BE660053A - - Google Patents
Info
- Publication number
- BE660053A BE660053A BE660053DA BE660053A BE 660053 A BE660053 A BE 660053A BE 660053D A BE660053D A BE 660053DA BE 660053 A BE660053 A BE 660053A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- methyl
- reaction
- solution
- trialkylamine
- Prior art date
Links
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 56
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 54
- 239000007864 aqueous solution Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000005270 trialkylamine group Chemical group 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 150000001555 benzenes Chemical class 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 238000001704 evaporation Methods 0.000 claims description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 6
- 150000003460 sulfonic acids Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims description 4
- MLWCXAHUCWLIJB-UHFFFAOYSA-M benzenesulfonate;tetramethylazanium Chemical compound C[N+](C)(C)C.[O-]S(=O)(=O)C1=CC=CC=C1 MLWCXAHUCWLIJB-UHFFFAOYSA-M 0.000 claims description 3
- 239000012266 salt solution Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 44
- 150000001412 amines Chemical class 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 23
- -1 quaternary ammonium sulfonates Chemical class 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 18
- 239000012535 impurity Substances 0.000 description 11
- 239000003792 electrolyte Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- CVLHGLWXLDOELD-UHFFFAOYSA-N 4-(Propan-2-yl)benzenesulfonic acid Chemical class CC(C)C1=CC=C(S(O)(=O)=O)C=C1 CVLHGLWXLDOELD-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 4
- JSAWRAZHLDUMBF-UHFFFAOYSA-N 4-(2-methylbutan-2-yl)benzenesulfonic acid Chemical class CCC(C)(C)C1=CC=C(S(O)(=O)=O)C=C1 JSAWRAZHLDUMBF-UHFFFAOYSA-N 0.000 description 3
- JNVFIMNBBVDEPV-UHFFFAOYSA-N 4-butylbenzenesulfonic acid Chemical class CCCCC1=CC=C(S(O)(=O)=O)C=C1 JNVFIMNBBVDEPV-UHFFFAOYSA-N 0.000 description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 3
- 229940077388 benzenesulfonate Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- HEKJKEPWBONQQC-UHFFFAOYSA-N benzenesulfonic acid;n,n-dimethylmethanamine Chemical compound C[NH+](C)C.[O-]S(=O)(=O)C1=CC=CC=C1 HEKJKEPWBONQQC-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- JSRNAXPCTSZMIA-UHFFFAOYSA-N methyl 1,6-dipropylcyclohexa-2,4-diene-1-sulfonate Chemical compound C(CC)C1(C(C=CC=C1)CCC)S(=O)(=O)OC JSRNAXPCTSZMIA-UHFFFAOYSA-N 0.000 description 2
- VCXKHPUXNZJDDG-UHFFFAOYSA-N methyl 2,4,6-trimethylbenzenesulfonate Chemical compound COS(=O)(=O)C1=C(C)C=C(C)C=C1C VCXKHPUXNZJDDG-UHFFFAOYSA-N 0.000 description 2
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
- 239000012457 nonaqueous media Substances 0.000 description 2
- WUAQPEPYBDNYSK-UHFFFAOYSA-N phenylmethanesulfonate;trimethylazanium Chemical compound C[NH+](C)C.[O-]S(=O)(=O)CC1=CC=CC=C1 WUAQPEPYBDNYSK-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QSHKDIHEZKCYDU-UHFFFAOYSA-N 1,5-dimethylcyclohexa-2,4-diene-1-sulfonic acid Chemical compound C1(CC(=CC=C1)C)(C)S(=O)(=O)O QSHKDIHEZKCYDU-UHFFFAOYSA-N 0.000 description 1
- MWDDHFDRDIDFGK-UHFFFAOYSA-M 1,6-dimethylcyclohexa-2,4-diene-1-sulfonate tetramethylazanium Chemical compound C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-].C[N+](C)(C)C MWDDHFDRDIDFGK-UHFFFAOYSA-M 0.000 description 1
- KJJMOCUMRBSKTE-UHFFFAOYSA-N 2,3,5,6-tetramethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(C)C(S(O)(=O)=O)=C1C KJJMOCUMRBSKTE-UHFFFAOYSA-N 0.000 description 1
- BRIXOPDYGQCZFO-UHFFFAOYSA-M 4-ethylbenzenesulfonate Chemical compound CCC1=CC=C(S([O-])(=O)=O)C=C1 BRIXOPDYGQCZFO-UHFFFAOYSA-M 0.000 description 1
- BRIXOPDYGQCZFO-UHFFFAOYSA-N 4-ethylphenylsulfonic acid Chemical class CCC1=CC=C(S(O)(=O)=O)C=C1 BRIXOPDYGQCZFO-UHFFFAOYSA-N 0.000 description 1
- QKFFSWPNFCXGIQ-UHFFFAOYSA-M 4-methylbenzenesulfonate;tetraethylazanium Chemical compound CC[N+](CC)(CC)CC.CC1=CC=C(S([O-])(=O)=O)C=C1 QKFFSWPNFCXGIQ-UHFFFAOYSA-M 0.000 description 1
- MMVUZMIOJNPDME-UHFFFAOYSA-N 4-methylbenzenesulfonate;triethylazanium Chemical compound CC[NH+](CC)CC.CC1=CC=C(S([O-])(=O)=O)C=C1 MMVUZMIOJNPDME-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BIPBSTLZJOLTED-UHFFFAOYSA-M C1(=C(C(=CC(=C1)C)C)S(=O)(=O)[O-])C.C[N+](CC)(CC)CC Chemical compound C1(=C(C(=CC(=C1)C)C)S(=O)(=O)[O-])C.C[N+](CC)(CC)CC BIPBSTLZJOLTED-UHFFFAOYSA-M 0.000 description 1
- PDQHJNSJXAZBLQ-UHFFFAOYSA-M C1(=CC=CC=C1)S(=O)(=O)[O-].C(C)[N+](C)(CC)CC Chemical compound C1(=CC=CC=C1)S(=O)(=O)[O-].C(C)[N+](C)(CC)CC PDQHJNSJXAZBLQ-UHFFFAOYSA-M 0.000 description 1
- VCSMFSLYPSQTMT-UHFFFAOYSA-N C1(C(C=CC=C1)C)(C)S(=O)(=O)OC Chemical compound C1(C(C=CC=C1)C)(C)S(=O)(=O)OC VCSMFSLYPSQTMT-UHFFFAOYSA-N 0.000 description 1
- LGICBZHCODUFLR-UHFFFAOYSA-N C1(CC=C(C=C1)C)(C)S(=O)(=O)OC Chemical compound C1(CC=C(C=C1)C)(C)S(=O)(=O)OC LGICBZHCODUFLR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MXFPOATVZPASET-UHFFFAOYSA-N methyl 4-butylbenzenesulfonate Chemical compound CCCCC1=CC=C(S(=O)(=O)OC)C=C1 MXFPOATVZPASET-UHFFFAOYSA-N 0.000 description 1
- MNRGFUBMMILKAL-UHFFFAOYSA-N methyl phenylmethanesulfonate Chemical compound COS(=O)(=O)CC1=CC=CC=C1 MNRGFUBMMILKAL-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- PCLMJMPFXXJDNE-UHFFFAOYSA-M tetramethylazanium 2,4,6-trimethylbenzenesulfonate Chemical compound C1(=C(C(=CC(=C1)C)C)S(=O)(=O)[O-])C.C[N+](C)(C)C PCLMJMPFXXJDNE-UHFFFAOYSA-M 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000004954 trialkylamino group Chemical group 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B42—BOOKBINDING; ALBUMS; FILES; SPECIAL PRINTED MATTER
- B42F—SHEETS TEMPORARILY ATTACHED TOGETHER; FILING APPLIANCES; FILE CARDS; INDEXING
- B42F21/00—Indexing means; Indexing tabs or protectors therefor
- B42F21/06—Tabs detachably mounted on sheets, papers, cards, or suspension files
- B42F21/08—Tabs detachably mounted on sheets, papers, cards, or suspension files in one of a number of predetermined positions
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34730264A | 1964-02-26 | 1964-02-26 | |
| GB3945464A GB1103504A (en) | 1964-09-28 | 1964-09-28 | Improvements in or relating to filing systems |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE660053A true BE660053A (enrdf_load_stackoverflow) | 1966-03-24 |
Family
ID=26264111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE660053D BE660053A (enrdf_load_stackoverflow) | 1964-02-26 | 1965-09-24 |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE660053A (enrdf_load_stackoverflow) |
-
1965
- 1965-09-24 BE BE660053D patent/BE660053A/fr unknown
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