US1932179A - Sulphuric acid derivatives of - Google Patents
Sulphuric acid derivatives of Download PDFInfo
- Publication number
- US1932179A US1932179A US1932179DA US1932179A US 1932179 A US1932179 A US 1932179A US 1932179D A US1932179D A US 1932179DA US 1932179 A US1932179 A US 1932179A
- Authority
- US
- United States
- Prior art keywords
- acid
- radicle
- sulphuric
- denotes
- groups
- 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
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title description 26
- 239000003795 chemical substances by application Substances 0.000 description 52
- 125000001931 aliphatic group Chemical group 0.000 description 48
- 239000002253 acid Substances 0.000 description 44
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 38
- 150000002148 esters Chemical class 0.000 description 36
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 34
- 125000004432 carbon atoms Chemical group C* 0.000 description 32
- 239000000047 product Substances 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- -1 aromatic primary Chemical class 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- 229910052739 hydrogen Inorganic materials 0.000 description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 22
- 239000001257 hydrogen Substances 0.000 description 22
- 239000001117 sulphuric acid Substances 0.000 description 22
- 235000011149 sulphuric acid Nutrition 0.000 description 22
- 230000000875 corresponding Effects 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- AKEJUJNQAAGONA-UHFFFAOYSA-N Sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 18
- 150000007513 acids Chemical class 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 18
- 125000004185 ester group Chemical group 0.000 description 18
- 150000001735 carboxylic acids Chemical class 0.000 description 16
- 239000000194 fatty acid Substances 0.000 description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- 230000001476 alcoholic Effects 0.000 description 14
- 150000004982 aromatic amines Chemical class 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- 235000014113 dietary fatty acids Nutrition 0.000 description 14
- 239000011780 sodium chloride Substances 0.000 description 14
- 235000002639 sodium chloride Nutrition 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 230000001264 neutralization Effects 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N Hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 8
- 150000003931 anilides Chemical class 0.000 description 8
- 235000019864 coconut oil Nutrition 0.000 description 8
- 239000003240 coconut oil Substances 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 229940051881 Anilide analgesics and antipyretics Drugs 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000003925 fat Substances 0.000 description 6
- 235000019197 fats Nutrition 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 238000009991 scouring Methods 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- 239000000080 wetting agent Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N Lauric acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 230000001804 emulsifying Effects 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 150000005002 naphthylamines Chemical class 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000002829 nitrogen Chemical group 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N triclene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- LRVUCXFUHLHEDF-UHFFFAOYSA-N 1-(4-methylphenyl)ethane-1,2-diol Chemical compound CC1=CC=C(C(O)CO)C=C1 LRVUCXFUHLHEDF-UHFFFAOYSA-N 0.000 description 2
- WVRFSLWCFASCIS-UHFFFAOYSA-N 3-(3-ethylcyclopentyl)propanoic acid Chemical class CCC1CCC(CCC(O)=O)C1 WVRFSLWCFASCIS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N Benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 241000518994 Conta Species 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- 229920000715 Mucilage Polymers 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-Methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- BWDQTWCKOCDMAH-UHFFFAOYSA-N N-naphthalen-1-yloctanamide Chemical compound C1=CC=C2C(NC(=O)CCCCCCC)=CC=CC2=C1 BWDQTWCKOCDMAH-UHFFFAOYSA-N 0.000 description 2
- 210000004940 Nucleus Anatomy 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N Phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- WBHHMMIMDMUBKC-QJWNTBNXSA-N Ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 2
- WBHHMMIMDMUBKC-GKUQOKNUSA-N Ricinoleic acid Natural products CCCCCC[C@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-GKUQOKNUSA-N 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N Sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N Sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 235000015450 Tilia cordata Nutrition 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- AMIXGQGFDAXFET-UHFFFAOYSA-N [Na].NCl Chemical compound [Na].NCl AMIXGQGFDAXFET-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000005591 charge neutralization Effects 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000008233 hard water Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- OUFCLLRNNJZLOX-UHFFFAOYSA-N methyl 2-hydroxyoctadecanoate Chemical compound CCCCCCCCCCCCCCCCC(O)C(=O)OC OUFCLLRNNJZLOX-UHFFFAOYSA-N 0.000 description 2
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 235000019488 nut oil Nutrition 0.000 description 2
- 239000010466 nut oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 150000002943 palmitic acids Chemical class 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 235000015108 pies Nutrition 0.000 description 2
- 235000019353 potassium silicate Nutrition 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000001681 protective Effects 0.000 description 2
- 229960003656 ricinoleic acid Drugs 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/52—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton the carbon skeleton being further substituted by doubly-bound oxygen atoms
- C07C309/53—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton the carbon skeleton being further substituted by doubly-bound oxygen atoms the carbon skeleton containing carbon atoms of quinone rings
- C07C309/54—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton the carbon skeleton being further substituted by doubly-bound oxygen atoms the carbon skeleton containing carbon atoms of quinone rings at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C309/55—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Definitions
- X is either OH (acid), 031 (ester),
- anhydride R1 being an aliphatic radicle ⁇ or halogen, and R contains from 5 to carbon atoms with an aromatic primary or secondary amine, which is free from aliphatic alcoholic and. chromophorous groups, the resulting arylides being then reacted with sulphonating agents to form either'sulphohic acids or sulphuric esters, or mixtures of both, or products which contain both sulphuric ester and sulphonic groups, if the arylides are free or only contain an insufilcient quantity of sulphuric ester and/or sulphonic acid radlcles.
- the acid components of the arylides do not include mixed aliphatic aromatic acids but may be chosen from any saturated aliphatic acids containing from 6 to 16 carbon atoms especially from those of oils or fats of vegetal, i. e. animal or vegetable origin. Instead of the free acids, their anhydrides or halides or the oils or fats themselves (esters) may be employed.
- the synthetic high molecular fatty acids obtainable by the oxidation of paraffin wax and similar high molecular hydrocarbons by means of gase- 40 ous oxidizing agents may be employed or saturated resinic or naphthenic acids; lower aliphatic carboxylic acids containing at least 6 carbon atoms, such as caproic acid, may also be employed.
- acids are for example heptylic, caprylic, nonylic, caprinic, lauric, myristie and palmitic acids as well as the corresponding hydroxycarboxylic acids, such as hydroxy-louric acid, or mixtures of such acids,
- the said acids may also contain other substituents such as nitro or amino groups.
- the said aromatic amines may be chosen from aniline, di-phenylamine, benzidine, biphenyl amines or from naphthylamines and like aromatic amines. In any case these amines must not contain aliphatic alcoholic groups since otherwise esters might be obtained instead of the desired amines, and the amines must be free from chrcmophorous groups since otherwise colored compounds might be obtained which cannot be used for the purposes intended.
- the said bases may be employed in the free state or also in the form of their salts when alkaline agents are present during the formation of the arylides.
- the acid components may contain one or more sulphonic acid or sulphuric ester groups and the aromatic amines may contain sulphonic groups and in these cases the subsequent sulpho nation may be dispensed with; the arylides containing a lower number of sulphuric ester or 5111-- phonic groups are usually suitable as washing and scouring agents and their solubility in water may be increased by introducing further sulphonic acid groups, or of sulphuric ester groups if the acid radicles contain hydroxyl groups.
- the carboxylic acids may be converted into arylides with the aid of amino sulphonic acids as for example sulphanilic acid and the like; on the other hand the.
- carboxylic acids may contain sulphuric ester and/or sulphonic groups as for example hydroxy-stearic sulphonic acid or its methyl ester (obtainable by sulphonating oleic methyl ester with chlorsulphonic acid in the presence of ethyl ether and subsequent washing with alkali), the sulphuric ester of hydroxystearic methyl ester (obtainable by acting with dimethyl sulphate on the sodium salt of hydroxystearic sulphuric ester which latter can be obtained by acting on oleic acid with sulphuric acid at about 20 C.) dihydroxy-stearic sulphuric ester (obtainable from ricinoleic acid and the like).
- hydroxy-stearic sulphonic acid or its methyl ester obtainable by sulphonating oleic methyl ester with chlorsulphonic acid in the presence of ethyl ether and subsequent washing with alkali
- higher amines such as naphthyl amines for the conver sion
- lower carboxylic acids such as caproic acid or another acid containing up to 10 carbon atoms
- higher carboxylic acids or their derivatives such as lauric acid and myristic oil
- arylides which have been prepared from higher carboxylic acids, or their derivatives, and from the higher aromatic amines.
- Stearic acid or still higher carboxylic acids are not employed since products prepared therefrom show an insufd cient solubility and sensitivity to precipitation by lime compounds.
- Arylides from lower acids and lower amines may be usefully employed as wetting agents in baths of a rather high content s such as are used for many purposes of the industries.
- Sulphuric esters for example, can be obtained from arylides containing hydroxyl groups as pointed out above.
- the reaction may be carried out with concentrated sulphuric acid or also with stronger sulphonating agents, such as fuming sulphuric acid, sulphur trioxide or chlorsulphonic acid, which latter agents or mixtures thereof with sulphuric acid are usually preferred.
- the reaction may be carried out in the presence of diluents, such as carbon tetrachloride, trichlor ethylene, nitrobenzene, acetic acid and the like which usually allow of reducing the temperature of working, and/or in the presence of agents removing water, such as anhydrides or chlorides of organic or inorganic acids.
- diluents such as carbon tetrachloride, trichlor ethylene, nitrobenzene, acetic acid and the like which usually allow of reducing the temperature of working, and/or in the presence of agents removing water, such as anhydrides or chlorides of organic or inorganic acids.
- At least one molecular proportion of sulphonating agent is usually employed with each molecular proportion of the arylide concerned, but in the aforesaid case of acting on compounds containing hydroxyl groups with strong sulphonating agents, such as sulphur trioxlde or chlorsulphonic acid or with mixtures of milder sulphonating agents with the strong sulphonating agents or with agents removing water, the quantity of the strong sulphonating agents, or of the agents removing water should not exceed one molecular proportion for each hydroxyl group. In most cases, the temperature employed during the reaction should not con siderably exceed 40 C. when more than one molecular proportion of sulphonating agent is employed for each molecular proportion of arylide.
- the temperature of a sulphonation by means of sulphuric acid monohydrate must exceed 40 C., a temperature of about 100 C. being preferably chosen, since otherwise sulphuric esters might be formed if hydroxyl groups be present or no reaction takes place.
- RCO denote a radicle of an aliphatic, that is an open chain aliphatic or cycloaliphatic, saturated carboxylic acid containing from 6 to 16 carbon atoms
- R1 denotes an aromatic monoor polynuclear radicle free from aliphatic and chromophorous groups
- X denotes hydrogen or a radicle of the kind denoted by Rl or the same as R1.
- R or R1, or both will contain at least one sulphonic acid radicle, or R will contain a sulphuric ester radicle and R1 may then contain one or more sulphonic acid radicles.
- R may contain both a sulphuric ester radicle and a sulphonic acid radicle, as may happen for example by a condensation of a hydroxy-fatty acid sulphonic acid with an amine, or amine sulphonic acid, and subsequent treatment with a sulphonating agent.
- the number of carbon atoms in RrCO cannot be chosen below 6, since, otherwise, the products would not substantially showthe desired properties.
- the resulting products are distinguished by excellent wetting properties, in neutral, acid or also alkaline baths.
- the products are also not precipitated by the constituents of hard water. Consequently the products according to the present invention constitute highly valuable assistants for all the branches of the textile and allied industries.
- Anilides prepared from hydroxylbearing fatty or resinic acids, and treatment with a sulphonatng agent may or the condensation of higher prlmary aromatic amines with carboxylic acids containing sulphonic or sulphuric ester groups may generally find useful application espec'ally as wetting agents, whereas arylides prepared from fatty acids free.
- the secondary arylides are particularly stable even in alkaline baths, have a high emulsifying and levelling power and a far reaching power for dispersing water-insoluble or difflcultly water-soluble solid substances, such as alkaline earth metal soaps, water-insoluble dyestuffs or other water-insoluble coloring mater'als, fats, waxes and the like.
- arylides according to the present invention may be employed as such or in conjunction with other wetting or emulsifying agents, such as soaps, products of the type of Turkey red oils, sulphonic ac'ds of aromatic and especially of polynuclear compounds or their salts, hydroxyalkyl amines, quaternary ammonium bases or their salts, or with protective colloids,-such as glue, gelatine or vegetable mucilages or gums.
- wetting or emulsifying agents such as soaps, products of the type of Turkey red oils, sulphonic ac'ds of aromatic and especially of polynuclear compounds or their salts, hydroxyalkyl amines, quaternary ammonium bases or their salts, or with protective colloids,-such as glue, gelatine or vegetable mucilages or gums.
- Salts as for example soda, sodium bicarbonate, waterglass, common salt, neutral or acid sod um sulphate may be added, or organic solvents, such as monocresyl ethylene glycol ether, trichlorethylene or bleaching agents, such as perborates, percarbonates, para-toluene sulphonic chloramide sodium.
- the said agents are employed in quantities depending on the desired purpose and several of them may be added conjofntly.
- the quantity of these additions may be the same as that of the arylides or considerably higher depending on the purposes of emulsifying, wetting, washing, cleaning or dispers'ng solid water-insoluble materials in water.
- the quantity of the sulphonated arylides may be as low as a few per cent or even a few per thousand of the whole liquors.
- All the products accord ng to the present invention must be free from nitro and auxochromic groups, since otherwise they would be inoperative for the different purposes of their application and should preferably contain at least 12 carbon atoms.
- Example 1 100 parts of' oc-hYdIOXY-iiilll'lC anilide (obtainable by heating a-hydroxy-lauric methyl ester and aniline until the distillat'on of methyl alcohol hasceased) are mixed at about 35 C. with 200 parts of concentrated sulphuric acid and are then treated with parts of fuming sulphuric acid conta ning about 23 percent of S03. The re- (Omiwo-onmi-osomu.)
- a similar product can be obtained from di-phenylamine in the place of aniline.
- Example 2 1000 parts of a mixture-of saturated fatty acids containing mainly from 12 to 15 carbon atoms and obtained by the liquid phase oxidation of paraifin wax with the aid of air while warming to say 150 C. and separating the acids from unattacked initial material, are heated under reflux with 2000 parts 01' aniline for 17 hours to from 180 to 190 C., the water formed during the reaction being continuously distilled oil. The remainders of free aniline are then distilled off in vacuo and the residue is dissolved in 4,750 parts of sulphuric acid monohydrate. 2200 parts of fuming sulphuric acid containing 23 percent of sulphur trioxide are then introduced into the solution at about 10 C. and the mixture is stirred for about 20 hours at 20 to 25 C.
- the reaction product isthen poured onto a mixture of ice and common salt and filtered.
- the product may be employed as such or after neutralization with caustic soda, if desired after removal of the mineral acid salts. sesses a high resistance to acid and a high scouring power superior to that of soaps and is not precipitated from aqueous solutions by means of alkaline earth metals.
- Example 3 500 parts of coconut oil'fatty acid anilide (from nut oil and thus corresponds to the general formula is poured onto ice, rendered neutral with caustic soda and inspissated.
- Example 4 14 parts of e-naphthyl-amine are dissolved in 10 parts of pyridine, whereupon 30 parts of ca- It posprylic chloride are added while cooling After warming to about 98 C. for hour under reflux the product is washed with aqueous acetic acid and dried. 20 parts of the caprylic naphthyl amide are dissolved in 19 parts of sulphuric acid mono-hydrate, 40 parts of fuming sulphuric acid containing 23 per cent of S03 are added and the Whole is warmed to from 50 to 60 C. until a sam pie is soluble in water. The reaction mixture is poured onto ice, rendered neutral with caustic soda and inspissated.
- Example 5 20 parts of undecylic toluidide are dissolved in 40 parts of sulphuric acid monohydrate and then stirred at from to 120 C. with 40 parts of fuming sulphuric acid containing 23 per cent of S03 until the product is water-soluble, whereupon the latter is poured onto ice, neutralized with 100 aqueous caustic soda solution and inspissated.
- Example 6 25 parts of saturated naphthenic (ii-phenylamide, obtainable by acting on a solution of di phenylamine in pyridine with naphthenic chloride (prepared by acting with phosphorus trichloride on commercial saturated napththenic acid) are mixed with 20 parts of sulphuric acid monohydrate at from 10 to 15 C., whereupon 50 parts of fuming sulphuric acid containing 23 per cent of SO: are added and the whole is heated to about 98 C. until a sample is soluble in water. The reaction mixture is poured onto ice, neutralized with aqueous caustic soda and inspissated.
- R-CO denotes an aliphatic saturated radicle containing from 6 to 16 carbon atoms
- R1 denotes an aromatic radicle of the benzene or naphthalene series free from aliphatic alcoholic and chromophorous groups
- X denotes hydrogen or a radicle as denoted by R1, at least a hydrogen atom of R or R1 being substituted by a sulphonic acid group or at least a hydrogen atom of R being substituted by a sulphuric ester group.
- R-CO denotes an aliphatic saturated radicle containing from 6 to 16 carbon atoms
- R1 denotes an aromatic radicle free from allphatic alcoholic and chromophorous groups
- X denotes hydrogen or a radicle as denoted by R1, at least a hydrogen atom of R or R1 being substituted by a sulphonic acid group or at least a hydrogen atom of R being substituted by a sulphuric ester group.
- -R1 denotes an aromatic radicle free from aliphatic alcoholic and chromophorous groups and X denotes hydrogen or a radicle as denoted by R1, at least one hydrogen atom of R or R1 being substituted by a sulphonic acid group.
- R1 denotes an aromatic radicle free from aliphatic alcoholic and chromophorous groups and X denotes hydrogen or a radicle as denoted by R1, at least one hydrogen atom of R and one hydrogen atom of R1 being substituted by sulphonic acid groups.
- RCO denotes an aliphatic saturated radicle containing from 6 to 16 carbon atoms
- R1 denotes an aromatic mono-nuclear hydrocarbon radicle
- X denotes hydrogen or a radicle as denoted by R1, at least a hydrogen atom of R or R1 being substituted by a sulphonic acid group or at least a hydrogen atom of R being substituted by a sulphuric ester group.
- R-OON R1 denotes the radicles of the fatty acids of a liquid phase oxidation of paramn wax with the aid of air while warming
- R1 denotes an 1 aromatic mono-nuclear hydrocarbon radicle
- X denotes hydrogen or a radicle as denoted by R1, at least a hydrogen atom of R or R1 being substituted by a sulphonic acid group or at least a hydrogen atom of R being substituted by a sulphuric ester group.
- a mixture of carboxylic anilides correnotes hydrogen.
Description
Patented Oct. 24, 1933 UNITED STATES PATENT orricr:
SULPHURIC ACID DERIVATIVES OF CARBOXYLIC ARYLIDES No Drawing. Application May 27, 1932, Serial No. 614,032, and in Germany April 12, 1929 13 Claims.
in which X is either OH (acid), 031 (ester),
(anhydride R1 being an aliphatic radicle} or halogen, and R contains from 5 to carbon atoms with an aromatic primary or secondary amine, which is free from aliphatic alcoholic and. chromophorous groups, the resulting arylides being then reacted with sulphonating agents to form either'sulphohic acids or sulphuric esters, or mixtures of both, or products which contain both sulphuric ester and sulphonic groups, if the arylides are free or only contain an insufilcient quantity of sulphuric ester and/or sulphonic acid radlcles. The acid components of the arylides do not include mixed aliphatic aromatic acids but may be chosen from any saturated aliphatic acids containing from 6 to 16 carbon atoms especially from those of oils or fats of vegetal, i. e. animal or vegetable origin. Instead of the free acids, their anhydrides or halides or the oils or fats themselves (esters) may be employed. Similarly, the synthetic high molecular fatty acids obtainable by the oxidation of paraffin wax and similar high molecular hydrocarbons by means of gase- 40 ous oxidizing agents may be employed or saturated resinic or naphthenic acids; lower aliphatic carboxylic acids containing at least 6 carbon atoms, such as caproic acid, may also be employed. Further specific examples of the acids are for example heptylic, caprylic, nonylic, caprinic, lauric, myristie and palmitic acids as well as the corresponding hydroxycarboxylic acids, such as hydroxy-louric acid, or mixtures of such acids, The said acids may also contain other substituents such as nitro or amino groups. p
The said aromatic amines may be chosen from aniline, di-phenylamine, benzidine, biphenyl amines or from naphthylamines and like aromatic amines. In any case these amines must not contain aliphatic alcoholic groups since otherwise esters might be obtained instead of the desired amines, and the amines must be free from chrcmophorous groups since otherwise colored compounds might be obtained which cannot be used for the purposes intended. The said bases may be employed in the free state or also in the form of their salts when alkaline agents are present during the formation of the arylides. As already stated the acid components may contain one or more sulphonic acid or sulphuric ester groups and the aromatic amines may contain sulphonic groups and in these cases the subsequent sulpho nation may be dispensed with; the arylides containing a lower number of sulphuric ester or 5111-- phonic groups are usually suitable as washing and scouring agents and their solubility in water may be increased by introducing further sulphonic acid groups, or of sulphuric ester groups if the acid radicles contain hydroxyl groups. Thus, for example, the carboxylic acids may be converted into arylides with the aid of amino sulphonic acids as for example sulphanilic acid and the like; on the other hand the. carboxylic acids may contain sulphuric ester and/or sulphonic groups as for example hydroxy-stearic sulphonic acid or its methyl ester (obtainable by sulphonating oleic methyl ester with chlorsulphonic acid in the presence of ethyl ether and subsequent washing with alkali), the sulphuric ester of hydroxystearic methyl ester (obtainable by acting with dimethyl sulphate on the sodium salt of hydroxystearic sulphuric ester which latter can be obtained by acting on oleic acid with sulphuric acid at about 20 C.) dihydroxy-stearic sulphuric ester (obtainable from ricinoleic acid and the like).
Generally speaking it is advisable to take higher amines, such as naphthyl amines for the conver sion when lower carboxylic acids, such as caproic acid or another acid containing up to 10 carbon atoms are employed, and higher carboxylic acids or their derivatives, such as lauric acid and myristic oil, when a lower amine, such as aniline, is used. Particularly suitable are in many cases arylides which have been prepared from higher carboxylic acids, or their derivatives, and from the higher aromatic amines. Stearic acid or still higher carboxylic acids are not employed since products prepared therefrom show an insufd cient solubility and sensitivity to precipitation by lime compounds. Arylides from lower acids and lower amines may be usefully employed as wetting agents in baths of a rather high content s such as are used for many purposes of the industries.
The action and results of the treatment with sulphonating agents depend on the arylides to be worked and on the conditions of the treatment. Sulphuric esters, for example, can be obtained from arylides containing hydroxyl groups as pointed out above. For the production of sulphuric esters the reaction may be carried out with concentrated sulphuric acid or also with stronger sulphonating agents, such as fuming sulphuric acid, sulphur trioxide or chlorsulphonic acid, which latter agents or mixtures thereof with sulphuric acid are usually preferred. The reaction may be carried out in the presence of diluents, such as carbon tetrachloride, trichlor ethylene, nitrobenzene, acetic acid and the like which usually allow of reducing the temperature of working, and/or in the presence of agents removing water, such as anhydrides or chlorides of organic or inorganic acids. At least one molecular proportion of sulphonating agent is usually employed with each molecular proportion of the arylide concerned, but in the aforesaid case of acting on compounds containing hydroxyl groups with strong sulphonating agents, such as sulphur trioxlde or chlorsulphonic acid or with mixtures of milder sulphonating agents with the strong sulphonating agents or with agents removing water, the quantity of the strong sulphonating agents, or of the agents removing water should not exceed one molecular proportion for each hydroxyl group. In most cases, the temperature employed during the reaction should not con siderably exceed 40 C. when more than one molecular proportion of sulphonating agent is employed for each molecular proportion of arylide.
If, however, sulphonic acids are to be produced and when the primary reaction products do not already contain one or more sulphonic groups, the temperature of a sulphonation by means of sulphuric acid monohydrate must exceed 40 C., a temperature of about 100 C. being preferably chosen, since otherwise sulphuric esters might be formed if hydroxyl groups be present or no reaction takes place. When stronger sulphonating agents, such as fuming sulphuric acid, sulphur trioxide or chlorsulphonic acid or mixtures of mild sulphonating agents with these or with agents removing water be employed for this sulphonation of compounds containing one or more hydroxyl groups, the quantity of these strong sulphonating agents or of the agents removing water must exceed one molecular proportion per each hydroxyl group present. It is obvious that variations of the conditions described may lead to the production of mixtures of products of the said different types. When working with considerable quantities'of strong sulphonating agents sulphonic radicles may be introduced into an aliphatic radicle of such an arylide together with a sulphonation of the nucleus.
The products according to the present invention correspond to the general formula wherein RCO denote a radicle of an aliphatic, that is an open chain aliphatic or cycloaliphatic, saturated carboxylic acid containing from 6 to 16 carbon atoms, R1 denotes an aromatic monoor polynuclear radicle free from aliphatic and chromophorous groups, whereas X denotes hydrogen or a radicle of the kind denoted by Rl or the same as R1. In any case R or R1, or both, will contain at least one sulphonic acid radicle, or R will contain a sulphuric ester radicle and R1 may then contain one or more sulphonic acid radicles. As another possibility R may contain both a sulphuric ester radicle and a sulphonic acid radicle, as may happen for example by a condensation of a hydroxy-fatty acid sulphonic acid with an amine, or amine sulphonic acid, and subsequent treatment with a sulphonating agent. The number of carbon atoms in RrCO cannot be chosen below 6, since, otherwise, the products would not substantially showthe desired properties.
The resulting products are distinguished by excellent wetting properties, in neutral, acid or also alkaline baths. The products are also not precipitated by the constituents of hard water. Consequently the products according to the present invention constitute highly valuable assistants for all the branches of the textile and allied industries. Anilides prepared from hydroxylbearing fatty or resinic acids, and treatment with a sulphonatng agent may or the condensation of higher prlmary aromatic amines with carboxylic acids containing sulphonic or sulphuric ester groups may generally find useful application espec'ally as wetting agents, whereas arylides prepared from fatty acids free. from hydroxyl groups, and sulphonation, are particularly valuable washing, scouring, softening and emulsifying agents, as well as the products prepared by the condensation of high molecular saturated carboxylic acids and aromatic primary amines containing sulphonic groups. The secondary arylides are particularly stable even in alkaline baths, have a high emulsifying and levelling power and a far reaching power for dispersing water-insoluble or difflcultly water-soluble solid substances, such as alkaline earth metal soaps, water-insoluble dyestuffs or other water-insoluble coloring mater'als, fats, waxes and the like.
The arylides according to the present invention may be employed as such or in conjunction with other wetting or emulsifying agents, such as soaps, products of the type of Turkey red oils, sulphonic ac'ds of aromatic and especially of polynuclear compounds or their salts, hydroxyalkyl amines, quaternary ammonium bases or their salts, or with protective colloids,-such as glue, gelatine or vegetable mucilages or gums. Salts as for example soda, sodium bicarbonate, waterglass, common salt, neutral or acid sod um sulphate may be added, or organic solvents, such as monocresyl ethylene glycol ether, trichlorethylene or bleaching agents, such as perborates, percarbonates, para-toluene sulphonic chloramide sodium. The said agents are employed in quantities depending on the desired purpose and several of them may be added conjofntly. Thus, for example, the quantity of these additions may be the same as that of the arylides or considerably higher depending on the purposes of emulsifying, wetting, washing, cleaning or dispers'ng solid water-insoluble materials in water. In baths for the treatment of textiles the quantity of the sulphonated arylides may be as low as a few per cent or even a few per thousand of the whole liquors.
All the products accord ng to the present invention must be free from nitro and auxochromic groups, since otherwise they would be inoperative for the different purposes of their application and should preferably contain at least 12 carbon atoms.
The present application is a continuation in part of the application Ser. No. 441,717, filed April.
The following examples will further illustrate how the said invention may be carried out in practice, but the invention is not'restricted to these examples. The parts are by weight.
Example 1 100 parts of' oc-hYdIOXY-iiilll'lC anilide (obtainable by heating a-hydroxy-lauric methyl ester and aniline until the distillat'on of methyl alcohol hasceased) are mixed at about 35 C. with 200 parts of concentrated sulphuric acid and are then treated with parts of fuming sulphuric acid conta ning about 23 percent of S03. The re- (Omiwo-onmi-osomu.)
A similar product can be obtained from di-phenylamine in the place of aniline.
Example 2 1000 parts of a mixture-of saturated fatty acids containing mainly from 12 to 15 carbon atoms and obtained by the liquid phase oxidation of paraifin wax with the aid of air while warming to say 150 C. and separating the acids from unattacked initial material, are heated under reflux with 2000 parts 01' aniline for 17 hours to from 180 to 190 C., the water formed during the reaction being continuously distilled oil. The remainders of free aniline are then distilled off in vacuo and the residue is dissolved in 4,750 parts of sulphuric acid monohydrate. 2200 parts of fuming sulphuric acid containing 23 percent of sulphur trioxide are then introduced into the solution at about 10 C. and the mixture is stirred for about 20 hours at 20 to 25 C. The reaction product isthen poured onto a mixture of ice and common salt and filtered. The product may be employed as such or after neutralization with caustic soda, if desired after removal of the mineral acid salts. sesses a high resistance to acid and a high scouring power superior to that of soaps and is not precipitated from aqueous solutions by means of alkaline earth metals.
I Example 3 500 parts of coconut oil'fatty acid anilide (from nut oil and thus corresponds to the general formula is poured onto ice, rendered neutral with caustic soda and inspissated.
Example 4 14 parts of e-naphthyl-amine are dissolved in 10 parts of pyridine, whereupon 30 parts of ca- It posprylic chloride are added while cooling After warming to about 98 C. for hour under reflux the product is washed with aqueous acetic acid and dried. 20 parts of the caprylic naphthyl amide are dissolved in 19 parts of sulphuric acid mono-hydrate, 40 parts of fuming sulphuric acid containing 23 per cent of S03 are added and the Whole is warmed to from 50 to 60 C. until a sam pie is soluble in water. The reaction mixture is poured onto ice, rendered neutral with caustic soda and inspissated. The product corre- I sponds presumably to the formula Example 5 20 parts of undecylic toluidide are dissolved in 40 parts of sulphuric acid monohydrate and then stirred at from to 120 C. with 40 parts of fuming sulphuric acid containing 23 per cent of S03 until the product is water-soluble, whereupon the latter is poured onto ice, neutralized with 100 aqueous caustic soda solution and inspissated.
Example 6 25 parts of saturated naphthenic (ii-phenylamide, obtainable by acting on a solution of di phenylamine in pyridine with naphthenic chloride (prepared by acting with phosphorus trichloride on commercial saturated napththenic acid) are mixed with 20 parts of sulphuric acid monohydrate at from 10 to 15 C., whereupon 50 parts of fuming sulphuric acid containing 23 per cent of SO: are added and the whole is heated to about 98 C. until a sample is soluble in water. The reaction mixture is poured onto ice, neutralized with aqueous caustic soda and inspissated.
What we claim is:
1. The process for the production of carboxylic arylides containing sulphuric derivative radicles which comprises reacting an aliphatic saturated 120 compound containing the grouping o RC/ x in which X is either halogen o -03, -o-R11o o R being an aliphatic saturated radicle containing from 5 to 15 carbon atoms and R being an aliphatic saturated radicle, which radicles may possess sulphuric ester or sulphonic acid groups, with an aromatic amine free from aliphatic alco- 139 holic and chromophorous groups, but containing at least one hydrogen atom connected to a nitrogen atom which amine may contain sulphuric derivative groups, and if the above initial reacting components do not contain sulphuric ester 143 or sulphonic acid groups, reacting the resulting arylide with a sulphonating agent.
2. The processfor the production of carboxylic arylides containing sulphuric derivative radicles, which comprises reacting an aliphatic saturated 145 compound containing the group in which X denotes or halogen, R being an aliphatic saturated radicle containing from 5 to 15 carbon atoms and R1 being an aliphatic saturated radicle, with an aromatic amine free from aliphatic alcoholic and chromophorous groups but containing at least one hydrogen atom connected to a nitrogen atom, the resulting carboxylic arylide being then reacted with a sulphonating agent.
3. Carboxylic arylides corresponding to the formula in which R-CO denotes an aliphatic saturated radicle containing from 6 to 16 carbon atoms, R1 denotes an aromatic radicle of the benzene or naphthalene series free from aliphatic alcoholic and chromophorous groups and X denotes hydrogen or a radicle as denoted by R1, at least a hydrogen atom of R or R1 being substituted by a sulphonic acid group or at least a hydrogen atom of R being substituted by a sulphuric ester group.
4. Carboxylic arylides corresponding to the formula in which R-CO denotes an aliphatic saturated radicle containing from 6 to 16 carbon atoms, R1 denotes an aromatic radicle free from allphatic alcoholic and chromophorous groups and X denotes hydrogen or a radicle as denoted by R1, at least a hydrogen atom of R or R1 being substituted by a sulphonic acid group or at least a hydrogen atom of R being substituted by a sulphuric ester group.
5. Carboxylic arylides corresponding to th formula I formula in which RC0 denotes an aliphatic saturated radicle containing from 6 to 16 carbon atoms,
-R1 denotes an aromatic radicle free from aliphatic alcoholic and chromophorous groups and X denotes hydrogen or a radicle as denoted by R1, at least one hydrogen atom of R or R1 being substituted by a sulphonic acid group.
7. Carboxylic arylides corresponding to the formula in which RCO denotes an aliphatic saturated radicle containing from 6 to 16 carbon atoms,
R1 denotes an aromatic radicle free from aliphatic alcoholic and chromophorous groups and X denotes hydrogen or a radicle as denoted by R1, at least one hydrogen atom of R and one hydrogen atom of R1 being substituted by sulphonic acid groups.
8. Carboxylic arylides corresponding to the formula in which RCO denotes an aliphatic saturated radicle containing from 6 to 16 carbon atoms, R1 denotes an aromatic mono-nuclear hydrocarbon radicle and X denotes hydrogen or a radicle as denoted by R1, at least a hydrogen atom of R or R1 being substituted by a sulphonic acid group or at least a hydrogen atom of R being substituted by a sulphuric ester group.
9. Mixtures of carboxylic arylides corresponding to the formula 1 in which R-CO denotes the radicles of the fatty acids of coconut oil, R1 denotes an aromatic mono-nuclear hydrocarbon radicle and X denotes hydrogen or a radicle as denoted by R1, at least a hydrogen atom of R or R1 being substituted by a sulphonic acid group or at least a hydrogen atom of R being substituted by a sulphuric ester group.
10. Mixtures of carboxylic arylides corresponding to the formula R -OON R1 in which R--C0 denotes the radicles of the fatty acids of a liquid phase oxidation of paramn wax with the aid of air while warming, R1 denotes an 1 aromatic mono-nuclear hydrocarbon radicle and X denotes hydrogen or a radicle as denoted by R1, at least a hydrogen atom of R or R1 being substituted by a sulphonic acid group or at least a hydrogen atom of R being substituted by a sulphuric ester group.
11. Carboxylic anilides corresponding to the formula x R-CO-N in which R-CO denotes the radicles of the fatty acids of coconut oil, R1 denotes phenyl and X denotes hydrogen or -a radicle as denoted by R1, at least a hydrogen atom of R or R1 being substituted by a sulphonic acid group or at least a hydrogen atom of R being substituted by a sulphuric ester group.
12. A mixture of carboxylic arylides corresponding to the formula spending to the formula in which R-CO denotes the radicles of the fatty in which R-CO denotes the radicles of fatty acids acids of coconut oil, R1 denotes a phenyl 5111- containing from 12 to 15 carbon atoms R1 dephomc acid radicle and X denotes hydrogen. notes a phenylsulphonic acid radicle and X de- 13. A mixture of carboxylic anilides correnotes hydrogen.
FRITZ GUENTHER.
FERDINAND Mt'mz.
HANS HAUSSMANN.
Certificate of Correction Patent No. 1,932,179. October 24, 1933.
FRITZ GUENTHER ET AL,
It is hereby certified that errors appear in the printed specification of the above numbered patent requiring correction as follows: Page 1, line 47, for hydroxy-lourio read hydroxy-lauric; page 3, lines 127-430, claim 1, strike out the formula and insert instead: v
. and line 132, for R read R and that the said Letters Patent should be read with these corrections therein that the .same may conform to the record of the case in the Patent Oflice. v
Signed and'sealed this 1st day of May, D. 1934. 1 v v BRYAN M. BATTEY,
".A0ting 00W sioner of Patents;
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US2967872A (en) * | 1958-12-18 | 1961-01-10 | Procter & Gamble | Process for making acyl taurides |
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US2967872A (en) * | 1958-12-18 | 1961-01-10 | Procter & Gamble | Process for making acyl taurides |
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