GB1581770A - Process for isolating gaseous hydrogen chloride from dilute aqueous hydrochloric acid - Google Patents
Process for isolating gaseous hydrogen chloride from dilute aqueous hydrochloric acid Download PDFInfo
- Publication number
- GB1581770A GB1581770A GB31253/77A GB3125377A GB1581770A GB 1581770 A GB1581770 A GB 1581770A GB 31253/77 A GB31253/77 A GB 31253/77A GB 3125377 A GB3125377 A GB 3125377A GB 1581770 A GB1581770 A GB 1581770A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen chloride
- amine
- water
- carbon atoms
- solvent
- 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 216
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 title claims description 159
- 229910000041 hydrogen chloride Inorganic materials 0.000 title claims description 159
- 238000000034 method Methods 0.000 title claims description 35
- 150000001412 amines Chemical class 0.000 claims description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 37
- 239000012071 phase Substances 0.000 claims description 34
- 238000000605 extraction Methods 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 238000010992 reflux Methods 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000012074 organic phase Substances 0.000 claims description 18
- 239000000284 extract Substances 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 150000003973 alkyl amines Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- SZRUMHWRJNVJJC-UHFFFAOYSA-N chlorobenzene;1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1.ClC1=CC=CC=C1Cl SZRUMHWRJNVJJC-UHFFFAOYSA-N 0.000 claims description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 2
- YWBXIPUOAUKRGD-UHFFFAOYSA-N chloroethane chloroethene Chemical compound C(C)Cl.C(=C)Cl YWBXIPUOAUKRGD-UHFFFAOYSA-N 0.000 claims 1
- 150000003997 cyclic ketones Chemical class 0.000 claims 1
- 150000001983 dialkylethers Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 28
- 239000008346 aqueous phase Substances 0.000 description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 15
- 239000008096 xylene Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- -1 aliphatic radical Chemical class 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- GCULWAWIZUGXTO-UHFFFAOYSA-N n-octylaniline Chemical compound CCCCCCCCNC1=CC=CC=C1 GCULWAWIZUGXTO-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 238000010494 dissociation reaction Methods 0.000 description 4
- 230000005593 dissociations Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005192 partition Methods 0.000 description 4
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 4
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- FZPXKEPZZOEPGX-UHFFFAOYSA-N n,n-dibutylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1 FZPXKEPZZOEPGX-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- QHTJSSMHBLGUHV-UHFFFAOYSA-N 2-methylbutan-2-ylbenzene Chemical compound CCC(C)(C)C1=CC=CC=C1 QHTJSSMHBLGUHV-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 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
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- 238000003833 Wallach reaction Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 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
- PZTVYZVWAHUIMY-UHFFFAOYSA-N n,n,13-trimethyltetradecan-1-amine Chemical class CC(C)CCCCCCCCCCCCN(C)C PZTVYZVWAHUIMY-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
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 2
- XGQJZNCFDLXSIJ-UHFFFAOYSA-N pentadecanal Chemical class CCCCCCCCCCCCCCC=O XGQJZNCFDLXSIJ-UHFFFAOYSA-N 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 2
- 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
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- AILVYPLQKCQNJC-UHFFFAOYSA-N 2,6-dimethylcyclohexan-1-one Chemical compound CC1CCCC(C)C1=O AILVYPLQKCQNJC-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- HYYUPDIHVSXPJV-UHFFFAOYSA-N 2-butyl-n,n-diethyl-4-methylaniline Chemical compound CCCCC1=CC(C)=CC=C1N(CC)CC HYYUPDIHVSXPJV-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
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- YQACQZUSGCPUPO-UHFFFAOYSA-N 4-(2-ethylhexyl)aniline Chemical compound CCCCC(CC)CC1=CC=C(N)C=C1 YQACQZUSGCPUPO-UHFFFAOYSA-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
- 239000004215 Carbon black (E152) Substances 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 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
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- PEXSHBLAUSWRQB-UHFFFAOYSA-N decane 1,2,3,4-tetrahydronaphthalene Chemical compound C1CCCC2=CC=CC=C12.CCCCCCCCCC PEXSHBLAUSWRQB-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 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
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 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
- INKUHEVVHHFDIS-UHFFFAOYSA-N n,n-diethyl-2-hexyl-4-methylaniline Chemical compound CCCCCCC1=CC(C)=CC=C1N(CC)CC INKUHEVVHHFDIS-UHFFFAOYSA-N 0.000 description 1
- GDLQHGLLUIWQAD-UHFFFAOYSA-N n,n-diheptyl-4-methylaniline Chemical compound CCCCCCCN(CCCCCCC)C1=CC=C(C)C=C1 GDLQHGLLUIWQAD-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
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- PTRSTXBRQVXIEW-UHFFFAOYSA-N n,n-dioctylaniline Chemical compound CCCCCCCCN(CCCCCCCC)C1=CC=CC=C1 PTRSTXBRQVXIEW-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
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-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
- XZJYVGRDKYPYRM-UHFFFAOYSA-N n-dodecyl-n-ethylaniline Chemical compound CCCCCCCCCCCCN(CC)C1=CC=CC=C1 XZJYVGRDKYPYRM-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
- UWHRNIXHZAWBMF-UHFFFAOYSA-N n-dodecyl-n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)CCCCCCCCCCCC UWHRNIXHZAWBMF-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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- UEKWTIYPDJLSKK-UHFFFAOYSA-N n-octadecylaniline Chemical compound CCCCCCCCCCCCCCCCCCNC1=CC=CC=C1 UEKWTIYPDJLSKK-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- FQSDTIQFGVAWNS-UHFFFAOYSA-N rhodium;(triphenyl-$l^{5}-phosphanylidene)methanone Chemical compound [Rh].C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C=O)C1=CC=CC=C1 FQSDTIQFGVAWNS-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- FHYUCVWDMABHHH-UHFFFAOYSA-N toluene;1,2-xylene Chemical group CC1=CC=CC=C1.CC1=CC=CC=C1C FHYUCVWDMABHHH-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 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 (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1581770A true GB1581770A (en) | 1980-12-17 |
Family
ID=5984015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31253/77A Expired GB1581770A (en) | 1976-07-27 | 1977-07-26 | Process for isolating gaseous hydrogen chloride from dilute aqueous hydrochloric acid |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4115530A (enExample) |
| JP (1) | JPS6046041B2 (enExample) |
| BE (1) | BE857171A (enExample) |
| DE (1) | DE2633640C3 (enExample) |
| FR (1) | FR2391950A1 (enExample) |
| GB (1) | GB1581770A (enExample) |
| IT (1) | IT1079361B (enExample) |
| NL (1) | NL7708283A (enExample) |
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 (enExample) * | 1971-12-13 | 1978-08-14 | ||
| JPS5134840B2 (enExample) * | 1971-12-20 | 1976-09-29 | ||
| FR2227216B1 (enExample) * | 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 (enExample) | 1985-02-15 |
| JPS6046041B2 (ja) | 1985-10-14 |
| DE2633640B2 (de) | 1978-07-13 |
| US4115530A (en) | 1978-09-19 |
| FR2391950A1 (fr) | 1978-12-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1581770A (en) | Process for isolating gaseous hydrogen chloride from dilute aqueous hydrochloric acid | |
| AU748827B2 (en) | Method for producing an aqueous solution of free hydroxylamine | |
| RU2010146085A (ru) | Способ получения изоцианата | |
| US4032411A (en) | Process for the preparation of ethylene diamine having low water content | |
| EP0110470B1 (en) | Process for the recovery of ethylene amines from an aqueous solution | |
| CN102030627A (zh) | 用来从甲基丙烯酸甲酯纯化产生的物流中回收有价值的化合物的方法 | |
| US4259309A (en) | Method for obtaining gaseous hydrogen chloride from dilute aqueous hydrochloric acid | |
| EP0037695B1 (en) | Methylamines purification process | |
| JP3502523B2 (ja) | アルキルハロゲン化物の連続的な製法 | |
| JPH0789916A (ja) | Ｎ−ビニルカルボン酸アミドの精製方法 | |
| EP0041837A1 (en) | Process for the purification of p-aminophenol | |
| US4119497A (en) | Process for the purification of acetonitrile | |
| NO327886B1 (no) | Apparat og en fremgangsmate for fremstilling av vannfri eller hovedsakelig vannfri maursyre samt anvendelse av ekstraksjonsmidlet | |
| EP0008330B1 (de) | Verfahren zur Trennung von Chlorwasserstoff und Bromwasserstoff | |
| EP0597151A1 (en) | Method for preparing formic acid | |
| US3878058A (en) | Recovery of alkylvinylether by extractive distillation of a feed containing only trace amounts of water | |
| JPS5946884B2 (ja) | 希薄塩酸水溶液から気体状塩化水素を得る方法 | |
| US4305917A (en) | Method for preparing ammonia and hydrogen chloride from ammonium chloride | |
| CN112739675A (zh) | 回收高品质3-甲基-丁-3-烯-1-醇的方法 | |
| JPH0789917A (ja) | Ｎ−ビニルカルボン酸アミドの精製方法 | |
| MXPA02002715A (es) | Procedimiento para la produccion y purificacion de acrilato de n-butilo. | |
| US4967019A (en) | Method of manufacturing 2-propyn-1-ol | |
| US4061633A (en) | Method of recovering primary and secondary amines | |
| CA1157228A (en) | Method for producing sodium hydrogen-carbonate and hydrogen-chloride | |
| JPH01139537A (ja) | シクロヘキセンの分離方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |