TWI373522B - Stabilized propyl bromide compositions - Google Patents
Stabilized propyl bromide compositions Download PDFInfo
- Publication number
- TWI373522B TWI373522B TW094138228A TW94138228A TWI373522B TW I373522 B TWI373522 B TW I373522B TW 094138228 A TW094138228 A TW 094138228A TW 94138228 A TW94138228 A TW 94138228A TW I373522 B TWI373522 B TW I373522B
- Authority
- TW
- Taiwan
- Prior art keywords
- composition
- carbon atoms
- alkyl group
- ppm
- range
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 105
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 title claims description 25
- 150000002989 phenols Chemical class 0.000 claims description 49
- 239000002904 solvent Substances 0.000 claims description 32
- 239000003381 stabilizer Substances 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 20
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 20
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 16
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 14
- 230000000996 additive effect Effects 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 7
- 238000004140 cleaning Methods 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims 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 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical class COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 150000002601 lanthanoid compounds Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 239000000758 substrate Substances 0.000 claims 2
- JXZABYGWFNGNLB-UHFFFAOYSA-N 4-methoxybenzene-1,2-diol Chemical group COC1=CC=C(O)C(O)=C1 JXZABYGWFNGNLB-UHFFFAOYSA-N 0.000 claims 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- 238000013112 stability test Methods 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
- 239000004615 ingredient Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 10
- 238000004817 gas chromatography Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 150000002924 oxiranes Chemical class 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical compound CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 description 5
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 5
- XFNJYAKDBJUJAJ-UHFFFAOYSA-N 1,2-dibromopropane Chemical compound CC(Br)CBr XFNJYAKDBJUJAJ-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- -1 diethyl-6-t-butylphenylhydrazine Chemical compound 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229960003742 phenol Drugs 0.000 description 4
- WIXDSJRJFDWTNY-UHFFFAOYSA-N 1,3-ditert-butyl-5-methylbenzene Chemical compound CC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1 WIXDSJRJFDWTNY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 238000000844 transformation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- MBGGFXOXUIDRJD-UHFFFAOYSA-N 4-Butoxyphenol Chemical compound CCCCOC1=CC=C(O)C=C1 MBGGFXOXUIDRJD-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical class OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 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
- 229920000642 polymer Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- PXSROARFGKQZQG-UHFFFAOYSA-N (2,6-ditert-butyl-4-methylphenyl)hydrazine Chemical compound C(C)(C)(C)C1=C(C(=CC(=C1)C)C(C)(C)C)NN PXSROARFGKQZQG-UHFFFAOYSA-N 0.000 description 1
- RSHAXJWPAMYMPL-UHFFFAOYSA-N (2,6-ditert-butylphenyl)hydrazine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1NN RSHAXJWPAMYMPL-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical group CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- URHGABHMSVPNGF-UHFFFAOYSA-N 1-butyl-1-(4-methylphenyl)hydrazine Chemical compound CCCCN(N)C1=CC=C(C)C=C1 URHGABHMSVPNGF-UHFFFAOYSA-N 0.000 description 1
- XMDQJXIEKHMDMG-UHFFFAOYSA-N 1-methyl-6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21C XMDQJXIEKHMDMG-UHFFFAOYSA-N 0.000 description 1
- WGCRBZNYMUSMEV-UHFFFAOYSA-N 2,3-dihydroxypropyl pentanoate Chemical compound CCCCC(=O)OCC(O)CO WGCRBZNYMUSMEV-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 1
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
- QAWZBYZTGPATNQ-UHFFFAOYSA-N 2-ethyl-6-(2-methylbutan-2-yl)phenol Chemical compound CCC1=CC=CC(C(C)(C)CC)=C1O QAWZBYZTGPATNQ-UHFFFAOYSA-N 0.000 description 1
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- MDURQPNBPHBIFN-UHFFFAOYSA-N 2-pentoxyphenol Chemical compound CCCCCOC1=CC=CC=C1O MDURQPNBPHBIFN-UHFFFAOYSA-N 0.000 description 1
- NMOFYYYCFRVWBK-UHFFFAOYSA-N 2-pentyloxirane Chemical compound CCCCCC1CO1 NMOFYYYCFRVWBK-UHFFFAOYSA-N 0.000 description 1
- SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical compound CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- APIQWHVRWQYLFW-UHFFFAOYSA-N 2-tert-butyl-6-ethylphenol Chemical compound CCC1=CC=CC(C(C)(C)C)=C1O APIQWHVRWQYLFW-UHFFFAOYSA-N 0.000 description 1
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 1
- XGHAAJWWNQHCQI-UHFFFAOYSA-N 3-(2-methylpropoxy)propane-1,2-diol Chemical compound CC(C)COCC(O)CO XGHAAJWWNQHCQI-UHFFFAOYSA-N 0.000 description 1
- PSJBSUHYCGQTHZ-UHFFFAOYSA-N 3-Methoxy-1,2-propanediol Chemical compound COCC(O)CO PSJBSUHYCGQTHZ-UHFFFAOYSA-N 0.000 description 1
- ZTGQZSKPSJUEBU-UHFFFAOYSA-N 3-bromopropan-1-amine Chemical compound NCCCBr ZTGQZSKPSJUEBU-UHFFFAOYSA-N 0.000 description 1
- UNFGWQUDDQBNLD-UHFFFAOYSA-N 3-propan-2-yloxypropane-1,2-diol Chemical compound CC(C)OCC(O)CO UNFGWQUDDQBNLD-UHFFFAOYSA-N 0.000 description 1
- HFLGBNBLMBSXEM-UHFFFAOYSA-N 4-Ethyl-1,2-benzenediol Chemical compound CCC1=CC=C(O)C(O)=C1 HFLGBNBLMBSXEM-UHFFFAOYSA-N 0.000 description 1
- CIICLJLSRUHUBY-UHFFFAOYSA-N 4-[(2-methylpropan-2-yl)oxy]phenol Chemical compound CC(C)(C)OC1=CC=C(O)C=C1 CIICLJLSRUHUBY-UHFFFAOYSA-N 0.000 description 1
- QEYQMWSESURNPP-UHFFFAOYSA-N 4-propan-2-yloxyphenol Chemical compound CC(C)OC1=CC=C(O)C=C1 QEYQMWSESURNPP-UHFFFAOYSA-N 0.000 description 1
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000239226 Scorpiones Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000246358 Thymus Species 0.000 description 1
- 235000007303 Thymus vulgaris Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- RIEABXYBQSLTFR-UHFFFAOYSA-N monobutyrin Chemical compound CCCC(=O)OCC(O)CO RIEABXYBQSLTFR-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- JTXAHXNXKFGXIT-UHFFFAOYSA-N propane;prop-1-ene Chemical compound CCC.CC=C JTXAHXNXKFGXIT-UHFFFAOYSA-N 0.000 description 1
- 229960004134 propofol Drugs 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000011076 safety test Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- LVBXEMGDVWVTGY-UHFFFAOYSA-N trans-2-octenal Natural products CCCCCC=CC=O LVBXEMGDVWVTGY-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 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
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5018—Halogenated solvents
-
- 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
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/26—Organic compounds containing oxygen
- C11D7/261—Alcohols; Phenols
-
- 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
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/26—Organic compounds containing oxygen
- C11D7/261—Alcohols; Phenols
- C11D7/262—Alcohols; Phenols fatty or with at least 8 carbon atoms in the alkyl or alkenyl chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
- Manufacturing Of Printed Wiring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2004/037033 WO2006052241A1 (en) | 2004-11-05 | 2004-11-05 | Stabilized propyl bromide compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200624409A TW200624409A (en) | 2006-07-16 |
| TWI373522B true TWI373522B (en) | 2012-10-01 |
Family
ID=34959599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094138228A TWI373522B (en) | 2004-11-05 | 2005-11-01 | Stabilized propyl bromide compositions |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8129325B2 (enExample) |
| EP (1) | EP1812543B2 (enExample) |
| JP (1) | JP5308672B2 (enExample) |
| CN (1) | CN101052704B (enExample) |
| AR (1) | AR051474A1 (enExample) |
| AT (1) | ATE465231T1 (enExample) |
| BR (1) | BRPI0419128B1 (enExample) |
| DE (1) | DE602004026790D1 (enExample) |
| TW (1) | TWI373522B (enExample) |
| WO (1) | WO2006052241A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101171220B (zh) | 2005-05-03 | 2012-06-06 | 雅宝公司 | 低酸度的1-溴丙烷 |
| EP2061739A1 (en) * | 2006-08-30 | 2009-05-27 | Albermarle Corporation | Propyl bromide compositions |
| CN101367705B (zh) * | 2008-07-23 | 2012-05-02 | 天津长芦海晶集团有限公司 | 提高1-溴丙烷稳定性的方法 |
| CN103627371A (zh) * | 2012-08-23 | 2014-03-12 | 中化蓝天集团有限公司 | 适用于hfc-161和含hfc-161混合工质的稳定剂组合物 |
| CN103604899B (zh) * | 2013-11-13 | 2014-10-22 | 广州广电计量检测股份有限公司 | 皮革、纺织品中溴代正丙烷的检测方法 |
| US9260595B1 (en) * | 2014-08-26 | 2016-02-16 | Zyp Coatings, Inc. | N-propyl bromide solvent systems |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220607A (en) | 1978-03-17 | 1980-09-02 | Wacker-Chemie Gmbh | Stabilized perchloroethylene |
| FR2429767A1 (fr) | 1978-06-30 | 1980-01-25 | Rhone Poulenc Ind | Procede de stabilisation du trichloro-1,1,1 ethane |
| US4385192A (en) | 1978-07-05 | 1983-05-24 | Amvac Chemical Corporation | Process for manufacturing DBCP |
| JPH01292095A (ja) | 1988-05-19 | 1989-11-24 | Daikin Ind Ltd | 含フッ素油の安定化法 |
| JP2576933B2 (ja) | 1993-01-25 | 1997-01-29 | ディップソール株式会社 | 洗浄用溶剤組成物 |
| US5403507A (en) | 1993-08-20 | 1995-04-04 | Advanced Research Technologies | Vapor cleaning of metallic and electrical materials utilizing environmentally safe solvent materials |
| JPH0867643A (ja) | 1994-08-30 | 1996-03-12 | Toagosei Co Ltd | 安定化されたブロモプロパン組成物 |
| US5858953A (en) | 1995-04-12 | 1999-01-12 | Tosoh Corporation | Stabilized 1-bromopropane composition |
| JP3582404B2 (ja) * | 1995-04-12 | 2004-10-27 | 東ソー株式会社 | 安定化された１−ブロモプロパン組成物 |
| JP2956578B2 (ja) * | 1995-04-12 | 1999-10-04 | 東ソー株式会社 | 安定化された１−ブロモプロパン組成物 |
| US5690862A (en) | 1995-11-01 | 1997-11-25 | Albemarle Corporation | No flash point solvent system containing normal propyl bromide |
| US5707954A (en) * | 1996-03-01 | 1998-01-13 | Albemarle Corporation | Stabilized brominated alkane solvent |
| JP3478665B2 (ja) | 1996-05-16 | 2003-12-15 | ディップソール株式会社 | 洗浄用臭素系溶剤組成物 |
| JPH1046197A (ja) | 1996-08-02 | 1998-02-17 | Tosoh Corp | 非引火性洗浄剤組成物 |
| IL131408A0 (en) | 1997-02-19 | 2001-01-28 | Great Lakes Chemical Corp | Process for the manufacture of tetrabromobisphenol-a with co-production of n-propyl bromide |
| US6048471A (en) | 1997-07-18 | 2000-04-11 | Richard G. Henry | Zero volatile organic compound compositions based upon organic solvents which are negligibly reactive with hydroxyl radical and do not contribute appreciably to the formation of ground based ozone |
| WO1998050517A1 (en) * | 1997-05-02 | 1998-11-12 | Advanced Chemical Design | Environmentally-safe solvent compositions utilizing 1-bromopropane that are stabilized, non-flammable, and have desired solvency characteristics |
| US20020151447A1 (en) | 1997-07-18 | 2002-10-17 | Polymer Solvents, Inc. | Reduced toxicity 1-bromopropane cleaning agent production process |
| US5792277A (en) | 1997-07-23 | 1998-08-11 | Albemarle Corporation | N-propyl bromide based cleaning solvent and ionic residue removal process |
| US6350395B1 (en) | 1997-12-18 | 2002-02-26 | The Dow Chemical Company | Stabilizer composition |
| JPH11293287A (ja) | 1998-04-07 | 1999-10-26 | Tosoh Corp | 水切り溶剤組成物 |
| US6071872A (en) | 1998-06-10 | 2000-06-06 | Arnco Corporation | Cable cleaning solution comprising a brominated hydrocarbon and an ester |
| US6103684A (en) | 1998-06-25 | 2000-08-15 | Alliedsignal Inc. | Compositions of 1-bromopropane and an organic solvent |
| US6165284A (en) † | 1998-06-25 | 2000-12-26 | Albemarle Corporation | Method for inhibiting tarnish formation during the cleaning of silver surfaces with ether stabilized, N-propyl bromide-based solvent systems |
| US6258770B1 (en) | 1998-09-11 | 2001-07-10 | Albemarle Corporation | Compositions for surface cleaning in aerosol applications |
| US6660701B1 (en) | 2000-10-23 | 2003-12-09 | Polysystems Usa, Inc. | Stabilized solvent system for cleaning and drying |
-
2004
- 2004-11-05 CN CN2004800443521A patent/CN101052704B/zh not_active Expired - Fee Related
- 2004-11-05 DE DE602004026790T patent/DE602004026790D1/de not_active Expired - Lifetime
- 2004-11-05 AT AT04810451T patent/ATE465231T1/de not_active IP Right Cessation
- 2004-11-05 JP JP2007538879A patent/JP5308672B2/ja not_active Expired - Fee Related
- 2004-11-05 EP EP04810451.7A patent/EP1812543B2/en not_active Expired - Lifetime
- 2004-11-05 US US11/577,899 patent/US8129325B2/en not_active Expired - Fee Related
- 2004-11-05 BR BRPI0419128A patent/BRPI0419128B1/pt not_active IP Right Cessation
- 2004-11-05 WO PCT/US2004/037033 patent/WO2006052241A1/en not_active Ceased
-
2005
- 2005-11-01 TW TW094138228A patent/TWI373522B/zh not_active IP Right Cessation
- 2005-11-02 AR ARP050104587A patent/AR051474A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AR051474A1 (es) | 2007-01-17 |
| EP1812543B2 (en) | 2014-03-05 |
| US20090253608A1 (en) | 2009-10-08 |
| CN101052704A (zh) | 2007-10-10 |
| JP5308672B2 (ja) | 2013-10-09 |
| BRPI0419128A (pt) | 2007-12-11 |
| EP1812543A1 (en) | 2007-08-01 |
| DE602004026790D1 (de) | 2010-06-02 |
| EP1812543B1 (en) | 2010-04-21 |
| WO2006052241A1 (en) | 2006-05-18 |
| CN101052704B (zh) | 2011-03-23 |
| TW200624409A (en) | 2006-07-16 |
| JP2008519093A (ja) | 2008-06-05 |
| BRPI0419128B1 (pt) | 2015-10-13 |
| ATE465231T1 (de) | 2010-05-15 |
| US8129325B2 (en) | 2012-03-06 |
| HK1113938A1 (zh) | 2008-10-17 |
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| Date | Code | Title | Description |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |