KR101863126B1 - Process for purification of 2,6-dimethylphenol by azeotropic distillation - Google Patents
Process for purification of 2,6-dimethylphenol by azeotropic distillation Download PDFInfo
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- KR101863126B1 KR101863126B1 KR1020120010390A KR20120010390A KR101863126B1 KR 101863126 B1 KR101863126 B1 KR 101863126B1 KR 1020120010390 A KR1020120010390 A KR 1020120010390A KR 20120010390 A KR20120010390 A KR 20120010390A KR 101863126 B1 KR101863126 B1 KR 101863126B1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C37/78—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/36—Azeotropic distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/88—Use of additives, e.g. for stabilisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/06—Alkylated phenols
- C07C39/07—Alkylated phenols containing only methyl groups, e.g. cresols, xylenols
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Abstract
본 발명은 o-크레졸을 포함하는 조 2,6-디메틸페놀의 혼합물로부터 공비제를 사용하여 공비증류를 통해 2,6-디메틸페놀을 정제하는 방법으로서, 상기 공비제로 끓는점이 155 내지 170℃의 탄화수소 공비제를 사용하여 공비증류를 통해 o-크레졸을 탄화수소 공비제와 공비물 또는 공비혼합물로서 제거하여 2,6-디메틸페놀을 정제하는 방법에 관한 것이다.The present invention relates to a process for purifying 2,6-dimethylphenol by azeotropic distillation from a mixture of crude 2,6-dimethylphenol containing o-cresol using an azeotropic agent, wherein the azeotrope has a boiling point of from 155 to 170 ° C And removing o-cresol as an azeotropic agent or an azeotropic mixture through azeotropic distillation using a hydrocarbon azeotropic agent to purify 2,6-dimethylphenol.
Description
본 발명은 o-크레졸을 포함하는 조 2,6-디메틸페놀의 혼합물로부터 공비제를 사용하여 공비증류를 통해 2,6-디메틸페놀을 정제하는 방법으로서, 상기 공비제로 끓는점이 155 내지 170℃의 탄화수소 공비제를 사용하여 공비증류를 통해 o-크레졸을 탄화수소 공비제와 공비물 또는 공비혼합물로서 제거하여 2,6-디메틸페놀을 정제하는 방법에 관한 것이다.
The present invention relates to a process for purifying 2,6-dimethylphenol by azeotropic distillation from a mixture of crude 2,6-dimethylphenol containing o-cresol using an azeotropic agent, wherein the azeotrope has a boiling point of from 155 to 170 ° C And removing o-cresol as an azeotropic agent or an azeotropic mixture through azeotropic distillation using a hydrocarbon azeotropic agent to purify 2,6-dimethylphenol.
크레졸 아이소머의 혼합물, 크레졸과 2,6-디메틸페놀의 혼합물, 및 이들을 포함한 알킬페놀의 혼합물을 분리하기 위하여 증류, 결정화, 추출, 흡착 또는 이들의 조합 등 다양한 방법이 제안되었다.Various methods have been proposed for distillation, crystallization, extraction, adsorption, or a combination thereof to separate a mixture of cresol isomers, a mixture of cresol and 2,6-dimethylphenol, and a mixture of alkylphenols including them.
예시된 방법 중, 결정화, 추출 및 흡착은 분리과정이 복합하고, 분리된 크레졸의 효율이 낮아 상업적으로 효과적이지 않다. o-크레졸, m-크레졸 및 p-크레졸의 혼합물과 같이 유사비점을 가지는 적어도 두 개의 알킬페놀의 혼합물 또는 페놀, o-크레졸, p-크레졸, 2,4-디메틸페놀 및 2,6-디메틸페놀을 포함하는 페놀 또는 크레졸의 메틸화 생성물의 혼합물로부터 끓는점이 높은 알킬페놀과 끓는점이 낮은 알킬페놀을 분리하는데 있어서, 다수의 이론단수를 갖는 정류탑이 요구되고, 증류는 높은 환류비에서 수행되어야 한다. 게다가, 이러한 단점 이외에도 이러한 분리 과정은 필요로 한 열의 양 및 증류 속도에 대하여 단점도 가지고 있다.
Among the exemplified methods, crystallization, extraction and adsorption are not commercially effective due to the complexity of the separation process and the low efficiency of the separated cresol. a mixture of at least two alkylphenols having similar boiling points, such as a mixture of o-cresol, m-cresol and p-cresol, or a mixture of phenol, o-cresol, p-cresol, 2,4-dimethylphenol and 2,6- In order to separate alkylphenols with high boiling points from alkylphenols with low boiling points from a mixture of phenol or cresol methylated products, distillation must be carried out at a high reflux ratio. Moreover, apart from these drawbacks, this separation process also has drawbacks in terms of the amount of heat required and the rate of distillation.
본 발명의 목적은 o-크레졸을 포함하는 조 2,6-디메틸페놀의 혼합물로부터 공비제로 끓는점이 155 내지 170℃의 탄화수소 공비제를 사용하여 공비증류를 통해 o-크레졸을 탄화수소 공비제와 공비물 또는 공비혼합물로서 제거하여 2,6-디메틸페놀을 정제하는 방법을 제공하는 것이다.
The object of the present invention is to provide a process for the preparation of o-cresol from a mixture of crude 2,6-dimethylphenol containing o-cresol by azeotropic distillation using an azeotropic hydrocarbon azeotrope having a boiling point of 155-170 & Or as an azeotropic mixture, thereby purifying 2,6-dimethylphenol.
본 발명은 o-크레졸을 포함하는 조 2,6-디메틸페놀의 혼합물로부터 공비제를 사용하여 공비증류를 통해 2,6-디메틸페놀을 정제하는 방법으로서, 상기 공비제로 끓는점이 155 내지 170℃의 탄화수소 공비제를 사용하여 공비증류를 통해 o-크레졸을 탄화수소 공비제와 공비물 또는 공비혼합물로서 제거하여 2,6-디메틸페놀을 정제하는 방법에 관한 것이다.The present invention relates to a process for purifying 2,6-dimethylphenol by azeotropic distillation from a mixture of crude 2,6-dimethylphenol containing o-cresol using an azeotropic agent, wherein the azeotrope has a boiling point of from 155 to 170 ° C And removing o-cresol as an azeotropic agent or an azeotropic mixture through azeotropic distillation using a hydrocarbon azeotropic agent to purify 2,6-dimethylphenol.
본 발명의 탄화수소 공비제는 상압에서 155 내지 170℃의 끓는점을 갖는 탄화수소 화합물 또는 그들의 혼합물로, 고비점의 탄화수소 공비제를 별도의 정제 과정을 거쳐 155 내지 170℃의 끓는점을 가지는 탄화수소 화합물 또는 그들의 혼합물을 분리하여 사용한다. 상기 상업적으로 판매중인 고비점의 탄화수소 공비제는 155 내지 170℃의 끓는점을 갖는 탄화수소 화합물을 30% 이상, 좋게는 60% 이상, 더욱 좋게는 95% 이상 포함하고 있다.The hydrocarbon azeotropic agent of the present invention is a hydrocarbon compound having a boiling point at atmospheric pressure ranging from 155 to 170 DEG C or a mixture thereof. The hydrocarbon azeotrope having a high boiling point is subjected to a separate purification process to obtain a hydrocarbon compound having a boiling point at 155 to 170 DEG C, . The commercial high boiling point hydrocarbon azeotropic agent contains 30% or more, preferably 60% or more, more preferably 95% or more, of a hydrocarbon compound having a boiling point of 155 to 170 ° C.
본 발명의 탄화수소 공비제는 조 2,6-디메틸페놀 100 중량부에 대하여 15 내지 50 중량부로 사용되는 것이 바람직하다.The hydrocarbon azeotropic agent of the present invention is preferably used in an amount of 15 to 50 parts by weight based on 100 parts by weight of crude 2,6-dimethylphenol.
본 발명의 탄화수소 공비제는 o-크레졸과 공비물 또는 공비혼합물을 형성하여 조 2,6-디메틸페놀로부터 o-크레졸을 공비혼합물의 형태로 제거시키는데 효과적이다.The hydrocarbon azeotropic agent of the present invention is effective for removing o-cresol from the crude 2,6-dimethylphenol in the form of an azeotropic mixture by forming an azeotropic mixture with o-cresol or an azeotropic mixture.
본 발명의 탄화수소 공비제를 사용하여 공비증류로 공비증류된 공비혼합물 형태로 손실되는 2,6-디메틸페놀의 양은 전체 조 2,6-디메틸페놀의 2중량% 미만이다.The amount of 2,6-dimethylphenol lost in the form of an azeotropic mixture azeotropically distilled azeotropically using the hydrocarbon azeotropic agent of the present invention is less than 2% by weight of the total crude 2,6-dimethylphenol.
본 발명의 탄화수소 공비제와 함께 다른 탄화수소 용매를 사용할 수 있으며, 탄화수소 용매는 탄화수소 공비제의 양보다 적게 사용하며, 바람직하게는 공비제의 무게에 비해 50% 미만으로 사용한다. Other hydrocarbon solvents may be used with the hydrocarbon azeotrope of the present invention, and the hydrocarbon solvent is used less than the amount of the hydrocarbon azeotropic agent, preferably less than 50% by weight of the azeotropic agent.
공비증류는 상압, 저압 또는 고압에서 실시될 수 있으나, 바람직하게는 상압에서 실시한다. The azeotropic distillation may be carried out at normal pressure, low pressure or high pressure, but preferably at normal pressure.
증류는 연속식 또는 회분식으로 실시될 수 있으나, 회분식으로 실시되는 것이 가장 바람직하다.
The distillation may be carried out continuously or batchwise, but most preferably is carried out batchwise.
본 발명에 따른 2,6-디메틸페놀의 정제방법을 사용하면, 기존 공법의 단점인 높은 2,6-디메틸페놀 손실 및 에너지 소모량, 높은 공비화합물 소모량, 불순물의 발생, 증류탑의 낮은 분리 효율 등을 제거하거나 최소화함으로서 고순도의 2,6-디메틸페놀을 얻을 수 있고 경제성을 더욱 높이는 효과를 기대할 수 있다.
The use of the method of purifying 2,6-dimethylphenol according to the present invention can provide a high level of 2,6-dimethylphenol loss and energy consumption, high azeotrope compound consumption, impurity generation, low separation efficiency of the distillation column, It is possible to obtain 2,6-dimethylphenol of high purity by removing or minimizing it, and it is expected that the economical efficiency is further increased.
이하에서는, 실시예를 통하여 본 발명을 더욱 상세하게 설명한다. 그러나, 본 발명의 범위가 하기의 실시예로 제한되는 것은 아니다.
Hereinafter, the present invention will be described in more detail with reference to examples. However, the scope of the present invention is not limited to the following examples.
[실시예 1][Example 1]
o-크레졸 2.7%를 함유하는 2,6-디메틸페놀 1100g에 제품명YK-MD40(SK종합화학)고비점의 탄화수소 공비제를 끓는점 155 ~ 170 ℃ 범위의 혼합물만 분별 증류하여 본 발명의 탄화수소 공비제로서 400g을 가하였다. 상기 혼합물을 2L 둥근바닥 플라스크에 넣고 30단 증류컬럼으로 상압 하에서 공비증류시켰다. 가열은 110V 히팅멘틀(heating mentle)을 이용하였으며, 입력 전압을 60~70V로 조정하여 운전하였다. 환류비는10:1로 설정하고 상부 증류온도별로 분획한 시료는 가스크로마토그래피로 분석하였다. 가스크로마토그래피 분석에는 HP-5컬럼을 이용하였으며, 내부표준법을 이용하여 분석하였다. 최종적으로는 둥근바닥 플라스크 내의 잔류 시료를 가스 크로마토그래피로 분석하여 탄화수소 공비제를 제외한 시료 중 o-크레졸의 함량이 0.2%미만인 경우 종료하였다. 그 결과를 하기 [표1]에 기재하였다. 이 방법의 경우 하기 비교예 1에 비해 분석의 효율성 및 잔여 공비제 제거 시 효율성이 증가하는 이점이 있다.
(SK Chemical) high boiling point hydrocarbon azeotropic agent at a boiling point in the range of 155 to 170 DEG C was fractionally distilled into 1100 g of 2,6-dimethylphenol containing 2.7% o-cresol to obtain the hydrocarbon azeotropic agent Was added. The mixture was placed in a 2 L round bottom flask and azeotropically distilled at atmospheric pressure into a 30 stage distillation column. Heating was performed using a 110V heating mentle and the input voltage was adjusted to 60 ~ 70V. The reflux ratio was set to 10: 1 and the fraction separated by the upper distillation temperature was analyzed by gas chromatography. For gas chromatographic analysis, HP-5 column was used and analyzed by internal standard method. Finally, the residual sample in the round bottom flask was analyzed by gas chromatography, and the sample was terminated when the content of o-cresol was less than 0.2% in the sample excluding the hydrocarbon azeotropic agent. The results are shown in Table 1 below. This method has an advantage that the efficiency of analysis and the efficiency of removing residual azeotropic agent are increased as compared with Comparative Example 1 below.
[비교예 1][Comparative Example 1]
고비점의 탄화수소 공비제(제품명YK-MD40, SK종합화학)를 그대로 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 공비증류를 실시하였다. 그 결과를 하기 [표1]에 기재하였다.
The azeotropic distillation was carried out in the same manner as in Example 1 except that the high boiling point hydrocarbon azeotropic agent (product name: YK-MD40, SK General Chemicals) was used as it was. The results are shown in Table 1 below.
[비교예 2][Comparative Example 2]
탄화수소 공비제를 사용하지 않는 것을 제외하고는 실시예 1과 동일한 방법으로 증류를 실시하였다. 그 결과를 하기 [표1]에 기재하였다.
Distillation was carried out in the same manner as in Example 1, except that the hydrocarbon azeotropic agent was not used. The results are shown in Table 1 below.
[표 1] [Table 1]
상기 표 1에서 상부 증류 온도는 탄화수소 공비제가 단일 물질이 아니므로, 공비제의 조성에 따라 지속적으로 변화하고 있다. 또한, 실시예 1의 경우 공비증류 후 공비제는 3~8 wt%포함되며, 이는 상기 공정 이후 1:10의 환류비에서 분별증류로 완전히 제거가능한 반면, 비교예 1의 경우 공비제를 정제하지 않고 그대로 사용하였기 때문에 잔류 공비제의 완전한 제거가 어렵다.In Table 1, the upper distillation temperature is continuously changing according to the composition of the azeotropic agent, since the hydrocarbon azeotropic agent is not a single substance. In the case of Example 1, after the azeotropic distillation, the azeotropic agent contained 3 to 8 wt%, which can be completely removed by fractional distillation at a reflux ratio of 1:10 after the above process, whereas in Comparative Example 1, It is difficult to completely remove the residual azeotropic agent.
상기 표 1의 결과로부터, 고비점의 탄화수소 공비제로부터 분별증류된 끓는점 155 ~ 170 ℃ 범위의 탄화수소 공비제를 이용한 실시예 1의 경우 2,6-디메틸페놀의 순도 99.8%에 도달하기까지 24시간이 걸렸으며 30단 증류컬럼의 상부 증류 온도 170℃에서 수득물의 조성을 살펴보면 2,6-디메틸페놀의 손실 정도는 1.9중량%인 반면, 고비점 탄화수소 공비제를 이용한 비교예 1의 경우 2,6-디메틸페놀의 순도 99.8%에 도달하기까지 시간은 17시간으로 단축되나 정제하고자 하는 2,6-디메틸페놀의 손실 정도가 5.8중량%로 매우 높아져 최종적으로 수득되는 순도 99.8%의 2,6-디메틸페놀의 수율이 감소되는 것을 알 수 있었다. From the results shown in the above Table 1, it can be seen that in the case of Example 1 using a hydrocarbon azeotropic agent having a boiling point of 155 to 170 DEG C fractionally distilled from a high boiling point hydrocarbon azeotropic agent, the purity of 2,6- When the composition of the product obtained at the upper distillation temperature of 170 ° C of the 30-stage distillation column was examined, the loss of 2,6-dimethylphenol was 1.9% by weight, whereas in Comparative Example 1 using the high boiling point hydrocarbon azeotropic agent, The time until the purity of the dimethylphenol reached 99.8% was shortened to 17 hours, but the degree of the loss of the 2,6-dimethylphenol to be purified was as high as 5.8% by weight, and the finally obtained purity of 99.8%, 2,6-dimethylphenol The yield of the catalyst was decreased.
또한, 상기 표 1의 결과로부터, 실시예 1의 경우 30단 증류컬럼의 상부에서 수득되는 증류 수득물의 조성 중 공비제의 함량이 90% 이상으로 반응기 내에 공비제가 거의 존재하지 않고 고순도의 2,6-디메틸페놀만이 남아있는 반면, 비교예 1의 경우 고비점의 공비제가 일부 제거되지 않은 채 반응기 내에 고순도의 2,6-디메틸페놀과 함께 존재하고 있어 고순도의 2,6-디메틸페놀을 제외한 고비점 공비제를 제거하기 위한 후처리 과정이 필수적이다.From the results of Table 1, it can be seen that, in the case of Example 1, the content of the azeotropic agent in the composition of the distillation product obtained at the upper part of the 30-stage distillation column is 90% or more, - dimethylphenol alone remained, whereas in Comparative Example 1, the high boiling point azeotropic agent was not removed and the reactor was present together with high purity 2,6-dimethylphenol, so that the high boiling point except for 2,6-dimethylphenol A post-treatment process for removing the point azeotropic agent is essential.
또한, 탄화수소 공비제를 사용하지 않은 비교예 2의 일반적인 증류로는 30단 증류컬럼으로 고순도의 2,6-디메틸페놀을 수득하는 것이 불가능하였다. In addition, it was impossible to obtain 2,6-dimethylphenol of high purity by a 30-stage distillation column as a general distillation column of Comparative Example 2 without using a hydrocarbon azeotropic agent.
즉, 본 발명에 따른 끓는점 155 ~ 170 ℃ 범위의 탄화수소 공비제를 이용한 2,6-디메틸페놀의 정제 방법은 2,6-디메틸페놀의 손실이 2중량% 미만으로 순도가 좋은 2,6-디메틸페놀을 높은 수율로 수득할 수 있다. 또한, 본 발명에 따른 상기 탄화수소 공비제를 이용한 경우 별도의 후처리과정 없이 고순도의 2,6-디메틸페놀을 수득할 수 있다.That is, the process for purifying 2,6-dimethylphenol using a hydrocarbon azeotropic agent having a boiling point in the range of 155 to 170 ° C according to the present invention is characterized in that 2,6-dimethylphenol has a loss of less than 2% Phenol can be obtained with high yield. In addition, when the hydrocarbon azeotropic agent according to the present invention is used, high purity 2,6-dimethylphenol can be obtained without a separate post-treatment.
Claims (6)
상기 공비제로 끓는점 155 내지 170℃의 탄화수소 혼합물의 공비제를 사용하는 2,6-디메틸페놀의 정제 방법.
A process for purifying 2,6-dimethylphenol through azeotropic distillation from a mixture of crude 2,6-dimethylphenols containing o-cresol using an azeotropic agent,
A method for purifying 2,6-dimethylphenol using an azeotropic agent of a hydrocarbon mixture having an azeotropic boiling point of 155 to 170 캜.
상기 탄화수소 혼합물의 공비제는 끓는점 150 내지 210℃의 탄화수소 공비제를 분별증류하여 분리된 끓는점 155 내지 170℃의 탄화수소 혼합물인 2,6-디메틸페놀의 정제 방법.
The method according to claim 1,
The azeotropic agent of the hydrocarbon mixture is a hydrocarbon mixture having a boiling point of from 155 to 170 DEG C separated by fractional distillation of a hydrocarbon azeotropic agent having a boiling point of 150 to 210 DEG C, which is a method for purifying 2,6-dimethylphenol.
상기 끓는점 150 내지 210℃의 탄화수소 공비제는 끓는점 155 내지 170℃의 탄화수소 혼합물을 30중량% 이상 포함하는 것인 2,6-디메틸페놀의 정제 방법.
3. The method of claim 2,
Wherein the hydrocarbon azeotropic agent having a boiling point of 150 to 210 占 폚 comprises at least 30% by weight of a hydrocarbon mixture having a boiling point of 155 to 170 占 폚.
상기 탄화수소 혼합물의 공비제는 o-크레졸을 포함하는 조 2,6-디메틸페놀의 혼합물 100 중량부에 대하여 15 내지 50 중량부로 사용되는 2,6-디메틸페놀의 정제 방법.
The method according to claim 1,
The azeotropic agent of the hydrocarbon mixture is used in an amount of 15 to 50 parts by weight based on 100 parts by weight of a mixture of crude 2,6-dimethylphenol containing o-cresol.
상기 공비증류는 상압에서 수행되는 2,6-디메틸페놀의 정제 방법.
The method according to claim 1,
Wherein the azeotropic distillation is carried out at atmospheric pressure.
상기 공비증류된 공비혼합물에서 2,6-디메틸페놀의 함량은 전체 공비증류된 공비혼합물의 2중량% 미만인 2,6-디메틸페놀의 정제 방법.The method according to claim 1,
Wherein the content of 2,6-dimethylphenol in the azeotropically distilled azeotropic mixture is less than 2% by weight of the total azeotropically distilled azeotropic mixture.
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