US3564061A - Stabilization of halogenated solvents - Google Patents
Stabilization of halogenated solvents Download PDFInfo
- Publication number
- US3564061A US3564061A US572187A US3564061DA US3564061A US 3564061 A US3564061 A US 3564061A US 572187 A US572187 A US 572187A US 3564061D A US3564061D A US 3564061DA US 3564061 A US3564061 A US 3564061A
- Authority
- US
- United States
- Prior art keywords
- stabilization
- weight
- halogenated
- aliphatic
- stabilizing
- 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
- 230000006641 stabilisation Effects 0.000 title description 14
- 238000011105 stabilization Methods 0.000 title description 14
- 239000002904 solvent Substances 0.000 title description 10
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 abstract description 26
- 150000001875 compounds Chemical class 0.000 abstract description 11
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 abstract description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001336 alkenes Chemical class 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 150000008282 halocarbons Chemical group 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 230000000087 stabilizing effect Effects 0.000 description 9
- -1 alkyl cyanides Chemical class 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 6
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical class CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 5
- 150000002905 orthoesters Chemical class 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000004971 nitroalkyl group Chemical group 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- ZDUOUNIIAGIPSD-UHFFFAOYSA-N 1,1,1-tribromoethane Chemical class CC(Br)(Br)Br ZDUOUNIIAGIPSD-UHFFFAOYSA-N 0.000 description 2
- XFNJYAKDBJUJAJ-UHFFFAOYSA-N 1,2-dibromopropane Chemical compound CC(Br)CBr XFNJYAKDBJUJAJ-UHFFFAOYSA-N 0.000 description 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 2
- RMISVOPUIFJTEO-UHFFFAOYSA-N 2,3-dichlorobutane Chemical class CC(Cl)C(C)Cl RMISVOPUIFJTEO-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000005238 degreasing Methods 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011885 synergistic combination Substances 0.000 description 2
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 1
- PQBOTZNYFQWRHU-UHFFFAOYSA-N 1,2-dichlorobutane Chemical compound CCC(Cl)CCl PQBOTZNYFQWRHU-UHFFFAOYSA-N 0.000 description 1
- KXJFTHCMSHCLGU-UHFFFAOYSA-N 1-ethoxy-2-methylpropane-1,1-diol Chemical compound CCOC(O)(O)C(C)C KXJFTHCMSHCLGU-UHFFFAOYSA-N 0.000 description 1
- UUNIOFWUJYBVGQ-UHFFFAOYSA-N 2-amino-4-(3,4-dimethoxyphenyl)-10-fluoro-4,5,6,7-tetrahydrobenzo[1,2]cyclohepta[6,7-d]pyran-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1C(C#N)=C(N)OC2=C1CCCC1=CC=C(F)C=C12 UUNIOFWUJYBVGQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000696021 Taophila mars Species 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 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
Definitions
- This invention relates to the stabilization of halogenated saturated aliphatic hydrocarbons.
- the desired stabilization of the halogenated aliphatic hydrocarbons is achieved by the combination with the halogenated hydrocarbon to include one or more ortho-esters having the formula in which R is a group selected from the group consisting of hydrogen or an alkyl group containing 1 to 3 carbon atoms and R R and R are groups selected from the group consisting of an alkyl group containing 1 to 3 carbon atoms such as methyl, ethyl and propyl groups with or without substituent groups thereon.
- R, R R and R groups may be the same or they may differ one from another in the compound.
- ortho-ester compounds are suitable for the stabilization of halogenated aliphatic hydrocarbons in accordance with the practice of this invention, namely: triethylorthoformate, trimethylorthoacetate, ethyldimethylorthoacetate and preferably trimethylorthoformate.
- the orthoester is incorporated in the halogenated hydrocarbon in an amount within the range of 0.001 to 15% by weight and preferably 1 to 5% by weight based upon the halogenated hydrocarbon.
- the described synergistic combination is achieved by the combination of the ortho-ester with 0.001 to 3% by weight and preferably 0.1 to 1% by weight of one or more of the compounds containing at least one of the following functions, groups or radicals, namely: aliphatic C -C alcohols, aliphatic C -C thiols, aliphatic C -C esters, aliphatic C -C nitriles such as C -C alkyl cyanides, aliphatic or cyclic ether-oxides such as C C epoxides, aliphatic C -C ketones, C C aliphatic or cyclic acetals, C -C aliphatic organic acid, aliphatic C C iminoether and ketimines, C -C nitroalkyls, oxygenated heterocycles such as pyrane, nitrogenous heterocycles such as pyrrolic, pyrrolinic; aliphatic C -C isocyan
- halogen derivatives of saturated aliphatic hydrocarbons which are stabilized by the process of this invention are the following, which are given by way of illustration, but not by way of limitation, namely: dichloroethanes, trichloroethanes, 1,2-dichloropropane, 1,2 and 2,3-dichlorobutanes, tribromoethanes and 1,2- dibromopropane.
- the plate is partially immersed in the solvent.
- the refluxing was continued until the evolution of acid vapors and/or the development of a discoloration in the solvent and the time for the occurrence of one or the other of such events was recorded as representative of the stabilization ability of the stabilizing agent or stabilizing combination.
- TMOF Trimethylorthoforg ⁇ EF mate
- composition formulated of 0.001 to 15% by Weight of trimethylorthoformate as claimed in claim 1 and 0.001 to 3% by weight of an alkanol having from 1-4 carbon atoms.
- composition formulated of 0.001 to 15% by weight of trimethylorthoformate as claimed in claim 1 and 0.001 to 3% by weight of a compound selected from the group consisting of 1,4-dioxane and trioxane.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR28550A FR1454002A (fr) | 1965-08-17 | 1965-08-17 | Stabilisation des solvants halogénés |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3564061A true US3564061A (en) | 1971-02-16 |
Family
ID=8586766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US572187A Expired - Lifetime US3564061A (en) | 1965-08-17 | 1966-08-15 | Stabilization of halogenated solvents |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3564061A (enrdf_load_stackoverflow) |
| BE (1) | BE685616A (enrdf_load_stackoverflow) |
| CH (1) | CH458311A (enrdf_load_stackoverflow) |
| DE (1) | DE1593254B2 (enrdf_load_stackoverflow) |
| FR (1) | FR1454002A (enrdf_load_stackoverflow) |
| GB (1) | GB1120139A (enrdf_load_stackoverflow) |
| NL (2) | NL152533B (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3723331A (en) * | 1967-11-17 | 1973-03-27 | Pechiney Saint Gobain | Stabilization of saturated halogenated aliphatic hydrocarbons |
| US3864413A (en) * | 1970-01-22 | 1975-02-04 | Norman L Beckers | Stabilized metal chloroform |
| US3876712A (en) * | 1972-08-10 | 1975-04-08 | Ethyl Corp | Stabilized halogenated hydrocarbons |
| US3935287A (en) * | 1972-04-11 | 1976-01-27 | Diamond Shamrock Corporation | Stabilized methyl chloroform |
| US4324757A (en) * | 1979-07-02 | 1982-04-13 | The Dow Chemical Company | Halogenated hydrocarbons inhibited against denickelification with lower alkylcyanide compounds |
| US4992604A (en) * | 1989-07-24 | 1991-02-12 | Ppg Industries, Inc. | Stabilized 1,1,1-trichloroethane compositions |
| US6010997A (en) * | 1998-06-25 | 2000-01-04 | Alliedsignal Inc. | Compositions of 1-bromopropane, nitromethane or acetonitrile and an alcohol |
| US6660701B1 (en) | 2000-10-23 | 2003-12-09 | Polysystems Usa, Inc. | Stabilized solvent system for cleaning and drying |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5319161B2 (enrdf_load_stackoverflow) * | 1971-12-29 | 1978-06-19 |
-
1965
- 1965-08-17 FR FR28550A patent/FR1454002A/fr not_active Expired
-
1966
- 1966-08-15 CH CH1173366A patent/CH458311A/fr unknown
- 1966-08-15 US US572187A patent/US3564061A/en not_active Expired - Lifetime
- 1966-08-16 GB GB36637/66A patent/GB1120139A/en not_active Expired
- 1966-08-17 NL NL666611552A patent/NL152533B/xx unknown
- 1966-08-17 DE DE1966P0040195 patent/DE1593254B2/de active Granted
- 1966-08-17 BE BE685616D patent/BE685616A/xx unknown
-
1976
- 1976-11-04 NL NL7612228A patent/NL7612228A/xx not_active Application Discontinuation
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3723331A (en) * | 1967-11-17 | 1973-03-27 | Pechiney Saint Gobain | Stabilization of saturated halogenated aliphatic hydrocarbons |
| US3864413A (en) * | 1970-01-22 | 1975-02-04 | Norman L Beckers | Stabilized metal chloroform |
| US3935287A (en) * | 1972-04-11 | 1976-01-27 | Diamond Shamrock Corporation | Stabilized methyl chloroform |
| US3876712A (en) * | 1972-08-10 | 1975-04-08 | Ethyl Corp | Stabilized halogenated hydrocarbons |
| US4324757A (en) * | 1979-07-02 | 1982-04-13 | The Dow Chemical Company | Halogenated hydrocarbons inhibited against denickelification with lower alkylcyanide compounds |
| US4992604A (en) * | 1989-07-24 | 1991-02-12 | Ppg Industries, Inc. | Stabilized 1,1,1-trichloroethane compositions |
| US6010997A (en) * | 1998-06-25 | 2000-01-04 | Alliedsignal Inc. | Compositions of 1-bromopropane, nitromethane or acetonitrile and an alcohol |
| US6660701B1 (en) | 2000-10-23 | 2003-12-09 | Polysystems Usa, Inc. | Stabilized solvent system for cleaning and drying |
Also Published As
| Publication number | Publication date |
|---|---|
| BE685616A (enrdf_load_stackoverflow) | 1967-02-17 |
| DE1593254B2 (de) | 1976-12-23 |
| NL152533B (nl) | 1977-03-15 |
| DE1593254A1 (de) | 1971-01-21 |
| NL6611552A (enrdf_load_stackoverflow) | 1967-02-20 |
| GB1120139A (en) | 1968-07-17 |
| FR1454002A (fr) | 1966-07-22 |
| CH458311A (fr) | 1968-06-30 |
| NL7612228A (nl) | 1977-02-28 |
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