US3696143A - Detergent active materials - Google Patents

Detergent active materials Download PDF

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Publication number
US3696143A
US3696143A US58023A US3696143DA US3696143A US 3696143 A US3696143 A US 3696143A US 58023 A US58023 A US 58023A US 3696143D A US3696143D A US 3696143DA US 3696143 A US3696143 A US 3696143A
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Prior art keywords
isopropanol
solution
water
alkane sulphonate
percent
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Expired - Lifetime
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US58023A
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English (en)
Inventor
Virender Nath Malhotra
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Lever Brothers Co
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Lever Brothers Co
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    • 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
    • C07C303/42—Separation; Purification; Stabilisation; Use of additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D9/00—Crystallisation
    • B01D9/0018—Evaporation of components of the mixture to be separated
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D9/00—Crystallisation
    • B01D9/0036—Crystallisation on to a bed of product crystals; Seeding
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D9/00—Crystallisation
    • B01D9/0059—General arrangements of crystallisation plant, e.g. flow sheets

Definitions

  • the inorganic salt content of alkane sulphonates, alcohol sulphates and olefin sulphonates can be reduced by treating the detergent active with a mixture of water and. isopropanol and/or isobutanol with the conversion of bisulphite ions into sulphite ions.
  • the treatment is performed under reflux at a temperature between boiling and 20C below boiling. A proportion of the inorganic material precipitates and is separated from the liquor which contains the active.
  • Theinvention is particularly useful for reducing the inorganic salt content of such a product.
  • the invention provides a method of reducing the inorganic material content of a detergent active material comprising the steps of;
  • the active powder or paste into a monophase solution with a solvent mixture of water and isopropyl alcohol, and/ortertiary butyl alcohol.
  • the bisulphite conversion can be performed before the monophase solution is formed. It has been found advisable to seed the solution to speed up the process of precipitation and thus increase the amount of inorganic material separated.
  • monophase refers to the liquid phase which must exist as a single phase although it may contain some undissolved solid material when first formed.
  • the ratio of water to alcohol in the solvent mixture will be determined by the user of the invention having regard to the amount of inorganic material in the detergent active material.
  • a good separation of inorganic material is achieved in the region of the azeotropphite with an alpha-olefins.
  • Alpha-olefins normally contain antioxidants to minimize their deterioration in the presence of atmospheric oxygen. It has been found that pretreatment of alpha-olefins as described in GB Pat. No. 1,159,728 removes a substantial proportion of such antioxidants.
  • sodium alkane sulphonate as an active in some special formulations, it is desirable to have the concentration of inorganic material below 2 percent. This is achieved by using a solvent mix containing more than percent by weight of isopropyl alcohol or more than 78 percent by weight of tertiary butanol at boiling reflux. The upper concentration limit will be determined by the amount of alcohol the user is prepared to use per unit of detergent active.
  • Sodium alkane sulphonate suitable for use as a detergent active usually contains from eight to 22 carbon atoms in a straight chain with the sulphonate group at one end of the chain.
  • Such compounds can be prepared by, for instance, free-radical reaction of sodium bisulto the alkane sulphonate being heated in solution by aqueous alcohol. This obviates a tendency for a liquid phase containing much of the inorganic salts to form; to separate the inorganic salts once this liquid phase forms is especially difficult.
  • the invention is particularly applicable to sodium alkane sulphonate prepared by the free-radical reaction of sodium bisulphite with alpha-olefin in aqueous isopropanol.
  • the weight ratio of isopropanol to water is usually less than 65:35 during the addition reaction, and after completion the concentration of isopropanol can be brought to the desired level for salt separation.
  • FIGS. 1 and 2 show the reduction in inorganic content of sodium alkane sulphonate using respectively isopropanol and tertiary butanol in the concentrations with water shown.
  • axis A shows the concentration of inorganic material in the detergent active and axis B shows the ratio by weight of the isopropanol/water and tertiary butanol/water mixtures.
  • FIG. 2 shows the results of experiments using tertiary butanol and starting with a crude c sodium alkane sulphonate containing 12.25 percent inorganic material i.e. sodium bisulphite, sulphite and sulphate.
  • the process of the invention allows the inorganic salt content to be reduced to the region of 2 percent.
  • the use of an isopropanol/water mixture containing at least 70 percent by weight of the alcohol or a tertiary butanol/water mixture containing at least 78 percent by weight of the alcohol provides an alkane sulphonate with an inorganic material concentration of not more than 2 percent.
  • the invention also extends to processes for a reduction of inorganic material content in detergent active materials.
  • a preferred process according to the invention consists of the following stages;
  • crystalline inorganic salt is separated at a temperature from 20C below reflux to reflux;
  • the aqueous isopropanol is fed to a distillation column where it is separated into water and isopropanol or azeotrope; and,
  • stage (a) e. the isopropanol or azeotrope is used in stage (a).
  • the separation in stage (d) need not be complete; azeotrope can be formed.
  • the water can contain some isopropanol; the water will in any case contain a major proportion of any oily matter originally mixed with the sodium alkane sulphonate, for instance, paraffin and residual olefine. This is a further advantage for this process.
  • the inorganic salts separated at stage (b) will be in a convenient form to extract sodium sulphite for re-use in the bisulphite reaction with olefin for making the alkane sulphonate.
  • stage (b) crystallization is initiated by the addition of seed quantities of crystalline sodium sulphite and sulphate.
  • aqueous isopropanol in which the reaction between a-olefin and sodium bisulphite has occurred, is flashed off from the sodium alkane sulphonate and inorganic salts.
  • Neat isopropanol or, preferably, an azeotrope of isopropanol and water is added to the sodium alkane sulphonate and inorganic salts and the solution so formed heated at a temperature from 20C below reflux to reflux so that the inorganic salts start to crystallize. Crystalline inorganic salts are then separated and isopropanol and water flashed off to give sodium alkane sulphonate with reduced inorganic salt content.
  • the aqueous isopropanol, in which the reaction has occurred, and the water and isopropanol after separation of crystalline inorganic salts are fed to a distillation column to give an azeotrope of isopropanol and water and water which contains the bulk of any oily matter originally mixed with the sodium alkane sulphonate.
  • the flash evaporator also enables the amount of azeotrope and hence the size of the crystallizers to be minimized.
  • the amount of azeotrope added at the crystallization stage can be related to the solubility of the active at the temperature concerned.
  • distillation column should be operated under slight vacuum. Thereby the operation of the flash evaporators is aided.
  • an isopropanol and water solution of sodium alkane sulphonate together with organic and inorganic impurities is produced, A.
  • sufficient sodium hydroxide, a to convert any residual sodium bisulphite to sodium sulphite.
  • the mixture is then fed to a crystallizer, B, where it is heated to or maintained at reflux temperature, ca 82C, and sufficient isopropanol, b, is added to raise the weight ratio of isopropanol to water in the mixture to :30. Crystallization of inorganic salts occurs and the crystalline salts, c, are separated in centrifuge, C.
  • the isopropanol and water solution of sodium alkane sulphonate is fed to a flash-evaporator D.
  • Sodium alkane sulphonate, d, with a reduced inorganic salt content is obtained.
  • the flashed off isopropanol and water, 2 is fed to an azeotropic or extractive distillation column, E, where the isopropanol, f, and water, g, are at least to a major extent separated.
  • lsopropanol and water vapors d, from the flash chamber, C are fed to a cyclone separator, D
  • Sodium alkane sulphonate, c, from the separator is fed to the Crystallizers, I.
  • the vapors d, from the separator are fed to a distillation column, E, where they are fractionated into water, e, which contains the bulk of the organic impurities in the sodium alkane sulphonate, and an azeotrope, f, of isopropanol and water.
  • the distillation column, E is backed by a condenser, F, and a steam ejector system, G.
  • a proportion of the azeotrope, g, from the condenser, F, is returned to the distillation column.
  • the remainder is fed to a storage vessel, H.
  • Sufficient of the azeotrope or azeotrope enhanced with isopropanol is fed, i, to the crystallizers, I, to dissolve the sodium alkane sulphonate at a temperature from 20C below reflux to reflux.
  • a metafilter J, crystalline inorganic salts, j, are separated.
  • a second distillation column is provided immediately before dryer B Isopropanol and water vapors are fed back to the distillation column E and the concentrated alkane sulphonate solution supplied to dryer B
  • This invention relates also to an improvement in the process of reacting a bisulphite material for example the sodium salt, with an alpha-olefinic material to give an alkane sulphonate detergent active.
  • the reaction is normally performed in a reaction medium comprising a mixture of isopropanol and water. The inventor has found that the amount of isopropanol required in the reaction mixture per ton of active per hour can be minimized to give reduced requirements for raw materials and equipment.
  • the invention is directed to a process wherein a bisulphite material is reacted with a C to C alpha olefin in a reaction medium comprising isopropanol and water characterized in that the weight of alpha olefin taken as starting material is sufficient to give an amount of alkane sulphonate after conversion; the ratio between the amount of alkane sulphonate and total amount of isopropanol, water and alkane sulphonate being in the range of 0.2 to 0.3.
  • the ratio is preferably about 0.25 and for a C -C olefin the ratio is preferably about 0.3.
  • FIGS. 5 and 6 show respectively the tons of isopropanol required per ton of active produced per hour (axis D) plotted against the ratio of the weight of active produced to the total weight of active, isopropanol and water (axis C). It is seen that minima occur in the graphs at 0.25 in FIGS. 5 which relates to C -C alpha olefins and at 0.30 in FIG. 6 which relates to C -C alpha olefins.
  • the final product was 1.66 tons (3,733 lbs) of sodium alkane sulphonate.
  • the ratio as defined by the invention was 0.25.
  • a process for reducing the inorganic salt content of an alkane sulphonate containing about eight to about 22 carbon atoms prepared by reacting an alkali metal bisulphite with an olefinic compound, comprising the steps of:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
US58023A 1969-07-25 1970-07-24 Detergent active materials Expired - Lifetime US3696143A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3745369 1969-07-25

Publications (1)

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US3696143A true US3696143A (en) 1972-10-03

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US (1) US3696143A (xx)
JP (1) JPS5016776B1 (xx)
AT (1) AT310331B (xx)
BE (1) BE753935A (xx)
CH (1) CH548375A (xx)
DE (1) DE2036710A1 (xx)
ES (1) ES382177A1 (xx)
FR (1) FR2055611A5 (xx)
GB (1) GB1313658A (xx)
LU (1) LU61401A1 (xx)
NL (1) NL7010891A (xx)
ZA (1) ZA705073B (xx)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006111A (en) * 1972-07-12 1977-02-01 Lever Brothers Company Production of alkane: olefin sulfonate mixtures by sequential sulfonation and sulfitation
US4287080A (en) * 1979-09-17 1981-09-01 The Procter & Gamble Company Detergent compositions which contain certain tertiary alcohols

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU621675A1 (ru) * 1976-04-05 1978-08-30 Предприятие П/Я В-2287 Способ получени щелочных солей алкилсульфокислот

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2316719A (en) * 1943-04-13 Purification of organic substances
US2810745A (en) * 1955-07-05 1957-10-22 Sun Oil Co Purifying mahogany sulfonic acids
US2952639A (en) * 1954-06-30 1960-09-13 Stepan Chemical Co Purification of detergent compositions
US3031498A (en) * 1958-02-04 1962-04-24 Procter & Gamble Preparation of detergent compositions
US3186948A (en) * 1961-02-27 1965-06-01 California Research Corp Detergent toilet bars
NL6600282A (xx) * 1966-01-10 1967-07-11
GB1093103A (en) * 1964-04-08 1967-11-29 Hoechst Ag Process for preparing alkene-sulphonates
US3496226A (en) * 1967-12-01 1970-02-17 Hoechst Ag Process for the purification of olefin-sulfonates
US3541140A (en) * 1968-12-17 1970-11-17 Gulf Research Development Co Process for preparing detergent sulfonates

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2316719A (en) * 1943-04-13 Purification of organic substances
US2952639A (en) * 1954-06-30 1960-09-13 Stepan Chemical Co Purification of detergent compositions
US2810745A (en) * 1955-07-05 1957-10-22 Sun Oil Co Purifying mahogany sulfonic acids
US3031498A (en) * 1958-02-04 1962-04-24 Procter & Gamble Preparation of detergent compositions
US3186948A (en) * 1961-02-27 1965-06-01 California Research Corp Detergent toilet bars
GB1093103A (en) * 1964-04-08 1967-11-29 Hoechst Ag Process for preparing alkene-sulphonates
NL6600282A (xx) * 1966-01-10 1967-07-11
US3496226A (en) * 1967-12-01 1970-02-17 Hoechst Ag Process for the purification of olefin-sulfonates
US3541140A (en) * 1968-12-17 1970-11-17 Gulf Research Development Co Process for preparing detergent sulfonates

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Hackh s Chemical Dictionary, 3rd Ed., Copyright 1944, McGraw Hill Book Co., Inc., p. 151. *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006111A (en) * 1972-07-12 1977-02-01 Lever Brothers Company Production of alkane: olefin sulfonate mixtures by sequential sulfonation and sulfitation
US4287080A (en) * 1979-09-17 1981-09-01 The Procter & Gamble Company Detergent compositions which contain certain tertiary alcohols

Also Published As

Publication number Publication date
NL7010891A (xx) 1971-01-27
FR2055611A5 (xx) 1971-05-07
CH548375A (de) 1974-04-30
JPS5016776B1 (xx) 1975-06-16
DE2036710A1 (de) 1971-01-28
BE753935A (fr) 1971-01-25
AT310331B (de) 1973-09-25
GB1313658A (en) 1973-04-18
ES382177A1 (es) 1973-04-16
LU61401A1 (xx) 1971-07-13
ZA705073B (en) 1972-02-23

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