CA1049567A - Inhibition of aromatic compound degradation of methylene chloride - Google Patents
Inhibition of aromatic compound degradation of methylene chlorideInfo
- Publication number
- CA1049567A CA1049567A CA191,978A CA191978A CA1049567A CA 1049567 A CA1049567 A CA 1049567A CA 191978 A CA191978 A CA 191978A CA 1049567 A CA1049567 A CA 1049567A
- Authority
- CA
- Canada
- Prior art keywords
- methylene chloride
- metals
- methyl
- composition
- combinations
- 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
Links
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 title claims abstract description 175
- 150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 14
- 238000006731 degradation reaction Methods 0.000 title claims abstract description 14
- 230000015556 catabolic process Effects 0.000 title claims abstract description 13
- 230000005764 inhibitory process Effects 0.000 title 1
- 229910052751 metal Inorganic materials 0.000 claims abstract description 45
- 239000002184 metal Substances 0.000 claims abstract description 45
- 150000002739 metals Chemical class 0.000 claims abstract description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 33
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims abstract description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 20
- -1 N-methyl pyrolle Chemical compound 0.000 claims abstract description 13
- 238000005238 degreasing Methods 0.000 claims abstract description 13
- 229910001507 metal halide Inorganic materials 0.000 claims abstract description 12
- 150000005309 metal halides Chemical class 0.000 claims abstract description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 10
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229940043279 diisopropylamine Drugs 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 24
- 230000000087 stabilizing effect Effects 0.000 claims description 15
- 150000004820 halides Chemical class 0.000 claims description 11
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims 5
- 229940073584 methylene chloride Drugs 0.000 description 43
- 239000002904 solvent Substances 0.000 description 24
- 229910052782 aluminium Inorganic materials 0.000 description 22
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 22
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 19
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 13
- 229910052725 zinc Inorganic materials 0.000 description 11
- 239000011701 zinc Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229910052742 iron Inorganic materials 0.000 description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000013112 stability test Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- WVMOSGGTBJTKGW-UHFFFAOYSA-N 1,2,3,4-tetramethylbenzene;1,2,4,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C=C1C.CC1=CC=C(C)C(C)=C1C WVMOSGGTBJTKGW-UHFFFAOYSA-N 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 238000013494 PH determination Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 230000004580 weight loss Effects 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
- C23G5/02883—Nitrogen-containing compounds
- C23G5/0289—N-heterocyclics
-
- 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
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)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33500273A | 1973-02-23 | 1973-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1049567A true CA1049567A (en) | 1979-02-27 |
Family
ID=23309810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA191,978A Expired CA1049567A (en) | 1973-02-23 | 1974-02-07 | Inhibition of aromatic compound degradation of methylene chloride |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5217002B2 (cs) |
| AT (1) | AT331769B (cs) |
| BE (1) | BE811478A (cs) |
| CA (1) | CA1049567A (cs) |
| CH (1) | CH593882A5 (cs) |
| CS (1) | CS174232B2 (cs) |
| ES (1) | ES423372A1 (cs) |
| FR (1) | FR2219247A1 (cs) |
| IT (1) | IT1004336B (cs) |
| NL (1) | NL157286B (cs) |
| SE (1) | SE394693B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4032584A (en) * | 1976-05-03 | 1977-06-28 | Stauffer Chemical Company | Stabilized methylene chloride |
| DE3108168A1 (de) * | 1981-03-04 | 1982-09-16 | Wacker-Chemie GmbH, 8000 München | "mittel zur stabilisierung von trichlorethylen und trichlorethylen, enthaltend dieses mittel" |
| FR2601703B1 (fr) * | 1986-07-21 | 1993-05-07 | Atochem | Composition a base de chlorure de methylene - son utilisation pour l'enlevement des films photoresist |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2008680A (en) * | 1931-03-03 | 1935-07-23 | Du Pont | Stabilization of halogenated hydrocarbons |
| DE1111479B (de) * | 1956-09-17 | 1961-07-20 | Du Pont | Entfettungsmittel fuer Metalle |
| FR1263893A (fr) * | 1960-04-30 | 1961-06-19 | Ici Ltd | Procédé de stabilisation d'hydrocarbures chlorés |
-
1974
- 1974-02-07 CA CA191,978A patent/CA1049567A/en not_active Expired
- 1974-02-18 ES ES423372A patent/ES423372A1/es not_active Expired
- 1974-02-21 AT AT141574A patent/AT331769B/de not_active IP Right Cessation
- 1974-02-22 FR FR7406067A patent/FR2219247A1/fr active Granted
- 1974-02-22 SE SE7402360A patent/SE394693B/xx unknown
- 1974-02-22 NL NL7402471A patent/NL157286B/xx unknown
- 1974-02-22 JP JP2132474A patent/JPS5217002B2/ja not_active Expired
- 1974-02-22 CS CS134074A patent/CS174232B2/cs unknown
- 1974-02-22 CH CH259174A patent/CH593882A5/xx not_active IP Right Cessation
- 1974-02-22 BE BE141308A patent/BE811478A/xx unknown
- 1974-02-25 IT IT4867874A patent/IT1004336B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| NL157286B (nl) | 1978-07-17 |
| BE811478A (fr) | 1974-08-22 |
| FR2219247B1 (cs) | 1976-10-08 |
| JPS49134606A (cs) | 1974-12-25 |
| CH593882A5 (cs) | 1977-12-30 |
| JPS5217002B2 (cs) | 1977-05-12 |
| SE394693B (sv) | 1977-07-04 |
| AU6589374A (en) | 1975-08-28 |
| NL7402471A (cs) | 1974-08-27 |
| ATA141574A (de) | 1975-12-15 |
| CS174232B2 (cs) | 1977-03-31 |
| DE2408702A1 (de) | 1974-09-12 |
| AT331769B (de) | 1976-08-25 |
| ES423372A1 (es) | 1976-12-16 |
| DE2408702B2 (de) | 1975-09-25 |
| FR2219247A1 (en) | 1974-09-20 |
| IT1004336B (it) | 1976-07-10 |
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