The method of producing chloroprene

 

(57) Abstract:

The chloroprene is produced by dehydrochlorination of 3,4-dichlorobutene-1 aqueous solution of alkali catalyst is a Quaternary ammonium compound, with separation of the product dehydrochlorinating on the organic phase, containing the chloroprene, and the catalyst, and the aqueous phase containing almost all by - product chloride salt, the organic phase is treated with oxicology, which interacts with the catalyst with the formation of a separate phase. The latter is separated from the organic phase containing the chloroprene, and the chloroprene contains significantly reduced the number of Quaternary ammonium catalyst. As the catalyst used connection in the molecule of which the nitrogen of the nitrogen is connected to four radicals by covalent bonds. Radicals are C6- C20-alkyl or alkenyl, aralkyl, one of the radicals represents alkyl, alkenyl or aralkyl having a hydroxyl or ether group in a-position relative to the nitrogen atom. The hydroxy acid is chosen from among inorganic acids, polymeric resins containing side groups of inorganic acids, and hydroxy acid soda phase, containing Quaternary ammonium compound and hydroxy acids. Interaction with oxicology carried out at 0 - 60oC, while the hydroxy acids used in the form of aqueous solutions and choose it from the group consisting of phosphoric, sulfuric, nitric, perchloric, chrome, coal, alkyl-, arylsulfonyl, molybdenum acid, selenium acid, sulfurous acid, tungstic acid, hypophosphorous, nitrogen and iodine acids, as oxyacids applied polymer resin containing side groups of the sulfonic acids or phosphinic acid. The number of added hydroxy acid is 2 to 10 equivalents. 1 EQ. Quaternary ammonium catalyst. Additionally return to loop through dehydrochlorinating at least some amount of Quaternary ammonium catalyst, selected from the stage of separation, or of the selected Quaternary ammonium catalyst is injected through dehydrochlorinating without separation from oxyacids. Handling oxicology get chloroprene with a significantly reduced content of the catalyst. 10 C.p. f-crystals, 4 Il., 3 table.

This application is a continuation of related applications N 07/858391 filed March 20, 1992

The invention from inania - removed from product raw processing oxicology.

The chloroprene (2-chlorobutadiene-1,3) is a valuable monomer used in the production of a wide range of synthetic elastomers. It is usually obtained by dehydrochlorination of 3,4-dichlorobutene-1 (vers) aqueous alkali, for example sodium hydroxide. In U.S. patent 3981937 (Campbell et. al.) describes a catalytic process dehydrochlorinated in the presence as catalyst of a Quaternary ammonium salt.

According to one variant of this method DWV, water and alkali and catalyst is introduced into one or more reaction vessels under stirring and interact at a moderate temperature (e.g. 50 - 70oC) as long, until almost complete dehydrochlorination vers. The stream exiting the reactor contains chloroprene, an excess of aqueous alkali, the salt formed during the reaction, the catalyst and various organic by-products. The chloroprene emit steam.

In U.S. patent 4605800 disclosed an improved method of producing chloroprene. The product from reactor dehydrochlorinating divided into phases and the organic phase is treated with steam at low temperature (below 80oC) to highlight chloroprene to treat acid, for example acetic or sulfuric, to neutralize residual alkali to steam treatment.

Although the use of Quaternary ammonium salts as catalysts results in high yields in the above process dehydrocorydaline, the use of these compounds is associated with some difficulties. For example, the presence of a catalyst causes corrosion of equipment used in the allocation of chloroprene from the organic phase. In addition, the presence of the catalyst in the organic phase leads to the entrainment of water and salt brine in this phase due to the surface-active properties of the catalyst.

This invention relates to a method of removing the catalyst from the product dehydrochlorinating that allows you to reduce the difficulties caused by the ash compounds and corrosion, and to achieve more efficient recycling of a relatively expensive catalyst. According to this invention features a method of producing chloroprene, which includes stages:

(a) dehydrochlorinating 3,4-dichlorobutene-1 interaction with aqueous alkali in the presence of organic Quaternary ammonium compounds as the catalyst, in the molecule of which the nitrogen is linked to the four radical or alkenyl or at least two radical represents a C7-C20-aralkyl, or (ii) at least one of the radicals represents aralkyl with attached C6-C20the alkyl or alkenyl, or (iii) at least one radical is an alkyl, alkenyl or aralkyl containing up to 20 carbon atoms and containing oxygraph or ether group in a-position to the nitrogen, and (iv) the remaining radicals are C1-C20-alkyl or-aralkyl, or C7-C20-aralkyl, in one or more reactors with obtaining raw product dehydrochlorinating and by-product salts of hydrochloric acid (chloride);

(b) the allocation of raw product dehydrochlorinating on aqueous and organic phases, the organic phase contains the chloroprene and the catalyst, and the aqueous phase contains almost all by - product chloride;

(c) contacting the organic phase at a temperature of from 0-60oC with at least 2 EQ. the equivalent of Quaternary ammonium catalyst, a hydroxy acid selected from the group comprising (i) an inorganic acid containing at least one oxygen atom attached to a hydrogen atom of the acid, and (ii) a polymeric resin containing side groups of inorganic ACS who formed a separate phase, containing Quaternary ammonium catalyst and hydroxy acids;

(d) separating the phase containing the Quaternary ammonium compound and the hydroxy acid from the organic phase containing the chloroprene, and

(e) allocation of chloroprene containing a significantly reduced amount of the catalyst.

Brief description of drawings

In Fig. 1 shows a diagram of receipt by a known method.

In Fig. 2 presents a diagram of the process according to this invention.

In Fig. 3 - schematic diagram of part of the method, representing a variant of the method, when the mixing and separation are carried out in a vessel with stirring and the decanter.

In Fig. 4 is a diagram of part of the process, representing a variant of the method, when the mixing and separation is performed by centrifugation.

Although the method according to this invention shown in figures using the same reactor, in fact it can be done using several reactors arranged in series, and the reagents and the catalyst can be filed, or in the same reactor or in different ways.

In Fig. 1 position 11 marked the reactor, in which dechlorination vers obtained is separated from the aqueous phase, containing salt brine and excess alkali. The organic phase line 17 is supplied to the Stripping column 19. Raw-chloroprene is removed from volatile components, which are condensed in the condenser 21, cooled in heat exchanger 23 and the partial phase in the decanter 25. Raw-chloroprene can then be purified, for example, by distillation (not shown). The rest of it columns 19, containing among other components, water, catalyst, high-boiling organic matter and a little bit of chloroprene, partially returned to the reactor 11 through line 27.

The method according to this invention is shown in Fig. 2. The reactor 29 and decanter 31 serve to hold dehydrochlorinating and separating the aqueous phase containing the salt brine and excess alkali, as before. However, treating the organic phase is completely different from the corresponding stage by a known method. The organic phase containing the Quaternary ammonium compound is applied to the installation of 33 for mixing and separation, where is added a separate phase oxyacids (item 35). As a result of this addition forms a separate phase containing the hydroxy acid and at least a certain amount (and often almost all) of the Quaternary ammonium catalyst is of opren), is separated and the remaining stream 37 chloroprene may be further purified, if desired, for example, by distillation (not shown). This invention, therefore, provides the removal of Quaternary ammonium catalyst by a simple method without Stripping and without the use of further materials cause corrosion of metal.

Education and the separation phase oxyacids and catalyst can be performed with known methods.

One method, shown in Fig. 3, the organic phase containing the catalyst, is introduced into the vessel 39 with the mixer on line 41. The hydroxy acid is added at line 42. The contents of the vessel are stirred in order to ensure close contact between the phase of the hydroxy acid and the organic phase, when a Quaternary ammonium catalyst passes into a phase of oxyacids. Mix on line 43 enters the decanter 45, where it is separated phase containing the hydroxy acid and the catalyst.

Another method of mixing and separation can be performed in a single device, for example, in a centrifuge 47, shown in Fig. 4. Raw the chloroprene stream 41 is fed to the centrifuge along with the flow of 42 phase oxyacids. Conical centrifuge rotates at high speed (for example, 4000 to 8000 rpm) and less dense pasalaysay to the second outlet opening. The time of contact and separation ranges from several seconds to several minutes. In addition, the separation can be carried out by electrostatic coalescence described in Kirk-Othmer Encyclopedia. 3 ed., vol. 1, pp. 673 - 693, or by using membranes and the like.

The degree of mixing required to create the desired contact between the organic phase and oxicology, depends to some extent on the desired level of removal of the catalyst. When production volume is enough to stir the mixture with a speed of 350 rpm for several minutes. In addition, you can apply a suitable static mixer. Often it is enough to expose the mixture to the impact energy from 15 to 109 j/s on m3(0,0772 - 0,553 horsepower per 1000 gallons US) of the organic phase for 1 to 15 minutes If the mixture is not sufficiently energetic part of the organic phase will not have contact with oxicology and extraction of the catalyst will be incomplete. Too much dilution can cause the formation of small, almost colloidal droplets, which will result in less efficient removal of the catalyst, and the selection will be long and difficult. Thus, in some cases, too much peremeci is but to use a wide range of temperatures. Preferably, this temperature does not exceed the boiling point of the organic phase under normal conditions. The use of relatively low temperatures also reduces the corrosive effect of Quaternary ammonium catalyst and oxyacids. Further, at low temperatures reduces the formation of dimers of chloroprene and polychloroprene.

The most desirable temperature range is 0-60oC, preferably 20-55oC.

As the Quaternary ammonium compounds used in the dehydrochlorination of 3,4-dichloroethene-1, you can use different connection types. The nitrogen may be substituted for four cyclic or acyclic organic groups, or may be part of the cycle. The Quaternary ammonium compound may contain one or more Quaternary ammonium groups. Nitrogen is associated with four groups of covalent bonds. At least one of the radicals may be C7-C20- alkyl or - alkenyl and at least two radicals can be C7-C20- Uralkalij. In addition, at least one organic radical can be an alkyl, alkenyl or aralkyl containing up to 20 carbon atoms and containing exigrep is the Quaternary ammonium compound, can be a C1-C20-alkyl or-alkenyl or C7-C20-aralkyl. Further, any two groups can be joined to form a ring containing nitrogen as part of the ring. Groups attached to the nitrogen atom, can be cyclic or acyclic, branched or unbranched, saturated or unsaturated. It is not essential that these radicals do not contain non-substituents.

However, any deputies all radicals must not contain functional groups capable of forming internal salts with Quaternary ammonium ion.

When a Quaternary nitrogen is part of a ring, this ring should not be aromatic, that is, the nitrogen must be connected to four aliphatic carbon simple communications. The ring may contain only atoms of carbon or other atoms of nitrogen or other elements, for example, oxygen atoms or sulfur. Usually rings contain 5-7 items. Can be used condensed cycles.

In General, the efficiency of the catalysts increases with increasing chain length of at least one substituent at the nitrogen. To increase the efficiency facilitated by the presence of hydroxyl not determinative. This may be a halogen ion, hydroxyine or any other anion that does not inhibit the reaction and does not contribute to the polymerization of chloroprene. The most commonly used ion chloride as chlorides are available and less expensive.

The preferred catalysts are: (a) compounds of General formula R1R2R3R4NCl, where R1, R2and R3-alkyl, alkenyl or aralkyl radicals containing up to 20 carbon atoms, and R4-alkyl or alkenyl containing 6-20 carbon atoms, or benzyl, substituted C6-C20-alkyl or-alkenyl, and (b) compounds of the above formula where at least one of R1, R2and R3contains a hydroxyl or ether group in a-position to the nitrogen atom. Typical examples of compounds of group (b) are compounds of the formula:

< / BR>
where

R1- benzyl, substituted C6-C20-alkyl;

R2- C1-C20-alkyl, or-alkenyl, or benzyl or benzyl substituted C1-C20-alkyl;

R3- H or methyl;

R4- H or methyl, the sum of X+Y = 2-15.

Particularly preferred Quaternary ammonium salts are.

(C12-C18SUB>Cl

(C12-C18-alkylbenzoic)N(CH2CH2OH)3Cl

(C12-C18-alkylbenzoic)N (CH2CH2OH)3Cl.

The number of Quaternary ammonium compounds used in the present method, ranges from 0.01 to 10% by weight of 3,4-dichloro-1-butene. If the connection is very active, you can apply to 0.01%. In total, more than 10% is not required and uneconomical.

As oxyacids you can apply any one of a number of inorganic acids containing at least one oxygen atom bound to a hydrogen acid groups. The term "inorganic" acid eliminates carboxylic acids, but includes carbonic acid and acid, which are based on other atoms in addition to carbon, but which, however, may contain organic substituents. Thus, suitable oxy acids are sulfuric and phosphoric. Other oxyacids include nitrogen, chlorine, chromium, coal acids, alkyl - and arylsulfonic acid, for example, p-toluensulfonate acid, molybdenum, selenium, sulfur, tungsten, hypophosphorous, nitrous acid and iodine acid.

Also suitable are polymers with side groups of inorganic doxycyclinea invention; hydrochloric acid, which is not oxicology, are also unsuitable.

Hydroxy acid must be in phase, which is virtually immiscible with the organic phase containing the Quaternary ammonium compound. For most of the above acids such phase is concentrated aqueous phase. However, in the case of polymers with side groups of inorganic oxyacids itself polymer phase is not miscible with the organic phase, so additional water component is not required.

Preferably in the implementation of the present invention to use a relatively concentrated solutions oxyacids. Large quantities of water are not necessary for carrying out the extraction and will lead to increased volumes and the loss of organic substances in aqueous phase. However, the selection can be performed using a low concentration of oxyacids - 22 wt.% and below. The upper limit of the concentration depends on the specific characteristics of the acid, in practice it is equal to 98%. Carbon dioxide, CO4included in the scope of this invention. For the purposes of the present invention is suitable carbonic acid, but at concentrations higher than 100%. This connection is especially suitable in the usual inorganic acids (except supercritical CO2) is 50-95%, and more preferably 65-85%. Particularly suitable sulfuric acid and concentrated phosphoric acid with a concentration of 65% and 85%, respectively.

The number of phase oxyacids should be sufficient for extraction of the desired quantity of the catalyst by the formation of a separate phase. Usually it is 200% or more of theoretical amount required to react with the ammonium salt. The use of such amount of acid, which is just enough to neutralize any small amount of substrate that can be carried out with an organic phase, without forming a separate phase catalyst/hydroxy acids, does not meet the purposes of this invention. Normally, the amount of acid required to allocate a significant amount of the catalyst from the organic phase, 10 times more than the quantity required to neutralize the sodium hydroxide present in the organic phase. Enough, at least 2 EQ. acid 1 EQ. of the catalyst. It is generally preferable ratio 2-10 EQ. acid 1 EQ. catalyst, most preferably a ratio of 3-5 EQ. acid 1 EQ. of the catalyst. Although it is possible to effectively apply large amounts of acid, it nekonome catalyst or to create a sufficient difference in densities for phase separation.

When using relatively dilute acids the total number of phase oxyacids will be more, and if you apply more concentrated acids, fewer. The use of large quantities of acid can help to overcome the inhibitory effect of sodium ion on the extraction process of the catalyst. Also, if you want the complete removal of the catalyst, it is possible to apply large quantities of acid (or repeat the extraction with smaller amounts of acid). Accordingly, the total number of hydroxy acid is usually 0.03 to 50% of the volume of the organic phase, preferably, 0.2 to 5%, more preferably 0.4 to 0.8%.

The concentration of catalyst in the organic phase is significantly reduced by the method according to this invention. Usually may be reduced by 90% or more. With this level of problems associated with the presence of a catalyst chloroprene, fall away. However, a more effective method is considered in the case of reducing the number of even 30%.

It was found that the presence of sodium ion inhibits the extraction of Quaternary ammonium salt oxicology. Therefore, to achieve maximum efficiency, you should remove almost all of the salt brine, images is gidrookisi sodium. In addition, the effect of excess sodium ions can be overcome by using higher concentrations of the catalyst.

Quaternary ammonium catalyst, selected during the processing oxicology, can be recycled to the stage of dehydrocorydaline.

Simple phase catalyst-hydroxy acid, is recycled through line 49 in Fig. 2 in the reactor 29. Part of the recycling can blow (item 51). Or the catalyst can be separated from oxyacids and one or both components separately to return in the cycle, for example, to the phase of the catalyst-hydroxy acid can be added a substance that causes the separation of components.

A suitable agent for this separation is the sodium ion in the form of sodium hydroxide or sodium chloride. Sodium ions then can be removed by ion exchange, if it is desirable to return in the acid cycle. In addition, the catalyst and the acid can be separated by adding ammonium hydroxide in phase catalyst-hydroxy acid. This addition causes the separation of Quaternary ammonium compounds from ammonium salts and the water formed by the reaction of ammonium hydroxide with oxicology.

Examples 1-14.

A series of experiments on the extraction is performed on the trail of the Rami and a tube for blowing nitrogen, download 350 or 500 ml, respectively, crude chloroprene, obtained by the interaction of 3,4-dichlorobutene-1 with aqueous alkali in the presence of a catalyst is a Quaternary ammonium chloride (bis-hydroxypropyltrimethylammonium chloride). The concentration of catalyst in the chloroprene equal 2000-8000 hours in a million. The temperature is controlled by circulating fluid in the jacket, heating the flask to 25-50oC. Add about 1-4.h. oxyacids per 1000 hours of raw-chloroprene and stirred the mixture at 350 rpm for 5 minutes Then stop stirring and leave the contents for 1 hour. Phase adduct catalyst-hydroxy acid precipitates. Chloroprene phase is removed and examined for the content of Quaternary ammonium compounds. The results are shown in table 1.

The results show that when processed by oxicology get chloroprene with a significantly reduced content of the catalyst. Removal of catalyst effective as phosphoric and sulphuric acids, the lowest concentration of 0.1 wt.%, the highest - 1.6 wt.%.

Example 15.

The extraction process is conducted as in example 1, but as oxyacids used p-toluensulfonate. The amount of acid solution is 3 ml per 1 l sieu salt catalyst. After stirring for 1 hour, leave the contents of the flask without stirring. The phases are separated slowly. After 1 hour, the content of catalyst in the chloroprene is 628 hours in a million.

Example 16.

The removal efficiency of the catalyst ion exchange resin is evaluated by processing raw chloroprene obtained by the dehydrochlorination of 3,4-dichlorobutene-1 aqueous alkali in the presence of bis-hydroxypropylmethacrylamide and containing 3369 hours per million of catalyst (free from sodium ion), different amounts of ion-exchange resin. In each of the 5 flasks add 300 ml of chloroprene and macroecology resin XN-1010TMcontaining a sulfonic group (Rohm and Haas) in the amount indicated in table 2. After 20 h at 24oC measure the amount of catalyst remaining in the organic phase. The results are shown in table 2, show that the ion-exchange resin effective to remove the catalyst.

Similar results are obtained at a temperature of 0 to 10oC, the amount of acid is 2,4-18,7 EQ. 1 EQ. ion-exchange resin.

Examples 17-23.

Various ion-exchange resins are examined by placing 100 ml of resin in a 15-centimeter (6-inch) column. The S="ptx2">

The chloroprene contains 2290 hours per million of catalyst. Table 3 shows the amount of residual catalyst in eluent.

Example 24.

Repeat example 13, but the amount of acid is 2.5%, because an excess of it is compensated by the presence of 100 PM per million of chloride of soda. The separation of the phases in the sample volume of 100 ml is carried out for 5 min in a centrifuge at 4000 rpm/min This treatment reduces the amount of catalyst in the chloroprene from 2200 hours per million to 117 hours per million, the efficiency is equal to 95%.

Example 25.

In a three-neck round bottom flask with a volume of 500 ml, equipped with a jacket, stirrer, thermometer and a tube for blowing nitrogen load 350 ml raw-chloroprene, obtained by the reaction of 3,4-dichlorobutene-1 with aqueous alkali in the presence of bis-hydroxypropylmethacrylamide. The concentration of catalyst in raw equal to 3000 hours in a million. The temperature control circulation of the liquid in the jacket, heating the flask to 25-50oC. In the flask add 0,14 ml of 70% nitric acid, which corresponds to 15.3 EQ. acid 1 EQ. catalyst, and stirred the mixture for 15 min at 25oC. Then stop stirring and leave the flask for one hour. Phase adduct catalyst-hydroxy acids OSA is.

1. The method of producing chloroprene by dehydrochlorination of 3,4-dichlorobutene-1 by interacting with the aqueous alkali solution in the presence of a catalyst is a Quaternary ammonium compound, in one or more reactors with obtaining the product of raw sugar and by-product chloride salt, followed

(a) separation of the product dehydrochlorinating on the organic phase, containing the chloroprene and the catalyst is a Quaternary ammonium compound, and the aqueous phase containing almost all by - product chloride salt,

(b) the implementation of the processing of the organic phase to produce the phase containing the catalyst is a Quaternary ammonium compound,

(c) separating the phase containing the Quaternary ammonium compound from the organic phase containing the chloroprene,

(d) the Department of chloroprene containing significantly reduced the number of Quaternary ammonium catalyst, characterized in that

as the catalyst is a Quaternary ammonium compound is applied to the connection in the molecule of which the nitrogen atom is connected to four radicals by covalent bonds, and at least one of the radicals represents (i) C6-C20-alkyl, or Aladin radical is aralkyl, containing C6-C20is an alkyl or alkanniny Deputy, or (iii) at least one radical is an alkyl, alkenyl or aralkyl containing up to 20 carbon atoms and having a hydroxyl or ether group in a-position relative to the nitrogen atom, and (iv) the remaining radicals are C1-C20-alkali or kalkanli or C7-C20-aralkyl, and at the stage (b) processing the organic phase is carried oxicology selected from the group comprising (i) an inorganic acid containing at least one oxygen atom, which is connected to the hydrogen atom, and (ii) a polymeric resin containing side groups of inorganic acids, and hydroxy acids injected into the organic phase at a temperature of ~ 0 - 60oC in the amount of at least 2 equivalents per equivalent of the Quaternary ammonium compound with the formation of a separate phase containing the Quaternary ammonium compound and the hydroxy acids, which is not mixed with the above organic phase.

2. The method according to p. 1, wherein the hydroxy acid is used in the form of aqueous solutions and choose it from the group consisting of phosphoric, sulfuric, nitric, perchloric, chrome, coal, alkyl - and array, nitrogen and iodine acids.

3. The method according to p. 1, characterized in that as oxyacids applied polymer resin containing group, sulfonic acids or phosphinic acids.

4. The method according to p. 1, characterized in that the hydroxy acid use acid selected from the group comprising sulfuric and phosphoric acid in aqueous solutions.

5. The method according to p. 4, characterized in that the hydroxy acids used in the form of an aqueous solution with a concentration of 22 to 98 wt.%.

6. The method according to p. 1, wherein the process is conducted with the introduction of the hydroxy acid in an amount of 2 to 10 equivalents. 1 EQ. Quaternary ammonium catalyst.

7. The method according to p. 4, wherein the process is conducted so that the amount of the hydroxy acid was 0.03 to 50% of the volume of the organic phase.

8. The method according to p. 1, characterized in that the interaction of the hydroxy acid with an organic phase is carried out at 0 - 60oC.

9. The method according to p. 1, wherein (e) further return to loop through dehydrochlorinating at least some amount of Quaternary ammonium catalyst, selected at the stage of separation.

10. The method according to p. 9, characterized in that meneley from oxyacids.

11. The method according to p. 9, characterized in that the Quaternary ammonium catalyst prior to the introduction on the stage of dehydrocorydaline separated from oxyacids.

Priority points:

20.03.92 - all signs of the way and radicals for Quaternary ammonium compounds (i) C12-C18-alkyl, (ii) C7-aralkylated, (iii) two radical represents C3is alkyl containing hydroxyl group in position relative to the nitrogen atom;

30.07.92 - (Ii) catalysts(C12-C18-alkyl) (benzyl)N(CH2CHOHCH3)2Cl, (C12-C18-alkyl) (benzyl)N(CH2CH2OH)2Cl, (C12-C18-alkylbenzoic)N(CH2CH2OH)3Cl; all other radicals for Quaternary ammonium compounds.

 

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