CN102911024A - Method for preparing isononyl olefine aldehyde - Google Patents
Method for preparing isononyl olefine aldehyde Download PDFInfo
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- CN102911024A CN102911024A CN201210453864XA CN201210453864A CN102911024A CN 102911024 A CN102911024 A CN 102911024A CN 201210453864X A CN201210453864X A CN 201210453864XA CN 201210453864 A CN201210453864 A CN 201210453864A CN 102911024 A CN102911024 A CN 102911024A
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Abstract
The invention provides a method for preparing isononyl olefine aldehyde by cross condensation reaction between n-butanal and n-pentanal, between n-butanal and 2-methyl butyl aldehyde or between 2-methyl propionic aldehyde and n-pentanal in a mild condition; and the reaction condition is that the molar ratio of butyraldehyde to valeraldehyde is 1:5 to 5:1, the concentration of a sodium hydroxide or potassium hydroxide solution is 0.5-5.0 percent, the nitrogen or argon gas pressure is 0-0.5 MPa, the reaction temperature is 30-140 DEG C, and the reaction time is 1-10 hours. Isononyl olefine aldehyde prepared by the technology can produce isononyl alcohol when hydrogen is added.
Description
Technical field
The present invention relates to a kind of method for preparing different nonenal, belong to organic synthesis and organic catalysis field.
Background technology
The main purposes of different nonenal is to prepare isononyl alcohol by hydrogenation reaction, and isononyl alcohol is again the important source material of preparation diisononyl phthalate; Diisononyl phthalate is a kind of nontoxicity softening agent that adds in PVC produces, and has good thermotolerance, photostabilization, ageing-resistant and electrical insulating property, and volatility is very low, and the plasticising performance is good, is widely used in the production of electric wire, cable and plastics.
At present, the preparation method that isononyl alcohol is general is by following two steps: the first step is that octene and synthetic gas make isononyl aldehyde by hydroformylation reaction, second step is that the isononyl aldehyde Hydrogenation gets isononyl alcohol (Hong Zhongling, " deep processing of chemical industry organic raw material " P.16, Chemical Industry Press, 1977); Prepare the problem that there are two aspects in isononyl alcohol with the method, be subject to the restriction that octene feed is in short supply and price is high on the one hand, on the other hand, the difficulty of octene hydroformylation reaction is larger, and gordian technique is the employed catalyzer of hydroformylation reaction; What comprise for a long time that the long-chain olefin hydroformylation of octene uses is cobalt catalyst, and not only severe reaction conditions need to be carried out under the condition of 180 ℃ of temperature and synthetic gas pressure 7～8MPa, and catalytic reaction activity and poor selectivity; Improved research obtains certain progress to catalyzer in recent years, adopting rhodium-triphenylphosphine muriate such as the Mitsubishi chemistry is catalyzer, under 130 ℃ and 20MPa pressure, carry out the octene hydroformylation reaction and prepare isononyl aldehyde, then obtain isononyl alcohol (Takeru through hydrogenation, Onada, Chemtech, 1993 (4), 34); Bai Erzheng, contemporary petrochemical complex, 2002,10(10), 15); Liu Ye, He Dehua, Journal of Molecular Catalysis, 2000,14(3), 227; 2000; 14(5), having studied the reaction that several rhodiums-biphosphine ligand catalyst mixed octene hydroformylation generates isononyl aldehyde in 337 the paper, is 140 ℃ in temperature; under the condition of synthetic gas pressure 8.0MPa, the best result of reaction is mixed octene transformation efficiency 52.0%.
Isononyl alcohol also can be prepared by hydrogenation reaction by different nonenal; The preparation of olefine aldehydr compounds is generally taked aldehydes to carry out condensation reaction in the presence of alkali lye and is obtained; Used alkali lye is generally sodium hydroxide or potassium hydroxide aqueous solution, replace sodium hydroxide or potassium hydroxide aqueous solution although introduced use solid alkali magnesium oxide among Chinese patent CN 102070419 A, the reaction of catalysis n butyraldehyde aldolization, but butyraldehyde-n transformation efficiency and isooctene aldehyde yield are starkly lower than the result who uses sodium hydroxide or potassium hydroxide aqueous solution.
Same aldehyde can obtain the olefine aldehydr that carbonatoms doubles by self-condensation reaction in alkali lye; For example can prepare isooctene aldehyde by n butyraldehyde aldolization, the valeraldehyde condensation then can prepare the isodecyl olefine aldehydr, and they can obtain corresponding isooctyl alcohol and isodecyl alcohol behind shortening; Contain nine carbon atoms in the different nonenal molecule, can not be obtained from condensation by same aldehyde; But between butyraldehyde-n and valeraldehyde, butyraldehyde-n and 2 methyl butyraldehyde or 2 methyl propanal and the valeraldehyde, in the presence of alkali lye, cross-condensation can occur prepare different nonenal, have simultaneously in isooctene aldehyde and the isodecyl olefine aldehydr one or both olefine aldehydrs generate.
Summary of the invention
The objective of the invention is to seek the method that effectively preparation contains the different nonenal of nine carbon atoms by aldol reaction.
Technical scheme of the present invention is as raw material take butyraldehyde and valeral; wherein the mol ratio of butyraldehyde and valeral is 1:5-5:1; under alkali lye existence and protection of inert gas; temperature of reaction 30-140 ℃; gaseous tension is at 0-0.5MPa in the reaction process; reaction times 1-10 hour, prepare different nonenal through condensation reaction, can obtain the mixture of one or both olefine aldehydrs in isooctene aldehyde or the isodecyl olefine aldehydr simultaneously.
Butyraldehyde of the present invention and valeral are the mixtures of butyraldehyde-n and valeraldehyde, or the mixture of butyraldehyde-n and 2 methyl butyraldehyde, or the mixture of valeraldehyde and 2 methyl propanal.
Alkali lye of the present invention is sodium hydroxide or potassium hydroxide aqueous solution, and the mass percent concentration of alkali lye is between 0.5%-5.0%, and alkali lye and butyraldehyde and valeral volume of mixture compare at 5:1 between the 1:5.
Rare gas element of the present invention is nitrogen or argon gas.
Optimal reaction temperature of the present invention is 90-120 ℃, reaction times 2-6 hour.
Butyraldehyde of the present invention and valeral optimum mole ratio are 1:2.5-2.5:1.
The used butyraldehyde of the present invention and valeral with producing different nonenal isomer, are referred to as different nonenal when cross-condensation occurs.
1. reaction raw materials is butyraldehyde-n and valeraldehyde: two kinds of primary products of their cross-condensations are 2-propyl group-2-hexenoic aldehyde and 2-ethyl-2-heptenic aldehyde, and butyraldehyde-n and valeraldehyde separately condensation reaction products 2-ethyl-2-hexenoic aldehyde (hereinafter to be referred as isooctene aldehyde) and 2-propyl group-2-heptenic aldehyde (hereinafter to be referred as the isodecyl olefine aldehydr) are also arranged.
The reaction formula of cross-condensation (1) is as follows:
2. reaction raw materials is 2 methyl propanal and valeraldehyde: their cross-condensation reaction product mainly are 4-methyl-2-propyl-2-pentenals, and valeraldehyde self-condensation reaction product isodecyl olefine aldehydr is also arranged; Owing to sterically hindered reason, 2 methyl propanal is difficult for occuring self-condensation reaction.
The reaction formula of cross-condensation (2) is as follows:
3. reaction raw materials is butyraldehyde-n and 2 methyl butyraldehyde: their cross-condensation reaction product mainly are 4-methyl-2-ethyl-2-hexenoic aldehydes, and butyraldehyde-n self-condensation reaction product isooctene aldehyde is also arranged; Owing to sterically hindered reason, 2 methyl butyraldehyde is difficult for occuring self-condensation reaction.
The reaction formula of cross-condensation (3) is as follows:
Above-mentioned olefine aldehydr mixture, go out unreacted raw material aldehyde by fractionation by distillation after, obtain again the mixture of two or three alcohol in isooctyl alcohol, isononyl alcohol and the isodecyl alcohol through catalytic hydrogenation reaction; Through rectifying separation, can obtain isononyl alcohol again, simultaneously output isooctyl alcohol and isodecyl alcohol.
Condensation reaction under the normal pressure of the present invention is carried out in there-necked flask; In there-necked flask, load onto respectively spherical condensating tube, thermometer and inlet pipe; Butyraldehyde, valeral and alkali lye are added in the bottle; In device, pass into rare gas element by inlet pipe, behind the air in the displacement apparatus five times, be filled with again an amount of rare gas element, with the inert atmosphere in the holding device, there-necked flask is heated in the there-necked flask liquid return and keeps the backflow certain hour; Reaction is chilled to room temperature with reaction solution after finishing, and takes out reaction solution and leaves standstill phase-splitting, is for further processing lower floor's recycle of alkali liquor after the upper organic phase analysis.
Adding the condensation reaction of depressing carries out in autoclave; Butyraldehyde, valeral and alkali lye are added in the autoclave, check resistance to air loss after closing still, confirms air tight after, behind the air in the inert gas replacement still five times, pass into again rare gas element, the maintenance certain pressure; Stirring is warming up to specified temperature, and after reaction finished, cool to room temperature reduced pressure, opens still, took out reaction solution and left standstill phase-splitting, was for further processing lower floor's recycle of alkali liquor after the upper organic phase analysis.
Each composition of raw material and reaction product adopts gc analysis.
The invention effect
Compared with the prior art the present invention has following advantage and characteristics:
1. utilize industrial bulk product. butyraldehyde-n, valeraldehyde, 2 methyl propanal and 2 methyl butyraldehyde, take sodium hydroxide or potassium hydroxide aqueous solution as catalyzer, by the different nonenal of cross-condensation reaction preparation, prepare isononyl alcohol by hydrogenation reaction again, this is the route of a new production isononyl alcohol.
2. compare by the traditional method that hydroformylation reaction prepares isononyl aldehyde with octene, the octene price is higher, and the hydroformylation reaction condition is harsh, complicated operation; Reaction conditions of the present invention is gentle, and easy to operate, equipment is simple, only need bear lower pressure, and production prices are cheap.
Embodiment
Below by embodiment the present invention is carried out concrete description, be necessary to be pointed out that at this present embodiment only is used for the present invention is further specified, can not be interpreted as limiting the scope of the invention.
Embodiment 1
30ml butyraldehyde-n and valeraldehyde mixture, 2% aqueous sodium hydroxide solution 30ml are added in the autoclave, wherein butyraldehyde-n: valeraldehyde=1:1 mol ratio; Check resistance to air loss after closing still, confirm air tightly, behind the air in the nitrogen replacement still five times, pass into again nitrogen and be forced into 0.5MPa, stir and be warming up to 120 ℃ after, reacted 2 hours; Reaction is reduced pressure behind the cool to room temperature after finishing, and drives still, takes out reaction solution and places separating funnel, gets the upper organic phase analysis after phase-splitting, lower floor's recycle of alkali liquor; Contain unreacted butyraldehyde-n 0.5% in the reaction solution, valeraldehyde 0.2%, isooctene aldehyde 23.4%, different nonenal 43.1%, isodecyl olefine aldehydr 30.8%; Other component 2.0%.
Embodiment 2
In there-necked flask, load onto respectively spherical condensating tube, thermometer and inlet pipe; With 30ml butyraldehyde-n and valeraldehyde mixture, 2% aqueous sodium hydroxide solution 30ml adds in the there-necked flask, wherein butyraldehyde-n: valeraldehyde=1:5 mol ratio; In device, pass into nitrogen by inlet pipe, behind the air in the displacement apparatus five times, be filled with again an amount of nitrogen, with the inert atmosphere in the holding device; There-necked flask is placed on the oil bath pan; Be heated to 95～102 ℃, 5 hours reaction times; Reaction is chilled to room temperature with reaction solution after finishing, and takes out reaction solution, gets the upper organic phase analysis after phase-splitting, lower floor's recycle of alkali liquor; Contain butyraldehyde-n 0.4% in the reaction solution, valeraldehyde 0.3%, isooctene aldehyde 3.6%, different nonenal 22.4%, isodecyl olefine aldehydr 61.7%; Other component 11.6%.
Embodiment 3
In there-necked flask, load onto respectively spherical condensating tube, thermometer and inlet pipe; With 30ml butyraldehyde-n and valeraldehyde mixture, 2% aqueous sodium hydroxide solution 30ml adds in the there-necked flask, wherein butyraldehyde-n: valeraldehyde=5:1 mol ratio; In device, pass into nitrogen by inlet pipe, behind the air in the displacement apparatus five times, be filled with again an amount of nitrogen, with the inert atmosphere in the holding device; There-necked flask is placed on the oil bath pan; Be heated to 95～102 ℃, 6 hours reaction times; Reaction is chilled to room temperature with reaction solution after finishing, and takes out reaction solution, gets the upper organic phase analysis after phase-splitting, lower floor's recycle of alkali liquor; Contain butyraldehyde-n 0.4% in the reaction solution, valeraldehyde 0.3%, isooctene aldehyde 67.8%, different nonenal 23.2%, isodecyl olefine aldehydr 3.5%, other component 4.8%.
Embodiment 4
With 30ml butyraldehyde-n and valeraldehyde mixture, 1% aqueous sodium hydroxide solution 30ml adds in the autoclave, wherein butyraldehyde-n: valeraldehyde=1:0.8 mol ratio; Check resistance to air loss after closing still, confirm air tightly, behind the air in the nitrogen replacement still five times, pass into again nitrogen and be forced into 0.5MPa, stir and be warming up to 30 ℃ after, reacted 10 hours; After reaction finishes, reduce pressure behind the cool to room temperature, drive still, take out reaction solution, after phase-splitting, get the upper organic phase analysis, lower floor's recycle of alkali liquor; Contain butyraldehyde-n 8.7% in the reaction solution, valeraldehyde 24.6%, isooctene aldehyde 23.9%, different nonenal 23.4%, isodecyl olefine aldehydr 12.3%, other component 7.1%.
Embodiment 5
In there-necked flask, load onto respectively spherical condensating tube, thermometer and inlet pipe; With the mixture of 120ml butyraldehyde-n and 2 methyl butyraldehyde, 5% aqueous sodium hydroxide solution 120ml adds in the there-necked flask, wherein 2 methyl butyraldehyde: butyraldehyde-n=1:2.5 mol ratio; In device, pass into nitrogen by inlet pipe, behind the air in the displacement apparatus five times, be filled with again an amount of nitrogen, with the inert atmosphere in the holding device; There-necked flask is placed on the oil bath pan;
Be heated to 95～102 ℃, 6 hours reaction times; Reaction is chilled to room temperature with reaction solution after finishing, and takes out reaction solution, gets the upper organic phase analysis after phase-splitting, lower floor's recycle of alkali liquor; Contain butyraldehyde-n 0.1% in the reaction solution, 2 methyl butyraldehyde 4.5%, isooctene aldehyde 46.2%, different nonenal 44.7%, other component 4.5%.
Embodiment 6
In there-necked flask, load onto respectively spherical condensating tube, thermometer and inlet pipe; With the mixture of 60ml butyraldehyde-n and 2 methyl butyraldehyde, 2% aqueous sodium hydroxide solution 60ml adds in the there-necked flask, wherein 2 methyl butyraldehyde: butyraldehyde-n=1:1.5 mol ratio; In device, pass into nitrogen by inlet pipe, behind the air in the displacement apparatus five times, be filled with again an amount of nitrogen, with the inert atmosphere in the holding device; There-necked flask is placed on the oil bath pan; Be heated to 95～100 ℃, 5 hours reaction times; Reaction is chilled to room temperature with reaction solution after finishing, and takes out reaction solution, gets the upper organic phase analysis after phase-splitting, lower floor's recycle of alkali liquor; Contain butyraldehyde-n 0.2% in the reaction solution, 2 methyl butyraldehyde 15.9%, isooctene aldehyde 43.1%, different nonenal 36.5%, other component 4.3%.
Embodiment 7
In there-necked flask, load onto respectively spherical condensating tube, thermometer and inlet pipe; With the mixture of 120ml butyraldehyde-n and 2 methyl butyraldehyde,, 2% aqueous sodium hydroxide solution 120ml adds in the there-necked flask, wherein 2 methyl butyraldehyde: butyraldehyde-n=1:2.5 mol ratio; In device, pass into argon gas by inlet pipe, behind the air in the displacement apparatus five times, be filled with again an amount of argon gas, with the inert atmosphere in the holding device; There-necked flask is placed on the oil bath pan; Be heated to 95～100 ℃, 5 hours 20 minutes reaction times; Reaction is chilled to room temperature with reaction solution after finishing, and takes out reaction solution, gets the upper organic phase analysis after phase-splitting, lower floor's recycle of alkali liquor; Contain butyraldehyde-n 0.1% in the reaction solution, 2 methyl butyraldehyde 7.7%, isooctene aldehyde 52.4%, different nonenal 35.7%, other component 4.1%.
Embodiment 8
In there-necked flask, load onto respectively spherical condensating tube, thermometer and inlet pipe; With the mixture of 120ml butyraldehyde-n and 2 methyl butyraldehyde, 2% potassium hydroxide aqueous solution 80ml adds in the there-necked flask, wherein 2 methyl butyraldehyde: butyraldehyde-n=1:2.5 mol ratio; In device, pass into argon gas by inlet pipe, behind the air in the displacement apparatus five times, be filled with again an amount of argon gas, with the inert atmosphere in the holding device; There-necked flask is placed on the oil bath pan; Be heated to 95～102 ℃, 6 hours reaction times; Reaction is chilled to room temperature with reaction solution after finishing, and takes out reaction solution, gets the upper organic phase analysis after phase-splitting, lower floor's recycle of alkali liquor; Contain butyraldehyde-n 0.3% in the reaction solution, 2 methyl butyraldehyde 14.3%, isooctene aldehyde 56.3%, different nonenal 25.6%, other component 3.5%.
Embodiment 9
With 30ml2-methylpropanal and valeraldehyde mixture, 2% aqueous sodium hydroxide solution 20ml adds in the autoclave, wherein 2 methyl propanal: valeraldehyde=1:0.74 mol ratio; Check resistance to air loss after closing still, confirm air tightly, behind the air in the argon replaces still five times, pass into again argon pressurization to 0.4MPa, stir and be warming up to 120 ℃ after, reacted 2 hours; Reaction is reduced pressure behind the cool to room temperature after finishing, and drives still, takes out reaction solution, gets the upper organic phase analysis after phase-splitting, lower floor's recycle of alkali liquor; Contain 2 methyl propanal 17.5% in the reaction solution, valeraldehyde 0.9%, different nonenal 40.0%, isodecyl olefine aldehydr 20.8%, other component 20.8%.
Embodiment 10
In there-necked flask, load onto respectively spherical condensating tube, thermometer and inlet pipe; With the mixture of 100ml2-methylpropanal and valeraldehyde, 2% potassium hydroxide aqueous solution 70ml adds in the there-necked flask, wherein 2 methyl propanal: valeraldehyde=1:1.2 mol ratio; In device, pass into nitrogen by inlet pipe, behind the air in the displacement apparatus five times, be filled with again an amount of nitrogen, with the inert atmosphere in the holding device; There-necked flask is placed on the oil bath pan; Be heated to 90 ℃, 3 hours reaction times; Reaction is chilled to room temperature with reaction solution after finishing, and takes out reaction solution, gets the upper organic phase analysis after phase-splitting, lower floor's recycle of alkali liquor; Contain 2 methyl propanal 6.9% in the reaction solution, valeraldehyde 1.7%, different nonenal 35.7%, isodecyl olefine aldehydr 46.1%, other component 9.6%.
Embodiment 11
In there-necked flask, load onto respectively spherical condensating tube, thermometer and inlet pipe; With the mixture of 122ml2-methylpropanal and valeraldehyde, 1% aqueous sodium hydroxide solution 300ml adds in the there-necked flask, wherein 2 methyl propanal: valeraldehyde=1:1.4 mol ratio; In device, pass into nitrogen by inlet pipe, behind the air in the displacement apparatus five times, be filled with again an amount of nitrogen, with the inert atmosphere in the holding device; There-necked flask is placed on the oil bath pan; Be heated to 90 ℃, 5.5 hours reaction times; Reaction is chilled to room temperature with reaction solution after finishing, and takes out reaction solution, gets the upper organic phase analysis after phase-splitting, lower floor's recycle of alkali liquor; Contain 2 methyl propanal 10.2% in the reaction solution, valeraldehyde 0.7%, different nonenal 43.5%, isodecyl olefine aldehydr 39.0%, other component 6.6%.
Embodiment 12
In there-necked flask, load onto respectively spherical condensating tube, thermometer and inlet pipe; With the mixture of 122ml2-methylpropanal and valeraldehyde, 1% potassium hydroxide aqueous solution 150ml adds in the there-necked flask, wherein 2 methyl propanal: valeraldehyde=1:1.2 mol ratio; In device, pass into nitrogen by inlet pipe, behind the air in the displacement apparatus five times, be filled with again an amount of nitrogen, with the inert atmosphere in the holding device; There-necked flask is placed on the oil bath pan; Be heated to 90 ℃, 5.5 hours reaction times; Reaction is chilled to room temperature with reaction solution after finishing, and takes out reaction solution, gets the upper organic phase analysis after phase-splitting, lower floor's recycle of alkali liquor; Contain 2 methyl propanal 7.6% in the reaction solution, valeraldehyde 0.8%, different nonenal 39.2%, isodecyl olefine aldehydr 46.5%, other component 5.9%.
Above-described embodiment is summarized in the table 1.
Table 1 embodiment sums up
A; Be potassium hydroxide aqueous solution, all the other are aqueous sodium hydroxide solution.
Claims (6)
1. method for preparing different nonenal; it is characterized in that take butyraldehyde and valeral as raw material; wherein the mol ratio of butyraldehyde and valeral is 1:5-5:1; alkali lye exist and protection of inert gas under, in the reaction process gaseous tension at 0-0.5MPa, temperature of reaction 30-140 ℃; under reaction times 1-10 hour the condition, prepare different nonenal through condensation reaction, obtain simultaneously the mixture of one or both olefine aldehydrs in isooctene aldehyde, the isodecyl olefine aldehydr.
2. method claimed in claim 1 in accordance with regulations is characterized in that described butyraldehyde and valeral are the mixtures of butyraldehyde-n and valeraldehyde, or the mixture of butyraldehyde-n and 2 methyl butyraldehyde, or the mixture of 2 methyl propanal and valeraldehyde.
3. by method claimed in claim 1, it is characterized in that used alkali lye is sodium hydroxide or potassium hydroxide aqueous solution; The mass percent concentration of alkali lye is between 0.5%-5.0%, and alkali lye compares at 5:1-1:5 with butyraldehyde and valeral volume of mixture.
4. by method claimed in claim 1, it is characterized in that used rare gas element is nitrogen or argon gas.
5. by method claimed in claim 1, it is characterized in that temperature of reaction is 90-120 ℃, reaction times 2-6 hour.
6. by method claimed in claim 1, the mol ratio that it is characterized in that butyraldehyde and valeral is 1:2.5-2.5:1.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2852563A (en) * | 1955-10-17 | 1958-09-16 | Eastman Kodak Co | Condensation of isoaldehydes with lower aliphatic aldehydes |
| TW201237023A (en) * | 2011-03-03 | 2012-09-16 | Oxea Gmbh | Process for performance of polyphasic aldol condensation reactions to give mixed α, β-unsaturated aldehydes |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2852563A (en) * | 1955-10-17 | 1958-09-16 | Eastman Kodak Co | Condensation of isoaldehydes with lower aliphatic aldehydes |
| TW201237023A (en) * | 2011-03-03 | 2012-09-16 | Oxea Gmbh | Process for performance of polyphasic aldol condensation reactions to give mixed α, β-unsaturated aldehydes |
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Application publication date: 20130206 |