JPS6046041B2 - 希釈された塩酸水からガス状の塩化水素を製造する方法 - Google Patents
希釈された塩酸水からガス状の塩化水素を製造する方法Info
- Publication number
- JPS6046041B2 JPS6046041B2 JP52088892A JP8889277A JPS6046041B2 JP S6046041 B2 JPS6046041 B2 JP S6046041B2 JP 52088892 A JP52088892 A JP 52088892A JP 8889277 A JP8889277 A JP 8889277A JP S6046041 B2 JPS6046041 B2 JP S6046041B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen chloride
- amine
- water
- solvent
- hydrochloric acid
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims description 202
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 title claims description 157
- 229910000041 hydrogen chloride Inorganic materials 0.000 title claims description 157
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 51
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001412 amines Chemical class 0.000 claims description 69
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 41
- 239000002904 solvent Substances 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 27
- 238000000605 extraction Methods 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 239000012044 organic layer Substances 0.000 claims description 18
- 239000000284 extract Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 238000010992 reflux Methods 0.000 claims description 16
- 238000009835 boiling Methods 0.000 claims description 14
- 238000004821 distillation Methods 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- -1 chloro- Chemical compound 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- 150000003337 secondary aryl alkyl amines Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 150000003997 cyclic ketones Chemical class 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 230000002051 biphasic effect Effects 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 150000001983 dialkylethers Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 238000011176 pooling Methods 0.000 claims 1
- 239000010410 layer Substances 0.000 description 44
- 239000000243 solution Substances 0.000 description 26
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
- 239000008096 xylene Substances 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 238000000926 separation method Methods 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000010494 dissociation reaction Methods 0.000 description 9
- 230000005593 dissociations Effects 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000007788 liquid Substances 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- FZPXKEPZZOEPGX-UHFFFAOYSA-N n,n-dibutylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1 FZPXKEPZZOEPGX-UHFFFAOYSA-N 0.000 description 4
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- GCULWAWIZUGXTO-UHFFFAOYSA-N n-octylaniline Chemical compound CCCCCCCCNC1=CC=CC=C1 GCULWAWIZUGXTO-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- XJEPUDKDCKLTSL-UHFFFAOYSA-N n,n-didodecylaniline Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)C1=CC=CC=C1 XJEPUDKDCKLTSL-UHFFFAOYSA-N 0.000 description 2
- PTRSTXBRQVXIEW-UHFFFAOYSA-N n,n-dioctylaniline Chemical compound CCCCCCCCN(CCCCCCCC)C1=CC=CC=C1 PTRSTXBRQVXIEW-UHFFFAOYSA-N 0.000 description 2
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- XGQJZNCFDLXSIJ-UHFFFAOYSA-N pentadecanal Chemical class CCCCCCCCCCCCCCC=O XGQJZNCFDLXSIJ-UHFFFAOYSA-N 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- 150000000094 1,4-dioxanes Chemical class 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical class CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 1
- UPLLOZNXRIMQKE-UHFFFAOYSA-N 13-methyltetradecan-1-amine Chemical class CC(C)CCCCCCCCCCCCN UPLLOZNXRIMQKE-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- QHTJSSMHBLGUHV-UHFFFAOYSA-N 2-methylbutan-2-ylbenzene Chemical compound CCC(C)(C)C1=CC=CC=C1 QHTJSSMHBLGUHV-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ICBJCVRQDSQPGI-UHFFFAOYSA-N Methyl hexyl ether Chemical compound CCCCCCOC ICBJCVRQDSQPGI-UHFFFAOYSA-N 0.000 description 1
- YJLYANLCNIKXMG-UHFFFAOYSA-N N-Methyldioctylamine Chemical compound CCCCCCCCN(C)CCCCCCCC YJLYANLCNIKXMG-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- MMCPOSDMTGQNKG-UJZMCJRSSA-N aniline;hydrochloride Chemical compound Cl.N[14C]1=[14CH][14CH]=[14CH][14CH]=[14CH]1 MMCPOSDMTGQNKG-UJZMCJRSSA-N 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PZTVYZVWAHUIMY-UHFFFAOYSA-N n,n,13-trimethyltetradecan-1-amine Chemical class CC(C)CCCCCCCCCCCCN(C)C PZTVYZVWAHUIMY-UHFFFAOYSA-N 0.000 description 1
- CXHKRLBPORFDTI-UHFFFAOYSA-N n,n-bis(2-methylpropyl)dodecan-1-amine Chemical compound CCCCCCCCCCCCN(CC(C)C)CC(C)C CXHKRLBPORFDTI-UHFFFAOYSA-N 0.000 description 1
- RMORGQAUMQJGQH-UHFFFAOYSA-N n,n-bis(6-methylheptyl)cyclohexanamine Chemical compound CC(C)CCCCCN(CCCCCC(C)C)C1CCCCC1 RMORGQAUMQJGQH-UHFFFAOYSA-N 0.000 description 1
- UCTLSGRLXPPMGW-UHFFFAOYSA-N n,n-di(propan-2-yl)dodecan-1-amine Chemical compound CCCCCCCCCCCCN(C(C)C)C(C)C UCTLSGRLXPPMGW-UHFFFAOYSA-N 0.000 description 1
- FTBKGTWNWSTGAY-UHFFFAOYSA-N n,n-dibutyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(CCCC)CCCC FTBKGTWNWSTGAY-UHFFFAOYSA-N 0.000 description 1
- RBVICEYRUIXMCB-UHFFFAOYSA-N n,n-diethyl-2-hexylaniline Chemical compound CCCCCCC1=CC=CC=C1N(CC)CC RBVICEYRUIXMCB-UHFFFAOYSA-N 0.000 description 1
- CLZGJKHEVKJLLS-UHFFFAOYSA-N n,n-diheptylheptan-1-amine Chemical compound CCCCCCCN(CCCCCCC)CCCCCCC CLZGJKHEVKJLLS-UHFFFAOYSA-N 0.000 description 1
- DGYRVXQIGUEFFK-UHFFFAOYSA-N n,n-dihexylaniline Chemical compound CCCCCCN(CCCCCC)C1=CC=CC=C1 DGYRVXQIGUEFFK-UHFFFAOYSA-N 0.000 description 1
- OSTOOHZZEAYMEQ-UHFFFAOYSA-N n-(11-methyldodecyl)aniline Chemical compound CC(C)CCCCCCCCCCNC1=CC=CC=C1 OSTOOHZZEAYMEQ-UHFFFAOYSA-N 0.000 description 1
- AJWFHRZHFZIUEN-UHFFFAOYSA-N n-(13-methyltetradecyl)aniline Chemical compound CC(C)CCCCCCCCCCCCNC1=CC=CC=C1 AJWFHRZHFZIUEN-UHFFFAOYSA-N 0.000 description 1
- YGNSGUIRANPPSW-UHFFFAOYSA-N n-decyl-n-ethyldecan-1-amine Chemical compound CCCCCCCCCCN(CC)CCCCCCCCCC YGNSGUIRANPPSW-UHFFFAOYSA-N 0.000 description 1
- OMJXLMIOYHFITL-UHFFFAOYSA-N n-dodecyl-n-hexylaniline Chemical compound CCCCCCCCCCCCN(CCCCCC)C1=CC=CC=C1 OMJXLMIOYHFITL-UHFFFAOYSA-N 0.000 description 1
- GOJIVVWJAXAPGS-UHFFFAOYSA-N n-dodecyl-n-methylaniline Chemical compound CCCCCCCCCCCCN(C)C1=CC=CC=C1 GOJIVVWJAXAPGS-UHFFFAOYSA-N 0.000 description 1
- UWHRNIXHZAWBMF-UHFFFAOYSA-N n-dodecyl-n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)CCCCCCCCCCCC UWHRNIXHZAWBMF-UHFFFAOYSA-N 0.000 description 1
- LQKYCMRSWKQVBQ-UHFFFAOYSA-N n-dodecylaniline Chemical compound CCCCCCCCCCCCNC1=CC=CC=C1 LQKYCMRSWKQVBQ-UHFFFAOYSA-N 0.000 description 1
- XDCINBSGHHNWGY-UHFFFAOYSA-N n-ethyl-n-hexylaniline Chemical compound CCCCCCN(CC)C1=CC=CC=C1 XDCINBSGHHNWGY-UHFFFAOYSA-N 0.000 description 1
- LWIPGCTWFZCIKX-UHFFFAOYSA-N n-ethyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCC LWIPGCTWFZCIKX-UHFFFAOYSA-N 0.000 description 1
- DXEMBEKDWHKDEV-UHFFFAOYSA-N n-methyl-n-(2-methylpropyl)dodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)CC(C)C DXEMBEKDWHKDEV-UHFFFAOYSA-N 0.000 description 1
- UEKWTIYPDJLSKK-UHFFFAOYSA-N n-octadecylaniline Chemical compound CCCCCCCCCCCCCCCCCCNC1=CC=CC=C1 UEKWTIYPDJLSKK-UHFFFAOYSA-N 0.000 description 1
- MYDZALGHMPTXMD-UHFFFAOYSA-N n-octylnaphthalen-1-amine Chemical compound C1=CC=C2C(NCCCCCCCC)=CC=CC2=C1 MYDZALGHMPTXMD-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/01—Chlorine; Hydrogen chloride
- C01B7/07—Purification ; Separation
- C01B7/0706—Purification ; Separation of hydrogen chloride
- C01B7/0731—Purification ; Separation of hydrogen chloride by extraction
- C01B7/0737—Purification ; Separation of hydrogen chloride by extraction hydrogen chloride being extracted
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0492—Applications, solvents used
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2633640A DE2633640C3 (de) | 1976-07-27 | 1976-07-27 | Verfahren zur Gewinnung von gasförmigem Chlorwasserstoff aus verdünnter wäBriger Salzsäure |
| DE2633640.3 | 1976-07-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5315291A JPS5315291A (en) | 1978-02-10 |
| JPS6046041B2 true JPS6046041B2 (ja) | 1985-10-14 |
Family
ID=5984015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52088892A Expired JPS6046041B2 (ja) | 1976-07-27 | 1977-07-26 | 希釈された塩酸水からガス状の塩化水素を製造する方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4115530A (OSRAM) |
| JP (1) | JPS6046041B2 (OSRAM) |
| BE (1) | BE857171A (OSRAM) |
| DE (1) | DE2633640C3 (OSRAM) |
| FR (1) | FR2391950A1 (OSRAM) |
| GB (1) | GB1581770A (OSRAM) |
| IT (1) | IT1079361B (OSRAM) |
| NL (1) | NL7708283A (OSRAM) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2921916C2 (de) * | 1979-05-30 | 1982-05-27 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Gewinnung von gasförmigem Chlorwasserstoff aus verdünnter wäßriger Salzsäure |
| DE2805933C2 (de) * | 1978-02-13 | 1980-04-30 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Abspaltung von Chlorwasserstoff aus Lösungen von Aminhydrochloriden |
| DE2834252C3 (de) * | 1978-08-04 | 1981-07-30 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Gewinnung von gasförmigem Chlorwasserstoff |
| DE2836580C3 (de) * | 1978-08-21 | 1981-11-05 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Trennung von Chlorwasserstoff und Bromwasserstoff |
| US4259309A (en) * | 1979-08-08 | 1981-03-31 | Chemische Werke Huls Ag | Method for obtaining gaseous hydrogen chloride from dilute aqueous hydrochloric acid |
| EP0027193B1 (de) * | 1979-10-06 | 1982-12-15 | Chemische Werke Hüls Ag | Verfahren zur Herstellung von Natriumhydrogencarbonat und Chlorwasserstoff |
| DE3031213A1 (de) * | 1979-10-06 | 1982-04-01 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von natriumhydrogencarbonat und chlorwasserstoff |
| DE2940555A1 (de) * | 1979-10-06 | 1981-04-02 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von ammoniak und chlorwasserstoff aus ammoniumchlorid |
| US4640831A (en) * | 1984-12-18 | 1987-02-03 | The Dow Chemical Company | Method for recovering protic acids using reversible bases |
| US4582929A (en) * | 1984-12-24 | 1986-04-15 | The Dow Chemical Company | Method of recovering halide values from carbonylation reaction mixtures |
| US4608245A (en) * | 1985-10-17 | 1986-08-26 | Gaddy James L | Method of separation of sugars and concentrated sulfuric acid |
| US4882134A (en) * | 1987-04-10 | 1989-11-21 | Imc Fertilizer, Inc. | Recovery of hydrogen fluoride from an aqueous solution containing ammonium fluoride and hydrogen fluoride |
| US4980031A (en) * | 1989-08-02 | 1990-12-25 | E. I. Du Pont De Nemours And Company | Solvent recovery |
| JP2001192202A (ja) * | 1999-03-31 | 2001-07-17 | Toyo Eng Corp | 無水塩化水素の製造方法 |
| BRPI0906901A2 (pt) * | 2008-04-08 | 2015-07-21 | Hcl Cleantech Ltd | Processo para a recuperação de hcl de uma solução diluída do mesmo, processo para a produção de carboidratos e composição. |
| EP2321218A1 (en) * | 2008-09-02 | 2011-05-18 | Hcl Cleantech Ltd. | A process for the production of hcl gas from chloride salts and for the production of carbohydrates |
| IL195646A0 (en) * | 2008-12-02 | 2009-09-01 | Aharon Eyal | A process for the recovery of hydrochloric acid |
| EP3401410B1 (en) | 2010-06-26 | 2020-12-30 | Virdia, Inc. | Methods for production of sugar mixtures |
| IL206678A0 (en) | 2010-06-28 | 2010-12-30 | Hcl Cleantech Ltd | A method for the production of fermentable sugars |
| IL207329A0 (en) | 2010-08-01 | 2010-12-30 | Robert Jansen | A method for refining a recycle extractant and for processing a lignocellulosic material and for the production of a carbohydrate composition |
| IL207945A0 (en) | 2010-09-02 | 2010-12-30 | Robert Jansen | Method for the production of carbohydrates |
| EP3401322B1 (en) | 2011-04-07 | 2022-06-08 | Virdia, LLC | Lignocellulose conversion processes and products |
| CN104058369B (zh) * | 2014-06-26 | 2016-07-06 | 四川宝利丰科技有限公司 | 聚乙烯醇缩丁醛生产废水中的盐酸回收处理方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3186809A (en) * | 1961-08-10 | 1965-06-01 | Gen Mills Inc | Extraction of mineral acids using dodecylphenol |
| JPS5328398B2 (OSRAM) * | 1971-12-13 | 1978-08-14 | ||
| JPS5134840B2 (OSRAM) * | 1971-12-20 | 1976-09-29 | ||
| FR2227216B1 (OSRAM) * | 1973-04-24 | 1976-11-12 | Commissariat Energie Atomique |
-
1976
- 1976-07-27 DE DE2633640A patent/DE2633640C3/de not_active Expired
-
1977
- 1977-07-14 US US05/815,761 patent/US4115530A/en not_active Expired - Lifetime
- 1977-07-22 FR FR7722568A patent/FR2391950A1/fr active Granted
- 1977-07-25 IT IT50412/77A patent/IT1079361B/it active
- 1977-07-26 BE BE179653A patent/BE857171A/xx not_active IP Right Cessation
- 1977-07-26 NL NL7708283A patent/NL7708283A/xx not_active Application Discontinuation
- 1977-07-26 GB GB31253/77A patent/GB1581770A/en not_active Expired
- 1977-07-26 JP JP52088892A patent/JPS6046041B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5315291A (en) | 1978-02-10 |
| DE2633640A1 (de) | 1978-02-09 |
| NL7708283A (nl) | 1978-01-31 |
| DE2633640C3 (de) | 1979-03-15 |
| IT1079361B (it) | 1985-05-08 |
| BE857171A (fr) | 1978-01-26 |
| FR2391950B1 (OSRAM) | 1985-02-15 |
| DE2633640B2 (de) | 1978-07-13 |
| US4115530A (en) | 1978-09-19 |
| GB1581770A (en) | 1980-12-17 |
| FR2391950A1 (fr) | 1978-12-22 |
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