BE583999A - - Google Patents
Info
- Publication number
- BE583999A BE583999A BE583999DA BE583999A BE 583999 A BE583999 A BE 583999A BE 583999D A BE583999D A BE 583999DA BE 583999 A BE583999 A BE 583999A
- Authority
- BE
- Belgium
- Prior art keywords
- reaction
- sep
- sulfonic acid
- process according
- sulfonation
- Prior art date
Links
- AKEJUJNQAAGONA-UHFFFAOYSA-N Sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 44
- 238000006277 sulfonation reaction Methods 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N Boron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 16
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-Phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 claims description 15
- 229910052810 boron oxide Inorganic materials 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 12
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 10
- 150000001491 aromatic compounds Chemical class 0.000 claims description 9
- -1 aromatic vinyl sulfonic acid salt Chemical class 0.000 claims description 9
- 239000006227 byproduct Substances 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000005755 formation reaction Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- FDYYGZOWHGEICH-UHFFFAOYSA-N 1-(2-bromoethyl)-2,3-dichlorobenzene Chemical compound ClC1=CC=CC(CCBr)=C1Cl FDYYGZOWHGEICH-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- XMZQWZJMTBCUFT-UHFFFAOYSA-N 3-bromopropylbenzene Chemical compound BrCCCC1=CC=CC=C1 XMZQWZJMTBCUFT-UHFFFAOYSA-N 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000002378 acidificating Effects 0.000 claims description 2
- 230000005591 charge neutralization Effects 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000002198 insoluble material Substances 0.000 claims description 2
- 230000001264 neutralization Effects 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 239000011343 solid material Substances 0.000 claims description 2
- HUXJRTPIDCQELS-UHFFFAOYSA-N 1-phenylbuta-1,3-diene-2-sulfonic acid Chemical compound OS(=O)(=O)C(C=C)=CC1=CC=CC=C1 HUXJRTPIDCQELS-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N Vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 150000003871 sulfonates Chemical class 0.000 claims 1
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 77
- 239000000243 solution Substances 0.000 description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000003756 stirring Methods 0.000 description 12
- VPXYRQWRQLIJQC-UHFFFAOYSA-N 2-(2-bromoethyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1CCBr VPXYRQWRQLIJQC-UHFFFAOYSA-N 0.000 description 10
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 10
- 150000003457 sulfones Chemical class 0.000 description 9
- JHJLBTNAGRQEKS-UHFFFAOYSA-M Sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 7
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 7
- 239000003518 caustics Substances 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 238000000605 extraction Methods 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 229940075581 sodium bromide Drugs 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- SSZRKTMOQXDFHT-UHFFFAOYSA-N BrCCC1=C(C=CC=C1)S(=O)(=O)C1=C(C=CC=C1)CCBr Chemical compound BrCCC1=C(C=CC=C1)S(=O)(=O)C1=C(C=CC=C1)CCBr SSZRKTMOQXDFHT-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- PWHMFVALYNYYMZ-UHFFFAOYSA-N ethenyl phenylmethanesulfonate;sodium Chemical compound [Na].C=COS(=O)(=O)CC1=CC=CC=C1 PWHMFVALYNYYMZ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- DFFGENKQIJGPFC-UHFFFAOYSA-M ClC(=C(S(=O)(=O)[O-])Cl)C1=CC=CC=C1.[Na+] Chemical compound ClC(=C(S(=O)(=O)[O-])Cl)C1=CC=CC=C1.[Na+] DFFGENKQIJGPFC-UHFFFAOYSA-M 0.000 description 2
- 210000004940 Nucleus Anatomy 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000007269 dehydrobromination reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2S)-2-aminopentanedioic acid;hydrochloride Chemical compound Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- GZPRFUSTANBATG-UHFFFAOYSA-N 2-(2-bromoethyl)phenol Chemical compound OC1=CC=CC=C1CCBr GZPRFUSTANBATG-UHFFFAOYSA-N 0.000 description 1
- FMTBJQITXVJVDA-UHFFFAOYSA-N 2-(2-chloroethyl)naphthalene Chemical compound C1=CC=CC2=CC(CCCl)=CC=C21 FMTBJQITXVJVDA-UHFFFAOYSA-N 0.000 description 1
- OMDLWRFQBASTTR-UHFFFAOYSA-N BrCCC1=C(C=CC=C1)S(=O)(=O)OS(=O)(=O)C1=C(C=CC=C1)CCBr Chemical compound BrCCC1=C(C=CC=C1)S(=O)(=O)OS(=O)(=O)C1=C(C=CC=C1)CCBr OMDLWRFQBASTTR-UHFFFAOYSA-N 0.000 description 1
- 230000036099 Cav Effects 0.000 description 1
- 229920002456 HOTAIR Polymers 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 244000245420 ail Species 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000000670 limiting Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002829 reduced Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- JJMIAJGBZGZNHA-UHFFFAOYSA-N sodium;styrene Chemical compound [Na].C=CC1=CC=CC=C1 JJMIAJGBZGZNHA-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000000087 stabilizing Effects 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001131 transforming Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE583999A true BE583999A (ja) |
Family
ID=191423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE583999D BE583999A (ja) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE583999A (ja) |
-
0
- BE BE583999D patent/BE583999A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2114277C (fr) | Procede perfectionne de fabrication de (meth)acrylates d'alkyle par esterification directe | |
| EP0165135B1 (fr) | Procédé de préparation d'acides trifluorométhylés | |
| EP0153222B1 (fr) | Procédé de préparation de para acyloxybenzènesulfonates par catalyse acide | |
| CH624377A5 (ja) | ||
| EP0037349B1 (fr) | Procédé de préparation d'O,O-diméthyl-phosphorodithioate de mercaptosuccinate d'ethyl (malathion(R)) | |
| BE583999A (ja) | ||
| FR2649099A1 (fr) | Procede de purification des trifluoromethanesulfinate et sulfonate de sodium | |
| EP0000464B1 (fr) | Procédé de purification du mercaptobenzothiazole | |
| US3079430A (en) | Process for preparing vinylaromatic sulfonic acid salts | |
| BE499518A (ja) | ||
| FR2610319A1 (fr) | Procede de preparation de derives d'acides perhalogenoalcanesulfiniques et sulfoniques | |
| EP0382617B1 (fr) | Synthèse d'alcanedithiols vicinaux | |
| FR2583040A1 (fr) | Procede pour la production de 2,6-naphtalenediol et de 2,6-diacetoxynaphtalene | |
| BE498029A (ja) | ||
| FR2661409A1 (fr) | Procede de purification des trifluoromethanesulfinate et sulfonate de sodium. | |
| FR2481700A1 (fr) | Procede de purification d'ether sulfonates | |
| BE520742A (ja) | ||
| CH285772A (fr) | Procédé de préparation du bêta-naphtol. | |
| CH428739A (fr) | Procédé de préparation de lactames | |
| BE623996A (ja) | ||
| BE539211A (ja) | ||
| BE555380A (ja) | ||
| BE490259A (fr) | Perfectionnements à la préparation des composés phénoliques | |
| BE629434A (ja) | ||
| BE421440A (ja) |