CA1321600C - Process for the preparation of aminoaryl-.beta.- sulfatoethylsulfone compounds - Google Patents
Process for the preparation of aminoaryl-.beta.- sulfatoethylsulfone compoundsInfo
- Publication number
- CA1321600C CA1321600C CA000585419A CA585419A CA1321600C CA 1321600 C CA1321600 C CA 1321600C CA 000585419 A CA000585419 A CA 000585419A CA 585419 A CA585419 A CA 585419A CA 1321600 C CA1321600 C CA 1321600C
- Authority
- CA
- Canada
- Prior art keywords
- beta
- aniline
- gas
- sulfuric acid
- compound
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 125
- 230000008569 process Effects 0.000 title claims abstract description 83
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 150000001875 compounds Chemical class 0.000 title claims abstract description 26
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 104
- 238000005507 spraying Methods 0.000 claims abstract description 29
- 239000000725 suspension Substances 0.000 claims abstract description 26
- 238000001035 drying Methods 0.000 claims abstract description 22
- 238000005886 esterification reaction Methods 0.000 claims abstract description 18
- -1 acylamino compound Chemical class 0.000 claims abstract description 12
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 10
- 230000007062 hydrolysis Effects 0.000 claims abstract description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 6
- IALORYHODRVWKZ-UHFFFAOYSA-N 2-(4-aminophenyl)sulfonylethyl sulfate;hydron Chemical compound NC1=CC=C(S(=O)(=O)CCOS(O)(=O)=O)C=C1 IALORYHODRVWKZ-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000007789 gas Substances 0.000 claims description 108
- 239000012530 fluid Substances 0.000 claims description 89
- 238000006243 chemical reaction Methods 0.000 claims description 61
- 239000007921 spray Substances 0.000 claims description 47
- 239000007858 starting material Substances 0.000 claims description 27
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 17
- 229960001413 acetanilide Drugs 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 239000008187 granular material Substances 0.000 abstract description 88
- 230000019635 sulfation Effects 0.000 abstract description 9
- 238000005670 sulfation reaction Methods 0.000 abstract description 9
- QQLILYBIARWEIF-UHFFFAOYSA-N 2-(2-hydroxyethylsulfonyl)ethanol Chemical class OCCS(=O)(=O)CCO QQLILYBIARWEIF-UHFFFAOYSA-N 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000012467 final product Substances 0.000 description 46
- 229940032330 sulfuric acid Drugs 0.000 description 43
- 229940039407 aniline Drugs 0.000 description 36
- 239000000203 mixture Substances 0.000 description 30
- 239000000047 product Substances 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 29
- 239000000243 solution Substances 0.000 description 28
- 239000002245 particle Substances 0.000 description 24
- 238000004458 analytical method Methods 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 12
- 239000000428 dust Substances 0.000 description 9
- 239000006072 paste Substances 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 8
- 230000032050 esterification Effects 0.000 description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 8
- 239000007900 aqueous suspension Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000012159 carrier gas Substances 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001180 sulfating effect Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical group Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- HFCSXCKLARAMIQ-UHFFFAOYSA-L disodium;sulfate;hydrate Chemical compound O.[Na+].[Na+].[O-]S([O-])(=O)=O HFCSXCKLARAMIQ-UHFFFAOYSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lighters Containing Fuel (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3742044 | 1987-12-11 | ||
| DEP3742044.5 | 1987-12-11 | ||
| DE3822231 | 1988-07-01 | ||
| DEP3822231.0 | 1988-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1321600C true CA1321600C (en) | 1993-08-24 |
Family
ID=25862684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000585419A Expired - Fee Related CA1321600C (en) | 1987-12-11 | 1988-12-09 | Process for the preparation of aminoaryl-.beta.- sulfatoethylsulfone compounds |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5463100A (esLanguage) |
| EP (1) | EP0390826B1 (esLanguage) |
| JP (1) | JPH03501608A (esLanguage) |
| KR (1) | KR950004047B1 (esLanguage) |
| CN (1) | CN1030984C (esLanguage) |
| AU (1) | AU612758B2 (esLanguage) |
| BR (1) | BR8807840A (esLanguage) |
| CA (1) | CA1321600C (esLanguage) |
| DE (1) | DE3876102D1 (esLanguage) |
| DK (1) | DK141190A (esLanguage) |
| ES (1) | ES2009440A6 (esLanguage) |
| IN (1) | IN172051B (esLanguage) |
| RU (1) | RU1831475C (esLanguage) |
| WO (1) | WO1989005290A1 (esLanguage) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0510480B1 (de) * | 1991-04-23 | 1994-12-14 | Hoechst Aktiengesellschaft | Verfahren zum kontinuierlichen Herstellen von Aminoaryl-oder Aminoalkyl-beta-sulfatoethylsulfonen |
| DE102008004893A1 (de) | 2008-01-17 | 2009-07-23 | Add Technologies Ltd. | Trägerpellets, Verfahren zu deren Herstellung und deren Verwendung |
| CN104922071A (zh) | 2010-04-09 | 2015-09-23 | 帕西拉制药有限公司 | 用于配制大直径合成膜囊泡的方法 |
| CN111170897A (zh) * | 2019-12-18 | 2020-05-19 | 荆门市丽康源纺织科技有限公司 | 一种间位酯的制备方法及间位酯 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3135779A (en) * | 1960-10-06 | 1964-06-02 | Hoechst Ag | Process for preparing ortho-aminophenol-beta-hydroxyethylsulfone sulfuric acid esters |
| CH613947A5 (esLanguage) * | 1976-08-03 | 1979-10-31 | Hoechst Ag | |
| IN152895B (esLanguage) * | 1979-07-19 | 1984-04-28 | Sumitomo Chemical Co | |
| US4482501A (en) * | 1979-07-19 | 1984-11-13 | Sumitomo Chemical Company, Limited | Process for producing aminoaryl-β-sulfatoethylsulfone |
| DE3340114A1 (de) * | 1983-11-05 | 1985-05-15 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von 2-amino-1-hydroxy-4- oder -5- (ss-sulfatoaethylsulfonyl)-benzol-verbindungen und deren verwendung zur synthese von faserreaktiven verbindungen |
-
1988
- 1988-11-24 IN IN967/CAL/88A patent/IN172051B/en unknown
- 1988-11-29 DE DE89900216T patent/DE3876102D1/de not_active Expired - Lifetime
- 1988-11-29 KR KR1019890701499A patent/KR950004047B1/ko not_active Expired - Fee Related
- 1988-11-29 JP JP1500321A patent/JPH03501608A/ja active Pending
- 1988-11-29 EP EP89900216A patent/EP0390826B1/de not_active Expired - Lifetime
- 1988-11-29 AU AU27918/89A patent/AU612758B2/en not_active Ceased
- 1988-11-29 WO PCT/EP1988/001081 patent/WO1989005290A1/de not_active Ceased
- 1988-11-29 BR BR888807840A patent/BR8807840A/pt not_active IP Right Cessation
- 1988-12-09 CN CN88108401A patent/CN1030984C/zh not_active Expired - Fee Related
- 1988-12-09 CA CA000585419A patent/CA1321600C/en not_active Expired - Fee Related
- 1988-12-09 ES ES8803733A patent/ES2009440A6/es not_active Expired
-
1990
- 1990-06-08 RU SU904830253A patent/RU1831475C/ru active
- 1990-06-08 DK DK141190A patent/DK141190A/da not_active Application Discontinuation
-
1994
- 1994-09-06 US US08/301,311 patent/US5463100A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3876102D1 (esLanguage) | 1992-12-24 |
| CN1030984C (zh) | 1996-02-14 |
| KR950004047B1 (ko) | 1995-04-22 |
| JPH03501608A (ja) | 1991-04-11 |
| IN172051B (esLanguage) | 1993-03-27 |
| RU1831475C (ru) | 1993-07-30 |
| AU2791889A (en) | 1989-07-05 |
| EP0390826B1 (de) | 1992-11-19 |
| DK141190D0 (da) | 1990-06-08 |
| EP0390826A1 (de) | 1990-10-10 |
| KR900700440A (ko) | 1990-08-13 |
| US5463100A (en) | 1995-10-31 |
| DK141190A (da) | 1990-06-08 |
| AU612758B2 (en) | 1991-07-18 |
| WO1989005290A1 (fr) | 1989-06-15 |
| BR8807840A (pt) | 1990-11-13 |
| CN1033801A (zh) | 1989-07-12 |
| ES2009440A6 (es) | 1989-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |