JP4356339B2 - Method for producing phenol - Google Patents
Method for producing phenol Download PDFInfo
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- JP4356339B2 JP4356339B2 JP2003084814A JP2003084814A JP4356339B2 JP 4356339 B2 JP4356339 B2 JP 4356339B2 JP 2003084814 A JP2003084814 A JP 2003084814A JP 2003084814 A JP2003084814 A JP 2003084814A JP 4356339 B2 JP4356339 B2 JP 4356339B2
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- phenol
- high boiling
- boiling fraction
- distillation
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims description 67
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 238000009835 boiling Methods 0.000 claims description 74
- 238000004821 distillation Methods 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 21
- 238000000354 decomposition reaction Methods 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 238000001816 cooling Methods 0.000 claims description 16
- 239000008346 aqueous phase Substances 0.000 claims description 9
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 5
- 230000003472 neutralizing effect Effects 0.000 claims description 5
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 4
- 239000012295 chemical reaction liquid Substances 0.000 claims description 3
- 239000012071 phase Substances 0.000 claims description 3
- 238000000197 pyrolysis Methods 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 17
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 238000005979 thermal decomposition reaction Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 1
- 238000010543 cumene process Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- -1 that is Chemical compound 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【０００１】
【発明の属する技術分野】
本発明は、キュメン法フェノール製造法の改良に関するものである。詳しくは、キュメン法フェノール製造法において、蒸留塔の塔底から缶出されるフェノールよりも高沸点の成分を主体とする高沸留分を熱分解して有価物を取得する方法の改良に関するものである。
【０００２】
【従来の技術】
フェノールは工業的に極めて重要な化学品であり、今日ではその大部分はキュメン法により、製造されている。この方法では、先ずベンゼンとプロピレンとを反応させてキュメン、すなわちイソプロピルベンゼンとし、次いでこれを酸化してキュメンハイドロパーオキサイドとしたのち、酸で分解してフェノールとアセトンとを生成させる。酸分解により生成したフェノール及びアセトンを含む酸分解反応液は、中和されたのち洗浄されて生成した塩が除去され、次いで蒸留によりフェノール及びアセトンが得られる。このとき、蒸留工程から缶出されたフェノールよりも沸点の高い成分を主体とする高沸留分は熱分解装置に供給して熱分解され、α−メチルスチレン、フェノール及びその他の有価物を生成させ、これらを取得する。
【０００３】
酸分解反応液からのアセトン及びフェノールの取得方法はいくつか提案されているが、通常は先ず酸分解反応液を蒸留して、アセトン及びフェノールよりも低沸点の成分を主体とする粗アセトン留分と、フェノール及びフェノールよりも高沸点の成分を主体とする粗フェノール留分とに分離し、次いでそれぞれの留分を更に蒸留してアセトン及びフェノールを取得する。
【０００４】
粗フェノール留分からフェノールを取得する方法もいくつか提案されている。その代表的なものは、粗フェノール留分をフェノールを主体とする留分とフェノールよりも高沸点の成分を主体とする高沸留分とに蒸留分離し、次いでフェノールを主体とする留分を更に蒸留精製してフェノールを取得する方法；並びに粗フェノール留分を残存しているフェノールよりも低沸点の成分を主体とする軽沸留分と、フェノール及びフェノールよりも高沸点の成分を主体とする高沸留分とに蒸留分離し、後者を更に蒸留してフェノールを主体とする留分と高沸留分とに分離し、ここに得られたフェノールを主体とする留分を更に蒸留精製してフェノールを取得する方法である。また、フェノールを主体とする留分を側流として抜出すことにより、粗フェノール留分を軽沸留分、フェノールを主体とする留分及び高沸留分に分離し、ここに得られたフェノールを主体とする留分を更に蒸留精製してフェノールを取得する方法もある。
【０００５】
いずれの方法においても、蒸留塔の塔底からは、フェノールよりも高沸点の成分を主体とする高温の高沸留分が缶出される。この高沸留分からは熱分解装置で熱分解することにより、α−メチルスチレン、フェノールその他の有価物が取得される。酸分解反応液から高沸留分を分離する蒸留系と高沸留分の熱分解系とは別系統となっており、蒸留塔から高温で缶出された高沸留分は、冷却されたのち貯槽に収容され、次いで貯槽から熱分解系に供給される。高沸留分中には、酸分解反応液を中和した際に生成した塩が微量残存しており、この塩は後続する高沸留分の処理の障害となる。したがって、熱分解系に供給される前に、高沸留分は水などの洗浄液で洗浄されて残存している塩が除去されている。例えば特開平８−３０１８０３号公報には、抽出機において高沸留分を約１０〜９０℃の温度で、高沸留分／水の供給比を少なくとも０．３／１として水と混合して洗浄することが記載されている。
【０００６】
【発明が解決しようとする課題】
蒸留塔の塔底から缶出された高温の高沸留分を、そのまま冷却装置で冷却すると、冷却装置及びこれに続く管路に閉塞が頻発するという問題がある。本発明者らの検討によると、この閉塞は高沸留分中に含まれている塩の析出によるものと考えられる。閉塞が起こると、これを解消させるための臨時作業が必要であり、運転管理上大きな問題となる。したがって、本発明は、高温の高沸留分を冷却するに際し、閉塞を起こさせない方法を提供しようとするものである。
【０００７】
【課題を解決するための手段】
本発明の要旨は、キュメンハイドロパーオキサイドの酸分解反応液を中和したのち、蒸留してフェノールよりも低沸点の成分を留出させ、フェノールよりも高沸点の成分を主体とする高沸留分を蒸留塔の塔底から缶出する蒸留工程、及びこの高沸留分を冷却したのち貯槽に収容し、次いで貯槽から熱分解系に供給し熱分解してα−メチルスチレン及びフェノールを含む有価物を生成させる熱分解工程を有するフェノールの製造方法において、蒸留塔の塔底から缶出された温度１６０〜２２０℃の高沸留分を水と混合したのち冷却装置に導入して冷却し、静置して油相と水相を分離して得られた高沸留分を熱分解することを特徴とする方法、に存する。
【０００８】
【発明の実施の形態】
本発明では、キュメンハイドロパーオキサイドの酸分解反応液を中和したのち、蒸留してアセトン及びフェノール等を取得する蒸留工程における蒸留塔の塔底から缶出される、フェノールよりも高沸点の成分を主体とする任意の高沸留分を対象とすることができる。
【０００９】
キュメンハイドロパーオキサイドの酸分解は、通常はキュメンハイドロパーオキサイドを硫酸と接触させることにより行われ、生成した酸分解反応液は苛性ソーダにより中和される。したがって、通常、中和後の酸分解反応液に含まれている塩は硫酸ナトリウムである。硫酸ナトリウムは後続する酸分解反応液を蒸留してアセトン及びフェノールを取得する蒸留工程の障害となるので、中和後の酸分解反応液を水洗することにより硫酸ナトリウムが除去される。通常、この水洗処理には酸分解反応液中のフェノール及びアセトンが水洗液中に溶解して失われるのを防止するため、硫酸ナトリウム水溶液が用いられている。
【００１０】
硫酸ナトリウムが除去された酸分解反応液からは、一連の蒸留操作によりアセトン及びフェノールが取得されると共に、フェノールよりも高沸点の成分を主体とする高温の高沸留分が蒸留塔の塔底から缶出される。缶出時の高沸留分の温度は、蒸留方法により異なるが、通常１６０℃以上であり、多くの場合には１７０〜２２０℃の範囲である。代表的な方法では、先ず中和後の酸分解反応液をアセトン及びフェノールよりも軽沸点成分を主体とする粗アセトン留分と、フェノール及びこれよりも高沸点の成分を主体とする粗フェノール留分とに分離し、次いで粗フェノール留分を更に蒸留して、フェノールを主体とするフェノール留分と、フェノールよりも高沸点の成分を主体とする高沸留分とに分離する。この蒸留は常圧ないし若干の減圧下に行われることが多いので、塔底から缶出される高沸留分の温度は通常２００℃前後である。この高沸留分には、通常は重量で１〜３０％のフェノールと１０〜５００ｐｐｍの硫酸ナトリウムが含まれている。
【００１１】
本発明に係る製造方法では、この蒸留塔の塔底から缶出された高温の高沸留分と水とを混合して冷却装置に導入する。高沸留分に対する水の混合比率が小さいと閉塞を十分に阻止することができないので、水の混入比率は冷却装置及び後続する管路における閉塞の発生状況に応じて決定される。通常は高沸留分に対して１重量％以上の水を混合に用いる必要がある。閉塞を確実に防止するには２重量％以上、特に３重量％以上の水と混合するのが好ましい。しかし、通常は１０重量％を越える水と混合する必要はない。
【００１２】
高沸留分と水との混合液は、常法に従って冷却すればよい。冷却装置としては多管式熱交換器のような常用の間接冷却装置が挙げられる。冷却温度は任意であるが通常は雰囲気温度ないし６０℃であり、３０〜６０℃が好ましい。冷却後の混合液は所望により更に水と混合したのち静置して油相と水相を分離する。水相中には高沸留分中に含まれていた硫酸ナトリウム及びフェノールが存在するので、水相からフェノールを回収するのが好ましい。水相からフェノールを回収する最も簡単な方法は、水相と中和後の酸分解反応液の洗浄水とを混合して処理する方法である。なお、冷却後の高沸留分から分離回収した水相の一部は、高沸留分と混合する水として循環使用することもできる。
【００１３】
本発明に係る製造方法によれば、高温の高沸留分と水とを混合するので、高沸留分中の硫酸ナトリウムが水相へ効率よく抽出されるという利点がある。これは、水が高温の高沸留分と接触して速やかに水蒸気となって体積が膨張したのち、冷却されて水滴となって体積が収縮することにより、高沸留分と水との接触が極めて良好に行われるためと考えられる。高温の高沸留分と水とを混合する場所は、蒸留塔の塔底から冷却装置までの間であればどこでもよいが、ポンプのキャビテーションを防止する見地からは、蒸留塔の塔底から缶出された高沸留分を冷却装置へ送出する塔底ポンプの後が好ましい。
【００１４】
【実施例】
本発明を実施例により更に具体的に説明するが、本発明は以下の実施例に限定されるものではない。
実施例１
キュメンハイドロパーオキサイドの酸分解反応液を、中和及び洗浄したのち、蒸留塔に供給して蒸留し、塔頂からアセトン及びキュメンなどの軽沸留分を留出させ、塔底からフェノール及び高沸留分を缶出させた。この塔底缶出液を蒸留塔で更に蒸留し、塔頂からフェノールを留出させ、塔底から下記の表１の組成の塔底液（１７６℃）をポンプで抜出した。
【００１５】
【表１】
ポンプ出口で、塔底液と塔底液に対して３重量％の水とを混合し、直列に接続された２基の多管式熱交換器を経て貯槽に流出させた。塔底液の温度は前段熱交換器出口で９０〜１００℃、後段熱交換器出口で５０〜５５℃であった。このようにして３ヶ月間連続運転したところ、熱交換器及び後続する管路に閉塞は生じなかった。一方、塔底液と水とを混合しなかった場合には、閉塞が頻発し、１ヶ月間で６回熱交換器と管路の洗浄を行わなければならなかった。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an improvement in the cumene process phenol production process. More specifically, in the cumene method phenol production method, it relates to an improvement in a method for obtaining a valuable material by pyrolyzing a high boiling fraction mainly composed of components having a higher boiling point than phenol extracted from the bottom of a distillation column. is there.
[0002]
[Prior art]
Phenol is an industrially very important chemical, and today most of it is produced by the cumene method. In this method, benzene and propylene are first reacted to form cumene, that is, isopropylbenzene, and then oxidized to cumene hydroperoxide, which is then decomposed with an acid to produce phenol and acetone. The acid decomposition reaction solution containing phenol and acetone generated by acid decomposition is neutralized and washed to remove the generated salt, and then phenol and acetone are obtained by distillation. At this time, a high boiling fraction mainly composed of components having a boiling point higher than that of phenol extracted from the distillation process is supplied to a thermal decomposition apparatus and thermally decomposed to produce α-methylstyrene, phenol and other valuable materials. Let's get these.
[0003]
Several methods for obtaining acetone and phenol from the acid decomposition reaction solution have been proposed. Usually, the acid decomposition reaction solution is first distilled to obtain a crude acetone fraction mainly composed of components having a boiling point lower than that of acetone and phenol. And a crude phenol fraction mainly composed of phenol and a component having a boiling point higher than that of phenol, and then each fraction is further distilled to obtain acetone and phenol.
[0004]
Several methods for obtaining phenol from the crude phenol fraction have also been proposed. A typical example is that a crude phenol fraction is separated by distillation into a fraction mainly composed of phenol and a high boiling fraction mainly composed of components having a higher boiling point than phenol, and then a fraction mainly composed of phenol is separated. Further, a method of obtaining phenol by distillation purification; and a light boiling fraction mainly composed of components having a lower boiling point than phenol in which the crude phenol fraction remains, and mainly a component having a higher boiling point than phenol and phenol. The high-boiling fraction is distilled and separated, the latter is further distilled to separate the phenol-based fraction and the high-boiling fraction, and the resulting phenol-based fraction is further purified by distillation. It is a method to obtain phenol. In addition, the phenol-based fraction obtained by separating a crude phenol fraction into a light boiling fraction, a phenol-based fraction and a high-boiling fraction by extracting a fraction mainly comprising phenol as a side stream. There is also a method of obtaining phenol by further distilling and purifying a fraction mainly composed of.
[0005]
In either method, a high-temperature high-boiling fraction mainly composed of components having a boiling point higher than that of phenol is taken out from the bottom of the distillation column. From this high boiling fraction, α-methylstyrene, phenol and other valuable materials are obtained by thermal decomposition with a thermal decomposition apparatus. The distillation system that separates the high boiling fraction from the acid decomposition reaction solution and the thermal decomposition system of the high boiling fraction are separate systems, and the high boiling fraction taken out from the distillation tower at a high temperature is cooled. After that, it is accommodated in a storage tank and then supplied from the storage tank to the thermal decomposition system. In the high boiling fraction, a trace amount of salt formed when the acid decomposition reaction solution is neutralized remains, and this salt becomes an obstacle to the treatment of the subsequent high boiling fraction. Therefore, before being supplied to the thermal decomposition system, the high boiling fraction is washed with a washing liquid such as water to remove the remaining salt. For example, JP-A-8-301803 discloses that an extractor is mixed with water at a high boiling fraction at a temperature of about 10 to 90 ° C. and a high boiling fraction / water supply ratio of at least 0.3 / 1. It is described to be washed.
[0006]
[Problems to be solved by the invention]
When the high-temperature high-boiling fraction taken out from the bottom of the distillation column is cooled as it is with a cooling device, there is a problem that blockages frequently occur in the cooling device and the subsequent pipe line. According to the study by the present inventors, this blockage is considered to be due to the precipitation of the salt contained in the high boiling fraction. When the blockage occurs, a temporary work is required to solve this, which becomes a big problem in operation management. Therefore, the present invention seeks to provide a method that does not cause clogging when cooling a high-temperature, high-boiling fraction.
[0007]
[Means for Solving the Problems]
The gist of the present invention is that after neutralizing the acid decomposition reaction liquid of cumene hydroperoxide, distillation is performed to distill components having a lower boiling point than phenol, and high boiling distillation mainly composed of components having a higher boiling point than phenol. A distillation step of removing the fraction from the bottom of the distillation column, and this high boiling fraction is cooled and then stored in a storage tank, and then supplied from the storage tank to a thermal decomposition system and pyrolyzed to contain α-methylstyrene and phenol. in the production method of phenol with pyrolysis step to produce valuable materials, the high-boiling fraction of the can out temperature 160 to 220 ° C. from the bottom of the distillation column was cooled by introducing a cooling device were mixed with water And a method characterized by thermally decomposing a high boiling fraction obtained by separating the oil phase and the aqueous phase by standing .
[0008]
DETAILED DESCRIPTION OF THE INVENTION
In the present invention, after neutralizing the acid decomposition reaction solution of cumene hydroperoxide, a component having a higher boiling point than phenol extracted from the bottom of the distillation column in a distillation step in which acetone and phenol are obtained by distillation. Arbitrary high boiling fractions as the main component can be targeted.
[0009]
The acid decomposition of cumene hydroperoxide is usually carried out by bringing cumene hydroperoxide into contact with sulfuric acid, and the resulting acid decomposition reaction solution is neutralized with caustic soda. Therefore, normally, the salt contained in the acid decomposition reaction solution after neutralization is sodium sulfate. Sodium sulfate is an obstacle to the distillation step in which the subsequent acid decomposition reaction solution is distilled to obtain acetone and phenol, so that the sodium sulfate is removed by washing the neutralized acid decomposition reaction solution with water. Usually, in this washing treatment, an aqueous sodium sulfate solution is used to prevent the phenol and acetone in the acid decomposition reaction solution from being dissolved and lost in the washing solution.
[0010]
Acetone and phenol are obtained from the acid decomposition reaction solution from which sodium sulfate has been removed by a series of distillation operations, and a high-temperature high-boiling fraction mainly composed of components having a boiling point higher than that of phenol is obtained at the bottom of the distillation column. Is taken out from. Although the temperature of the high boiling fraction at the time of taking out changes with distillation methods, it is normally 160 degreeC or more, and is the range of 170-220 degreeC in many cases. In a typical method, first, the neutralized acid decomposition reaction solution is divided into a crude acetone fraction mainly composed of light-boiling components than acetone and phenol, and a crude phenol fraction composed mainly of phenol and components having a higher boiling point than this. Then, the crude phenol fraction is further distilled to separate into a phenol fraction mainly composed of phenol and a high boiling fraction mainly composed of components having a boiling point higher than that of phenol. Since this distillation is often performed under normal pressure or slightly reduced pressure, the temperature of the high-boiling fraction discharged from the bottom of the column is usually around 200 ° C. This high boiling fraction usually contains 1-30% phenol and 10-500 ppm sodium sulfate by weight.
[0011]
In the production method according to the present invention, the high-temperature high-boiling fraction extracted from the bottom of the distillation column and water are mixed and introduced into the cooling device. Since the clogging cannot be sufficiently prevented when the mixing ratio of water to the high boiling fraction is small, the mixing ratio of water is determined according to the occurrence of clogging in the cooling device and the subsequent pipe. Usually, it is necessary to use 1% by weight or more of water for mixing with respect to the high boiling fraction. In order to reliably prevent clogging, it is preferable to mix with 2% by weight or more, particularly 3% by weight or more of water. However, it is usually not necessary to mix with more than 10% by weight of water.
[0012]
What is necessary is just to cool the liquid mixture of a high boiling fraction and water in accordance with a conventional method. As the cooling device, a common indirect cooling device such as a multi-tube heat exchanger may be mentioned. Although the cooling temperature is arbitrary, it is usually from ambient temperature to 60 ° C., preferably from 30 to 60 ° C. The mixed solution after cooling is further mixed with water if desired, and then allowed to stand to separate the oil phase and the aqueous phase. Since sodium sulfate and phenol contained in the high boiling fraction are present in the aqueous phase, it is preferable to recover phenol from the aqueous phase. The simplest method for recovering phenol from the aqueous phase is a method in which the aqueous phase is mixed with the washing water of the acid decomposition reaction solution after neutralization. A part of the aqueous phase separated and recovered from the high boiling fraction after cooling can be circulated as water mixed with the high boiling fraction.
[0013]
According to the production method of the present invention, since a high-temperature high-boiling fraction and water are mixed, there is an advantage that sodium sulfate in the high-boiling fraction is efficiently extracted into the aqueous phase. This is because when water comes into contact with a high-temperature, high-boiling fraction and quickly becomes water vapor, the volume expands and then cools to form water droplets that shrink the volume. Is considered to be performed very well. The place where the high-temperature high-boiling fraction and water are mixed may be anywhere from the bottom of the distillation column to the cooling device, but from the standpoint of preventing pump cavitation, the can can be added from the bottom of the distillation column. It is preferable after the bottom pump that delivers the high-boiling fraction discharged to a cooling device.
[0014]
【Example】
Examples The present invention will be described more specifically with reference to examples. However, the present invention is not limited to the following examples.
Example 1
After neutralizing and washing the cumene hydroperoxide acid decomposition reaction solution, it is fed to the distillation column to distill, distilling light boiling fractions such as acetone and cumene from the top of the column, and phenol and high water from the bottom of the column. The boiling fraction was removed. This bottoms bottom effluent was further distilled in a distillation tower, phenol was distilled from the top of the tower, and a bottom liquid (176 ° C.) having the composition shown in Table 1 below was extracted from the bottom of the tower with a pump.
[0015]
[Table 1]
At the pump outlet, the bottom liquid and 3% by weight of water were mixed with respect to the bottom liquid, and were discharged to the storage tank through two multi-tube heat exchangers connected in series. The temperature of the column bottom liquid was 90 to 100 ° C. at the outlet of the front heat exchanger and 50 to 55 ° C. at the outlet of the rear heat exchanger. In this way, when operated continuously for 3 months, the heat exchanger and the subsequent pipe line were not blocked. On the other hand, when the tower bottom liquid and water were not mixed, clogging occurred frequently, and the heat exchanger and the pipe line had to be washed six times in one month.
Claims (5)
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| US11993564B2 (en) | 2020-07-17 | 2024-05-28 | Lg Chem, Ltd. | Method of decomposing phenolic by-products |
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