US2121845A - Process for producing clear lightcolored, water-soluble sulphonation products of mineral oil - Google Patents

Process for producing clear lightcolored, water-soluble sulphonation products of mineral oil Download PDF

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Publication number
US2121845A
US2121845A US705918A US70591834A US2121845A US 2121845 A US2121845 A US 2121845A US 705918 A US705918 A US 705918A US 70591834 A US70591834 A US 70591834A US 2121845 A US2121845 A US 2121845A
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United States
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oil
water
sulphur
sulphonation
soluble
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Expired - Lifetime
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US705918A
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English (en)
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Wernicke Erich Arnold
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Individual
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Individual
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Priority to US158915A priority Critical patent/US2172149A/en
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    • 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

Definitions

  • This invention relates to a process for the pr duction of sulphonation products from sulphurbearing mineral oils, tar oils, and the like, i. e.
  • oils containing about 2 per cent and more 5 of sulphur from oils containing about 2 per cent and more 5 of sulphur.
  • sulphonation products from mineral oils, tar oils, etc. are used for many purposes, as for instance for the preparation of. emulsions, for general technical purposes, or for the manufacture of pharmaceutical preparations and the like.
  • a sulphur content, for instance, of 10% corresponds to a-content of sulphur compounds of approximately 50-60%, so that the experiences had with oils having less than 2% of sulphur, which can still be fairly classified as hydrocarbons, cannot simply be applied to the sulphur oils involved herein.
  • a light-colored oil may, in the subsequentsulphonation, produce a dark resinous product. It is, therefore, an object to remove, by pre-refinement, all those oil substances which would cause a dark coloration of the final sulphonation product, retaining, nevertheless, as much as possible the original sulphur compounds.
  • the present invention solves this task in such a manner that the oils or their distillates, or singular fractions, are liberated, by a chemical 65 pre-refinement, from the ingredients that might Germany January 11,
  • the ore-refinement can be carriedv out, for instance, with soda lye or with sulphuric acid,
  • the pre-refinement can also be carried out with other known refining agents which may be used either alone or combined, depending on the chemical character of the oil, thus, for instance, with potash lye, aluminum chloride, phosphoric acid, fullers earth, bleaching clay, and
  • sulphur-bearing petroleum or other oils for instance from Italian mineral coal, Middle-German brown coal, South- German bituminous shale, orsimilar combinations or mixtures may be used with equal advantage for the manufacture of such sulphonation products.
  • Analogous deposits of coal-like materials which are equally suitable for the process according to this invention on account of their sulphurcontent are found in all parts of the world. Practically it is, of course, preferable to.
  • Example 1 As starting material a distilled Italian mineral coal-tar, having the following characteristics, is used: specific weight at 15 C. about 0.9; sulphur content 8.8%; boiling points about -250. 100 grams of this oil are pre-refined with soda lye of 39 B., sulphuric acid of 70% H2804 and fullers earth. The sulphur content after the prerefinement is 10.22%.
  • the refinedoil is now sulphonated with about 60 cc. sulphuric acid of 90% H2804 under stirring and cooling at 0 C.
  • the sulphonation mixture is run into water, and sulpho-acid and oil are then neutralized with ammonia. After separating the oil, the product is evaporated to a water content of 41.24%. 10 grams are obtained of this product, which, in this condition, contains 6.84% of ammonium sulphate and 9.57% of sulphur.
  • the organic substance .is 51.92% including 15.24% of sulphur. It has been calculated that the oil substance which has been sulphonated contains 11.01% of organic sulphur.
  • the product is light-brown, transparent and clearly watersoluble.
  • reaction products of the oil and sulphuric acid obtained in the end product are true sulpho-acids and not esters because the latter would be split by the strong heating which takes place in the dilution of the sulphonation product with water and in the evaporation of the water from the neutralized product.
  • Example 2 As starting material a distilled Italian mineral coal-tar is used having the following character-,
  • the product is then evaporated to a water content of 42%. 69 grams of this product are obtained. In this condition it contains 11% of ammonium sill-- phate and 10.62% of sulphur. The organic substance therein is 47.%, including 16.92% of sulphur. It has been calculated that the oil' substance which has' been sulphonated contains 10.38% of organic sulphur.
  • the product is light- -brown, transparent and clearly water-soluble.
  • a distilled Mid-German brown coal-gas-light oil is used having the fol-. lowing characteristics: specific weight at 15 C. 0.850; sulphur content 6.0%; boiling analysis:
  • Example 5 As starting material a distilled Tyrolean shale oil is used refined with 35% soda'lye, 70% sullowing characteristics: specific weight at 15 C. 0.894; sulphur content 11.45%; boiling analysis:
  • sulphonation mixture is run into water and sulpho-acid and oil are neutralized with ammonia. After removal of the unaffected part of the oil, having become separated by the dilution with water, the product is evaporated to a water content of 50%.. 816 grams of this product are obtained which, in this condition, contain 10.95% of ammonium sulphate and 10.60% of sulphur. It has been calculated that the sulphonated oil substance contains 2.8% of organic sulphur. The product is light-brown, transparent and clearly water-soluble.
  • water-soluble sulphonation products of mineral oils naturally containing more than two per cent of organically combined sulphur, without substantially impairing such natural organically combined sulphur content which comprises selectively separating out of such oils the inherent resinifiable materials by treatment with a mineral acid of the group consisting of sulphuric acid and phosphoric acid, the concentration of said refining acid being adjusted substantially within the range of 50 to 70 percent for sul-' phuric acid, according to the quality of the oil treated; subsequently carefully sulphonating the treated oils at greatly reduced temperatures of C. and less with concentrated sulphuric acid; thereafter dissolving out the soluble portion of the sulphur-rich sulphonation products thus obtained in water and neutralizing the solution.
  • a process for producing light colored, water-soluble sulphonation products of Tyrolean shale oil having a relatively high natural sul- .phur content of over 2% which comprises the after dissolving the soluble portion of the sulphur-rich sulphonation products thus obtained in water and neutralizing the solution with ammonia.
  • a process for producing light-colored, clearly Water-soluble sulphonation products of Tyrolean shale oil having a'relatively high natural sulphur content of more than 2% which comprises the steps of selectively separating out of said oils, before sulphonation, the inherent resinifiable materials without substantially impairing the natural organically combined sulphur content by treating the oil first with 35% soda lye, then with 70% sulphuric acid, and then with fullers earth; sulphonating the oil with 96% sulphuric acid at about -8 0., adding the sulphonation mixture to water and neutralizing the sulpho-acid and oil by treatment with ammonia; removing the unsulphonated oil which separates by dilution with the water, adding thereto an equal amount of new oil and about 10% more than an equal part of acid, stirring the mixture at about 15 C., running the sulphonation mixture into water, and neutralizing the su'lpho-acid and oil with ammonia.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
US705918A 1933-01-11 1934-01-09 Process for producing clear lightcolored, water-soluble sulphonation products of mineral oil Expired - Lifetime US2121845A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US158915A US2172149A (en) 1934-01-09 1937-08-13 Sulphonated mineral oils rich in sulphur content

Applications Claiming Priority (1)

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DE2121845X 1933-01-11

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US2121845A true US2121845A (en) 1938-06-28

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US705918A Expired - Lifetime US2121845A (en) 1933-01-11 1934-01-09 Process for producing clear lightcolored, water-soluble sulphonation products of mineral oil

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US (1) US2121845A (de)
AT (1) AT151008B (de)
CH (1) CH173409A (de)
GB (1) GB432797A (de)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2689862A (en) * 1951-04-20 1954-09-21 Monsanto Chemicals Improvement in color of aryl alkane sulfonates
US2691040A (en) * 1951-03-29 1954-10-05 Universal Oil Prod Co Sulfonation of organic compounds with sulfur trioxide
US2746987A (en) * 1952-09-15 1956-05-22 Bray Oil Co Sulfonate manufacture
EP0450201A1 (de) * 1989-12-21 1991-10-09 ENIRICERCHE S.p.A. Verfahren zur Herstellung sulfonierter Dispergiermittel aus Erdölasphaltfraktionen
US20040020108A1 (en) * 2002-08-05 2004-02-05 Arpad Savoly Dispersant composition

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2691040A (en) * 1951-03-29 1954-10-05 Universal Oil Prod Co Sulfonation of organic compounds with sulfur trioxide
US2689862A (en) * 1951-04-20 1954-09-21 Monsanto Chemicals Improvement in color of aryl alkane sulfonates
US2746987A (en) * 1952-09-15 1956-05-22 Bray Oil Co Sulfonate manufacture
EP0450201A1 (de) * 1989-12-21 1991-10-09 ENIRICERCHE S.p.A. Verfahren zur Herstellung sulfonierter Dispergiermittel aus Erdölasphaltfraktionen
US5322556A (en) * 1989-12-21 1994-06-21 Eniricerche S.P.A. Process for preparing a sulfonated dispersant from petroleum asphalt fractions
US20040020108A1 (en) * 2002-08-05 2004-02-05 Arpad Savoly Dispersant composition
US6863837B2 (en) * 2002-08-05 2005-03-08 Geo Specialty Chemicals, Inc. Dispersant composition
US20050171324A1 (en) * 2002-08-05 2005-08-04 Geo Specialty Chemicals, Inc. Dispersant composition

Also Published As

Publication number Publication date
GB432797A (en) 1935-08-02
AT151008B (de) 1937-10-11
CH173409A (de) 1934-11-30

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