US2423692A - Normal secondary nonadecyl sulphates - Google Patents
Normal secondary nonadecyl sulphates Download PDFInfo
- Publication number
- US2423692A US2423692A US488558A US48855843A US2423692A US 2423692 A US2423692 A US 2423692A US 488558 A US488558 A US 488558A US 48855843 A US48855843 A US 48855843A US 2423692 A US2423692 A US 2423692A
- Authority
- US
- United States
- Prior art keywords
- carbinol
- sulphates
- sulphate
- fatty acids
- salt
- 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
- JKTVUKBHRRIGSI-UHFFFAOYSA-N nonadecyl hydrogen sulfate Chemical group CCCCCCCCCCCCCCCCCCCOS(O)(=O)=O JKTVUKBHRRIGSI-UHFFFAOYSA-N 0.000 title description 4
- -1 NONADECYL SULPHATES Chemical class 0.000 description 14
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000003599 detergent Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 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
- 150000003839 salts Chemical class 0.000 description 3
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 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
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 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
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- NDCORKBQGDAFNT-UHFFFAOYSA-M [Na+].S(=O)(=O)([O-])OC(CCCCCCCCC)CCCCCCCCC Chemical compound [Na+].S(=O)(=O)([O-])OC(CCCCCCCCC)CCCCCCCCC NDCORKBQGDAFNT-UHFFFAOYSA-M 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- CSMFSDCPJHNZRY-UHFFFAOYSA-N decyl hydrogen sulfate Chemical class CCCCCCCCCCOS(O)(=O)=O CSMFSDCPJHNZRY-UHFFFAOYSA-N 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 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
- KAYMRANHJDGOQZ-UHFFFAOYSA-N heptadecan-8-ol Chemical compound CCCCCCCCCC(O)CCCCCCC KAYMRANHJDGOQZ-UHFFFAOYSA-N 0.000 description 1
- 150000005605 isobutyric acids Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- ACMBVSPXQQUNOF-UHFFFAOYSA-N nonadecan-10-ol Chemical compound CCCCCCCCCC(O)CCCCCCCCC ACMBVSPXQQUNOF-UHFFFAOYSA-N 0.000 description 1
- UZZYXUGECOQHPU-UHFFFAOYSA-N octyl hydrogen sulfate Chemical class CCCCCCCCOS(O)(=O)=O UZZYXUGECOQHPU-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 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
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 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
- 239000011734 sodium Substances 0.000 description 1
- MSDGJRHNSCDTHJ-UHFFFAOYSA-M sodium pentadecan-8-yl sulfate Chemical compound S(=O)(=O)(OC(CCCCCCC)CCCCCCC)[O-].[Na+] MSDGJRHNSCDTHJ-UHFFFAOYSA-M 0.000 description 1
- WFRKJMRGXGWHBM-UHFFFAOYSA-M sodium;octyl sulfate Chemical compound [Na+].CCCCCCCCOS([O-])(=O)=O WFRKJMRGXGWHBM-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VARQGBHBYZTYLJ-UHFFFAOYSA-N tricosan-12-one Chemical compound CCCCCCCCCCCC(=O)CCCCCCCCCCC VARQGBHBYZTYLJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 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
-
- 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
- C07C305/08—Dialkylsulfates; Substituted dialkylsulfates
Definitions
- 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,
- 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 ineflicient 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 eflective.
- 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.
- 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;
- the process of the present invention is accomplished by converting the fatty acids into ketones, usually straight chain ketones since the fatty acids used are generally straight chain fatty acids; thereafter hydrogenating the ketones to form secondary alcohols; and finally sulphating the alcohols to produce secondary alcohol sulphuric acid esters.
- the acid esters may then be neutralized with lime, ammonia, alkali metal hydroxides or carbonates before use.
- Di-n-heptyl carbinol sulphate sodium salt GisHsiO SOQNE 600 1 2 1O n-Heptyl n-nonyl carbinol sulgiate sodium salt C11 :50 S0;Na 400 20 2 9 Di-n-nonyl carbinol sulhate sodium salt 819E390 SO3N8 275 10 9 50 Mixed sodium salts of carbinol sulphates from mixtures of Ca, 0
- the secondary alcohol sulphates pre pared by the process should contain at least 11 carbon atoms to be satisfactory as emulsifying and deterging agents. is used to preparethe 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.
- 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.
- the preferred compounds are prepared from the straight chainfatty acids con- That is, if a single acid taming not less than 6 and not more than 11 carbon atoms, the process is adapted to the use of i any straight or branch chain aliphatic monocarboxylic acids other than formic acid, 1. e., acetic 4
- the present invention is not to be'restricted to any specific proportions or manner of procedure beyond the limitation of the appended claims.
- a normal secondary nonadecyl sulphate from fatty oils or from any other source, such as 2.
- Di-n-nonyl carbinol sulphate salt Di-n-nonyl carbinol sulphate salt.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
Description
Patented July 8,1947
NORMAL. ssconmuty NONADECYL SULPHATES Emil. E. Dreger, Summit, and John Ross Ramsey,
assignors to Colgate-Paimoiive-Peet Company, Jersey City, N. 1., a corporation of Delaware No Drawing. Original applieation luiy e, 1937,
Serial No. 152,852. Divided and this application May 26, 1943, Serial No. 488,558
6 Claims. 1 v 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 efficiently 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 ineflicient 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 eflective.
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 by-product, considerable quantities of these lower fatty acids. For example,v about 21% of the fatty acids in coconut 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 accomplished by converting the fatty acids into ketones, usually straight chain ketones since the fatty acids used are generally straight chain fatty acids; thereafter hydrogenating the ketones to form secondary alcohols; and finally sulphating the alcohols to produce secondary alcohol sulphuric acid esters. The acid esters may then be neutralized with lime, ammonia, alkali metal hydroxides or carbonates before use. The process is further described and is claimed in our copending application Serial No. 152,852, filed July 9, 1937, now Patent No. 2,321,020, granted June 8,
Q 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 carbinol sulphate salt. The mixture of all three acids produced in addition to the others n-amyl nheptyl carbinol sulphate salt and n-amyl n-nonyl carbinol sulphate salt.
The relative wetting and foaming properties of solutions ofsome of the compounds are compared below, showing the outstanding and unusual efilciency of di n-heptyl carbinol sulphate sodium salt in these respects.
Foam, cc. Wetting Time Material &2}?
1% Water, 1.0% 0.25% 0.1%
tion 500 P. P. M.
Di-n-heptyl carbinol sulphate sodium salt GisHsiO SOQNE 600 1 2 1O n-Heptyl n-nonyl carbinol sulgiate sodium salt C11 :50 S0;Na 400 20 2 9 Di-n-nonyl carbinol sulhate sodium salt 819E390 SO3N8 275 10 9 50 Mixed sodium salts of carbinol sulphates from mixtures of Ca, 0|, Cm acids 350 60 2 17 1943, of which the present application is a divin-heptyl carbinol sulphate salt, and-di-n-nonyl 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 pre pared by the process should contain at least 11 carbon atoms to be satisfactory as emulsifying and deterging agents. is used to preparethe 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 chainfatty acids con- That is, if a single acid taming not less than 6 and not more than 11 carbon atoms, the process is adapted to the use of i any straight or branch chain aliphatic monocarboxylic acids other than formic acid, 1. e., acetic 4 The present invention is not to be'restricted to any specific proportions or manner of procedure beyond the limitation of the appended claims.
We claim:
acid and its higher homologues, whether derived 5 1. A normal secondary nonadecyl sulphate. from fatty oils or from any other source, such as 2. Di-n-nonyl carbinol sulphate. the oxidation of petroleum, alcohols and alde- 3. A normal secondary nonadecyl sulphate hydes, de-esterification of oils, fats and waxes salt. and by organic synthesis. 4. Di-n-nonyl carbinol sulphate salt.
Mixtures of lauric and n-butyric and of lauric 5. A normal secondary nonadecyl sulphate soand isobutyric acids were converted into ketones dium salt. and the pure n-propyi undecyl ketone and 150- 6. Di-n-nonyl carbinol sulphate sodium salt. propyl undecyl ketoneobtained by fractionation. EMI EL DRE These were reduced to the respective carbinols JOHN Ross, which were converted into acid sulphates and neutralized. REFERENCES CITED following comparison of the Wetting and The following references are of record in the foaming properties of these two isomeric comm of this patent: pounds discloses the marked superiority of the straight chain compound as a wetting agent. UNITED STATES PATENTS Number Name Date Foam m Wetting 2,027,896 Bertsch Jan. 14, 1936 Time 2,229,649 Guenther et a1 Jan 28, 1941 2,326,270 Werntz Aug. 10, 1943 2,103,133 McCall Feb. 15,1938 tion age 2,088,019 Wickert July 27, 1937 FOREIGN PATENTS Number Country Date $2.122 533 ?;i? "c.. I 343,872 Great Britain Feb. 3, 1931 i l iiaafiman-rm: 73 0 n phat? sodium salt CnHu THEE REFERENCES 0503M 2 22 Messer, Chem. News, vol. 138, pp. 292-3
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US488558A US2423692A (en) | 1937-07-09 | 1943-05-26 | Normal secondary nonadecyl 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 |
US488558A US2423692A (en) | 1937-07-09 | 1943-05-26 | Normal secondary nonadecyl sulphates |
Publications (1)
Publication Number | Publication Date |
---|---|
US2423692A true US2423692A (en) | 1947-07-08 |
Family
ID=26849917
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US488558A Expired - Lifetime US2423692A (en) | 1937-07-09 | 1943-05-26 | Normal secondary nonadecyl sulphates |
Country Status (1)
Country | Link |
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US (1) | US2423692A (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 |
US2088019A (en) * | 1934-12-29 | 1937-07-27 | Union Carbide & Carbon Corp | Secondary alkyl sulphates as wetting agents |
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
- 1943-05-26 US US488558A patent/US2423692A/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 |
US2088019A (en) * | 1934-12-29 | 1937-07-27 | Union Carbide & Carbon Corp | Secondary alkyl sulphates as wetting agents |
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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