US2422613A - Normal secondary tridecyl sulphates - Google Patents
Normal secondary tridecyl sulphates Download PDFInfo
- Publication number
- US2422613A US2422613A US476466A US47646643A US2422613A US 2422613 A US2422613 A US 2422613A US 476466 A US476466 A US 476466A US 47646643 A US47646643 A US 47646643A US 2422613 A US2422613 A US 2422613A
- Authority
- US
- United States
- Prior art keywords
- sulphates
- sulphate
- acids
- carbinol
- fatty acids
- 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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- QTUIJRIDZOSXHJ-UHFFFAOYSA-N tridecyl hydrogen sulfate Chemical group CCCCCCCCCCCCCOS(O)(=O)=O QTUIJRIDZOSXHJ-UHFFFAOYSA-N 0.000 title description 3
- -1 TRIDECYL Chemical group 0.000 description 14
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- 239000010685 fatty oil Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- DWPGOEILRXREMA-UHFFFAOYSA-N 2-methyltetradecan-3-one Chemical compound CCCCCCCCCCCC(=O)C(C)C DWPGOEILRXREMA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 150000005605 isobutyric acids Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- ACMBVSPXQQUNOF-UHFFFAOYSA-N nonadecan-10-ol Chemical compound CCCCCCCCCC(O)CCCCCCCCC ACMBVSPXQQUNOF-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- QCJWNUNXTZOXCF-UHFFFAOYSA-N pentadecan-4-one Chemical compound CCCCCCCCCCCC(=O)CCC QCJWNUNXTZOXCF-UHFFFAOYSA-N 0.000 description 1
- OCPRDMXKEUXQLM-UHFFFAOYSA-N pentadecan-8-yl hydrogen sulfate Chemical class S(=O)(=O)(O)OC(CCCCCCC)CCCCCCC OCPRDMXKEUXQLM-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000004666 short chain fatty acids Chemical class 0.000 description 1
- 235000021391 short chain fatty acids Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ZDAXFBBGLHKLCQ-UHFFFAOYSA-N undecan-4-yl hydrogen sulfate Chemical class S(=O)(=O)(O)OC(CCC)CCCCCCC ZDAXFBBGLHKLCQ-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/06—Hydrogenosulfates
Description
Patented June 17, 1947 NORMAL SECONDARY TRIDECYL SULPI-IATES Emil E. Dreger, Summit, and John Ross, Ramse N. J assignors to Colgate-Palmolive-Peet Company, Jersey City, N. J a corporation of Delaware No Drawing. Original application July 9, 1937,
Serial No. 152,852. Divided and this application February 19, 1943, Serial No. 476,466
4 Claims.
This invention relates to new materials adapted to function as wetting agents, detergents or the like. More particularly, the invention relates to the utilization of short chain fatty acids, which are not ordinarily satisfactory for the preparation of detergents, wetting agents, and the like, for the production of materials which will function emciently for these purposes.
The fatty oils that are commonly used in the production of detergent materials almost invariably contain an appreciable percentage of fatty acid esters, the fatty acids of which contain less than 12 carbon atoms. The sodium salts of these fatty acids are of little or no value and, if they are left in the mixture along with the salts of the higher fatty acids, the result is simply a corresponding amount of inactive or inemcient material in the final product. This fact has been recognized and in some instances these lower fatty acids have been removed to make the final product more effective. The removal of such fatty acids, however, reduces the quantity of the final detergent product that can be produced from a given amount of fatty oil and yields, as a lay-product, considerable quantities of these lower fatty acids. For example, about 21% of the fattyacids in cocoanut oil contains less than 12 carbon atoms, and about 13% of the acids in palm kernel oil also contains less than 12 carbon atoms.
According to the present process, these fatty acids, containing more than 1 and less than 12 carbon atoms and which are almost entirely of the straight chain or normal variety, are reacted in such a way as to form useful, efficient detergents, wetting agents, or the like. Preferably, the fatty acids that are used according to the present process are straight chain fatty acids and have at least 6 and not over 11 carbon atoms.
Briefly, the process of the present invention is acomplished by converting the fatty acids into co-pending application Serial No. 152,852, filed July 9, 1937, now Patent No. 2,321,020, granted June 8, 1943, of which the present application is a division.
The process of the present invention was applied to caproic acid, caprylic acid and capric acid as well as to mixtures of caprlc' and caprylic acids and of all three acids. The individual acids yielded di-n-amyl carbinol sulphate salt, di-nheptyl carbinol sulphate salt, and di-n-nonyl carbinol sulphate salt respectively. The mixture of caprylic and capric acid gave a mixture of di-n-nonyl carbinol sulphate salt, di-n-heptyl carbinol sulphate salt and n-heptyl n-nonyl carbinoi sulphate salt. The mixture of all three acids produced in addition to the others n-amyl n-heptyl carhinol sulphate salt and n-amyl n-noyl carbinol sulphate salt.
The relative wetting and foaming properties of solutions of some of the compounds are compared below, showing the outstanding and unusual emciency of di-n-heptyl c'arbinol sulphate sodium salt in these respects.
Foam, cc. Wetting Time Material 05% in Hard Water 1.0 0.25 500 P. P. M
Di-n-lieptyl carbine] sul hate sodium salt Cu sxOSOaNa n-hep l n-nonyl carblno sul hate sodium Still: 01'! uOSO3NB.
Di-n-nonyl carbinol sul hate sodium salt C10 aOSOaNa Mixed sodium salts of carbinol sulphates from m es 0! Ca, C5, C10 acids a. one inch square of unused canvas drill. By' placing cc. of the solution to be tested in a.
beaker, the time required to wet the square of cloth dropped upon the surface of the solution can be readily measured with a stop watch. In most cases the cloth will sink to the bottom as soon as it is thoroughly wet.
Generally the secondary alcohol sulphates prepared by the process should contain at least 11 carbon atoms to be satisfactory as emulsifying and deterglng agents. That is, if a single acid is used to prepare the secondary alcohol it should contain at least 6 carbon atoms and, if a mixture of acids is used, the sum of the carbons in their chains should be at least equal to 12 carbon atoms. For example, n-butyric acid (4) and n-caprylic acid (8) will yield along with other sulphates, n-propyl n-heptyl carbinol sulphate salt which has 11 carbon atoms in the compound.
Although the preferred compounds are prepared from the straight chain fatty acids containing not less than 6 and not more than 11 carbon atoms, the process is adapted to the use of any straight or branch chain aliphatic monocarboxylic acids other than formic acid. i. e., acetic acid and its higher homologues, whether derived from fatty oils or from any other source, such as the oxidation of petroleum, alcohols and aldehydes, de-esteriflcation of oils, fats and waxes and by organic synthesis.
Mixtures of lauric and n-butyric and of lauric and isobutyric acids were converted into ketones and the pure n-propyl undecyl ketone and isopropyl undecyl ketone obtained by fractionation. These were reduced to the respective carbinols which were converted into acidsulphates and neutralized.
The following comparison of the wetting and foaming properties of these two isomeric compounds discloses the marked superiority of the straight chain compound as a wetting agent.
Foam, 00. @33
Material 9 1 Hunt 1 025 soonr.
Iso ropyl undeoyl carbinol sulgate sodium salt OuHn BO'Na 326 115 13 73 n-propyl undecyl carbinol sulphate sodium salt OuHn OBOINa 300 100 2 22 The present invention is not to be restricted to any specific proportionswr manner of procedure beyond the limitation of the appended claims.
We claim:
1. A normal, secondary, tridecyl sulphate.
2. N-amyl n-heptyl carblnol sulphate.
3. Normal sodium tridecyl-6 sulphate.
4. A salt of a normal, secondary, tridecyl sulphate.
EMIL E. DREGER. JOHN ROSS.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,027,896 Bertsch Jan, 14, 1936 2,229,649 Guenther et a1. Jan. 28, 1941 2,088,018 Wickert et al. July 27, 1937 2,108,133 McCall Feb. 15, 1933 2,326,270 Werntz Aug. 10, 1943 FOREIGN PATENTS Number Country Date 343,872 Great Britain Feb. 9, 1931
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US476466A US2422613A (en) | 1937-07-09 | 1943-02-19 | Normal secondary tridecyl sulphates |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US152852A US2321020A (en) | 1937-07-09 | 1937-07-09 | Detergent and method of making it |
| US476466A US2422613A (en) | 1937-07-09 | 1943-02-19 | Normal secondary tridecyl sulphates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2422613A true US2422613A (en) | 1947-06-17 |
Family
ID=26849915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US476466A Expired - Lifetime US2422613A (en) | 1937-07-09 | 1943-02-19 | Normal secondary tridecyl sulphates |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2422613A (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB343872A (en) * | 1936-02-29 | 1931-02-09 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of wetting, cleansing and dispersing agents |
| US2027896A (en) * | 1929-11-04 | 1936-01-14 | Firm H Th Bohme Ag | Production of alkyl sulphates of high molecular weight |
| US2088018A (en) * | 1934-12-20 | 1937-07-27 | Union Carbide & Carbon Corp | Oxygenated compounds derived from butyraldehyde and its derivatives |
| US2108133A (en) * | 1936-11-25 | 1938-02-15 | Du Pont | Process for producing high molecular alcohols from the corresponding ketones |
| US2229649A (en) * | 1929-04-13 | 1941-01-28 | Gen Aniline & Film Corp | Sulphated methyl heptadecenyl carbinol |
| US2326270A (en) * | 1939-05-27 | 1943-08-10 | Du Pont | Chemical compound and process |
-
1943
- 1943-02-19 US US476466A patent/US2422613A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2229649A (en) * | 1929-04-13 | 1941-01-28 | Gen Aniline & Film Corp | Sulphated methyl heptadecenyl carbinol |
| US2027896A (en) * | 1929-11-04 | 1936-01-14 | Firm H Th Bohme Ag | Production of alkyl sulphates of high molecular weight |
| US2088018A (en) * | 1934-12-20 | 1937-07-27 | Union Carbide & Carbon Corp | Oxygenated compounds derived from butyraldehyde and its derivatives |
| GB343872A (en) * | 1936-02-29 | 1931-02-09 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of wetting, cleansing and dispersing agents |
| US2108133A (en) * | 1936-11-25 | 1938-02-15 | Du Pont | Process for producing high molecular alcohols from the corresponding ketones |
| US2326270A (en) * | 1939-05-27 | 1943-08-10 | Du Pont | Chemical compound and process |
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