Method for production of n,n,n',n'-tetraacetylethylene diamine

FIELD: organic chemistry, detergents.

SUBSTANCE: claimed method includes interaction of ethylene diamine with tetraacetic acid. Obtained reaction mixture is treated with acetic anhydride at elevated temperature and N,N,N',N'-tetraacetylethylene diamine is isolated from reaction mass by crystallization. Reagent interaction is carried out in system of two continuous reactors acting in mixing-displacement regime at continuous raw material feeding such as ethylene diamine into top of the first reactor and acetic anhydride into top of the second reactor. Molar ratio of fresh acetic anhydride to ethylene diamine is 2.05-2.1. Temperature difference between top and bottom parts is maintained from 20 to 30°C for the first reactor and from 20 to 40°C for the second one. Compound of present invention is useful in detergent compositions.

EFFECT: target product of increased yield and purity, simplified process.

1 dwg, 1 tbl, 8 ex

 

The invention relates to the field of chemistry, and in particular to methods of obtaining N,N,N',N'-tetraacetylethylenediamine, which is an important auxiliary agent, which is used in synthetic detergents (detergents) and similar compounds, where it acts as an activator. Its use helps to reduce the temperature of water, which is especially desirable when washing textiles made of synthetic fibers and white linen.

N,N,N',N'-tetraacetylethylenediamine (hereinafter TAED) is obtained from acetic anhydride and N,N'- diacetylethylenediamine (DAAD), which, in turn, derived from Ethylenediamine (EDA) and acetic acid. These interactions are in equilibrium and are described by two equations:

It is known [U.S. Patent 4240980, MKI AS 102/00; publ. 23.12.1980] getting TIED in the apparatus of periodic action by the interaction of DEED with excess acetic anhydride, followed by joint distillation of acetic anhydride and the resulting acetic acid from the reaction mixture with the Department of TAED from acetic anhydride.

Since both forces are in equilibrium, the presence of water in the reaction mixture in the first stage and acetic acid in the reaction mixture of the second stage leads to the decrease of the output of TAED. All known solutions are focused on the shift of these equilibrium is shimodate towards the education of target products (DAAD and TAED) due to the removal of volatile components.

So, DAD can be obtained by the interaction between ED with acetic acid [UK patent GB 1335204, CL C07C 103/44; C07C 103/88, apob-10-24]. By this method diacetylethylenediamine get interaction diamines H2NRNH2(where R is alkylene with 2-6 carbon atoms) with acetic acid in a molar ratio of at least 1: 2, with removal of water formed during the interaction, and preferably before the reaction will be completed not more than 50%. Then spend acetylation product interaction with azetiliruet agent, but not acetic acid. This agent is acetic anhydride, and the result is a three - and/or tetraacetylethylenediamine. According to this method at the first stage, ED interacts with acetic acid in the ratio from stoichiometric to excess of 25%. The treatment of the reaction mixture with acetic anhydride in the second stage leads to the formation of TAED and acetic acid. Detachable acetic anhydride from the reaction mixture has a significant amount of acetic acid (40-50%), which helps reduce output when it is used in subsequent cycles. Attempts to remove all acid by prolonged heating of the reaction mixture at elevated temperatures lead to the formation of colored impurities, which may be undesirable.

The closest technical solution is with the persons obtaining N,N,N',N'-tetraacetylethylenediamine [U.S. Patent 4356321, MCI C07C 102/00; C07C 102/04, published. 26.10. 1982] - the prototype.

This method includes: (a) the interaction of DEED with acetic anhydride, resulting in the formation of the reaction mixture, consisting of TED, acetic acid and acetic anhydride, and (b) distillation of the reaction mixture with the extraction of acetic acid from it, then to complete the distillation of acetic acid added to a mixture of acetic anhydride and continue the distillation of acetic acid. The introduction of acetic anhydride after part of acetic acid is already removed, but to its distillation, get increased output is not proportional to the amount of anhydride used.

The interaction between DAD and acetic anhydride is carried out by heating to 120 170 °C for from 15 minutes to 3 hours when carrying out the distillation of acetic acid from the reaction mixture. Distillation is usually carried out until no formation of colored by-products.

The number of extractedthe distillate is usually from 15 to 40% by volume, preferably about 25% by volume, based on the amount of acetic anhydride added to DEAD. The preferred temperature interaction and distillation from 140 to 150°C.

After some acetic acid is distilled, is injected acetic anhydride, and then distillation of acetic acid from a mixture continues.

Central to the nom is carried out by distillation of acetic acid, the introduction of acetic anhydride in almost the same number as the number of extracted distillate, after which the distillation is continued, and the number of total ranging from 0.5 to 2.5, preferably from 0.8 to 1.5, the number of original remote distillate. The amount of distillate is extracted at each stage, is generally from 15 to 40% by volume based on acetic anhydride, originally added to DEAD.

Since acetic anhydride in this way is used for the acylation DEAD, and partly for acylation ED in the production process of TAED, the interaction may be in the form of periodic or continuous cyclic process. Preferably its implementation as a cyclical process in which each cycle includes:

- interaction DEED with acetic anhydride, at least part of which is extracted in a different cycle, and, thus, with the formation of the reaction mixture of TAED, acetic acid and acetic anhydride

- distillation of the reaction mixture by extraction from it of acetic acid together with acetic anhydride and then adding to the mixture of acetic anhydride before the end of the distillation of acetic acid and treatment of the residue after distillation to obtain almost pure TIED.

The use of acetic EN is idrica for acylation of DEAD, or in part, for the acylation of ED leads to the formation of excessive amounts of acetic acid, which in aqueous solution is a waste product and is subject to clearance of any method.

The process in separate cycles, even when its continuity, requires tracking and completion of each of the cycles, the availability of separate containers for the accumulation of intermediate products, and in General requires a rather cumbersome process flowsheet. In addition, the product yield is 45-50% based on the used of ED.

The challenge for the author of the invention is to simplify hardware technological design process of obtaining TIED and to create conditions for continuous shift of the equilibrium interaction towards the education of target products that will increase the output DEED in the first stage and TIED in the second stage and thus reduce the consumption of raw materials.

The essence of the invention is that a method of obtaining N,N,N',N'-tetraacetylethylenediamine from ethylene diamine and acetic anhydride, which includes the interaction of ethylene diamine with acetic acid, processing the obtained reaction mixture with acetic anhydride at elevated temperature with the excretion of N,N,N',N'-tetraacetylethylenediamine of the reaction mass is kristallizatsiei, characterized in that in order to obtain entry N,N,N',N'-tetraacetylethylenediamine not less than 95,0% (mass.) and high purity of not less than 99,0% (mass.) the interaction between the reagents is carried out in a system of two continuously operating reactors, each of which operates in the mode-mixing-displacement, when the supply of raw materials: ED in the upper portion of the first reactor and acetic anhydride in the upper part of the second reactor in a molar ratio of fresh acetic anhydride to the contrary: 2,05-2,1, while maintaining the temperature difference between the lower and upper parts of the reactor: the first 20 to 30°C, second from 20 to 40°C.

The process of obtaining TIED conducted at the facility, which consists of two reactors, the scheme of which is shown in the drawing, where: 1 - the first reactor, 2 for the second reactor, 3 - node separation of acetic acid and water, 4 - node separation of acetic anhydride and acetic acid, 5 - mixing zone, 6 - zone displacement, 7 - flow Ethylenediamine, 8 threads acetic acid, 9 - flows of acetic anhydride, 10 - reaction mass, 11 - water reaction.

The device operates in continuous mode, the continuous supply of feedstock - ED and acetic anhydride simultaneously in two reactors and a counter-flow motion volatile reaction products: water and acetic acid. ED served in the first reactor, and the CA is just anhydride - in the second reactor with continuous circulation between the reactor acetic acid resulting from the acetylation DEAD acetic anhydride. Using the sectional heat exchangers in the reactor specified temperature, increasing the length of the reactor from the entrance of the reagents to the exit of the reaction mass.

Such technological organization reacting flows and maintaining desired temperature conditions provides a high ratio of reactants at the inlet of the reactor and increasing the length of the reactor. At the same time, the total molar ratio of ethylene diamine and acetic anhydride is minimum corresponds to not less than 95%of the resultant output acetic anhydride and is 2.1. (A ratio of 2 corresponds to 100%final theoretical yield).

Installation synthesis of TAED consists of two reactors, column type, each of which consists of two zones. In the upper part of the device is a mixing zone, in which due to the intensive circulation of the fluid (for example, by using a circulation pump) hydrodynamic mode of motion of the reaction mass is approaching the regime of ideal mixing. The mixing zone is a relatively small part of the volume of the apparatus 10 to 20%. The lower part of the reactor, in which mainly chemical processes take place, have the horizon of the global partitions, made in the form of bubble cap trays and designed to prevent mixing of the reaction mass in the entire volume of the device and to bring the hydrodynamic regime of the motion of the reaction mass in the lower part of the apparatus to the ideal mode of displacement. The apparatuses 3, 4, operating as a strengthening of distillation columns for low-boiling components, filled with any nozzle, preferably regular. In the upper part of the reactor are the separation zone for separating the exhaust vapor from the liquid. There are devices to return the condensed liquid phase. Site of synthesis of TAED contains exchangers for condensing vapors of low-boiling components (water in the first reactor, acetic acid in the second reactor), intermediate collections and other equipment necessary for the implementation of the process. To maintain specified temperature in the reactor apparatus equipped sectional shirts, which circulates steam or the appropriate carrier. When creating large production capacity, in order to avoid creating high reactors may be divided areas of each of the reactor into two columns, installed in parallel, and a different location of the reaction and distillation zones, preserving shown in the drawing of the structure of liquid and vapor flows.

Technological process on the plant carried out as follows.

In the upper part of the reactor 1 to the first plate continuously served the original reagents - ED and return acetic acid from the distillation units 3 and 4, as a rule, with a significant excess of acetic acid. Formed on the first plate reaction mass is intensively mixed with the circulating pump. The liquid portion of the reaction mass through the holes in the plates under the action of gravity flows to the exit of the reactor. Such movement of the liquid phase through a system of plates, each of which implements a mode of mixing, in General, to apparatus generates the mode displacement in the liquid phase of the reaction mass. Produced water on each plate to evaporate and vapor mixture from a source of acetic acid through the holes in the caps of the plates is sent to separation unit 3, from which acetic acid is returned to the reactor part of the site of synthesis, and the main part of the water is recycled. High-efficiency showerhead, phlegm and adjustable temperature provide almost complete return of acetic acid in the reaction zone and the withdrawal of all water with a low content of acetic acid in water (not more than 2%). In the first reactor with coolant in the sectional shirt temperature is maintained in the range of 15-145° With increase in temperature along the length of reactor (downward) by 20-30°C. Pressure mode, the presence of a temperature gradient along the height of the reactor and the selected design of the reactor provide the increasing of the molar ratio of the reagents on each plate of the reactor from 5 - 8 at the entrance to several hundred at the output, which in turn provides the water content at the output of not more than 2%. The total consumption of reagents in the first reactor is calculated so that the residence time in the reactor was not less than 0.5 hour.

The resulting solution DEED in acetic acid from the bottom of the reactor 1 is sent to the mixing zone of the reactor 2 to the first plate, which simultaneously served acetic anhydride in a molar ratio with DAD not less than 8, and similar to the process in the first reactor by means of the circulation pump on the first plate creates a blend mode. Next, the liquid phase of the reaction mass flows down the plates down mode displacement, and formed in the acetic acid evaporates, and a pair of acetic acid together with pairs of acetic anhydride in the countercurrent mode move up and out in the separation unit 4. Acetic acid is directed into the reactor 1, and acetic anhydride is returned to the reactor 2. In the reactor 2 through the coolant supply to the sectional shirt temperature is maintained in the range of 135-185° With temperature control so that the temperature in the reactor from the entrance to the exit of the reactor was increased by 20-40°C. Process parameters and design of the 2nd reactor (similar to those for the first reactor) provide the increasing of the molar ratio of the reactants, the degree of conversion of the starting compounds and achieve a total output of TAED not less than 95%, the content of impurities in the selected crystallization trade TAED not exceed 0.2%. The content of acetic acid in the reaction mass at the outlet of the second reactor does not exceed 3%. The total consumption of reagents in the second reactor is calculated so that the residence time in the reactor for at least 1 hour.

The selection of TIED after cooling the reaction mass leaving the second reactor, produced in the traditional techniques of crystallization, filtration, washing and drying.

The result achieved is set before the authors of the task is the process of obtaining TAED is held in a compact twin installation of continuous action, providing a continuous removal of low-boiling products, thereby increasing the output DAD up to 98-99%and the total yield of TIED - above 95%, as well as to ensure almost complete conversion of raw materials into desired products with a molar ratio of UA to ED not more than 2.1.

EXAMPLES. In table 1 a CR is entered results 8 examples of synthesis of TAED.

General description of the process.

Synthesis of TAED conducted at the facility, the concept of which is shown in the drawing. In the reactor POS 1, which is a vertical column type apparatus, an inner diameter of 50 mm and a height of 0.25 m, equipped with a septa cap type, in continuous mode the dosing pumps (not specified) was applied Ethylenediamine acetic acid and with predetermined costs. In the area above the top plate reagents were intensively mixed with the circulating pump. The temperature in the mixing zone was maintained in the range of 115 - 120°C. height of reactor (downward) temperature monotonically increased up to 140 - 145°in the lower part of the apparatus. When the movement of the liquid phase down was intense boiling and vapor outlet in the separation (distillation) the host part of the synthesis of 3. The separated acetic acid was mixed with MC coming out of the column 4, and returned to the reactor 1 and the water was removed from the installation. Reaction mass from the reactor 1 by gravity flow was directed into the upper part of the reactor 2 (mixing zone), where it was mixed with fed into the reactor with acetic anhydride using a dosing pump. In the mixing zone temperature was 135 - 145°and the height of the reactor temperature is monotonically increased to 160 - 185°in the lower part of the apparatus. Vapour phase, spin-off about this is Jesse, are condensed and separated in column 4, the acetic anhydride was returned to the reactor 2, and acetic acid were sent to the inlet of the first reactor 1. At the outlet of the second reactor was measured by a flow of the reaction mass and its composition.

From the reaction mass obtained in the conditions described in these examples were provided of TAED method of crystallization. The isolated product is a crystal white needle form. The basic substance content not less than 98%.

Examples of the synthesis of TAED on continuously operating facility.

Table 1.

No.

p/p
Name parameters

P R I M E R S
12345678


1.
The flow of components

at the entrance to the installation.


1.1..
In item 1

ED, ml/h

g/h


135

120


135

120


135

120


135

120


168



168

150


168

150


168

150
1.2.MC, ml/h

g/h
357

375
400

420
380

400
410

430
430

450
524

550
476

500
457

480
1.3.2

UA, ml/h

g/h


1220

1320


1160

1250


1280

1380


1340

1450


1667

1800


1574

1700


1480

1600


1530

1650


2.
The flow of components at the output of the installation
2.1.An aqueous solution of 3 ml/h

g/h


75

75


70

70


76

76


74

74


87

87


90

90


90

90


86

86




2.2.
The solution composition, % wt.

In the

MC


98,7

1,3


98,6

1,4


97,4

2,6


98

2


97,7

2,3


96,7

3,3


of 97.8

2,2


98,8

1,2


2.3.
The solution TIED in UA from pos.2

ml/h

g/h


1186

1365


1130

1300


1238

1424


1300

1496


1620

1863


1530

1760


1444

1660


1490

1714


2.4.
The solution composition, % wt.

TAED

UA

CC

impurities


33.0

65.5

1.1

0.4


34.5

64.1

0.6

0.8


31.7

67.0

0.7

0.6


30.0

69.2

0.4

0.4


30.3

68.4

0.8

0.5


31.4

66.8

1.0

0.8


33.9

64.6

0.9

0.6


S

65.7

1.0

0.8
3.The temperature in the reactors °


3.1


top of the 1st


115-120



120-125


120-125


115-120


125-130


120-125


115-120


120-125


3.2.


bottom of the 1st


130-135


130-135


135-140


130-135


145-150


135-140


140-145


140-145
3.3.top of the 2nd140-145145-150150-155140-145140-145145-150135-140140-145
3.4.bottom of the 2nd160-165165-170170-175175-180180-185175-180180-185185-190
4.The output of TAED % on ED on the content of TAED in solution.

98.7



98.2


98.9


98.5


of 99.1


of 98.2


98,6


98,0

< num="40"> The method of obtaining N,N,N′,N′-tetraacetylethylenediamine from ethylene diamine and acetic anhydride, which includes the interaction of ethylene diamine with acetic acid, processing the obtained reaction mixture with acetic anhydride at elevated temperature with the excretion of N,N,N′,N′-tetraacetylethylenediamine from the reaction mixture by crystallization, wherein the interaction of the reagents is carried out in a system of two continuously operating reactors, each of which operates in the mode-mixing-displacement, when the continuous supply of raw materials - Ethylenediamine - at the top the portion of the first reactor and acetic anhydride in the upper part of the second reactor in a molar ratio of fresh acetic anhydride to Ethylenediamine as 2,05-2,1, while maintaining the temperature difference between the lower and upper parts of the reactor: the first 20 to 30°C, second from 20 to 40°C.



 

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16 cl, 11 ex

FIELD: chemistry.

SUBSTANCE: present invention pertains to the method of making compounds with formula , involving reaction of but-2-enoic acid with chlorotrimethylsilane, bromination of the obtained trimethylsilylcrotonate with N-bromosuccinimide, reaction of the obtained trimethylsilyl-4-bromocrotonate or methyl or ethyl 4-bromocrotonate with dimethylamine so as to obtain 4-dimethylaminocrotonic acid, its separation in form of hydrochloride and chlorination with oxalyl chloride. The method allows for obtaining 4-dimethylamino-2-butenoylchloride, suitable for use as an intermediate compound in the synthesis of pharmaceutically active protein kinase inhibitors.

EFFECT: obtaining the agent, suitable for use as an intermediate compound in the synthesis of pharmaceutically active protein kinase inhibitors.

1 cl, 2 dwg, 3 ex

FIELD: chemistry; food products.

SUBSTANCE: present invention relates to use of N-isobutylamide 2E,4E-decadienoic acid (trans-pellitorine) as an aromatic substance, with a sialagogue but not burning effect in compositions used for food, oral hygiene or consumed for delectation, where trans-pellitorine is used in amounts of 20 parts/million in terms of the total mass of the composition. The invention also relates to the aromatic composition, with a sialagogue but not burning effect, containing trans-pellitorine in amounts of 20 parts/million in terms of the total mass of the composition, as well as to the method of obtaining trans-pellitorine. The invention also pertains to the method of obtaining N-isobutylamide 2E,4E-decadienoic acid.

EFFECT: obtaining a substance with sialagogue and/or irritant effect, as well as a wide neutral aromatic profile.

6 cl, 7 ex

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