JPH04364173A - Production of isocyanuric acid - Google Patents
Production of isocyanuric acidInfo
- Publication number
- JPH04364173A JPH04364173A JP30699990A JP30699990A JPH04364173A JP H04364173 A JPH04364173 A JP H04364173A JP 30699990 A JP30699990 A JP 30699990A JP 30699990 A JP30699990 A JP 30699990A JP H04364173 A JPH04364173 A JP H04364173A
- Authority
- JP
- Japan
- Prior art keywords
- urea
- alkali metallic
- alkali metal
- solvent
- isocyanuric acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000004202 carbamide Substances 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- -1 lithium hydride) Chemical class 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 17
- 239000002904 solvent Substances 0.000 abstract description 9
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 238000007796 conventional method Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 2
- 229910000103 lithium hydride Inorganic materials 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract 5
- 229910000765 intermetallic Inorganic materials 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000004132 cross linking Methods 0.000 abstract 1
- 230000002070 germicidal effect Effects 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 239000013462 industrial intermediate Substances 0.000 abstract 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 abstract 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- 150000005218 dimethyl ethers Chemical class 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- WNVQBUHCOYRLPA-UHFFFAOYSA-N triuret Chemical compound NC(=O)NC(=O)NC(N)=O WNVQBUHCOYRLPA-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は尿素を原料としてイソシアヌル酸（以下、ＣＡ
と略記する。）を製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention provides isocyanuric acid (hereinafter referred to as CA) using urea as a raw material.
It is abbreviated as ).
〔従来の技術及び発明が解決しようとする課題〕ＣＡは
工業的に有用な中間原料である。例えば、ＣＡを塩素化
した塩化イソシアヌルは、粒状で簡便かつ活性が高いプ
ール殺菌剤として広く用いられており、又、アリル化し
たアリルイソシアヌレートは樹脂改質剤や架橋助剤とし
て好適に用いられている。[Prior art and problems to be solved by the invention] CA is an industrially useful intermediate raw material. For example, isocyanuric chloride, which is obtained by chlorinating CA, is widely used as a granular, simple, and highly active pool disinfectant, and allyl isocyanurate, which is obtained by allylating it, is suitably used as a resin modifier and crosslinking agent. ing.
このような工業的に有用なＣＡは、一般に有機溶媒中で
尿素を加熱することにより製造される。Such industrially useful CA is generally produced by heating urea in an organic solvent.
その反応を示せば下記式（１）のとおりである。The reaction is shown in the following formula (1).
しかし、アンモニアガス発生雰囲気下、高温で長時間溶
媒を加熱すると溶媒が一部劣化する。そこで溶媒の寿命
を長くするには反応温度を低下させることが好ましいが
、（１）式で示される反応を短時間で完全に進行させる
には２００℃以上の温度が必要であるとされている。し
かし、温度を上げすぎると生成したＣＡがアンモニアと
反応し、却ってＣＡの収率が低下する。However, when the solvent is heated at high temperature for a long time in an atmosphere where ammonia gas is generated, the solvent partially deteriorates. Therefore, in order to extend the life of the solvent, it is preferable to lower the reaction temperature, but it is said that a temperature of 200°C or higher is required to allow the reaction represented by equation (1) to proceed completely in a short time. . However, if the temperature is raised too much, the generated CA will react with ammonia, and the yield of CA will actually decrease.
そこで本発明者らは、上記の方法において反応温度を従
来より低下させる方法について鋭意研究した。その結果
、特定の化合物を共存させることにより反応温度を従来
より低くしても、ＣＡが短時間でほぼ定量的に得られ、
かつＣＡとアンモニアとの反応もほとんど生じないこと
を見出し、本発明を完成した。Therefore, the present inventors have conducted intensive research into a method for lowering the reaction temperature in the above method compared to the conventional method. As a result, even if the reaction temperature is lower than before by coexisting a specific compound, CA can be obtained almost quantitatively in a short time,
Furthermore, they found that almost no reaction occurs between CA and ammonia, and completed the present invention.
即ち、本発明は、尿素を有機溶媒中でアルカリ金属水素
化物、アルカリ金属アミド化物又はイソシアヌル酸のア
ルカリ金属塩（以下、これらを単にアルカリ金属化合物
ともいう。）の存在下に加熱することを特徴とするイソ
シアヌル酸の製造法である。That is, the present invention is characterized in that urea is heated in an organic solvent in the presence of an alkali metal hydride, an alkali metal amide, or an alkali metal salt of isocyanuric acid (hereinafter also simply referred to as an alkali metal compound). This is a method for producing isocyanuric acid.
本発明において用いられる有機溶媒は、イソシアヌル酸
の製造反応温度、一般には１００℃以上で液体であり、
アルカリ金属化合物の１種類もしくは２種類以上を溶解
させ、かつ、それ自身が反応しないものであれば公知の
ものが何ら制限されずに使用し得る。有機溶媒として好
適な化合物としては例えば、エチレングリコールジメチ
ルエーテル、ジエチレングリコールジメチルエーテル、
トリエチレングリコールジメチルエーテル、テトラエチ
レングリコールジメチルエーテルなどのポリエチレング
リコールジメチルエーテル類；２−メチルピロリドン、
２，４−ジメチルピロリドン、２，２，４−トリメチル
ピロリドン、２−シクロヘキシルピロリドン、２−シク
ロヘキシル−４−メチルピロリドン、２−シクロヘキシ
ル−４，４−ジメチルピロリドンなとのピロリドン誘導
体類；ジメチルスルホキシド、Ｎ，Ｎ−ジメチルホルム
アミドなどがある。The organic solvent used in the present invention is liquid at the isocyanuric acid production reaction temperature, generally 100°C or higher,
Any known alkali metal compound can be used without any restriction as long as it dissolves one or more alkali metal compounds and does not react itself. Examples of compounds suitable as organic solvents include ethylene glycol dimethyl ether, diethylene glycol dimethyl ether,
Polyethylene glycol dimethyl ethers such as triethylene glycol dimethyl ether and tetraethylene glycol dimethyl ether; 2-methylpyrrolidone,
pyrrolidone derivatives such as 2,4-dimethylpyrrolidone, 2,2,4-trimethylpyrrolidone, 2-cyclohexylpyrrolidone, 2-cyclohexyl-4-methylpyrrolidone, 2-cyclohexyl-4,4-dimethylpyrrolidone; dimethylsulfoxide; Examples include N,N-dimethylformamide.
上記の有機溶媒の使用量は、特に制限されないが、得ら
れるＣＡの収率を勘案すると、尿素の濃度が１〜９０重
量％の範囲となるように選ぶことが好ましい。The amount of the organic solvent to be used is not particularly limited, but considering the yield of CA obtained, it is preferably selected so that the concentration of urea is in the range of 1 to 90% by weight.
次に、アルカリ金属水素化物は、水素化リチウム、水素
化ナトリウム、水素化カリウムが挙げられ、アルカリ金
属アミド化物は、リチウムアミド、ナトリウムアミド、
カリウムアミドが挙げられ、イソシアヌル酸のアルカリ
金属塩は、イソシアヌル酸のモノリチウム塩、ジリチウ
ム塩、トリリチウム塩、モノナトリウム塩、ジナトリウ
ム塩、トリナトリウム塩、モノカリウム塩、ジカリウム
塩、トリカリウム塩等が挙げられる。これらの中でもＣ
Ａの収率を高くするためには、ナトリウム化合物を用い
ることが好ましい。Next, examples of alkali metal hydrides include lithium hydride, sodium hydride, and potassium hydride, and examples of alkali metal amidides include lithium amide, sodium amide,
Alkali metal salts of isocyanuric acid include monolithium salt, dilithium salt, trilithium salt, monosodium salt, disodium salt, trisodium salt, monopotassium salt, dipotassium salt, tripotassium salt of isocyanuric acid. etc. Among these, C
In order to increase the yield of A, it is preferable to use a sodium compound.
これらのアルカリ金属化合物の使用量は、ＣＡを高収率
で得るためには尿素に対してモル比で１／１〜１／１０
００の範囲であることが好ましく、更には１／１０〜１
／４０であることがより好ましい。有機溶媒、尿素、及
びアルカリ金属化合物の導入順序は特に限定されない。The amount of these alkali metal compounds to be used is 1/1 to 1/10 in molar ratio to urea in order to obtain CA in high yield.
The range is preferably 00, more preferably 1/10 to 1
/40 is more preferable. The order of introduction of the organic solvent, urea, and alkali metal compound is not particularly limited.
反応温度は、前記（１）式の反応を進行させて、且つ生
成するＣＡの分解を防止するためには好ましくは１００
℃〜３０００℃の範囲で、更に好ましくは１５０℃〜２
００℃である。反応時間は好ましくは１０分間以上で、
更に好ましくは１時間以上である。The reaction temperature is preferably 100 ℃ in order to advance the reaction of the above formula (1) and prevent the decomposition of the generated CA.
℃~3000℃, more preferably 150℃~2
It is 00℃. The reaction time is preferably 10 minutes or more,
More preferably, the time is 1 hour or more.
（効果）
本発明の方法によれば、従来法より反応温度を５０℃以
上下げることができる。これにより、エネルギーコスト
を低減させることができ、また、溶媒の寿命を延ばすこ
とができる。(Effects) According to the method of the present invention, the reaction temperature can be lowered by 50° C. or more compared to the conventional method. This can reduce energy costs and extend the life of the solvent.
（実施例）
実施例１
容量３００ｍｌの三っ口フラスコに溶媒としてテトラエ
チレングリコールジメチルエーテルを１００ｇ入れ、１
５０℃に加熱し、攪拌しながら、尿素１０ｇ及び尿素に
対し１／４０モル量の水素化ナトリウムを添加した。５
時間１５０℃で攪拌を続けた。(Example) Example 1 Put 100g of tetraethylene glycol dimethyl ether as a solvent into a 300ml three-neck flask, and add 100g of tetraethylene glycol dimethyl ether as a solvent.
While heating to 50° C. and stirring, 10 g of urea and 1/40 molar amount of sodium hydride based on urea were added. 5
Stirring was continued at 150°C for an hour.
その後、室温まで冷却し生じた沈殿物を濾取した。Thereafter, the mixture was cooled to room temperature and the resulting precipitate was collected by filtration.
また、濾液から溶媒を留去すると固体が得られた。Further, a solid was obtained when the solvent was distilled off from the filtrate.
この沈殿物と濾液から得られた固体はそれぞれ６．１０
ｇ及び１．００ｇであった。元素分析、赤外線吸収スペ
クトル及び質量分析からどちらもＣＡと同定した。また
収率は両者あわせて９９％であった。The solids obtained from this precipitate and filtrate were each 6.10
g and 1.00 g. Both were identified as CA from elemental analysis, infrared absorption spectrum, and mass spectrometry. The total yield was 99%.
比較例１
水素化ナトリウムを加えないこと以外実施例１と同様に
反応を行った結果、沈殿物と濾液から得られた固体はそ
れぞれ３．５０ｇ及び４．５５ｇであった。実施例１と
同様にしてこれらの分析を行った結果、尿素、ビウレッ
ト、トリウレットの混合物で、まったくＣＡは含まれて
いなかった。Comparative Example 1 The reaction was carried out in the same manner as in Example 1 except that sodium hydride was not added. As a result, the solids obtained from the precipitate and the filtrate were 3.50 g and 4.55 g, respectively. These analyzes were carried out in the same manner as in Example 1, and the result was that it was a mixture of urea, biuret, and triuret, and contained no CA at all.
比較例２
水素化ナトリウムを用いず、温度を２００℃にして反応
を行なったこと以外は実施例１と同様にして反応を行な
った。その結果、尿素の添加率は９６％であり、ＣＡの
選択率は９９％であった。Comparative Example 2 A reaction was carried out in the same manner as in Example 1, except that sodium hydride was not used and the reaction was carried out at a temperature of 200°C. As a result, the urea addition rate was 96% and the CA selectivity was 99%.
実施例２
溶媒に２−シクロヘキシルピロリドンを用いること以外
は実施例１と同様に反応を行なった。尿素の転化率は９
７％でＣＡの選択率は９９％であった。Example 2 The reaction was carried out in the same manner as in Example 1 except that 2-cyclohexylpyrrolidone was used as the solvent. The conversion rate of urea is 9
7% and the selectivity of CA was 99%.
実施例３
表１で示したアルカリ金属化合物を用いること以外は実
施例１と同様に反応を行なった。結果は表１の通りであ
った。Example 3 The reaction was carried out in the same manner as in Example 1 except that the alkali metal compounds shown in Table 1 were used. The results are shown in Table 1.
Claims (1)
属アミド化物又はイソシアヌル酸のアルカリ金属塩の存
在下に加熱することを特徴とするイソシアヌル酸の製造
法。A method for producing isocyanuric acid, which comprises heating urea in an organic solvent in the presence of an alkali metal hydride, an alkali metal amide, or an alkali metal salt of isocyanuric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30699990A JP2915132B2 (en) | 1990-11-15 | 1990-11-15 | Method for producing isocyanuric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30699990A JP2915132B2 (en) | 1990-11-15 | 1990-11-15 | Method for producing isocyanuric acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04364173A true JPH04364173A (en) | 1992-12-16 |
| JP2915132B2 JP2915132B2 (en) | 1999-07-05 |
Family
ID=17963798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30699990A Expired - Fee Related JP2915132B2 (en) | 1990-11-15 | 1990-11-15 | Method for producing isocyanuric acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2915132B2 (en) |
-
1990
- 1990-11-15 JP JP30699990A patent/JP2915132B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2915132B2 (en) | 1999-07-05 |
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| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |