WO1999003869A2 - Procede de preparation d'alkylglycosides - Google Patents

Procede de preparation d'alkylglycosides Download PDF

Info

Publication number
WO1999003869A2
WO1999003869A2 PCT/EP1998/004283 EP9804283W WO9903869A2 WO 1999003869 A2 WO1999003869 A2 WO 1999003869A2 EP 9804283 W EP9804283 W EP 9804283W WO 9903869 A2 WO9903869 A2 WO 9903869A2
Authority
WO
WIPO (PCT)
Prior art keywords
carried out
glucose
alcohol
microwave radiation
water
Prior art date
Application number
PCT/EP1998/004283
Other languages
German (de)
English (en)
Other versions
WO1999003869A3 (fr
Inventor
Oliver Rhode
Sandra Witt
Ingo Hardacker
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 WO1999003869A2 publication Critical patent/WO1999003869A2/fr
Publication of WO1999003869A3 publication Critical patent/WO1999003869A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
    • B01J19/122—Incoherent waves
    • B01J19/126—Microwaves

Definitions

  • the invention relates to the production of alkyl glycosides by acetalization of glycoses with alcohols under microwave radiation and to a process for the production of dried glycoses from water-containing glycose preparations under microwave radiation.
  • Alkyl glycosides are nonionic surfactants, which are becoming increasingly important due to their excellent detergent properties and high ecotoxicological compatibility. They are usually prepared from glycoses and fatty alcohols, which are acetalized in the presence of acidic catalysts. The catalyst is then neutralized with a base. In order to shift the reaction equilibrium to the side of the products, the water of reaction which forms is distilled off. To avoid the polymerization of the glycoses, the fatty alcohol is used in a large excess. The acetalization is therefore usually followed by a step in which the unreacted alcohol is removed by distillation.
  • the task could be solved if the acetalization reaction is carried out under microwave radiation.
  • the present invention therefore relates to a process for the preparation of alkyl glycosides by acetalization reaction of aliphatic alcohols with glycoses in the presence of an acidic catalyst, characterized in that the acetalization reaction is carried out under microwave radiation.
  • alkyl glycosides means reaction products of glycoses such as glucose, fructose, mannose, galactose, talose, gulose, allose, old rose, idose, arabinose, xylose, lyose and ribose with aliphatic primary alcohols, the alcohol being more than an acetal bond is bound to the glycose and the glycose can in turn be linked to one another by glycosidic linkage.
  • the number of linked glycoses is characterized by the so-called degree of oligomerization and is within the scope of the invention at values between 1 and 10, preferably between 1 and 3 and in particular between 1.1 and 1.5.
  • the degree of oligomerization is a quantity to be determined analytically, which can also assume fractional numerical values.
  • the glycoses in particular glucose
  • the aliphatic alcohols preferably with aliphatic primary alcohols having 6 to 22 carbon atoms.
  • suitable alcohols are capronic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol, linoleyl alcohol.
  • fatty alcohols with 12 to 18 carbon atoms such as coconut, palm, palm kernel or tallow fatty alcohol are preferred.
  • Glucose is preferably used as glycose in the process according to the invention.
  • Glucose is available on the market as an anhydrous, finely divided powder, as a glucose monohydrate with one mole of crystal water and as a glucose syrup.
  • the glucose syrup is a syrup-like glucose / water mixture with an active substance content of glucose which varies between 70 and 97% by weight. All of these forms of glucose can be used in the process according to the invention. If water-containing glucose products are involved, it is preferred to dry them with the acid catalyst before bringing them into contact and to convert them into the anhydrous form. Drying can be carried out, for example, by thermal treatment, but dark-colored decomposition products often occur.
  • Another object of the present invention therefore relates to a process for the preparation of dried glycoses, in particular glucose, by drying water-containing glycose preparations, characterized in that the water-containing glycose preparations are first suspended in aliphatic alcohols and then dried under microwave radiation.
  • the already mentioned glucose monohydrates and glucose syrups are suitable as water-containing glycose preparations, in particular glucose preparations.
  • Suitable aliphatic alcohols are the alcohols already mentioned in connection with the acetalization, in particular those which are liquid at room temperature (about 20 to 25 ° C.).
  • the water-containing glycose preparations are suspended in the alcohols in a weight ratio of 1: 2 to 1:10, in particular 1: 2.5 to 1: 4.5.
  • the suspension can be carried out in the usual way, for example by means of a stirrer or by means of ultrasound.
  • the suspensions obtained are then subjected to microwave radiation, preferably the microwave radiation is carried out with a high-frequency power of 5 to 100 Wh / kg, preferably 10 to 50 Wh / kg.
  • the high-frequency power is given in watt-hours (Wh) per kilogram batch.
  • the drying is particularly advantageously carried out at temperatures below the melting point of the glycoses, in particular below the melting point of glucose, particularly preferably at temperatures from 30 to 80 ° C. It has proven to be useful if the drying is carried out in vacuo, preferably at 10 to 50 mbar.
  • the water is preferably continuously removed by distillation, the drying being considered complete when no further water separates.
  • the amount of water separated can be determined, for example, by freezing the collected water in a cold trap. After drying has ended, the excess alcohol is generally distilled off in a gentle manner known per se.
  • the dried glycoses generally have residual water contents below 5, preferably below 3% by weight.
  • drying of the water-containing glycose preparations can also be combined with the usual thermal drying.
  • drying is first carried out thermally in the customary manner and, to remove the remaining amounts of water, the drying described above is used under microwave radiation.
  • the glycoses dried in the manner according to the invention or in the customary manner can be used for the acetalization according to the invention under microwave radiation.
  • the preferably dried glycoses are reacted with the alcohols already described in a molar ratio of 1: 2 to 1:10, preferably 1: 3 to 1: 6.
  • the acetalization takes place after addition of the acidic catalysts.
  • All acidic compounds, including the so-called Lewis acids are generally suitable as catalysts.
  • Sulfuric acid, phosphoric acid, aliphatic and / or aromatic sulfonic acids, in particular p-toluenesulfonic acid, and the sulfonic acid ion exchange resins are particularly suitable.
  • the quantities of acidic catalysts used correspond the usual amounts and are preferably in the range from 0.001 to 1% by weight, based on the total batch.
  • the acetalization reaction of the glycose with the alcohol in the presence of the catalyst can be carried out in a variety of ways.
  • a partial amount of the alcohol is initially charged with the catalyst and a suspension of the glycose in the remaining amount of alcohol is gradually added.
  • a suspension of the glycose in a partial amount of the alcohol is introduced and about one third of the required amount of catalyst, suspended in a part of the alcohol, is added. The rest of the required amount of catalyst is metered in later in portions.
  • the acetalization is carried out under microwave radiation, preferably under microwave radiation with a high-frequency power of 10 to 200 Wh / kg, in particular of 20 to 90 Wh / kg.
  • the microwave radiation is preferably carried out unpulsed.
  • the acetalization is favored by heating the reaction mixture to temperatures from 70 to 140, preferably from 100 to 120 ° C.
  • the water of reaction formed is preferably continuously distilled off. To ensure this, a vacuum of 10 to 50 mbar is preferably applied.
  • the end of the reaction is considered reached when no further water of reaction separates out.
  • the water can be collected, for example, by freezing it in a cold trap.
  • the end of the reaction is usually reached after 2 to 3 hours and is therefore much faster than the usual production methods.
  • the acetalization is preferably carried out batchwise.
  • the microwave laboratory systems commonly used on the market for synthesis for example M Lavis 1000 from MLS, can be used for the microwave radiation.
  • the catalyst can be neutralized, as usual, by adding organic or inorganic basic compounds; if desired, a pH of at least 8, preferably 8 to 10, can be set in addition to the neutralization of the acid catalyst.
  • the excess alcohol can also be distilled off in a conventional manner, for example by means of falling film evaporators or thin film evaporators, to residual amounts of preferably less than 5% by weight.
  • Information on suitable basic catalysts and the gentle distillation of the excess alcohol can be found, for example, in European patent application EP-A-362 671.
  • the drying of the glycoses is carried out under microwave irradiation and the acetalization in the presence of an acidic catalyst under microwave irradiation in a joint reaction.
  • the water-containing glycose preparation is first suspended with the aliphatic alcohols in the manner described above and, as described, freed of water (dried) with microwave radiation.
  • the water which has been freed from water is not freed from the excess alcohol, but instead is used immediately for the acetalization reaction which takes place in the manner described above in the presence of an acidic catalyst and under microwave radiation. It may be necessary to replenish some of the alcohol so that the molar ratios of glycose to alcohol required for the acetalization reaction are present.
  • the same alcohol is expediently used for drying and for the acetalization reaction under microwave radiation.
  • light-colored, solid alkyl glycosides are obtained in a gentle and rapid manner and have degrees of oligomerization from 1 to 10, preferably from 1 to 3 and in particular from 1.1 to 1.5.
  • the distilled water was frozen out in a cold trap.
  • Example 1 The device mentioned in Example 1 was used to control the temperature, the vacuum and the microwave radiation. After the reaction had ended, the mixture was neutralized with 0.093 g of a 50% by weight sodium hydroxide solution and with 0.1 g of magnesium oxide. The excess alcohol was removed by distillation. A dodecanol glucoside with a degree of oligomerization of 1.43 was obtained.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Toxicology (AREA)
  • Electromagnetism (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)

Abstract

L'invention concerne la préparation d'alkylglycosides par acétalisation de glucoses avec des alcools sous injection d'un faisceau de micro-ondes. L'invention concerne également un procédé de préparation de glucoses séchés issus de préparations glucosiques, par injection d'un faisceau de micro-ondes.
PCT/EP1998/004283 1997-07-18 1998-07-10 Procede de preparation d'alkylglycosides WO1999003869A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1997130836 DE19730836A1 (de) 1997-07-18 1997-07-18 Verfahren zur Herstellung von Alkylglykosiden
DE19730836.8 1997-07-18

Publications (2)

Publication Number Publication Date
WO1999003869A2 true WO1999003869A2 (fr) 1999-01-28
WO1999003869A3 WO1999003869A3 (fr) 1999-04-08

Family

ID=7836112

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/004283 WO1999003869A2 (fr) 1997-07-18 1998-07-10 Procede de preparation d'alkylglycosides

Country Status (2)

Country Link
DE (1) DE19730836A1 (fr)
WO (1) WO1999003869A2 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006232811A (ja) * 2005-01-31 2006-09-07 Japan Science & Technology Agency グリコシド化合物の製造方法
CN102250160A (zh) * 2011-05-30 2011-11-23 浙江赞宇科技股份有限公司 一种用微波-超声波协同催化制备烷基糖苷的方法
CN102786557A (zh) * 2011-05-19 2012-11-21 扬州晨化科技集团有限公司 制备十四烷基葡萄糖苷的方法
CN102786560A (zh) * 2011-05-19 2012-11-21 扬州晨化科技集团有限公司 制备月桂烷基葡萄糖苷的方法
CN103232497A (zh) * 2013-04-09 2013-08-07 浙江赞宇科技股份有限公司 一种烷基糖苷的制备方法
CN103319549A (zh) * 2013-07-18 2013-09-25 扬州大学 一种烷基糖苷的合成方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10117208A1 (de) * 2001-04-06 2002-10-10 Wolff Walsrode Ag Verfahren zur Herstellung von niederviskosen, wässrigen Celluloseetherlösungen

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0036309A2 (fr) * 1980-03-14 1981-09-23 Preston Leonard Veltman Procédé pour la préparation d'un produit en particules à partir d'une solution d'hydrates de carbone
EP0662483A1 (fr) * 1994-01-10 1995-07-12 Coöperatie Suiker Unie U.A. Procédé de préparation de dérivés de polysaccharides
DE4404633A1 (de) * 1994-02-14 1995-08-17 Henkel Kgaa Verfahren zur Herstellung praktisch wasserfreier Zuckertenside

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0036309A2 (fr) * 1980-03-14 1981-09-23 Preston Leonard Veltman Procédé pour la préparation d'un produit en particules à partir d'une solution d'hydrates de carbone
EP0662483A1 (fr) * 1994-01-10 1995-07-12 Coöperatie Suiker Unie U.A. Procédé de préparation de dérivés de polysaccharides
DE4404633A1 (de) * 1994-02-14 1995-08-17 Henkel Kgaa Verfahren zur Herstellung praktisch wasserfreier Zuckertenside

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
LIMOUSIN, C. ET AL.: "Solvent-free synthesis of decyl D-glucopyranosides under focused microwave irradiation" J. CARBOHYDR. CHEM., Bd. 16, Nr. 3, 1997, Seiten 327-342, XP002089930 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006232811A (ja) * 2005-01-31 2006-09-07 Japan Science & Technology Agency グリコシド化合物の製造方法
CN102786557A (zh) * 2011-05-19 2012-11-21 扬州晨化科技集团有限公司 制备十四烷基葡萄糖苷的方法
CN102786560A (zh) * 2011-05-19 2012-11-21 扬州晨化科技集团有限公司 制备月桂烷基葡萄糖苷的方法
CN102786560B (zh) * 2011-05-19 2014-12-17 扬州晨化新材料股份有限公司 制备月桂烷基葡萄糖苷的方法
CN102250160A (zh) * 2011-05-30 2011-11-23 浙江赞宇科技股份有限公司 一种用微波-超声波协同催化制备烷基糖苷的方法
CN102250160B (zh) * 2011-05-30 2013-12-18 浙江赞宇科技股份有限公司 一种用微波-超声波协同催化制备烷基糖苷的方法
CN103232497A (zh) * 2013-04-09 2013-08-07 浙江赞宇科技股份有限公司 一种烷基糖苷的制备方法
CN103232497B (zh) * 2013-04-09 2015-11-18 浙江赞宇科技股份有限公司 一种烷基糖苷的制备方法
CN103319549A (zh) * 2013-07-18 2013-09-25 扬州大学 一种烷基糖苷的合成方法
CN103319549B (zh) * 2013-07-18 2015-08-19 扬州大学 一种烷基糖苷的合成方法

Also Published As

Publication number Publication date
WO1999003869A3 (fr) 1999-04-08
DE19730836A1 (de) 1999-01-21

Similar Documents

Publication Publication Date Title
EP0437460B1 (fr) Procede de production directe d'alkylglucosides
EP0301298B1 (fr) Procédé de préparation de glucosides d'alkyle
EP0357969B1 (fr) Procédé de préparation des alkylglycosides d'oligo- et/ou polysaccharides
DE69612745T2 (de) Verfahren zur herstellung von hydroxyalkylamiden
EP0495174B1 (fr) Procédé de préparation d'alkylglycosides et d'alkylpolyglycosides
EP0448799A2 (fr) Procédé pour la préparation de tensides contenant des hydrates de carbone
WO1993021196A1 (fr) Procede de production d'alkylglucosides
DE10122255C1 (de) Verfahren zur Herstellung von Tensidgemischen
EP0514627B1 (fr) Procédé de préparation d'alcoylpolyglycosides
EP0613482B1 (fr) Procede de fabrication d'alkyl- et/ou d'alcenyloligoglucosides
WO1999003869A2 (fr) Procede de preparation d'alkylglycosides
EP0609274B1 (fr) Procede de fabrication de pates d'alkyloligoglucoside de couleur claire
EP0249013B1 (fr) Procédé de synthèse d'oligoglycosides d'alkyle
DE3842541A1 (de) Verfahren zur herstellung von oberflaechenaktiven alkylglucosiden
EP0252241B1 (fr) Méthode de préparation de butyloligoglycosides
WO1991019723A1 (fr) Procede pour eclaircir des alkylglycosides tensioactifs decolores et pour traiter le produit blanchi
WO1993010133A1 (fr) Procede de preparation d'oligoglucosides d'alkyle a teneur reduite en polyglucose
DE4431856A1 (de) Verfahren zur Herstellung von Alkylpolyglycosiden
EP0617045A2 (fr) Procédé de préparation en continu d'alkylglycosides
DE4429134A1 (de) Verfahren zur Herstellung von Alkyl- und/oder Alkenyloligoglykosiden
DE4337035A1 (de) Verfahren zur Herstellung von Alkyl- und/oder Alkenyloligoglykosidisethionaten
WO1993011142A1 (fr) Procede de fabrication d'oligoglucosides d'alkyle inferieur
DE4431858A1 (de) Verfahren zur Herstellung von Alkylpolyglycosiden
EP0615974A1 (fr) Procédé de préparation d'alkylglycosides
DE19714255A1 (de) Verfahren zur Herstellung von Alkyl- und/oder Alkenyloligoglykosiden

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): JP US

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

AK Designated states

Kind code of ref document: A3

Designated state(s): JP US

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase