NO135635B - - Google Patents
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- Publication number
- NO135635B NO135635B NO2945/71A NO294571A NO135635B NO 135635 B NO135635 B NO 135635B NO 2945/71 A NO2945/71 A NO 2945/71A NO 294571 A NO294571 A NO 294571A NO 135635 B NO135635 B NO 135635B
- Authority
- NO
- Norway
- Prior art keywords
- acids
- paraffins
- organic phase
- sulfuric acid
- solution
- Prior art date
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 78
- 239000000243 solution Substances 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 39
- 150000007513 acids Chemical class 0.000 claims description 38
- 239000012074 organic phase Substances 0.000 claims description 23
- 239000012071 phase Substances 0.000 claims description 21
- 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 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000000926 separation method Methods 0.000 claims description 16
- 239000008346 aqueous phase Substances 0.000 claims description 13
- 150000003460 sulfonic acids Chemical class 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 6
- 150000001447 alkali salts Chemical class 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 238000005185 salting out Methods 0.000 claims description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000012188 paraffin wax Substances 0.000 description 21
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 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 9
- 230000001476 alcoholic effect Effects 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 8
- 239000002798 polar solvent Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000000889 atomisation Methods 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 238000002386 leaching Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- -1 sodium and potassium Chemical class 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- 239000005968 1-Decanol Substances 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- LWWJDXKGQVEZKT-UHFFFAOYSA-N 3-ethylhexan-1-ol Chemical compound CCCC(CC)CCO LWWJDXKGQVEZKT-UHFFFAOYSA-N 0.000 description 1
- YVBCULSIZWMTFY-UHFFFAOYSA-N 4-Heptanol Natural products CCCC(O)CCC YVBCULSIZWMTFY-UHFFFAOYSA-N 0.000 description 1
- RYFZXYQQFYLUHM-UHFFFAOYSA-N 7,7-dimethyloctan-1-ol Chemical compound CC(C)(C)CCCCCCO RYFZXYQQFYLUHM-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000002152 aqueous-organic solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical class C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000032258 transport Effects 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7029211A FR2102540A5 (en) | 1970-08-07 | 1970-08-07 | Sepn of sulphonic acids - from solns also contg sulphuric water and unsulphonated hydrocarbons |
| FR7126794A FR2146650A6 (en) | 1971-07-22 | 1971-07-22 | Sepn of sulphonic acids - from solns also contg sulphuric water and unsulphonated hydrocarbons |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135635B true NO135635B (it) | 1977-01-24 |
| NO135635C NO135635C (it) | 1977-05-04 |
Family
ID=26215890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2945/71A NO135635C (it) | 1970-08-07 | 1971-08-05 |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS505689B1 (it) |
| BE (1) | BE771038A (it) |
| BG (1) | BG20344A3 (it) |
| CA (1) | CA952122A (it) |
| CH (1) | CH534670A (it) |
| DE (1) | DE2139477A1 (it) |
| GB (1) | GB1358095A (it) |
| HU (1) | HU166904B (it) |
| IT (1) | IT941650B (it) |
| LU (1) | LU63662A1 (it) |
| NL (1) | NL170281B (it) |
| NO (1) | NO135635C (it) |
| RO (1) | RO62196A (it) |
| SE (1) | SE382631B (it) |
| YU (1) | YU35756B (it) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4178307A (en) | 1970-08-07 | 1979-12-11 | Ato Chimie | Process for preparing sulphonic acids and sulphonates |
| US4177208A (en) * | 1970-08-07 | 1979-12-04 | Ato Chemie | Process for preparing sulphonic acids and sulphonates |
| SU621675A1 (ru) * | 1976-04-05 | 1978-08-30 | Предприятие П/Я В-2287 | Способ получени щелочных солей алкилсульфокислот |
| GB1588363A (en) * | 1976-10-13 | 1981-04-23 | Ato Chimie | Process for preparing paraffin sulphonic acids and sulphonates |
| FR2413366A1 (fr) * | 1977-12-28 | 1979-07-27 | Ato Chimie | Separation des acides sulfoniques du milieu de leur preparation |
| DE3013808C2 (de) * | 1980-04-10 | 1982-12-23 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Abtennung von Schwefelsäure aus dem bei der Umsetzung von Paraffinen mit Schwefeldioxid, Sauerstoff und Wasser in Gegenwart von UV-Licht anfallenden Sulfoxidationsaustrag |
| DE3048058C2 (de) * | 1980-12-19 | 1983-04-28 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Abtrennung von Schwefelsäure aus dem bei der Sulfoxidation von n-Paraffinen anfallenden rohen Sulfonierungsgemisch |
| DE3203440A1 (de) * | 1982-02-02 | 1983-08-11 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur trennung von gemischen aus paraffin bzw. paraffinen mit 6 bis 14 c-atomen und alkohol bzw. alkoholen mit 4 bis 8 c-atomen |
| DE3210573A1 (de) * | 1982-03-23 | 1983-10-06 | Hoechst Ag | Verfahren zum abtrennen von schwefelsaeure aus dem bei der sulfoxidation von paraffinen anfallenden reaktionsgemisch |
| DE3304017A1 (de) * | 1983-02-07 | 1984-08-09 | Hoechst Ag, 6230 Frankfurt | Verfahren zur isolierung von paraffinsulfonat aus dem bei der sulfoxydation von paraffinen erhaltenen reaktionsgemisch |
| DE3325517A1 (de) * | 1983-07-15 | 1985-01-24 | Hoechst Ag, 6230 Frankfurt | Verfahren zur schonenden isolierung von paraffinsulfonsaeuren oder paraffinsulfonaten aus den bei der sulfoxidation von paraffinen erhaltenen reaktionsgemischen |
| DE3325516A1 (de) * | 1983-07-15 | 1985-01-24 | Hoechst Ag, 6230 Frankfurt | Verfahren zur schonenden isolierung von paraffinsulfonat und schwefelsaeure aus paraffin-sulfoxidations-reaktionsgemischen |
| DE3342984A1 (de) * | 1983-11-28 | 1985-06-05 | Hoechst Ag, 6230 Frankfurt | Verfahren zur isolierung von alkalisulfat-armen paraffinsulfonaten und schwefelsaeure aus paraffin-sulfoxidation-reaktionsgemischen |
| DE3639464A1 (de) * | 1986-11-18 | 1988-05-19 | Hoechst Ag | Verfahren zur isolierung von alkalisulfat-armen paraffinsulfonaten und schwefelsaeure aus paraffin-sulfoxidation-reaktionsgemischen ohne zwangsanfall von natriumsulfat |
| DE3718314A1 (de) * | 1987-06-01 | 1988-12-22 | Basf Ag | Verfahren zur isolierung von aromatischen sulfonsaeuren aus waessriger loesung oder suspension |
| DE102007020697A1 (de) | 2007-05-03 | 2008-11-06 | Clariant International Ltd. | Verfahren zur Isolierung konzentrierter Paraffinsulfonsäuren |
| DE102014009835B4 (de) | 2014-07-03 | 2020-12-24 | Weylchem Wiesbaden Gmbh | Verfahren zur Herstellung sekundärer Natrium-Alkansulfonate |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE540514C (de) * | 1930-03-11 | 1932-08-17 | Flintkote Co | Verfahren zur Herstellung von gereinigten Sulfonsaeuren oder ihren Salzen |
| DE640681C (de) * | 1931-05-19 | 1937-01-09 | Rudolf & Co | Verfahren zur Gewinnung von gereinigten Schwefelsaeureestern der Fett- und Wachsalkohole |
| DE827065C (de) * | 1948-11-19 | 1952-01-07 | Aug Luhn & Co Ges M B H | Verfahren zur Reinigung und Konzentration von synthetischen Sulfonaten hochmolekularer aliphatischer Kohlenwasserstoffe |
| FR1478530A (fr) * | 1966-03-11 | 1967-04-28 | Exxon Standard Sa | Nouveau procédé d'élimination de l'acide sulfurique des acides sulfoniques |
| 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 |
-
1971
- 1971-08-03 CH CH1142271A patent/CH534670A/fr not_active IP Right Cessation
- 1971-08-03 BG BG18229A patent/BG20344A3/xx unknown
- 1971-08-03 YU YU2016/71A patent/YU35756B/xx unknown
- 1971-08-03 IT IT27087/71A patent/IT941650B/it active
- 1971-08-04 HU HUPE788A patent/HU166904B/hu unknown
- 1971-08-04 LU LU63662D patent/LU63662A1/xx unknown
- 1971-08-05 SE SE7110050A patent/SE382631B/xx unknown
- 1971-08-05 NO NO2945/71A patent/NO135635C/no unknown
- 1971-08-06 BE BE771038A patent/BE771038A/xx not_active IP Right Cessation
- 1971-08-06 CA CA120,040*7A patent/CA952122A/en not_active Expired
- 1971-08-06 GB GB3707571A patent/GB1358095A/en not_active Expired
- 1971-08-06 DE DE19712139477 patent/DE2139477A1/de active Granted
- 1971-08-06 NL NLAANVRAGE7110917,A patent/NL170281B/xx not_active Application Discontinuation
- 1971-08-07 RO RO67930A patent/RO62196A/ro unknown
- 1971-08-07 JP JP46059871A patent/JPS505689B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL170281B (nl) | 1982-05-17 |
| NO135635C (it) | 1977-05-04 |
| CH534670A (fr) | 1973-03-15 |
| JPS505689B1 (it) | 1975-03-06 |
| LU63662A1 (it) | 1971-12-13 |
| IT941650B (it) | 1973-03-10 |
| BG20344A3 (it) | 1975-11-05 |
| YU35756B (en) | 1981-06-30 |
| YU201671A (en) | 1980-12-31 |
| NL7110917A (it) | 1972-02-09 |
| DE2139477C2 (it) | 1987-06-04 |
| RO62196A (it) | 1977-06-15 |
| BE771038A (fr) | 1971-12-16 |
| SE382631B (sv) | 1976-02-09 |
| CA952122A (en) | 1974-07-30 |
| DE2139477A1 (de) | 1972-02-10 |
| GB1358095A (en) | 1974-06-26 |
| HU166904B (it) | 1975-06-28 |
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