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WO1994007840A1 - Hydroxyethers melanges interieurement stables - Google Patents

Hydroxyethers melanges interieurement stables Download PDF

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Publication number
WO1994007840A1
WO1994007840A1 PCT/EP1993/002601 EP9302601W WO9407840A1 WO 1994007840 A1 WO1994007840 A1 WO 1994007840A1 EP 9302601 W EP9302601 W EP 9302601W WO 9407840 A1 WO9407840 A1 WO 9407840A1
Authority
WO
WIPO (PCT)
Prior art keywords
epoxides
carbon atoms
fatty acid
formula
ring opening
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.)
Ceased
Application number
PCT/EP1993/002601
Other languages
German (de)
English (en)
Inventor
Rita Köster
Peter Daute
Gerhard Stoll
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to FI951552A priority Critical patent/FI951552A7/fi
Priority to EP93920819A priority patent/EP0662947A1/fr
Publication of WO1994007840A1 publication Critical patent/WO1994007840A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/708—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form

Definitions

  • the invention relates to internal hydroxy mixed ethers which are obtained by ring opening epoxides of unsaturated fatty acid esters with fatty alcohol polyglycol ethers, a process for their preparation and their use as auxiliaries in solids dewatering.
  • the invention relates to internal hydroxy mixed ethers which are obtained by epoxides of unsaturated fatty acid esters with fatty alcohol polyglycol ethers of the formula (I),
  • R ⁇ represents a linear or branched, aliphatic hydrocarbon radical having 4 to 22 carbon atoms and R- ⁇ represents hydrogen or a methyl group, is subjected to a ring opening.
  • the internal hydroxy mixed ethers according to the invention have significantly better cold behavior, in particular lower pour points, compared to the known terminal hydroxy mixed ethers of DE-A-39 18 274, with comparatively good, e.g. T. even have slightly improved application engineering properties.
  • Another object of the invention relates to a process for the preparation of internal hydroxy mixed ethers, in which Epoxides of unsaturated fatty acid esters with fatty alcohol polyglycol ethers of the formula (I),
  • R 1 is a linear or branched, aliphatic hydrocarbon radical having 4 to 22 carbon atoms and R 2 is hydrogen or a methyl group, is subjected to a ring opening.
  • Epoxides of unsaturated fatty acid esters are, for example, addition products of oxygen to the double bonds of mono- or polyunsaturated fatty acid lower alkyl esters of the formula (II),
  • R ⁇ CO stands for an unsaturated acyl radical with 16 to 22 carbon atoms and R ⁇ stands for a linear or branched alkyl radical with 1 to 4 carbon atoms.
  • Typical examples are epoxidized methyl, ethyl, propyl or butyl esters of palmoleic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, gadoleic acid and erucic acid and their technical mixtures.
  • the epoxides used can be completely epoxidized, but they can also contain double bonds; the degree of epoxidation, based on the double bonds available, is preferably 50 to 100% and in particular 70 to 95%.
  • the preferred feed is oleic acid methyl ester epoxide with an epoxy oxygen content of 4.5 to 5.1% by weight.
  • epoxidized unsaturated fatty acid glycerol esters of the formula (III) are also suitable as starting materials,
  • R ⁇ CO, R ⁇ CO and R ⁇ CO independently of one another represent unsaturated acyl radicals having 16 to 24 carbon atoms.
  • Typical examples are epoxides of unsaturated triglycerides of plant or animal origin, such as soybean oil, rape oil, olive oil, sunflower oil, cottonseed oil, peanut oil, linseed oil, beef tallow or fish oil.
  • These feedstocks can also contain saturated portions; Usually, however, epoxides of such fatty acid glycerol esters are used which have an iodine number in the range from 50 to 150, preferably up to 115. As already described, both completely and partially epoxidized esters can be used as starting materials.
  • the preferred feedstock is epoxidized Soybean oil with an epoxy content of 4.5 to 6.5% by weight.
  • Fatty alcohol polyglycol ethers of the formula (I) are suitable as the nucleophile for the ring opening of the insert epoxides mentioned.
  • Typical examples are adducts of 1 to 30, preferably 2 to 10, moles of ethylene and / or propylene oxide with butanol, pentanol, capro alcohol, caprylic alcohol, capric alcohol, lauryl alcohol, myristyl alcohol, isotridecyl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, isostyl alcohol ,
  • Elaidyl alcohol petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol and erucyl alcohol, and their technical mixtures, such as those obtained in the hydrogenation of Fettsron fatty acid methyl ester fractions or aldehydes from Roelen's oxosynthesis.
  • the epoxides and the fatty alcohol polyglycol ethers can usually be used in a molar ratio of 1: 0.5 to 1: 1.5, preferably 1: 0.9 to 1: 1.1, based on the epoxy content.
  • the internal hydroxy mixed ethers to be used according to the invention support the dewatering of solid suspensions, are readily biodegradable and are characterized by low pour points.
  • Another object of the invention therefore relates to their use as auxiliaries for the dewatering of finely divided solid suspensions, such as iron ore concentrates, quartz sand, hard coal or coke.
  • Another important area of application is the use of the internal hydroxy mixed ethers to be used according to the invention as auxiliaries in the dewatering of solid suspensions which are used in waste paper processing, e.g. B. in the de-inking process or filler flotation.
  • the internal hydroxy mixed ethers according to the invention can be used individually; for the dewatering of certain solids, however, it can be advantageous to combine products of different chain lengths or different degrees of alkoxylation with one another in order to exploit synergies in their physicochemical properties. In the same way, it can be advantageous to use combinations of the internal hydroxy mixed ethers with other already known ionic or nonionic drainage aids. According to an advantageous embodiment of the process according to the invention, the internal hydroxy mixed ethers are used in amounts of 10 to 500, preferably 50 to 300 and in particular 150 to 250 g, based on solids content, per ton of solid.
  • Viscosity (according to Höppler) 60 mPa.s hydroxyl number 81
  • Residual epoxy oxygen content 0.1% by weight viscosity (Höppler) 33 mPa.s hydroxyl number 131
  • Products A) and B) are inventive, product C) is used for comparison.
  • Quartz sand of the following grain size was used for the drainage tests:
  • the tests were carried out in a cup centrifuge, with which centrifuge parameters from 15 to 2000 can be achieved.
  • Perforated plates with sieve openings of 0.1 x 2 mm were used as the sieve covering.
  • the drainage aids were used in aqueous solutions; all concentration data are based on the solid.
  • the operational filter application of an iron ore concentrate was used for the drainage tests.
  • the tests were carried out in a pressure filter (60 cm 2 ) at a pressure difference of 2 bar.
  • the filter feed had a solids content of 65% by weight and the sample amount was 120 ml.
  • the drainage aids were again used in aqueous solutions; all concentration data are based on the solid.
  • After dewatering, the moist solids were weighed out, dried to constant weight at 100 ° C and the residual moisture in% rel. certainly. All test results represent means of duplicate determinations. The results are summarized in Table 2.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

On obtient des hydroxyéthers mélangés intérieurement stables dans la mesure où l'on soumet des époxydes d'esters insaturés d'acides gras à une ouverture avec des polyglycoléthers d'alcool gras de la formule (I), dans laquelle R1 désigne un reste hydrocarbure aliphatique linéaire ou ramifié ayant 4 à 22 atomes de carbone et R2 désigne l'hydrogène ou un groupe méthyle. Les produits conviennent comme auxiliaires pour la dessication de matières solides et se caractérisent par leur bonne biodégradabilité, leur faible pouvoir moussant et un point de solidification bas.
PCT/EP1993/002601 1992-10-02 1993-09-24 Hydroxyethers melanges interieurement stables Ceased WO1994007840A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
FI951552A FI951552A7 (fi) 1992-10-02 1993-09-24 Sisäisiä hydroksisekaeettereitä
EP93920819A EP0662947A1 (fr) 1992-10-02 1993-09-24 Hydroxyethers melanges interieurement stables

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4233219A DE4233219A1 (de) 1992-10-02 1992-10-02 Innenständige Hydroxymischether
DEP4233219.2 1992-10-02

Publications (1)

Publication Number Publication Date
WO1994007840A1 true WO1994007840A1 (fr) 1994-04-14

Family

ID=6469525

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1993/002601 Ceased WO1994007840A1 (fr) 1992-10-02 1993-09-24 Hydroxyethers melanges interieurement stables

Country Status (6)

Country Link
EP (1) EP0662947A1 (fr)
CA (1) CA2146236A1 (fr)
DE (1) DE4233219A1 (fr)
FI (1) FI951552A7 (fr)
WO (1) WO1994007840A1 (fr)
ZA (1) ZA937314B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19622967C1 (de) * 1996-06-07 1998-01-29 Henkel Kgaa Wäßrige Perlglanzkonzentrate
WO2001000567A1 (fr) * 1999-06-29 2001-01-04 Akzo Nobel Nv Composes de nitriles epoxydes, leur procede d'elaboration et leur utilisation comme agents nettoyants

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19526501A1 (de) * 1995-07-20 1997-01-23 Basf Ag Hydroxymischether durch Ringöffnung von Epoxiden ungesättigter Fettsäureester mit Polyglykolethern und ihre Verwendung als biologisch abbaubarer Entschäumer

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0127810A1 (fr) * 1983-05-21 1984-12-12 Henkel Kommanditgesellschaft auf Aktien Acides hydroxyalkoxycarboxyliques et leurs sels, leurs procédés de préparation ainsi que leur utilisation
WO1991011424A1 (fr) * 1990-01-26 1991-08-08 Henkel Kommanditgesellschaft Auf Aktien Composes alcoxyles prepares a partir de derives d'acide carboxylique epoxydes
WO1992019577A1 (fr) * 1991-05-08 1992-11-12 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de produits a ouverture de cycle epoxy ayant une teneur determinee en oxygene epoxy residuel

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0127810A1 (fr) * 1983-05-21 1984-12-12 Henkel Kommanditgesellschaft auf Aktien Acides hydroxyalkoxycarboxyliques et leurs sels, leurs procédés de préparation ainsi que leur utilisation
WO1991011424A1 (fr) * 1990-01-26 1991-08-08 Henkel Kommanditgesellschaft Auf Aktien Composes alcoxyles prepares a partir de derives d'acide carboxylique epoxydes
WO1992019577A1 (fr) * 1991-05-08 1992-11-12 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de produits a ouverture de cycle epoxy ayant une teneur determinee en oxygene epoxy residuel

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19622967C1 (de) * 1996-06-07 1998-01-29 Henkel Kgaa Wäßrige Perlglanzkonzentrate
WO2001000567A1 (fr) * 1999-06-29 2001-01-04 Akzo Nobel Nv Composes de nitriles epoxydes, leur procede d'elaboration et leur utilisation comme agents nettoyants
US6770679B1 (en) 1999-06-29 2004-08-03 Akzo Nobel N.V Compounds from epoxidised nitriles, process for their production and use as cleaning agents

Also Published As

Publication number Publication date
CA2146236A1 (fr) 1994-04-14
FI951552A0 (fi) 1995-03-31
EP0662947A1 (fr) 1995-07-19
ZA937314B (en) 1994-04-05
DE4233219A1 (de) 1994-04-07
FI951552L (fi) 1995-03-31
FI951552A7 (fi) 1995-03-31

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