US1968796A - Agent for wetting - Google Patents
Agent for wetting Download PDFInfo
- Publication number
- US1968796A US1968796A US61405332A US1968796A US 1968796 A US1968796 A US 1968796A US 61405332 A US61405332 A US 61405332A US 1968796 A US1968796 A US 1968796A
- Authority
- US
- United States
- Prior art keywords
- mixture
- wetting
- agent
- alcohols
- alcohol
- 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
- 238000009736 wetting Methods 0.000 title description 4
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000001117 sulphuric acid Substances 0.000 description 6
- 235000011149 sulphuric acid Nutrition 0.000 description 6
- 235000013162 Cocos nucifera Nutrition 0.000 description 5
- 244000060011 Cocos nucifera Species 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 230000001804 emulsifying effect Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- -1 aliphatic alcohols Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229940043348 myristyl alcohol Drugs 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 235000019488 nut oil Nutrition 0.000 description 1
- 239000010466 nut oil Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D1/00—Fire-extinguishing compositions; Use of chemical substances in extinguishing fires
- A62D1/0071—Foams
Definitions
- the instant invention comprehends sulphuric reaction products of the fatty alcohols such as those obtained from cocoanut and palm nut oils.
- sulphuric reaction products as used herein, includes sulphuric acid esters, sulphonic acids and mixtures or combinations of the same in any desired proportion.
- the principal object of the present invention is to provide agents of the above nature which are excellently adapted for the many purposes herein later set forth, and which are producible from raw materials at low cost by a minimum number of operations.
- These agents are most conveniently produced by reacting sulphuric acid or its equivalent with fatty alcohols, such as those produced from cocoanut oil by esterifying the fatty acids derived therefrom with lower aliphatic alcohols and reducing the mixture of esters to alcohols.
- fatty alcohols such as those produced from cocoanut oil
- the higher boiling fraction of the distillate consists mainly of myristic and octodecyl alcohols.
- the sulphuric reaction products obtainable from this fraction are also satisfactory for the purposes 5 for which the product is intended but not to as high a degree as those derived from the lower boiling fraction.
- the whole distillate or either fraction thereof may be treated with any sulphonating or sulphating agent including concentrated or fuming sulphuric acid, sulphur trioxide, or chlorosulphonic acid, either alone or, if desired, together with a dehydrating media of organic or inorganic nature.
- any sulphonating or sulphating agent including concentrated or fuming sulphuric acid, sulphur trioxide, or chlorosulphonic acid, either alone or, if desired, together with a dehydrating media of organic or inorganic nature.
- reaction product as to whether it is an ester, a sulphonate or a mixture thereof is obviously dependent upon the intensity of the sulphonation or sulphating conditions, such as the character and quantity of the sulphonating or sulphating agent and the temperature maintained during the reaction.
- Example 1 A mixture of fatty alcohols consisting principally of lauric alcohol is obtained from cocoanut oil by esterification of the fatty acids with ethyl alcohol, reduction of the ethyl ester, distillation of the reduced product and collection of the first 50 to 60% of the distillate. This mixture in a quantity of 100 kgs. is melted at a temperature of about 30 C. and treated with 50 kgs. of chlorosulphonic acid at the said temperature.
- Example 2 A mixture of alcohols obtained as described in the above example, in a quantity of 100 kgs. is treated with kgs. of fuming sulphuric acid at a temperature of 100 C.
- reaction products of the above processes are directly neutralized by means of soda lye and then separated by known methods from inorganic impurities, such as sodium sulphate or sodium chloride.
- the products of the present invention and in particular those obtained from the mixture composed largely of lauric alcohol are very stable, are very soluble in water, and are excellent for moistening and foaming purposes in many commercial processes, such as those employed in the textile, leather, pharmaceutical, ceramic and metal working industries.
- the products are also suitable for use in manufacturing insecticides and dust binding agents and as a foaming agent in fire extinguishers, in which case 5% of the product is added to a 10% solution of sodium bicarbonate to be reacted in the extinguisher with sulphuric acid.
- the products are useful in substantially all processes wherein there is involved moistening, permeating, emulsifying, cleaning, softening, introducing active substances or forming protective colloids.
- a medium for wetting, permeating and producing foam and dispersion comprising a mixture of true sulphonates 01 primary myristyl alcohol and primary octadecyl alcohol.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Business, Economics & Management (AREA)
- Emergency Management (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Colloid Chemistry (AREA)
Description
Patented July 31, 1934 UNITED STATES PATENT OFFICE AGENT FOR WETTING, EMULSIFYING, ETC.
Heinrich Bertsch, Chemnitz, Germany, assignor, by mesne assignments, to American Hyalsol Corporation, Wilmington, Del., a corporation of Delaware No Drawing. Original application March 6, 1930, Serial No. 433,815. Divided and this application May 27, 1932, Serial No. 614,053.
dia adapted for wetting, emulsifying and like purposes. This application is a division of Ser. No.
433,815, filed March 6, 1930, relating to the preparation of these agents.
More particularly, the instant invention comprehends sulphuric reaction products of the fatty alcohols such as those obtained from cocoanut and palm nut oils. The phrase sulphuric reaction products as used herein, includes sulphuric acid esters, sulphonic acids and mixtures or combinations of the same in any desired proportion.
The principal object of the present invention is to provide agents of the above nature which are excellently adapted for the many purposes herein later set forth, and which are producible from raw materials at low cost by a minimum number of operations.
These agents are most conveniently produced by reacting sulphuric acid or its equivalent with fatty alcohols, such as those produced from cocoanut oil by esterifying the fatty acids derived therefrom with lower aliphatic alcohols and reducing the mixture of esters to alcohols. Instead of using the whole mixture of alcohols from the cocoanut oil, it is preferred to employ only the lower boiling portion thereof such as the first 50 to 60% of a distillate collected during distillation of the mixture. This portion of the distillate consists principally of lauric alcohol.
The higher boiling fraction of the distillate consists mainly of myristic and octodecyl alcohols. The sulphuric reaction products obtainable from this fraction are also satisfactory for the purposes 5 for which the product is intended but not to as high a degree as those derived from the lower boiling fraction.
In the production of the product, the whole distillate or either fraction thereof may be treated with any sulphonating or sulphating agent including concentrated or fuming sulphuric acid, sulphur trioxide, or chlorosulphonic acid, either alone or, if desired, together with a dehydrating media of organic or inorganic nature.
The nature of the reaction product as to whether it is an ester, a sulphonate or a mixture thereof is obviously dependent upon the intensity of the sulphonation or sulphating conditions, such as the character and quantity of the sulphonating or sulphating agent and the temperature maintained during the reaction.
Herein follow some examples of methods by which the products of the present invention may be prepared. It is to be understood, however, that the sulphuric reaction products as disclosed and In Germany claimed herein may be produced by other processes from lauric and related fatty alcohols.
Example 1 A mixture of fatty alcohols consisting principally of lauric alcohol is obtained from cocoanut oil by esterification of the fatty acids with ethyl alcohol, reduction of the ethyl ester, distillation of the reduced product and collection of the first 50 to 60% of the distillate. This mixture in a quantity of 100 kgs. is melted at a temperature of about 30 C. and treated with 50 kgs. of chlorosulphonic acid at the said temperature.
Example 2 A mixture of alcohols obtained as described in the above example, in a quantity of 100 kgs. is treated with kgs. of fuming sulphuric acid at a temperature of 100 C.
The reaction products of the above processes are directly neutralized by means of soda lye and then separated by known methods from inorganic impurities, such as sodium sulphate or sodium chloride.
The true sulphonic acids of the fatty alcohols obtained by energetic sulphonation at elevated temperatures, as has been described in Example 2 above, are extremely valuable in the treatment of fibrous material, for the reason that they do not split off sulphuric acid even during the drying and calendering of the textile at elevated temperatures. Ordinary or unstable sulphuric reaction products of fats and oils used for sizing purposes break up splitting off sulphuric acid, with the result that frequently the fibers are injured.
The products of the present invention, and in particular those obtained from the mixture composed largely of lauric alcohol are very stable, are very soluble in water, and are excellent for moistening and foaming purposes in many commercial processes, such as those employed in the textile, leather, pharmaceutical, ceramic and metal working industries. The products are also suitable for use in manufacturing insecticides and dust binding agents and as a foaming agent in fire extinguishers, in which case 5% of the product is added to a 10% solution of sodium bicarbonate to be reacted in the extinguisher with sulphuric acid. In fact the products are useful in substantially all processes wherein there is involved moistening, permeating, emulsifying, cleaning, softening, introducing active substances or forming protective colloids.
Having thus described the invention, what is ducing foam and dispersion comprising true phonates or the lower boiling alcohols obtained from cocoanut oil.
5. A true sulphonate or primary myri styl alcohol. g
"6. Atrue sulphonate of primary octadecyl alcohol. 1
7. A medium for wetting, permeating and producing foam and dispersion comprising a mixture of true sulphonates 01 primary myristyl alcohol and primary octadecyl alcohol.
v HEINRICH BERTSCH.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US700355A US2114042A (en) | 1928-03-30 | 1933-11-29 | Sulphuric derivatives of higher alcohols |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1929B0142353 DE686332C (en) | 1929-03-06 | 1929-03-06 | Wetting agents, foaming agents and dispersants |
| US433815A US1968794A (en) | 1929-03-06 | 1930-03-06 | Process of making sulphuric reaction products of aliphatic alcohols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1968796A true US1968796A (en) | 1934-07-31 |
Family
ID=25968774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US61405332 Expired - Lifetime US1968796A (en) | 1928-03-30 | 1932-05-27 | Agent for wetting |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1968796A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2934451A (en) * | 1945-03-14 | 1960-04-26 | William W Prichard | Anti-vesicant coating composition |
| US2956947A (en) * | 1957-08-06 | 1960-10-18 | Union Carbide Corp | Fire extinguishing method |
| US3003971A (en) * | 1944-04-06 | 1961-10-10 | Du Pont | Stabilized tertiary n-chlorourea compositions |
| US4612991A (en) * | 1985-03-18 | 1986-09-23 | Phillips Petroleum Co. | Oil recovery process |
-
1932
- 1932-05-27 US US61405332 patent/US1968796A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3003971A (en) * | 1944-04-06 | 1961-10-10 | Du Pont | Stabilized tertiary n-chlorourea compositions |
| US2934451A (en) * | 1945-03-14 | 1960-04-26 | William W Prichard | Anti-vesicant coating composition |
| US2956947A (en) * | 1957-08-06 | 1960-10-18 | Union Carbide Corp | Fire extinguishing method |
| US4612991A (en) * | 1985-03-18 | 1986-09-23 | Phillips Petroleum Co. | Oil recovery process |
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