CS227027B2 - Method of separating sulphuric acid from the reaction mixture left after paraffine sulphoxidizing - Google Patents
Method of separating sulphuric acid from the reaction mixture left after paraffine sulphoxidizing Download PDFInfo
- Publication number
- CS227027B2 CS227027B2 CS819458A CS945881A CS227027B2 CS 227027 B2 CS227027 B2 CS 227027B2 CS 819458 A CS819458 A CS 819458A CS 945881 A CS945881 A CS 945881A CS 227027 B2 CS227027 B2 CS 227027B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- sulfuric acid
- group
- reaction mixture
- formula
- same meaning
- Prior art date
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims abstract description 75
- 238000000034 method Methods 0.000 title claims abstract description 16
- 239000011541 reaction mixture Substances 0.000 title claims abstract description 10
- 235000011149 sulphuric acid Nutrition 0.000 title 1
- 239000001117 sulphuric acid Substances 0.000 title 1
- 150000001412 amines Chemical class 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 17
- 239000012071 phase Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 239000012188 paraffin wax Substances 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 5
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic diamines Chemical class 0.000 description 3
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 2
- FDECURPHVMNAKO-UHFFFAOYSA-N 4-nonylaniline Chemical compound CCCCCCCCCC1=CC=C(N)C=C1 FDECURPHVMNAKO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 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
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FRQONEWDWWHIPM-UHFFFAOYSA-N n,n-dicyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)C1CCCCC1 FRQONEWDWWHIPM-UHFFFAOYSA-N 0.000 description 2
- MTHFROHDIWGWFD-UHFFFAOYSA-N n-butyl-n-methylbutan-1-amine Chemical compound CCCCN(C)CCCC MTHFROHDIWGWFD-UHFFFAOYSA-N 0.000 description 2
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 2
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- KYZSFZRRZVYDDA-UHFFFAOYSA-N 1,5-dimethylcyclohexa-2,4-dien-1-amine Chemical group CC1(N)CC(=CC=C1)C KYZSFZRRZVYDDA-UHFFFAOYSA-N 0.000 description 1
- QVIAMKXOQGCYCV-UHFFFAOYSA-N 4-methylpentan-1-amine Chemical compound CC(C)CCCN QVIAMKXOQGCYCV-UHFFFAOYSA-N 0.000 description 1
- FBKYCBKRNDJLCX-UHFFFAOYSA-N 5-methylhexan-1-amine Chemical compound CC(C)CCCCN FBKYCBKRNDJLCX-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WVRIJHGUJNXDRZ-UHFFFAOYSA-N ethane-1,1-diamine Chemical compound CC(N)N WVRIJHGUJNXDRZ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- KVPVWLNVUZTSLP-UHFFFAOYSA-N pentan-1-amine;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCN KVPVWLNVUZTSLP-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3048058A DE3048058C2 (de) | 1980-12-19 | 1980-12-19 | Verfahren zur Abtrennung von Schwefelsäure aus dem bei der Sulfoxidation von n-Paraffinen anfallenden rohen Sulfonierungsgemisch |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS227027B2 true CS227027B2 (en) | 1984-04-16 |
Family
ID=6119706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS819458A CS227027B2 (en) | 1980-12-19 | 1981-12-17 | Method of separating sulphuric acid from the reaction mixture left after paraffine sulphoxidizing |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0054851B1 (fr) |
| JP (1) | JPS57128670A (fr) |
| AR (1) | AR227216A1 (fr) |
| AT (1) | ATE8254T1 (fr) |
| AU (1) | AU7865181A (fr) |
| BR (1) | BR8108267A (fr) |
| CS (1) | CS227027B2 (fr) |
| DD (1) | DD202008A5 (fr) |
| DE (2) | DE3048058C2 (fr) |
| ES (1) | ES507934A0 (fr) |
| NO (1) | NO814347L (fr) |
| YU (1) | YU301681A (fr) |
| ZA (1) | ZA818760B (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3210573A1 (de) * | 1982-03-23 | 1983-10-06 | Hoechst Ag | Verfahren zum abtrennen von schwefelsaeure aus dem bei der sulfoxidation von paraffinen anfallenden reaktionsgemisch |
| IT1213575B (it) * | 1986-12-23 | 1989-12-20 | Eniricerche Spa | Procedimenti per la separazione di acido solforico da miscele acquose dello stesso con acidi paraffisolfonici. |
| IT1198232B (it) * | 1986-12-23 | 1988-12-21 | Eniricerche Spa | Procedimento per la separazione di acido solforico da miscele acquose dello stesso con acidi paraffinsolfonici |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1568591B2 (de) * | 1966-09-10 | 1976-06-10 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung alkalisulfatarmer alkaliparaffinsulfonatloesungen |
| DE1934154A1 (de) * | 1968-09-20 | 1970-05-27 | Hydrierwerk Rodleben Veb | Verfahren zur Herstellung hellfarbiger fremdsalzarmer Alkansulfonate |
| DE2065477C3 (de) * | 1969-03-28 | 1974-09-26 | Lion Fat & Oil Co., Ltd., Tokio | Verfahren zur Abtrennung von Schwefelsäure aus einem Reaktionsgemisch. Ausscheidung aus: 2014783 |
| JPS4843099B1 (fr) * | 1969-09-11 | 1973-12-17 | ||
| US3720707A (en) * | 1970-02-27 | 1973-03-13 | Labofina Sa | Process for reducing the sulfuric acid content of alkylarylsulfonic acids |
| BG20344A3 (bg) * | 1970-08-07 | 1975-11-05 | Ato Chimie | Метод за отделяне на сулфонови киселини и сулфонати |
| SU621675A1 (ru) * | 1976-04-05 | 1978-08-30 | Предприятие П/Я В-2287 | Способ получени щелочных солей алкилсульфокислот |
| FR2367740A1 (fr) * | 1976-10-15 | 1978-05-12 | Ato Chimie | Pro |
| IT1074825B (it) * | 1977-01-11 | 1985-04-20 | Euteco Spa | Procedimento per la purificazione di acidi alchilsolfonici |
-
1980
- 1980-12-19 DE DE3048058A patent/DE3048058C2/de not_active Expired
-
1981
- 1981-12-10 AT AT81110309T patent/ATE8254T1/de not_active IP Right Cessation
- 1981-12-10 DE DE8181110309T patent/DE3164616D1/de not_active Expired
- 1981-12-10 EP EP81110309A patent/EP0054851B1/fr not_active Expired
- 1981-12-14 ES ES507934A patent/ES507934A0/es active Granted
- 1981-12-17 AR AR287851A patent/AR227216A1/es active
- 1981-12-17 DD DD81235900A patent/DD202008A5/de unknown
- 1981-12-17 CS CS819458A patent/CS227027B2/cs unknown
- 1981-12-18 BR BR8108267A patent/BR8108267A/pt unknown
- 1981-12-18 NO NO814347A patent/NO814347L/no unknown
- 1981-12-18 YU YU03016/81A patent/YU301681A/xx unknown
- 1981-12-18 JP JP56203853A patent/JPS57128670A/ja active Pending
- 1981-12-18 AU AU78651/81A patent/AU7865181A/en not_active Abandoned
- 1981-12-18 ZA ZA818760A patent/ZA818760B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE8254T1 (de) | 1984-07-15 |
| AR227216A1 (es) | 1982-09-30 |
| ES8207094A1 (es) | 1982-09-01 |
| DE3048058A1 (de) | 1982-07-01 |
| EP0054851A1 (fr) | 1982-06-30 |
| JPS57128670A (en) | 1982-08-10 |
| AU7865181A (en) | 1982-06-24 |
| ZA818760B (en) | 1982-11-24 |
| BR8108267A (pt) | 1982-10-05 |
| DD202008A5 (de) | 1983-08-24 |
| DE3164616D1 (en) | 1984-08-09 |
| NO814347L (no) | 1982-06-21 |
| DE3048058C2 (de) | 1983-04-28 |
| ES507934A0 (es) | 1982-09-01 |
| YU301681A (en) | 1983-02-28 |
| EP0054851B1 (fr) | 1984-07-04 |
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