US1968797A - Sulphuric derivative of higher alcohols - Google Patents
Sulphuric derivative of higher alcohols Download PDFInfo
- Publication number
- US1968797A US1968797A US650203A US65020333A US1968797A US 1968797 A US1968797 A US 1968797A US 650203 A US650203 A US 650203A US 65020333 A US65020333 A US 65020333A US 1968797 A US1968797 A US 1968797A
- Authority
- US
- United States
- Prior art keywords
- alcohols
- alcohol
- fatty
- acid
- sulphuric
- 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 - Lifetime
Links
- 150000001298 alcohols Chemical class 0.000 title description 41
- 235000019441 ethanol Nutrition 0.000 description 57
- 235000014113 dietary fatty acids Nutrition 0.000 description 25
- 239000000194 fatty acid Substances 0.000 description 25
- 229930195729 fatty acid Natural products 0.000 description 25
- 235000011149 sulphuric acid Nutrition 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 20
- 150000004665 fatty acids Chemical class 0.000 description 20
- 239000000463 material Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 239000001117 sulphuric acid Substances 0.000 description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 17
- -1 sulphuric acid ester Chemical class 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000003921 oil Substances 0.000 description 11
- 230000009467 reduction Effects 0.000 description 11
- 238000006722 reduction reaction Methods 0.000 description 11
- 238000009736 wetting Methods 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 239000003599 detergent Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 229910001868 water Inorganic materials 0.000 description 9
- 239000003240 coconut oil Substances 0.000 description 8
- 235000019864 coconut oil Nutrition 0.000 description 8
- 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 7
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 7
- 150000002191 fatty alcohols Chemical class 0.000 description 7
- 235000021588 free fatty acids Nutrition 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000080 wetting agent Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 6
- 150000003138 primary alcohols Chemical class 0.000 description 6
- 239000003760 tallow Substances 0.000 description 6
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 6
- 239000004753 textile Substances 0.000 description 6
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 5
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
- 239000003346 palm kernel oil Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 235000019865 palm kernel oil Nutrition 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 239000008233 hard water Substances 0.000 description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 3
- 229960003656 ricinoleic acid Drugs 0.000 description 3
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 3
- 239000012177 spermaceti Substances 0.000 description 3
- 229940084106 spermaceti Drugs 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 2
- 229940093471 ethyl oleate Drugs 0.000 description 2
- 239000010685 fatty oil Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000004426 flaxseed Nutrition 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229940043348 myristyl alcohol Drugs 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 125000000075 primary alcohol group Chemical group 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 1
- SXNBVULTHKFMNO-UHFFFAOYSA-N 2,2-dihydroxyoctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)(O)C(O)=O SXNBVULTHKFMNO-UHFFFAOYSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000969130 Atthis Species 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000010981 drying operation Methods 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
- 238000001914 filtration Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D1/00—Fire-extinguishing compositions; Use of chemical substances in extinguishing fires
- A62D1/0071—Foams
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B26—HAND CUTTING TOOLS; CUTTING; SEVERING
- B26D—CUTTING; DETAILS COMMON TO MACHINES FOR PERFORATING, PUNCHING, CUTTING-OUT, STAMPING-OUT OR SEVERING
- B26D7/00—Details of apparatus for cutting, cutting-out, stamping-out, punching, perforating, or severing by means other than cutting
- B26D7/06—Arrangements for feeding or delivering work of other than sheet, web, or filamentary form
-
- 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
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
Definitions
- This invention relates to soap-like products and to the manufacture of soaps, detergents, and the like, and to improvements in treatment liquids for use in the textile, leather, and allied industries. It is the primary object of the invention to produce new soap-like materials and other substances of this character having greater wetting, cleansing, dispersing, and foaming properties than the agents heretofore used.
- Water-soluble sulphuric esters produced by the action of sulphuric acid on fatty materials are widely employed as wetting, cleansing, and dispersing agents in the textile and related industries.
- a sulphuric acid ester of the hydroxy stearic acid may be produced by treating oleic acid with sulphuric acid, and a sulphuric acid ester of a dihydroxy stearic acid may be obtained by the treatment of ricinoleic acid with sulphuric acid.
- this defect is in large measure avoided if, instead of fatty acids or the esters of these acids, the corresponding alcohols obtained therefrom by replacement in effect of the carboxyl group whether free or combined with the CHzOH group are treated with sulphuric acid or with other sulphating or sulphonating agent.
- Commercial fats are essentially mixed glycerides of the various higher fatty acids, and the higher alcohols 0btainable therefrom are mixtures of alcohols of the general formula CxHyCH2OH.
- mixtures consist predominantly of alcohols having 10 or more carbon atoms per molecule, correspending to the molecular weight of the fatty acids, free or combined, contained in the natural fats and fatty oils and the other commercially available fatty materials derived therefrom.
- foaming agents can be obtained by treating such alcohols with sulphuric acid or with other sulphating or sulphonating agent.
- These alcohols may be referred to collectively as normal primary alcohols having more than eight carbon atoms to the molecule.
- the invention contemplates the conversion of the free or combined fatty acids of fatty materials, i. e. animal and vegetable fats and oils, and manufactured derivatives such as oleic acid or ethyl oleate, into the corresponding alcohols, and the treatment of these alcohols with ,a sulphating or sulphonating agent such as sulphuric acid.
- a sulphating or sulphonating agent such as sulphuric acid.
- a base for example sodium hydroxide or ammonia to form a water soluble soap-like salt, as is common practice in the case of sulphated fatty acids or sulphated fatty oils, such as Turkey red oil.
- the precise nature of the method selected to convert the fatty material to the alcohol may be varied.
- a well-known method is that of Bouveault and Blanc, in accordance with which an alkyl ester of a fatty acid, e. g. an ethyl oleate, is reduced by sodium or other alkali metal and a lower aliphatic alcohol such as butyl alcohol, or the improved method described in my application for Letters Patent Serial No. 472,764 may be used.
- Numerous processes are known for preparing the alkyl esters from fats and fatty acids.
- the Bouveault and Blanc process is of general application for the preparation of both unsaturated and saturated alcohols.
- oleic alcohol C17H33CH2OH
- esters of oleic acid CnHaaCOOH
- An octodecyl alcohol C1'1H35CH2OH
- esters oi stearic acid C11Ha5CO0H.
- Mixed saturated and unsaturated alcohols result when the unfractionated esters of the fatty acids of most natural fats, for example, tallow, are reduced according to the Bouveault and Blanc process.
- Fatty alcohols obtained from the source d scribed are next treated with a sulphating agent having water-binding properties.
- a sulphating agent having water-binding properties.
- Ordinary concentrated sulphuric acid may be used, or stronger reagents such as anhydrous sulphuric acid, 110
- the sulphated products of oleic alcohol are particularly resistant to hardness and are high- 1y suitable for use in the textile and related industries.
- the sulphuric reaction products derived from lauryl alcohol, especially the esters and salts thereof, are also found to be particularly effective in the textile industry.
- the fatty alcohols made from free fatty acids of the coconut oil or palm seed oil in a manner known per se by esterifying the fatty acids of the same with lower aliphatic alcohols and reducing the mixture of esters by means of sodium, it is advantageous to distill the reduction product and to use only the first 50% to 60% of the distillate.
- the product thus obtained consists mainly of lauryl alcohol, the somewhat less suitable higher fractions which contain principally myristyl alcohol and octodecyl alcohol being substantially eliminated. It should be understood, however, that the presence of the sulphuric derivatives of lower or higher alcohols, such as of myristyl alcohol with the lauryl alcohol derivatives does not materially decrease the efliciency of the final product.
- Alcohols obtained by catalytic hydrogenation of palm kernel oil or of the free fatty acids of palm kernel oil comprising similar constituents as the alcohols obtained from coconut oil.
- Alcohols obtained by saponiflcation of spermaceti, sperm oil, beeswax and distillation according to Axelrad and Hochstadter U. S. A. Patent 1,290,870
- Linoleic alcohol obtained by reduction of linoleic acid by means of sodium and ethyl alcohol.
- Alcohols obtained by catalytic reduction of tallow or the free fatty acids of tallow are obtained by catalytic reduction of tallow or the free fatty acids of tallow.
- Alcohols obtained by catalytic hydrogenation of the free fatty acids of coconut oil are obtained by catalytic hydrogenation of the free fatty acids of coconut oil.
- Alcohols obtained by reducing olive oil by means of metallic sodium and butyl alcohol obtained by reducing olive oil by means of metallic sodium and butyl alcohol.
- Alcohols obtained by catalytic hydrogenation of the ethyl ester of commercial stearic acid obtained by catalytic hydrogenation of the ethyl ester of commercial stearic acid.
- Ricinoleic alcohol obtained by reduction of ricinoleic acid by means of sodium and ethyl alcohol.
- Example 1 100 kgs. of a mixture of fatty alcohols mainly consisting of lauryl alcohol, and obtained from coconut oil by esterification of the fatty acids with ethyl alcohol, reduction of the ethyl ester, distillation of the product of the reduction and collection of the first 50% to 60% of the distillate, are heated to melting temperature about 30 C. and treated atthis temperature with 50 kgs. of chlorsulphonic acid;
- Eaample 2 100 kgs. of the same mixture of fatty alcohols is sulphonated with kgs. of fuming sulphuric acid 10% S0: at the temperature of 50 C.
- the products of the reaction are directly neu- Lralized by means of soda lye and separated by known methods from inorganic components such as sodium sulphate or sodium chloride.
- Example 3 100 kgs. of oleic alcohol are sulphated at 25 C. with kgs. of concentrated sulphuric acid. The mixture is poured into 150 kgs. of ice water and is neutralized by means of piperidine.
- the reaction may be represented by the following equations:
- Example 6 100 kgs. of ricinoleic alcohol obtained by re duction of ricinoleic acid by means of sodium and amyl alcohol, adding water, separating the wa- 0 tery alkali lwdroxide solution and removing the 8 amyl alcohol by distillation are treated with 150 CH3.
- (CH2) 7.CH2OH +3H2SO4 CH3.
- CH2 5.CH.SO4H.CH2.CH2
- Example 7 100 kgs. of stearic alcohol are treated at 40-50" C. with 50 kgs. of chlorosulphonio acid.
- the product is worked up as described in Example 3. A white paste is obtained.
- the reaction can be represented by the following formula:
- Glaubers salt may be added to the solution or to the dried product respectively, that the final product contains for example 35% calculated on free fatty alcohol.
- Example 9 100 kgs. of linoleic alcohol obtained by reduction of linoleic acid by means of an alkali metal and ethyl alcohol in a manner known per so, are dissolved in 50 kgs. of water free ethyl ether and treated with 200 kgs. of concentrated sulphuric acid at a temperature between 0 and 5 C. for several hours. The product is mixed with 300 kgs. chopped ice and 50 kgs. ethyl ether, washed with saturated Glaubers salt solution and neutralized by means of triethanolamine.
- a wetting and cleansing agent comprising essentially water-soluble sulphuric esters of alcohols obtained by sulphation of fatty material from which carboxyl groups, including combined carboxyl groups, are eliminated.
- a wetting and cleansing agent comprising essentially a water-soluble sulphation product of primary alcohols resulting from the reduction of the fatty acid radicals contained in fatty material.
- a composition of matter having isoap-lilze constituents.
- I I 10. Sulphated mixture of primary alcohols ob- 580% i I cleansing agents which, comprises reducing a fatty i material to form higher. alcohols. corresponding I to the fatty acid radicalscontainedtherein, sul' 1 and thence to, sulphuric a .;phat ng sa1d h gher alcohols toform alkylsulproperties consisting essentially' of sulphuric esters i a of ahphatic'alcohols having more than '8 carbon atoms obtainedfrom fatty material by.
- a composition of matter having soap-like properties consisting essentially of sulphuric esters of normal primary aliphatic alcohols having from 12 to 18 carbon atoms inclusive, obtained from fatty material by eliminating carboxyl groups from the carboxyl containing constituents.
- a soap-like material comprising essentially salts of acids of the group consisting of alkyl sulphuric acids and alkyl sulphonic acids derived from primary alcohols resulting from the reduction of the fatty acid radicals contained in fatty material.
Description
Patented July 31, 1934 UNITED STATES PATENT OFFICE SULPHURIC DERIVATIVE OF HIGHER ALCOHOLS Heinrich Bertsch, Chemnitz, Germany 18 Claims.
This invention relates to soap-like products and to the manufacture of soaps, detergents, and the like, and to improvements in treatment liquids for use in the textile, leather, and allied industries. It is the primary object of the invention to produce new soap-like materials and other substances of this character having greater wetting, cleansing, dispersing, and foaming properties than the agents heretofore used.
Water-soluble sulphuric esters produced by the action of sulphuric acid on fatty materials, including both fatty acids and esters of fatty acids, containing double linkages and/or hydroxyl groups, are widely employed as wetting, cleansing, and dispersing agents in the textile and related industries. Thus a sulphuric acid ester of the hydroxy stearic acid may be produced by treating oleic acid with sulphuric acid, and a sulphuric acid ester of a dihydroxy stearic acid may be obtained by the treatment of ricinoleic acid with sulphuric acid. These agents are not entirely satisfactory, since sulphated fatty materials heretofore available contain carboxyl groups-either free or combined with alkali, de-
pending upon the proportion of alkali used for neutralization after sulphationand in consequence are capable of forming insoluble alkali earth salts. For instance, the difiicultly soluble lime salts of these esters produce deleterious effects in the textile industry.
In accordance with the present invention, this defect is in large measure avoided if, instead of fatty acids or the esters of these acids, the corresponding alcohols obtained therefrom by replacement in effect of the carboxyl group whether free or combined with the CHzOH group are treated with sulphuric acid or with other sulphating or sulphonating agent. Commercial fats are essentially mixed glycerides of the various higher fatty acids, and the higher alcohols 0btainable therefrom are mixtures of alcohols of the general formula CxHyCH2OH. These mixtures consist predominantly of alcohols having 10 or more carbon atoms per molecule, correspending to the molecular weight of the fatty acids, free or combined, contained in the natural fats and fatty oils and the other commercially available fatty materials derived therefrom.
I have found that products soluble in water and valuable for use as wetting, cleansing, dispersing,
and foaming agents can be obtained by treating such alcohols with sulphuric acid or with other sulphating or sulphonating agent. These alcohols may be referred to collectively as normal primary alcohols having more than eight carbon atoms to the molecule.
Thus the invention contemplates the conversion of the free or combined fatty acids of fatty materials, i. e. animal and vegetable fats and oils, and manufactured derivatives such as oleic acid or ethyl oleate, into the corresponding alcohols, and the treatment of these alcohols with ,a sulphating or sulphonating agent such as sulphuric acid. Usually it is also advisable to neutralize the reaction product with a base, for example sodium hydroxide or ammonia to form a water soluble soap-like salt, as is common practice in the case of sulphated fatty acids or sulphated fatty oils, such as Turkey red oil.
The precise nature of the method selected to convert the fatty material to the alcohol may be varied. For instance, a well-known method is that of Bouveault and Blanc, in accordance with which an alkyl ester of a fatty acid, e. g. an ethyl oleate, is reduced by sodium or other alkali metal and a lower aliphatic alcohol such as butyl alcohol, or the improved method described in my application for Letters Patent Serial No. 472,764 may be used. Numerous processes are known for preparing the alkyl esters from fats and fatty acids.
The Bouveault and Blanc process is of general application for the preparation of both unsaturated and saturated alcohols. For instance, by this process oleic alcohol (C17H33CH2OH) may be prepared from esters of oleic acid (CnHaaCOOH). An octodecyl alcohol (C1'1H35CH2OH) may be formed from esters oi stearic acid (C11Ha5CO0H). Mixed saturated and unsaturated alcohols result when the unfractionated esters of the fatty acids of most natural fats, for example, tallow, are reduced according to the Bouveault and Blanc process.
An important example of a. method for preparing predominantly saturated alcohols is catalytic hydrogenation of esters under high pressure, as described in the application for U. S. Letters Patent of Wilhelm Normann, Serial No. 510,326, filed January 21, 1931, and assigned to the assignee of the present application. This method may be applied directly to the conversion of the natural glycerides, such as coconut oil, to primary alcohols for use in accordance with the present invention. 105
Fatty alcohols obtained from the source d scribed are next treated with a sulphating agent having water-binding properties. Ordinary concentrated sulphuric acid may be used, or stronger reagents such as anhydrous sulphuric acid, 110
' agents such as fuming sulphuric acid.
chlorsulphonic acid, or fuming sulphuric acid. The principal reaction occurring is the formation of sulphuric esters, frequently called alkyl sulphuric acids, for instance, as follows:
In the case of an unsaturated alcohol, some addition of sulphuric acid at the double bond also occurs, so that complete reaction of sulphuric acid with oleic alcohol would be according to the equation:
sulphuric ester of 1, 9-octodecanediol.
Unless a higher temperature is required to melt the alcohol, I prefer tov effect sulphation in the cold within the range of ordinary room temperature or lower, down to about 0 C. However, higher and lower temperatures can be used, and my invention is not restricted to a particular range of temperature of sulphation.
Under almost any practical condition of sulphation, there may be formed at least traces of sulphonic acids, the proportion of which may be increased by choice of sulphating medium and other conditions of reaction, for instance, by high reaction temperatures and by the use of highly concentrated energetically acting re- While these are not my preferred reaction conditions, it should be understood that the sulphation products made in accordance with the present invention are not purely esters, but may contain also appreciable amounts of sulphonic acids or sulphonates. For convenience, the products resulting from the treatment with sulphuric acid or other agent hereinbefore mentioned will be referred to generically as sulphuric reaction products.
One method of sulphating which is of fairly general application to different alcohol mixtures is to treat the alcohol just above its melting point with 100%-110% of the theoretical quantity of chlorsulphonic acid required according to the equation The acid reaction products obtained as de-.
scribed above are preferably carefully neutralized, for instance, with sodium hydroxide. Neutralization should be carried out at relatively low temperatures, preferably in a vessel fitted with a means for cooling. The resulting organic salts such as sodium lauryl sulphate may be separated from inorganic components such as sodium sulphate and sodium chloride by known methods, for instance, by dissolving in ethyl alcohol, decanting or filtering, and evaporating off the solvent. With or without this purification, the products obtained are in general readilysoluble in water, possess marked wetting, cleansing, dispersing, and foaming properties, and may be employed for manifold textile purposes. In a general way, they resemble the ordinary commercial sulphuric esters of the fats and fatty acids, but are greatly superior in resistance to precipitation by lime salts and the other characteristic constituents of hard water.
The sulphated products of oleic alcohol are particularly resistant to hardness and are high- 1y suitable for use in the textile and related industries.
Likewise a high resistance to the action of hard water is shown by the sulphated products of lauryl alcohol, which is the principal constituent of the mixed alcohols obtained by reduction of coconut, palm kernel and similar oils, or by reduction of the alkyl esters or the free fatty acids of these oils. Sulphated alcohols of this class have remarkable cleansing and foaming properties, and are valuable as soap substitutes, especially for use in hard water.
The sulphuric reaction products derived from lauryl alcohol, especially the esters and salts thereof, are also found to be particularly effective in the textile industry. Thus when starting from the fatty alcohols made from free fatty acids of the coconut oil or palm seed oil in a manner known per se by esterifying the fatty acids of the same with lower aliphatic alcohols and reducing the mixture of esters by means of sodium, it is advantageous to distill the reduction product and to use only the first 50% to 60% of the distillate. The product thus obtained consists mainly of lauryl alcohol, the somewhat less suitable higher fractions which contain principally myristyl alcohol and octodecyl alcohol being substantially eliminated. It should be understood, however, that the presence of the sulphuric derivatives of lower or higher alcohols, such as of myristyl alcohol with the lauryl alcohol derivatives does not materially decrease the efliciency of the final product.
Various other higher alcohols may be produced and converted into wetting and cleansing agents, substantially according to the procedure indicated in the above examples, for instance the following:
Alcohols obtained by catalytic hydrogenation of the free fatty acids of coconut oil and comprising mainly lauric alcohol, myristic alcohol, cetyl alcohol, and stearic alcohol or the single alcohols separated from each other by fractional distillation.
Alcohols obtained by catalytic hydrogenation of palm kernel oil or of the free fatty acids of palm kernel oil comprising similar constituents as the alcohols obtained from coconut oil.
Alcohols obtained by saponiflcation of spermaceti, sperm oil, beeswax and distillation according to Axelrad and Hochstadter (U. S. A. Patent 1,290,870)
Linoleic alcohol obtained by reduction of linoleic acid by means of sodium and ethyl alcohol.
Alcohols obtained by catalytic reduction of tallow or the free fatty acids of tallow.
Alcohols obtained by catalytic hydrogenation of the free fatty acids of coconut oil.
Alcohols obtained by catalytic hydrogenation of the free fatty acids of palm kernel oil.-
Alcohols obtained by reducing olive oil by means of metallic sodium and butyl alcohol.
Alcohols obtained by reducing the ethyl esters of tallow fatty acids by means of metallic sodium and. butyl alcohol.
Alcohols obtained by catalytic hydrogenation of the ethyl ester of commercial stearic acid.
Ricinoleic alcohol obtained by reduction of ricinoleic acid by means of sodium and ethyl alcohol.
The following examples are given to illustrate the manner in which the process may be carried out:
Example 1 100 kgs. of a mixture of fatty alcohols mainly consisting of lauryl alcohol, and obtained from coconut oil by esterification of the fatty acids with ethyl alcohol, reduction of the ethyl ester, distillation of the product of the reduction and collection of the first 50% to 60% of the distillate, are heated to melting temperature about 30 C. and treated atthis temperature with 50 kgs. of chlorsulphonic acid;
The foregoing reaction-may be represented by the following formula:
100 kgs. of pure lauryl alcohol would require for best results a higher proportion of chlorsulphonic acid about 60 kgs.
Eaample 2 100 kgs. of the same mixture of fatty alcohols is sulphonated with kgs. of fuming sulphuric acid 10% S0: at the temperature of 50 C.
The products of the reaction are directly neu- Lralized by means of soda lye and separated by known methods from inorganic components such as sodium sulphate or sodium chloride.
Example 3 Example 4 100 kgs. of oleic alcohol are sulphated at 25 C. with kgs. of concentrated sulphuric acid. The mixture is poured into 150 kgs. of ice water and is neutralized by means of piperidine.
The reaction may be represented by the following equations:
(1) CH3.(CH2) 'z.CH= -CH.(CH2) 7.CH2OH +H2SO4= CH3. (CH2) 7.CH=CH. (CH2) '1.CH2SO4H +H2O (2) CH3.(CH2)1.CH=CH.(CH2)'1.CH2OH +2H2SO4= CH3. (CH2) 7.CH2-CHSO4H. (CH2) 7.CH2SO4H Example 5 kgs. of the mixture of unsaturated and saturated fatty alcohols obtained by reduction of coconut oil by means of an alkali metal and butyl alcohol, adding water, separating the reculting watery alkali hydroxide solution and removing the butyl alcohol by distillation, are treated with 80 kgs. of chlorosulphonic acid at 35 C. The product is worked up as described in Example 3, neutralized with sodium hydroxide solution to form a white, readily water-soluble paste.
Example 6 v 100 kgs. of ricinoleic alcohol obtained by re duction of ricinoleic acid by means of sodium and amyl alcohol, adding water, separating the wa- 0 tery alkali lwdroxide solution and removing the 8 amyl alcohol by distillation are treated with 150 CH3. (CH2) 5.CHOH.CH2.CH==CH. (CH2) 7.CH2OH +3H2SO4= CH3. (CH2) 5.CH.SO4H.CH2.CH2
CH.SO4H.(CH2) 7.CH2.SO4H 95 Besides this reaction there may be also a reaction of only two or only one of the free groups (two hydroxyl groups and one double linkage) capable of reaction with sulphating means. These reactions yield for example the following products CH3. (CH2) 5.CH.SO4H.CH2.CH=
CH. CH2) 7.CH2.SO4H CH3. (CH2) 5.CHOH.CH2.CH= CH. (CH2) 7.CH.SO4H
Example 7 100 kgs. of stearic alcohol are treated at 40-50" C. with 50 kgs. of chlorosulphonio acid.
The product is worked up as described in Example 3. A white paste is obtained. The reaction can be represented by the following formula:
by saponiflcation of spermaceti oil by means of caustic lime and distillation of the saponification product according to U. S. A. Patent 1,290,870, said alcohols having an iodine number of about 50 and consisting mainly of cetyl alcohol and. oleic alcohol, are mixed with 100 kgs. of concentrated sulphuric acid at 40 C. The mass is then poured into 200 kgs. of ice water. The mixture is neutralized by adding sodium hydroxide solution of 28 B. The resulting solution containing 15-20% calculated on free fatty alcohol, is introduced in a spraying dryer of the Krause system and dried .at a temperature between 75-80 C., the temperature of the hot air entering at the bottom of dryer being about 170 C.
Before or after the drying operation such quantities of Glaubers salt may be added to the solution or to the dried product respectively, that the final product contains for example 35% calculated on free fatty alcohol.
Example 9 100 kgs. of linoleic alcohol obtained by reduction of linoleic acid by means of an alkali metal and ethyl alcohol in a manner known per so, are dissolved in 50 kgs. of water free ethyl ether and treated with 200 kgs. of concentrated sulphuric acid at a temperature between 0 and 5 C. for several hours. The product is mixed with 300 kgs. chopped ice and 50 kgs. ethyl ether, washed with saturated Glaubers salt solution and neutralized by means of triethanolamine.
The reaction is probably represented by the following equation: 1
' I i 1 on.(H2)mcrnom-msolacmrcnncom-l I CI-I.CH2,-CH=CH.(CH2:) TLCH2S04H-l-H20; Besides the esterification of the CHzDHgroup also addition or sulphuric acid tocheer both, of the Idoublelinkagesmay occur.
The following fatty .materialshave been found particularly j suitable for conversion to, alcohols I acids and whale 'oil 'fattyacids.
' z 9 applications Serial Nos. 350,135, filed Mar nj za; 1929,; and 433,815 filed. March :6, 31930.1o'f which lard. iwhale oil, coconut oil, palmkernel oil, alm
:wax',: spermaceti, sperm oil, beeswam. Montan The present invention is disclosed'in my prior thepresentapplication is a contin'uation in part. Z It is. to be understood that this invention is not limited to the specif c embodiments hereinbeffbrle. disclosed, but thatit includes all modifications I 1 j as to procedureand all equivalent materials comf ing ;withi-n the terms of the claims and .thescope or the tenor of thespecification.
. 1 Having thus described the inyention; what is claimed as nefwfand desired to be secured byii Let I t ers Patent is;
55-11 In themanufacture of soap-like materials,
i the combined steps of, converting the carboxyl groups of a fatty material to primary alcohol groups and then-reacting, the re sultingalcohols with asulphonating agent; .2. Aso'ap like materialcomprisingessentiallyQ i saltsjof alkyl sulphuric acids derived from primary alcohols resulting from the-reductionof the fatty acid radicals contained in fatty material.
3. A wetting and cleansing agent comprising essentially water-soluble sulphuric esters of alcohols obtained by sulphation of fatty material from which carboxyl groups, including combined carboxyl groups, are eliminated.
4. A wetting and cleansing agent comprising essentially a water-soluble sulphation product of primary alcohols resulting from the reduction of the fatty acid radicals contained in fatty material.
5. In the production of wetting and cleansing agents, the combined steps of converting the carboxyl groups of a fatty material to primary alcohol groups and then sulphating.
6. In the production of wetting and cleansing agents, the combined steps of reducing the esters of fatty and oily acids having more than 8 carbon atoms to the corresponding higher alcohols and thereafter-sulphating the resulting alcohols.
7. In the production of wetting and cleansing agents, the combined steps of reducing the esters of fatty acids having more than 8 carbon atoms johtained by reducing an unsaturated rial having imorelthan 8 carbon atoms. 1
. 8. The; process of manufacturing wetting and phuri acids and neutralizing with ebase to yield. 5011.1 ave? on. Cast r-Oil linseed .011 an. on. tejcna 1 water-Soluble salts Sam sulphuric nicalistearic' acid, technical olcic acid an'd-ricina j j j oleic acid, palmitic. acid, tallow fatty acids, Japan.
' 1 i 5 wax, 'methyl, ethyl; propyl and butyl este s or technical fatty acid mixtures such as stearic acids,
. oleic. acids, tallow. fatty acids, linseed; oil fatty 9. A composition of =matter having isoap-lilze constituents. I I 10. Sulphated mixture of primary alcohols ob- 580% i I cleansing agents which, comprises reducing a fatty i material to form higher. alcohols. corresponding I to the fatty acid radicalscontainedtherein, sul' 1 and thence to, sulphuric a .;phat ng sa1d h gher alcohols toform alkylsulproperties consisting essentially' of sulphuric esters i a of ahphatic'alcohols having more than '8 carbon atoms obtainedfrom fatty material by. eliminat ing carboxyl. groups from thecarboxylicontaining a sulphation Droduct'of anunsaturated alcohol #12. The; process: of producing wjettifngl {and I cleansing agents composed of. alcohol sulphate a s having more than .8 carbonatoms compris ing producingalcohols from a fatty material con 1 .taining fatty acid radicals of, more than 8 carbon atoms, s'u1phating said alcohols at a temperature fattymatef W i f and in the absence of organic. solvents'of said I alcoholsiandthen neutralizing the reaction prod nets to form the salts of the sulphated alcohols.
13. The process of producing alcohol sulphates 'tioned number'ofcarbon atoms, and: sulphating said alcohols at a temperature sufiiciently low to produce substantially only sulphates and in the absence of organic solvents of said alcohols.
14. The product produced by the process described in claim 12.
15. The product produced by the process described in claim 13.
16. Sulphuric ester of primary stearyl alcohol.
17. A composition of matter having soap-like properties consisting essentially of sulphuric esters of normal primary aliphatic alcohols having from 12 to 18 carbon atoms inclusive, obtained from fatty material by eliminating carboxyl groups from the carboxyl containing constituents.
18. A soap-like material comprising essentially salts of acids of the group consisting of alkyl sulphuric acids and alkyl sulphonic acids derived from primary alcohols resulting from the reduction of the fatty acid radicals contained in fatty material.
HEINRICH BERTSCH.
- .havingifroinmtolfi carbon atomsinclusive, com- I prising; producing, alcoholsfrom' a fatty material j containing fatty acid radicals of the above men sufficiently low ,to'produceprincipallysulphates;
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US700355A US2114042A (en) | 1928-03-30 | 1933-11-29 | Sulphuric derivatives of higher alcohols |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB150315D DE659277C (en) | 1928-03-30 | 1928-03-30 | Dispersing, wetting, cleaning and penetrating agents |
Publications (1)
Publication Number | Publication Date |
---|---|
US1968797A true US1968797A (en) | 1934-07-31 |
Family
ID=7002162
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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US350135A Expired - Lifetime US1968793A (en) | 1928-03-30 | 1929-03-26 | Sulphuric ester of higher alcohols |
US650203A Expired - Lifetime US1968797A (en) | 1928-03-30 | 1933-01-04 | Sulphuric derivative of higher alcohols |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
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US350135A Expired - Lifetime US1968793A (en) | 1928-03-30 | 1929-03-26 | Sulphuric ester of higher alcohols |
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DE (1) | DE659277C (en) |
FR (1) | FR671456A (en) |
GB (1) | GB308824A (en) |
NL (1) | NL24700C (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2480579A (en) * | 1943-10-21 | 1949-08-30 | Colgate Palmolive Peet Co | Detergent products and their preparation |
US2489955A (en) * | 1943-08-25 | 1949-11-29 | Colgate Palmolive Peet Co | Preparation of nondusting organic detergent compositions |
US2553716A (en) * | 1946-07-19 | 1951-05-22 | Rare Galen Inc | Mild detergent and method of making same |
US2603606A (en) * | 1952-07-15 | Alkyl sulfates | ||
US2613218A (en) * | 1950-06-12 | 1952-10-07 | Purex Corp Ltd | Vacuum neutralization of detergents |
DE763234C (en) * | 1935-06-09 | 1953-01-19 | Wacker Chemie Gmbh | Process for the production of sulfuric acid or phosphoric acid esters of higher molecular weight, monohydric, saturated, aliphatic, primary alcohols |
US2819318A (en) * | 1953-12-02 | 1958-01-07 | Ethyl Corp | Alcohols derived from babassu oil |
US3249550A (en) * | 1964-05-27 | 1966-05-03 | Dow Corning | Glass cleaning compositions |
WO1995001959A1 (en) * | 1993-07-09 | 1995-01-19 | Henkel Kommanditgesellschaft Auf Aktien | Method of producing alkyl sulphates with improved properties |
WO1996023768A1 (en) * | 1995-02-01 | 1996-08-08 | Henkel Kommanditgesellschaft Auf Aktien | Dimeric alcohol-bis and trimeric alcohol-tris-sulphates and ether sulphates |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2619467A (en) * | 1952-11-25 | Detergent mixtures containing | ||
DE763809C (en) * | 1933-07-21 | 1954-05-03 | Hydrierwerke A G Deutsche | Process for the manufacture of sulphonation products |
GB391433A (en) * | 1939-07-24 | 1933-04-27 | Ig Farbenindustrie Ag | Improvements relating to the treatment of textile materials |
US2666527A (en) * | 1945-06-22 | 1954-01-19 | Peterson Filters & Eng | Method of promoting filtration |
US4000081A (en) * | 1969-01-10 | 1976-12-28 | Chevron Research Company | Lime soap dispersant compounds |
US3634269A (en) * | 1969-01-10 | 1972-01-11 | Chevron Res | Hydrocarbyl butanediol disulfate phosphate-free detergent compositions |
US5037992A (en) * | 1989-12-18 | 1991-08-06 | The Procter & Gamble Company | Process for sulfating unsaturated alcohols |
JP2000500186A (en) * | 1996-06-28 | 2000-01-11 | ザ、プロクター、エンド、ギャンブル、カンパニー | Liquid cleaning compositions and shampoos containing dianionic or alkoxylated dianionic surfactants |
-
0
- GB GB308824D patent/GB308824A/en active Active
- NL NL24700D patent/NL24700C/xx active
-
1928
- 1928-03-30 DE DEB150315D patent/DE659277C/en not_active Expired
-
1929
- 1929-03-14 FR FR671456D patent/FR671456A/en not_active Expired
- 1929-03-26 US US350135A patent/US1968793A/en not_active Expired - Lifetime
-
1933
- 1933-01-04 US US650203A patent/US1968797A/en not_active Expired - Lifetime
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2603606A (en) * | 1952-07-15 | Alkyl sulfates | ||
DE763234C (en) * | 1935-06-09 | 1953-01-19 | Wacker Chemie Gmbh | Process for the production of sulfuric acid or phosphoric acid esters of higher molecular weight, monohydric, saturated, aliphatic, primary alcohols |
US2489955A (en) * | 1943-08-25 | 1949-11-29 | Colgate Palmolive Peet Co | Preparation of nondusting organic detergent compositions |
US2480579A (en) * | 1943-10-21 | 1949-08-30 | Colgate Palmolive Peet Co | Detergent products and their preparation |
US2553716A (en) * | 1946-07-19 | 1951-05-22 | Rare Galen Inc | Mild detergent and method of making same |
US2613218A (en) * | 1950-06-12 | 1952-10-07 | Purex Corp Ltd | Vacuum neutralization of detergents |
US2819318A (en) * | 1953-12-02 | 1958-01-07 | Ethyl Corp | Alcohols derived from babassu oil |
US3249550A (en) * | 1964-05-27 | 1966-05-03 | Dow Corning | Glass cleaning compositions |
WO1995001959A1 (en) * | 1993-07-09 | 1995-01-19 | Henkel Kommanditgesellschaft Auf Aktien | Method of producing alkyl sulphates with improved properties |
WO1996023768A1 (en) * | 1995-02-01 | 1996-08-08 | Henkel Kommanditgesellschaft Auf Aktien | Dimeric alcohol-bis and trimeric alcohol-tris-sulphates and ether sulphates |
US5922670A (en) * | 1995-02-01 | 1999-07-13 | Henkel Kommanditgesellschaft Auf Aktien | Dimeric alcohol-bis and trimeric alcohol-tris-sulphates and ether sulphates thereof |
Also Published As
Publication number | Publication date |
---|---|
FR671456A (en) | 1929-12-18 |
US1968793A (en) | 1934-07-31 |
GB308824A (en) | |
NL24700C (en) | |
DE659277C (en) | 1938-04-29 |
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