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)
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&quot) |
| BE (1) | BE628386A (en&quot) |
| CH (1) | CH418316A (en&quot) |
| DE (1) | DE1220410B (en&quot) |
| ES (1) | ES295082A1 (en&quot) |
| NL (2) | NL289737A (en&quot) |
| SE (1) | SE311898B (en&quot) |
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 (de) * | 1957-12-19 | 1960-06-25 | Solvay | Verfahren zur Stabilisierung chlorierter Kohlenwasserstoffe |
| 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 NL120684D patent/NL120684C/xx active
- NL NL289737D patent/NL289737A/xx unknown
- BE BE628386D patent/BE628386A/xx unknown
-
1964
- 1964-01-07 ES ES0295082A patent/ES295082A1/es not_active Expired
- 1964-01-14 DE DES89054A patent/DE1220410B/de active Pending
- 1964-01-17 CH CH51064A patent/CH418316A/fr 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 (de) * | 1957-12-19 | 1960-06-25 | Solvay | Verfahren zur Stabilisierung chlorierter Kohlenwasserstoffe |
| 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 |
|---|---|
| NL120684C (en&quot) | |
| CH418316A (fr) | 1966-08-15 |
| SE311898B (en&quot) | 1969-06-30 |
| DE1220410B (de) | 1966-07-07 |
| ES295082A1 (es) | 1964-04-01 |
| BE628386A (en&quot) | |
| NL289737A (en&quot) |
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