US2073054A - Process of producing pure soaps from oxidized nonaromatic hydrocarbons - Google Patents
Process of producing pure soaps from oxidized nonaromatic hydrocarbons Download PDFInfo
- Publication number
- US2073054A US2073054A US748717A US74871734A US2073054A US 2073054 A US2073054 A US 2073054A US 748717 A US748717 A US 748717A US 74871734 A US74871734 A US 74871734A US 2073054 A US2073054 A US 2073054A
- Authority
- US
- United States
- Prior art keywords
- oxidized
- parts
- water
- solution
- soaps
- 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
- 239000000344 soap Substances 0.000 title description 13
- 229930195733 hydrocarbon Natural products 0.000 title description 6
- 150000002430 hydrocarbons Chemical class 0.000 title description 6
- 238000000034 method Methods 0.000 title description 5
- 239000007864 aqueous solution Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- 239000003799 water insoluble solvent Substances 0.000 description 12
- 230000003647 oxidation Effects 0.000 description 11
- 238000007254 oxidation reaction Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- 239000008149 soap solution Substances 0.000 description 9
- 238000005406 washing Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000470 constituent Substances 0.000 description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229960004132 diethyl ether Drugs 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001704 evaporation 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
- 238000005187 foaming Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- ISCCCEPTSPEASH-UHFFFAOYSA-L hexadecanoate;manganese(2+) Chemical compound [Mn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O ISCCCEPTSPEASH-UHFFFAOYSA-L 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019809 paraffin wax Nutrition 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940045870 sodium palmitate Drugs 0.000 description 1
- GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D13/00—Making of soap or soap solutions in general; Apparatus therefor
- C11D13/02—Boiling soap; Refining
Definitions
- the present invention relates to the production of wetting, washing and dispersing agents.
- the waterinsoluble solvent to be used for dissolving the oxidation products may be the same as or may be different from that to be used for extracting the non-saponifiable matter from the soap solution separated.
- initial materials may be mentioned for example oxidation products of paraflin waxes, mineral oils or higher boiling fractions thereof as for example petroleum or middle oils, and also the products obtained by the oxidation of destructive hydrogenation products of coals and tars.
- solvents or mixtures of several solvents may be employed.
- water-insoluble solvents or solvent mixtures may be mentioned benzine, benzene, cyclohexane, cyclohexanol, tetrahydronaphthalene, carbon tetrachloride and mixtures of benzine and ethyl alcohol.
- the solution of the oxidation products in the water-insoluble'solvents or solvent mixtures may take place at ordinary or elevated temperature. Usually it is effected at temperatures not below 20 C. The upper limit of the temperature used is the boiling point of the solvents employed and it is preferable to work near the latter temperature.
- the solutions thus obtained are then treated with aqueous solutions of alkali metal hydroxides, alkali metal carbonates, ammonia or. amines, as for example 'methylamine, ethylamine, dimethylamine, mono-, dior triethanolfamine.
- the amount of the said aqueous solutions depends on the concentration of the said basic substances in the aqueous solutions and on the saponification value of theoxidation products employed.
- the said basic substances are preferably used in an excess of from about 5 to 10 per cent of the theoretically required amount calculated on the saponification value.
- the working temperature depends on the composition of the oxidation'products and may be readily ascertained by a simple experiment. It may be desirable to work under pressure in order to avoid losses of solvents, especially if low boiling solvents are employed. After mixing thoroughly, the whole is allowed to settle; the soap solution is then withdr vvn.
- the aqueous soap solution is treated with a watersired temperature under ordinary or elevated ,pressure, filtered if necessary and if desired evaporated to dryness in a suitable manner under ordinary or decreased pressure. The drying may be effected for example in a roller dryer or a Krause apparatus.
- the products obtained according to this invention are pale soaps which have practically no undesirable odor and are therefore capable of employment for further' Working up into shaped soaps or other washing or like agents.
- Hard paraflin wax is oxidized by blowing with air at from to C. while employing 0.05 per cent of sodium palmitate and 0.05 per cent of manganese palmitate as catalysts for 4 hours in the usual manner.
- 1200 parts of the resulting oxidation product having a saponification value of 149, are dissolved in a mixture of 2400 parts of benzine and 600 parts of ethyl alcohol and intimately stirred for half an hour at a temperature of from 56 to 58 C. with a solution of 184 parts of sodium carbonate in 920 parts of water.
- the mixture is then allowed to settle and the soap insoluble solvent (or solvent mixture) at any desolution. is withdrawn.
- the latter is extracted with 1200 parts of benzine and evaporated to dryness in a roller dryer.
- a good yield of a colorless and odorless soap powder having a high wetting, foaming and washing power is'thus obtained.
- Example 2 A so-called middle oil is oxidized with air at from about to C. while adding 0.2 per cent of manganese naphthenate as a catalyst for 3 hours, an oxidation product thus being obtained having a saponiflcation value of 90. 630 parts of this oxidation product are dissolved in 1200 parts of benzene and intimately stirred for half an hour at a temperature of from 40 to 45 Cl with a solution of 44 parts of sodium hydroxide in 560 parts of water. The mixture is then allowed to settle, the soap solution is drawn off and extracted with 600 parts of benzene. The soap solution thus obtained may be directly employed for washing. It may also be evaporated to dryness by spraying in a Krause apparatus, a yellowish odorless soap powder having a high foaming and washing power thus being obtained.
- Example 3 500 parts of the oxidation product obtained as set forth in the first sentence of Example 1 are dissolved in about 710 parts of diethylether. The solution is stirred together with a solution of 200 parts of triethanolamine in 1000 parts of water with the addition of 240 parts of ethyl alcohol at 33 C. for 45 minutes in a closed vessel. After cooling, the soap layer is separated and extracted once or twice with 710 parts of diethylether. The soap solution thus obtained is a highly active washing agent.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2073054X | 1933-10-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2073054A true US2073054A (en) | 1937-03-09 |
Family
ID=7983646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US748717A Expired - Lifetime US2073054A (en) | 1933-10-19 | 1934-10-17 | Process of producing pure soaps from oxidized nonaromatic hydrocarbons |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2073054A (fr) |
| FR (1) | FR779843A (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2453588A (en) * | 1945-05-02 | 1948-11-09 | Union Oil Co | Purification of organic acids |
| US2516127A (en) * | 1948-04-20 | 1950-07-25 | Kellogg M W Co | Separation of organic compounds |
| US2516126A (en) * | 1948-03-02 | 1950-07-25 | Kellogg M W Co | Separation of organic compounds |
| US2552564A (en) * | 1947-02-27 | 1951-05-15 | Kellogg M W Co | Separation of organic compounds |
-
1934
- 1934-10-17 FR FR779843D patent/FR779843A/fr not_active Expired
- 1934-10-17 US US748717A patent/US2073054A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2453588A (en) * | 1945-05-02 | 1948-11-09 | Union Oil Co | Purification of organic acids |
| US2552564A (en) * | 1947-02-27 | 1951-05-15 | Kellogg M W Co | Separation of organic compounds |
| US2516126A (en) * | 1948-03-02 | 1950-07-25 | Kellogg M W Co | Separation of organic compounds |
| US2516127A (en) * | 1948-04-20 | 1950-07-25 | Kellogg M W Co | Separation of organic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR779843A (fr) | 1935-04-13 |
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