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EP0000026A1 - Procédé de préparation d'amines secondaires - Google Patents

Procédé de préparation d'amines secondaires Download PDF

Info

Publication number
EP0000026A1
EP0000026A1 EP78100041A EP78100041A EP0000026A1 EP 0000026 A1 EP0000026 A1 EP 0000026A1 EP 78100041 A EP78100041 A EP 78100041A EP 78100041 A EP78100041 A EP 78100041A EP 0000026 A1 EP0000026 A1 EP 0000026A1
Authority
EP
European Patent Office
Prior art keywords
base
amines
primary
butylamine
ammonia
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
EP78100041A
Other languages
German (de)
English (en)
Inventor
Karl Dr. Merkel
Herbert Dr- Toussaint
Herbert Dr. Mueller
Herwig Dr. Hoffmann
Leopold Dr. Hupfer
Hans Jochen Dr. Mercker
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 SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP0000026A1 publication Critical patent/EP0000026A1/fr
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen

Definitions

  • secondary amines are preferably produced by reacting aldehydes with primary amines under hydrogenating conditions in the presence of a hydrogenation catalyst and a base, in particular NaOH or KOH.
  • the alkaline catalysts often form insoluble, soluble, solid to semi-solid products of unknown constitution with the amines. These substances lead to malfunctions, especially in the case of continuous (continuous) operation, since they are deposited in the lines and valves in the area of the hydrogenation reactors and also on the surface of the hydrogenation catalysts, so that their activity and thus the yield steadily decrease.
  • Quaternary ammonium bases by the general formula can be represented, the radicals R 1 to R 4 each being the same or different alkyl, cycloalkyl, aryl, aralkyl group, which in turn may contain functional groups, are generally well-known compounds. They can generally be obtained by completely alkylating ammonia or amines or ammonium salts with the known alkylating agents; if salts of the ammonium bases with acid anions are present, these can can be cleaved in a known manner to liberate the base. Obviously the choice of the substituents R 1 to R 2 is not decisive here; the radicals R 1 to R 4 can each have, for example, 1 to 20 carbon atoms.
  • Quaternary ammonium bases are obtained directly if ammonia or amines are reacted with alkylene oxides as alkylating agents, the mono-, di- and trialkanolamines being gradually formed and finally tetrahydroxyalkylammonium hydroxides being formed in the presence of a little water. Reaction products of ammonia with ethylene or propylene oxide are preferred.
  • the process of the invention can be carried out with the usual hydrogenation catalysts, e.g. at Houben-Weyl a.a.o. P. 602 are described.
  • These are e.g. Metals, such as palladium, platinum, iron, rhodium, rhenium, ruthenium or their compounds and mixtures in the form of finely divided suspensions or on supports for fixed bed catalysts; also molybdenum and tungsten catalysts and, with particular advantage, cobalt and nickel catalysts.
  • Cobalt and nickel catalysts can also be in unsupported form, i.e. applied as Raney cobalt or nickel or so-called sintered or unsupported catalysts or on supports.
  • They can contain admixtures of the above-mentioned metals or metal compounds and also iron, copper, manganese, chromium, molybdenum, silver and also alkali or alkaline earth metals or their compounds, further by aluminum, vanadium or boron or their oxygen compounds or by phosphoric acid be modified.
  • Aluminum oxides, silicates, pumice stone, clay, coal etc. can be used as carriers.
  • the method can be carried out continuously, but particularly advantageously, taking advantage of the advantages of the invention.
  • continuous (continuous) method it is practical to use vertical, pressure-resistant tubes which are filled with a fixed bed catalyst in the form of pills or strands.
  • the starting materials (aldehyde, amine, hydrogen) can be passed through the reactor from top to bottom (eg according to the trickle method), from bottom to top (bottom method) or in countercurrent.
  • Continuous operation is also possible with suspended catalysts, the sinking rate of the catalyst particles i is used by the reaction product.
  • the reaction is generally carried out at up to 500 bar, advantageously, carried out at 50 to 250 bar and at from 30 to 300 ° C, preferably at 70 to 130 ° C.
  • the base added according to the invention is discharged with the reaction mixture and can be recycled after the amines formed have been separated off.
  • Equipment Pressure autoclave made of steel with a capacity of 3,000 1, with a stirring shaft for homogenizing the reactants and conventional attachments and aids.
  • the reaction is carried out at a hydrogen pressure of 120 bar and a reaction temperature of 105 to 115 0 C for 6 hours.
  • the reaction mixture is filtered.
  • the water is separated from the filtrate by distillation.
  • the distillation residue (950 kg) consists of 95.5% methyl-n-butylamine.
  • dimethyl, monobutyl, Di-butyl-, di-butyl-methyl-amine and n-butanol found.
  • the crude yield of methyl-n-butyl-amine is 94.8% of the calculated.
  • the crude amine is purified by repeated distillation. 916 kg of methyl n-butylamine with a purity of 98.9% are obtained.
  • the crude amine is purified by repeated distillation. 775 kg of methyl n-butylamine with a purity of 98.0% are obtained.
  • n-butanol 2.7% n-butanol and a total of 2.5% other by-products (diethylamine, diethyl-n-butylamine, di-butylethylamine) and unknowns are found.
  • the same amount of ethyl-n-butylamine is obtained, and after 8 weeks of running 25.0 kg of crude ethyl-n-butylamine containing 92.9% ethyl-n-butylamine per hour.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP78100041A 1977-06-06 1978-06-01 Procédé de préparation d'amines secondaires Ceased EP0000026A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2725669 1977-06-06
DE19772725669 DE2725669C3 (de) 1977-06-06 1977-06-06 Verfahren zur Herstellung von sekundären Aminen

Publications (1)

Publication Number Publication Date
EP0000026A1 true EP0000026A1 (fr) 1978-12-20

Family

ID=6010961

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100041A Ceased EP0000026A1 (fr) 1977-06-06 1978-06-01 Procédé de préparation d'amines secondaires

Country Status (2)

Country Link
EP (1) EP0000026A1 (fr)
DE (1) DE2725669C3 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001064621A1 (fr) * 2000-03-02 2001-09-07 Bayer Aktiengesellschaft Procede de preparation d'amines par hydroaminomethylation d'olefines en presence de liquides ioniques

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10122758B4 (de) * 2001-05-11 2012-03-15 Oxea Gmbh Verfahren zur Herstellung von gemischten, sekundären Aminen

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1457608A (en) * 1974-09-17 1976-12-08 Ici Ltd Reduction process

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1457608A (en) * 1974-09-17 1976-12-08 Ici Ltd Reduction process

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001064621A1 (fr) * 2000-03-02 2001-09-07 Bayer Aktiengesellschaft Procede de preparation d'amines par hydroaminomethylation d'olefines en presence de liquides ioniques

Also Published As

Publication number Publication date
DE2725669B2 (de) 1979-04-05
DE2725669A1 (de) 1978-12-07
DE2725669C3 (de) 1979-11-22

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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Effective date: 19810626

RIN1 Information on inventor provided before grant (corrected)

Inventor name: MUELLER, HERBERT, DR.

Inventor name: TOUSSAINT, HERBERT, DR-

Inventor name: HOFFMANN, HERWIG, DR.

Inventor name: MERCKER, HANS JOCHEN, DR.

Inventor name: MERKEL, KARL, DR.

Inventor name: HUPFER, LEOPOLD, DR.