KR950001703B1 - Method for preparing trialkyl phosphate - Google Patents
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- KR950001703B1 KR950001703B1 KR1019910024647A KR910024647A KR950001703B1 KR 950001703 B1 KR950001703 B1 KR 950001703B1 KR 1019910024647 A KR1019910024647 A KR 1019910024647A KR 910024647 A KR910024647 A KR 910024647A KR 950001703 B1 KR950001703 B1 KR 950001703B1
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
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Abstract
내용없음.None.
Description
본 발명은 폴리머(polymer)중합촉매, 착색방지제 등의 용도로 널리 이용되고 있는 트리알킬포수페이트를 2상(2 phase)반응을 이용하여 간단하고 경제상있게 제조하는데 방법에 관한 것이다.The present invention relates to a method for producing trialkylphosphorate, which is widely used in polymer polymerization catalysts, anti-coloring agents and the like, simply and economically using a two-phase reaction.
종래의 기술인 일본특허공고 소52-42779에 의하면, 가성소다를 알킬알코올에 용해시킨후 저온(-5-5。C)에서 옥시염화인을 적가시키고 순수한 물을 참가하고 다시 클로로포름을 첨가하여 교반한후 클로로포름층을 분리하여 감압증류로써 트리알킬포스페이트를 제조한다.According to the prior art Japanese Patent Publication No. 52-42779, caustic soda is dissolved in alkyl alcohol, and then phosphorus oxychloride is added dropwise at low temperature (-5-5 ° C), pure water is added, and chloroform is added again and stirred. After separating the chloroform layer to prepare a trialkyl phosphate by distillation under reduced pressure.
그러나 이 방법은 가성소다를 알코올에 용해시켜 사용하기 때문에, 가성소다와 발생되는 염화수소가스가 직접반응하므로 강산과 강염기의 반응열이 상당히 발생하여 저온반응의 유지를 위한 냉각설비의 효율이 떨어지며 적가시간이 길어진다.However, since this method uses caustic soda in alcohol, the caustic soda and hydrogen chloride gas are directly reacted, so the heat of reaction between strong acid and strong base is generated considerably. Longer
또한 알코올에 대한 염기의 용해도 때문에 가성소다 이외의 염기를 사용하기 곤란하며, 적가후에 다시 순수 H2O와 클로로포름을 첨가하여야 하는 번거로움이 있다.In addition, due to the solubility of the base in alcohol, it is difficult to use a base other than caustic soda, and it is troublesome to add pure H 2 O and chloroform again after the addition.
또한 반응시 염화수소개스와 가성소다의 반응에 의한 염화나트륨의 염의 고체로 생성되므로 교반에 지장을 주는 단점이 있다.In addition, since the reaction is produced as a solid of the salt of sodium chloride by the reaction of the introduction of sodium chloride and caustic soda, there is a disadvantage that the stirring.
일반적으로 옥시염화인과 물과의 반응이 상당히 빠른 것으로 알려져있으나 실제로는 그렇게 쉽게 반응, 분해되지 않으며, 또한 옥시염화인과 물과의 반응보다 반응속도가 빠른 타반응이 동시에 진행될 경우 타반응이 더 잘 진행됨을 알 수 있다.In general, it is known that the reaction between phosphorus oxychloride and water is considerably faster, but in reality, it is not so easily reacted and decomposed. You can see that it goes well.
따라서 이를 이용하여 트리알킬포스페이트를 제조함에 있어서 가장 문제점이 되고 있는 염화수소개스를 수용액의 염기를 이용하여 제거하고, 또한 반응물을 유기용매층에 녹인후 반응목적물과부반응물질인 염(salt)을 분리하여 반응목적물을 감압증류를 실시하여 경제적이고 고수율로 제조하는 것이 본 발명의 내용이다.Therefore, by using this, the most problematic problem in the preparation of trialkyl phosphate is to remove the introduction of aqueous chloride using the base of the aqueous solution, and also to dissolve the reactants in the organic solvent layer and to separate the reaction targets and salts (side salts) It is the content of the present invention to produce the reaction object economically and in high yield by performing distillation under reduced pressure.
트리알킬포스페이트를 제조하는 방법은 여러가지 알려져 있으나 가장 큰 관점은 염화수소개스의 제거방법으로서, 이는 옥시염화인으로 제조시 옥시염화인 1몰당 3몰의 염화수소개스가 발생되며 이 염화수소개스에 의하여 트리알킬포스페이트가 분해되어 (반응식 1) 수율이 낮아지는 원인이 되며 또한 염화수소개스 제거를 위한 설비의 보완으로 원가가 높아지고 근본원인이 된다.There are various known methods for preparing trialkyl phosphate, but the biggest aspect is the method of removing chlorofluorocarbons, which is 3 moles of hydrochloric acid per mole of phosphorus oxychloride when prepared with phosphorus oxychloride, and the trialkylphosphate Is decomposed (Scheme 1), which lowers the yield, and the cost increases and becomes the root cause by supplementing the facility for the removal of hydrochloric acid.
이때 염화수소개스를 제거하는 방법중 염기를 사용하는 방법은 여러가지 있으나 대부분 산·염기반응으로 인한 반응열의 발생과 생성된 염의 제거로 인한 어려움이 있어 많이 사용되지 않으며, 진공으로써 과량 사용된 알코올의 잔여분과 염화수소개스를 제거하는 방법이 널리 이용되거나 이는 설비의 보완 등이 필요하며 온도가 조금만 높을 경우 분해가 많이 일어나는 단점이있다.At this time, there are various methods of using base among the methods of removing the introduction of hydrochloric acid, but most of them are difficult to use due to the generation of heat of reaction due to acid and base reactions and the removal of generated salts. The method of removing the introduction of hydrochloric acid is widely used or this requires the supplementation of equipment and the disadvantage that a lot of decomposition occurs when the temperature is a little high.
따라서 염화수소개스를 효과적으로 제거하는 것이 중요하다는 관점에서 본 발명에서는 2상(phase)에서 옥시염화인을 적가시켜 알코올과 옥시염화인을 반응시키고 발생되는 염화수소개스는 물층의 염기로써 제거하고 곧바로 분리하므로 공정이 단순하며 유기용매의 완충작용으로 발생열이 작아 온도조절이 쉽고 물에 녹는 모든 염기를 사용할 수 있는 특징이있다.Therefore, in view of the importance of effectively removing hydrochloric acid, in the present invention, by adding dropwise phosphorus oxychloride in two phases, alcohol and phosphorus oxychloride are reacted, and the generated hydrochloric acid is removed as a base of the water layer and immediately separated. This simple, low heat generated by the buffering effect of the organic solvent is easy to control the temperature, it is characterized by the use of all bases soluble in water.
2상(phase)상태에서 옥시염화인을 적가시키는 경우를 자세히 살펴보면 다음과 같다.The case of dropwise addition of phosphorus oxychloride in the two-phase state is as follows.
H2O층과 유기용매가 서로 섞이거나 용해되지 않으므로 여기에 옥시염화인을 적가하면 알코올과 옥시염화인이 반응하여 생성되는 트리알킬포스페이트는 유기용매층으로 녹고 발생되는 염화수소가스는 염기에 의해 중화되어 물층에 녹으므로 반응후 층분리에 의하여 목적물질을 얻을 수 있다.Since the H 2 O layer and the organic solvent do not mix or dissolve with each other, when phosphorus oxychloride is added dropwise, trialkyl phosphate produced by the reaction of alcohol and phosphorus oxychloride is dissolved into the organic solvent layer, and the generated hydrogen chloride gas is neutralized with a base. Because it is dissolved in the water layer can be obtained by the separation of the target material after the reaction.
본 발명의 제조방법은 다음과 같다.The production method of the present invention is as follows.
먼저 염기를 순수한 물에 용해시킨후 반응기 안에 투입한다.The base is first dissolved in pure water and then introduced into the reactor.
이때 염기는 가성소다, 탄산칼륨, 탄산나트륨, 탄산수소나트륨, 탄산수소칼륨 등 고체염기를 사용하며 필요시에는 반응기 안에 순수한 물과 염기를 같이 넣어 용해시킨후 다음 반응을 진행시켜도 무방하지만 용해열로 인한 온도의 상승이 있으므로 온도조절에 어려움이 있다.The base is a solid base such as caustic soda, potassium carbonate, sodium carbonate, sodium bicarbonate, potassium hydrogen carbonate, etc. If necessary, pure water and base can be added together to dissolve and proceed with the next reaction. There is a rise in the temperature control is difficult.
이때 염기의 양은 옥시염화인 대비 2.5-5몰 사용한다.At this time, the amount of the base is used 2.5-5 mol relative to the phosphorus oxychloride.
여기에 유기용매를 투입하는데 유기용매는 물과 섞이지 않는, 반응성이 적은 대부분의 용매를 사용할 수 있지만 본 발명서에서는 에틸렌디클로라이드, 클로로포름, 클로로벤젠, 사염화탄소, 톨루엔, 벤젠 등을 사용한다. 이때 물과 유기용매의 비는 1 : 3-3 : 1을 사용하며 전체량은 알코올의 1-10배를 사용한다.The organic solvent may be added to the organic solvent, but most of the solvent which is not mixed with water may be used, but in the present invention, ethylene dichloride, chloroform, chlorobenzene, carbon tetrachloride, toluene, benzene and the like are used. At this time, the ratio of water and organic solvent is 1: 3-3: 1 and the total amount is 1-10 times of alcohol.
같은 반응기 안에 다시 반응 시키고자하는 알킬알코올을 투입하며, 이때 알킬알코올은 메틸알코올, 에틸알코올, 노말-프로필알코올, 이소프로필알코올, t-부틸알코올, 옥틸 알코올 등을 사용하며 알코올의 양은 옥시염화인대비 3-15몰이 적당하며 3.5-6몰을 사용하였을 때 가장 좋은 효과를 얻을 수 있다.Alkyl alcohol to be reacted in the same reactor is added again, wherein alkyl alcohol is methyl alcohol, ethyl alcohol, normal-propyl alcohol, isopropyl alcohol, t-butyl alcohol, octyl alcohol, and the amount of alcohol is phosphorus oxychloride. 3-15 moles is suitable for the comparison and the best effect can be obtained when 3.5-6 moles are used.
투입이 모두 끝난후 옥시염화인을 서서히 적가하며 이때 온도는 0-50。C를 유지해야 하는데 0-15。C가 가장 효과적이다.Phosphorus oxychloride is slowly added dropwise after the addition, and the temperature should be maintained at 0-50 ° C. 0-15 ° C is most effective.
옥시염화인의 적가가 끝난후 20-30분동안 더 반응을 시킨후 층분리를 실시한다.After the dropwise addition of phosphorus oxychloride, the solution is further reacted for 20-30 minutes and then separated.
이때 유기층에는 트리알킬포스페이트가 들어있으므로 반응의 공정상 비중이 낮은 유기용매를 써서 유기용매층이 상층이 되도록 하여 하층인 물층을 제거하는 것이 편리하다.At this time, since the trialkyl phosphate is contained in the organic layer, it is convenient to remove the lower water layer by using the organic solvent having a low specific gravity in the process of reaction so that the organic solvent layer becomes the upper layer.
물층을 제거하고 남은 유기용매층은 감압증류로써 유기용매를 회수하고 목적물질인 트리알킬포스페이트를 얻으며 이때 수율은 알코올의 종류에 따라 다르나 80% 이상의 높은 수율로 얻어진다.After removing the water layer, the remaining organic solvent layer recovers the organic solvent by distillation under reduced pressure to obtain trialkyl phosphate as a target substance. The yield varies depending on the type of alcohol, but is obtained in a high yield of 80% or more.
감압증류의 조건은 진공의 정도가 높을수록 좋으며 일반적으로 0.1-100mmHg가 적당하다.The higher the degree of vacuum, the better the conditions for distillation under reduced pressure. Generally, 0.1-100 mmHg is appropriate.
알코올을 옥시염화인 대비 3-15몰 투입하는 이유는 3몰 미만인 경우에는 POCl3의 Cl이 알코올로 치환되어야 하는데 이 경우 반응이 완전히 진행되지 않으며, 15몰 이상인 경우에는 반응상의 문제점은 없으나 원가상승 및 작업의 효율성(through-put)이 떨어진다.The reason why 3-15 moles of alcohol is added to phosphorus oxychloride is that when Cl is less than 3 moles, Cl of POCl 3 should be replaced with alcohol. In this case, the reaction does not proceed completely. And inefficient throughput.
염기량은 2.5 - 5몰 사용하는데 이유는 2.5몰보다 적을 경우는 발생되는 염화수소개스(옥시염화인 1몰당 3몰발생)를 완전히 중화하지 못하여 목적물질이 HCl가스에 의해 분해될 가능성이 높으며, 과량 사용시는 원가 상승 및 용해도 차이에 의한 분리시 문제점이 있다.The base amount is 2.5-5 moles. The reason is that if the amount is less than 2.5 moles, it is not possible to completely neutralize the hydrogen chloride (3 moles per mole of phosphorus oxychloride) that is likely to be decomposed by HCl gas. In use, there are problems in separation due to cost increase and solubility difference.
물과 유기용매의 전체량은 알코올 대비 1-10배/중량% 사용한다.The total amount of water and organic solvent is used 1-10 times / weight% compared to alcohol.
적정량 미만 사용시는 염화나트륨염 및 수산화나트륨 등의 염기를 다 녹이지 못하여 분리가 곤란하며 과량사용시는 작업의 효율성(through-put)이 낮아진다.If it is used in an appropriate amount, it is difficult to separate the base such as sodium chloride salt and sodium hydroxide, so it is difficult to separate it.
진공 0.1-200mmHg으로 하는 이유는 상압은 760mmHg이고 진공은 압력을 낮추는 것인데, 이때 진공도 가 높을수록 끓는 점이 낮아진다. 따라서 200mmHg 이상인 경우 감압증류의 의미가 없다.The reason for the vacuum of 0.1-200mmHg is that the atmospheric pressure is 760mmHg and the vacuum lowers the pressure. At this time, the higher the degree of vacuum, the lower the boiling point. Therefore, if it is more than 200mmHg, there is no meaning of vacuum distillation.
적가온도를 0-50。C로 하는 이유는 일반적으로 온도가 높을 경우 반응물이 분해될 가능성이 높으며 온도가 낮을 경우 반응의 진행도가 낮아진다.The reason why the dropping temperature is 0-50 ° C is generally that the reaction is more likely to decompose when the temperature is high and the progress of the reaction is low when the temperature is low.
다음에 실시예로서 본 발명을 더욱 상세히 설명한다.Next, the present invention will be described in more detail by way of examples.
[비교예(일본특허공고 소52-42779)][Comparative Example (Japanese Patent Publication No. 52-42779)]
가성소다 128.0g(3.2몰)을 메탄올 320.0g(10.0몰)에 용해시키고 반응온도 -5-5。C에서 옥시염화인 153.5g(1.0몰) 적가 시켰다.128.0 g (3.2 mol) of caustic soda was dissolved in 320.0 g (10.0 mol) of methanol, and 153.5 g (1.0 mol) of phosphorus oxychloride was added dropwise at a reaction temperature of -5-5 ° C.
반응이 끝난후 15분간 더 교반하고 물 450g을 첨가하여 발생된 염을 모두 녹인후 클로로포름 800ml를 첨가하여 추출하였다. 잔여물을 83-85。C/20mmHg에서 감압증류하여 트리메틸포스페이트 119.2g(수율 85.0%)을 얻었다.After completion of the reaction, the mixture was further stirred for 15 minutes, 450 g of water was added to dissolve all the salts, and 800 ml of chloroform was added thereto. The residue was distilled under reduced pressure at 83-85 ° C./20 mmHg to give 119.2 g (yield 85.0%) of trimethylphosphate.
[실시예1]Example 1
트리메틸포스페이트의 제조Preparation of Trimethyl Phosphate
가성소다 40g(1몰)을 순수한 물 200ml에 녹인후 반응기 안에 투입시키고 에틸렌디클로라이드 200ml와 메틸알코올 80g(2.5몰)을 투입하였다.40 g (1 mol) of caustic soda was dissolved in 200 ml of pure water, and then charged into a reactor, and 200 ml of ethylene dichloride and 80 g (2.5 mol) of methyl alcohol were added thereto.
10-15。C를 유지하면서 옥시염화인 48g(0.3125몰)을 서서히 저가시켰다.48 g (0.3125 mol) of phosphorus oxychloride was slowly lowered while maintaining 10-15 ° C.
적가가 끝난후 20분간 더 교반시키고 층분리를 실시하여 하층의 물층을 제거하고 잔여물을 진공증류하여 83-85。C/20mmHg에서 트리메틸포스페이트를 40.0g(수율 91.4%) 얻었다.After completion of the dropwise addition, the mixture was further stirred for 20 minutes and the layers were separated to remove the lower water layer, and the residue was distilled under vacuum to obtain 40.0 g (yield 91.4%) of trimethylphosphate at 83-85 ° C / 20mmHg.
[실시예2]Example 2
트리에틸포스페이트의 제조Preparation of Triethyl Phosphate
실시예 1의 메탄올 대신 에탄올을 사용하여 같은 방법으로 트리에틸포스페이트 47.25(수율 84.2%)을 얻었다.Triethylphosphate 47.25 (yield 84.2%) was obtained in the same manner using ethanol instead of methanol in Example 1.
[실시예3]Example 3
트리이소프로필포스페이트의 제조Preparation of Triisopropyl Phosphate
실시예 1의 메탄올 대신 이소프로필 알코올을 사용하여 같은 방법으로 트리이소프로필포스페이트 54.7g(수율 80.3%)을 얻었다.54.7 g (yield 80.3%) of triisopropylphosphates were obtained by the same method using isopropyl alcohol instead of methanol of Example 1.
[실시예4]Example 4
트리메틸포스페이트의 제조Preparation of Trimethyl Phosphate
실시예 1의 가성소다 대신 탄산칼륨을 같은 몰의 양을 사용하여 같은 방법으로 트리메틸포스페이트 37.6g(수율 86.0%)을 얻었다.Instead of caustic soda of Example 1, 37.6 g (yield 86.0%) of trimethylphosphate was obtained in the same manner using the same molar amount of potassium carbonate.
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019910024647A KR950001703B1 (en) | 1991-12-27 | 1991-12-27 | Method for preparing trialkyl phosphate |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019910024647A KR950001703B1 (en) | 1991-12-27 | 1991-12-27 | Method for preparing trialkyl phosphate |
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| Publication Number | Publication Date |
|---|---|
| KR930012796A KR930012796A (en) | 1993-07-21 |
| KR950001703B1 true KR950001703B1 (en) | 1995-02-28 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR1019910024647A Expired - Fee Related KR950001703B1 (en) | 1991-12-27 | 1991-12-27 | Method for preparing trialkyl phosphate |
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| Country | Link |
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| KR (1) | KR950001703B1 (en) |
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| KR930012796A (en) | 1993-07-21 |
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