EP0564719A1 - Procédé de préparation d'une composition détergente à haute activité contenant de l'acide succinique - Google Patents

Procédé de préparation d'une composition détergente à haute activité contenant de l'acide succinique Download PDF

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Publication number
EP0564719A1
EP0564719A1 EP92201034A EP92201034A EP0564719A1 EP 0564719 A1 EP0564719 A1 EP 0564719A1 EP 92201034 A EP92201034 A EP 92201034A EP 92201034 A EP92201034 A EP 92201034A EP 0564719 A1 EP0564719 A1 EP 0564719A1
Authority
EP
European Patent Office
Prior art keywords
succinic acid
water
buffer tank
succinic anhydride
succinic
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.)
Granted
Application number
EP92201034A
Other languages
German (de)
English (en)
Other versions
EP0564719B1 (fr
Inventor
Noel Vanwelssenaers
Luc Lievens
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to DE1992614932 priority Critical patent/DE69214932T2/de
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to ES92201034T priority patent/ES2093766T3/es
Priority to EP19920201034 priority patent/EP0564719B1/fr
Priority to JP5518371A priority patent/JPH07505668A/ja
Priority to US08/318,612 priority patent/US5719116A/en
Priority to CA002117746A priority patent/CA2117746C/fr
Priority to PCT/US1993/002943 priority patent/WO1993021290A1/fr
Priority to MX9302049A priority patent/MX9302049A/es
Priority to IE930279A priority patent/IE930279A1/en
Priority to CN 93104023 priority patent/CN1078998A/zh
Publication of EP0564719A1 publication Critical patent/EP0564719A1/fr
Application granted granted Critical
Publication of EP0564719B1 publication Critical patent/EP0564719B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/08—Polycarboxylic acids containing no nitrogen or sulfur
    • 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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/04—Special methods for preparing compositions containing mixtures of detergents by chemical means, e.g. by sulfonating in the presence of other compounding ingredients followed by neutralising

Definitions

  • Succinic acid and its salts are known ingredients of detergent compositions. They are used for their surface active and hydrotropic properties as well as calcium and magnesium binding capacity.
  • This hydrolysis typically requires a considerable excess of water and the presence of solvents (eg. lower alcohols), in an alkaline environment in order to make the hydrolysis reaction move rapidly to completion.
  • solvents eg. lower alcohols
  • GB-A-2 049 723, published December 31, 1980 discloses a composition containing partly neutralised succinic acid with one of its salts such that the pH is in the range from 5.5 to 8.0. It describes liquid compositions containing 3%-50% by weight of the partly neutralised succinic acid.
  • EP 0 028 850 published May 5, 1981, discloses a liquid detergent composition containing succinates and a low level of alkyl benzene sulphonate, for improved storage stability.
  • the application mentions the neutralisation of the acid or anhydride in situ, but there is no mention of high active compositions.
  • GB 1 285 582 published August 16, 1972, discloses a composition substantially containing 25-90% succinic acid, which may be derived from the anhydride, and 10-75% nonionic surfactant. There is no disclosure of a suitable process for making such compositions.
  • the present invention provides a new process for hydrolysis of the succinic anhydride to yield a solution of at least 85% by weight of partly neutralised succinic acid.
  • the process can be carried out in situ, continuously or batch-wise, and offers a flexible process for making a concentrated liquid detergent.
  • a process for making a concentrated liquid detergent composition which comprises
  • the present invention provides a process for the hydrolysis of succinic anhydride to succinic acid in the presence of a small excess of water.
  • the process takes place in the presence of an alkali which catalyses the reaction and partly neutralises the succinic acid.
  • the succinic anhydride, water and alkali are intimately mixed, either by passing through static mixers, or, preferably, in a high shear mixer.
  • the mixture is then stored in a buffer tank (which may be in-line in a continuous process) until the exothermic hydrolysis reaction is substantially completed.
  • the resulting high active partly neutralised succinic acid may then be stored or transferred directly into a batch tank or continuous process for further processing to a concentrated liquid detergent.
  • Any succinic anhydride of the general formula: is suitable for use in the present invention.
  • R will be made by the detergent formulator.
  • Any suitable alkali may be used including sodium hydroxide, potassium hydroxide, monoethanolamine and ammonia. Preferred are sodium hydroxide and potassium hydroxide.
  • the alkali may be added to the succinic acid in the form of a solution (typically 50% aqueous solution of either sodium or potassium hydroxide). Extra water may also be added in order to ensure complete hydrolysis by the following reaction: However total water which is present (both added and with the aqueous alkali) should be limited in order to avoid diluting the final composition, and to avoid an excessively long reaction time. It has been found that the ratio of succinic anhydride to water should be not less than 4:1 by weight.
  • the reactants are brought together and mixed, preferably in a high shear mixer.
  • Suitable mixers include Pentax (trade name), supplied by Bran and Luebbe, Germany; Dispax (trade name), supplied by Janke and Kunkel, and mixers supplied by Karg and Fryma.
  • This mixture is then pumped into buffer tank where the hydrolysis reaction will proceed.
  • the buffer tank already contains an amount of succinic acid which itself promotes rapid hydrolysis of the mixture.
  • the buffer tank is in-line in a continuous process and gives a residence time sufficient for hydrolysis to be substantially completed.
  • the buffer tank contains at all times a mixture of succinic acid, water, alkali and partly neutralised succinic anhydride.
  • the hydrolysis reaction is exothermic, and the temperature rises, preferably to about 90°C.
  • the buffer tank should be gently stirred or agitated in order to keep the reactants mixed. In the case of a continuous process the buffer tank should be designed to give a residence time of from 2 to 30 minutes, preferably from 5 to 20 minutes.
  • the high active succinic acid made according to the above ratios and process has a pH of less than 5.5, preferably about pH4.5 when it is diluted to a 0.5% aqueous solution. Furthermore, after hydrolysis the ratio of partly neutralised succinic acid to water will not be less than about 6:1 by weight.
  • the process is shutdown by firstly closing the supply of water and alkali to the mixer.
  • the supply of succinic anhydride is allowed to continue until all water and alkali have been flushed through the mixer then this supply is also shut-down.
  • This procedure ensures that no hydrolysis continues in the mixer whilst not in use.
  • Preferably not all of the succinic acid is flushed through the buffer tank. This means that when the supplies of succinic anhydride, water and alkali are switched on for start-up, there is still some acid in the buffer tank to "seed" the hydrolysis reaction.
  • the buffer tank should be maintained at an elevated temperature (typically 60-80°C) in order to prevent solidification of the succinic acid/anhydride mix.
  • the highly active, partly neutralised succinic acid made by the present invention may subsequently be added to other detergent ingredients including surfactants, builders, chelants, enzymes and softening clays, in order to make a finished liquid detergent composition.
  • other detergent ingredients including surfactants, builders, chelants, enzymes and softening clays.
  • the high active succinic acid is mixed with compatible detergent ingredients which allow its temperature to be reduced below 60°C, before it is mixed with lower alcohols.
  • Such short chain alcohols may be present in the final formulation as solvents, examples include ethanol, propanol, propane diol and glycerol. If the succinic acid and such solvents are present at temperatures in excess of 60°C, then undesirable side products such as esters may be formed.
  • An intermediate composition may be formed which is a stable, pumpable liquid at temperatures below 60°C. This intermediate composition preferably consists of at least 40% by weight of partly neutralized succinic acid.
  • Dodecyl/tetradecyl succinic anhydride 300 kg/hour Potassium hydroxide (50% aq. soln.) 20 kg/hour Water 40 kg/hour Succinic anhydride, potassium hydroxide solution and water are supplied at ambient temperature from metering pumps at the rates described above, into a Pentax KMF8 (Trade Mark) high shear mixer.
  • This mixture is transferred directly from the outlet port of this mixer into the bottom of a buffer tank.
  • the buffer tank has a diameter of about 0.4m and a height of about 0.8m, giving a residence time of about 17 minutes.
  • the temperature in the buffer tank rises to 92°C as the exothermic hydrolysis reaction takes place.
  • the reacted material leaving from the top of the buffer tank has a composition of: Dodecyl/tetradecyl succinic acid (partly neutralised) 90% Water 10% and, when diluted to give a aqueous solution of 0.5% by weight, has a pH of 4.5.
  • the high active, partly neutralised succinic acid is mixed with a nonionic surfactant in the ratio of 1:1.
  • a finished composition is made by mixing the acid/ surfactant mixture with other detergent ingredients as follows (all given as % by weight): Succinic acid/nonionic surfactant 18 Ethanol & 1,2 propane diol 12 Sodium hydroxide 9* Alkyl benzene sulphonic acid 12 Sodium alkyl sulphate 2 Citric acid 7 Enzymes and minors 1 Miscellaneous (suds suppressor, perfume etc. ) 1 Water to balance to 100% *Level of sodium hydroxide may be varied in order to give finished pH8

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  • 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)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP19920201034 1992-04-10 1992-04-10 Procédé de préparation d'une composition détergente à haute activité contenant de l'acide succinique Expired - Lifetime EP0564719B1 (fr)

Priority Applications (10)

Application Number Priority Date Filing Date Title
ES92201034T ES2093766T3 (es) 1992-04-10 1992-04-10 Procedimiento para la fabricacion de una composicion detergente de alta actividad que contiene acido succinico.
EP19920201034 EP0564719B1 (fr) 1992-04-10 1992-04-10 Procédé de préparation d'une composition détergente à haute activité contenant de l'acide succinique
DE1992614932 DE69214932T2 (de) 1992-04-10 1992-04-10 Verfahren zur Herstellung einer hochaktiven Detergenszusammensetzung, Bernsteinsäure enthaltend
US08/318,612 US5719116A (en) 1992-04-10 1993-03-29 Process for manufacture of a high active detergent composition containing succinic acid
CA002117746A CA2117746C (fr) 1992-04-10 1993-03-29 Methode pour l'obtention d'une composition detergente tres active contenant de l'acide succinique
PCT/US1993/002943 WO1993021290A1 (fr) 1992-04-10 1993-03-29 Procede de preparation d'une composition de detergent tres puissante renfermant de l'acide succinique
JP5518371A JPH07505668A (ja) 1992-04-10 1993-03-29 コハク酸を含有する高活性洗剤組成物の製法
MX9302049A MX9302049A (es) 1992-04-10 1993-04-07 Procedimiento para fabricar una composicion detergente altamente activa que contiene acido succinico.
IE930279A IE930279A1 (en) 1992-04-10 1993-04-08 Process for manufacture of a high active detergent¹composition containing succinic acid
CN 93104023 CN1078998A (zh) 1992-04-10 1993-04-10 一种含琥珀酸的高活性洗涤组合物的制造方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP19920201034 EP0564719B1 (fr) 1992-04-10 1992-04-10 Procédé de préparation d'une composition détergente à haute activité contenant de l'acide succinique

Publications (2)

Publication Number Publication Date
EP0564719A1 true EP0564719A1 (fr) 1993-10-13
EP0564719B1 EP0564719B1 (fr) 1996-10-30

Family

ID=8210546

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19920201034 Expired - Lifetime EP0564719B1 (fr) 1992-04-10 1992-04-10 Procédé de préparation d'une composition détergente à haute activité contenant de l'acide succinique

Country Status (9)

Country Link
EP (1) EP0564719B1 (fr)
JP (1) JPH07505668A (fr)
CN (1) CN1078998A (fr)
CA (1) CA2117746C (fr)
DE (1) DE69214932T2 (fr)
ES (1) ES2093766T3 (fr)
IE (1) IE930279A1 (fr)
MX (1) MX9302049A (fr)
WO (1) WO1993021290A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU130040A1 (ru) * 1959-11-28 1959-11-30 С.В. Леви Способ получени алкенил нтарных кислот
GB2049723A (en) * 1979-04-20 1980-12-31 Kao Corp Detergent composition
EP0028850A1 (fr) * 1979-11-09 1981-05-20 Unilever N.V. Composition détergente liquide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU130040A1 (ru) * 1959-11-28 1959-11-30 С.В. Леви Способ получени алкенил нтарных кислот
GB2049723A (en) * 1979-04-20 1980-12-31 Kao Corp Detergent composition
EP0028850A1 (fr) * 1979-11-09 1981-05-20 Unilever N.V. Composition détergente liquide

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 10, no. 4 (C-322)(2061) 9 January 1986 & JP-A-60 163 838 ( KAO SEKKEN KK ) 26 August 1985 *

Also Published As

Publication number Publication date
IE930279A1 (en) 1993-10-20
ES2093766T3 (es) 1997-01-01
CA2117746C (fr) 1999-04-27
CN1078998A (zh) 1993-12-01
EP0564719B1 (fr) 1996-10-30
CA2117746A1 (fr) 1993-10-28
JPH07505668A (ja) 1995-06-22
DE69214932T2 (de) 1997-05-15
MX9302049A (es) 1994-07-29
DE69214932D1 (de) 1996-12-05
WO1993021290A1 (fr) 1993-10-28

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