EP1212290A1 - Procede de production d'amides d'acide gras - Google Patents

Procede de production d'amides d'acide gras

Info

Publication number
EP1212290A1
EP1212290A1 EP00974367A EP00974367A EP1212290A1 EP 1212290 A1 EP1212290 A1 EP 1212290A1 EP 00974367 A EP00974367 A EP 00974367A EP 00974367 A EP00974367 A EP 00974367A EP 1212290 A1 EP1212290 A1 EP 1212290A1
Authority
EP
European Patent Office
Prior art keywords
fatty acid
reaction
catalyst
ammonia
pressure
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.)
Withdrawn
Application number
EP00974367A
Other languages
German (de)
English (en)
Inventor
Bernhard Gutsche
Christophe Sicre
Rene Armengaud
Jean Rigal
Gerhard Wollmann
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.)
BASF Personal Care and Nutrition GmbH
Original Assignee
Cognis Deutschland GmbH and Co KG
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 Cognis Deutschland GmbH and Co KG filed Critical Cognis Deutschland GmbH and Co KG
Publication of EP1212290A1 publication Critical patent/EP1212290A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines

Definitions

  • the invention relates to a process for producing fatty acid amides from fatty acid alkyl esters and ammonia in the presence of a catalyst.
  • Primary fatty acid amides e.g. B. stearic acid amide, oleic acid amide, erucic acid amide, can be used as lubricants and antiblocking agents (slip agents) in the plastics industry, as intermediates for organic syntheses and as foam stabilizers in detergents and cleaning agents.
  • Fatty acid + ammonia fatty acid amide + water.
  • Fatty acid amide + water fatty acid + ammonia
  • Fatty acid amide water + fatty acid nitrile
  • Fatty acid methyl ester + water fatty acid + methanol.
  • the fatty acid then reacts with ammonia to form fatty acid amide, as indicated above. If, on the other hand, additional fatty acid is added, the water formed during the reaction of fatty acid with ammonia (see above) is used to split methyl fatty acid and thus to produce further fatty acid, which in turn is reacted with ammonia.
  • the simultaneous presence of methanol (or another corresponding lower alcohol) and ammonia is harmful because of the reaction
  • Fatty acid methyl ester + n-methylamide fatty acid methylamide + methanol.
  • Fatty acid + n-methylamide fatty acid-methylamide + water.
  • fatty acid amides can be produced in yields of 90 to 96% from the corresponding methyl or ethyl esters and ammonia, 0.8 to 5% of the fatty acid being added (book "Fatty Amides", by Arthur L. McKenna, edited by Humko Chemical Division and Witco Chemical Corporation, 1982, pages 12 to 14).
  • Typical reaction conditions are 10 to 18 hours at 150 ° C and 500 to 1000 psig, the equivalent of about 35 to 70 bar. This relatively high overpressure is disadvantageous in the technical production of fatty acid amides.
  • Powdered iron, lead and lead oxides, calcium nitrate, ethylene glycol and others are given as known catalysts. Further catalysts can be found in DE 20 26 832 C3.
  • fatty acid amides Another method for producing fatty acid amides is known from US Pat. No. 3,253,006.
  • fatty acid esters which are converted to fatty acid amides with ammonia in the presence of water.
  • the proportion of water is 50 to 200% by weight based on the amount of water required to saturate the equilibrium reaction mixture.
  • the reaction is carried out at temperatures from about 160 ° C. to about 290 ° C., that is to say at relatively high temperatures.
  • the converted reaction pressure is about 70 to 140 bar.
  • reaction mixture is typical of the prior art reaction processes. This can also be achieved by adding fatty acid, the fatty acid producing fatty acid amide and water by reaction with ammonia.
  • the invention is therefore based on the object of developing a process for producing fatty acid amides of the type mentioned at the outset, secondary and reverse reactions being largely avoided.
  • the crude product should contain practically no fatty acid and only very little nitrile.
  • the process should also be able to be carried out on a technical scale with considerably lower pressure and considerably shorter reaction times than in the prior art.
  • esters which are essentially free of water and fatty acids and using a compound of tetravalent tin which is soluble in the reaction mixture as the catalyst.
  • Fatty acid methyl ester + ammonia fatty acid amide + methanol, the methanol is continuously removed.
  • a fatty acid methyl ester other fatty acid alkyl esters, e.g. B. fatty acid ethyl ester, but fatty acid methyl ester has the advantage that the by-product methanol has a very low boiling point and can therefore be removed particularly easily from the reaction mixture, in particular by continuously or temporarily reducing the reaction pressure.
  • the catalyst used in the process according to the invention can be in solid or liquid form. It is only essential that this is a compound of tetravalent tin which is soluble, in particular organic, in the reaction mixture, that is to say in the fatty acid ester.
  • titanium catalyst typical of the production of fatty acid amide from free fatty acid e.g. B. "TYZOR LA” (trade name of Du Pont de Nemours)
  • TYZOR LA trade name of Du Pont de Nemours
  • reaction be carried out at a slight excess pressure. It is therefore proposed that the reaction be carried out at an excess pressure of at least 3 bar and in particular at an excess pressure of 3 to 6 bar. Even the low pressure of only 3 to 6 bar compared to the prior art leads to a significant further improvement in the economy of the process. It is also proposed that the reaction be carried out at temperatures of 140 to 200 ° C and in particular at temperatures of 150 to 180 ° C. The proposed reaction temperatures are therefore significantly lower than the values known from the prior art, whereby a further improvement in the economy of the process according to the invention is achieved.
  • the process according to the invention can be carried out batchwise or continuously, the latter variant being preferred.
  • the process be carried out batchwise and the pressure reduced from time to time to remove the lower alcohol formed during the reaction.
  • the reaction equilibrium shifts towards the desired fatty acid amides.
  • the undesirable formation of alkyl amide and water by reaction of the lower alcohol with ammonia is largely avoided.
  • liquid fatty acid ester together with the catalyst is passed in countercurrent to the gaseous ammonia within the reaction column.
  • the countercurrent procedure increases the yield and shortens the reaction time.
  • ammonia is circulated through the reactor, the lower alcohol being separated off before recycling.
  • dibutyltin oxide be used as the catalyst.
  • the reaction product contained no proportion of fatty acid at all.
  • Another particularly suitable catalyst is dibutyltin dilaurate.
  • the fatty acid ester contained therein and any fatty acid nitrile which may be formed be separated off from the reaction product, in particular by distillation.
  • the nitrile and fatty acid ester can be separated off overhead.
  • the catalyst is also separated off from the reaction product.
  • Figure 2 shows a plant for the continuous implementation of the method.
  • the percentages are percentages by weight.
  • Example 1 comparative example
  • TYZOR LA product from Du Pont de Nemours
  • Example 2 an experiment according to the invention was carried out with the catalyst "TEGOKAT 248" (product from Goldschmidt France) in solid form. It is amorphous dibutyltin oxide (C4 Hg ⁇ SnO.
  • FIG. 2 A corresponding system is shown as an example in FIG. 2.
  • the reaction takes place in a reaction column 7 built-in floors 8 under increased pressure.
  • Gaseous ammonia is fed in at the bottom of the column and fatty acid methyl ester is fed in at the top of the column together with the catalyst used according to the invention.
  • the liquid methyl ester with the catalyst dissolved therein flows down over the trays 8.
  • the gaseous ammonia flows from bottom to top and leaves the reaction area via a pressure reducing valve 9. From here on, work is carried out without overpressure or with only very slight overpressure.
  • the gaseous ammonia together with the likewise gaseous methanol is fed to the ammonia regeneration 10, where methanol is separated off and the cleaned ammonia gas is fed back into the reaction column 7 via a return line 11 and a compressor 12.
  • the liquid product is discharged via a further pressure reducing valve 13 to a separation device 14, in which the gaseous methanol and ammonia are separated off after the pressure reduction.
  • gases also end up in ammonia regeneration 10.
  • the crude product, which contains fatty acid methyl ester in addition to fatty acid amide is worked up by distillation, with methyl ester and nitrile being separated off overhead as a first step. If desired, the catalyst can also be separated off by crystallization in a solvent.
  • fatty acid methyl ester was converted into fatty acid amide in a reaction column with 17 trays.
  • the tallow acid methyl ester "Edenor METi 05" (product from Henkel KGaA) was used with a throughput of about 0.5 l / h.
  • "TEGOKAT 218" product from Goldschmidt France, namely a dibutyltin dilaurate (C4Hc)) Sn (OOC-R) 2 present in liquid form, was used as the catalyst.
  • the catalyst in Example 4 was the "TEGOKAT 248" already mentioned above. The other test conditions and the results are listed in Tables 3 and 4.
  • a temperature measuring device A temperature measuring device

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé de production d'amides d'acide gras à partir d'esters d'alkyle d'acide gras et d'ammoniac en présence d'un catalyseur. Selon ce procédé, on prend des esters sensiblement exempts d'eau et d'acide gras et on utilise comme catalyseur un composé d'étain tétravalent soluble dans le mélange réactionnel. Ce procédé fonctionne avec une faible pression, il se distingue par des temps de réaction courts et il est largement dépourvu de formation de sous-produits.
EP00974367A 1999-09-16 2000-09-07 Procede de production d'amides d'acide gras Withdrawn EP1212290A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19944418 1999-09-16
DE19944418A DE19944418A1 (de) 1999-09-16 1999-09-16 Verfahren zum Herstellen von Fettsäureamiden
PCT/EP2000/008724 WO2001019781A1 (fr) 1999-09-16 2000-09-07 Procede de production d'amides d'acide gras

Publications (1)

Publication Number Publication Date
EP1212290A1 true EP1212290A1 (fr) 2002-06-12

Family

ID=7922247

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00974367A Withdrawn EP1212290A1 (fr) 1999-09-16 2000-09-07 Procede de production d'amides d'acide gras

Country Status (5)

Country Link
EP (1) EP1212290A1 (fr)
JP (1) JP2003509402A (fr)
KR (1) KR20020029131A (fr)
DE (1) DE19944418A1 (fr)
WO (1) WO2001019781A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007011706A1 (de) * 2007-03-08 2008-09-11 Evonik Röhm Gmbh Verfahren zur Herstellung von Alpha-Hydroxycarbonsäuren
KR101554607B1 (ko) * 2008-11-07 2015-09-22 에스케이케미칼주식회사 지방산을 이용한 지방산알킬에스테르의 제조방법 및 장치
WO2015178633A1 (fr) * 2014-05-23 2015-11-26 페스웰 주식회사 Appareil de production de dérivé d'acide gras et appareil de recyclage de sous-produits
WO2024090435A1 (fr) * 2022-10-26 2024-05-02 住友化学株式会社 Composé phénolique, stabilisant, composition de matériau organique, procédé de stabilisation de matériau organique et procédé de production de composé phénolique
CN115974811A (zh) * 2023-01-10 2023-04-18 滕州市天水生物科技有限公司 一种2-异丙基-4-甲基噻唑的制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4277410A (en) * 1980-05-02 1981-07-07 Emery Industries, Inc. Process for the production of carboxylic amides using alkyltin catalysts
JPS62281848A (ja) * 1986-04-01 1987-12-07 Japan Tobacco Inc 酸アミドの合成法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0119781A1 *

Also Published As

Publication number Publication date
JP2003509402A (ja) 2003-03-11
KR20020029131A (ko) 2002-04-17
WO2001019781A1 (fr) 2001-03-22
DE19944418A1 (de) 2001-03-22

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