US2530042A - Separating higher molecular alcohols from the soaps obtained in the preparation of the same - Google Patents

Separating higher molecular alcohols from the soaps obtained in the preparation of the same Download PDF

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Publication number
US2530042A
US2530042A US779384A US77938447A US2530042A US 2530042 A US2530042 A US 2530042A US 779384 A US779384 A US 779384A US 77938447 A US77938447 A US 77938447A US 2530042 A US2530042 A US 2530042A
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Prior art keywords
soap
solvent
high molecular
water
solution
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Expired - Lifetime
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US779384A
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English (en)
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Blinoff Vsevolod
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D'innovations Chimiques Dite Sinnova Ou Sadic SA Ste
INNOVATIONS CHIMIQUES SINNOVA
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INNOVATIONS CHIMIQUES SINNOVA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/86—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
    • 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
    • C11D13/04—Continuous methods therefor

Definitions

  • solvents for the fatty alcohols there may be-used such aliphatic or cyclic alcohols as propyl 2 alcohol, butyl alcohol, amyl alcohol, lauryl alcohol, eyclohexanol, aliphatic or cyclic hydrocarbons, gasoline, benzene, toluene, cyclohexane, ketones, etc, or mixtures of such solvents.
  • aliphatic or cyclic alcohols as propyl 2 alcohol, butyl alcohol, amyl alcohol, lauryl alcohol, eyclohexanol, aliphatic or cyclic hydrocarbons, gasoline, benzene, toluene, cyclohexane, ketones, etc, or mixtures of such solvents.
  • the present invention has for its object a method of separating heavy alcohols from their mixture with the soap obtained in preparing the same by causing the heavy alcohols to pass into a water-insoluble solvent in which soap is less soluble than in water.
  • the invention is applicable to all alcohols and alcohol mixtures Whose molecular Weights are higher than C5, and in particular to alcohols obtained by reducing cocoanut oil, palm oil, sperm oil, fish oils and to synthetic alcohols.
  • the material resulting from this washing step is admixed with 600 kg. of benzene and 600 kg. of water. The mixture breaks up into two layers,
  • the mixture breaks up into two layers and. the coefiicient of division of the soap amongst the two layers is 2.6 to the advantage of the aqueous layer.
  • the washing operation is repeated several times until the soap is completely separated from the heavy alcohols. After three Washes there remains no soap in the alcoholic layer; the alcohols are stripped therefrom.
  • the product obtained is admixed with 80 parts by volume of butanol, parts by volume of toluone and to the whole there are added 280 parts by volume of water.
  • the raw product is washed with water in order to eliminate the sodium hydroxide as a 36 B. solution; the remaining oil, that is, about 150 parts by volume, is admixed with 100 parts by volume of water.
  • the soap content of the oily portion is four times less than that of the aqueous portion.
  • the operation is continued like in the preceding examples.
  • the amount of soap present in the oil is then 14 times less than the amount contained in the water.
  • the operation is continued in the same manner as in the preceding examples.
  • a tank B is fed through a pipe l with the mixture of heavy alcohols and soap which are to be separated.
  • the solvent recovered in the continuous operation flows into the tank through a pipe [4.
  • the mixture of solvent, soap and alcohol is flowed through a pipe 2 into a washing column L.
  • the water necessary for separating the soap is fed into the column through a ,pipe 3.
  • Said water flows out through the pipe 1 as an aqueous soap solution that contains solvent and it is led into a distillation column D2 in which the soap solution is to be separated from the solvent and from which the solvent recovered is led into the tank B through the pipe line 9 and the condenser C.
  • the soap solution flows out at 8.
  • the solution of heavy alcohols in the solvent is discharged from the washing column L at 5 and is led into a column D1 in which said heavy alcohols are separated from the solvent.
  • the heavy alcohols are discharged at 6 while the solvent recovered flows out at [0, is condensed in the condenser C and is led back into the tank B through the pipe it.
  • a portion of said solvent is used: on one hand by means of a pipe 4 to remove the last traces of heavy alcohols from the soap in the solution discharged through pipe 7, on the other hand to provide for the retrogradations necessary for the operation of the columns D1 and D2, and this, through the pipes I2 and I3.
  • this system may be equipped with automatic regulators.
  • Another way of carrying the invention into effect consists in separating the alcohols from the soaps and to continuously regenerate the fatty acids present therein so that the apparatus will deliver the alcohols to be separated and the regenerated fatty acids. This can be accomplished in the apparatus shown in Fig. 2.
  • the tank B is supplied through a pipe I with the mixture of heavy alcohols and soap to be separated. Said tank is fed through a pipe I4 with the solvent reclaimed in the continuous operation. Said mixture of solvent, soap and a1- cohol is led through a pipe 2 into a washing column L1.
  • the water necessary for separating the soap is fed into the column through a pipe 3. Said water flows out through a pipe 1 as an aqueous solvent-containing soap solution which is fed into a washing column L2.
  • a mineral or organic acid is fed into said column L2 through a pipe IE to wash the soap solution and set free the fatty acid; it flows out as an aqueous solution of sodium salts.
  • the solvent-containing fatty acid is discharged at I! and led to a distillation column D2 in which the solvent is separated from the fatty acids and then recycled as in the preceding example while the fatty acid recovered is discharged at l 8.
  • a return of the said acids to the bottom of column L2 (pipe I9) is provided in order to strip the salt solution discharged at I6 from any solvent that might remain dissolved therein.
  • the solvent containing the heavy alcohol is discharged at 5 and led to a distillation column D1.
  • the heavy alcohol flows out at 6 and the solvent at 10. It is condensed in a condenser C from which it is discharged through the pipes I4 and H to perform the same function as in diagram No. 1, that is, washing in the bottom of column L, retrogradation in the distillation apparatus, the solvent being returned to tank B.
  • a continuous method for the separation of high molecular fatty alcohols from their mixtures with soap obtained in the preparation of the same comprising admixing a high molecular alcohol and soap mixtures with a solvent for the high molecular alcohol in which the soap is less soluble than in water and introducing the resulting mixture into the middle portion of a washingtower, introducing wash-water into the top portion of said tower, discharging aqueous soap solution containing a small quantity of the solvent from the bottom of the tower, feeding the same into the top part of a first distillation column, condensing solvent vapors that escape from the top of the said first distillation column, tapping solution of high molecular alcohol from the top of the aforesaid washing tower, leading said last named solution into a second distillation column in which the solvent is separated from the high molecular alcohol, condensing solvent vapors that escape from the top of the said second distillation column, and re-using the solvent condensate from the first and the second distillation columns to treat further amounts of the
  • a continuous method for the separation of high molecular fatty alcohols from their mixtures with soap obtained in the preparation of the same comprising admixing a high molecular alcohol and soap mixtures with a solvent for the high molecular alcohol in which the soap is less soluble thanin water and introducin the resulting mixture into the middle portion of a washing tower, introducing wash-water into the top portion of said tower, introducing a smaller amount of the same solvent into the lower portion of said tower, discharging aqueous soap solution containing a small quantity of the solvent from the bottom of the tower, feeding the same into the top part of a first distillation column, condensing solvent vapors that escape from the top of the said first distillation column, tapping solution of high molecular alcohol from the top of the aforesaid washing tower, leading said last named solution into a second distillation column in which the solvent is separated from the high molecular alcohol, condensing solvent vapors that escape from the top of the said second distillation column, and re-using the solvent con
  • a continuous method for the separation of high molecular fatty alcohols from their mixtures with soap obtained in the preparation of the same comprising admixing a high molecular fatty alcohol and soap mixture with a solvent for the high molecular fatty alcohol in which the soap is less soluble than in water and introducing the resulting mixture into the middle portion of a main Washing tower, introducing wash-water into the top portion of said main washing tower, tapping the high molecular fatty alcohol solution from the top of said main washing tower, feeding said solution into a first distillation column in which the solvent is separated from the high molecular fatty alcohol, condensing solvent vapors that escape from the top of said column, discharging aqueous soap solution containing a small quantity of the solvent from the bottom of the main washing-tower, introducing said last named solution into an additional washing-tower, feeding an acid into the top thereof, tapping the thus formed aqueous alkali salt solution from the bottom of said additional washing-tower, tapping the solvent solution of fatty acid from the top of said
  • a continuous method for the separation of high molecular fatty alcohols from their mixtures with soap obtained in the preparation of the same comprising admixing a high molecular fatty alcohol and soap mixture with a solvent for the high molecular fatty alcohol in which the soap is less soluble than in water and introducing the resulting mixture into the middle portion of a main washing-tower, introducing wash-water into the top portion of said main washing tower, tapping the high molecular fatty alcohol solution from the top of said main washing tower, feeding said solution into a first distillation column in which the solvent is separated from the high molecular fatty alcohol, condensing solvent vapors that escape from the top of said column, introducing a smaller flow of the same solvent into the lower portion of said washing-tower, discharging aqueous soap solution containing a small quantity of the solvent from the bottom of the main washing-tower, introducing said last named solution into an additional washing-tower, introducing an acid into the top of said washing tower tapping the thus formed aqueous alkali salt

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Detergent Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US779384A 1947-03-11 1947-10-11 Separating higher molecular alcohols from the soaps obtained in the preparation of the same Expired - Lifetime US2530042A (en)

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FR944199T 1947-03-11

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BE (1) BE480277A (enrdf_load_html_response)
DE (1) DE970983C (enrdf_load_html_response)
FR (1) FR944199A (enrdf_load_html_response)
NL (1) NL83671C (enrdf_load_html_response)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2824898A (en) * 1956-02-24 1958-02-25 Exxon Research Engineering Co Removal of soap from oxo bottoms by solid adsorbents
US4009213A (en) * 1971-11-11 1977-02-22 Henkel & Cie G.M.B.H. Continuous process for the separation of mixtures of fatty substances of different melting points
EP1390331A4 (en) * 2001-04-27 2006-01-11 Wyeth Corp PRIMARY ALIPHATIC ALCOHOLS WITH HIGH MOLECULAR WEIGHT OBTAINED FROM NATURAL PRODUCTS, AND USES THEREOF

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1814654A (en) * 1927-08-01 1931-07-14 Standard Oil Co Production of cetyl alcohol
US2019022A (en) * 1934-06-09 1935-10-29 Du Pont Preparation of high molecular weight alcohols
US2070318A (en) * 1934-09-28 1937-02-09 Ici Ltd Manufacture of alcohols
US2080111A (en) * 1934-05-28 1937-05-11 Monsanto Chemicals Purification of alcohols obtained from olefines
US2148846A (en) * 1936-04-11 1939-02-28 Firm Of Deutsche Gold Und Silb Process for the separation of alcohol from the first runnings
US2193321A (en) * 1937-06-04 1940-03-12 Ig Farbenindustrie Ag Process for the recovery of high molecular weight carboxylic acids or their salts
US2287128A (en) * 1938-07-23 1942-06-23 Jasco Inc Process for purifying fatty acids
US2421040A (en) * 1942-06-18 1947-05-27 Alox Corp Process of obtaining polar-type corrosion-inhibiting agents soluble in petroleum lubricating oils

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR824756A (fr) * 1936-09-17 1938-02-16 Henkel & Compagnieg M B H Procédé et dispositif pour éliminer les composants insaponifiables des savons ou des substances analogues aux savons
DE716195C (de) * 1937-10-05 1942-01-14 Noblee & Thoerl G M B H Verfahren und Vorrichtung zur Gewinnung von organischen Saeuren aus den Oxydations- erzeugnissen aliphatischer oder cycloaliphatischer Kohlenwasserstoffe
DE736096C (de) * 1938-08-09 1943-06-08 Ig Farbenindustrie Ag Verfahren zur Entfernung nicht verseifter und unverseifbarer Anteile aus Verseifungsgemischen hoehermolekularer Fettsaeuren

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1814654A (en) * 1927-08-01 1931-07-14 Standard Oil Co Production of cetyl alcohol
US2080111A (en) * 1934-05-28 1937-05-11 Monsanto Chemicals Purification of alcohols obtained from olefines
US2019022A (en) * 1934-06-09 1935-10-29 Du Pont Preparation of high molecular weight alcohols
US2070318A (en) * 1934-09-28 1937-02-09 Ici Ltd Manufacture of alcohols
US2148846A (en) * 1936-04-11 1939-02-28 Firm Of Deutsche Gold Und Silb Process for the separation of alcohol from the first runnings
US2193321A (en) * 1937-06-04 1940-03-12 Ig Farbenindustrie Ag Process for the recovery of high molecular weight carboxylic acids or their salts
US2287128A (en) * 1938-07-23 1942-06-23 Jasco Inc Process for purifying fatty acids
US2421040A (en) * 1942-06-18 1947-05-27 Alox Corp Process of obtaining polar-type corrosion-inhibiting agents soluble in petroleum lubricating oils

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2824898A (en) * 1956-02-24 1958-02-25 Exxon Research Engineering Co Removal of soap from oxo bottoms by solid adsorbents
US4009213A (en) * 1971-11-11 1977-02-22 Henkel & Cie G.M.B.H. Continuous process for the separation of mixtures of fatty substances of different melting points
EP1390331A4 (en) * 2001-04-27 2006-01-11 Wyeth Corp PRIMARY ALIPHATIC ALCOHOLS WITH HIGH MOLECULAR WEIGHT OBTAINED FROM NATURAL PRODUCTS, AND USES THEREOF

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DE970983C (de) 1958-11-20
NL83671C (enrdf_load_html_response)
FR944199A (fr) 1949-03-29
BE480277A (enrdf_load_html_response)

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