US2174110A - bdsnl - Google Patents
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- US2174110A US2174110A US2174110DA US2174110A US 2174110 A US2174110 A US 2174110A US 2174110D A US2174110D A US 2174110DA US 2174110 A US2174110 A US 2174110A
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- US
- United States
- Prior art keywords
- detergent
- compounds
- chlorine
- compound
- treating
- 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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- 150000001875 compounds Chemical class 0.000 description 70
- 239000003599 detergent Substances 0.000 description 48
- 150000002430 hydrocarbons Chemical class 0.000 description 48
- 239000000047 product Substances 0.000 description 44
- OSVXSBDYLRYLIG-UHFFFAOYSA-N Chlorine dioxide Chemical compound O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 description 40
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 40
- 239000004215 Carbon black (E152) Substances 0.000 description 28
- 239000000344 soap Substances 0.000 description 28
- 238000006467 substitution reaction Methods 0.000 description 22
- 239000004155 Chlorine dioxide Substances 0.000 description 20
- -1 alkyl sodium sulphate Chemical compound 0.000 description 20
- 235000019398 chlorine dioxide Nutrition 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- 235000010269 sulphur dioxide Nutrition 0.000 description 20
- 239000004291 sulphur dioxide Substances 0.000 description 20
- 125000004432 carbon atoms Chemical group C* 0.000 description 16
- 239000007795 chemical reaction product Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229920002521 Macromolecule Polymers 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 239000008233 hard water Substances 0.000 description 10
- 230000003301 hydrolyzing Effects 0.000 description 10
- 150000002605 large molecules Chemical class 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000005187 foaming Methods 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000001117 sulphuric acid Substances 0.000 description 8
- 235000011149 sulphuric acid Nutrition 0.000 description 8
- 239000005864 Sulphur Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 239000008246 gaseous mixture Substances 0.000 description 6
- 125000005456 glyceride group Chemical group 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L Calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000001804 emulsifying Effects 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 230000001603 reducing Effects 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 4
- 229910052714 tellurium Inorganic materials 0.000 description 4
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- 235000019482 Palm oil Nutrition 0.000 description 2
- 210000002268 Wool Anatomy 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 239000001175 calcium sulphate Substances 0.000 description 2
- 235000011132 calcium sulphate Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009950 felting Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 230000002140 halogenating Effects 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 150000001455 metallic ions Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000008234 soft water Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 235000019871 vegetable fat Nutrition 0.000 description 2
Classifications
-
- 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
- C07C303/10—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 sulfur dioxide and halogen or by reaction with sulfuryl halides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
Definitions
- This invention relates to detergents and a method of making the same, and has particular reference to detergents that may be used equal- 1y well in hard or soft waters.
- the chief objection to a detergent in the form of an alkyl sodium sulphate is the expense of making the same.
- the formation of such detergent is usually accomplished by reducing the such as found in lard, palm oil, or any of the glycerides, to an alcohol. This reduction is made by treating the acids or glycerides with hydrogen under heat and pressure in the presence of a catalyst, such as palladium or platinum or a combination of the two.
- a catalyst such as palladium or platinum or a combination of the two.
- the alcohol thus formed is then treated with sulphuric acid to form an alkyl sulphate and this, in turn, is treated with a base, such as sodium hydroxide or sodium carbonate to form an alkyl sodium sulphate.
- Another object is to provide a detergent which shall be highly eflicient and which, by reason of its chemical composition, shall have a much greater emulsifying power on oils and greases than ordinary soap or any of the present hard water soaps or detergents.
- a further object is to provide a detergent of the aforesaid character which shall be water soluble and which shall. possess good foaming characteristics.
- the compound or compounds are subjected to the action of chlorine and sulphur dioxide gases, while the temperature is controlled to prevent polymerization of the compound or other internal structural change in the molecules.
- This reaction introduces one or more sulphonic groups into the compound and produces reaction products which are easily hydrolyzed.
- the reaction products thus formed arethen further reacted upon by treating with sulphuric acid or they may be improved by blowing air therethrough. This is speeded up by the addition of water and free chlorine.
- the step of improving the product may be carried out simultaneously with the step of forming the reaction product.
- the compounds thus formed are then treated with a basic reagent such as sodium hydroxide or sodium carbonate to produce a detergent.
- a basic reagent such as sodium hydroxide or sodium carbonate
- the advantage in this method lies not only in the ease and comparatively inexpensive manner of carrying out the above reactions, but also in the fact that the compound or compounds which form the starting point may be hydrocarbons having a relatively large molecule.
- the aforementioned natural fatty acids each have a molecule of 18 or less carbon atoms and form the basis of most present day soaps or detergents.
- compounds such as paramn wax, having a larger molecule and containing more than 18 carbon atoms may be easily reacted upon to produce a detergent having a relatively large molecule.
- This may be accomplished in a number of dif ferent ways, as, for example, by varying the degree of treatment with sulphuric acid or air, by varying the degree of treatment with the basic reagent and by varying the type of basic reagent used.
- the shorter chain hydrocarbons produce the foaming qualities of the detergent at the lower temperatures, while at more elevated -temperatures these shorter chain hydrocarbons lose their foaming properties and the longer chain hydrocarbons produce the foaming qualities.
- the shorter that is, at least five carbon atoms per molecule, or the longer chain hydrocarbons, can be used, or any mixture or combination thereof as may be desired to produce a detergent for any particular use.
- my method is especially applicable to the longer chain hydrocarbons, that is, hydrocarbons having more than 18 carbon atoms to the molecule.
- hydrocarbon-containing compounds in the specification and claims I mean not only pure hydrocarbons and mixtures thereof, but also hydrocarbon derivatives such as fatty acids, animal and vegetable fats and oils and mixtures thereof.
- the substitution products maybeusedinaccordancewiththeaiorementloned orothersimilarrcactionstoprodueea soap or detergent of the desired characteristics.
- the method of forming products containing an atom selected from the group consisting of sulphur, selenium and tellurium, and oxygen and a halogen from hydrocarboncontaining compounds which comprises reacting said compounds witha mixtureofahflblefland a dioxide of an element of the group of sulphur, selenium and tellurium. hrdrolyzing the reaction product, and treating the resultant compound with an oxidizing agent.
- substitution products containing sulphur, oxygen and chlorine from hydrocarbon-containing compounds which comprises reacting said compoimds with a gaseous mixture of chlorine and sulphur dioxide, hydrolyzing the reaction product, and treating the resultant compounds with a free-oxygen containing gas.
- substitution products which comprises reacting a saturated hydrocarbon-containing compound with chlorine and sulphur dioxide, hydrolyzing the reaction product, and treating the resultant compound with air.
- substitution products which comprises reacting a saturated hydrocarbon-containing compound with chlorine and sulphur dioxide, hydrolyzing the reacted compound, and treating said hydrolysed product with sulphuric acid.
- substitution products which compries reacting a saturated hydrocarbon-containing compound with chlorine and sulphur dioxide, and simultaneously hydrolysing the reaction product and treating the reaction product with a free-oxygen containing gas.
- substitution products which comprises reacting a saturated hydrocarbon-containing compound with chlorine and sulphur dioxide and treating said reacted compound with air in the presence of water and free chlorine.
- substitution products which comprises reacting a non-gaseous saturated aliphatic hydrocarbon compound with a mixture of. gaseous chlorine and sulphur dioxide, hydrolyzing said reaction compounds and treating said hydrolysed products with air.
- substitution products which comprises reacting a saturated hydrocarbon-containing compound with gaseous chlorine and sulphur dioxide, treating the resultant compounds with a free-oxygen containing gas, and hydrolyning the treated compounds.
- substitution products in which a satin'ated hydrocarbon-containing compound is treated with a gaseous mixture of chlorine and sulphur dioxide, the step of improving the products by treating said products with air.
- substitution products in which a saturated hydrocarbon-containing compound is treated with a gaseous mixture of chlorine and sulphur dioxide, the step of improving the products by treating said products with a free-oxygen containing gas.
Description
' point is in the form of a natural fatty acids Fatenteci fiepi. 26, 3%39 nn'rancamr aNn men on 2.1-.
seam
Cortes F. Reed, Anoka, half to Charles L. Ho
Kim, mgnor or one- Minneapolis, mm.
No Drawing. Applicafion February 12, 1984,
Serial 10 Claims.
This invention relates to detergents and a method of making the same, and has particular reference to detergents that may be used equal- 1y well in hard or soft waters.
As is well known, ordinary soap is usually the sodium salt of a fatty acid. These soaps function properly in soft water but form insoluble compounds in hard water. processes these insoluble compounds are highly undesirable and form a serious detriment to the successful operation of the process. To overcome this difllculty, a number of hard water detergents have been developed and perhaps one of the most successful from a commercial standan alkyl sodium sulphate. The reaction of this detergent with hard water forms, for the most part, soluble sulphates such as calcium sulphate, which is the principal salt formed, and other metallic sulphates in minor quantities.
The chief objection to a detergent in the form of an alkyl sodium sulphate is the expense of making the same. The formation of such detergent is usually accomplished by reducing the such as found in lard, palm oil, or any of the glycerides, to an alcohol. This reduction is made by treating the acids or glycerides with hydrogen under heat and pressure in the presence of a catalyst, such as palladium or platinum or a combination of the two. The alcohol thus formed is then treated with sulphuric acid to form an alkyl sulphate and this, in turn, is treated with a base, such as sodium hydroxide or sodium carbonate to form an alkyl sodium sulphate.
It is the primary object of the present invention to provide a novel method of forming a new detergent which method shall be simple and inexpensive to carry out and by practicing the same a new detergent shall be formed that is useful equally well in soft or hard waters. That is, the detergent thus formed when used with hard water shall form water soluble salts.
Another object is to provide a detergent which shall be highly eflicient and which, by reason of its chemical composition, shall have a much greater emulsifying power on oils and greases than ordinary soap or any of the present hard water soaps or detergents.
A further object is to provide a detergent of the aforesaid character which shall be water soluble and which shall. possess good foaming characteristics.
The foregoing and other objects and advantages will become more apparent as the description proceeds and will be pointed out in the appended claims.
In carrying out my invention, I react a suitable hydrocarbon-containing compound having either a large molecule (containing a large nun;-
In many industrial- (Ci. With-4W) ber of carbon atoms) or a small molecule, or a mixture of both, such reaction being carried out in accordance with that disclosed in my copending application, entitled Method of halogenating compounds and product resulting therefrom, filed December 29, 1933, Serial No. 704,591 now Patent No. 2,046,090, dated June 30, 1936. As a specific example of such compounds, I refer particularly to the natural fatty acids such as are found in lard, pahn oil, or any of the glycerides, or parailin wax, kerosene, and similar compounds. These may be used singly or in any combination desired and may be represented by the structural where R represents the additional carbon and hydrogen atoms forming the particular molecule or group of molecules in any specific compound.
As disclosed in the aforementioned application, the compound or compounds are subjected to the action of chlorine and sulphur dioxide gases, while the temperature is controlled to prevent polymerization of the compound or other internal structural change in the molecules. This reaction introduces one or more sulphonic groups into the compound and produces reaction products which are easily hydrolyzed. The reaction products thus formed arethen further reacted upon by treating with sulphuric acid or they may be improved by blowing air therethrough. This is speeded up by the addition of water and free chlorine. In actual practice, the step of improving the product may be carried out simultaneously with the step of forming the reaction product.
The compounds thus formed are then treated with a basic reagent such as sodium hydroxide or sodium carbonate to produce a detergent.
The advantage in this method lies not only in the ease and comparatively inexpensive manner of carrying out the above reactions, but also in the fact that the compound or compounds which form the starting point may be hydrocarbons having a relatively large molecule. In other wotds, the aforementioned natural fatty acids each have a molecule of 18 or less carbon atoms and form the basis of most present day soaps or detergents. With my improved method. compounds such as paramn wax, having a larger molecule and containing more than 18 carbon atoms may be easily reacted upon to produce a detergent having a relatively large molecule.
The mechanics of soap as a detergent are not well imderstood. It has been claimed by some that the cleansing eifect is due partially to a solvent action while others claim that the bulkilififisofihealkylgroupwhichisinmoreorless of a colloidal condition envelopes the particles of dirt and includes them in itself. Still others claim that there is an ionization of the salt and a reaction between the metallic ion and that oi. the oils in the dirt particles. The felting of wool is attributed to this property of soap. In all probabilities, the cleansing action of soap is due to a combination of these various properties and such being the case, it follows that the larger the molecule the greater would be the carrying capacity for dirt and the greater its value as a detergent. Hence, by using a hydrocarbon having a relatively large molecule, as, for example, paraffln wax, as contrasted to the usual hydrocarbon of 18 or less carbon atoms, it is obvious that my method of making a detergent produces a superior product.
Another important consideration in connection with my invention lies in the control of the solubility of the detergent. Ordinary soap has an empirical formula of R-COO Na while a typical alkyl sodium sulphate soap has an empirical formula R-O-SOa-Na. In ordinary soap it is the carboxyl group and in the other, the sulphate group which renders the product water soluble, although the sulphate is more soluble than the carboxyl. By being able to use a hydrocarbon having a large molecule, I am able to impart any desired degree of solubility to the detergent. This may be accomplished in a number of dif ferent ways, as, for example, by varying the degree of treatment with sulphuric acid or air, by varying the degree of treatment with the basic reagent and by varying the type of basic reagent used.
It is also well known that the shorter chain hydrocarbons produce the foaming qualities of the detergent at the lower temperatures, while at more elevated -temperatures these shorter chain hydrocarbons lose their foaming properties and the longer chain hydrocarbons produce the foaming qualities. With my method, either the shorter, that is, at least five carbon atoms per molecule, or the longer chain hydrocarbons, can be used, or any mixture or combination thereof as may be desired to produce a detergent for any particular use. As referred to above, my method is especially applicable to the longer chain hydrocarbons, that is, hydrocarbons having more than 18 carbon atoms to the molecule. When these longer chain hydrocarbons are used, as, for example, one having 24 carbon atoms, a detergent is produced that is water soluble, and while not producing so voluminous a foam as the shorter chain hydrocarbo nevertheless, the foam produced is longer lived even at very elevated temperatures and the emulsifying powers on oils and greases is approximately fifty times that of ordinary soap and about ten times that of an ordinary alkyl sodium sulphate soap.
While I have disclosed parainn wax and kerosene as specific examples of relatively long chain hydrocarbons, I do not limit myself to these particular compounds as I may halogenate other compoimds to eifect substitution products as disclosed in my aforementioned copending application. Thus by hydrocarbon-containing compounds" in the specification and claims I mean not only pure hydrocarbons and mixtures thereof, but also hydrocarbon derivatives such as fatty acids, animal and vegetable fats and oils and mixtures thereof. The substitution products maybeusedinaccordancewiththeaiorementloned orothersimilarrcactionstoprodueea soap or detergent of the desired characteristics.
What I claim is:
1. The method of forming products containing an atom selected from the group consisting of sulphur, selenium and tellurium, and oxygen and a halogen from hydrocarboncontaining compounds which comprises reacting said compounds witha mixtureofahflblefland a dioxide of an element of the group of sulphur, selenium and tellurium. hrdrolyzing the reaction product, and treating the resultant compound with an oxidizing agent.
2. The method of forming substitution products containing sulphur, oxygen and chlorine from hydrocarbon-containing compounds which comprises reacting said compoimds with a gaseous mixture of chlorine and sulphur dioxide, hydrolyzing the reaction product, and treating the resultant compounds with a free-oxygen containing gas.
3. The method of forming substitution products which comprises reacting a saturated hydrocarbon-containing compound with chlorine and sulphur dioxide, hydrolyzing the reaction product, and treating the resultant compound with air.
4. The method of forming substitution products which comprises reacting a saturated hydrocarbon-containing compound with chlorine and sulphur dioxide, hydrolyzing the reacted compound, and treating said hydrolysed product with sulphuric acid.
5. The method of forming. substitution products which compries reacting a saturated hydrocarbon-containing compound with chlorine and sulphur dioxide, and simultaneously hydrolysing the reaction product and treating the reaction product with a free-oxygen containing gas.
6. The method of forming substitution products which comprises reacting a saturated hydrocarbon-containing compound with chlorine and sulphur dioxide and treating said reacted compound with air in the presence of water and free chlorine.
'1. The method of forming substitution products which comprises reacting a non-gaseous saturated aliphatic hydrocarbon compound with a mixture of. gaseous chlorine and sulphur dioxide, hydrolyzing said reaction compounds and treating said hydrolysed products with air.
8. The method of forming substitution products which comprises reacting a saturated hydrocarbon-containing compound with gaseous chlorine and sulphur dioxide, treating the resultant compounds with a free-oxygen containing gas, and hydrolyning the treated compounds.
9. In the method 01 forming substitution products in which a satin'ated hydrocarbon-containing compound is treated with a gaseous mixture of chlorine and sulphur dioxide, the step of improving the products by treating said products with air.
10. In the method oi forming substitution products in which a saturated hydrocarbon-containing compound is treated with a gaseous mixture of chlorine and sulphur dioxide, the step of improving the products by treating said products with a free-oxygen containing gas.
CORT I. REED.
Publications (1)
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US2174110A true US2174110A (en) | 1939-09-26 |
Family
ID=3430690
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US2174110D Expired - Lifetime US2174110A (en) | bdsnl |
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Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2454827A (en) * | 1947-02-21 | 1948-11-30 | Sonneborn Sons Inc L | Viscosity reduction of petroleum mahogany sulfonate hydrocarbon solutions |
US2462341A (en) * | 1949-02-22 | Cleaning composition for rust | ||
DE765194C (en) * | 1940-02-25 | 1951-08-09 | Henkel & Cie Gmbh | Process for the production of mixtures of sulfonic acids and sulfuric acid esters or their salts |
DE831733C (en) * | 1949-01-06 | 1952-02-18 | Dr Willy Weiss | Detergents and cleaning agents |
US2702273A (en) * | 1949-12-06 | 1955-02-15 | Helen Muriel Kennedy | Production of organic sulphonic acids |
US2766276A (en) * | 1951-04-25 | 1956-10-09 | Ruhrchemie Ag | Neutralization of sulfonic acids |
US2974094A (en) * | 1958-05-16 | 1961-03-07 | Exxon Research Engineering Co | Radio-sulfochlorination of paraffins |
US3000831A (en) * | 1957-07-22 | 1961-09-19 | Monsanto Chemicals | Detergent compositions |
DE1242220B (en) * | 1960-09-20 | 1967-06-15 | Bayer Ag | Process for the production of alkyl sulfonates or alkyl sulfonic acid esters with high thermal stability and low color from petroleum fractions |
US4904401A (en) * | 1988-06-13 | 1990-02-27 | The Lubrizol Corporation | Lubricating oil compositions |
US4938881A (en) * | 1988-08-01 | 1990-07-03 | The Lubrizol Corporation | Lubricating oil compositions and concentrates |
US4952328A (en) * | 1988-05-27 | 1990-08-28 | The Lubrizol Corporation | Lubricating oil compositions |
US5366648A (en) * | 1990-02-23 | 1994-11-22 | The Lubrizol Corporation | Functional fluids useful at high temperatures |
US20070123437A1 (en) * | 2005-11-30 | 2007-05-31 | Chevron Oronite Company Llc | Lubricating oil composition with improved emission compatibility |
WO2013070347A1 (en) | 2011-11-11 | 2013-05-16 | Chevron Oronite Company Llc | Glycerol-containing functional fluid |
WO2013074155A1 (en) | 2011-11-15 | 2013-05-23 | Chevron Oronite Company Llc | Glycerol-containing functional fluid |
US8796192B2 (en) | 2010-10-29 | 2014-08-05 | Chevron Oronite Company Llc | Natural gas engine lubricating oil compositions |
US8841243B2 (en) | 2010-03-31 | 2014-09-23 | Chevron Oronite Company Llc | Natural gas engine lubricating oil compositions |
US8969273B2 (en) | 2009-02-18 | 2015-03-03 | Chevron Oronite Company Llc | Lubricating oil compositions |
-
0
- US US2174110D patent/US2174110A/en not_active Expired - Lifetime
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2462341A (en) * | 1949-02-22 | Cleaning composition for rust | ||
DE765194C (en) * | 1940-02-25 | 1951-08-09 | Henkel & Cie Gmbh | Process for the production of mixtures of sulfonic acids and sulfuric acid esters or their salts |
US2454827A (en) * | 1947-02-21 | 1948-11-30 | Sonneborn Sons Inc L | Viscosity reduction of petroleum mahogany sulfonate hydrocarbon solutions |
DE831733C (en) * | 1949-01-06 | 1952-02-18 | Dr Willy Weiss | Detergents and cleaning agents |
US2702273A (en) * | 1949-12-06 | 1955-02-15 | Helen Muriel Kennedy | Production of organic sulphonic acids |
US2766276A (en) * | 1951-04-25 | 1956-10-09 | Ruhrchemie Ag | Neutralization of sulfonic acids |
US3000831A (en) * | 1957-07-22 | 1961-09-19 | Monsanto Chemicals | Detergent compositions |
US2974094A (en) * | 1958-05-16 | 1961-03-07 | Exxon Research Engineering Co | Radio-sulfochlorination of paraffins |
DE1242220B (en) * | 1960-09-20 | 1967-06-15 | Bayer Ag | Process for the production of alkyl sulfonates or alkyl sulfonic acid esters with high thermal stability and low color from petroleum fractions |
US4952328A (en) * | 1988-05-27 | 1990-08-28 | The Lubrizol Corporation | Lubricating oil compositions |
US4904401A (en) * | 1988-06-13 | 1990-02-27 | The Lubrizol Corporation | Lubricating oil compositions |
US4938881A (en) * | 1988-08-01 | 1990-07-03 | The Lubrizol Corporation | Lubricating oil compositions and concentrates |
US5366648A (en) * | 1990-02-23 | 1994-11-22 | The Lubrizol Corporation | Functional fluids useful at high temperatures |
US20070123437A1 (en) * | 2005-11-30 | 2007-05-31 | Chevron Oronite Company Llc | Lubricating oil composition with improved emission compatibility |
US7981846B2 (en) | 2005-11-30 | 2011-07-19 | Chevron Oronite Company Llc | Lubricating oil composition with improved emission compatibility |
US8969273B2 (en) | 2009-02-18 | 2015-03-03 | Chevron Oronite Company Llc | Lubricating oil compositions |
US8841243B2 (en) | 2010-03-31 | 2014-09-23 | Chevron Oronite Company Llc | Natural gas engine lubricating oil compositions |
US8796192B2 (en) | 2010-10-29 | 2014-08-05 | Chevron Oronite Company Llc | Natural gas engine lubricating oil compositions |
WO2013070347A1 (en) | 2011-11-11 | 2013-05-16 | Chevron Oronite Company Llc | Glycerol-containing functional fluid |
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