GB2024243A - Stabilization of 1,1,1- trichloroethane - Google Patents
Stabilization of 1,1,1- trichloroethane Download PDFInfo
- Publication number
- GB2024243A GB2024243A GB7922751A GB7922751A GB2024243A GB 2024243 A GB2024243 A GB 2024243A GB 7922751 A GB7922751 A GB 7922751A GB 7922751 A GB7922751 A GB 7922751A GB 2024243 A GB2024243 A GB 2024243A
- Authority
- GB
- United Kingdom
- Prior art keywords
- weight
- epoxide
- methylbut
- trichloroethane
- butyl alcohol
- 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.)
- Granted
Links
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 230000006641 stabilisation Effects 0.000 title claims description 8
- 238000011105 stabilization Methods 0.000 title claims description 6
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000000203 mixture Substances 0.000 claims abstract description 25
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 23
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004971 nitroalkyl group Chemical group 0.000 claims abstract description 10
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- -1 cyclic amine Chemical class 0.000 claims abstract description 5
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 30
- 150000002924 oxiranes Chemical class 0.000 claims description 19
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical group CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 13
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical group CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 230000003078 antioxidant effect Effects 0.000 claims description 6
- 235000006708 antioxidants Nutrition 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 229940043279 diisopropylamine Drugs 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical group CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical group ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 3
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 3
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 11
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims 2
- 230000003064 anti-oxidating effect Effects 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 8
- 239000002184 metal Substances 0.000 abstract description 8
- 238000005238 degreasing Methods 0.000 abstract description 6
- 238000004140 cleaning Methods 0.000 abstract description 4
- 150000002739 metals Chemical class 0.000 abstract description 2
- 150000002118 epoxides Chemical class 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 238000005108 dry cleaning Methods 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 239000004411 aluminium Substances 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 238000004821 distillation Methods 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 5
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000006748 scratching Methods 0.000 description 3
- 230000002393 scratching effect Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003333 secondary alcohols Chemical class 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NJZQOCCEDXRQJM-UHFFFAOYSA-N 1-benzylindole Chemical compound C1=CC2=CC=CC=C2N1CC1=CC=CC=C1 NJZQOCCEDXRQJM-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical class CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- BLRHMMGNCXNXJL-UHFFFAOYSA-N 1-methylindole Chemical compound C1=CC=C2N(C)C=CC2=C1 BLRHMMGNCXNXJL-UHFFFAOYSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical class CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- SUNOPHTUNNAFGB-UHFFFAOYSA-N 2-(2-methylphenyl)-1h-indole Chemical compound CC1=CC=CC=C1C1=CC2=CC=CC=C2N1 SUNOPHTUNNAFGB-UHFFFAOYSA-N 0.000 description 1
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical class CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
- CLYFXKBQNAQDOJ-UHFFFAOYSA-N 2-butyl-1h-indole Chemical compound C1=CC=C2NC(CCCC)=CC2=C1 CLYFXKBQNAQDOJ-UHFFFAOYSA-N 0.000 description 1
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical class CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 1
- MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical compound CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 description 1
- SRJCJJKWVSSELL-UHFFFAOYSA-N 2-methylnaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(C)=CC=C21 SRJCJJKWVSSELL-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical group 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000013527 degreasing agent Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical class CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- CCDXIADKBDSBJU-UHFFFAOYSA-N phenylmethanetriol Chemical class OC(O)(O)C1=CC=CC=C1 CCDXIADKBDSBJU-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000004154 testing of material Methods 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0084—Antioxidants; Free-radical scavengers
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Abstract
1,1,1-Trichloroethane is stabilized with respect to metals in the presence of light and/or oxygen-bearing gas by (a) 0.1 to 5% by weight of tertiary butyl alcohol; (b) 0.1 to 5% by weight of 2- methylbut-3-yn-2-ol and/or trioxan, (c) from 0.1 to 5% by weight of at least one C3-8 epoxide or chlorinated epoxide; (d) from 0.1 to 3% by weight of at least one C1-3 nitroalkane; and (e) from 0.001 to 1% by weight of a C4-10 aliphatic or cyclic amine. The resulting composition can be used for degreasing and/or cleaning metal articles, or for dry-cleaning textiles.
Description
SPECIFICATION
Stabilisation of 1,1,1 -trichloroethane
The present invention concerns the stabilisation of 1,1,1 -trichloroethane.
In the description of the invention, percentages given are expressed by weight, unless indicated to the contrary.
It is well known that 1,1,1-trichloroethane is unstable when it is brought into contact with metals such as aluminium and its alloys and magnesium and its alloys. The instability of 1,1,1 -trichloroethane is revealed by decomposition with accompanying formation of hydrochloric acid and other decomposition products, and colouring of the 1,1,1 -trichloroethane. This is a serious disadvantage from the point of view of its use as a solvent for degreasing and/or cleaning metal members or parts.
A very large number of compounds have been put forward as agents for inhibiting decomposition, or for stabilising 1,1,1-trichloroethane. Thus, US Patent No 2,371,644 proposes primary, secondary or tertiary alcohols such as tertiary amyl alcohol are described as being less efficient than primary and secondary alcohols, while US Patent No 3,000,978 refers to tertiary buty alcohol as being more efficient than tertiary amyl alcohol and also more efficient than secondary butyl alcohol, isopropanol, n-propanol or ethanol.
Moreover, US Patent No 2,371,645 describes cyclic esters such as propylene oxide and isobutylene oxide and CanadianPatent No 627,411 proposes incorporating nitromethane in 1,1,1 -trichloroethane.
However, these constituents, taken separately, provide only a very unsatisfactory degree of stability, in particular for prolonged uses of 1,1,1-trichloroethane in degreasing and/or cleaning metal or other articles.
In order to improve the degree of stability of the chlorinated solvent, British Patent No 912,118 discloses the addition to 1,1,1-trichloroethane, of a nitroalkane and an epoxide simultaneously, or a nitroalkane and a monohydroxyl aliphatic alcohol containing up to 5 carbon atoms. However, as the 1,1,1 -trichlornethane is itself made particularly sensitive to decomposition at the temperatures at which it is used as a degreasing and/or cleaning agent, because of the presence of greases, metal surfaces and metal impurities in suspension in the cleaning bath, such combinations of stabilizing agents are unable to provide 1,1,1 -trichlornethane with an effective degree of stability.
Even the ternary combination of nitromethane, tertiary butyl alcohol and 1,2-butylene oxide mentioned in
US Patent No 3,281,480 cannot prevent the formation of an ambercoloured precipitate in the solvent, after contact with aluminium for 24 hours. The same also applies in regard to monohydroxyl aliphatic acetylenic alcohols containing less than 8 carbon atoms, more particularly 2-methylbut-3-yn-2-ol, which are associated with 1,4-dioxan, in accordance with US Patent No 2,838,458.
According to the invention, stabilization of 1,1,1 -trichloroethane is achieved by incorporating in it:
(a) from 0.1 to 5% and preferably from 0.5 to 3.5% by weight of tertiary butyl alcohol;
(b) from 0.1 to 5% and preferably from 0.3 to 3% by weight of at least one of 2-methylbut-3-yn-2-ol and trioxan;
(c) from 0.1 to 5% by weight of at least one C38 epoxide or chlorinated epoxide; (d) from 0.1 to 3% by weight of at least one Cl 3 nitroalkane; and (e) from 0.001 to 1% and preferably from 0.005 to 0.1% by weight of at least one aliphatic, cyclic or heterocyclic C410 amine of a basic nature.
The amines used according to the invention include C410 aliphatic amines, preferably secondary or tertiary, with a straight or branched carbon-bearing chain; C6 aromatic amines substituted by halogen atoms or C1 to C3 alkyl groups; and heterocyclic amines having 1 or 2 nitrogen atoms in the molecule, e.g.
diethylamine, triethylamine, diisopropylamine, di-sec-butylamine, amylamines, hexylamines, pyridines, picolines, morpholinem N-(C1.3 alkyl)morpholines, pyrrolidine, and N-(C1.3 alkyl)pyrrolidines.
Particularly advantageous amines for use in accordance with the invention are N-methyl-morpholine, di-isopropylamine and pyrrolidine.
In the following description, in order not to encumber the text, the percentages given are expressed by weight, unless indicated to the contrary.
When the mixture of tertiary butyl alcohol and 2-methylbut-3-yn-2-ol is associated with 1,1,1-.
trichloroethane, this binary mixture comprises from 1 to 99% of tertiary butyl alcohol and from 99 to 1% of 2-methylbut-3-yn-2-ol and preferably from 25 to 80% of tertiary butyl alcohol for from 75 to 20% of 2-methylbut-3-yn-2-ol.
In accordance with an advantageous embodiment of the invention, trioxan is incorporated in the 1,1,1 -trichloroethane, in proportions of from 0.5 to 3%, without 2-methylbut-3-yn-2-ol.
Representative compounds of the C3to C8 epoxide and chlorinated epoxide include in particular 1,2-butylene oxide, which is preferred, epichlorohydrin, glycidol and its primary, secondary and tertiary methyl, ethyl, propyl, isopropyl, allyl and butyl ethers, 1,2-propylene oxide, styrene oxideand cyclohexene oxide. The preferred proportion of expoxide is from 0.2 to 3% with respect to the 1,1,1 -trichloroethane.
The nitroalkanes are represented by nitromethane, nitroethane and the two isomers of nitropropane. The preferred proportion is from 1 to 2% with respect to the 1,1,1-trichloroethane.
It has in fact been found that the association of the above-mentioned compounds can be particularly advantageous because, in a comparable concentration, it has a stabilizing action substantially better than that achieved by the addition of each of the constituents taken in isolation.
The association of the above-indicated compounds may further be reinforced by the addition, as an anti-oxident, of at least one phenol and/or nitrogenous heterocycle having from 3 to 5 carbon atoms and from 1 to 2 nitrogen atoms with optionally an oxygen atom in the ring, in amounts of up to 1% and preferably from 0.001 to 0.1 % with respect to the 1,1,1 4richloroethane.
Among examples of suitable phenols are monohydric phenols such as phenol, cresols, ethylphenols, butylphenols, in particularp-ter-butylphenol, thymol, naphthols, methylnaphthols and eugenol; C1 or C2 alkyl ethers of monophenols such as anisol, guaiacol and 2-ethoxy phenol; diphenols such as resorcinol, pyrocatechol, naphthoquinone and in particular hydroquinone; C1 or C2walkyl ethers of said diphenols such as the monomethyl ether of hydroquinone; and triphenols such as pyrogallol, phloroglucinol, hydroxyhydroquinone and trihydroxytoluenes.
Examples of heterocycles with one nitrogen atom include pyrrole, N(C1.4)pyrroles, preferably Nmethylpyrrole, indole, 1 -methylindole, 2-butylindole, 2-phenylindole, 2-toluylindole, 1 -benzylindole and their respective isomers; oxazole and isoxazole are representative of heterocycles with one nitrogen atom and an oxygen atom.
Examples of nitrogen heterocycles with 2 nitrogen atoms include imidazole, pyrazole, pyrazoline, pyrazolidine, imidazoline, imidazolidine, piperazine and their N-(C1.4alkyl)ated derivatives, pyrazine, pyrimidine and pyridazine.
The invention also provides a composition which comprises 1,1,1-trichloroethane containing:
(a) from 0.1 to 5% and preferably from 0.5 to 3.5% by weight of tertiary butyl alcohol;
(b) from 0.1 to 5% and preferably 0.3 to 3% by weight of at least one of 2-methylbut-3-yn-2-ol and trioxan;
(c) from 0.1 to 5% by weight of at least C3-8 epoxide or chlorinated epoxide;
(d) from 0.1 to 3% by weight of at least one C1.3 nitroalkane.
(e) from 0.001% to 1% and preferably from 0.005% to 0.1% by weight of at least one aliphatic, cyclic or heterocyclic C4.10 amine of a basic nature; and
(f) as anti-oxidant, from 1 to 1% and preferably less than 0.2% of at least one phenol and/or nitrogen heterocycle having from 3 to 5 carbon atoms, 1 or 2 nitrogen atoms and possibly an oxygen atom in the ring, as defined above; the said proportions being expressed with respect to the 1,1,1 -trichloroethane in the composition.
The preferred compositions of the invention essentially comprise 1,1,1 -trichloroethane containing:
(a) from 1 to 3% of tertiary butyl alcohol;
(b) from 0.5 to 2.5% of 2-methylbut-3-yn-2-ol and up to 2.5% of trioxan;
(c) from 0.2 to 3% of 1 ,2-butylene oxide;
(d) from 0.5 to 1.5% of nitromethane and/or nitroethane; and
(e) from 0.005 to 0.1% of N-methyl-morpholine and/or diisopropylamine.
The following Examples are given to illustrate but not limit the invention and to set forth its specific advantages.
Example 1
The following compounds were incorporated in 1,1,1-trichloroethane: tertiary butyl alcohol 2.0
2-methylbut-3-yn-2-ol 1.5
1,2-butylene oxide 0.45
nitromethane 1.3
N-methylmorpholine 0.008
The resulting composition was tested by successive distillation. This comprises distilling itfourtimes in
succession and in each distillation step collecting only the first 90% by volume that passes. The test in
respect of scratching of aluminium plates in accordance with standard ASTM D 2943-71 Twas carried out on
each ofthefourdistillates.
The scratching test is to determine the aptitude of the association of stabilizing agents in 1,1,1
trichloroethane, to prevent degradation of the chlorinated solvent in the presence of aluminium or
aluminium alloys. It comprises taking a piece of metal that has been cleaned and degreased, of quality AA
1100 (Standard ASTM corresponding to AFNOR A 45 symbol aluminium), immersing it in 50 cc of stabilized 1,1,1 -trichloroethane at ambient temperature, and scratching it by means of a mild steel rod. After a period of
time (1 hour) sufficient to allow any reaction to occur, the presence or absence of bubbles, colouring of the
solvent or the presence of dark-coloured resinous products is noted. The 1,1,1 -trichloroethane is suitably
stabilized if no reaction is observed.
The above composition passes this test, without any trace of reaction on the aluminium plates being observed.
A very severe long-term stabilization test was also carried out, viz. the test of the BAM (German Federal
Institute for Testing of Materials). This test comprises carrying out three operations on a mixture of 100 cc of stabilized 1,1,1-trichloroethane and 100 cc of toluene:
operation 1: addition of 18 g of aluminium in the form of thin sheets or plates, and 0.7 g of aluminium
chloride
operation 2: as operation 1, also adding 1 g of zinc stearate
operation 3: as operation 1, also adding 10 ml of oleic acid.
For each operation, the mixtures were refluxed, the bath temperature being 11 4'C, for a period of 18 hours.
The stabilized 1,1,1 -trichloroethane was then distilled into three equal portions, in accordance with standard DIN 51 751, and then operation 1 was carried out on 100 cc of toluene.
The solvent was admitted as satisfying the test if there was no violent exothermic reaction recorded in the course of each of the six operations considered separately.
The composition set out hereinbefore passed the test, without any violent exothermic reaction being observed.
Example 2
1,1,1-Trichloroethane containing: tertiary butyl alcohol 2.0 2-methylbut-3-yn-2-ol 1.85 1 ,2-butylene oxide 0.45 nitroethane 1.3 pyrrolidine 0.01 successfully passed the successive distillation tests and the BAM tests described in Example 1.
Example 3
1,1,1-Trichloroethane to which the following were added: tertiary butyl alcohol 1.7 2-methylbut-3-yn-2-ol 2.0 1,2-butylene oxide 0.45 nitroethane 0.6 nitromethane 0.5
N-methylmorpholine 0.005 also successfully passed the successive distillation and BAM tests described in Example 1.
Example 4
1,1,1-Trichloroethane to which the following were added: tertiary butyl alcohol 2.0 2-methylbut-3-yn-2-ol 1.5 1,2-butylene oxide 0.45 nitromethane 1.3
N-methylpyrrole 0.008
N-methyl-morpholine 0.01 also successfully passed the successive distillation and BAM tests described in Example 1.
Example 5
In order to demonstrate the attraction of adding an associated amine to the other stabilizing agents of the invention, the following test was carried out:
98 ml of stabilized 1,1,1 -trichloroethane, mixed with 2 ml of a mixture of white spirit and water (in a proportion of 90% by volume of white spirit for 10% by volume of water) was boiled under reflux for 72 hours. The pH of the solvent was measured before and after the test.
With stabilized 1,1,1 -trichloroethane in accordance with the formula set out in Example 4, but without
N-methyl-morpholine, the pH changed from 6.7 before the test to 4.5 after 72 hours of reflux (for this pH, it is known that the solvent is particularly corrosive for degreasing machines).
With 1,1,1 -trichloroethane stabilized in accordance with the formula set out in Example 4 (containing 0.01% of N-methyl-morpholine), the pH remained at 8.3 after 72 hours of reflux (at this pH there is virtually no corrosion of degreasing machines).
Example 6 1,1,1-Trichloroethane containing the following substances: tertiary butyl alcohol 2.4 2-methylbut-3-yn-2-ol 2.1 methylglycidic ether 0.5 nitromethane 1.3 diisopropylamine 0.005 successfully passed the successive distillation and BAM tests described in Example 1.
Example 7
The following composition also successfully passed the successive distillation and BAM tests described in
Example 1: 1,1,1-trichloroethane 94.995 tertiary butyl alcohol 2.5 trioxan 1.4 1,2-butylene oxide 0.4 nitromethane 0.7
N-methyl-morpholine 0.005
Claims (20)
1. A process for the stabilization of 1,1 1-trichloroethane, comprising incorporating in it:
(a) from 0.1 to 5% by weight of tertiary butyl alcohol;
(b) from 0.1 to 5% by weight of at least one of 2-methylbut-3-yn-2-ol and trioxan;
(c) from 0.1 to 5% by weight of at least one C38 epoxide or chlorinated epoxide;
(d) from 0.1 to 3% by weight of at least one C13 nitroalkane; and
(e) from 0.001 to 1% by weight of at least one aliphatic, cyclic or heterocyclic C4 10 amine of a basic nature.
2. A process for the stabilization of 1,1,1-trichloroethane, comprising incorporating in it:
(a) from 0.5 to 3.5% by weight of tertiary butyl alcohol;
(b) from 0.3 to 3% by weight of at least one of 2-methylbut-3-yn-2-ol and trioxan;
(c) from 0.2 to 3% by weight of at least one C38 epoxide or chlorinated epoxide;
(d) from 0.1 to 3% by weight of at least one Con 3 nitroalkane; and
(e) from 0.005 to 0.1% by weight of at least one aliphatic, cyclic or heterocyclic C4 10 amine of a basic nature.
3. A process according to claim 1 or 2 in which, when tertiary butyl alcohol and 2-methylbut-3-yn-2-ol are associated, the binary mixture comprises from 1 to 99% by weight of tertiary butyl alcohol and from 99 to 1% by weight of 2-methylbut-3-yn-2-ol.
4. A process according to claim 3 in which the binary mixture comprises from 25 to 80% by weight of tertiary butyl alcohol and from 75 to 20% by weight of 2-methylbut-3-yn-2-ol.
5. A process according to any one of claims 1 to 4 in which the epoxide is 1,2-butylene oxide.
6. A process according to any one of claims 1 to 4 in which the epoxide is epichlorohydrin, glycidol or its primary, secondary or tertiary methyl, ethyl, propyl, isopropyl, alyl or butyl ether, 1,2-propylene oxide, styrene oxide or cyclohexene oxide.
7. A process according to any one of claims 1 to 6 in which the compound selected in (b) is trioxan alone, in amounts of from 0.5 to 3% by weight.
8. A process according to any one of claims 1 to 7 in which the amine is diisopropylamine,
N-methyl-morpholine or pyrrolidine.
9. A process according to any one of claims 1 to 8 in which the stabilization action is strengthened by the addition of, as an anti-oxidant, at least one phenol or nitrogeneous heterocycle having from 1 to 2 nitrogen atoms and from 3 to 5 carbon atoms with possibly an oxygen atom in the ring in an amount of up to 1% by weight with respect to the 1,1,1 -trichloroethane.
10. A process according to claim 10 in which the antioxidant is N-methylpyrrole.
11. A process according to claim 9 ar 10 in which the amount of antioxidant is from 0.001 to 0.1% by weight with respect to the 1,1,1 -trichloroethane.
12. A stabilized composition based on 1,1,1-trichloroethane, containing, as essential stabilizing agents:
(a) from 0.1 to 5% by weight of tertiary butyl alcohol;
(b) from 0.1 to 5% by weight of at least one of 2-methylbut-3-yn-2-ol and trioxan;
(c) from 0.1 to 5% by weight of at least one C38 epoxide or chlorinated epoxide;
(d) from 0.1 to 3% by weight of at least one C1.3 nitroalkane;
(e) from 0.001 to 1% by weight of at least one aliphatic, cyclic or heterocyclic C4 10 amine of a basic nature; and
(f) as antioxidant, from 0 to 1% by weight of at least one phenol and/or nitrogenous heterocycle having from 3 to 5 carbon atoms, from 1 to 2 nitrogen atoms and possibly an oxygen atom in the ring.
13. A composition according to claim 12 containing, as stabilizing agents;
(a) from 0.5 to 3.5% by weight of tertiary butyl alcohol;
(b) from 0.3 to 3% by weight of at least one of 2-methylbut-3-yn-2-ol and trioxan;
(c) from 0.2 to 3% by weight of at least one C3-8 epoxide or chlorinated epoxide;
(d) from 0.1 to 3% by weight of at least one C13 nitroalkane containing from 1 to 3 carbon atoms;
(e) from 0.005 to 0.1% by weight of at least one C4 10 aliphatic, cyclic or heterocyclic amine of basic nature; and
(f) an antioxidant, from 0.001 to 1.0% by weight of at least one phenol and/or nitrogenous heterocycle having from 3 to 5 carbon atoms, from 1 to 2 nitrogen atoms and possibly an oxygen atom in the ring.
14. A composition according to claim 12 or 13 containing a binary mixture of tertiary butyl alcohol and 2-methylbut-3-yn-2-ol comprising from 25 to 80% by weight of tertiary butyl alcohol for from 75 to 20% by weight of 2-methylbut-3-yn-2-ol.
15. A composition according to claim 12, 13 or 14 in which the epoxide is 1,2-butylene oxide.
16. A composition according to claim 12, 13 or 14 in which the epoxide is epichlorohydrin, glycidol or its primary, secondary or tertiary methyl, ethyl, propyl, isopropyl, allyl or butyl ether, 1,2-propylene oxide, styrene oxide or cyclohexene oxide.
17. A composition according to any one of claims 12 to 16 in which the amount of trioxan is from 0.5 to 3% and it is free from 2-methylbut-3-yn-2-ol.
18. A composition according to any one of claims 12 to 17 in which the amine is diisopropylamine,
N-methyl-morpholine or pyrrolidine.
19. A composition according to any one of claims 12 to 18 in which the anti-oxidizing agent is
N-methylpyrrole.
20. A composition according to claim 12, substantially as hereinbefore described in any one of the
Examples.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7819591A FR2437392A1 (en) | 1978-06-30 | 1978-06-30 | STABILIZATION OF TRICHLORO-1,1,1 ETHANE |
Publications (2)
Publication Number | Publication Date |
---|---|
GB2024243A true GB2024243A (en) | 1980-01-09 |
GB2024243B GB2024243B (en) | 1983-03-23 |
Family
ID=9210180
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7922751A Expired GB2024243B (en) | 1978-06-30 | 1979-06-29 | Stabilisation of 1,1,1-trichloroethane |
Country Status (14)
Country | Link |
---|---|
JP (1) | JPS595563B2 (en) |
AT (1) | AT370712B (en) |
BE (1) | BE877385A (en) |
CA (1) | CA1133949A (en) |
CH (1) | CH640492A5 (en) |
DE (1) | DE2926000C3 (en) |
DK (1) | DK275979A (en) |
ES (1) | ES482050A0 (en) |
FR (1) | FR2437392A1 (en) |
GB (1) | GB2024243B (en) |
GR (1) | GR69971B (en) |
IT (1) | IT1119785B (en) |
NL (1) | NL187851C (en) |
SE (1) | SE445826B (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4356038A (en) | 1979-07-25 | 1982-10-26 | Imperial Chemical Industries Limited | Stabilization of chlorinated aliphatic hydrocarbons and use of stabilized composition in cleaning articles |
EP0091708A1 (en) * | 1982-04-09 | 1983-10-19 | Shell Internationale Researchmaatschappij B.V. | Stabilized 1,1,1-trichlorethane |
US4973420A (en) * | 1989-05-04 | 1990-11-27 | Hoechst Celanese Corporation | Stripper composition for removal of protective coatings |
US4992604A (en) * | 1989-07-24 | 1991-02-12 | Ppg Industries, Inc. | Stabilized 1,1,1-trichloroethane compositions |
WO2002036531A2 (en) * | 2000-11-03 | 2002-05-10 | Dow Global Technologies Inc. | Stabilizer and solvent compositions |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5811407B2 (en) * | 1979-12-24 | 1983-03-02 | 旭化成株式会社 | Stabilized 1,1,1-trichloroethane composition |
CA1275097A (en) | 1984-10-02 | 1990-10-09 | Fujio Nohara | Pyridyloxy derivatives |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1444410A (en) * | 1964-07-20 | 1966-07-01 | Pittsburgh Plate Glass Co | Methyl chloroform compositions |
FR1567940A (en) * | 1967-11-17 | 1969-05-23 | Pechiney Saint Gobain | |
CA943141A (en) * | 1970-01-22 | 1974-03-05 | Diamond Shamrock Corporation | Stabilization of methyl chloroform |
JPS5236741B2 (en) * | 1973-08-01 | 1977-09-17 |
-
1978
- 1978-06-30 FR FR7819591A patent/FR2437392A1/en active Granted
-
1979
- 1979-06-27 DE DE2926000A patent/DE2926000C3/en not_active Expired
- 1979-06-27 SE SE7905627A patent/SE445826B/en not_active IP Right Cessation
- 1979-06-28 IT IT49564/79A patent/IT1119785B/en active
- 1979-06-28 GR GR59469A patent/GR69971B/el unknown
- 1979-06-29 BE BE0/196060A patent/BE877385A/en not_active IP Right Cessation
- 1979-06-29 AT AT0457479A patent/AT370712B/en not_active IP Right Cessation
- 1979-06-29 CH CH611079A patent/CH640492A5/en not_active IP Right Cessation
- 1979-06-29 NL NLAANVRAGE7905097,A patent/NL187851C/en not_active IP Right Cessation
- 1979-06-29 DK DK275979A patent/DK275979A/en not_active Application Discontinuation
- 1979-06-29 CA CA330,825A patent/CA1133949A/en not_active Expired
- 1979-06-29 GB GB7922751A patent/GB2024243B/en not_active Expired
- 1979-06-29 JP JP54081594A patent/JPS595563B2/en not_active Expired
- 1979-06-29 ES ES482050A patent/ES482050A0/en active Granted
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4356038A (en) | 1979-07-25 | 1982-10-26 | Imperial Chemical Industries Limited | Stabilization of chlorinated aliphatic hydrocarbons and use of stabilized composition in cleaning articles |
EP0091708A1 (en) * | 1982-04-09 | 1983-10-19 | Shell Internationale Researchmaatschappij B.V. | Stabilized 1,1,1-trichlorethane |
US4973420A (en) * | 1989-05-04 | 1990-11-27 | Hoechst Celanese Corporation | Stripper composition for removal of protective coatings |
US4992604A (en) * | 1989-07-24 | 1991-02-12 | Ppg Industries, Inc. | Stabilized 1,1,1-trichloroethane compositions |
WO2002036531A2 (en) * | 2000-11-03 | 2002-05-10 | Dow Global Technologies Inc. | Stabilizer and solvent compositions |
WO2002036531A3 (en) * | 2000-11-03 | 2002-07-25 | Dow Global Technologies Inc | Stabilizer and solvent compositions |
Also Published As
Publication number | Publication date |
---|---|
ES8102079A1 (en) | 1980-12-16 |
DE2926000B2 (en) | 1980-08-07 |
IT7949564A0 (en) | 1979-06-28 |
CA1133949A (en) | 1982-10-19 |
NL7905097A (en) | 1980-01-03 |
DK275979A (en) | 1979-12-31 |
DE2926000C3 (en) | 1981-06-04 |
GB2024243B (en) | 1983-03-23 |
CH640492A5 (en) | 1984-01-13 |
FR2437392A1 (en) | 1980-04-25 |
SE445826B (en) | 1986-07-21 |
BE877385A (en) | 1979-12-31 |
JPS595563B2 (en) | 1984-02-06 |
ATA457479A (en) | 1982-09-15 |
GR69971B (en) | 1982-07-22 |
DE2926000A1 (en) | 1980-01-03 |
AT370712B (en) | 1983-04-25 |
JPS5511583A (en) | 1980-01-26 |
NL187851C (en) | 1992-02-03 |
FR2437392B1 (en) | 1983-01-28 |
IT1119785B (en) | 1986-03-10 |
ES482050A0 (en) | 1980-12-16 |
SE7905627L (en) | 1979-12-31 |
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