FR2656864A1 - Process for the preparation of an aliphatic or cycloaliphatic diamine, in particular for the preparation of diaminooctane - Google Patents

Process for the preparation of an aliphatic or cycloaliphatic diamine, in particular for the preparation of diaminooctane Download PDF

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Publication number
FR2656864A1
FR2656864A1 FR9000264A FR9000264A FR2656864A1 FR 2656864 A1 FR2656864 A1 FR 2656864A1 FR 9000264 A FR9000264 A FR 9000264A FR 9000264 A FR9000264 A FR 9000264A FR 2656864 A1 FR2656864 A1 FR 2656864A1
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France
Prior art keywords
dialdehyde
solvent
amination
ammonia
hydrogenation reaction
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.)
Pending
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FR9000264A
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French (fr)
Inventor
Grotenhuis Paulus Alexan Maria
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.)
Shell Internationale Research Maatschappij BV
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Shell Internationale Research Maatschappij BV
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.)
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Publication date
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Priority to FR9000264A priority Critical patent/FR2656864A1/en
Publication of FR2656864A1 publication Critical patent/FR2656864A1/en
Pending legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/09Diamines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/60Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes

Abstract

The invention relates to the preparation of an aliphatic or cycloaliphatic diamine having from 4 to 18 carbon atoms from the corresponding dialdehyde, which comprises an amination and hydrogenation reaction. An alcoholic solution of the dialdehyde is prepared, in order to convert the dialdehyde to the dihemiacetal and the dihemiacetal is subjected to the said amination and hydrogenation reaction. The invention applies especially to the preparation of octamethylenediamine. <IMAGE>

Description

 The present invention relates to the preparation of an aliphatic or cycloXphatic diamine having from 4 to 18 atoms, from the corresponding dialdehyde and applies, in particular, to the preparation of octamethylene diamine (or diaminooctane) from octane dial.

It is known to prepare a diamine from the corresponding dialdehyde by a two-step process comprising a first reactive step in which the dialdehyde is reacted with a monoamine at a temperature up to 100 "C to form the corresponding diazomethyne then a second step amination and hydrogenation in which the diazomethyne is reacted with ammonia and hydrogen, in the presence of a hydrogenation catalyst, at elevated temperature and pressure, to obtain the diamine (publication
US-A-4,215,073).

 The present invention aims to provide a method avoiding the first reactive step.

 According to the invention, the first step is not a reactive step but a simple dissolution of the dialdehyde in an alcohol, leading to the formation of a di-hemiacetal, which is then subjected to an amination reaction and d hydrogenation.

 Preferably, an alcohol is used whose number of carbon atoms is less than or equal to 10, in particular ethanol or pentanol.

 Preferably, at least 2 moles of alcohol are used per mole of dialdehyde.

 In a preferred embodiment of this process, the amination and hydrogenation reaction is carried out using gaseous ammonia, dissolved in a solvent, preferably a solvent which improves the diamine yield, which is the alcohol case; in this case, the solvent is preferably the same alcohol as that used for dissolving the dialdehyde.

 The amination and hydrogenation reaction is carried out at a temperature in the range 50-200 C, preferably close to 13rj "C and under a pressure in the range 5-100 bars, preferably close to rj bars, in a reactor into which the alcoholic solution of dialdehyde is introduced on the one hand and, on the other hand, a hydrogenation solvent, gaseous or dissolved ammonia, hydrogen and a hydrogenation catalyst.

 In a preferred embodiment, a reactor is filled with the solvent (preferably the same alcohol as that used for the dihemiacetal, and the hydrogenation catalyst is introduced. The gaseous ammonia is then introduced, which dissolves for a large part in then add the hydrogen and heat to 139 ° C. under 40 bars of total pressure.

We begin to introduce the alcoholic solution of the dialdehyde, maintaining the pressure by the supply of hydrogen.

 The hydrogenation catalyst advantageously consists of one or more elements from group VIII of the periodic table, in the form of a metal or an oxide, alone or on a support.

The single figure of the attached drawing is a diagram of implementation of the method
Example.
In a reactor containing ethanol, ammonia, hydrogen and a hydrogenation catalyst, (600 g of ethanol, 185 g NH3, 15 g of catalyst) at 1300C and under a total pressure of 40 bars, on the one hand, over 30 minutes, an ethanol solution containing 50% by weight of octanedial (89 g of octanedial per 89 g of ethanol) is introduced.

 The catalyst is Ni on silica containing 55% by weight of nickel (RCH 55/5 TS from Hoechst).

 The NH31groups aldehyde molar ratio is equal to 10.3.

 After 1 hour, from the end of the introduction of the alcoholic solution of dialdehyde, the reactor is cooled and depressurized, then the reaction mixture is filtered to remove the catalyst. The solvent is then removed by flash spray.

 The diaminooctane obtained is dissolved in a crystallization solvent (for example 100 g of toluene), the solution is kept for several hours (5 hours) at a temperature of -15 "C to -20 C and the precipitate is filtered, washed and Diaminooctane can also be purified by distillation (instead of crystallization).

 The selectivity for diaminooctane is 89 mol% and the purity of the product is 97%. The melting point of the crystals is 510. The crystals contain traces of Ni from the catalyst.

 The use, instead of gaseous ammonia, of an aqueous ammonia solution is possible but gives a less good selectivity.

 The hydrogenation catalyst may be a metal other than nickel, for example platinum or palladium on carbon.

 The invention is not limited to the preferred embodiment which has been described.

Claims (20)

1. Process for. Preparing an aliphatic or cycloaliphatic diamine having from 4 to 18 carbon atoms from the corresponding dialdehyde, which comprises an amination and hydrogenation reaction, characterized in that an alcoholic solution of the dialdehyde is prepared for transforming the dialdehyde into a di-hemi-acetal, and in that the di-hemi-acetal is subjected to said amination and hydrogenation reaction.
2. Method according to claim 1, characterized in that at least 2 moles of alcohol are used per mole of dialdehyde.
3. Method according to one of claims 1 and 2, characterized in that the alcohol is chosen from the group consisting of alcohols having a number of carbon atoms less than or equal to 10.
4. Method according to claim 3, characterized in that the alcohol used is ethanol or pentanol.
5. Method according to one of claims 1 to 4, characterized in that said reaction is carried out at a temperature of the range 50-200 "C, preferably close to 1 30 + C and under an absolute pressure of the range 5-100 bars, by introducing an alcoholic solution of dialdehyde into a reactor containing ammonia, hydrogen, a solvent and a catalyst.
6. Method according to claim 5, characterized in that a total pressure close to 40 bars is used.
7. Method according to one of claims 1 to 6, characterized in that for the amination is used NH3 in the form of ammonia solution in a solvent.
 8. Method according to claim 7, characterized in that an alcohol is used as the ammonia solvent.
9. Method according to claim 8, characterized in that an alcohol identical to that used for the solution of dialdehyde is used as the ammonia solvent.
10. Method according to one of claims 7 to 9, characterized in that one fills a reactor with the solvent for ammonia, the hydrogenation catalyst is introduced, the gaseous ammonia is introduced which dissolves for a large part in the solvent, the hydrogen is introduced, the mixture is heated and the alcoholic solution of the dialdehyde is gradually introduced while maintaining the pressure by supplying the hydrogen.
11. Method according to one of claims 1 to 10, characterized in that catalyzes the hydrogenation reaction by means of one or more elements from group VIII of the Periodic Table, in the form of metal or oxide, alone or on a support.
12. Method according to claim 11, characterized in that the catalyst used is Ni on silica.
13. Method according to claim 11, characterized in that the catalyst used is Pt or Pd on carbon.
14. Method according to one of claims 1 to 13, characterized in that after amination and hydrogenation reaction, NH3 and H2 which have not reacted are separated by cooling and depressurization.
15. Method according to one of claims I to 14, characterized in that after the amination and hydrogenation reaction, the catalyst is removed by filtration.
16. Method according to one of claims 1 to 15, characterized in that after the amination and hydrogenation reaction, the solvent is removed by flash vaporization.
17. Method according to one of the preceding claims, characterized in that the diamine obtained is crystallized.
18. Method according to one of claims 1 to 17 and substantially as described with reference to the example.
19. Application of a process according to one of claims 1 to 18 to the preparation of octamethylenediamine from octanedial.
20. The octamethylenediamine obtained by the implementation of a process according to one of claims 1 to 18.
FR9000264A 1990-01-11 1990-01-11 Process for the preparation of an aliphatic or cycloaliphatic diamine, in particular for the preparation of diaminooctane Pending FR2656864A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR9000264A FR2656864A1 (en) 1990-01-11 1990-01-11 Process for the preparation of an aliphatic or cycloaliphatic diamine, in particular for the preparation of diaminooctane

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR9000264A FR2656864A1 (en) 1990-01-11 1990-01-11 Process for the preparation of an aliphatic or cycloaliphatic diamine, in particular for the preparation of diaminooctane

Publications (1)

Publication Number Publication Date
FR2656864A1 true FR2656864A1 (en) 1991-07-12

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FR9000264A Pending FR2656864A1 (en) 1990-01-11 1990-01-11 Process for the preparation of an aliphatic or cycloaliphatic diamine, in particular for the preparation of diaminooctane

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008044655A1 (en) 2008-08-27 2010-03-04 Bayer Materialscience Ag Preparing di- or poly-amines from di- or poly-aldehydes, comprises dissolving aldehyde in a solvent and transforming reaction solution in presence of hydrogenation catalyst with ammonia and hydrogen in a trickle-bed reactor

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1248035B (en) * 1965-08-26 1967-08-24 Buna Chem Werke Veb A process for producing alpha-halo-beta-amino-vinyl-ketones
FR2328692A1 (en) * 1975-10-20 1977-05-20 Snia Viscosa Process for the preparation of alpha, omega-diamines aliphatic, and products obtained
EP0005856A2 (en) * 1978-06-03 1979-12-12 Ruhrchemie Aktiengesellschaft Process for the preparation of diamines
EP0088955A2 (en) * 1982-03-12 1983-09-21 Kuraray Co., Ltd. Process for producing 1,9-nonanedial
JPS58167547A (en) * 1982-03-29 1983-10-03 Kuraray Co Ltd Preparation of nonandiamine
JPS58201741A (en) * 1982-05-19 1983-11-24 Kuraray Co Ltd Separation method of alpha,omega-alkanedial

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1248035B (en) * 1965-08-26 1967-08-24 Buna Chem Werke Veb A process for producing alpha-halo-beta-amino-vinyl-ketones
FR2328692A1 (en) * 1975-10-20 1977-05-20 Snia Viscosa Process for the preparation of alpha, omega-diamines aliphatic, and products obtained
EP0005856A2 (en) * 1978-06-03 1979-12-12 Ruhrchemie Aktiengesellschaft Process for the preparation of diamines
EP0088955A2 (en) * 1982-03-12 1983-09-21 Kuraray Co., Ltd. Process for producing 1,9-nonanedial
JPS58167547A (en) * 1982-03-29 1983-10-03 Kuraray Co Ltd Preparation of nonandiamine
JPS58201741A (en) * 1982-05-19 1983-11-24 Kuraray Co Ltd Separation method of alpha,omega-alkanedial

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 7, no. 289 (C-202)(1434), 23 décembre 1983; & JP - A - 58167547 (KURARAY K.K.) 03.10.1983 *
PATENT ABSTRACTS OF JAPAN vol. 8, no. 41 (C-211)(1478), 22 février 1984; & JP - A - 58201741 (KURARAY K.K.) 24.11.1983 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008044655A1 (en) 2008-08-27 2010-03-04 Bayer Materialscience Ag Preparing di- or poly-amines from di- or poly-aldehydes, comprises dissolving aldehyde in a solvent and transforming reaction solution in presence of hydrogenation catalyst with ammonia and hydrogen in a trickle-bed reactor

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