DE4220580A1 - New alpha-sulpho carbonyl cpds. useful as surfactants - prepd. by sulphonating higher aldehyde or ketone with sulphur tri:oxide - Google Patents
New alpha-sulpho carbonyl cpds. useful as surfactants - prepd. by sulphonating higher aldehyde or ketone with sulphur tri:oxideInfo
- Publication number
- DE4220580A1 DE4220580A1 DE4220580A DE4220580A DE4220580A1 DE 4220580 A1 DE4220580 A1 DE 4220580A1 DE 4220580 A DE4220580 A DE 4220580A DE 4220580 A DE4220580 A DE 4220580A DE 4220580 A1 DE4220580 A1 DE 4220580A1
- Authority
- DE
- Germany
- Prior art keywords
- fatty
- carbon atoms
- alpha
- ketone
- ketones
- 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.)
- Withdrawn
Links
- 150000002576 ketones Chemical class 0.000 title claims abstract description 27
- 150000001299 aldehydes Chemical class 0.000 title abstract description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 title abstract description 3
- 239000004094 surface-active agent Substances 0.000 title description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title 1
- 239000005864 Sulphur Substances 0.000 title 1
- 239000002585 base Substances 0.000 claims abstract description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 7
- 239000000194 fatty acid Substances 0.000 claims abstract description 7
- 229930195729 fatty acid Natural products 0.000 claims abstract description 7
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 7
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 3
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 3
- 239000011552 falling film Substances 0.000 claims abstract description 3
- 238000000197 pyrolysis Methods 0.000 claims abstract description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 28
- 239000000047 product Substances 0.000 claims description 12
- 150000002192 fatty aldehydes Chemical class 0.000 claims description 11
- 238000006277 sulfonation reaction Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- 239000003945 anionic surfactant Substances 0.000 abstract description 6
- -1 fatty acid alkaline earth metal salt Chemical class 0.000 abstract description 4
- 239000003599 detergent Substances 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 abstract description 2
- 238000009736 wetting Methods 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 1
- 238000004945 emulsification Methods 0.000 abstract 1
- 238000005187 foaming Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 239000000243 solution Substances 0.000 description 7
- PQYGSSYFJIJDFK-UHFFFAOYSA-N heptyl ketone Chemical compound CCCCCCCC(=O)CCCCCCC PQYGSSYFJIJDFK-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 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
- 239000013543 active substance Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- FWWQKRXKHIRPJY-UHFFFAOYSA-N octadecanal Chemical compound CCCCCCCCCCCCCCCCCC=O FWWQKRXKHIRPJY-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- DMCJFWXGXUEHFD-UHFFFAOYSA-N pentatriacontan-18-one Chemical compound CCCCCCCCCCCCCCCCCC(=O)CCCCCCCCCCCCCCCCC DMCJFWXGXUEHFD-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 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
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000006280 Rosenmund reaction Methods 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- ULCXRAFXRZTNRO-UHFFFAOYSA-N docosanal Chemical compound CCCCCCCCCCCCCCCCCCCCCC=O ULCXRAFXRZTNRO-UHFFFAOYSA-N 0.000 description 1
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- NIOYUNMRJMEDGI-UHFFFAOYSA-N hexadecanal Chemical compound CCCCCCCCCCCCCCCC=O NIOYUNMRJMEDGI-UHFFFAOYSA-N 0.000 description 1
- 229960002163 hydrogen peroxide Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229940089454 lauryl aldehyde Drugs 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- UHUFTBALEZWWIH-UHFFFAOYSA-N tetradecanal Chemical compound CCCCCCCCCCCCCC=O UHUFTBALEZWWIH-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/08—Sulfation or sulfonation products of fats, oils, waxes, or higher fatty acids or esters thereof with monovalent alcohols
-
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Die Erfindung betrifft alpha-Sulfocarbonylverbindungen, ein Verfahren zu ihrer Herstellung durch Sulfonierung von Fett ketonen bzw. Fettaldehyden und nachfolgende Neutralisation sowie ihre Verwendung zur Herstellung oberflächenaktiver Mittel.The invention relates to alpha-sulfocarbonyl compounds, a Process for their preparation by sulfonation of fat ketones or fatty aldehydes and subsequent neutralization as well as their use for the production of surface-active Medium.
Aus der Deutschen Offenlegungsschrift DE-A-25 53 990 ist be kannt, daß langkettige Dialkyl- bzw. Dialkenylketone (Fett ketone) ausgezeichnete schaumdämpfende Eigenschaften aufwei sen. Von Nachteil ist bei dieser Gruppe von Substanzen jedoch ihre geringe Wasserlöslichkeit.From the German patent application DE-A-25 53 990 is be it is known that long-chain dialkyl or dialkenyl ketones (fat ketone) excellent foam-damping properties sen. However, this group of substances is disadvantageous their low water solubility.
Aus der Europäischen Offenlegungsschrift EP-A-0 358 097 (Hen kel) sind innenständige Sulfofettketone mit verbesserter Wasserlöslichkeit bekannt, die man durch Anlagerung von Schwefeltrioxid an die Doppelbindung von ungesättigten Fett ketonen erhält. Da die Ausgangsstoffe jedoch nur schwer zugänglich sind, stehen die Produkte für eine technische Nutzung nur eingeschränkt zur Verfügung.From European Patent Application EP-A-0 358 097 (Hen kel) are internal sulfofatty ketones with improved Water solubility known, which is obtained by addition of Sulfur trioxide to the double bond of unsaturated fat ketones. However, the starting materials are difficult are accessible, the products stand for a technical Use only limited available.
Gegenstand der Erfindung sind alpha-Sulfocarbonylverbin dungen, die man dadurch erhält, indem man Fettketone bzw. Fettaldehyde, die bei Temperaturen unterhalb von 90°C flüssig sind und der Formel (I) folgen,The invention relates to alpha-Sulfocarbonylverbin tions obtained by adding fatty ketones or Fatty aldehydes, which are liquid at temperatures below 90 ° C are and follow the formula (I),
R¹-CO-R² (I)R¹-CO-R² (I)
in der
R1 für einen Alkylrest mit 5 bis 22 Kohlenstoffatomen und
R2 für Wasserstoff oder einen Alkylrest mit 5 bis 22 Koh
lenstoffatomen
steht, mit gasförmigem Schwefeltrioxid umsetzt und die sauren
Reaktionsprodukte anschließend mit wäßrigen Basen neutrali
siert.in the
R 1 is an alkyl radical having 5 to 22 carbon atoms and
R 2 is hydrogen or an alkyl radical having 5 to 22 carbon atoms
is reacted with gaseous sulfur trioxide and the acidic reaction products then Siert neutralized with aqueous bases.
Überraschenderweise wurde gefunden, daß auch leicht zugäng liche gesättigte Carbonylverbindungen, wie Fettketone und Fettaldehyde, einer Sulfonierung zugänglich sind, wobei was serlösliche Produkte erhalten werden, die sich durch minde stens eine Sulfonatgruppe in alpha-Stellung zur Carbonyl gruppe auszeichnen. Surprisingly, it was found that easily accessible saturated saturated carbonyl compounds, such as fatty ketones and Fettaldehyde, a sulfonation accessible, wherein what serlösliche products are obtained, which by minde at least one sulfonate group in the alpha position to the carbonyl distinguished group.
Ein weiterer Gegenstand der Erfindung betrifft ein Verfahren zur Herstellung von alpha-Sulfocarbonylverbindungen, bei dem man Fettketone bzw. Fettaldehyde, die bei Temperaturen unter halb von 90°C flüssig sind und der Formel (I) folgen,Another object of the invention relates to a method for the preparation of alpha-sulfocarbonyl compounds in which fatty ketones or fatty aldehydes which are at temperatures below are half of 90 ° C liquid and the formula (I) follow,
R¹-CO-R² (I)R¹-CO-R² (I)
in der
R1 für einen Alkylrest mit 5 bis 22 Kohlenstoffatomen und
R2 für Wasserstoff oder einen Alkylrest mit 5 bis 22 Koh
lenstoffatomen
steht, mit gasförmigem Schwefeltrioxid umsetzt und die sauren
Reaktionsprodukte anschließend mit wäßrigen Basen neutrali
siert.in the
R 1 is an alkyl radical having 5 to 22 carbon atoms and
R 2 is hydrogen or an alkyl radical having 5 to 22 carbon atoms
is reacted with gaseous sulfur trioxide and the acidic reaction products then Siert neutralized with aqueous bases.
Fettketone stellen bekannte Stoffe dar, die nach den ein schlägigen Methoden der präparativen organischen Chemie er halten werden können. Die Fettketone können offenkettig oder cyclisch sein; vorzugsweise werden solche Stoffe eingesetzt, die man durch Pyrolyse der Erdalkalisalze von gesättigten Fettsäuren mit 6 bis 22 Kohlenstoffatomen erhält [vgl. DE-A- 25 53 990 und DE-B-27 58 113]. Fettsäuren der hier angespro chenen Art sind beispielsweise Capronsäure, Caprylsäure, Caprinsäure, Laurinsäure, Myristinsäure, Palmitinsäure, Stearinsäure, Isostearinsäure, Arachinsäure, und Behensäure sowie deren technische Schnitte, wie sie beispielsweise bei der Spaltung von natürlichen Fetten und Ölen anfallen. Dem entsprechend können die den Fettketonen zugrundeliegenden Fettsäuren auch ungesättigte Anteile enthalten, sofern diese einen Gehalt von 50 Gew.-% nicht übersteigen. Für die Her stellung der erfindungsgemäßen alpha-Sulfocarbonylverbin dungen kommen vorzugsweise Caprylon (Pentadecanon-8) und Stearon in Betracht.Grease ketones are known substances, which according to the one pertinent methods of preparative organic chemistry he can be kept. The fatty ketones can be open-chain or be cyclic; preferably such substances are used which is obtained by pyrolysis of the alkaline earth salts of saturated Fatty acids having 6 to 22 carbon atoms [cf. DE-A- 25 53 990 and DE-B-27 58 113]. Fatty acids here angepro are, for example, caproic acid, caprylic acid, Capric acid, lauric acid, myristic acid, palmitic acid, Stearic acid, isostearic acid, arachidic acid, and behenic acid as well as their technical sections, as for example in the splitting of natural fats and oils. the Accordingly, the underlying the fatty ketones Fatty acids also contain unsaturated components, if these do not exceed a content of 50 wt .-%. For the Her position of the alpha-Sulfocarbonylverbin invention preferably Caprylon (pentadecanone-8) and Stearon into consideration.
Fettaldehyde stellen ebenfalls bekannte Stoffe dar, zu deren Herstellung man beispielsweise von Fettalkoholen ausgeht, die mit Hypochlorit, Persäuren oder Luft in Gegenwart von Kataly satoren oxidiert werden. Ein weiteres bekanntes Verfahren stellt die Rosenmund-Reaktion dar, bei der man Fettsäurechlo ride in Gegenwart von Lindlar-Katalysatoren zu den entspre chenden Aldehyden reduziert [vgl. J. Am. Chem. Soc. 109, 3786 (1987), J. Org. Chem. 52, 2259 (1987), Tetrahedr. Lett., 28, 4575 (1987)]. Fettaldehyde, die als Einsatzstoffe zur Her stellung der erfindungsgemäßen alpha-Sulfocarbonylver bindungen in Betracht kommen, sind beispielsweise Capronal dehyd, Caprinaldehyd, Laurylaldehyd, Myristylaldehyd, Cetyl aldehyd, Isostearylaldehyd, Stearylaldehyd, Arachylaldehyd und Behenylaldehyd sowie wiederum deren technische Gemische.Fettaldehyde also represent known substances to whose For example, starting from fatty alcohols starting, the with hypochlorite, peracids or air in the presence of catalysis oxidized. Another known method represents the Rosenmund reaction in which fatty acid is used ride in the presence of Lindlar catalysts to the entspre reduced aldehydes [cf. J. Am. Chem. Soc. 109, 3786 (1987), J. Org. Chem. 52, 2259 (1987), Tetrahedr. Lett., 28, 4575 (1987)]. Fettaldehyde, which are used as starting materials for Her position of the alpha-Sulfocarbonylver invention compounds are for example Capronal dehyd, capric aldehyde, lauryl aldehyde, myristyl aldehyde, cetyl aldehyde, isostearyl aldehyde, stearyl aldehyde, arachyl aldehyde and behenylaldehyde and again their technical mixtures.
Die Sulfonierung der Fettketone bzw. Aldehyde mit gasförmigem Schwefeltrioxid kann in der für Fettsäure-niedrigalkylester bekannten Weise [J.Falbe (ed.), "Surfactants in consumer products", Springer Verlag, Berlin-Heidelberg, 1987, S. 61] erfolgen, wobei kontinuierliche Reaktoren, die nach dem Fall filmprinzip arbeiten, bevorzugt sind. Hierbei wird das Schwefeltrioxid mit einem inerten Gas, vorzugsweise Luft oder Stickstoff verdünnt und in Form eines Gasgemisches, welches das Sulfieragens in einer Konzentration von 1 bis 8, insbe sondere 2 bis 5 Vol.-% enthält, eingesetzt. The sulfonation of fatty ketones or aldehydes with gaseous Sulfur trioxide may be used in fatty acid lower alkyl esters known manner [J.Falbe (ed.), "Surfactants in consumer products ", Springer Verlag, Berlin-Heidelberg, 1987, p. 61] done, taking continuous reactors after the fall working principle, are preferred. Here is the Sulfur trioxide with an inert gas, preferably air or Nitrogen diluted and in the form of a gas mixture, which the sulfating agent in a concentration of 1 to 8, esp special contains 2 to 5 vol .-%, used.
Die Fettketone bzw. Fettaldehyde und das Schwefeltrioxid kön nen im molaren Verhältnis von 1 : 0,1 bis 1 : 2,4, vorzugs weise 1 : 1 bis 1 : 1,2 eingesetzt werden. Die Wahl eines hohen SO3-Überschusses bevorteilt naturgemäß die Bildung von Disulfonaten und macht nur bei Einsatz von Fettketonen Sinn. Da Fettaldehyde einer Doppelsulfonierung nicht zugänglich sind, ist es hier vorteilhaft, den molaren SO3-Überschuß auf maximal 20% zu begrenzen.The fatty ketones or fatty aldehydes and the sulfur trioxide Kings nen in a molar ratio of 1: 0.1 to 1: 2.4, preferably, 1: 1 to 1: 1.2 are used. The choice of a high SO 3 excess naturally promotes the formation of disulfonates and makes sense only when using fatty ketones. Since fatty aldehydes are not accessible to a double sulfonation, it is advantageous here to limit the molar SO 3 excess to a maximum of 20%.
Die Reaktionstemperatur kann 40 bis 98°C betragen. Als be sonders vorteilhaft hat es sich ferner erwiesen, die Sulfo nierung 10 bis 20°C oberhalb des Schmelzpunktes des Fettke tons bzw. Fettaldehyds durchzuführen.The reaction temperature may be 40 to 98 ° C. As be It has also proved to be particularly advantageous to use the sulfo 10-20 ° C above the melting point of the fatty acid tons or fatty aldehyde.
Die bei der Sulfonierung anfallenden sauren Sulfierprodukte werden in wäßrige Basen eingerührt, neutralisiert und auf einen pH-Wert von 7 bis 9 eingestellt. Als Basen für die Neutralisation kommen Alkalimetallhydroxide wie Natrium-, Kalium- und Lithiumhydroxid, Erdalkalimetalloxide und -hy droxide wie Magnesiumoxid, Magnesiumhydroxid, Calciumoxid und Calciumhydroxid, Ammoniak, Mono-, Di- und Tri-C2-4-Alkanol amine, beispielsweise Mono-, Di- und Triethanolamin sowie primäre, sekundäre oder tertiäre C1-4-Alkylamine in Betracht. Die Neutralisationsbasen gelangen dabei vorzugsweise in Form 5 bis 55 gew.-%iger wäßriger Lösungen zum Einsatz, wobei 5 bis 25 gew.-%ige wäßrige Natriumhydroxidlösungen bevorzugt sind.The obtained during the sulfonation acid sulfonation are stirred into aqueous bases, neutralized and adjusted to a pH of 7 to 9. Suitable bases for the neutralization are alkali metal hydroxides such as sodium, potassium and lithium hydroxide, alkaline earth metal oxides and hydroxides such as magnesium oxide, magnesium hydroxide, calcium oxide and calcium hydroxide, ammonia, mono-, di- and tri-C 2-4 -alkanolamines, for example mono , Di- and triethanolamine and primary, secondary or tertiary C 1-4 alkyl amines into consideration. The neutralization bases are preferably used in the form of 5 to 55% strength by weight aqueous solutions, with 5 to 25% strength by weight aqueous sodium hydroxide solutions being preferred.
Ausgehend von Fettketonen werden alpha-Sulfocarbonylver bindungen erhalten, die Gemische von Mono- und Disulfonaten darstellen und deren Zusammensetzung weitgehend durch die Menge des eingesetzten Schwefeltrioxids beeinflußt wird; alpha-Sulfocarbonylverbindungen auf Basis von Fettaldehyden stellen hingegen naturgemäß Monosulfonate dar. Sind in den Ausgangsprodukten - Fettketonen oder Fettaldehyden - noch Doppelbindungsanteile enthalten, können die sulfonierten Endprodukte Komponenten mit innenständigen Sulfonatgruppen als Verunreinigungen enthalten.Starting from fatty ketones, alpha-sulfocarbonyl ver get bonds, the mixtures of mono- and disulfonates and their composition largely by the Amount of sulfur trioxide used is affected; alpha-sulfocarbonyl compounds based on fatty aldehydes By contrast, naturally represent monosulfonates. Are in the Starting products - fatty ketones or fatty aldehydes - still Containing double bond moieties may be the sulfonated ones End products Components with internal sulfonate groups Contain as impurities.
Die alpha-Sulfocarbonylverbindungen können nach der Neutra lisation in an sich bekannter Weise durch Zusatz von Wasser stoffperoxid- oder Natriumhypochloritlösung gebleicht werden. Dabei werden - bezogen auf den Feststoffgehalt in der Lösung der Sulfonierungsprodukte - 0,2 bis 2 Gew.-% Wasserstoffper oxid, berechnet als 100%ige Substanz, oder entsprechende Mengen Natriumhypochlorit eingesetzt. Der pH-Wert der Lö sungen kann unter Verwendung geeigneter Puffermittel, z. B. mit Natriumphosphat oder Citronensäure konstant gehalten werden. Zur Stabilisierung gegen Bakterienbefall empfiehlt sich ferner eine Konservierung, z. B. mit Formaldehydlösung, p-Hydroxybenzoat, Sorbinsäure oder anderen bekannten Konser vierungsstoffen. Des weiteren kann es empfehlenswert sein, die Lösungen nach Neutralisation und ggf. Bleiche zu fil trieren, um nichtumgesetztes Ausgangsmaterial, insbesondere Fettketone, abzutrennen und in die Reaktion zurückzuführen. The alpha-sulfocarbonyl compounds can after the Neutra lisation in a conventional manner by the addition of water bleached peroxide or sodium hypochlorite solution. Here are - based on the solids content in the solution the sulfonation products - 0.2 to 2 wt .-% hydrogen per oxide, calculated as 100% substance, or equivalent Amounts of sodium hypochlorite used. The pH of the Lö solutions may be prepared using suitable buffering agents, e.g. B. kept constant with sodium phosphate or citric acid become. To stabilize against bacterial attack recommends Furthermore, a preservation, for. With formaldehyde solution, p-hydroxybenzoate, sorbic acid or other known conser vierungsstoffen. Furthermore, it may be advisable the solutions after neutralization and possibly bleaching to fil to unreacted starting material, in particular Grease ketones, separate and due to the reaction.
Die erfindungsgemäßen alpha-Sulfocarbonylverbindungen besit zen oberflächenaktive Eigenschaften, dämpfen die Schaument wicklung anionischer Tenside in wäßrigen Systemen, fördern das Benetzen fester Oberflächen und die Emulgierung von Öl und Wasser.The alpha-sulfocarbonyl compounds according to the invention have zen surface-active properties, dampen the foam development of anionic surfactants in aqueous systems wetting solid surfaces and emulsifying oil and water.
Ein weiterer Gegenstand der Erfindung betrifft daher die Ver wendung der erfindungsgemäßen alpha-Sulfocarbonylverbindungen zur Herstellung von Wasch-, Spül- und Reinigungsmitteln sowie Produkten zur Haar- und Körperpflege, in denen sie in Mengen von 1 bis 50, vorzugsweise 10 bis 30 Gew.-% - bezogen auf die Mittel - enthalten sein können.Another object of the invention therefore relates to the Ver Use of the alpha-sulfocarbonyl compounds of the invention for the production of detergents, dishwashing detergents and cleaning agents as well Hair and body care products in quantities from 1 to 50, preferably 10 to 30 wt .-% - based on the Means - may be included.
Die folgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn darauf einzuschränken.The following examples are intended to form the subject of the invention explain it in more detail without restricting it to it.
In einem 0,5-l-Sulfierreaktor mit Gaseinleitungsrohr und Mantelkühlung wurden 113,2 g (0,5 mol) Pentadecanon-8 (Caprylon) vorgelegt und bei 60°C mit 44 g (0,55 mol) gasförmigem Schwefeltrioxid umgesetzt. Das SO3 war zuvor aus einer ent sprechenden Menge 65 gew.-%igen Oleums ausgetrieben und mit Stickstoff auf eine Konzentration von 5 Vol.-% verdünnt wor den. Die vom Fettketon aufgenommene Menge des Schwefeltri oxids betrug 86%. Das saure Sulfierprodukt wurde anschlie ßend mit 25 gew.-%iger wäßriger Natriumhydroxidlösung neu tralisiert, auf einen pH-Wert von 8 eingestellt und über eine Nutsche filtriert, wobei nichtumgesetztes Caprylon zurückge wonnen werden konnte.113.2 g (0.5 mol) of pentadecanone-8 (caprylon) were introduced into a 0.5 l sulfonation reactor with gas inlet tube and jacket cooling and reacted at 60 ° C. with 44 g (0.55 mol) of gaseous sulfur trioxide. The SO 3 was previously expelled from a ent speaking amount of 65 wt .-% oleum and diluted with nitrogen to a concentration of 5 vol .-% diluted to the. The amount of sulfur trioxide taken up by the fatty ketone was 86%. The acid sulfonation product was subsequently re-crystallized with 25% by weight aqueous sodium hydroxide solution, adjusted to pH 8, and filtered through a suction filter to recover unreacted caprylon.
In einem kontinuierlich arbeitenden Fallfilmreaktor (Länge 120 cm, Querschnitt 1 cm, Eduktdurchsatz 600 g/h) mit Mantel kühlung und seitlicher SO3-Begasung wurden 5.0 mol Caprylon bei 60°C mit 6 mol gasförmigem Schwefeltrioxid zur Reaktion gebracht. Das saure Reaktionsgemisch wurde dabei kontinuier lich in 10 gew.-%ige wäßrige Natriumhydroxidlösung eingetra gen, neutralisiert und auf pH = 8 eingestellt. Anschließend wurde das Produkt über eine Nutsche filtriert und nichtum gesetztes Caprylon abgetrennt.In a continuous falling film reactor (length 120 cm, cross section 1 cm, Eduktdurchsatz 600 g / h) with jacket cooling and lateral SO 3 gassing 5.0 mol Caprylon were reacted at 60 ° C with 6 moles of gaseous sulfur trioxide. The acidic reaction mixture was continuously introduced into 10% strength by weight aqueous sodium hydroxide solution, neutralized and adjusted to pH = 8. The product was then filtered through a suction filter and separated Caprylon not set.
Beispiel 1 wurde unter Einsatz von 93 g (0,5 mol) Laurylal dehyd und 44 g Schwefeltrioxid wiederholt. Eine Filtration wurde nicht durchgeführt.Example 1 was carried out using 93 g (0.5 mol) of laurylal dehyd and 44 g of sulfur trioxide. A filtration was not accomplished.
Der Aniontensidgehalt (WAS) sowie die Unsulfierten Anteile (US) wurden nach den DGF-Einheitsmethoden, Stuttgart 1950- 1984, H-III-10 und G-II-6b ermittelt.The anionic surfactant content (WAS) and the unsulfonated fractions (US) according to the DGF standard methods, Stuttgart 1950- 1984, H-III-10 and G-II-6b determined.
Claims (8)
R1 für einen Alkylrest mit 5 bis 22 Kohlenstoffatomen und
R2 für Wasserstoff oder einen Alkylrest mit 5 bis 22 Kohlenstoffatomen
steht, mit gasförmigem Schwefeltrioxid umsetzt und die sauren Reaktionsprodukte anschließend mit wäßrigen Basen neutralisiert.1. Alpha-sulfocarbonyl compounds, obtainable by adding fatty ketones or fatty aldehydes, which are liquid at temperatures below 90 ° C and the formula (I), R¹-CO-R² (I) in the
R 1 is an alkyl radical having 5 to 22 carbon atoms and
R 2 is hydrogen or an alkyl radical having 5 to 22 carbon atoms
is reacted with gaseous sulfur trioxide and the acidic reaction products are then neutralized with aqueous bases.
R1 für einen Alkylrest mit 5 bis 22 Kohlenstoffatomen und
R2 für Wasserstoff oder einen Alkylrest mit 5 bis 22 Kohlenstoffatomen
steht, mit gasförmigem Schwefeltrioxid umsetzt und die sauren Reaktionsprodukte anschließend mit wäßrigen Basen neutralisiert.2. A process for the preparation of alpha-Sulfocarbonylver compounds, in which fatty ketones or fatty aldehydes, which are liquid at temperatures below 90 ° C and the formula (I) follow, R¹-CO-R² (I) in the
R 1 is an alkyl radical having 5 to 22 carbon atoms and
R 2 is hydrogen or an alkyl radical having 5 to 22 carbon atoms
is reacted with gaseous sulfur trioxide and the acidic reaction products are then neutralized with aqueous bases.
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|---|---|---|---|
| DE4220580A DE4220580A1 (en) | 1992-06-24 | 1992-06-24 | New alpha-sulpho carbonyl cpds. useful as surfactants - prepd. by sulphonating higher aldehyde or ketone with sulphur tri:oxide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4220580A DE4220580A1 (en) | 1992-06-24 | 1992-06-24 | New alpha-sulpho carbonyl cpds. useful as surfactants - prepd. by sulphonating higher aldehyde or ketone with sulphur tri:oxide |
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| DE4220580A Withdrawn DE4220580A1 (en) | 1992-06-24 | 1992-06-24 | New alpha-sulpho carbonyl cpds. useful as surfactants - prepd. by sulphonating higher aldehyde or ketone with sulphur tri:oxide |
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| WO2018015036A1 (en) * | 2016-07-19 | 2018-01-25 | Basf Se | Aqueous surfactant compositions |
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| RU2798909C2 (en) * | 2018-07-09 | 2023-06-28 | Родиа Операсьон | Compositions based on sulfonated internal ketones for increasing oil recovery |
| CN112567002B (en) * | 2018-07-09 | 2023-09-08 | 罗地亚经营管理公司 | Sulfonated endo-ketone based formulation for assisting oil recovery |
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