LU101281B1 - Process for the preparation of a fatty aldehyde - Google Patents
Process for the preparation of a fatty aldehyde Download PDFInfo
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- LU101281B1 LU101281B1 LU101281A LU101281A LU101281B1 LU 101281 B1 LU101281 B1 LU 101281B1 LU 101281 A LU101281 A LU 101281A LU 101281 A LU101281 A LU 101281A LU 101281 B1 LU101281 B1 LU 101281B1
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6409—Fatty acids
- C12P7/6418—Fatty acids by hydrolysis of fatty acid esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
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Abstract
The present invention relates to a process for the preparation of a fatty aldehyde which process comprises (a) providing a fatty acid, and (b) contacting the fatty acid with a zerovalent metal catalyst to reduce the fatty acid to the fat- ty aldehyde, wherein the zerovalent metal catalyst is in the form of solid particles.
Description
’ » 106784 _ 1 - LU101281 Process for the preparation of a fatty aldehyde The present invention relates to a process for the preparation of a fatty aldehyde, which process avoids the use of fossil resources and/or harsh reaction conditions, as well as the use of the obtained fatty aldehyde as e.g. a flavoring agent or fragrance.
There are currently two main methods for the synthesis of al- dehydes, in particular fatty aldehydes.
Short-chain fatty al- dehydes are usually prepared by hydroformylation.
The alkenes used as starting material in the hydroformylation reaction are typically obtained on the basis of crude oil.
In general, ra- ther high temperatures and very high pressures are applied in the hydroformylation reaction.
Long-chain fatty aldehydes are primarily obtained by dehydration of fatty alcohols.
Also this process is typically characterized by the use of fossil start- ing materials and rather harsh reaction conditions.
For instance, EP 37149 describes a method for the preparation of aldehydes by dehydrogenation of monovalent primary alcohols in the gas phase by means of a copper-containing catalyst.
For example, passing a gaseous mixture comprising octanol-i and hydrogen over a Cu/MgO catalyst for a period of four weeks at a temperature of 265 to 330°C results in an octanol conversion of 58%. The corresponding use of an Ag/Na,0 catalyst is de- scribed in SU 789491, and US 4,304,943 describes the conver- sion of alkyl and aryl hydroxy compounds to aldehydes in the presence of hydrogen using a MnO/NiO/MgO catalyst.
Furthermore, US 2,128,908 relates to a process for preparing short chain aliphatic aldehydes by oxidizing C3- and C4- alkanes.
For instance, a mixture of propane and butane is oxi- dized at 425 to 460°C to yield the desired aldehyde (20%) as EC des |
_ 2 - LU101281 well as formaldehyde (15%), methanol (19%) and carboxylic ac- ids (11%).
Alternative methods for the preparation of aldehydes, such as the extraction of aldehydes from natural products, are typi- cally characterized by a very low yield. For example, Palma et al. (J. Agric. Food Chem. 1999, 47, 5044) report on the super- critical fluid extraction of white grape seeds resulting in a an average yield of 10.6% for the first fraction which inter alia comprises aliphatic aldehydes in addition to fatty acids and sterols. Moreover, Chouchi et al. describe the desorption of bigarade peel oil from a polar adsorbent by supercritical CO, yielding a residue fraction comprising 0.22% of n-heptanal. Hence, there is still a need for a further process for the preparation of fatty aldehydes. In particular, it would be de- sirable to provide a process for the synthesis of fatty alde- hydes which process allows the use of renewable starting mate- rials and, thereby, reducing or avoiding the use of fossil re- sources. Moreover, the process should allow the use of mild reaction conditions so that rather high temperatures and/or pressures can be avoided. In addition, the fatty aldehyde should be obtainable with a high selectivity. It has surprisingly been found that the above problems are solved by the process defined below and in the appended claims. Accordingly, in a first aspect the present invention relates to a process for the preparation of a fatty aldehyde which comprises (a) providing a fatty acid, and
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(b) contacting the fatty acid with a zerovalent metal cata- lyst to reduce the fatty acid to the fatty aldehyde, wherein the zerovalent metal catalyst is in the form of solid particles. It has surprisingly been found that the contacting of a fatty acid with a solid zerovalent metal catalyst allows the synthe- sis of a fatty aldehyde with a high selectivity in a simple method without the use of excessive reaction temperatures or pressures. Moreover, the fatty acid used as starting material in the process according to the invention can suitably be pro- vided on the basis of natural, renewable resources. Thus, the use of fossil resources can be reduced or even avoided. The zerovalent metal catalyst is in the form of solid parti- cles, i.e. is a solid catalyst. It can be an unsupported (bulk) catalyst or can comprise a support material on or in which the zerovalent metal is present. Preferably, the zerovalent metal catalyst is a bulk catalyst, i.e. the cata- lyst is unsupported and essentially consists of or consists of the zerovalent metal. The oxidation state of the metal is ze- ro. Moreover, it is preferred that the solid particles of the zerovalent metal catalyst have a specific surface area of
0.0001 to 1080 m?/g, preferably 0.0003 to 1 m°/g, more prefera- bly 0.005 to 0.002 m°/g, even more preferably 0.001 to 0.01 m°/g. The specific surface area can suitably be determined by imaging procedures. In particular, the average particle size of the solid particles size 1s determined via microscopy and on the basis of this parameter the surface area of the parti- cles is calculated assuming a spherical shape of each parti- cle. It has been found that a zerovalent metal catalyst having such a specific surface area is particularly suitable for the
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Ca LU101281 efficient and selective conversion of fatty acids into fatty aldehydes.
It is also preferred that the solid particles have an average particle size of 70 nm to 3000 um, preferably 5 to 2500 um, such as 5 to 20 pm or 50 to 150 um or 500 to 2500 pm, as de- termined by imaging procedures, such as microscopy, resulting in a number-based average.
The metal of the zerovalent metal catalyst can suitably have a standard electrode potential of less than 1.40 V, preferably less than 1.20 V, more preferably less than 0.80 V. As used herein, the term “standard electrode potential” refers to the standard potential E° at a temperature of 25°C, a pressure of 1 atm and an effective ion concentration of 1 mol/L, with the metal in its zerovalent state as reductant and the metal cati- on in its monovalent (oxidation state = +1), divalent (oxida- tion state = +2) or trivalent (oxidation state = +3), prefera- bly the metal cation in its divalent form, as oxidant. The metal can be selected from the group consisting of Fe, Cu, Ag, Hg, Au, Pt and Sn and combinations thereof, and preferably is Fe or Cu or Ag and more preferably is Fe. In one embodiment the iron is present in the form of iron filings.
Without wishing to be bound to a particular theory, it is be- lieved that the higher the specific surface area of the cata- lyst is, the higher the tendency for formation of the corre- sponding alcohol instead of the desired aldehyde is. The for- mation of alcohol is probably due to the further reduction of the intermediate aldehyde. Thus, the specific surface area of the catalyst is believed to have an effect on the selectivity of the catalyst. Hence, catalysts having a rather high specif- ic surface area suitably comprise a more noble metal, such as silver. In contrast, catalysts having a rather low specific
Le LU101281 surface area suitably comprise a less noble metal, such as iron.
The fatty acid, which is provided in step (a) of the process according to the invention and which is to be reduced to the corresponding aldehyde, can typically comprise an aliphatic carboxylic acid having 1 to 32 carbon atoms, preferably 4 to 28, more preferably 6 to 18 carbon atoms. Moreover, the fatty acid can be saturated or unsaturated and can be branched or unbranched. Preferably, the fatty acid is unbranched. The selective reduction of the fatty acid to yield the corre- sponding aldehyde does generally not depend on the source of the fatty acid. Thus, synthetic fatty acids as well as fatty acids obtained from natural products or renewable starting ma- terials, like vegetable oils or other natural fatty acid es- ters, can be provided in step (a). Preferably, the fatty acid provided in step (a) is obtained from natural sources such as renewable starting materials. In particular, it is preferred that in step (a) the fatty acid is provided by (al) providing a fatty acid ester, and (a2) contacting the fatty acid ester with an enzymatic catalvst to hydrolize the fatty acid ester to the fatty acid. The enzymatic catalyst is suitably a hydrolase, preferably a hydrolase of subclass EC 3.1 such as subclass 3.1.1 like
3.1.1.1 and 3.1.1.3, more preferably an esterase like a li- pase, such as e.g. lipase B candida antarctica. Moreover, it is known that synthetic fatty esters, such as ethyl esters, on the one hand and natural fatty acid esters on the basis of triglyceride, such as vegetable oils, on the oth- er hand show a very similar hydrolization behavior. Hence, the
Ce LU101281 fatty acid ester provided in step (al) can be both a synthetic fatty acid ester or a natural fatty acid ester, such as a veg- etable oil. However, due the general demand for the use of natural starting materials, the fatty acid ester provided in step (al) is preferably natural fatty acid ester, such as a vegetable oil.
In step (b), the contacting is typically effected at a ratio of the zerovalent metal catalyst relative to the fatty acid of
8.0 - 10° to 3.1 - 107% m®? of catalyst per mmol of fatty acid, preferably 1.0 - 107 to 1.0 - 107° m® of catalyst per mmol of fatty acid, and more preferably 2.0 - 107* to 5.0 - 10™* n° of catalyst per mmol of fatty acid. It has been found that such a ratio of zerovalent metal catalyst to fatty acid is particu- larly suitable for the efficient and selective conversion of fatty acids into fatty aldehydes.
Moreover, it is preferred - with a view to avoid the undesired formation of the corresponding alcohols - that in step (b) the contacting is effected at a temperature of 80 to 800°C, pref- erably 80 to 250°C, more preferably 85 to 250°C, most prefera- bly 90 to 220°C, such as about 90°C or 180 to 220°C; and/or at a pressure of 100 to 1200 mbar, preferably 100 to 300 mbar or about 1000 mbar; and/or for a time of 3 to 180 min, preferably to 120 min, more preferably 20 to 90 min, most preferably to 70 min.
The reducing performance of the metal catalyst can be effected by other conditions as well. For example, the presence of oxy- gen or water can result in an undesired redox reaction between the metal catalyst and oxygen and/or water so that the amount of metal catalyst available for the reduction the fatty acid becomes too low. Hence, the contacting in step (b) is suitably effected at a concentration of water of less than 10 wt.-%, preferably less than 2 wt.-%, more preferably 0 to less than 1 wt.-%, relative to the total weight of the reaction mixture of step (b). Furthermore, the contacting in step (b) is suitably effected at a concentration of oxygen of less than 20 wt.-%, preferably less than 19 wt.-%, more preferably 0 to 1 wt.-%, such as 0 to 0.1 or 0 to 0.01 wt.-%, relative to the total weight of the reaction mixture of step (b).
In addition, the reduction in step (b) can be carried without the presence of hydrogen and it is preferred that the contact- ing in step (b) is effected at a concentration of hydrogen of about 0 wt.-%. The aldehyde obtained in step (b) preferably comprises 1 to 32 carbon atoms, and more preferably comprises hexanal, octanal, decanal, dodecanal or mixtures thereof. Such aldehydes are valuable products which can in particular be used as a flavor- ing agent, fragrance or as an intermediate product for the production of plastifiers, lubricating agents, polymers of pharmaceuticals. The invention disclosed herein is exemplified by the following examples which should not be construed to limit the scope of the disclosure. Examples Example 1: Preparation of dodecanal A mixture of 250 mL of ethyl dodecancat, 250 mL of water and 5g of Novozym 435 (a lipase B acrylic resin from candida ant- arctica) was stirred at 40°C for 24 hours. Then the mixture was cooled to 0°C for 8 hours. The liquid phase was separated by decantation. The container containing the solid phase com- prising dodecanoic acid was equipped with a heating unit and a distilling connecting tube which was held at 18°C. A pressure Ad
Ce LU101281 of 100 mbar was applied. The temperature of the distillation receiver and the gas phase of the distilling connecting unit was monitored and water was completely removed from the dodecanoic acid by distillation at a temperature of about 60°C.
Subsequently, 200 g of iron filings having a particle size of about 500 to 2500 pm and a specific surface area of about 14.7 cm?’/g were added to the dodecanoic acid. The system was rinsed with nitrogen three times and then a nitrogen pressure of 200 mbar was applied. The reaction mixture was heated to a temper- ature of 200 to 230°C for 35 min. Then the pressure was re- duced in intervals of 5 mbar to yield dodecanal in the distil- lation receiver which dodecanal was identified via gas chroma- tography using a PerkinElmer Clarus 500 apparatus equipped with flame ionization detector and a SUPELCO SLB-5ms capillary column having dimensions of 30 mm x 0.25 mm x 0.25 pm. Nitro- gen was used as mobile phase. For the detection of dodecanal, the temperature was kept at 60°C for 6 minutes and subsequent- ly raised to 200°C at a rate of 12°C/min. Then the temperature was kept at 200°C for 7 minutes.
Example 2: Preparation of hexanal 2 mL (16 mmol) of hexanoic acid were contacted at 90°C for 60 min with the following bulk catalysts A to D. The amount of the bulk catalysts is indicated in Table 1 below. The contact- ing was performed at ambient pressure under air atmosphere. Catalyst A: Iron particles (iron filings) having a particle size of about 500 to 2500 um and a specific surface area of about 14.7 cm?/g.
CL LU101281 Catalyst B: Iron particles (iron powder) having a particle size of about 90 pm and a specific surface area of about 8.44 - 10° cm®/g. Catalyst C: Iron particles (iron powder) having a particle size of about 70 nm and a specific surface area of about 1.08 - 107 cm?/g. Catalyst D: Copper particles having a particle size of about 9 um and a specific surface area of about 7.41 - 10° cm?/g.
The resulting reaction mixtures were subjected to a Fehling analysis. A blue color was indicative for the presence of al- dehydes, i.e. the formation of hexanal.
Table 1: [5 | 16 y HE a | 00 | €) s | ma | à o | 02 | 006 +/-: moderate blue Fehling analysis +: significant blue Fehling analysis ++: intensive blue Fehling analysis +++: very intensive blue Fehling analysis Some of the resulting reaction mixtures were also analyzed via gas chromatography using a PerkinElmer Clarus 500 apparatus
_ 10 - LU101281 equipped with flame ionization detector and a SUPELCO SLB-5ms capillary column having dimensions of 30 mm x 0.25 mm x 0.25 um. Nitrogen was used as mobile phase. For the detection of hexanal, the temperature was kept at 60°C for 6 minutes and subsequently raised to 210°C at a rate of 12°C/min. Then the temperature was kept at 210°C for 1.5 minutes. The reaction mixtures showed a peak at about 6.9 min indicative for hexanal with no peak at about 9.5 min which would be indicative for hexanol.
Example 3: Preparation of hexanal 3 mL (24 mmol) of hexanoic acid were contacted with 0.669 g of silver catalyst having a total surface of 1.27 cm’ and heated with a Bunsen burner for about 3 minutes. Subsequently, the reaction mixture was subjected to Fehling analysis which was positive indicating the presence of hexanal.
Claims (17)
1. Process for the preparation of a fatty aldehyde comprising (a) providing a fatty acid, and (b) contacting the fatty acid with a zerovalent metal catalyst to reduce the fatty acid to the fatty al- dehyde, wherein the zerovalent metal catalyst is in the form of solid particles.
2. Process according to claim 1, wherein the zerovalent metal catalyst is a bulk catalyst.
3. Process according to claim 1 or 2, wherein the solid par- ticles have a specific surface area of 0.0001 to 1080 m°/g, preferably 0.0003 to 1 m°/g, more preferably 0.005 to 0.002 m°/g, even more preferably 0.001 to 0.01 m°/g.
4. Process according to claims 1 to 3, wherein the solid par- ticles have an average particle size of 70 nm to 3000 um, preferably 5 to 2500 pm, such as 5 to 20 um or 50 to 150 pm or 500 to 2500 um.
5. Process according to any one of claims 1 to 4, wherein the metal of the =zerovalent metal catalyst has a standard electrode potential of less than 1.40 V, preferably less than 1.20 V, more preferably less than 0.80 V.
6. Process according to claim 5, wherein the metal is select- ed from the group consisting of Fe, Cu, Ag, Hg, Au, Pt and Sn and combinations thereof, and preferably is Fe or Cu and more preferably is Fe.
Fe Go
_ 12 - LU101281
7. Process according to any one of claims 1 to 6, wherein the fatty acid comprises an aliphatic carboxylic acid having 1 to 32 carbon atoms, preferably 4 to 28, more preferably 6 to 18 carbon atoms.
8. Process according to any one of claims 1 to 7, wherein the fatty acid is saturated or unsaturated and preferably is unbranched.
9. Process according to any one of claims 1 to 8, wherein in step (b) the contacting is effected at a ratio of the zerovalent metal catalyst relative to the fatty acid of
8.0 - 10° to 3.1 - 107” m’ of catalyst per mmol of fatty acid, preferably 1.0 - 107% to 1.0 - 107% m“ of catalyst per mmol of fatty acid, and more preferably 2.0 - 107% to
5.0 - 107% m® of catalyst per mmol of fatty acid.
10. Process according to any one of claims 1 to 9, wherein in step (b) the contacting is effected at a temperature of 80 to 800°C, preferably 80 to 250°C, more preferably 85 to 250°C, most preferably 90 to 220°C, such as about 90°C or 180 to 220°C; and/or at a pressure of 100 to 1200 mbar, preferably 100 to 300 mbar or about 1000 mbar; and/or for a time of 3 to 180 min, preferably 15 to 120 min, more | preferably 20 to 90 min, most preferably 30 to 70 min.
11. Process according to any one of claims 1 to 10, wherein in step (b) the contacting is effected at a concentration of water of less than 10 wt.-%, preferably less than 2 wt.-%, more preferably 0 to less than 1 wt.-%.
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; LU101281 | - 13 -
12. Process according to any one of claims 1 to 12, wherein in step (b) the contacting is effected at a concentration of oxygen of less than 20 wt.-%, preferably less than 19 wt.- %, more preferably 0 to 1 wt.-%, such as 0 to 0.1 or 0 to
0.01 wt.-%.
13. Process according to any one of claims 1 to 12, wherein in step (b) the contacting is effected at a concentration of hydrogen of about 0 wt.-%.
14. Process according to any one of claims 1 to 13, wherein in step (a) the fatty acid is provided by (al) providing a fatty acid ester, and (a2) contacting the fatty acid ester with an enzymatic catalyst to hydrolize the fatty acid ester to the fatty acid.
15. Process according to claim 14, wherein the enzymatic cata- lyst is a hydrolase, preferably a hydrolase of subclass EC
3.1 such as subclass 3.1.1 like 3.1.1.1 and 3.1.1.3, more preferably an esterase like a lipase, such as e.g. lipase B candida antarctica.
16. Process according to any one of claims 1 to 15, wherein the fatty aldehyde obtained in step (b) comprises 1 to 32 cafrbon atoms, and preferably comprises hexanal, octanal, decanal, dodecanal or mixtures thereof.
17. Use of a fatty aldehyde obtained by a process according to any one of claims 1 to 16 as a flavoring agent, fragrance or as an intermediate product for the production of plastifiers, lubricating agents, polymers of pharmaceuti- cals.
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Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU101281A LU101281B1 (en) | 2019-06-28 | 2019-06-28 | Process for the preparation of a fatty aldehyde |
| PCT/EP2020/067934 WO2020260523A1 (en) | 2019-06-28 | 2020-06-25 | Process for the preparation of a fatty aldehyde |
| EP20734048.0A EP3990424A1 (en) | 2019-06-28 | 2020-06-25 | Process for the preparation of a fatty aldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU101281A LU101281B1 (en) | 2019-06-28 | 2019-06-28 | Process for the preparation of a fatty aldehyde |
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| LU101281B1 true LU101281B1 (en) | 2020-12-28 |
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| LU101281A LU101281B1 (en) | 2019-06-28 | 2019-06-28 | Process for the preparation of a fatty aldehyde |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2128908A (en) | 1934-09-18 | 1938-09-06 | Celanese Corp | Preparation of oxygenated compounds |
| SU789491A1 (en) | 1978-07-05 | 1980-12-23 | Московский Ордена Трудового Красного Знамени Институт Тонкой Химической Технологии Им. М.В.Ломоносова | Method of preparing isovaleric aldehyde |
| EP0037149A1 (en) | 1980-03-29 | 1981-10-07 | Stamicarbon B.V. | Method for the preparation of aldehydes |
| US4304943A (en) | 1979-08-08 | 1981-12-08 | Phillips Petroleum Company | Conversion of alkyl and aryl hydroxy compounds producing aldehyde, alcohol and ketone using manganese oxide/nickel oxide/magnesium oxide catalysts |
| JPH11147846A (en) * | 1997-11-17 | 1999-06-02 | Mitsubishi Chemical Corp | Method for producing aldehydes and / or alcohols |
| WO2007086036A1 (en) * | 2006-01-30 | 2007-08-02 | The Procter & Gamble Company | Dryer-added fabric care articles |
-
2019
- 2019-06-28 LU LU101281A patent/LU101281B1/en active IP Right Grant
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2128908A (en) | 1934-09-18 | 1938-09-06 | Celanese Corp | Preparation of oxygenated compounds |
| SU789491A1 (en) | 1978-07-05 | 1980-12-23 | Московский Ордена Трудового Красного Знамени Институт Тонкой Химической Технологии Им. М.В.Ломоносова | Method of preparing isovaleric aldehyde |
| US4304943A (en) | 1979-08-08 | 1981-12-08 | Phillips Petroleum Company | Conversion of alkyl and aryl hydroxy compounds producing aldehyde, alcohol and ketone using manganese oxide/nickel oxide/magnesium oxide catalysts |
| EP0037149A1 (en) | 1980-03-29 | 1981-10-07 | Stamicarbon B.V. | Method for the preparation of aldehydes |
| JPH11147846A (en) * | 1997-11-17 | 1999-06-02 | Mitsubishi Chemical Corp | Method for producing aldehydes and / or alcohols |
| WO2007086036A1 (en) * | 2006-01-30 | 2007-08-02 | The Procter & Gamble Company | Dryer-added fabric care articles |
Non-Patent Citations (2)
| Title |
|---|
| PALMA ET AL., J. AGRIC. FOOD CHEM., vol. 47, 1999, pages 5044 |
| R. MALTHE: "Wirkung der fein zerteilten Metalle auf die Säuren der Methanreihe", CHEMIKER-ZEITUNG, vol. 28, 6 March 1909 (1909-03-06), pages 253, XP002797984 * |
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