A method of obtaining a polyether-oximeter-oxy(oxo) -propyl-anhydride-succinic acid (peak)


(57) Abstract:

The invention relates to the production of PEAK that can be used as hardeners polymer compositions, varnishes, waxes, thickeners, reagents for the synthesis of surfactants, ion exchange polymers, flocculants water, floating agents, and so on PEAK produced by interaction of maleic anhydride and 4-methylene-1,3-dioxolane with excess maleic anhydride is not more than 1 mol.%, with the formation of an equimolar complex, with its subsequent copolymerization in the solid phase upon cooling the reaction mixture to (-4) - (+4)C. the Mixture was kept at this temperature, then heated above room temperature, but not above 802C, then cooled and heated, repeating the cycle at least 1 times subject to the time relationship of the cooling to the heating time in the range from 1 to 5, with subsequent distillation of the excess maleic anhydride when heated in vacuum. The invention improves the output PEAK and to reduce the number of volatile, flammable solvents. 3 table.

The invention relates to the chemistry of macromolecular compounds, namely the synthesis of new polyanhydrides with simple ether linkages in the polymer chain. Such is, emulsions, suspensions; chemical reagents for the synthesis of surfactants, Catino and/or anion-exchange polymers, flocculants water, floating agents, builders of the soil, the precipitating proteins from sera and drugs prolonged action.

A method of obtaining PEAK interaction of maleic anhydride (MAG) and 4-methylene-1,3-dioxolane (IOC) with the formation of an equimolar complex with subsequent copolymerization in the solid phase at room temperature, and then the selection after dissolving the reaction mixture in anhydrous acetone and precipitation of the desired product anhydrous diethyl ether (prototype) [Bagaev, S. I. , Stenina E. N. Vysokomol. Conn. B. 1998. So 40. N 11. C. 1876-1879. Russian Academy of Sciences, Moscow].

The disadvantages of this method are:

1. Non-quantitative output PEAK and the long duration of the process (prototype yield ~ 70% after 168 hours).

2. Increased pozharoopastnost allocation PEAK (Modules dissolution in acetone from 1:10 to 1:20; precipitation ether from 1:20 to 1:40).

It is also known that homopolymerization cyclic oxides and/or dioxolane in the solid phase - equilibrium process. Riesco falls speed homopolymerization due to the reduced rate of diffusion of monomers. To identify the main technical contradictions way copolymerization equimolar complexes MAGE IOC in the solid phase it is necessary to consider the following new, previously unknown, the experimental facts mentioned in paragraphs 1-4:

1. The formation of crystalline equimolar complex MAG IOC equilibrium process described by scheme:

< / BR>
where the ratio of the rate constants of forward and reverse reactions - complexation constant KarrK= KK1/KK-1which increases with decreasing temperature and decreases with its increase. This is confirmed by the fact that thermal effect of complexation of endothermic and equal to 30.5 0.5 kcal/mol and melting point of the crystalline equimolar complexes MAGE IOC (III) is in the range of 23-28oC.

2. When in the crystalline phase (III) of the active centers (thermodynamically compatible admixture!) the melting point of a new drug (III) is reduced. Themselves as active centers are formed from the product (III) complexes with charge transfer scheme:

< / BR>
This process is accompanied by a very weak exothermic effect.

3. The copolymerization reaction (additive recognize the improving temperature of the reaction mixture promotes the decomposition of the complexes (III) and in turn, the reduction of their concentration, which causes a reduction in the rate of copolymerization.

4. Additive accession complexes (III) to the active centres (IV) is accompanied by simultaneously flowing the isomerization product (II) disclosure of the double bond and oksolinovaja cycle. This process is in the presence of catalytic amounts of proton-donor additives according to the scheme:


Therefore, isomerization (II) in the product (V) excludes balance comonomers - PEAK that radically distinguishes this process from all previously known solid-phase processes homopolymerization. In the known processes the temperature rise of the reaction mixture shifts the equilibrium towards the monomer, causing depolymerization. Disequilibrium in copolymerization (III) makes it possible for PEAK with almost quantitative yield.

Therefore, the main technical contradiction method copolymerization of maleic anhydride and 4-methylene-1,3-dioxolane with high yield and short duration, in the solid phase, additive attach to each other crystalline equimolar complexes is a contradiction between the need to have a process temperature below which the temperature of the process above room temperature, providing accelerated diffusion of comonomers to the active centers of the growing chains.

The objective of the invention is to increase the output, reduce the duration of the process copolymerization equimolar complexes of maleic anhydride and 4-methylene-1,3-dioxolane in the solid phase with a simultaneous reduction in the number of volatile, flammable solvents.

The problem is solved in that the reaction mixture is prepared with an excess, but not more than one mole percent of maleic anhydride, when cooled below room temperature, kept at this temperature, then heated above room temperature, again cooled below room temperature, then heated above room temperature, repeating the cycle of cooling-heating at least once after the last cooling is distilled off in vacuum by heating excess maleic anhydride.

The essence is illustrated as set forth in paragraphs 1-4:

1. Cooling below room temperature during the preparation of the comonomers to the mixture and mixing (dissolving) causes rapid formation of crystalline complexes MAGE IOC and the transformation of these complexes in the act is active centers contribute to the formation of the copolymer PEAK in the solid phase, when the temperature of the cooling, but the emergence of the copolymer reduces the delivery rate of the crystalline complexes in the area of growth of the polymer chain. The rate of formation of the copolymer falls are "buried alive" macromolecule. According to the invention, the reaction mass is heated above room temperature, which leads first to the melting of crystalline complexes, and eventually to their decay into comonomers, in which the rate of diffusion is higher than the rate of diffusion of crystalline complexes.

Subsequent to the heating cooling below room temperature promotes the formation of crystalline complexes in the zone "buried alive" macromolecules and increase the molecular weight of the growing chains PEAK. While using crystalline complexes in the zone of the growth of polymer chains, the rate of formation of the copolymer is lowered again, and then again repeat the cycle of heating-cooling, causing the processes in the above-mentioned order.

Alternating cycles, cooling - heating, gradually reduces the amount not included in the copolymer of comonomers. The best way is to carry out reaction to 94-98% output PEAK. This is achieved 2-3 cycles. After the final KLH">

Since thermal effect of the formation of the crystalline complex and thermal effect their copolymerization almost equal to and opposite in sign, and the melting point of the crystalline complexes is in the range of 23-28oC when cooling is impractical to significantly reduce the temperature from the room. The most appropriate cooling to temperatures in the range from -4 to 4oC. At a lower temperature cooling deeper improve yield and reduce the duration is not observed, but rising energy costs. The upper limit of heating is limited by the boiling point of the most volatile of the co monomer and is 802oC.

2. In table. 1, the comparative characteristics of methods of obtaining PEAK prototype (experiments 9 and 10) and according to the invention (experiments 1-8).

As can be seen from comparing experiments 5 and 9, the output PEAK the proposed method 72% is achieved in 24 hours, while the output PEAK 70% of the prototype can only be achieved through 168 hours. Therefore, when 70% of the output of the proposed method is effective in 7 times.

From a comparison of experiments 2 and 10 show that the proposed method for a 49.5 hours is achieved yield 87%, at the same time (as in the prototype) 168 hours for the proposed method achieved output PEAK from 92 to 98%, what 22-28 % more than the prototype. From the comparison of experiments 1 to 8 between the ratio of cooling time to the time of heating can be seen that for the approximation to quantitative yield better at the beginning of the process to have more time cooling time heating, and at the final stage to the contrary.

In table. 2 shows the comparative performance of the methods of obtaining PEAK (experiments 11 and 12) of the proposed method and (experiments 13 and 14) of the prototype depending on the material of the reactor is a stainless steel NT and heat-resistant glass "Pyrex".

As can be seen from the data table. 2, the proposed method has the regulation to the passage of heat flow by applying more heat-conductive material of the reactor. Thus there is an even sharper increase in the yield of PEAK and reducing the duration of the process, while the choice of material of the reactor is not reflected on the output PEAK and duration of the process of the prototype.

In table. 3 shows the dependence of output PEAK on the number of redundantly entered maleic anhydride.

As can be seen from the data table. 3, the proposed method is most effectively realized when small, not more than 1.0% ASS="ptx2">

Almost quantitative yield is achieved for 5 hours, while the prototype to ensure a practically quantitative yield of the process copolymerization equimolar complexes MAGE IOC should be not less than 30 days.

Introduction in the reaction mixture an excess of the MAGICIAN simplifies the operation of allocating PEAK vacuum when heated, because stands out only one clean comonomer (the MAGICIAN ) is suitable for reuse. In addition, if the excess in the reaction mixture of 4-methylene-1,3-dioxolane reduced output PEAK due to the parallel running of homopolymerization 4-methylene-1,3-dioxolane under the same reaction centers cationic type.

3. Examples of carrying out copolymerization of maleic anhydride (MAG) and 4-methylene-1,3-dioxolane (IOC).

Experience 1. The MAGICIAN used a skill h and/or h D. A., but be sure before applying sublimated in vacuum at a residual pressure of 20 mm RT. Art. and temperature 52-55oC. the IOC after cleaning had characteristics that were specified in the prototype. A portion of the MAGICIAN was placed in a glass reactor, equipped with two cameras. One of them was loaded crystal MAGE, and in another liquid IOC. After cooling to a temperature of 4.THE MAGICIAN IOC+. Immediately after the dissolution of the MAGICIAN in the IOC and the mixture was bought a bright yellow color, then after the expiration of one hour of exposure at cooling increased viscosity and 24 hours reaction mass is hardened. After that, the reactor was heated for 12 hours, slowly raising temperature to 242oC, and then rapidly cooled to 4oC. Then the cycle of heating-cooling was repeated, and after the fourth cooling the reaction mixture had a brown color, and from her when heated drove at a residual pressure of 10 mm RT.article unreacted monomers. Selected PEAK were subjected to analyses. The product corresponded to the characteristics specified in the prototype. However, unlike the prototype had a higher characteristic viscosity of 7.4 DL/g instead of 3.0 DL/g of the prototype. Therefore when cooled to 4oC product is more high molecular weight. After the resultant deposition rates of acetone PEAK was a white powder, soluble in acetone, cyclohexanone, acetophenone, acetic anhydride and heated in water, in the latter case, after hydrolysis to PEAK.

Experiments 2-8 was carried out similarly to experiment 1, only differed conditions: maximum temperature is Denia-heating and the duration of heat treatment. Properties of products PEAK were identical to prototype and experiment 1, however, when cooled to a temperature of -4oC characteristic viscosity was a value of 4.5 DL/g, less than PEAK obtained when 4oC, but higher than PEAK obtained on the prototype.

Experiments 9 and 10 were carried out in full accordance with the instructions of the prototype.

Experience 11 was carried out similarly to experiment 1 in a glass reactor, but the duration was only 5 hours.

Experience 12 were carried out in a reactor made of stainless steel 1X18H9T, and conditions consistent with the experience of 11.

Experience 13 was performed on a prototype for 5 hours.

Experience 14 was similar to the experience of 13, but the material of the reactor was nerastarel.

Experiments 15-18 was similar to the experience of the 12, only when the excess maleic anhydride.

4. Polymers PEAK hydrolysis translated into plain polyester-oximeter-- hydroxy(oxo)propyl-succinic acid - PEAK.

For this purpose, finely chopped a portion of PEAK was mixed with distilled water at ratios from 1:200 to 1:220. The resulting suspension was heated to 802oC for 40 minutes with constant stirring until complete dissolution of polyanhydride. The floor is th water was removed by drying at a residual pressure of 10 mm RT.article and a temperature of 101oC for 4 hours. Received light yellow glassy, brittle product, d4200,81; soluble in water at room temperature after preswelling, while heating the sample at a speed of 5 deg/min the temperature of 50% weight loss at 220oC; characteristic viscosity of an aqueous solution at 20oC - 68,8 DL/g IR by a spectroscope shows that the samples PEAK contain strongly bound water in an amount up to 8%, it is in the monohydrate elementary level. The latter is confirmed by elemental analysis:

Found, %: C 43,83; 43,51; H 5,96; 5,35.

For C8H10O8H2O calculated, %: C 43,64; H the 5.45.

Received PEAK in the form of a monohydrate used:

4.1. To precipitate proteins from cheese whey.

Industrial tests were carried out at the Kirov dairy plant. In accordance with the test report from 30.03.99, testing the acid whey obtained on the cheese line A-OPT with a pH of 2.5 to 4.5, on the precipitation of proteins of 0.2% aqueous solution PEAK technologically efficient. No additional hardware for 10 minutes is deposited to 50 kg protein mass is in 1 tonne serum. Protein mass after centrifugation at one hundred the STI 18% increase to cottage cheese. Content PEAK serum was 0,004-0,001%.

4.2. To obtain the average sodium salt PEAK neutralization with a calculated amount of an aqueous solution of NaOH, and the average salt PEAK in the aqueous solution used in the production of cigarette paper. It was shown that the average salt PEAK with a concentration of 0.0004% improves quality cigarette paper by 5-10% for all indicators. The company "elikon" produced 5 tons of cigarette paper of high quality, it is shown that very high manufacturability using the average salt PEAK to stabilize the deposition of the chalk - filler, cigarette paper.

An important advantage of the proposed method to obtain PEAK is practically quantitative yield with very acceptable duration of the process, which on average 30-50 times lower than the duration of the prototype. This is achieved by cyclic temperature cooling-heating below room temperature and above room temperature. In conditions of mass production (and the unique properties of PEAK provide the necessity of its organization), each of 0.1%, or even 0.01% of output is crucial.

The second advantage of the proposed method is the scarfing high fire process of obtaining PEAK.

The third important advantage of the proposed method is used for copolymerization equimolar complexes MAGE IOC excess MAGE no more than 1% molar, which ensures a high concentration copolymerizate complexes (high speed process), the exclusion of incidental process homopolymerization 4-methylene-1,3-dioxolane and receiving at the end of the process, pure Mage, suitable for reuse. The latter says that if a continuous process even when receiving almost quantitative yield PEAK overdose to 1% molar of the Magician applies only to the initial loading of the reactor and in the future it return the product.

In addition, mass production of PEAK will allow you to organize production precipitator albumin protein from milk, cheese and/or cheese whey, which is equivalent to the increase in protein mass is equivalent proteins of chicken eggs in volume to 200 million per each region of Russia.

A very promising direction of use PEAK for the production of coated paper, high-strength papers, hardeners composite materials and as a highly active macromolecular reagent with various vedesu drug, modifying, protective, water-holding and other drugs.

A method of obtaining a polyether-oximeter--hydroxy(oxo)-propyl-anhydride-succinic acid by the interaction of maleic anhydride and 4-methylene-1,3-dioxolane with the formation of an equimolar complex with subsequent copolymerization in the solid phase, characterized in that maleic anhydride is used in excess, but not more than 1 mol.% in relation to the equimolar ratio, and the copolymerization process is carried out at cooling the reaction mixture to (-4) - (+4)oC, kept at this temperature, then heated above room temperature, but not above 80 2oC, then cooled and warmed in the modes described above, by repeating the cycle of cooling - heating at least once and keeping the ratio of cooling time to time of heating in the range from 1 to 5, with subsequent distillation after the last cooling excess of maleic anhydride, by heating in vacuum.


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