US2049670A - Foaming agents - Google Patents
Foaming agents Download PDFInfo
- Publication number
- US2049670A US2049670A US2049670DA US2049670A US 2049670 A US2049670 A US 2049670A US 2049670D A US2049670D A US 2049670DA US 2049670 A US2049670 A US 2049670A
- Authority
- US
- United States
- Prior art keywords
- reaction
- alcohols
- alcohol
- product
- wetting
- 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
- 239000004088 foaming agent Substances 0.000 title 2
- 235000019441 ethanol Nutrition 0.000 description 66
- AKEJUJNQAAGONA-UHFFFAOYSA-N Sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 56
- 238000000034 method Methods 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000007795 chemical reaction product Substances 0.000 description 32
- 150000001298 alcohols Chemical class 0.000 description 30
- 239000000047 product Substances 0.000 description 30
- 238000009736 wetting Methods 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000011780 sodium chloride Substances 0.000 description 24
- 239000003599 detergent Substances 0.000 description 22
- 239000000463 material Substances 0.000 description 22
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 150000002148 esters Chemical class 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- -1 aliphatic alcohols Chemical class 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 14
- 239000003995 emulsifying agent Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 230000001804 emulsifying Effects 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 235000019864 coconut oil Nutrition 0.000 description 8
- 239000003240 coconut oil Substances 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229910001510 metal chloride Inorganic materials 0.000 description 8
- LQZZUXJYWNFBMV-UHFFFAOYSA-N Dodecanol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 125000004432 carbon atoms Chemical group C* 0.000 description 6
- 150000001805 chlorine compounds Chemical class 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 230000003472 neutralizing Effects 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000005591 charge neutralization Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000001264 neutralization Effects 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 235000014593 oils and fats Nutrition 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- NINIDFKCEFEMDL-AKLPVKDBSA-N (35)S Chemical compound [35S] NINIDFKCEFEMDL-AKLPVKDBSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 240000007170 Cocos nucifera Species 0.000 description 2
- 206010022114 Injury Diseases 0.000 description 2
- 229940116985 POTASSIUM LAURYL SULFATE Drugs 0.000 description 2
- ONQDVAFWWYYXHM-UHFFFAOYSA-M Potassium lauryl sulfate Chemical compound [K+].CCCCCCCCCCCCOS([O-])(=O)=O ONQDVAFWWYYXHM-UHFFFAOYSA-M 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- PHIIYDSPMYGDAF-UHFFFAOYSA-N S(=O)(=O)(O)O.C(CCCCCCCCCCC)[K] Chemical compound S(=O)(=O)(O)O.C(CCCCCCCCCCC)[K] PHIIYDSPMYGDAF-UHFFFAOYSA-N 0.000 description 2
- 229940035295 Ting Drugs 0.000 description 2
- UYPYRKYUKCHHIB-UHFFFAOYSA-N Trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 description 2
- IYOXCZOCKKLYDH-UHFFFAOYSA-M [K+].[O-]S(Cl)(=O)=O Chemical compound [K+].[O-]S(Cl)(=O)=O IYOXCZOCKKLYDH-UHFFFAOYSA-M 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical class 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000008233 hard water Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 229910052573 porcelain Inorganic materials 0.000 description 2
- 239000001184 potassium carbonate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 230000001256 tonic Effects 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
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C303/08—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 halogenosulfonic acids
-
- 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
Description
Patented Aug. 4, 193a murscruan or ws-rrma sun some scams Arnon O. Snoddy and Wilfred 8.
Cincin- Martin. nati, Ohio, assignors to The Procter dz Gamble Oompany, Cincinnati, Ohio. a corporation of Ohio *No Drawing. Appli Serial No. 646,708. rose cation December 10, 1933,
Renewed January 17,
ricmm. (c1. sec-sale) This invention relates to a process for producing wetting and foaming agentsconsisting essentially of metallic salts or the sulfuric esters of alcohols by the direct union of alcohols with the 5 reaction products of sulfur trioxide on metallic chlorides. Its object is to provide a practical. convenient, and economical process for the production 01 such products. Many oi the metallic salts of alkyl sulfuric esters have valuable wet-- l ting, emulsifying, and detergent properties, es-
pecially those containing from 12 to 22 carbon atoms, such as may be obtained from the alcohols made, from oils and fats by known means.
The usual procedure in the past for producing l the above mentioned compounds has been to first produce the acid sulfuric ester 01' the alcohol, which in this case was usually an aliphatic alcohol, and then to neutralize same by treatment with oxides, mrdroxides, or carbonates of the go metals to form the desired salts. The sulfuric esters have usually been previously formed in such cases by the reaction of. aliphatic alcohols with concentrated sulfuric acid in excess or by the reaction of aliphatic alcohols with chlor-sul- 25 tonic acid. In the latter case, it is not necessary to use such a large excess of the acid, and in practice it is round that as much as 90% or 95% of the alcoholused can be converted into the sulfuric ester. 30 our improvement arises from the discovery that good wetting agentsconsisting of metallic salts of sulfuric esters of higher alcohols can be made directly by the reaction between such alcohols and the product obtained by action of sulfur 35 trioxide on alkali chlOl'ldB Oi. similar chlorides.
The treatment of sodium chloride or other chloride with sulfur trioxide is. not a part of the present invention.
We find that when a higher alcohol is mixed 40 ,with the reaction products of sulfur trioxide on metallic chlorides. a; chemical reaction takes place with the evolution of hydrochloric acid gas,
and there is formed a metallic salt of the sulfuric I ester-of the alcohol. Various salts may be used, 45 especially those of the alkali metals, the alkali earth metals or ammonium, as well as various .other metals. It is possible in this reaction to.
have thelarger part of the alcohol converted into the sulfuric ester without using a large ex- 50 cess of the said reaction products oi sulfur triox ably to grind it in a suitable apparatus, such as a ball mill, during the progress oi the reaction. in this way, the reacting material may be kept in intimate contact. Another method for facilitating the progress of the reaction is to use an in- 5 ert liquid medium in which the materials can be dissolved or suspended and thereby kept in intimate contact. Carbon tetrachloride and various other chlorinated hydrocarbons, such as dichlorethane, may be used for this purpose. )0
It is obvious that the reaction may be carried out either with a single alcohol or a mixture of alcohols. Mixtures of the higher alcohols suitable for this purpose may be obtained by known procedures from the commercial oils and fats, is which will produce alcohols having carbon contents varying usually between 12 and 22 carbon atoms.
Hereinafter in'these specifications, for the purpose of fully disclosing an exemplary embodiment of our invention, we shall describe a process of producing compounds from higher aliphatic alcohols', it being understood that our invention is not restricted to aliphatic alcohols.
At the end of the reaction referred to. the metal 25 sulfuric ester may be purified from the other materials, such as unconverted raw materials and small amounts of by-products in various known ways such as by dissolving the mass in a suitable solvent and allowing it to crystallize either by cooling the solution or by the removal of a portion of the solvent by evaporation. We have found that a suitable method is to wash the crude product with a solvent in which the impurities are more soluble than is the metallic salt of the sulfuric ester. The purified material, when dissolved in water, shows remarkable wetting, sudsing. emulsifying and detergent properties.
In carrying out this invention in its exemplary form. we proceed as follows:
One hundred parts of an aliphatic alcohol, such as lauryl alcohol, may be used together with 84 parts of finely ground reaction products of sulfuric anhydride on potassium chloride. The lauryl alcohol is placed in any suitable mixing or grinding device, such as a ball mill constructed of acid-prooi'material, such as porcelain, for example, and suitably arranged to allow evolution of the hydrochloric acid gas formed in the reac-- tion and also immersed in a water bath or provided with other arrangement for cooling. The reacting materials must be substantially anhydrous andcare must be taken to avoid contact with moisture. The potassium reaction products above mentioned are added to the alcohol in small portions at a time and mixed, or ground in the mill, to effect the desired reaction while the temperature is controlled so that the reacting mixture does notreach too high a temperature,- preferably not higher than about 30 C. Excessively high temperatures form undesired products. The reaction is allowed to continue until no further action takes place, at which time it is found that about 90 .to 95% of the alcohol is used up. The mass is then discharged from the mixer or mill and should preferably then be neutralized, and purified if necessary, as follows:
If the material is to be used for purposes not requiring a high degree of purity, it may be mixed with about one-third to one-half its weight of water containing a, small excess of potassium hydroxide or carbonate over that required for complete neutralization of the free acid remaining in the mix. This forms a pasty mass which shows the characteristic valuable detergent, wetting and emulsifying properties when mixed with water, and is especially useful for these purposes in hard water or in sea water. If a dry product is desired instead of the paste, it may be dried by any'of the ordinary procedures, such as are used for drying soap, for example, or after suitable dilution with additional water, it may be dried by the spray drying procedure.
If a purer product than the above is required, the mixture may be discharged into a suitable solvent, such as ethyl alcohol, containing a slight excess of potassium hydroxide over that necessary to neutralize the acidity of the discharged mixture. Suflicient alcohol should be used in this case to dissolve the potassium lauryl sulfate, and the hot alcoholic solution is then filtered from insoluble impurities and cooled to allow the pure lauryl potassium sulfate to crystallize out. After separating the crystallized material, as by any suitable means, further amounts of the product may be obtained by evaporating ofl some of the alcohol and again allowing the solution to cool and crystallize.
Another procedure which may be used for purifying the product is to discharge the mass from the ball mill into ethyl or other suitable alcohol containing potassium hydroxide in slight excess over that required to neutralize the free acid, and then filter and evaporate off the solvent alcohol, preferably at a low temperature to avoid injury to the product, and also preferably using means. Alcohols obtained from cocoanut oil and tallow, for example, have been found to produce very satisfactory products by our procedure.
Instead of using the potassium salt of the said reaction products with sulfur trioxide, it is also possible to use V the sodium salt, the ammonium salt, and salts of other metals; those of the alkali group and the alkali earth group are especially suitable. When other bases than potassium are used, it is, of course, understood that the same base will ordinarily be used in the subsequent neutralization. It is also understood that the quantities above mentioned for use with lauryl alcohol and potassium chlor-sulfonate will be modified when other materials are used in order to have the proper relation of their chemical reacting weights. Both saturated and unsaturated alcohols, may be used in this reaction.
Instead of carrying out the reaction as above described, thealcohols may be mixed with from one to five times their weight of carbon tetrachloride or dichlorethane, etc. in an acid-proof mixing vessel. The necessary weight of the previously described reaction products is then stirred into the mixture gradually while keeping the temperature of the mass preferably below approximately 30" C. and allowing the hydrochloric acid gas which is formed in the reaction to escape. When the reaction is completed, the mixture is transferred to a distilling apparatus where the inert liquid medium is distilled ofl, using preferably a low temperature and vacuum. The product may then be neutralized and purified by any of the procedures above mentioned. The product is-the same as that obtained by using the first described procedure.
Having thus described our invention, what we claim as new and desire to secure by LettersPatent is:
1. The process of making a wetting and sudsing agent which comprises causing a higher al- 001101 to react with the reaction product of sulfur trioxide on a metal chloride.
2. The process of making a material whose water solution has good wetting, sudsing, emulsifying and detergent properties, which consists in causing a mixture of higher aliphatic alcohols to react with the reaction products of sulfur trioxide on a metal chloride.
3. The process of making a material whose water solution has good wetting, sudsing, emulsifying and detergent properties, which comprises causing one or more higher aliphatic alcohols to react with the reaction product of sulfur trioxide on a metal chloride.
4. The process of making a wetting, sudsing, emulsifying and detergent agent, which comprises reacting a higher aliphatic alcohol with the reaction product of sulfur trioxide on a metal chloride, neutralizing the product and purifying the same by washing out impurities with a suitable solvent.
5. The process of making a wetting, sudsing, emulsifying and detergent agent, which comprises reacting the alcohols obtained by hydrogenation of coconut oil with the reaction product of sulfur trioxide on sodium chloride, in the presence of an inert liquid medium.
6. The process of making a wetting, sudsing, emulsifying and detergent agent, which comprises reacting the alcohols derived from coconut oil with the reaction product of sulfur trioxide on sodium chloride, in the presence of an inert liquid medium.
'7. The process of making a wetting, sudsing, emulsifying and detergent agent, which comprises reacting the alcohols obtained by hydrogenation of coconut oil with the reaction product of sulfur trioxide on sodium chloride, neutralizing the product and purifyingthe same by washing out the impurities with a suitable solvent.
8. The process of making a wetting, sudsing, emulsifying and detergent agent, which comprises reacting the alcohols derived from coconut oil with the reaction product of sulfur trioxide on sodium chloride, neutralizing the product and with a suitable solvent.
the product and purifying same by dissolving in a suitable solvent, filtering the solution and recrystallizing said agent from said suitable solvent.
11. The process of making a wetting, sudsing, emulsifying and detergent agent, which comprises causing alcohols characterized by the presence or molecules having from twelve to twenty-two carbon atoms each, to react with the reaction product of sulfur trioxide on a metal 10 chloride.
ARNON O. SNODDY. WILFRED S. MARTIN.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2049670A true US2049670A (en) | 1936-08-04 |
Family
ID=3428077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2049670D Expired - Lifetime US2049670A (en) | Foaming agents |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2049670A (en) |
-
0
- US US2049670D patent/US2049670A/en not_active Expired - Lifetime
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