C5-hydrocarbons treatment process

FIELD: petrochemical processes.

SUBSTANCE: invention relates to treatment of C5-hydrocarbons in order to remove cyclopentadiene impurities, which process may be, in particular, used in rubber production industry when producing hydrocarbon monomers applicable in stereospecific polymerization processes. Treatment of hydrocarbons is accomplished with cyclohexane in presence of organic solvent and alkali catalyst, after which C5-hydrocarbons are separated from reaction products via rectification. Organic solvent is selected from alkylene glycol monoalkyl ethers including their mixtures taken in amounts 0.5 to 5.0 wt % based on C5-hydrocarbons.

EFFECT: increased degree of cyclopentadiene extraction at lower reagent consumption.

8 cl, 1 tbl, 23 ex

 

The invention relates to cleaning methods With5-hydrocarbon impurities cyclopentadiene (CPD) and can be used in the synthetic rubber industry, in particular in obtaining hydrocarbons (monomers)used in the processes stereoregular polymerization.

The cyclopentadiene from all those present in the monomer impurities is the most harmful for the process stereoregular polymerization in comprehensive ORGANOMETALLIC catalysts. The valid contents of the JRS, such as isoprene, set at the level of 0.0001 % wt.

Known methods of purification of monomers, such as isoprene, using as reagents for binding of cyclopentadiene podelochnyh aqueous solutions of hypochlorites of alkali metals, such as NaOCl (U.S. Patent No. 3538179, IPC707 With 7/148, publ. 1970), or copper chromite (Patent England No. 1125520, IPC707 With 7/148, publ. 1968).

The use of such reagents is not possible to achieve the required depth of purifying isoprene from JRS.

The known method of chemical purification of isoprene from cyclopentadiene and carbonyl compounds (Pasiecznik, Van, Limpopo. "Album of technological schemes of the main production of the synthetic rubber industry". L., Chemistry, 1986, page 51). Isoprene is mixed with cyclohexanone (CHN) and butyl alcohol is heated to 60° With, and then fed into the reactor, loaded with solid caustic potash. In the reactor in the presence of alkali cyclopentadiene interacts with cyclohexanone and partly with carbonyl compounds, resulting in the formation of fulvene. The reaction mixture is fed into a distillation column for distillation of isoprene from fulvenes and other high-boiling products formed during chemical cleaning, and cyclohexanone and butyl alcohol.

Closest to the present invention is a method of purifying isoprene from cyclopentadiene by treatment with cyclohexanone in the presence of an alkaline catalyst and solvent is n-butanol, followed by distillation of isoprene. The process is carried out at a temperature of 20-100°C, reaction time 1-3 hours when the content in the reaction mixture of cyclohexanone - 10 % of the mass. and butanol 5-10 % of the mass. (Shuvalov. "Isolation and purification of monomers for synthetic rubber. L., Chemistry, 1987, pp. 156-157).

The disadvantages of the above processes are the high consumption of cyclohexanone, in addition, butanol has a relatively low boiling point, which leads to unproductive his losses.

The objective of the invention is to develop purification methods With5-hydrocarbon impurities JRS, allowing to increase the depth of extraction JRC at lower reagent consumption.

The problem is solved by a method of cleaning With5-hydrocarbon impurities cyclopentadiene by treatment with cyclohexanone in the presence of an organic solvent and an alkaline catalyst, followed by separation With5-hydrocarbons from the reaction products by distillation, the organic solvent used monoalkyl esters of alkalophile or mixtures thereof in the amount of 0.5 to 5.0 wt%. in C5-hydrocarbons.

As the solvent used, for example, methyl ether of propylene glycol, methyl ether of dipropyleneglycol, ethyl ether of ethylene glycol, ethyl ether of diethylene glycol, butyl ether of diethylene glycol or CBM product of the manufacture of methyl ether of propylene glycol, which is a mixture of the methyl esters of propylene and dipropyleneglycol.

Using the proposed method can be cleaned, for example, those With5hydrocarbons like isoprene and piperylene.

The difference of the proposed technical solutions to the most similar is the fact that as an organic solvent used monoalkyl esters of alkalophile or mixtures thereof in the amount of 0.5 to 5.0 wt%. C5-hydrocarbons.

The proposed method allows to increase the degree of extraction JRC and homogenization of the catalyst, to reduce consumption, p is the agent - cyclohexanone and alkaline catalyst, which cannot be achieved by any similar method.

The method is as follows.

Charged to the reactor solid alkaline catalyst such as KOH, cyclohexanone and monoalkyl ether alkalophile or a mixture monoalkyl esters of alkalophile, in the amount of 0.5 to 5.0 wt%. (p5-hydrocarbons) and (C5-hydrocarbons, such as isoprene or piperylene. The cleaning process is carried out at constant stirring for 0.5-3 hours at a temperature of 40-60°S.5the hydrocarbons separated from the reaction products by distillation.

The implementation of the method illustrated by the following examples.

Example 1

Wipe piperylene from the JRC is as follows. In a round bottom flask, equipped with reflux condenser and electronically, load 10 g (10 % of the mass. per piperylene) solid KOH, 4 g (4 % of the mass. per piperylene) cyclohexanone, 10 g (10 % of the mass. per piperylene) butyl ether of diethylene glycol and 100 g of piperylene. Thermostatic the reaction mixture at a temperature of 40°C for 30 minutes with constant stirring. Piperidin separated from the reaction mass by distillation.

Purified piperylene photocolorimetric method to analyze the content of the JRS.

The results of the experiment are shown in the table.

The use of the 2

Purification of isoprene from JRC carried out as described in example 1.

The results of the experiment are shown in the table.

Example 3

Wipe piperylene carried out as described in example 1, the following components are loaded (per piperylene), % mass.: CON - 10, a mixture of butyl ether of diethylene glycol and the ethyl ether of ethylene glycol - 10, CHN - 2.

The results of the experiment are shown in the table.

Example 4

Wipe piperylene carried out as described in example 1, the following components are loaded (per piperylene), % mass.: CON - 5, a mixture of butyl ether of diethylene glycol and ethyl ether of diethylene glycol - 10, CHN - 2.

The results of the experiment are shown in the table.

Example 5

Wipe piperylene carried out as described in example 1, the following components are loaded (per piperylene), % mass.: CON - 5, a mixture of butyl ether of diethylene glycol and methyl ether of propylene glycol and 5 CHN - 2.

The results of the experiment are shown in the table.

Example 6

Wipe piperylene carried out as described in example 1, the following components are loaded (per piperylene), % mass.: CON - 5, a mixture of butyl ether of diethylene glycol and methyl ether dipropyleneglycol - 2, CHN - 2.

The results of the experiment are shown in the table.

Example 7

Wipe piperylene carried the t as well as described in example 1, the following components are loaded (per piperylene), % mass.: CON - 3, a mixture of ethyl esters of ethylene and diethylenglycol - 2, CHN - 2.

The results of the experiment are shown in the table.

Example 8

Wipe piperylene carried out as described in example 1, the following components are loaded (per piperylene), % mass.: CON - 3, butyl ether of diethylene glycol - 1, SGN - 2.

The results of the experiment are shown in the table.

Example 9

Wipe piperylene carried out as described in example 1, the following components are loaded (per piperylene), % mass.: CON - 5, butyl ether of diethylene glycol and 0.5, CGN - 4.

The results of the experiment are shown in the table.

Example 10

Wipe piperylene carried out as described in example 1, the following components are loaded (per piperylene), % mass.: CON - 3, ethyl ether of diethylene glycol - 2, CHN - 2.

The results of the experiment are shown in the table.

Example 11

Purification of isoprene carried out as described in example 1, the following components are loaded (isoprene), % mass.: CON - 3, ethyl ether of diethylene glycol - 2, CHN - 2.

The results of the experiment are shown in the table.

Example 12

Purification of isoprene carried out as described in example 1, the following components are loaded (isoprene), % wt is.: CON - 3, the ethyl ether of ethylene glycol - 2, CHN - 2.

The results of the experiment are shown in the table.

Example 13

Purification of isoprene carried out as described in example 1, the following components are loaded (isoprene), % mass.: CON - 3, methyl ester dipropyleneglycol - 2, CHN - 2.

The results of the experiment are shown in the table.

Example 14

Wipe piperylene carried out as described in example 1, the following components are loaded (per piperylene), % mass.: CON - 3, methyl ether of propylene glycol - 2, CHN - 2.

The results of the experiment are shown in the table.

Example 15

Wipe piperylene carried out as described in example 1, the following components are loaded (per piperylene), % mass.: CON - 3, CBM-product of the manufacture of methyl ether of propylene glycol, which is a mixture of the methyl esters of propylene and dipropyleneglycol - 2, CHN - 2.

The results of the experiment are shown in the table.

Example 16

Purification of isoprene carried out as described in example 1, the following components are loaded (isoprene), % mass.: CON - 3, CBM-product of the manufacture of methyl ether of propylene glycol, which is a mixture of the methyl esters of propylene and dipropyleneglycol - 2, CHN - 2.

The results of the experiment are shown in the table.

Example 17

Wipe piperylene PR the lead on pilot plant batch, consisting of a reactor, equipped with electronically and refrigerator type "pipe in pipe". Charged to the reactor solid alkali (KOH), cyclohexanone and butyl ether of diethylene glycol in amounts, respectively: 3, 2, and 2 % of the mass. (per piperylene) and piperylene. Close the lid of the reactor, the reactor is pressed. Cleaning is performed at a temperature of 40 °C for 30 minutes with constant stirring. Heating is performed by the supply of the heating fluid in the jacket of the reactor. Purified piperylene separated from the reaction mass by distillation.

The results of the experiment are shown in the table.

Example 18

Wipe piperylene carried out as described in example 1, the following components are loaded (per piperylene), % mass.: CON 10, butyl ether of diethylene glycol and 5 CHN - 4. Thermostatic the reaction mixture at a temperature of 20°C for 90 minutes with constant stirring.

The results of the experiment are shown in the table.

Example 19

Wipe piperylene carried out as described in example 1, the following components are loaded (per piperylene), % mass.: CON 10, butyl ether of diethylene glycol and 5 CHN - 4. Thermostatic the reaction mixture at a temperature of 30°C for 60 minutes with constant stirring.

The results of the experiment are shown in the table.

Example 20

Cleaning piperine the and carry out the same as described in example 1, the following components are loaded (per piperylene), % mass.: CON - 3, butyl ether of diethylene glycol - 2, CHN - 2. Thermostatic the reaction mixture at a temperature of 20°C for 90 minutes with constant stirring.

The results of the experiment are shown in the table.

Example 21

Wipe piperylene carried out as described in example 1, the following components are loaded (per piperylene), % mass.: CON - 3, butyl ether of diethylene glycol - 2, CHN - 2. Thermostatic the reaction mixture at a temperature of 30 °C for 60 minutes with constant stirring.

The results of the experiment are shown in the table.

Example 22

Purification of isoprene carried out as described in example 1, the following components are loaded (isoprene), % mass.: CON - 3, CBM-product of the manufacture of methyl ether of propylene glycol - 2, CHN - 2. Thermostatic the reaction mixture at a temperature of 20°C for 120 minutes under stirring.

The results of the experiment are shown in the table.

Example 23

Purification of isoprene carried out as described in example 1, the following components are loaded (isoprene), % mass.: CON -3, CBM product of the manufacture of methyl ether of propylene glycol - 2, CHN - 2. Thermostatic the reaction mixture at a temperature of 30°during the 15 minutes with constant stirring.

The results of the experiment are shown in the table.

As seen from the above examples, the use of the proposed method leads to an increase in the homogenization of the catalyst that allows you to selectively conduct a thin clearance5-hydrocarbon impurities JRS at any temperature, thus reducing the amount of expensive reagent (CGN) and alkaline catalyst (KOH).

Table
# exampleWith5-a carbohydrate-raceSolventThe content of component, % of the mass. (based on C5-hydrocarbon)The content of the JRC, % of the mass.
SolventCHNKONbefore cleaningafter cleaning
1PiperidinButyl ether of diethylene glycol104100,2UTS.
2IsopreneButyl ether of diethylene glycol104100,18UTS.
3PiperidinA mixture of butyl ether of diethylene glycol and the ethyl ether of ethylene glycol 102100,15UTS.
4PiperidinA mixture of butyl ether of diethylene glycol and ethyl ether of diethylene glycol1025ML0,00005
5PiperidinA mixture of butyl ether of diethylene glycol and methyl ether of propylene glycol5250,10,00005
6PiperidinA mixture of butyl ether of diethylene glycol and methyl ether dipropyleneglycol2250,150,00007
7PiperidinA mixture of ethyl esters of ethylene and di-etilenglikola2230,10,00009
8PiperidinButyl ether of diethylene glycol1230,10,0001
9PiperidinButyl ether of diethylene glycol0,5450,10,0001
10PiperidinEthyl ester of diety is angelicola 2230,150,00007

# exampleC5-hydrocarbonSolventThe content of component, % of the mass. (based on C5-hydrocarbon)The content of the JRC,% of the mass.
SolventCHNKONbefore cleaningafter cleaning
11IsopreneEthyl ether of diethylene glycol2230,18of 0.00006
12IsopreneEthyl ether of ethylene glycol2230,180,00007
13IsopreneMethyl ether of dipropyleneglycol2230,180,00007
14PiperidinMethyl ether of propylene glycol2230,250,00005
15PiperidinVAT product of the manufacture of methyl ether of propylene glycol2 230,2UTS.
16IsopreneVAT product of the manufacture of methyl ether of propylene glycol2230,18UTS.
17PiperidinButyl ether of diethylene glycol2230,2UTS.
18PiperidinButyl ether of diethylene glycol54100,2UTS.
19PiperidinButyl ether of diethylene glycol54100,15UTS.
20PiperidinButyl ether of diethylene glycol2230,20,00005
21PiperidinButyl ether of diethylene glycol2230,150,00007

# exampleWith5-hydrocarbonSolventContaining the s component, % mass. (based on C5-hydrocarbon)The content of the JRC, % of the mass.
SolventCHNKONbefore cleaningafter cleaning
22IsopreneVAT product of the manufacture of methyl ether of propylene glycol2230,230,00007
23IsopreneVAT product of the manufacture of methyl ether of propylene glycol2230,20,00009

1. Cleaning method With5-hydrocarbon impurities cyclopentadiene by treatment with cyclohexanone in the presence of an organic solvent and an alkaline catalyst, followed by separation of the C5-hydrocarbons from the reaction products by distillation, characterized in that the solvent used monoalkyl esters of alkalophile or mixtures thereof in the amount of 0.5-5.0 wt.% in C5-hydrocarbons.

2. Cleaning method With5-hydrocarbons according to claim 1, characterized in that the solvent used, the methyl ether of propylene glycol.

3. Cleaning method With5-hydrocarbons according to claim 1, characterized in that the solvent used methyl e is Il dipropyleneglycol.

4. Cleaning method With5-hydrocarbons according to claim 1, characterized in that the solvent used ethyl ether of ethylene glycol.

5. Cleaning method With5-hydrocarbons according to claim 1, characterized in that the solvent used ethyl ether of diethylene glycol.

6. Cleaning method With5-hydrocarbons according to claim 1, characterized in that the solvent used butyl ether of diethylene glycol.

7. Cleaning method With5-hydrocarbons according to claim 1, characterized in that the solvent used CBM product of the manufacture of methyl ether of propylene glycol, which is a mixture of the methyl esters of propylene and dipropyleneglycol.



 

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