutylene, from 0.001 to 0.02% by weight of thymol, and from 0.001 to 0.02% by weight of dimethylbenzalhydrazone. Although larger quantities of the several components may be used, they are not necessary.
- Trichloroethylene and perchloroethylene stabilized according to the present invention do not show any tendency to decompose either during storage or during use under the most severe processing conditions such as in the degreasing of metals. Even after long heat-treatments trichloroethylene and perchloroethylene thus stabilized remain limpid and clear.
- the stabilizing composition of this invention in combination with small quantities (for instance, 0.00050.002% by weight) of an alkyl-hydrazine, such as methyland ethyl-monoand symmetrical and/or asymmetrical di-hydrazines.
- an alkyl-hydrazine such as methyland ethyl-monoand symmetrical and/or asymmetrical di-hydrazines.
- halogenated hydrocarbons may be protected against decomposition by the stabilizing composition according to the present invention, such as chloroform, methylchloroform, methylene chloride, carbon tetrachloride, dichloroethylene, trichloroethane, vinylidene chloride, vinyl chloride, etc.
- a small steel plate of x 2 x A inch is suspended in the vapor phase while in the liquid phase a small steel plate of 4 x x inch is introduced.
- a sanded 150 watt lamp is placed under the flask.
- a liquid chlorinated hydrocarbon stabilized against decomposition comprising trichloroethylene or perchloroethylene in admixture with a stabilizing composition consisting essentially of butylene oxide, di-isobutylene, thymol and dimethylbenzalhydrazone in quantities varying, respectively, from about 0.1 to 0.4% by Weight, from about 0.01 to 0.1% by weight, from about 0.001 to 0.02% by weight, and from about 0.001 to 0.02% by weight.
- Trichloroethylene stabilized against decomposition comprising trichloroethylene in admixture with a stabilizing composition consisting essentially of butylene oxide, di-isobutylene, thymol and dimethylbenzalhydrazone in quantities varying, respectively, from about 0.1 to 0.4% by weight, from about 0.01 to 0.1% by weight, from about 0.001 to 0.02% by weight, and from about 0.001 to 0.02% by weight.
- a stabilizing composition consisting essentially of butylene oxide, di-isobutylene, thymol and dimethylbenzalhydrazone in quantities varying, respectively, from about 0.1 to 0.4% by weight, from about 0.01 to 0.1% by weight, from about 0.001 to 0.02% by weight, and from about 0.001 to 0.02% by weight.
- Perchloroethylene stabilized against decomposition comprising perchloroethylene in admixture with a stabilizing composition consisting essentially of from about 0.1 to 0.4% by weight of butylene oxide, of from about 0.01 to 0.1% by weight of di-isobutylene, of from about 0.001 to 0.02% by weight of thyme], and of from about 0.001 to 0.02% by weight of dimethylbenzalhydrazone.
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1516867 | 1967-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3546304A true US3546304A (en) | 1970-12-08 |
Family
ID=11146926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US722808A Expired - Lifetime US3546304A (en) | 1967-04-20 | 1968-04-19 | Process for stabilizing against decomposition halogenated hydrocarbons,and in particular chlorinated aliphatic hydrocarbons |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3546304A (enrdf_load_stackoverflow) |
| BE (1) | BE713963A (enrdf_load_stackoverflow) |
| DE (1) | DE1768227A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1580912A (enrdf_load_stackoverflow) |
| NL (1) | NL6805316A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USB334985I5 (enrdf_load_stackoverflow) * | 1973-02-23 | 1975-01-28 | ||
| US4062901A (en) * | 1972-04-07 | 1977-12-13 | Solvay & Cie. | Process for the stabilization of methylene chloride |
| US4322309A (en) * | 1979-04-27 | 1982-03-30 | A. B. Chance Company | Composition capable of removing hydrophilic and hydrophobic contaminants from surfaces |
| US6429176B1 (en) | 1996-05-10 | 2002-08-06 | Emerald Agrochemicals Company Avv | Rapidly evaporating cleaning compositions |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE684156A (enrdf_load_stackoverflow) * | 1965-07-14 | 1966-12-16 | ||
| US3417152A (en) * | 1960-03-11 | 1968-12-17 | Montedison Spa | Method of stabilizing trichloroethylene |
-
1968
- 1968-04-16 NL NL6805316A patent/NL6805316A/xx unknown
- 1968-04-18 FR FR148525A patent/FR1580912A/fr not_active Expired
- 1968-04-18 DE DE19681768227 patent/DE1768227A1/de active Pending
- 1968-04-19 BE BE713963D patent/BE713963A/xx unknown
- 1968-04-19 US US722808A patent/US3546304A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3417152A (en) * | 1960-03-11 | 1968-12-17 | Montedison Spa | Method of stabilizing trichloroethylene |
| BE684156A (enrdf_load_stackoverflow) * | 1965-07-14 | 1966-12-16 | ||
| US3423476A (en) * | 1965-07-14 | 1969-01-21 | Montedison Spa | Stabilized halocarbon compositions |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4062901A (en) * | 1972-04-07 | 1977-12-13 | Solvay & Cie. | Process for the stabilization of methylene chloride |
| USB334985I5 (enrdf_load_stackoverflow) * | 1973-02-23 | 1975-01-28 | ||
| US3923912A (en) * | 1973-02-23 | 1975-12-02 | Diamond Shamrock Corp | Methylene chloride stabilized with ketones |
| US4322309A (en) * | 1979-04-27 | 1982-03-30 | A. B. Chance Company | Composition capable of removing hydrophilic and hydrophobic contaminants from surfaces |
| US6429176B1 (en) | 1996-05-10 | 2002-08-06 | Emerald Agrochemicals Company Avv | Rapidly evaporating cleaning compositions |
| US6855211B2 (en) | 1996-05-10 | 2005-02-15 | Emerald Agrochemicals Company Avv | Rapidly evaporating cleaning compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| BE713963A (enrdf_load_stackoverflow) | 1968-10-21 |
| NL6805316A (enrdf_load_stackoverflow) | 1968-10-21 |
| FR1580912A (enrdf_load_stackoverflow) | 1969-09-12 |
| DE1768227A1 (de) | 1971-10-28 |
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