WO2013006092A1 - Method for preparing melamine cyanurate - Google Patents

Method for preparing melamine cyanurate Download PDF

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Publication number
WO2013006092A1
WO2013006092A1 PCT/RU2012/000525 RU2012000525W WO2013006092A1 WO 2013006092 A1 WO2013006092 A1 WO 2013006092A1 RU 2012000525 W RU2012000525 W RU 2012000525W WO 2013006092 A1 WO2013006092 A1 WO 2013006092A1
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Prior art keywords
melamine cyanurate
melamine
reaction zone
cyanuric acid
water
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PCT/RU2012/000525
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French (fr)
Russian (ru)
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WO2013006092A8 (en
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Владимир Мейерович КАРЛИК
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РАСНЕЦОВ, Лев Давидович
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Priority to CN201280033642.0A priority Critical patent/CN103732582A/en
Publication of WO2013006092A1 publication Critical patent/WO2013006092A1/en
Publication of WO2013006092A8 publication Critical patent/WO2013006092A8/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • C07D251/70—Other substituted melamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C07D251/34—Cyanuric or isocyanuric esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms

Definitions

  • the invention relates to organic chemistry, and in particular to an improved method for producing melamine cyanurate, which is used in various compositions as a flame retardant.
  • CM melamine cyanurate
  • M melamine
  • CC cyanuric acid
  • a known method of producing melamine cyanurate comprising heating a dry powder mixture of M and CK at 250-500 ° C in the absence of a liquid medium (patent US5493023, publ. 02.20.1996).
  • the ratio of M to CK is from 1: 0.5 to 1: 2.0 (in moles), best from 1: 0.9 to 1: 1.1.
  • the process is preferably carried out in an inert gas medium, for example N. Pre-mix the components at room temperature. In practice, this method is carried out by the interaction of components in the melt. Due to the difference in sublimation temperatures M and CC, the process is accompanied by a loss of reagents.
  • the selection of the target product is carried out by distillation of water by vacuum followed by drying.
  • the disadvantage of this method is the multi-stage process, requiring large energy costs associated with the need for fine grinding of the starting products and evacuation. Drying of the product, in addition to energy consumption (supply of hot air), is accompanied by large losses of the target product, which is carried away by the air flow into the atmosphere, which leads to environmental pollution and requires the installation of bulky and expensive treatment facilities.
  • the objective of the proposed technical solution is to create a method with obtaining target products with high yield, without large water and energy costs, which could be carried out continuously.
  • a method for producing melamine cyanurate which consists in the fact that a mixture consisting of melamine, cyanuric acid in a ratio of mol per mole, and water, comprising 2-30% by weight of dry reagents, is fed to the reaction zone in oncoming air flows with a pressure of 2 - 10 kgf / cm 2 at a temperature of 10 ° C to 100 ° C. If the conditions for the implementation of the method are not observed, the quality and yield of the target product decreases, and energy costs increase.
  • an antistatic agent with an electrostatic charge leakage half-life ⁇ 10 is additionally introduced into the initial reagent mixture.
  • Surfactants can be used as antistatic agents in the form of 2- 5% solutions or emulsions, alcohols, for example, methanol or ethanol in an amount of 0.1-5% of the amount of water that is introduced into the material during its processing, or a mixture thereof.
  • devices for periodic shaking are placed on some apparatuses and filters.
  • the reaction mixture consisting (in kg) of 1.9 melamine, 1.93 cyanuric acid - the ratio of mole per mole - and 0.97 water (25% by weight of dry reagents) is fed into the reaction zone for 40 seconds volume of 80 cm 3 in oncoming air flows with a pressure of 2 atm (kgf / cm 2 ), each with a temperature of 100 ° ⁇ and a space velocity of 150 nm 3 / h.
  • melamine cyanurate is obtained in an amount of 3.84 kg with a basic substance content of about 96%, moisture 0.3% and with a particle size of 75-130 microns.
  • the residence time of the reactants in the reaction zone is ⁇ 0.001 sec.
  • the reaction mixture consisting (in kg) of 2.5 melamine, 2.6 cyanuric acid and 0.8 water (16% by weight of dry products), is fed into the reaction zone with a volume of 80 cm 3 in counter flows for 45 sec. air with a pressure of 6 atm (kgf / cm 2 ), a temperature of 55 ° C and a space velocity of 225 nm 3 / h each.
  • melamine cyanurate is obtained in an amount of 5.12 kg with a basic substance content of about 95%, moisture 0.4% and with a particle size of 50-100 microns.
  • the residence time of the reactants in the reaction zone is ⁇ 0.0005 sec.
  • the reaction mixture consisting (in kg) of 1, 26 melamine, 1.3 cyanuric acid and 0.05 water (2% by weight of dry reagents), is fed into the reaction zone with a volume of 80 cm 3 for 20 seconds, as in examples 1 and 2, at a pressure of 10 atm (kgf / cm 2 ), a temperature of 10 ° C and a space velocity of 300 nm 3 / h each.
  • the output is 2.57 kg of melamine cyanurate with a basic substance content of about 95%, moisture 0.45% and with a particle size of 20-50 microns.
  • the residence time of the reactants in the reaction zone is ⁇ 0.0005 sec.
  • the reaction mixture consisting of 1, 9 kg of melamine, 1, 93 kg of cyanuric acid and 1, 16 kg of water (30% by weight of dry reagents), is fed into the reaction zone with a volume of 80 cm 3 in 40 minutes air with a pressure of 2 atm (kgf / cm 2 ), a temperature of 100 ° C and a space velocity of 150 nm 3 / h each.
  • melamine cyanurate is obtained in an amount of 3.81 kg with a basic substance content of about 95% and a moisture content of 0.5%. Particle size 75 - 130 microns.
  • the residence time of the reactants in the reaction zone is ⁇ 0.001 sec.
  • Melamine and cyanuric acid in a molar ratio, as well as water in an amount of 5% by weight of dry reagents, are continuously fed into a mixer at a temperature of 20 ° C and then into a reaction zone with a volume of 80 cm 3 in oncoming air flows with a pressure of ⁇ 10 atm and a space velocity of 200 nm 3 / h each.
  • the product passing through the dust and moisture separation system, enters the drive and then is packed into big bags or bags.
  • Melamine cyanurate is obtained with a basic substance content of about 95%, moisture 0.45% and a particle size of 20-50 microns.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fireproofing Substances (AREA)

Abstract

The invention relates to organic chemistry, specifically to an improved method for preparing melamine cyanurate, which is used in various compositions as a fire retardant. When reacting cyanuric acid and melamine in a molar ratio in the presence of 2-30% water based on the mass of dry reagents at a temperature of from 10 to 100°С in air counterflows at 2-10 kp/cm2, melamine cyanurate with a high percentage yield of end product is produced and with a reduced consumption of energy. A further advantage of the proposed method consists in the possibility of implementing said method in the continuous mode.

Description

Способ получения цианурата меламина  The method of producing melamine cyanurate
Область техники Technical field
Изобретение относится к органической химии, а именно к усовер- шенствованному способу получения цианурата меламина, который при- меняют в различных композициях в качестве антипирена.  The invention relates to organic chemistry, and in particular to an improved method for producing melamine cyanurate, which is used in various compositions as a flame retardant.
Предшествующий уровень техники State of the art
Известен способ получения цианурата меламина (ЦМ) взаимодей- ствием меламина (М) и циануровой кислоты (ЦК) при соотношении компонентов от 1 :9 до 9: 1 (мае.) в водной среде (от 20 до 2000% вес. к весу всей смеси) в цилиндрическом двухлопастном смесителе при 0- 250°С в течение от 5 мин до 5 часов (патент JP54055587, опубл. 02.05.1979). Недостатками этого способа являются трудности при выде- лении целевого продукта, связанные с необходимостью фильтрования, сушки, размола ЦМ.  A known method of producing melamine cyanurate (CM) by the interaction of melamine (M) and cyanuric acid (CC) with a ratio of components from 1: 9 to 9: 1 (May.) In an aqueous medium (from 20 to 2000% wt. mixture) in a cylindrical two-blade mixer at 0-250 ° C for 5 minutes to 5 hours (patent JP54055587, publ. 02.05.1979). The disadvantages of this method are the difficulties in isolating the target product associated with the need for filtering, drying, grinding of CM.
Известен способ получения цианурата меламина, включающий на- гревание сухой порошкообразной смеси М и ЦК при 250-500°С в отсут- ствии жидкой среды (патент US5493023, опубл. 20.02.1996). Соотноше- ние М и ЦК составляет от 1 :0,5 до 1 :2,0 (в молях), лучше всего от 1 :0,9 до 1 : 1,1. Процесс желательно осуществлять в среде инертного газа, на- пример N . Предварительно смешивают компоненты при комнатной температуре. Практически данный способ осуществляют взаимодейст- вием компонентов в расплаве. Из-за разницы температур сублимации М и ЦК процесс сопровождается потерей реагентов. Кроме того, необхо- димо дорогостоящее оборудование (автоклав), а процесс сопровождает- ся большими энергозатратами, связанными с необходимостью поддер- жания высокой температуры в течение длительного времени (до не- скольких часов). Наиболее близким к заявляемому изобретению является способ, включающий взаимодействие меламина и циануровой кислоты при со- отношении М:ЦК=1 : 1 (моль) с последующим нагреванием, вакуумиро- ванием смеси (содержание воды 50-500% вес). Для облегчения смеши- вания используют тонко измельчённые до размера диаметра частиц < 100 мкм исходные компоненты (патент JP55147266, опубл. 17.1 1.1980). A known method of producing melamine cyanurate, comprising heating a dry powder mixture of M and CK at 250-500 ° C in the absence of a liquid medium (patent US5493023, publ. 02.20.1996). The ratio of M to CK is from 1: 0.5 to 1: 2.0 (in moles), best from 1: 0.9 to 1: 1.1. The process is preferably carried out in an inert gas medium, for example N. Pre-mix the components at room temperature. In practice, this method is carried out by the interaction of components in the melt. Due to the difference in sublimation temperatures M and CC, the process is accompanied by a loss of reagents. In addition, expensive equipment (autoclave) is required, and the process is accompanied by high energy costs associated with the need to maintain high temperature for a long time (up to several hours). Closest to the claimed invention is a method comprising the interaction of melamine and cyanuric acid with a ratio of M: CK = 1: 1 (mol), followed by heating, evacuating the mixture (water content 50-500% weight). To facilitate mixing, finely ground starting components are used finely ground to a particle diameter <100 μm (patent JP55147266, publ. 17.1 1.1980).
Выделение целевого продукта осуществляют путём отгонки воды вакуумированием с последующей сушкой. Недостатком способа являет- ся многостадийность процесса, требующего больших энергозатрат, свя- занных с необходимостью тонкого измельчения исходных продуктов и вакуумированием. Сушка продукта, кроме энергозатрат (подача горяче- го воздуха), сопровождается большими потерями целевого продукта, ко- торый уносится потоком воздуха в атмосферу, что приводит к загрязне- нию окружающей среды и требует установки громоздких и дорогостоя- щих очистных сооружений.  The selection of the target product is carried out by distillation of water by vacuum followed by drying. The disadvantage of this method is the multi-stage process, requiring large energy costs associated with the need for fine grinding of the starting products and evacuation. Drying of the product, in addition to energy consumption (supply of hot air), is accompanied by large losses of the target product, which is carried away by the air flow into the atmosphere, which leads to environmental pollution and requires the installation of bulky and expensive treatment facilities.
Раскрытие изобретения Disclosure of invention
Задачей предлагаемого технического решения является создание способа с получением целевых продуктов с высоким выходом, без больших водо- и энергозатрат, который можно было бы осуществлять непрерывно.  The objective of the proposed technical solution is to create a method with obtaining target products with high yield, without large water and energy costs, which could be carried out continuously.
Поставленная задача решается тем, что создан способ получения цианурата меламина, который заключается в том, что смесь, состоящую из меламина, циануровой кислоты в соотношении моль на моль, и воды, составляющую 2 - 30 % от массы сухих реагентов, подают в реакцион- ную зону во встречных потоках воздуха с давлением 2 - 10 кгс/см2 при температуре от 10°С до 100°С. При несоблюдении условий осуществления способа снижается ка- чество и выход целевого продукта, увеличиваются энергетические за- траты. The problem is solved in that a method for producing melamine cyanurate is created, which consists in the fact that a mixture consisting of melamine, cyanuric acid in a ratio of mol per mole, and water, comprising 2-30% by weight of dry reagents, is fed to the reaction zone in oncoming air flows with a pressure of 2 - 10 kgf / cm 2 at a temperature of 10 ° C to 100 ° C. If the conditions for the implementation of the method are not observed, the quality and yield of the target product decreases, and energy costs increase.
В результате использования предложенного технического решения удалось добиться получения высокого процента выхода целевого про- дукта, снижения энергетических затрат за счёт уменьшения количества используемой в процессе воды, исключения стадий сушки, размола, просева. Ещё одним достоинством предлагаемого способа является воз- можность его осуществления в непрерывном режиме.  As a result of using the proposed technical solution, it was possible to obtain a high percentage of the yield of the target product, reduce energy costs by reducing the amount of water used in the process, eliminating the stages of drying, grinding, sifting. Another advantage of the proposed method is the possibility of its implementation in continuous mode.
Для получения продукта различной дисперсности и предотвраще- ния его налипания и агломерации при осуществлении способа в непре- рывном режиме в исходную смесь реагентов дополнительно вводится антистатик с полупериодом утечки электростатических зарядов < 10. В качестве антистатика могут быть использованы поверхностно-активные вещества в виде 2-5%-ных растворов или эмульсий, спирты, например, метанол или этанол в количестве 0,1-5% от количества воды, которые вводят в материал при его переработке, или их смесь. Кроме того, на не- которых аппаратах и фильтрах размещают устройства для периодиче- ского встряхивания. Варианты осуществления изобретения  In order to obtain a product of various dispersion and to prevent its sticking and agglomeration during continuous operation of the method, an antistatic agent with an electrostatic charge leakage half-life <10 is additionally introduced into the initial reagent mixture. Surfactants can be used as antistatic agents in the form of 2- 5% solutions or emulsions, alcohols, for example, methanol or ethanol in an amount of 0.1-5% of the amount of water that is introduced into the material during its processing, or a mixture thereof. In addition, devices for periodic shaking are placed on some apparatuses and filters. Embodiments of the invention
Сущность данного изобретения иллюстрируется следующими примерами.  The essence of the present invention is illustrated by the following examples.
Пример 1.  Example 1
Реакционную смесь, состоящую (в кг) из 1 ,9 меламина, 1,93 циа- нуровой кислоты - соотношение моль на моль - и 0,97 воды (25% от мас- сы сухих реагентов) в течение 40 секунд подают в реакционную зону объёмом 80 см3 во встречных потоках воздуха с давлением 2 атм (кгс/см2), температурой 100°С и объёмной скоростью по 150 нм3/ч каж- дый. The reaction mixture, consisting (in kg) of 1.9 melamine, 1.93 cyanuric acid - the ratio of mole per mole - and 0.97 water (25% by weight of dry reagents) is fed into the reaction zone for 40 seconds volume of 80 cm 3 in oncoming air flows with a pressure of 2 atm (kgf / cm 2 ), each with a temperature of 100 ° С and a space velocity of 150 nm 3 / h.
На выходе из реакционной зоны получают цианурат меламина в количестве 3,84 кг с содержанием основного вещества около 96%, влаги 0,3% и с размером частиц 75-130 мкм. Время пребывания реагентов в реакционной зоне ~ 0,001 сек.  At the exit of the reaction zone, melamine cyanurate is obtained in an amount of 3.84 kg with a basic substance content of about 96%, moisture 0.3% and with a particle size of 75-130 microns. The residence time of the reactants in the reaction zone is ~ 0.001 sec.
Пример 2. ,  Example 2.
Реакционную смесь, состоящую (в кг) из 2,5 меламина, 2,6 циану- ровой кислоты и 0,8 воды (16% от массы сухих продуктов), в течение 45 сек подают в реакционную зону объёмом 80 см3 во встречных потоках воздуха с давлением 6 атм (кгс/см2), температурой 55°С и объёмной ско- ростью по 225 нм3/ч каждый. The reaction mixture, consisting (in kg) of 2.5 melamine, 2.6 cyanuric acid and 0.8 water (16% by weight of dry products), is fed into the reaction zone with a volume of 80 cm 3 in counter flows for 45 sec. air with a pressure of 6 atm (kgf / cm 2 ), a temperature of 55 ° C and a space velocity of 225 nm 3 / h each.
На выходе получают цианурат меламина в количестве 5,12 кг с со- держанием основного вещества около 95%, влаги 0,4% и с размером частиц 50 - 100 мкм. Время пребывания реагентов в реакционной зоне ~ 0,0005 сек.  At the output, melamine cyanurate is obtained in an amount of 5.12 kg with a basic substance content of about 95%, moisture 0.4% and with a particle size of 50-100 microns. The residence time of the reactants in the reaction zone is ~ 0.0005 sec.
Пример 3.  Example 3
Реакционную смесь, состоящую (в кг) из 1 ,26 меламина, 1,3 циа- нуровой кислоты и 0,05 воды (2% от массы сухих реагентов), в течение 20 сек подают в реакционную зону объёмом 80 см3, как в примерах 1 и 2, при давлении 10 атм (кгс/см2), температуре 10°С и объёмной скоростью по 300 нм3/ч каждый. The reaction mixture, consisting (in kg) of 1, 26 melamine, 1.3 cyanuric acid and 0.05 water (2% by weight of dry reagents), is fed into the reaction zone with a volume of 80 cm 3 for 20 seconds, as in examples 1 and 2, at a pressure of 10 atm (kgf / cm 2 ), a temperature of 10 ° C and a space velocity of 300 nm 3 / h each.
На выходе получают 2,57 кг цианурата меламина с содержанием основного вещества около 95%, влаги 0,45% и с размером частиц 20 - 50 мкм. Время пребывания реагентов в реакцйонной зоне ~ 0,0005 сек.  The output is 2.57 kg of melamine cyanurate with a basic substance content of about 95%, moisture 0.45% and with a particle size of 20-50 microns. The residence time of the reactants in the reaction zone is ~ 0.0005 sec.
Пример 4.  Example 4
Реакционную смесь, состоящую из 1 ,9 кг меламина, 1 ,93 кг циану- ровой кислоты и 1 ,16 кг воды (30% от массы сухих реагентов), в течение 40 сек подают в реакционную зону объёмом 80 см3 во встречных пото- ках воздуха с давлением 2 атм (кгс/см2), температурой 100°С и объёмной скоростью по 150 нм3/ч каждый. The reaction mixture, consisting of 1, 9 kg of melamine, 1, 93 kg of cyanuric acid and 1, 16 kg of water (30% by weight of dry reagents), is fed into the reaction zone with a volume of 80 cm 3 in 40 minutes air with a pressure of 2 atm (kgf / cm 2 ), a temperature of 100 ° C and a space velocity of 150 nm 3 / h each.
На выходе из реакционной зоны получают цианурат меламина в количестве 3,81 кг с содержанием основного вещества около 95% и вла- ги 0,5%. Размер частиц 75 - 130 мкм. Время пребывания реагентов в ре- акционной зоне ~ 0,001 сек.  At the exit from the reaction zone, melamine cyanurate is obtained in an amount of 3.81 kg with a basic substance content of about 95% and a moisture content of 0.5%. Particle size 75 - 130 microns. The residence time of the reactants in the reaction zone is ~ 0.001 sec.
Пример 5.  Example 5
Меламин и циануровую кислоту в Мольном соотношении, а также воду в количестве 5% от массы сухих реагентов непрерывно подают в смеситель при температуре 20°С и далее в реакционную зону объёмом 80 см3 во встречных потоках воздуха с давлением ~ 10 атм и объёмной скоростью 200 нм3/ч каждый. Melamine and cyanuric acid in a molar ratio, as well as water in an amount of 5% by weight of dry reagents, are continuously fed into a mixer at a temperature of 20 ° C and then into a reaction zone with a volume of 80 cm 3 in oncoming air flows with a pressure of ~ 10 atm and a space velocity of 200 nm 3 / h each.
На выходе из реакционной зоны продукт, проходя через систему пылевлаготделения, поступает в накопитель и далее затаривается в биг- беги или мешки. Получают цианурат меламина с содержанием основно- го вещества около 95%, влаги 0,45% и размером частиц 20 - 50 мкм.  At the outlet of the reaction zone, the product, passing through the dust and moisture separation system, enters the drive and then is packed into big bags or bags. Melamine cyanurate is obtained with a basic substance content of about 95%, moisture 0.45% and a particle size of 20-50 microns.

Claims

Формула изобретения Claim
1. Способ получения цианурата меламина, включающий взаимо- действие циануровой кислоты и меламина в мольном соотношении 1 : 1 в присутствии воды, отличающийся тем, что содержание воды составляет 2 - 30% от массы сухих реагентов, смесь реагентов вводят в реакцион- ную зону при температуре от 10 до 100°С во встречных потоках воздуха 2 - 10 кгс/см2. , : 1. A method of producing melamine cyanurate, comprising the interaction of cyanuric acid and melamine in a molar ratio of 1: 1 in the presence of water, characterized in that the water content is 2-30% by weight of dry reagents, the mixture of reagents is introduced into the reaction zone at temperature from 10 to 100 ° C in oncoming air flows 2 - 10 kgf / cm 2 . ,:
PCT/RU2012/000525 2011-07-07 2012-07-02 Method for preparing melamine cyanurate WO2013006092A1 (en)

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RU2758252C1 (en) * 2021-03-15 2021-10-27 Федеральное государственное автономное образовательное учреждение высшего образования «Национальный исследовательский Томский государственный университет» Method for obtaining melamine cyanurate

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JPH11292861A (en) * 1998-04-09 1999-10-26 Mitsubishi Chemical Corp Melamine cyanurate and its production
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US20080312360A1 (en) * 2004-10-15 2008-12-18 Renier Henricus Maria Kierkels Melamine Cyanurate in Crystalline Form
WO2006095337A2 (en) * 2005-03-07 2006-09-14 Bromine Compounds Ltd. A process for the preparation of melamine cyanurate
RU2292341C1 (en) * 2005-05-05 2007-01-27 Институт синтетических полимерных материалов (ИСПМ) им. Н.С. Ениколопова РАН Method for preparing melamine adduct with acid

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