US2654772A - 2-(1, 3, 3-trimethylbutyl)-5, 7, 7-trimethyl octanol-1-sulfate - Google Patents
2-(1, 3, 3-trimethylbutyl)-5, 7, 7-trimethyl octanol-1-sulfate Download PDFInfo
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- US2654772A US2654772A US160587A US16058750A US2654772A US 2654772 A US2654772 A US 2654772A US 160587 A US160587 A US 160587A US 16058750 A US16058750 A US 16058750A US 2654772 A US2654772 A US 2654772A
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- Prior art keywords
- sulfate
- trimethylbutyl
- alcohol
- primary
- alcohols
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- IHIUHVGBAJIGNG-UHFFFAOYSA-N [2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctyl] hydrogen sulfate Chemical compound CC(C)(C)CC(C)CCC(COS(O)(=O)=O)C(C)CC(C)(C)C IHIUHVGBAJIGNG-UHFFFAOYSA-N 0.000 title claims 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 24
- -1 1,3,3-TRIMETHYLBUTYL Chemical class 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 238000005882 aldol condensation reaction Methods 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000003138 primary alcohols Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- WTPYRCJDOZVZON-UHFFFAOYSA-N 3,5,5-Trimethylhexanal Chemical compound O=CCC(C)CC(C)(C)C WTPYRCJDOZVZON-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000742 Cotton Polymers 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
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000019635 sulfation Effects 0.000 description 2
- 238000005670 sulfation reaction Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YSSVMXHKWSNHLH-UHFFFAOYSA-N octadecenal Natural products CCCCCCC=CCCCCCCCCCC=O YSSVMXHKWSNHLH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance 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
-
- 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 novel, highly branched, sulfated primary octadecyl alcohol compositions which are of value as surface-active agents.
- An object of the present invention is to provide, from readily available sources, a sulfated, primary alcohol which is suitable for use as a surface-active agent, and which is useful for other purposes. Other objects of the invention will appear hereinafter.
- the present invention provides, as a novel composition of matter, a sulfated, highlybranched primary octadecanol; the invention is based in part upon the discovery that the nonylheptylmethyl primary carbinols of the formula (C9H19)(C'1H15)CH-CH2OH have outstanding properties as intermediates for high speed wetting agents.
- This octadecyl alcohol composition thus differs from previously known higher alcohols in a. surprising manner.
- this octadecanol is much more highly branched than any of the previously disclosed primary alcohols of similar molecular weight, it is indeed quite remarkable that it nevertheless can be converted to a sodium alkyl sulfate which has outstanding properties as a high speed wetting agent, and which, in fact, is far superior in wetting power to the best previously known straight-chain sodi- 2 um alkyl sulfates of similar molecular weight in that it is readily soluble in organic solvents. For example, it dissolves readily in hydrocarbons such as benzene which are non-solvents for the straight-chain sodium alkyl sulfonates.
- Octadecyl alcohol Preparation of 3,5,5-trimethylhexanal is disclosed in copending application S. N. 758,477, filed July 1, 1947, now abandoned.
- This aldehyde is obtained by reacting carbon monoxide and hydrogen with diisobutylene in the presence of a. cobalt catalyst at elevated temperatures and pressures (cf. S. N. 598,208, filed June 7, 1945, now Patent No. 2,437,600).
- the structural formula of the chief aldol condensation products of 113,5,5-trimethylhexanal can be represented as folows:
- the monohydric primary octadecanol obtained in the practice of this invention is a. nonylheptyl methyl primary carbinol
- the purified octadecyl alcohol was a water-white oil of refractive index boiling point 146/7 mm. or 141 C./3 mm. It was insoluble in water, but was soluble in methanol, ethanol, acetone, benzene, cyclohexane, and dioxane.
- This octadecyl alcohol was converted to the sodium alkyl sulfate by reaction with an equimolar quantity of chlorosulfonic acid followed by neutralization with sodium hydroxide. The reaction with chlorosulfonic acid was carried out by slowly adding the chlorosulfonic acid to the alcohol at 25 to 40 .C. with stirring.
- the sodium alkyl sulfate thus obtained (namely sodium 2 (1,3,3-trimethy1butyl) -5,7,7 trimethyloctanol-l sulfate) was tested to determine its wetting power, i. e. the minimum concentration (grams/liter) in water which is required to cause a standardized skein of cotton to sink in .25 seconds. Comparative tests were made with wellknown commercial surface-active agents. The results were as follows:
- any suitable hydrogenation catalyst may be employed, as disclosed in copending application S. N. 598,208, filed June 7, 1945.
- the aldol condensation of the C9 aldehyde can be efiected by means of any suitable catalyst, e. g. any alkaline substance.
- Any suitable hydrogenation catalyst may be employed in the hydrogenation of the aldol condensation product.
- the sulfation of the alcohol can be carried out by any suitable method, such as by reacting the alcohol at 25 to C.
- dioxane-SOe complex formed by passing gaseous sulfur dioxide into a chilled mixture of dioxane and ethylene dichloride.
- the neutralization of the sulfate may be accomplished by employing ammonia, ethanolamine, diethanolamine, triethanolamine, morpholine, lime, calcium carbonate, magnesia, magnesium carbonate, alkali metal hydroxides orany other similar neutralizing agent.
- Dilute neutralizing agents e. g. 3% NaOH in water, are preferred.
- the sodium octadecyl sulfate can be isolated readily in the form of a dry, white, rather flaky watersoluble solid, by evaporation of water from the neutralized sulfated product. Since the procedure for condensation of the C9 aldehyde, hy-
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Oct. 6, 1 953 2- (1,3,3-TRIMETHYLBUTYL) -5,7,7-TRI- DIETHYL OCTANOL-l-SULFATE Albert A. Pavlic, Wilmington, Del., assignor to E. I. du Pont de Nemours and Company, Wilmington, DeL, a corporation of Delaware No Drawing. Application May 6, 1950, Serial No. 160,587
2 Claims.
This invention relates to novel, highly branched, sulfated primary octadecyl alcohol compositions which are of value as surface-active agents. This application is a continuation-inpart of my copending application S. N. 791,939, filed December 1'7, 1947, now abandoned.
For many years, important uses have existed for relatively high molecular weight alcohols, particularly those containing about 18 carbon atoms per molecule. To meet these important needs,- especially in the detergent field, straightchain alcohols have been manufactured on a rather large scale by hydrogenation of fatty acids or esters. The literature contains apparently conflicting statements as to the relative merits .of straight chain versus branched chain alcohols as intermediates for making surface-active agents. (Compare French Patent 805,706 and A. P. C. patent application S. N. 369,507 with U. S. 2,422,613 and Ind. Eng. Chem. 35, 111 (1943). The very highly branched chain primary alcohols, with which the present invention is concerned, were not known prior to my invention,
and they had not been investigated as possible detergent intermediates prior to my invention. The question whether these very highly branched, primary alcohols could be employed successfully in place of the previously-known, longchain alcohols in the manufacture of sodium alkyl sulfate surface-active agents therefore remained unanswered.
An object of the present invention is to provide, from readily available sources, a sulfated, primary alcohol which is suitable for use as a surface-active agent, and which is useful for other purposes. Other objects of the invention will appear hereinafter.
The present invention provides, as a novel composition of matter, a sulfated, highlybranched primary octadecanol; the invention is based in part upon the discovery that the nonylheptylmethyl primary carbinols of the formula (C9H19)(C'1H15)CH-CH2OH have outstanding properties as intermediates for high speed wetting agents. This octadecyl alcohol composition thus differs from previously known higher alcohols in a. surprising manner. Since this octadecanol is much more highly branched than any of the previously disclosed primary alcohols of similar molecular weight, it is indeed quite remarkable that it nevertheless can be converted to a sodium alkyl sulfate which has outstanding properties as a high speed wetting agent, and which, in fact, is far superior in wetting power to the best previously known straight-chain sodi- 2 um alkyl sulfates of similar molecular weight in that it is readily soluble in organic solvents. For example, it dissolves readily in hydrocarbons such as benzene which are non-solvents for the straight-chain sodium alkyl sulfonates.
The highly branched octadecanol of this invention is obtained by a process represented by the following equations:
3,5,5-Trimethylhexana1 Aldol condensation product (Nonyl aldehyde) Aldol condensation product CsHi1CHzCH(C1Hi5)CH:OH
Octadecyl alcohol Preparation of 3,5,5-trimethylhexanal is disclosed in copending application S. N. 758,477, filed July 1, 1947, now abandoned. This aldehyde is obtained by reacting carbon monoxide and hydrogen with diisobutylene in the presence of a. cobalt catalyst at elevated temperatures and pressures (cf. S. N. 598,208, filed June 7, 1945, now Patent No. 2,437,600). The structural formula of the chief aldol condensation products of 113,5,5-trimethylhexanal can be represented as folows:
Hydrogenation of the latter condensation product converts the CH0 group to methylol. Thus the monohydric primary octadecanol obtained in the practice of this invention is a. nonylheptyl methyl primary carbinol,
(C9H19) (C'IH15)CH-CH2OH The main ingredient evidently has the structure 5 cm on, E10 CH; cm CHz()-CH47HOH:CHz-$H'IHCH:-CH:
i. e. it is 2-(l,3,3-trimethylbutyl)-5,'7,'7-trimethyloctanol-l. The invention is illustrated further by means of the following example.
ErampZe.A mixtu'ie of 1611.0 grams (11.35 mols) of 3,5,5-trimethylhexanal and 100.0 grams (5.6% by weight) of piperidine acetate catalyst was heated at 98 C. with stirring during 7 hours. After standing during 63 hours at 98 C. the re action mixture was distilled under reduced pressure. The fraction boiling in the range 124 to 140 C./4.5 mm. amounted to 855 grams, corresponding to a 56.6% conversion to octadecenal.
Most of this aldol condensation product (weight 842 grams) was hydrogenated with 5.3% by weight of nickel-on-kieselguhr as catalyst. Hydrogenation was conducted at 700 atmospheres pressure, 155 to 160 C. during one hour. Fractional distillation of the combined filtered reaction mixture resulted in 661 grams of product boiling over the range 120 to 148 C./6 mm. and varying in refractive index (11, from 1.4510 to 1.4502. This weight corresponds to a conversion of 83%. Further purification was effected by a rehydrogenation treatment followed by a distillation recovery, resulting in octadecyl alcohol of hydroxyl number=206.0 (99+%), free carbonyl number:0.0, combined carbonyl number:3.0. The purified octadecyl alcohol was a water-white oil of refractive index boiling point 146/7 mm. or 141 C./3 mm. It was insoluble in water, but was soluble in methanol, ethanol, acetone, benzene, cyclohexane, and dioxane. This octadecyl alcohol was converted to the sodium alkyl sulfate by reaction with an equimolar quantity of chlorosulfonic acid followed by neutralization with sodium hydroxide. The reaction with chlorosulfonic acid was carried out by slowly adding the chlorosulfonic acid to the alcohol at 25 to 40 .C. with stirring. The sodium alkyl sulfate thus obtained (namely sodium 2 (1,3,3-trimethy1butyl) -5,7,7 trimethyloctanol-l sulfate) was tested to determine its wetting power, i. e. the minimum concentration (grams/liter) in water which is required to cause a standardized skein of cotton to sink in .25 seconds. Comparative tests were made with wellknown commercial surface-active agents. The results were as follows:
The tests with soft water set forth in the example show that the sodium octadecyl sulfate prepared from the octadecanol of this invention is more effective in wetting cotton than the best commercially available surface-active agents.
It is to be understood that the foregoing example is illustrative only and that it should not be considered as limiting the invention. In the "preparation of the C9 aldehyde by carbonylation of diisobutylene, any suitable hydrogenation catalyst may be employed, as disclosed in copending application S. N. 598,208, filed June 7, 1945. Similarly, the aldol condensation of the C9 aldehyde can be efiected by means of any suitable catalyst, e. g. any alkaline substance. Any suitable hydrogenation catalyst may be employed in the hydrogenation of the aldol condensation product. The sulfation of the alcohol can be carried out by any suitable method, such as by reacting the alcohol at 25 to C. for about one hour with dioxane-SOe complex (formed by passing gaseous sulfur dioxide into a chilled mixture of dioxane and ethylene dichloride). and the neutralization of the sulfate may be accomplished by employing ammonia, ethanolamine, diethanolamine, triethanolamine, morpholine, lime, calcium carbonate, magnesia, magnesium carbonate, alkali metal hydroxides orany other similar neutralizing agent. Dilute neutralizing agents, e. g. 3% NaOH in water, are preferred. The sodium octadecyl sulfate can be isolated readily in the form of a dry, white, rather flaky watersoluble solid, by evaporation of water from the neutralized sulfated product. Since the procedure for condensation of the C9 aldehyde, hy-
drogenation of the resulting aldol condensation product and sulfation of the resultant alcohol may be varied rather widely without altering the properties of the octadecanol sulfate thus obtained, it is to be understood that I do not limit myself except as set forth in the following claims.
I claim:
1. A 2-(1,3,3-trimethylbutyl) 5,7,7-trimethyloctanol-l sulfate.
2. Sodium 2 (1,3,3 trimethylbutyl) 5,7,7- trimethyloctanol-l sulfate.
ALBERT A. PAVLIC.
Ser. NO. 369,507, Roelen (A. P. 0.), published July 13, 1943.
Claims (1)
1. A 2-(1,3,3-TRIMETHYLBUTYL) - 5,7,7-TRIMETHYLOCTANOL-1 SULFATE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US160587A US2654772A (en) | 1950-05-06 | 1950-05-06 | 2-(1, 3, 3-trimethylbutyl)-5, 7, 7-trimethyl octanol-1-sulfate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US160587A US2654772A (en) | 1950-05-06 | 1950-05-06 | 2-(1, 3, 3-trimethylbutyl)-5, 7, 7-trimethyl octanol-1-sulfate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2654772A true US2654772A (en) | 1953-10-06 |
Family
ID=22577500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US160587A Expired - Lifetime US2654772A (en) | 1950-05-06 | 1950-05-06 | 2-(1, 3, 3-trimethylbutyl)-5, 7, 7-trimethyl octanol-1-sulfate |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2654772A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2892861A (en) * | 1956-07-23 | 1959-06-30 | Monsanto Chemicals | Organic thiosulfates |
| US3308173A (en) * | 1961-08-30 | 1967-03-07 | Standard Oil Co | Preparation of primary alcohols from glycols by telomerizing alpha-olefin with glycol borate, hydrolysing to obtain telomer glycol, dehydrating the glycol to obtain alkenol and then hydrogenating |
| WO1985002175A1 (en) * | 1981-04-22 | 1985-05-23 | Monsanto Company | Detergent range aldehyde and alcohol mixtures and derivatives, and process therefor |
| US4598162A (en) * | 1981-06-11 | 1986-07-01 | Monsanto Company | Detergent range aldehyde and alcohol mixtures and derivatives, and process therefor |
| EP0401642A1 (en) * | 1989-06-05 | 1990-12-12 | Henkel Kommanditgesellschaft auf Aktien | Fat alkyl sulfates and alkyl-polyalkyleneglycol ether sulfates, process for their production and their use |
| US5849960A (en) * | 1996-11-26 | 1998-12-15 | Shell Oil Company | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US6150322A (en) * | 1998-08-12 | 2000-11-21 | Shell Oil Company | Highly branched primary alcohol compositions and biodegradable detergents made therefrom |
| US6222077B1 (en) | 1996-11-26 | 2001-04-24 | Shell Oil Company | Dimerized alcohol compositions and biodegradible surfactants made therefrom having cold water detergency |
| EP2014354A1 (en) | 2007-07-13 | 2009-01-14 | Clariant International Ltd. | Aqueous compounds containing alkypolyethylenglycolether sulfates |
| US20130023687A1 (en) * | 2010-03-04 | 2013-01-24 | Hirosaki University | Surfactant for stabilizing water/supercritical carbon dioxide microemulsion |
| DE102013009704A1 (en) | 2013-06-10 | 2014-04-03 | Clariant International Ltd. | Aqueous binder-free pigment preparation used to color e.g. macromolecular materials to print e.g. textiles, comprises white/colored pigment, alkylpolyethyleneglycolethersulfates, ethoxylated product of fatty acid alkanol amides, and water |
| WO2015051866A1 (en) | 2013-10-11 | 2015-04-16 | Clariant International Ltd | Anionic fatty amides used as a dispersant for pigment preparations |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR805706A (en) * | 1935-06-08 | 1936-11-27 | Wacker Chemie Gmbh | Method of manufacturing wetting means |
| US2200216A (en) * | 1936-02-14 | 1940-05-07 | Ig Farbenindustrie Ag | Production of high-molecular unsaturated ketones and conversion products thereof |
| US2229649A (en) * | 1929-04-13 | 1941-01-28 | Gen Aniline & Film Corp | Sulphated methyl heptadecenyl carbinol |
-
1950
- 1950-05-06 US US160587A patent/US2654772A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2229649A (en) * | 1929-04-13 | 1941-01-28 | Gen Aniline & Film Corp | Sulphated methyl heptadecenyl carbinol |
| FR805706A (en) * | 1935-06-08 | 1936-11-27 | Wacker Chemie Gmbh | Method of manufacturing wetting means |
| US2200216A (en) * | 1936-02-14 | 1940-05-07 | Ig Farbenindustrie Ag | Production of high-molecular unsaturated ketones and conversion products thereof |
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2892861A (en) * | 1956-07-23 | 1959-06-30 | Monsanto Chemicals | Organic thiosulfates |
| US3308173A (en) * | 1961-08-30 | 1967-03-07 | Standard Oil Co | Preparation of primary alcohols from glycols by telomerizing alpha-olefin with glycol borate, hydrolysing to obtain telomer glycol, dehydrating the glycol to obtain alkenol and then hydrogenating |
| WO1985002175A1 (en) * | 1981-04-22 | 1985-05-23 | Monsanto Company | Detergent range aldehyde and alcohol mixtures and derivatives, and process therefor |
| US4598162A (en) * | 1981-06-11 | 1986-07-01 | Monsanto Company | Detergent range aldehyde and alcohol mixtures and derivatives, and process therefor |
| EP0401642A1 (en) * | 1989-06-05 | 1990-12-12 | Henkel Kommanditgesellschaft auf Aktien | Fat alkyl sulfates and alkyl-polyalkyleneglycol ether sulfates, process for their production and their use |
| WO1990015049A1 (en) * | 1989-06-05 | 1990-12-13 | Henkel Kommanditgesellschaft Auf Aktien | Fatty alkyl sulphates and fatty alkyl polyalkylene glycolether sulphates, process for preparing them and their use |
| US20080249336A1 (en) * | 1996-11-26 | 2008-10-09 | Singleton David M | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US7888307B2 (en) | 1996-11-26 | 2011-02-15 | Shell Oil Company | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US6222077B1 (en) | 1996-11-26 | 2001-04-24 | Shell Oil Company | Dimerized alcohol compositions and biodegradible surfactants made therefrom having cold water detergency |
| US20070219112A1 (en) * | 1996-11-26 | 2007-09-20 | Singleton David M | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US5849960A (en) * | 1996-11-26 | 1998-12-15 | Shell Oil Company | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US7871973B1 (en) | 1996-11-26 | 2011-01-18 | Shell Oil Company | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US7781390B2 (en) | 1996-11-26 | 2010-08-24 | Shell Oil Company | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US6150322A (en) * | 1998-08-12 | 2000-11-21 | Shell Oil Company | Highly branched primary alcohol compositions and biodegradable detergents made therefrom |
| US20090023817A1 (en) * | 2007-07-13 | 2009-01-22 | Clariant International Ltd. | Aqueous compositions comprising alkyl polyethylene glycol ether sulfates |
| DE102007032670A1 (en) | 2007-07-13 | 2009-01-15 | Clariant International Ltd. | Aqueous compositions containing alkyl polyethylene glycol ether sulfates |
| EP2014354A1 (en) | 2007-07-13 | 2009-01-14 | Clariant International Ltd. | Aqueous compounds containing alkypolyethylenglycolether sulfates |
| US20130023687A1 (en) * | 2010-03-04 | 2013-01-24 | Hirosaki University | Surfactant for stabilizing water/supercritical carbon dioxide microemulsion |
| US9101894B2 (en) | 2010-03-04 | 2015-08-11 | Nissan Chemical Industries, Ltd. | Surfactant for stabilizing water/supercritical carbon dioxide microemulsion |
| DE102013009704A1 (en) | 2013-06-10 | 2014-04-03 | Clariant International Ltd. | Aqueous binder-free pigment preparation used to color e.g. macromolecular materials to print e.g. textiles, comprises white/colored pigment, alkylpolyethyleneglycolethersulfates, ethoxylated product of fatty acid alkanol amides, and water |
| WO2015051866A1 (en) | 2013-10-11 | 2015-04-16 | Clariant International Ltd | Anionic fatty amides used as a dispersant for pigment preparations |
| DE102013016889A1 (en) | 2013-10-11 | 2015-04-16 | Clariant International Ltd. | Anionic fatty acid amides as dispersants for pigment preparations |
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