The allocation method of the catalyst based on palladium

 

(57) Abstract:

The invention concerns a catalyst based on palladium from the environment, resulting from the reaction of hydroxycarbonate butadiene in partenavia acid. The invention consists in the method of allocating at least part of palladium dissolved in a solution also containing at least 3-pontenova acid, while the above solution is acidified and mixed with an aqueous solution of hydrochloric acid, get two liquid phases, of which the aqueous phase contains at least part of palladium. The technical result - the allocation of at least part of the palladium catalyst dissolved in the processing environment in the form of an ORGANOMETALLIC complex in order to be able to recycle this palladium catalyst in a new reaction hydroxycarbonylmethyl butadiene. 16 C.p. f-crystals, 2 tab.

The invention concerns a catalyst based on palladium from the environment in which it is dissolved.

More specifically, the invention concerns a catalyst based on palladium from the environment, resulting from the reaction of hydroxycarbonate butadiene to pentano the Asti palladium catalyst, dissolved in the processing environment in the form of an ORGANOMETALLIC complex in order to be able to recycle this palladium catalyst in a new reaction hydroxycarbonylmethyl butadiene.

The second method is the implementation of the allocation of at least part pentenoic acids present in the environment.

Hydroxycarbonylmethyl butadiene and/or its derivatives, such as, in particular, butanol allyl type, such as 3-butene-2-ol, 2-butene-1-ol, and mixtures thereof, addition products of hydrogen chloride to butadiene (chlorobutane), the main of which is Cotillard, can be carried out using water and carbon monoxide at a pressure above atmospheric pressure and in the presence of a palladium catalyst, soluble in the reaction medium.

You can refer to, for example, in European patent application 0648731, in which is given a more detailed description of this technique, although the present invention is not limited to the treatment of the reaction mixtures formed in the process according to this patent application.

In U.S. patent application 3857895 described by way of hydroformylation of olefin with what andom, containing at least one aminoalkyl or amidinophenoxy, or aminoaniline, or amidinophenoxy group associated with the trivalent atom of arsenic, antimony or phosphorus.

The mixture resulting from the reaction, is treated to separate product hydroformylation and the residue containing the catalyst, the above residue is treated with an acidic aqueous solution to dissolve the catalyst, and the resulting acidic solution is separated.

In this method, the ligand reacts with the acid, with the formation of ammonium salts, soluble in acid solution.

The reaction mixture used in the method according to the invention, contain more or less significant number of compounds involved in the reaction of hydroxycarbonate, and compounds resulting from the reaction.

In addition to the palladium catalyst, which may exist in different chemical forms, the reaction mixture formed contains partenavia acid, in particular 3-pontenova acid, water, hydrochloric acid, and common side reaction products, such as butenes or valeric acid, dicarboxylic acids such as adipic acid is ritel, which can be used in the reaction.

The invention relates, therefore, allocation method, at least part of palladium dissolved in a solution also containing at least 3-pontenova acid, which consists in the fact that the above-mentioned solution is acidified and mixed with an aqueous solution of hydrochloric acid to obtain two liquid phases, of which the aqueous phase contains at least part of palladium.

When the treated solution comes directly from the stage of hydroxycarbonate butadiene, before acidification, obviously, you have to reset the pressure of carbon monoxide.

Used hydrochloric acid usually contains 5 to 40 wt.% hydrochloric acid based on the weight of the solution.

Typically, a solution of hydrochloric acid added at the rate of 0.1 to 2-fold volume to the volume of the treated solution.

The formation of two liquid phases upon acidification can result from simply adding an aqueous solution of hydrochloric acid, depending on the composition of the treated solution.

Do so, in particular, but not exclusively, when the treated solution contains a solvent, mostly not smachivayasi, chlorinated aliphatic or chlorinated cycloaliphatic hydrocarbon.

The separation into two liquid phases can also be implemented by adding an organic solvent that is not miscible with water. This addition can be carried out after acidification, at the time of acidification or, if necessary, before acidification.

Presence is not miscible with water and organic solvent extraction allows to obtain at least part pentenoic acids present in the treated solution.

The temperature at which the processed acidified solution really is not critical to the method. So that you can work in the range 0 - 230oC (the temperature at which it can be held above reaction hydroxycarbonylmethyl). Almost the same work in the range of 20 - 200oC, preferably 40 to 110oC.

Acidification with hydrochloric acid allows you to turn palladium present in the treated solution in the form of an ORGANOMETALLIC complex compounds, in tetrachloropalladate acid (H2[PdCl4]). The temperature at which work affects the rate specified pre is no danger to cause precipitation of part of palladium.

The organic solvent used for extraction, chosen mainly from an aromatic, aliphatic or cycloaliphatic hydrocarbons, chlorinated aromatics, chlorinated aliphatic or chlorinated cycloaliphatic hydrocarbons, liquid under the operating conditions and, mainly, not miscible with water.

For convenience, use an organic solvent having a boiling point below the boiling point 3-pentenol acid.

As examples of these solvents, not limiting the scope of protection of the invention include benzene, toluene, xylenes, chlorobenzene, cyclohexane, butadiene, butenes, alkanes, such as hexane, heptane, octane, nonanes, decanes, undecane, dodecane and various mixtures of several of these solvents.

The mixture obtained after acidification of the treated solution, and, in some cases, after adding an organic solvent, and mixing, decanted at rest on the organic and aqueous phase.

As acidification, extraction with an organic solvent can be carried out at 0 - 230oC, more frequencies between 20 - 200oC and preferably 40 to 110o

The aqueous phase contains more than half the number of palladium, and a part of the dicarboxylic acids that may be present in the treated solution.

If desired, the extraction process using organic solvent can be repeated several times.

Depending on the organic solvent quantity pentenoic acids in the organic phase may exceed 60% and even 75% of the amount initially present in the processing solution. Partenavia acid, and more specifically 3-pontenova acid can then be isolated from the organic phase conventional chemical means.

The aqueous phase contains, typically, more than 60%, preferably more than 80% of palladium, initially present in the processing solution. Using the method according to the invention can recover in the aqueous phase, almost all the amount of palladium.

The aqueous phase containing palladium, mainly, can be recycled into a new reaction hydroxycarbonylmethyl butadiene. Usually, pre-evaporated part of the hydrochloric acid which it contains, thus, h is ATA such distillation solution of hydrochloric acid, the corresponding azeotropic mixture of water/hydrogen chloride. With continued implementation of the industrial method is most appropriate to use the resulting solution of hydrochloric acid for the implementation of acidification original solution, if necessary, after the introduction of the additional amount.

Variant of the method according to the invention is achieved by Stripping at least part pentenoic acids of the processed solution before implementation acidification.

Such a distillation is carried out at a temperature less than or equal to 110oC. This temperature limit is important because it has been observed that if you are at a higher temperature, part of the palladium precipitates. Such a deposition, even partial, is unacceptable for industrial way. In fact, it leads to the loss of very expensive metal and, in addition, seriously complicates the treatment of the reaction mixtures.

It turned out that if you work at a temperature of less than or equal to 110oC, more preferably at a temperature of less than or equal to 105oC, the deposition of palladium is not observed.

To be able to comply with this upper temperature limit, Ino pressure, below atmospheric, typically around 2 to 7 kPa.

With pentanoyl acid distills also lighter compounds that may be present in the processing solution, as, for example, butadiene, butenes, water, possibly part of the dicarboxylic acid and the solvent, if present.

The residue obtained after the distillation, contains palladium, as well as the most heavy compounds such as another part of the dicarboxylic acids. This residue is then treated, as described above, by using an aqueous solution of hydrochloric acid containing usually 5 to 40 wt.% hydrochloric acid based on the weight of the solution. In this case, it is not necessary to carry out the extraction with an organic solvent, as in the first embodiment that has been described.

As mentioned above, the temperature at which the acidifying the treated solution may be between 0oC and 230oC, almost between the 20oC and 200oC and preferably between 40oC and 110oC.

The acidified aqueous solution containing palladium, can be recycled into a new reaction hydroxycarbonylmethyl butadiene, as described above, if necessary, after distillation of the excess of hydrochloric acid.

In addition to the recycling of palladium catalyst in a homogeneous form and allocating at least part of the formed pentenoic acids, the method according to the invention allows to remove side products of the reaction of hydroxycarbonate butadiene, in particular, dicarboxylic acids, the accumulation of which could prove to be detrimental for the above reaction hydroxycarbonylmethyl butadiene.

The examples below illustrate the invention.

EXAMPLES 1-3

Into the flask under stirring with a magnetic stirrer consistently give: 67 mg PdCl2; 360 mg of 37% HCl; 8 g 3-pentenol acid (P3), 9 g of 2-methylglutaric acid; 3 g 2-adelantarnos acid.

Then add 20 ml of 10% aqueous HCl solution and 20 ml of organic solvent (specified in table 1, below). The flask contents are stirred at room temperature for 30 minutes By decanting divided into two phases and determine the amount of palladium in these two phases. In all cases, do not see the sediment. The results of the quantitative definitions are collected in table 1.

EXAMPLES 4-7

Into the flask under stirring magnetic IU the world acid and 3 g of 2-adelantarnos acid.

To obtain a homogeneous solution, the flask content was adjusted to 50oC, then return to the temperature ToC.

Then add 20 g of an aqueous solution of HCl (percent concentration (%) HCl are shown in table 2) and 20 g of toluene.

After mixing, the duration of which varies according to the examples, the two phases are separated by decantation. Palladium, as well as organic products, quantify in two phases.

The distribution coefficients of various products (mass relations factions water layer/organic layer) are summarized in table 2.

EXAMPLE 8

Repeat example 6, additionally passing through the mixture bubble for bubble 83 mmol of butadiene, during the extraction.

Get the following distribution coefficients: Pd = 36, P3= 0,13 of decollate = 0,9.

EXAMPLE 9

In a flask with a volume of 250 ml consistently load 1,668 g (9.4 mmol or 1 g Pd)PdCl2, 54,08 g of 37% aqueous HCl solution, 4,07 g 3-pentenol acid and H2O - a sufficient amount for 100 g of the solution

Distilled at atmospheric pressure to obtain about 70 ml of distillate (74,15 g). This distillate contains 3.2 g of 3-pentenol acid. Vapors have a temperature of 106-107oC and t

EXAMPLE 10

In odnogolosy flask 100 ml upload the reaction mixture resulting from the reaction of hydroxycarbonate butadiene in the presence of - -crotyl - palladium-chloride. This mixture has the following composition: 0,0707 g (0,357 mmol) krotil-palladium-chloride, 0,2706 g chlorobutane (or Cotillard), 8.0 g of 3-pentenol acid and 9.1 g of 2-methylglutaric acid and 3,11 2-adelantarnos acid.

To this reaction mixture was added 21 g of dichloroethane and 21 g of 20% aqueous hydrochloric acid solution.

The flask with a refrigerator placed in an oil bath.

Stand the mixture under stirring at 40oC for 1 h

After stopping stirring and decanting from each of the received two liquid phases take samples for the quantitative determination of palladium.

Again find that almost all of the palladium present in the original mixture.

The mass ratio distribution of the water layer/organic layer is equal to 32.

1. A way of separating at least part of the palladium from the solution coming after reaction hydroxycarbonylmethyl butadiene in partenavia acid containing at least 3-pontenova acid, characterized in that th is C, of which the aqueous phase contains at least part of palladium.

2. The method according to p. 1, characterized in that the aqueous solution of hydrochloric acid containing 5 to 40 wt.% hydrochloric acid based on the weight of the solution.

3. The method according to p. 1 or 2, characterized in that an aqueous solution of hydrochloric acid added at the rate of 0.1 to 2-fold volume to the volume of the treated solution.

4. The method according to PP.1 to 3, characterized in that the receipt of two liquid phases upon acidification is the result of simply adding an aqueous solution of hydrochloric acid.

5. The method according to p. 4, characterized in that the treated solution contains a solvent, generally not miscible with water, such as aromatic, aliphatic or cycloaliphatic hydrocarbons, chlorinated aromatics, chlorinated aliphatic or chlorinated cycloaliphatic hydrocarbon.

6. The method according to PP.1 to 3, characterized in that the receipt of two liquid phases occurs as a result of adding an organic solvent not miscible with water, after acidification, at the time of acidification or, if necessary, before acidification.

7. The method according to p. 6, characterized in that the organic races of alifaticheskih hydrocarbons, chlorinated aromatics, chlorinated aliphatic or chlorinated cycloaliphatic hydrocarbons, liquid under the operating conditions and generally not miscible with water.

8. The method according to p. 6 or 7, characterized in that the organic solvent is chosen among benzene, toluene, xylenes, chlorobenzene, cyclohexane, butadiene, butenes, alkanes, such as hexane, heptane, octane, nonanes, decanes, undecane, dodecane, and various mixtures of several of these solvents.

9. The method according to PP.1 to 8, characterized in that the two liquid phases after decanting represent the organic phase, containing more than half of the initial amount pentenoic acids, the major amount of butadiene and butenes, and a part of the dicarboxylic acids may be present in the treated solution, and the aqueous phase, containing more than half the number of palladium, and a part of the dicarboxylic acids may be present in the treated solution.

10. The method according to PP.1 to 9, characterized in that the aqueous phase containing palladium, recycle into a new reaction hydroxycarbonylmethyl butadiene preferably after the distillation part of the hydrochloric acid contained in the aqueous phases of the simulation.

11. The method according to p. 10, characterized in that the hydrochloric acid obtained by distillation and the corresponding azeotropic mixture of water/hydrogen chloride, is used for acidification original solution, if necessary after adding the additional amount.

12. The method according to PP. 1 - 11, characterized in that the treated solution before acidification with an aqueous solution of hydrochloric acid is distilled off at least part pentenoic acids.

13. The method according to p. 12, characterized in that the distillation is carried out at a temperature less than or equal to 110oC, more preferably at a temperature of less than or equal to 105oIn order to avoid deposition of palladium.

14. The method according to p. 12 or 13, characterized in that the distillation is carried out at atmospheric pressure or a pressure below atmospheric, in the range of 2 to 7 kPa.

15. The method according to PP. 12 to 14, characterized in that the residue obtained after the distillation, containing palladium, treated with an aqueous solution of hydrochloric acid.

16. The method according to p. 15, characterized in that the aqueous solution of hydrochloric acid containing 5 to 40 wt.% hydrochloric acid based on the weight of the distillation residue.

17. The way the share of hydroxycarbonate butadiene, if necessary, after distillation of the excess of hydrochloric acid.

 

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