DE2156087A1 - Sulfonierungsverfahren - Google Patents
SulfonierungsverfahrenInfo
- Publication number
- DE2156087A1 DE2156087A1 DE19712156087 DE2156087A DE2156087A1 DE 2156087 A1 DE2156087 A1 DE 2156087A1 DE 19712156087 DE19712156087 DE 19712156087 DE 2156087 A DE2156087 A DE 2156087A DE 2156087 A1 DE2156087 A1 DE 2156087A1
- Authority
- DE
- Germany
- Prior art keywords
- sulfonation
- hydrocarbons
- base
- neutralization
- sulfonatable
- 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.)
- Pending
Links
- 229930195733 hydrocarbon Natural products 0.000 claims description 56
- 238000006277 sulfonation reaction Methods 0.000 claims description 54
- 150000002430 hydrocarbons Chemical class 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 36
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 36
- 238000006386 neutralization reaction Methods 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 31
- 239000012074 organic phase Substances 0.000 claims description 28
- 238000007127 saponification reaction Methods 0.000 claims description 21
- 239000008346 aqueous phase Substances 0.000 claims description 20
- 239000003599 detergent Substances 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 14
- 239000012071 phase Substances 0.000 claims description 14
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000005673 monoalkenes Chemical class 0.000 claims description 6
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 238000004064 recycling Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 150000001336 alkenes Chemical class 0.000 description 16
- -1 olefin sulfonates Chemical class 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000008053 sultones Chemical class 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000004996 alkyl benzenes Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052785 arsenic Inorganic materials 0.000 description 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
- C07C5/333—Catalytic processes
- C07C5/3335—Catalytic processes with metals
- C07C5/3337—Catalytic processes with metals of the platinum group
-
- 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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
-
- 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
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7042195A FR2115557A5 (enExample) | 1970-11-24 | 1970-11-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2156087A1 true DE2156087A1 (de) | 1972-06-29 |
Family
ID=9064641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712156087 Pending DE2156087A1 (de) | 1970-11-24 | 1971-11-11 | Sulfonierungsverfahren |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3803058A (enExample) |
| AT (1) | AT313308B (enExample) |
| BE (1) | BE775549A (enExample) |
| CA (1) | CA955263A (enExample) |
| CH (1) | CH540889A (enExample) |
| DE (1) | DE2156087A1 (enExample) |
| FR (1) | FR2115557A5 (enExample) |
| GB (1) | GB1328743A (enExample) |
| IT (1) | IT941232B (enExample) |
| LU (1) | LU64332A1 (enExample) |
| NL (1) | NL7116154A (enExample) |
| SE (1) | SE381652B (enExample) |
| ZA (1) | ZA717835B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996016032A1 (de) * | 1994-11-23 | 1996-05-30 | HÜLS Aktiengesellschaft | Verfahren zur herstellung von alkylbenzolsulfonsäure |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA990608A (en) * | 1972-08-03 | 1976-06-08 | Virender N. Malhotra | Preparation of detergent materials |
| US20040003834A1 (en) * | 2002-05-01 | 2004-01-08 | Bruce Arnett | Modular carwash assembly |
| US9108906B2 (en) | 2012-03-22 | 2015-08-18 | Uop Llc | Production of alkane sulfonates |
-
1970
- 1970-11-24 FR FR7042195A patent/FR2115557A5/fr not_active Expired
-
1971
- 1971-11-11 DE DE19712156087 patent/DE2156087A1/de active Pending
- 1971-11-12 CH CH1644171A patent/CH540889A/fr not_active IP Right Cessation
- 1971-11-19 BE BE775549A patent/BE775549A/xx unknown
- 1971-11-20 IT IT31422/71A patent/IT941232B/it active
- 1971-11-22 GB GB5422471A patent/GB1328743A/en not_active Expired
- 1971-11-22 ZA ZA717835A patent/ZA717835B/xx unknown
- 1971-11-23 SE SE7114997A patent/SE381652B/xx unknown
- 1971-11-23 US US00201501A patent/US3803058A/en not_active Expired - Lifetime
- 1971-11-23 AT AT1008671A patent/AT313308B/de not_active IP Right Cessation
- 1971-11-23 CA CA128,373A patent/CA955263A/en not_active Expired
- 1971-11-24 LU LU64332D patent/LU64332A1/xx unknown
- 1971-11-24 NL NL7116154A patent/NL7116154A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996016032A1 (de) * | 1994-11-23 | 1996-05-30 | HÜLS Aktiengesellschaft | Verfahren zur herstellung von alkylbenzolsulfonsäure |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1328743A (en) | 1973-08-30 |
| IT941232B (it) | 1973-03-01 |
| CA955263A (en) | 1974-09-24 |
| LU64332A1 (enExample) | 1972-06-19 |
| CH540889A (fr) | 1973-08-31 |
| SE381652B (sv) | 1975-12-15 |
| AT313308B (de) | 1974-02-11 |
| FR2115557A5 (enExample) | 1972-07-07 |
| BE775549A (fr) | 1972-05-19 |
| US3803058A (en) | 1974-04-09 |
| NL7116154A (enExample) | 1972-05-26 |
| ZA717835B (en) | 1972-08-30 |
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