US3293312A - Stabilized chlorinated hydrocarbon compositions - Google Patents
Stabilized chlorinated hydrocarbon compositions Download PDFInfo
- Publication number
- US3293312A US3293312A US344078A US34407864A US3293312A US 3293312 A US3293312 A US 3293312A US 344078 A US344078 A US 344078A US 34407864 A US34407864 A US 34407864A US 3293312 A US3293312 A US 3293312A
- Authority
- US
- United States
- Prior art keywords
- chlorinated hydrocarbon
- pyrocatechol
- trichlorethylene
- phenolic compounds
- phenol
- 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
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 title claims description 22
- 239000000203 mixture Substances 0.000 title claims description 12
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 19
- 150000002989 phenols Chemical class 0.000 claims description 17
- 230000002195 synergetic effect Effects 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 7
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000006641 stabilisation Effects 0.000 claims description 4
- 238000011105 stabilization Methods 0.000 claims description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 10
- 229960003742 phenol Drugs 0.000 description 10
- 230000000087 stabilizing effect Effects 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229950011008 tetrachloroethylene Drugs 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance 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
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical class CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical class ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 description 1
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- OWXJKYNZGFSVRC-UHFFFAOYSA-N 1-chloroprop-1-ene Chemical class CC=CCl OWXJKYNZGFSVRC-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- FRPHFZCDPYBUAU-UHFFFAOYSA-N Bromocresolgreen Chemical compound CC1=C(Br)C(O)=C(Br)C=C1C1(C=2C(=C(Br)C(O)=C(Br)C=2)C)C2=CC=CC=C2S(=O)(=O)O1 FRPHFZCDPYBUAU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- -1 chloromcthanes Chemical class 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000005204 hydroxybenzenes Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052749 magnesium Chemical class 0.000 description 1
- 239000011777 magnesium Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical class CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C23G5/02864—Alcohols
- C23G5/0287—Alcohols aromatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/42—Use of additives, e.g. for stabilisation
Definitions
- the present invention relates to a process for the stabilization of chlorinated hydrocarbons, particularly trichlorethylene and perchlorethylene, in order to avoid decomposition of these products and the simultaneous formation of oxidation products during manufacture, storage or use.
- the improvement of the chlorinated hydrocarbons treated according to the invention can be further shown by applying the well known United States Federal Specification No. O-T-634a, Type II. It may be recalled that this test is carried out as follows. The sample of chlorinated hydrocarbon to be tested is placed in an Erlenmeyer flask heated by an electric lamp and surmounted .by a condenser; a test piece of SAE 1020 steel is suspended above the liquid in the vapour stage and another test piece is placed at the bottom of the flask, that is to say in the liquid phase. Oxygen saturated with water is then continuously introduced for 48 hours, the introduction being effected at the rate of 10 to 12 bubbles of oxygen per minute.
- the mixture of phenolic compounds can in particular replace the single phenol used in the known synergistic compositions, such as those which form the object of our US. patent application Serial No. 314,650 already mentioned and comprise a phenol associated with an epoxy compound having another oxygen-containing function in the molecule.
- a chlorinated hydrocarbon selected from the group consisting of trichloroethylene and perchloroethylene, said chlorinated hydrocarbon containing, for the stabilization of the chlorinated hydrocarbon against oxidation, a synergistic mixture comprising at least two different phenolic compounds each in a concentration of 0.002 to 0.5 gram per liter of chlorinated hydrocarbon, a first of said phenolic compounds being selected from the group consisting of phenol, p-cresol, pyrocatechol, p-methylcatechol and p-tertiary-butylcatechol and a second of said phenolic compounds being selected from the group consisting of pyrocatechol, p-methylcatechol and p-tertiarybutylcatechol.
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
United States Patent 2 Claims. 61460-6525 The present invention relates to a process for the stabilization of chlorinated hydrocarbons, particularly trichlorethylene and perchlorethylene, in order to avoid decomposition of these products and the simultaneous formation of oxidation products during manufacture, storage or use.
It is known that, under the influence of heat and oxygen, chlorinated hydrocarbons undergo an oxidation which is catalysed by different agents such as light and certain metallic salts, in particular salts of iron, aluminum and magnesium.
To retard this oxidation it has been proposed to add to these chlorinated hydrocarbons small quantities of various individual products, such as phenols, alcohols, epoxy compounds, inorganic or organic basic products and so forth. The use of phenols in particular has been indicated in U.S. Patent No. 2,008,680 and German Patent No. 573,105 and the use of alcohols in U.S. Patent No. 2,371,644.
It is also known to add two or more stabilizers which exert a synergistic action. Thus, for example,our U.S. Patent No. 2,935,537 covers the simultaneous use of phenol and an epoxy compound, and that of aniline, pyrrole or a derivative of pyrrole. Other patents cover the simultaneous use of a pentanol and a nitrogen base (US. Patent No. 2,966,424), of phenol and an alcohol (U.S. Patent No. 2,878,518), or of a phenolic compound and an epoxy compound having in the molecule another oxygen-containing function (U.S. patent application Serial No. 314,650, now U.S. Patent No. 3,260,760).
The applicants have now found that a very significant synergistic effect can be obtained for stabilizing chlorinated hydrocarbons by using small quantities of mixtures comprising at least two different phenolic compounds of which the first is selected from hydroxybenzene, alkylsubstituted derivatives thereof, pyrocatechol (orthodiphenol) or the alkyl-subistituted derivatives of the latter, and of which the other phenolic compound or compounds are selected from pyrocatechol, its valkyl-substituted derivatives and the ortho-alcohol-phenols.
Examples of alkyl-substituted derivatives of hydroxy benzene are the cresols and thymol. Of the alkyl-substituted derivatives of pyrocatechol particular mention may be made of p-tertiary-butylcatechol .and p-methylcatechol. An example of an ortho-alcohol-phenol is s aligenol.
The stabilizing action of various compounds and systems of compounds used to improve the resistance of the chlorinated hydrocarbons to decomposition has been shown by various experiments. Some of these have consisted of an accelerated test in the laboratory carried out in the following manner.
Patented Dec. 20, 1966 150 cc. of trichl-orethylene, for example, and a test piece of aluminum, are placed in a 300 cc. flask in an apparatus of the Soxhlet type provided with a cc. extractor. The flask is electrically heated and the trichlorethylene is rapidly brought to boiling under reflux at a constant rate while the apparatus is swept by a current of oxygen and illuminated by a fluorescent lamp of the blue actinic type. During the whole test, the rate of release of acid vapours is measured at the outlet of the apparatus. This rate, very low at first, suddenly becomes very high while the trichlorethylene darkens and changes intoa black gummy mass. The resistance of the trichlorethylene to the test is measured by the'time in hours counted from the start of the experiment, when the sample has reached boiling, until the moment when the release of acid suddenly becomes very rapid and exceeds 15.10" gr. mol/hr.
The following Table 1 shows the resistance to decomposition of trichlorethylene Which has not been stabilized, and of trichlorethylene stabilized by phenolic compounds the combined use of which forms the object of the present invention.
The results show that the use of a combination of a phenol or an orthodiphenol with pyrocatechol or one of its alkyl-substituted derivatives gives a clear synergistic action, since the resistance to oxidation of the trichlor ethylene treated by a mixture of these compounds is very clearly superior to the total of the effects obtained by the sole use of each of the constituents.
The improvement of the chlorinated hydrocarbons treated according to the invention can be further shown by applying the well known United States Federal Specification No. O-T-634a, Type II. It may be recalled that this test is carried out as follows. The sample of chlorinated hydrocarbon to be tested is placed in an Erlenmeyer flask heated by an electric lamp and surmounted .by a condenser; a test piece of SAE 1020 steel is suspended above the liquid in the vapour stage and another test piece is placed at the bottom of the flask, that is to say in the liquid phase. Oxygen saturated with water is then continuously introduced for 48 hours, the introduction being effected at the rate of 10 to 12 bubbles of oxygen per minute. At the end of the test acidity of the chlorinated hydrocarbon is determined in the presence of a coloured indicator; in the tests carried out by us, phenolphthalein prescribed as indicator in the federal specification, was replaced by bromocresol green which is not sensitive to the acidity of carbon dioxide gas. The acidity calculated as'HCl, is expressed in percent by weight of chlorinated hydrocarbon.
The following Table 2 gives some results obtained by applying this technique.
TABLE 2.TESTS ACCORDING TO FEDERAL SPECIFIOA. TION O-T-634a-II (U.S.A.)
Designation of Acidity tests and Quantity and composition of after test corresponding products tested (H 01 persolutions cent by weight) 200 cc. of trichlorethylene containing 0. 0005 pyrocateohol at rate of 5 mg./l. 200 cc. of triohlorethylene containing 0. 0005 p-cresol at rate of 150 mg./l. 1023 cc. of solution A+100 cc. of solution 0. 00035 D 200 cc. of trichlorethylene containing 0. 0005 p-tertiary butyloatechol at rate of 25 mg. E 200 cc. of trichlorethylene containing 0. 0005 p-oresol at rate of 150 mg./l. F %ceof solution D+100 cc. of solution 0. 00025 G 50 of solution D+l50 cc. of solution 0. 00015 H 150Ecc. of solution D+50 cc. of solution 0. 00015 I 200 cc. of trichlorethylene containing 0.00625 saligenol at rate of 200 mg. ll. J 200 cc. of trichlorethylene containing 0. 0063 phenol at rate of 200 mg./l. K 60 cc. of solution I+140 cc. of solutionl 0. 00335 L 140 cc. of solution I+60 cc. of solution J 0. 0035 Here again the results show the synergistic efiect obtained by the use of the combinations according to the invention; it is sufiicient to compare test C with tests A and B, tests F, G and H with tests D and E and tests K and L with tests I and J to establish that the mixtures of stabilizing compounds give an acidity lower than that obtained by each of the constituents taken separately.
The quantities of stabilizing materials to be used lie generally between 0.002 to 0.5 gr./l. for each of the phenolic compounds.
If desired, one may add to the combination of stabilizing substances forming the object of the invention, other known compounds, in particular inorganic or organic substances having an alkaline reaction which modify the initial pH value of the chlorinated hydrocarbon. The mixture of phenolic compounds can in particular replace the single phenol used in the known synergistic compositions, such as those which form the object of our US. patent application Serial No. 314,650 already mentioned and comprise a phenol associated with an epoxy compound having another oxygen-containing function in the molecule.
The stabilizing compositions according to the invention are particularly effective for stabilizing trichlorethylene and perchlorethylene. They can also be used for stabilizing other chlorinated hydrocarbons such as chloromcthanes, dichloroethanes, trichloroethanes, dichloroethylenes, allyl chloride, chloropropanes, chloropropenes, etc., and mixtures thereof.
We claim:
1. A chlorinated hydrocarbon containing, for the stabilization of the chlorinated hydrocarbon against oxidation, a synergistic mixture comprising at least two difierent phenolic compounds each in a concentration of 0.002 to 0.5 gram per liter of chlorinated hydrocarbon, a first of said phenolic compounds being selected from the group consisting of phenol, p-cresol, pyrocatechol, p-methylcatechol and p-tertiary-butylcatechol and a second of said phenolic compounds being selected from the group consisting of pyrocatechol, p-methyleatechol and p-tertiarybutylcatechol.
2. A chlorinated hydrocarbon selected from the group consisting of trichloroethylene and perchloroethylene, said chlorinated hydrocarbon containing, for the stabilization of the chlorinated hydrocarbon against oxidation, a synergistic mixture comprising at least two different phenolic compounds each in a concentration of 0.002 to 0.5 gram per liter of chlorinated hydrocarbon, a first of said phenolic compounds being selected from the group consisting of phenol, p-cresol, pyrocatechol, p-methylcatechol and p-tertiary-butylcatechol and a second of said phenolic compounds being selected from the group consisting of pyrocatechol, p-methylcatechol and p-tertiarybutylcatechol.
References Cited by the Examiner UNITED STATES PATENTS 2,958,712 11/1960 Starks 260-652.5
FOREIGN PATENTS 209,884 6/1960 Austria.
BERNARD HELFIN, Primary Examiner.
LEON ZITVER, Examiner.
M. M. JACOB, Assistant Examiner.
Claims (1)
1. A CHLORINATED HYDROCARBON CONTAINING, FOR THE STABILIZATION OF THE CHLORINATED HYDROCARBON AGAINST OXIDATION, A SYNERGISTIC MIXTURE COMPRISING AT LEAST TWO DIFFERENT PHENOLIC COMPOUND EACH IN A CONCENTRATION OF 0.002 TO 0.5 GRAM PER LITER OF CHLORINATED HYDROCARBON, A FIRST OF SAID PHENOLIC COMPOUNDS BEING SELECTED FROM THE GROUP CONSISTING OF PHENOL, P-CRESOL, PYROCATECHOL, P-METHYLCATECHOL AND P-TERTIARY-BUTYLCATECHOL AND A SECOND OF SAID PHENOLIC COMPOUNDS BEING SELECTED FROM THE GROUP CONSISTING OF PYROCATECHOL, P-METHYLCATECHOL AND P-TERTIARYBUTYLCATECHOL.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE502752 | 1963-02-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3293312A true US3293312A (en) | 1966-12-20 |
Family
ID=3844753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US344078A Expired - Lifetime US3293312A (en) | 1963-02-13 | 1964-02-11 | Stabilized chlorinated hydrocarbon compositions |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3293312A (en) |
| BE (1) | BE628386A (en) |
| CH (1) | CH418316A (en) |
| DE (1) | DE1220410B (en) |
| ES (1) | ES295082A1 (en) |
| NL (2) | NL120684C (en) |
| SE (1) | SE311898B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3676507A (en) * | 1969-03-24 | 1972-07-11 | Ici Ltd | Stabilized trichloroethylene |
| US3852367A (en) * | 1970-12-23 | 1974-12-03 | Central Glass Co Ltd | Stabilized trichloroethylene or tetrachloroethylene |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT209884B (en) * | 1957-12-19 | 1960-06-25 | Solvay | Process for stabilizing chlorinated hydrocarbons |
| US2958712A (en) * | 1958-03-06 | 1960-11-01 | Du Pont | Stabilization of chlorinated hydrocarbons |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2906782A (en) * | 1956-12-21 | 1959-09-29 | Sicedison Spa | Stabilization of the trichloroethylene and stabilizing product therefor |
-
0
- NL NL289737D patent/NL289737A/xx unknown
- NL NL120684D patent/NL120684C/xx active
- BE BE628386D patent/BE628386A/xx unknown
-
1964
- 1964-01-07 ES ES0295082A patent/ES295082A1/en not_active Expired
- 1964-01-14 DE DES89054A patent/DE1220410B/en active Pending
- 1964-01-17 CH CH51064A patent/CH418316A/en unknown
- 1964-01-27 SE SE1000/64A patent/SE311898B/xx unknown
- 1964-02-11 US US344078A patent/US3293312A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT209884B (en) * | 1957-12-19 | 1960-06-25 | Solvay | Process for stabilizing chlorinated hydrocarbons |
| US2958712A (en) * | 1958-03-06 | 1960-11-01 | Du Pont | Stabilization of chlorinated hydrocarbons |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3676507A (en) * | 1969-03-24 | 1972-07-11 | Ici Ltd | Stabilized trichloroethylene |
| US3852367A (en) * | 1970-12-23 | 1974-12-03 | Central Glass Co Ltd | Stabilized trichloroethylene or tetrachloroethylene |
Also Published As
| Publication number | Publication date |
|---|---|
| ES295082A1 (en) | 1964-04-01 |
| NL289737A (en) | |
| DE1220410B (en) | 1966-07-07 |
| CH418316A (en) | 1966-08-15 |
| BE628386A (en) | |
| SE311898B (en) | 1969-06-30 |
| NL120684C (en) |
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