US2108901A - Production of assistants for the - Google Patents
Production of assistants for the Download PDFInfo
- Publication number
- US2108901A US2108901A US2108901DA US2108901A US 2108901 A US2108901 A US 2108901A US 2108901D A US2108901D A US 2108901DA US 2108901 A US2108901 A US 2108901A
- Authority
- US
- United States
- Prior art keywords
- products
- mineral
- product
- sulphonation
- assistants
- 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
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000000047 product Substances 0.000 description 33
- 229910052500 inorganic mineral Inorganic materials 0.000 description 22
- 239000011707 mineral Substances 0.000 description 22
- 235000010755 mineral Nutrition 0.000 description 22
- 239000003245 coal Substances 0.000 description 15
- 238000009835 boiling Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000011269 tar Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 8
- 239000004753 textile Substances 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000009736 wetting Methods 0.000 description 6
- 238000006356 dehydrogenation reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011295 pitch Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011339 hard pitch Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- -1 oleum Chemical compound 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000011338 soft pitch Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
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
- C07C309/62—Sulfonated fats, oils or waxes of undetermined constitution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
-
- 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
- the present invention relates to new assistants in the textile and related industries, especially as wetting, washing, dispersing and like agents and a process for producing same.
- wetting, washing, dispersing and like agents can be obtained by sulphonating mixtures of products boiling above 200 C. obtained from mineral coals, such as mineral coal tars, or hydrogenation products of mineral coals or mineral coal tars or dehydrogenation products of the same.
- Especially suitable initial materials are the fractions boiling above 200 C. of the products obtained by the destructive hydrogenation of mineral coals or mineral coal tars while employing superatmospheric pressure for example according to the processes described in Australian Patent No. 1217/26.
- the said fractions may again be separated into single fractions and/or freed from certain nuclear compounds of high molecular weight, such as naphthalene, anthracene, pyrene, chrysene and fluorene, by cooling or extraction with solvents.
- the pitch fractions boiling above 400 C. obtainable by the distillation of mineral coal tars or of the said hydrogenation products boiling above 200 C. or the dehydrogenation products thereof are suitable as initial materials.
- the said pitch fractions are advantageously extracted with solvents, such as carbon disulphide or alcohol, the residue obtained being sulphonated.
- the dehydrogenation of the hydrogenation products of mineral coals or mineral coal tars is carried out by heating the hydrogenation product at temperatures of between 300 and 600 C. in the presence of catalysts, for instance as it is described for example in U. S. Patents 1,913,940 and 1,975,476.
- the sulphonation of the initial materials is effected by employing concentrated sulphuric acid, oleum, sulphur trioxide or chlorsulphonic acid, if desired with an addition of agents combining with water, such as acid anhydrides or acid chlorides, as for example phosphorus pentoxide or acetic anhydride.
- the temperature to be employed for the sulphonation depends on the nature of the initial materials and the nature of the sulphonating agents. Ordinary or increased temperatures, as for example from to 200 C., may be employed.
- the sulphonation can usually be carried out while using mild reaction conditions, for example employing temperatures between 10 and 50 C.
- mild reaction conditions for example employing temperatures between 10 and 50 C.
- products which contain no or only a relatively small amount of unsaturated hydrocarbons it is preferable to employ high temperatures.
- the sulphonation is carried on until the reaction product is partially or Wholly soluble in water.
- the crude sulphonation products obtained are freed from the excess of sulphonating agent and preferably also from unsulphonated and unsulphonatable constituents, neutralized with alkalies, ammonia or amines and the resulting solutions evaporated, if desired to dryness.
- Watersoluble products are obtained which have a high wetting, washing and dispersing power.
- dark colored sulphonation products When dark colored sulphonation products are obtained, they may be rendered lighter in color by treatment with bleaching earths, animal carbon or sodium hypochlorite solution.
- the sulphonation products obtained according to the process as described may be employed advantageously for wetting and washing textiles even in acid baths, furthermore for the preparation of emulsions suitable for impregnating textile materials, leather, paper and the like. Such products as are dark colored may be employed for the preparation of emulsions of bituminous substances.
- the carbon disulphide extract is freed from solvent by distillation and the resulting residue sulphonated in the manner already described after separation of the pyrene and chrysene contained therein.
- the aqueous solution of the sulphonation product is treated with a cold saturated solution of potassium chloride or caustic potash, the resulting potassium salt of the sulphonation product being purified by crystalliza- This product also has a good wetting and dispersing action.
- a process for the manufacture of assistants for the textile and related industries which comprises sulphonating at temperatures of befor the textile and related industries which comprises sulphonating at temperatures of between about 10 and about 200 C. a product obtained by dehydrogenating a product boiling above 200 C. and obtained by hydrogenating a material selected from the group consisting of mineral coals and mineral coal tars.
- a process for the manufacture of assistants for the textile and related industries which comprises sulphonating at temperatures of between about 10 and about 200 C. a product boiling above 200 C. and obtained by hydrogenating a material selected from the group consisting of mineral coals and mineral coal tars which have been freed from condensed polycyclic compounds of high molecular weight by extraction with organic solvents.
- Sulphonation products obtainable by sulphonation at temperatures of between about 10 and about 200 C. of a product boiling above 200 C. and obtained by hydrogenating a material 'selected from the group consisting of mineral coals and mineral coal tars.
- Sulphonation products obtainable by sulphonation at temperatures of between about 10 and about 200 C. of a dehydrogenation product of a product boiling above 200 C. and obtained by hydrogenating a material selected from the group consisting of mineral coals and mineral coal tars.
- a process for the manufacture of assistants for the textile and related industries which comprises causing a sulphonating agent at a temperature between about 10 and about 200 C. to act on a product boiling above 200 C. and obtained by a process comprising hydrogenating a material selected from the group consisting of mineral coals and mineral coal tars.
Description
Patented Feb. 22, 1938 UNITED STATES PATENT QFFECE PRODUCTION OF ASSISTANTS FOR THE TEXTILE AND RELATED INDUSTRIES the-Main, Germany No Drawing. Application May 21, 1935, Serial No. 22,584. In Germany May 30, 1934 6 Claims.
The present invention relates to new assistants in the textile and related industries, especially as wetting, washing, dispersing and like agents and a process for producing same.
We have found that valuable wetting, washing, dispersing and like agents can be obtained by sulphonating mixtures of products boiling above 200 C. obtained from mineral coals, such as mineral coal tars, or hydrogenation products of mineral coals or mineral coal tars or dehydrogenation products of the same.
Especially suitable initial materials are the fractions boiling above 200 C. of the products obtained by the destructive hydrogenation of mineral coals or mineral coal tars while employing superatmospheric pressure for example according to the processes described in Australian Patent No. 1217/26. The said fractions may again be separated into single fractions and/or freed from certain nuclear compounds of high molecular weight, such as naphthalene, anthracene, pyrene, chrysene and fluorene, by cooling or extraction with solvents. Also the pitch fractions boiling above 400 C. obtainable by the distillation of mineral coal tars or of the said hydrogenation products boiling above 200 C. or the dehydrogenation products thereof are suitable as initial materials. The said pitch fractions are advantageously extracted with solvents, such as carbon disulphide or alcohol, the residue obtained being sulphonated.
The dehydrogenation of the hydrogenation products of mineral coals or mineral coal tars is carried out by heating the hydrogenation product at temperatures of between 300 and 600 C. in the presence of catalysts, for instance as it is described for example in U. S. Patents 1,913,940 and 1,975,476.
In the present process the sulphonation of the initial materials is effected by employing concentrated sulphuric acid, oleum, sulphur trioxide or chlorsulphonic acid, if desired with an addition of agents combining with water, such as acid anhydrides or acid chlorides, as for example phosphorus pentoxide or acetic anhydride. The temperature to be employed for the sulphonation depends on the nature of the initial materials and the nature of the sulphonating agents. Ordinary or increased temperatures, as for example from to 200 C., may be employed. When employing products containing a considerable amount of unsaturated hydrocarbons, preferably the dehydrogenation products of mineral coal tars, etc., the sulphonation can usually be carried out while using mild reaction conditions, for example employing temperatures between 10 and 50 C. When products are employed which contain no or only a relatively small amount of unsaturated hydrocarbons it is preferable to employ high temperatures. The sulphonation is carried on until the reaction product is partially or Wholly soluble in water.
The crude sulphonation products obtained are freed from the excess of sulphonating agent and preferably also from unsulphonated and unsulphonatable constituents, neutralized with alkalies, ammonia or amines and the resulting solutions evaporated, if desired to dryness. Watersoluble products are obtained which have a high wetting, washing and dispersing power. When dark colored sulphonation products are obtained, they may be rendered lighter in color by treatment with bleaching earths, animal carbon or sodium hypochlorite solution.
The sulphonation products obtained according to the process as described may be employed advantageously for wetting and washing textiles even in acid baths, furthermore for the preparation of emulsions suitable for impregnating textile materials, leather, paper and the like. Such products as are dark colored may be employed for the preparation of emulsions of bituminous substances.
The following example will further illustrate the nature of this invention but the invention is not restricted to this example.
20 parts of ground mineral coal yielding considerable amounts of gases and burning with large flame (so-called Gasflammkohle) are impregnated with an amount of hydrochloric acid sufiicient to neutralize their alkalinity, dried and triturated to a paste of high consistency with 10 parts or" fused soft pitch (derived from a mineral coal hydrogenation product) having a setting point of 50 C. with an addition of 1 part of ferric oxide gas purifying mass impregnated with ammonium molybdate solution, the temperature being C. The paste is pumped at a temperature of 150 C. through a short wide pipe into and through a pressure-tight reaction vessel provided with a stirrer and hydrogenated therein at 500 C. with hydrogen under a pressure of atmospheres, the reaction materials remaining in the reaction chamber for 20 minutes. After removing the solid ash and coal constituents by centrifuging, the hydrogenation product is distilled to hard pitch with superheated steam under reduced pressure, the oil passing over above 250 C. at 50 millimeters (mercury gauge) being distilled again at the same pressure. When the fraction boiling tion from hot water.
between 250 and 280 C. at the said pressure is allowed to stand, pyrene separates in an amount of 1 per cent of the coal employed.
Example After removing the separated pyrene, the oily product obtained is subjected to fractional distillation and the pitch fraction boiling above 400 C. is extracted in the cold with carbon disulphide. The residue which remains is sulphonated by treatment for two hours with 20 per cent of its weight of 98 per cent sulphuric acid while stirring at 200 C. The reaction mixture is treated with water and freed from acid resin formed by centrifuging. lhe product obtained in this manner is neutralized with caustic potash solution and then toa great extent evaporated. A crystal pulp is obtained which is crystallized from hot water for the purpose of purification. The resulting product has a high wetting power.
The carbon disulphide extract is freed from solvent by distillation and the resulting residue sulphonated in the manner already described after separation of the pyrene and chrysene contained therein. The aqueous solution of the sulphonation product is treated with a cold saturated solution of potassium chloride or caustic potash, the resulting potassium salt of the sulphonation product being purified by crystalliza- This product also has a good wetting and dispersing action.
What we claim is:-
1. A process for the manufacture of assistants for the textile and related industries which comprises sulphonating at temperatures of befor the textile and related industries which comprises sulphonating at temperatures of between about 10 and about 200 C. a product obtained by dehydrogenating a product boiling above 200 C. and obtained by hydrogenating a material selected from the group consisting of mineral coals and mineral coal tars.
3. A process for the manufacture of assistants for the textile and related industries which comprises sulphonating at temperatures of between about 10 and about 200 C. a product boiling above 200 C. and obtained by hydrogenating a material selected from the group consisting of mineral coals and mineral coal tars which have been freed from condensed polycyclic compounds of high molecular weight by extraction with organic solvents.
4. Sulphonation products obtainable by sulphonation at temperatures of between about 10 and about 200 C. of a product boiling above 200 C. and obtained by hydrogenating a material 'selected from the group consisting of mineral coals and mineral coal tars.
5. Sulphonation products obtainable by sulphonation at temperatures of between about 10 and about 200 C. of a dehydrogenation product of a product boiling above 200 C. and obtained by hydrogenating a material selected from the group consisting of mineral coals and mineral coal tars.
6. A process for the manufacture of assistants for the textile and related industries which comprises causing a sulphonating agent at a temperature between about 10 and about 200 C. to act on a product boiling above 200 C. and obtained by a process comprising hydrogenating a material selected from the group consisting of mineral coals and mineral coal tars.
MATHIAS PIER. BRUNO ENGEL.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2108901A true US2108901A (en) | 1938-02-22 |
Family
ID=3429256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2108901D Expired - Lifetime US2108901A (en) | Production of assistants for the |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2108901A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2817679A (en) * | 1955-08-08 | 1957-12-24 | Sinclair Refining Co | Production of basic alkaline earth metal petroleum sulfonates |
-
0
- US US2108901D patent/US2108901A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2817679A (en) * | 1955-08-08 | 1957-12-24 | Sinclair Refining Co | Production of basic alkaline earth metal petroleum sulfonates |
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