前苏联专利SU1299501A3 Method for producing solutions of acrylamide or methacrylamide

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专利摘要:
The present invention relates to a process for producing acrylamide or methacrylamide utilizing microorganisms having a nitrilase activity. This process involves (1) utilizing highly active novel bacteria belonging to the genus Corynebacterium or the genus Nocardia, (2) conducting the reaction utilizing microorganisms having a nitrilase activity at temperatures as low as the freezing point of the medium to 15 DEG C. so as to conduct the reaction for a long period of time while maintaining a high concentration of acrylamide or methacrylamide, and (3) conducting the reaction according to a newly devised continuous column process to obtain a highly concentrated acrylamide or methacrylamide aqueous solution with economic advantages.
公开号:SU1299501A3
申请号:SU792745302
申请日:1979-03-28
公开日:1987-03-23
发明作者:Ватанабе Итиро；Сатох Есиаки；Такано Такаюки
申请人:Нитто Кемикал Индастри Ко.,Лтд (Фирма)；
IPC主号:

专利说明:

The invention relates to methods for producing amides, in particular, to an improved method for producing acrylic or methacrylamide using microorganism strains.
The aim of the invention is to simplify the process by using the proposed strains of microorganisms in the hydrolysis.
Example 1 „(comparative). 12.5 parts of washed cells of strain N-77 I (water content 80%) are obtained by aerobic cultivation using a culture medium (pH 7.2) containing,%: glucose 1; peptone 0,5j yeast extract 0.3; Malt extract 0.3, 6h. acrylonitrile and 81.5 parts of 0.05 M phosphate buffer (pH 8.8) are mixed and the reaction is carried out for 1 hour at 30 ° C with stirring. After completion of the reaction, the cells are removed by centrifugation to obtain a clear solution. This solution contains 8% acrylamide, but does not contain unreacted acrylonitrile and by-products such as acrylic acid. Thus, the reaction proceeds almost quantitatively until complete completion.
PRI me R 2 (comparative). 12.5 hours, washed cells of the strain N-771 (water content 80%), obtained analogously to example 1, are mixed with 87.5 parts of water and the acrylonitrile is continuously added dropwise to the mixture at a rate of 4 hours / 1 hour, while controlling the pH at a value of 8.0 using KANEA hydroxide with stirring, maintaining the reaction temperature at 30 ° C. After 2.5 hours, the addition of acrylonitrile is stopped, after which the mixture is stirred for 30 minutes. The resulting reaction solution is reacted for another 30 minutes, then centrifuged to remove the cells and obtain a clear solution. This solution contains 12, .0% acrylamide and does not contain unreacted acrylonitrile. Thus, the reaction is completely complete.
PRI me R 3. (comparative). 15 hours of washed cells of strain N-771 (water content 80%) obtained analogously to example 1, 8 h, methacrylonitrile and 77 parts of 0.05 M phosphate buffer (pH 8.8) are mixed and carried out for 1 .h reaction at 30 ° C. After completion of the reaction, the cells are removed
five
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0
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0
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by centrifugation to obtain a clear solution. This solution contains 10.2% methacrylamide. Although traces of methacrylic acid are detected, unreacted methacrylonitrile is not detected. Thus, the reaction proceeds almost quantitatively to completion.
PRI me R 4 (comparative). 12 hours of washed cells of strain N-774 (water content 75%), obtained analogously to example 1, are mixed with 88 parts of water, and methacrylonitrile is continuously dropped to the mixture at a rate of 3 parts / 1 hour, while controlling the pH of the solution at 8.5 with potassium hydroxide with stirring at 30 ° C. After reaction for 4 hours, the methacrylonitrile is dropped, and the stirring is continued for another 30 minutes until the methacrylate is almost completely reacted in the system. After completion of the reaction, the cells are removed by centrifugation to obtain a clear solution. The amount of methacrylamide in this solution according to
determination is 13%. I
PRI me R 5 (comparative).
25 hours of washed cells (water content 78%) of strain N-775, obtained by aerobic cultivation using a culture medium (pH 7.2), containing,%: glucose 1; peptone 0.5; yeast extract 0.3; malt extract 0.3; acetonitrile 0.1; 0.1; HgSO X 7 HgO 0.05, 5 parts of acrylonitrile and 70 parts of 0.05 M phosphate buffer (pH 8.8) are mixed and the reaction is carried out for 1 hour at 30 ° C with stirring. After completion of the reaction, the cells are removed by centrifugation to form a clear solution. This solution contains 6.7% aryl-amide, but does not contain unreacted acrylonitrile and by-products such as acrylic acid. Thus, the reaction proceeds almost quantitatively to completion.
Example 6. 8h. washed cells of strain N-771 (water content 75%) obtained by aerobic cultivation using a culture medium (pH 7.2) containing,%: glucose 1; peptone 0.5; yeast extract; 0.3; the malt extract is 0.3, mixed with 92 parts of water, and acrylonitrile is added dropwise to the mixture at a rate of 2 hours / 1 hour.
at the same time, the pH of the solution is controlled at a level of 8.0 by adding a 0.5 N aqueous KOH solution with stirring, at different reaction temperatures (0–30 ° C). Reaction pro; Continue until unreacted acrylonitrile is detected, and at this stage the reaction is interrupted, and the cells are removed.
(-) Z-O 5 10 15 20 30

sixteen
16 14
12
31.8 31.0 28.1 25.0 10.7 9.3
From the results of Table 1 it follows that the enzyme activity of the cells is stable, and the concentration of the obtained and accumulated acrylamide increases significantly when the reaction is carried out at a temperature not higher than 15 ° C.
An example. 13.5 hours washed cells of strain N-775 (water content 78%), obtained by cultivation according to formula 45 but Example 6, are mixed in 86.5 parts of water and acrylonitrile is added dropwise
by refluxing to obtain a clear solution. The content of acrylamide is determined in each of the solutions in order to compare the concentrations of accumulated acrylamide at the respective reaction temperatures.
The results of the experiments are presented in table.1.
Table 1
16 14
12
at a rate of 2 ppm / 1 h, while controlling the pH of the solution at the level of 8.0 by adding -0.5 of the N-aqueous solution of hydroxy sial potassium with stirring, at different reaction temperatures (0-30 ° C). Thereafter, the reaction is continued as in Example 6 until the determination of unreacted acrylonitrile. The concentration of acrylamide is determined in each of the solutions.
The results of the experiments are presented in table 2.
Table 2
The indicators for example 7
iiniiiiiiiiu

14 13 11 10 5 4
28.2 27.5 23.1 21.0 11 „5 9.5
From Table 2 it can be seen that the concentration of the obtained and accumulated acrylamide is significantly increased in those experiments in which the reaction is carried out at a temperature above 15 ° C.
Example 8. 4h. washed cells of strain N-771, obtained according to the example. 6, 0.45 parts of acrylamide, 0.05 parts of K, s-methylene-bis-acyramide and 4 parts of saline solution are mixed to obtain a homogeneous suspension. To the resulting suspension, 0.5 h of a 5% dimethylaminopropionitrile solution and 1 part of a 2.5% aqueous solution of potassium persulfate are added, and the resulting system is polymerized at 10-30 ° C. the cells containing the gel are punched into fine particles and washed with physiological saline to obtain 10 parts of immobilized cells. 72 parts of 0.05 M phosphate buffer (pH 8.0) are added to 20 parts of immobilized cells and Acrylonitrile is added dropwise at a rate of 2 hours / 1 hour, conducting the reaction at 15 ° C for 4 hours with stirring . The clear solution obtained by separating and removing bacterial cells from the reaction product contains 10.6% acrylamide and contains almost no by-products, such as acrylic acid, and the amount of unreacted acrylonitrile is determined. As a result, the reaction proceeds almost quantitatively until complete completion.
Example9. 5h washed N-77A cells (water content 80%), 30 each
35
25
Q 5 Q
radiated by azrobic growth in the culture medium (pH 7.2), containing,%: glucose 1; peptone 0.5; malt extract 0.3; yeast extract 0.3, over 48 hours, is added to 95 parts, 0.1. M phosphate buffer containing 2% acrylonitrile, adjusting the pH to 6.0, 7.0; 8.0 and 9.0 respectively. The reaction is carried out for 5 hours, gradually adding acrylonitrile so that the concentration of acrylonitrile does not exceed 2%. The concentration of acrylonitrile is measured by the appropriate: reaction solutions.
The results of the experiments are given in table.3.
pH
6.0 7.0 8.0 9.0
Example 10. 40 g of immobilized cells of strain N-771, obtained according to the method of example 9, are loaded into a column with a jacket, an inner diameter of 3 cm, length 25 cm) and a 4% aqueous solution of acrylonitrile
or a 2.6% aqueous solution of methacrylonitrile is continuously fed from the top of the column at a rate of 100 ml / h at 10 ° C and at 25 ° C (for comparison), with the reaction time given in Table 4. five
The ratios obtained: acrylamide or methacrylamide at the appropriate stages of the reaction are presented in table 4.
Table4
Example 11. Table 5 shows a comparison of the activity of whole cells and immobilized cells with respect to various microorganisms with acrylamide-producing ability.
Get immobilized cells as follows.
4 parts of whole cells (water content 75%), 0.45 parts of acrylamide, 0.05 parts of N, N-methyl-bis-acrylamide and 4 parts of physiological saline are mixed to form a homogeneous suspension. 0.5 h is added to this suspension. A 5% aqueous solution of dimethylaminopropionitrile and 1 part of a 2.5% aqueous solution of potassium persulfate. And the system is kept at 10–15 ° C for 30 minutes with the aim of polymerization. After this, the cells containing gels thus obtained are crushed and
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washed with saline to obtain 10 parts of immobilized cells.
The measurement of acrylamide-producing ability is as follows.
0.8 parts of whole cells or 2 parts of immobilized cells are diluted with 0.05 M phosphate buffer (pH 8.0) to a volume of 100 hours. Then 1 part of each of the solutions diluted in this way is mixed with 1 part 0, A 05 M phosphate buffer (pH 8.0) containing 2% acrylonitrile and after reaction at 10 ° C for 30 minutes with stirring, the acrylamide obtained in the reaction solution is determined to calculate the acrylanide production capacity of each sample of whole cells. and immobilized cells.
Table I
Strain N-771 type 30 Corynebacteriura
(FEPM-P No. 4445)
The strain N-774 species Corynebacterium 35 (FEPM-P No. 4446)
40
The strain N-775 type Nocardia (FEPM-P No. 4447)
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The amount of acrylamide, (g), obtained for 1 h of reaction, per 1 g of dry bacterial cells. Example 12. 40 parts of the washed cells of strain N-771 (water content 75%) obtained by aerobic cultivation using a culture medium (pH 7.2) containing,%: glucose 1; peptone 0.5; yeast extract 0.3; malt extract 0.3; 4.5 parts of acrylamide, 0.5 parts of N, N-methylene bis-acrylamide and 40 parts of saline are mixed to form a homogeneous suspension. To the resulting suspension, 5 parts of a 5% dimethylaminopropionitrile aqueous solution and 10 parts of a 2.5% aqueous solution of potassium persulfate are added and kept at 10 ° C for 30 minutes in order to polymerize. The massive cell containing the thus obtained gel was crushed into small particles and washed with physiological saline in order to obtain 100 ppm immobilized cells.
Five columns, equipped with jackets, with an inner diameter of 3 cm and a length of 25 cm, are loaded with 40 g of immobilized cells and are successively connected to each other and on top of column 1 are passed 4, aqueous jpacTBOp of acrylonitrile (using phosphate buffer, pH 8 , 0) at 10 C at a rate of 50 ml / h (about. Speed 0.5 h). After that, 100 parts of the eluate are mixed with 4.5 parts of acrylonitrile and passed to the syher through column 2 at a rate of 52.3 ml / h (volume velocity 0.53). The eluate obtained in a similar way is passed sequentially through column 3 at a rate of 54.5 ml / h (volume speed 0.54, column 4 at a rate of 56.8 ml / h (rev, speed 0.57) and through column 3 at a speed 59 ml / h (obs rate: 0.59 h) for 48 h. Thus, an eluate is continuously obtained with a reaction ratio of 100%. The concentration of acrylamide in this eluate is 25.5%.
At example 13. B7 of jacketed columns with a diameter of 3 cm and a length of 25 cm are loaded with 40 g of immobilized cells obtained according to example 12, and they are successively connected to each other and 2.5% aqueous solution of methacrylonitrile dissolved in the top of column 1 is passed through , 05 M phosphate buffer (pH 8.0), at a rate of 100 ml / h (about 1.0 hour), at 15 C. Then 100 parts of the eluate is mixed with 2.5 parts of methacrylate and this mixture is passed from top to bottom through column 2 at a speed of 103 ml / h (ob.speed is 1.03 h).
Then, the resulting eluate is similarly passed through column 3 with a co-movement speed down to 105 ml / h (v. Speed 1.05), column 4 at a rate of 108 ml / h (v. Speed 1.08), column 5 with a speed 110 ml / h (about 1.10), column 6 at a speed of 113 ml / h (about 1.13), column 7 with 115 ml / h (about 1.15) for 48 h The reaction ratio of this eluate is 100%, the concentration of methacrylamide in the eluate is 19.3%.
Example 14, 45 hours of washed cells of strain N-775 (water content 78%) obtained by aerobic cultivation using a culture medium containing,%: glucose 1; peptone 0,5j yeast extract 0.3; malt extract 0.3; acetonitrile 0.1; , 0.1; MgSO X 7 0.05, 4.5 h, acrylamide, 0.5 h, N, N -methylene bis-acrylamide and 40 h, saline are mixed to form a homogeneous suspension. To the resulting mixture was added 5 parts of a 5% aqueous solution of dimethylaminopropionitrile and 10 parts of a 2.5% aqueous solution of potassium persulfate and held for 30 minutes at room temperature. The massive glue-containing gels thus obtained were crushed into small particles and washed with saline to obtain 100 parts of immobilized cells,
Such immobilized cells are loaded into a sectional column having several sections, each of which has a volume of 100 ml and contains 40 g of immobilized cells, 2.5% methacrylonitrile solution (using 0.05 M phosphate buffer pH 8.0 ) continuously fed at a rate of 100 ml / h on top of the uppermost section, while maintaining the temperature inside the column at 15 ° C, and methacrylonitrile at a rate of 3 ml / h is added on top of each section 2-7 for 48 hours to carry out the reaction, B In this case, the eluate from the bottom of the 7th column section was not detected ivaut, meta-krylonitrila. Thus, the reaction was 100%. The methacrylamide content in this eluate was 19.3%.
Example 15 Two casing-equipped columns having an inner diameter of 3 cm and a length of 25 cm, each of which is filled with 40 g of immobilized cells (strain N-771), prepared in a manner similar to Example 12, are connected to each other in series, thereby providing flowing down through the upper part of the column 1 4% aqueous solution of acrylonitrile (using 0.05 M and phosphate buffer pH 8.0), at a temperature of 10 ° C, at a flow rate going down, 100 ml / h (, 0 h ). Thereafter, 100 hours of effluent is mixed with
q of acrylonitrile and allowed to flow down through the top of column 2 at a rate of 104 ml / h (, 04). Thus, an outlet stream in the form of an aqueous solution of acrylamide containing unreacted acrylonitrile with a reactivity ratio of 100% is continuously obtained. In addition, the concentration of acrylamide in this effluent is 10.3%.
Example 16. Three columns, equipped with shells, having an inner diameter of 3 cm and a length of 25 cm, each of which was filled with 40 g of immobilized cells (strain N-771), prepared in a manner similar to Example 12, are sequentially attached to each other, and dropping down through the top of the column 1 of a 4.5% aqueous solution of acrylonitrile (using 0.05 M phosphate buffer,, 0), at a temperature of 5 ° C,
The proposed method allows to simplify the process by using microorganisms that retain stable enzymatic activity for a long time, conduct the process at a low temperature, and eliminate the stage of purification of the cell solution, since a clear solution is obtained. At the same time, concentration T1 is target solution, or higher (32% vs. 20%)
with a downward flow rate of 50 ml / h (, 5 h). Post-25 is either at the level of the known 100 hours of this discharged effluent, sewn from 4.5 parts of acrylonitrile, and allowed to flow down through the upper
part of column 2 at speed
-).
downstream flow of 52.3 ml / h (53 hours, 104.5 parts of the effluent stream is then mixed with 4.5 parts of acrylonitrile and similarly allow it to flow down through column 3, and in this case the speed of the downstream is adjusted at the level of 54.5 ml / h (, 54). Thus, in this case, the formula of the invention is obtained continuously
thirty
1. The method of obtaining aqueous solutions of acrylamide or methacridamide by hydrolysis of the corresponding nitrile at pH 7.0-9.0 using strains
35 microorganisms, characterized in that, in order to simplify the process, the N-771 or N-774 strain of the Corynebacterium species, or the N-775 Nocardia species was used, deposited in the Indian flow at a geo-activity factor of 100%. In addition to this enzyme research institute, the acrylamide center in this output of the Industrial Science and Technological Agency is 16.6%.
Example 17. Three jacketed columns with an inner diameter of 3 cm, a length of 25 cm, each filled with 40 g of 45 immobilized cells (strain N-710, prepared analogously to example 12) are connected to each other in the Chiba Department of International Trade, lead at (-3) -15 ° C.
2. The POP.1 method, characterized in that the strains immobilized with polnacrylamide gel are used.
but, the 5.6% aqueous solution is passed through. 3. Method pop. 1, or acrylonitrile (using 50 u and with the fact that the process is phosphate buffer 0.05 M, pH 8) poured continuously in 3-7 sequentially converging flow through the top of column 1 of the connected columns. at and at a flow rate of 50 mp / h (, 5 h). Then 100 parts of the effluent are mixed with 5.6 parts of acrylonitrile and passed downward through
Priority on points dam: 55 04/28/78 - on PP.2 and 3; 03/29/78 - under Clause 1.
VNIIPI Order 905/63
Random polygons pr-tie, Uzhgorod, st. Project, 4
top of column 2 with a flow rate of 52.8 ml / h (, 53 h). Then 100 hours of expiration are mixed with 5.6 parts of acrylonitrile and, in the same way, they are successively passed downstream through column 3, adjusting the flow rate at 55.6 ml / h (, 56 hours). Thus, an effluent in the form of an acrylamide aqueous solution, not containing reacted acrylonitrile, is continuously obtained at a reaction ratio of 100%. The acrylamide concentration in this effluent is 20.2%.
The proposed method allows to simplify the process by using microorganisms that retain stable enzymatic activity for a long time, keep the process at a low temperature, and eliminate the stage of purification of the cell solution, since a clear solution is obtained. At the same time, the concentration T1 target solution is either higher (32% versus 20%),
either at the level of a known method

权利要求:
Claims (3)
[1]
1. The method of obtaining aqueous solutions of acrylamide or methacridamide by hydrolysis of the corresponding nitrile at pH 7.0-9.0 using strains
35 microorganisms, characterized in that, in order to simplify the process, they use the N-771 or N-774 strain of the Corynebacterium species, or N-775 of the Nocardia species, deposited in the Institute of Enzymatic Research Institute of Industrial Science and Technology
The Institute of Enzyme Research of the Agency for Industrial Science and Technological
The logistics of the Ministry of International Trade, the city of Chiba, and the process are conducted at (-3) -15 ° С.
[2]
2. The POP.1 method, characterized in that strains immobilized with full-acrylamide gel are used.
[3]
3. Method pop.1, otli.chayu- 50 y and, and with the fact that the process is carried out continuously in 3-7 series-connected columns.
Priority on points dam: 55 04/28/78 - on PP.2 and 3; 03/29/78 - under Clause 1.
Circulation 372
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同族专利:

公开号 | 公开日

FR2421212A1|1979-10-26|

FR2421212B1|1984-02-24|

DE2954531C2|1989-02-02|

US4248968A|1981-02-03|

DE2912292C2|1988-06-30|

RO82577A|1983-09-26|

RO77918A|1982-02-26|

DE2912292A1|1979-10-11|

NL7902453A|1979-10-02|

GB2018240A|1979-10-17|

RO82577B|1983-08-30|

IT1162484B|1987-04-01|

GB2018240B|1982-12-22|

IT7948496D0|1979-03-27|

引用文献:

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法律状态:

优先权:

申请号 | 申请日 | 专利标题

JP3531878A|JPS5617918B2|1978-03-29|1978-03-29|

JP5123778A|JPS571234B2|1978-04-28|1978-04-28|

JP5123678A|JPS5638118B2|1978-04-28|1978-04-28|

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