WO1992013819A1 - Procede de production de dialkylethers ramifies - Google Patents

Procede de production de dialkylethers ramifies Download PDF

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Publication number
WO1992013819A1
WO1992013819A1 PCT/EP1992/000178 EP9200178W WO9213819A1 WO 1992013819 A1 WO1992013819 A1 WO 1992013819A1 EP 9200178 W EP9200178 W EP 9200178W WO 9213819 A1 WO9213819 A1 WO 9213819A1
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WO
WIPO (PCT)
Prior art keywords
alcohols
branched
dialkyl ethers
formula
hydroxy compounds
Prior art date
Application number
PCT/EP1992/000178
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German (de)
English (en)
Inventor
Rainer Jeschke
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1992013819A1 publication Critical patent/WO1992013819A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups

Definitions

  • the invention relates to a process for the preparation of branched dialkyl ethers by condensation of branched alcohols with hydroxy compounds in the presence of acidic catalysts.
  • Dialkyl ethers are important products of the chemical industry.
  • the use of diisoalkyl ethers as heat exchanger liquids is known from German patent application DE 34 24 702 A1.
  • Dialkyl ethers, in particular those with at least one long, branched alkyl radical, are also found as auxiliaries in the photo industry [JP 84/33 369], solvents for the suspension polymerization of vinyl acetate [JP 83/109 504] or components of skin creams [JP 73/5941] use.
  • a process for their preparation is based on aldehydes from Roelen 1 see oxosynthesis, which in the first stage condenses to the alpha, beta-unsaturated aldehydes, then in the presence of phosphoric acid are reacted with alcohols and finally hydrogenated [DE 2945050 AI] .
  • this process is not very economical from an economic point of view.
  • it is practically only suitable for the preparation of 2-ethylhexyl ethers, since 2-ethylhexanal is the only branched oxoaldehyde which is available in large quantities.
  • Another possibility for the production of dialkyl ethers is the reaction of alcohols with alkyl chlorides according to WILLIAMSON.
  • German patent application DE 39 11004 AI describes the condensation of branched alcohols in the presence of a catalyst system consisting of sulfuric acid or sulfonic acids and phosphorous acid. At temperatures around 240 ° C, however, branched olefins and no ethers are obtained in practically quantitative amounts.
  • the object of the invention was therefore to develop a process for the preparation of dialkyl ethers which is free from the disadvantages.
  • the invention relates to a process for the preparation of branched dialkyl ethers, which is characterized in that branched primary alcohols of the formula (I),
  • R - * and R2 independently of one another represent linear alkyl radicals having 2 to 20 carbon atoms, in the presence of sulfonic acids condensed with hydroxy compounds at temperatures of 150 to 200 ° C.
  • dialkyl ethers with high selectivity are formed in the acid-catalyzed condensation of branched alcohols with hydroxy compounds if the reaction is carried out in the temperature range from 150 to 200.degree. This overcome the prejudice that only olefins are produced in this type of implementation.
  • Branched primary alcohols for the preparation of the dialkyl ethers are branched oxo alcohols which are accessible via Roelen's oxosynthesis (hydroformylation).
  • short-chain olefins such as propylene, butene-1 or pentene-1
  • synthesis gas in the presence of rhodium / triphenylphosphine catalysts.
  • the resulting aldehydes are subjected to base-catalyzed aldol condensation and hydrogenation, in which beta-alkyl-branched alcohols are obtained.
  • beta-alkyl-branched alcohols are obtained.
  • Typical examples of this are 2-ethylhexanol, 2-propylheptanol or 2-butyloctanol.
  • Preferred branched oxo alcohols as starting materials for the preparation of dialkyl ethers are alcohols of the formula (II) in which R 1 and R 2 represent alkyl radicals having 2 to 8 carbon
  • Guerbet alcohols which are formed in the base-catalyzed condensation of linear saturated or unsaturated alcohols having 6 to 22 carbon atoms via the intermediate stages of the aldehydes and aldols can also be used as branched primary alcohols for the preparation of the dialkyl ethers [Soap Cosm.Chem. Spec, 52 (1987)]. Typical examples are 2- butyloctanol, 2-hexyldecanol, 2-0ctyldodecanol, 2-decyltetra- decanol, 2-dodecylhexadecanol or 2-tetradecyloctadecanol.
  • Preferred Guerbet alcohols for the production of dialkyl ethers are alcohols of the formula (II) in which R 1 and R 2 are alkyl radicals
  • Branched and linear alcohols are suitable as hydroxy compounds.
  • the branched alcohols are self-condensed; in this case the hydroxy compounds used correspond to the alcohols of the formula (I).
  • Dialkyl ethers with branches in both alkyl chains are formed.
  • hydroxy components are primary, predominantly linear alcohols of the formula (II),
  • R3 is an aliphatic hydrocarbon radical having 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds.
  • Typical examples are capronic alcohol, caprylic alcohol, capric alcohol, myristyl alcohol, lauryl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, behenyl alcohol or erucyl alcohol.
  • R 3 represents alkyl radicals having 8 to 18 carbon atoms.
  • the alcohols can also be used in the form of technical cuts, such as those obtained by high-pressure hydrogenation of fatty acid methyl esters based on fats and oils. Furthermore, the Largely linear oxo alcohols from Roelen 1 see oxosynthesis as suitable if they have a corresponding chain length.
  • the condensation takes place in the presence of acidic catalysts of the sulfonic acid type.
  • the sulfonic acids can be used in concentrations of 0.1 to 5% by weight, based on the starting alcohols. In view of a high reaction rate and minimal formation of undesired olefinic by-products, it has proven to be optimal to use the sulfonic acids in amounts of 1 to 2% by weight.
  • the condensation is carried out at temperatures in the range from 150 to 200.degree. In view of a sufficient reaction rate and a minimal formation of undesired olefinic by-products, it has proven to be optimal to carry out the reaction at temperatures from 160 to 190 ° C.
  • the reaction time is determined by the catalyst concentration and the reaction temperature.
  • the reaction can usually be carried out over a period of 1 to 36 h, preferably 2 to 30 h.
  • the starting materials and the catalyst are introduced and heated.
  • the crude product can then, if appropriate after neutralizing the acid catalyst, be purified by distillation in vacuo.
  • the dialkyl ethers obtainable by the process according to the invention are high-boiling, temperature-resistant substances which are suitable, for example, as heat exchanger liquids.
  • Octyloxy-2-hexyldecane 758.3 g (2.9 mol) of 2-hexyldecanol and 64.7 g of a 70% by weight aqueous solution of sulfosuccinic acid were heated to 170 to 184 ° C. over 6 h and in four portions with 1508 g (11, 6 mol) of n-octanol are added.
  • the crude reaction product was worked up analogously to Example 2. There were 400 g Obtain 1-octyloxy-2-hexyldecane in the form of a colorless oil (bp 160 ° C / 0.06 mbar).

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

Abstract

On peut produire des dialkyléthers ramifiés en condensant avec des composés hydroxyles des alcools primaires ramifiés ayant la formule (I), dans laquelle R1 et R2 représentent indépendamment l'un de l'autre des résidus alkyle linéaires ayant 2 à 20 atomes de carbone, en présence d'acides sulfoniques à des températures comprises entre 150 et 200 °C. Ces produits sont utiles comme liquides échangeurs de chaleur.
PCT/EP1992/000178 1991-02-06 1992-01-28 Procede de production de dialkylethers ramifies WO1992013819A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4103489.9 1991-02-06
DE19914103489 DE4103489A1 (de) 1991-02-06 1991-02-06 Verfahren zur herstellung von verzweigten dialkylethern

Publications (1)

Publication Number Publication Date
WO1992013819A1 true WO1992013819A1 (fr) 1992-08-20

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/000178 WO1992013819A1 (fr) 1991-02-06 1992-01-28 Procede de production de dialkylethers ramifies

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DE (1) DE4103489A1 (fr)
WO (1) WO1992013819A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1008796C2 (nl) * 1997-04-02 1998-11-03 Snam Progetti Werkwijze voor de bereiding van ethers uit alcoholen.
WO2009064828A1 (fr) * 2007-11-13 2009-05-22 E. I. Du Pont De Nemours And Company Procédé de préparation d'une composition comprenant au moins deux éthers dialkyliques différents
SE2151462A1 (en) * 2021-12-01 2023-06-02 Colabitoil Sweden Ab Biofuel and method of synthesis of the same

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4301820C2 (de) * 1993-01-23 1996-04-25 Henkel Kgaa Schäumende Emulsionen, Verfahren zu ihrer Herstellung und ihre Verwendung
DE4308794C1 (de) * 1993-03-18 1994-04-21 Henkel Kgaa Verfahren zur Herstellung von festen Esterquats mit verbesserter Wasserdispergierbarkeit
DE4311445C1 (de) * 1993-04-07 1994-10-06 Henkel Kgaa Multiple W/O/W-Emulsionen, Verfahren zu deren Herstellung und ihre Verwendung
DE19517049B4 (de) * 1995-05-10 2005-06-16 Cognis Deutschland Gmbh & Co. Kg Verfahren zur Herstellung von Dialkylethern

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2844534A (en) * 1952-10-20 1958-07-22 Exxon Research Engineering Co High molecular weight branched-chain ethers of lubricating grade
EP0170076A1 (fr) * 1984-07-05 1986-02-05 BASF Aktiengesellschaft Fluides de transfert de chaleur

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2844534A (en) * 1952-10-20 1958-07-22 Exxon Research Engineering Co High molecular weight branched-chain ethers of lubricating grade
EP0170076A1 (fr) * 1984-07-05 1986-02-05 BASF Aktiengesellschaft Fluides de transfert de chaleur

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE. 1949, PARIS FR Seiten 333 - 337; R. PERRON UND C.PAQUOT: 'Préparation des éthers-oxydes symétriques dérivés des alcools aliphatiques saturés à longue chaine' *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1008796C2 (nl) * 1997-04-02 1998-11-03 Snam Progetti Werkwijze voor de bereiding van ethers uit alcoholen.
US6218583B1 (en) 1997-04-02 2001-04-17 Snamprogetti S.P.A. Process for the production of ethers from alcohols
WO2009064828A1 (fr) * 2007-11-13 2009-05-22 E. I. Du Pont De Nemours And Company Procédé de préparation d'une composition comprenant au moins deux éthers dialkyliques différents
SE2151462A1 (en) * 2021-12-01 2023-06-02 Colabitoil Sweden Ab Biofuel and method of synthesis of the same
WO2023101592A1 (fr) * 2021-12-01 2023-06-08 Colabitoil Sweden Ab Biocarburant et son procédé de synthèse

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DE4103489A1 (de) 1992-08-13

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