KR0140052B1 - An antifoulant for petrochemical processes - Google Patents
An antifoulant for petrochemical processesInfo
- Publication number
- KR0140052B1 KR0140052B1 KR1019940015379A KR19940015379A KR0140052B1 KR 0140052 B1 KR0140052 B1 KR 0140052B1 KR 1019940015379 A KR1019940015379 A KR 1019940015379A KR 19940015379 A KR19940015379 A KR 19940015379A KR 0140052 B1 KR0140052 B1 KR 0140052B1
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- KR
- South Korea
- Prior art keywords
- ethylene
- tower
- manufacturing plant
- depropane
- plant
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G9/00—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
- C10G9/14—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils in pipes or coils with or without auxiliary means, e.g. digesters, soaking drums, expansion means
- C10G9/16—Preventing or removing incrustation
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G7/00—Distillation of hydrocarbon oils
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G75/00—Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general
- C10G75/04—Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general by addition of antifouling agents
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
수소공여성 히드로방향족화합물로 이루어진 에틸렌제조플랜트의 탈프로판탑용 오염방지제로서, 취급이 용이하고, 저렴하며, 프로세스에 악영향을 주지 않는 한편, 오염방지효과가 우수하여, 장기간 안정하게 플랜트를 연속작동시킬 수 있다.Anti-propane tower decontamination agent of ethylene plant made of hydrogen donating hydroaromatic compound, easy to handle, inexpensive, does not adversely affect the process, and has excellent anti-pollution effect. Can be.
Description
본 발명은 신규의 석유화학프로세스용 오염방지제에 관한 것으로, 보다 상세하게는, 에틸렌제조플랜트의 탈프로판탑(depropanizer)에서의 정류프로세스에서 오염형성을 효율적으로 방지할 수 있는 에틸렌제조플랜트의 탈프로판탑용 오염방지제에 관한 것이다.The present invention relates to a novel anti-pollution agent for petrochemical processes, and more particularly, to a depropan of an ethylene manufacturing plant which can effectively prevent contamination formation in the rectification process in a depropanizer of an ethylene manufacturing plant. The present invention relates to a tower antifouling agent.
에틸렌제조플랜트에 있어서는, 에틸렌 및 프로필렌 등의 올레핀, 부타디엔 등의 디올레핀을 함유하는 유체를 증류시키고 있으며, 이런 유체의 증류프로세스에 있어서는, 해당 유체는 예열열교환기 혹은 리보일러에서 가열에 의해 열변성됨으로써 슬러지를 형성하게 되고, 이런 슬러지는 예열열교환기 혹은 리보일러의 열전달면 또는 배관면에 부착되어 불가피하게 오염을 형성하게 된다.In ethylene production plants, fluids containing olefins such as ethylene and propylene and diolefins such as butadiene are distilled. In the distillation process of such fluids, the fluid is heat-modified by heating in a preheater or reboiler. As a result, sludge is formed, and the sludge is attached to a heat transfer surface or a pipe surface of a preheat exchanger or a reboiler, which inevitably forms contamination.
오염형성기구로서 다음과 같은 현상이 공지되어 있다. 즉, 에틸렌제조플랜트의 탈프로판탑에 있어서, 프로세스유체중의 올레핀 혹은 디올레핀 같은 불포화탄화수소 등의 쉽게 산화되는 유기화합물이 용존산소에 의해 히드로퍼옥시드로 되고, 이 히드로퍼옥시드는 열에 의해, 특히 금속 등의 촉매활성을 지닌 물질의 존재하에 분해하여 케톤, 알데히드, 카르복실산 등을 형성하고, 이들 화합물의 중합하여 올리고머나 폴리머로 되어 슬러지를 형성한다.The following phenomenon is known as a pollution formation mechanism. That is, in the depropane tower of an ethylene manufacturing plant, organic compounds which are easily oxidized such as unsaturated hydrocarbons such as olefins or diolefins in the process fluid become hydroperoxides by dissolved oxygen, and the hydroperoxides are heated by heat, in particular. It decomposes in the presence of a substance having catalytic activity such as a metal to form ketones, aldehydes, carboxylic acids and the like, and polymerize these compounds to form oligomers or polymers to form sludge.
그러므로, 상술한 오염을 방지할 목적으로, 종래 석유화학프로세스에 있어서는 오염방지제로서 페놀게나 아민계의 산화방지제, 옥심계나 니트로소계의 중합방지제, 슬러지의 형성과 침적물이 부착을 방지하기 위한 분산제, 및 이들을 조합한 것을 사용하고 있으며, 예를들어, (1)아닐린과 t-부틸카테콜로의 조합으로 이루어진 오염방지제(일본국 특공소 59-24138), (2)니트로소페놀로 이루어진 오염방지제(일본국 특개평3-350147), (3) 니트로소화합물로 이루어진 오염방지제(일본국 특공평 4-26639), (4) 아민화합물로 이루어진 오염방지제(일본국 특개소 64-13041) 등이 개시되어 있다.Therefore, in order to prevent the above-mentioned contamination, in the conventional petrochemical process, as a pollution inhibitor, a phenol- or amine-based antioxidant, an oxime-based or nitroso-based polymerization inhibitor, a dispersant for preventing the formation of sludge and deposition, and Combinations of these are used, and include, for example, (1) antifouling agents consisting of a combination of aniline and t-butyl catechol (JP-A 59-24138), (2) antifouling agents consisting of nitrosophenols (Japan Japanese Patent Application Laid-Open No. 3-350147), (3) an antifouling agent consisting of a nitroso compound (Japanese Patent Application Laid-open No. Hei 4-26639), (4) an antifouling agent consisting of an amine compound (Japanese Patent Publication No. 64-13041), and the like are disclosed. have.
그러나, 이들 오염방지제는 프로세스에 직접 첨가되기 때문에, 제품을 착색시키고, 바람직하지 않는 부산물이 생성되며, 더욱이, 취급이 어렵고 고가일 뿐아니라, 2년이상의 장기간동안 연속작동시킬 때에는 오염방지효과가 불충분하여 문제점을 야기한다고 하는 결점을 지니고 있었다.However, since these antifouling agents are added directly to the process, they color products, produce undesirable by-products, and are not only difficult to handle and expensive, but also have insufficient antifouling effects when operated continuously for longer than two years. Had the drawback of causing problems.
상술한 바와 같이, 종래의 오염방지제는 항상 만족스러운 것이 아니므로, 다루기 쉽고, 저렴하며, 프로세스에 악영향을 미치지 않고, 오염형성을 효율적으로 방지하여 우수한 안정성으로 장기연속작동시킬 수 있는 에틸렌제조프랜트의 탈프로 판탑용 오염방지제의 개발을 강하게 열망하였다.As described above, the conventional antifouling agent is not always satisfactory, so it is easy to handle, inexpensive, and does not adversely affect the process. There was a strong desire for the development of anti-pollution agents for talpro towers.
따라서, 본 발명의 목적은 종래의 에틸렌제조플랜트의 탈프로판탑용 오염방지제에서의 결점을 제거하여, 취급이 쉽고, 저렴하며, 프로세스에 악영향을 미치지 않고, 오염형성을 효율적으로 방지하여, 우수한 안정성으로 플랜트를 장시간 연속 작동시킬 수 있는 에틸렌제조플랜트의 탈프로판탑용 오염방지제를 제공하는 것이다.Accordingly, an object of the present invention is to eliminate the drawbacks of the conventional anti-propane tower antifouling agent of the ethylene manufacturing plant, easy to handle, inexpensive, without adversely affecting the process, and effectively prevent contamination formation, with excellent stability It is to provide an antifouling agent for depropane tower of an ethylene manufacturing plant that can operate the plant continuously for a long time.
본 발명자는 상술한 유익한 특성의 에틸렌제조플랜트의 탈프로판탑용 오염방지제를 개발하기 위해 예의 연구한 결과, 상기 목적은, 수소공여성 히드로방향족 화합물을 함유하는 오염방지제에 의해 달성될 수 있음을 발견하여 본 발명을 완성하였다.The present inventors earnestly researched to develop an anti-propane tower antifouling agent of the ethylene manufacturing plant of the above-described beneficial properties, the above object can be achieved by an antifouling agent containing a hydrogen donating hydroaromatic compound The present invention has been completed.
즉, 본 발명은 수소공여성 히드로방향족화합물로 이루어진 에틸렌제조플랜트의 탈프로판탑용 오염방지제를 제공하는 것이다.That is, the present invention is to provide an anti-propane tower antifouling agent of the ethylene manufacturing plant consisting of a hydrogen donating hydroaromatic compound.
또한, 본 발명은 오염이 형성되어 있는 에틸렌제조플랜트의 탈프로판탑에 공급된 프로세스유체에 상술한 에틸렌제조플랜트의 탈프로판탑용 오염방지제를 첨가하는 것으로 이루어진 에틸렌제조플랜트에서의 오염형성을 방지하는 방법을 제공하는 것이다.In addition, the present invention is a method for preventing the formation of contamination in the ethylene production plant consisting of adding the above-mentioned anti-propane for the depropane tower of the ethylene manufacturing plant to the process fluid supplied to the depropane tower of the ethylene manufacturing plant is contaminated. To provide.
본 발명의 상기 및 기타목적, 특징 및 이점은 다음 설명으로부터 더욱 명확해질 것이다.These and other objects, features and advantages of the present invention will become more apparent from the following description.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
상술한 바와 같이, 오염형성은 프로세스유체중의 올레핀 및 디올레핀등의 불포화탄화수소가 라디칼연쇄반응에 의해 산화되어 야기된 것이다. 본 발명의 오염방지제에 사용된 수소공여성 히드로방향족화합물은 산화시 발생하는 라디칼에 프로톤을 공여함으로써 연쇄반응을 정지시켜 오염을 효과적으로 방지하는 작용을 지닌다. 수소공여성히드로 방향족화합물의 예로는, 테트라린, 9, 10-디히드로페난트렌, 1, 2, 3, 4, 5, 6, 7, 8-옥타히드로페난트렌 및 수소화터페닐 등을 들 수 있다. 이들은 단독으로 사용되거나 2종이상의 화합물을 조합하여 사용할 수도 있다.As described above, contamination is caused by the oxidation of unsaturated hydrocarbons such as olefins and diolefins in the process fluid by radical chain reaction. The hydrogen donating hydroaromatic compound used in the antifouling agent of the present invention has an action of effectively preventing contamination by stopping a chain reaction by donating protons to radicals generated during oxidation. Examples of hydrogen donating hydroaromatic compounds include tetralin, 9, 10-dihydrophenanthrene, 1, 2, 3, 4, 5, 6, 7, 8-octahydrophenanthrene, hydrogenated terphenyl, and the like. have. These may be used alone or in combination of two or more compounds.
본 발명의 오염방지제에는, 히드로방향족탄화수소이외에도 소망에 따라 종래 공지의 오염방지제, 예를 들면, 아민계 및 페놀계의 산화방지제, 옥심계 및 니트로 소계의 중합방지제, 금속불활성제, 각종 분산제 등을 첨가할 수 있다. 분산제는 유기슬러지 및 무기슬러지를 프로세스유체중에 분산시켜 열전달면 또는 배관면으로의 침적물의 부착을 방지하는 것으로, 이와같은 분산제로서는,In addition to hydroaromatic hydrocarbons, the antifouling agent of the present invention may be a conventionally known antifouling agent, for example, an amine-based and phenol-based antioxidant, an oxime-based and nitro-based polymerization inhibitor, a metal inert, and various dispersants. Can be added. The dispersant disperses organic sludge and inorganic sludge in the process fluid to prevent deposition of deposits on the heat transfer surface or the pipe surface.
(1) 분자량이 1,000∼10,000정도인 폴리알킬(메타)아크릴레이트와 하기일반식(1) Polyalkyl (meth) acrylate having a molecular weight of about 1,000 to 10,000 and the following general formula
(식중, R1은 탄소수10∼15의 탄화수소기, n은 1∼5, 바람직하게 1∼3의 정수, m은 1∼10, 바람직하게 1∼3의 정수)로 표현되는 폴리에틸렌 폴리아민 나프텐산아미드와의 중량비 90 : 10∼10 : 90의 혼합물 ;Polyethylene polyamine naphthenic amide represented by (wherein, R 1 is a hydrocarbon group having 10 to 15 carbon atoms, n is an integer of 1 to 5, preferably 1 to 3, m is an integer of 1 to 10, preferably 1 to 3). A weight ratio of 90: 10 to 10: 90;
(2) 하기 일반식(2) the following general formula
및And
(식중, R2는 분자량 400∼3,000인 폴리부텐기, R3은 탄소수1∼5, 바람직하게는 1∼3의 알킬렌기, R4및 R5는 각각 수소원자 또는 탄소수1∼5, 바람직하게는 1∼3의 알킬기, p는 1∼10의 정수)중의 하나로 표현되는 숙신이미드유도체 ;Wherein R 2 is a polybutene group having a molecular weight of 400 to 3,000, R 3 is an alkylene group of 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms, R 4 and R 5 are each a hydrogen atom or 1 to 5 carbon atoms, preferably Is a succinimide derivative represented by one of 1 to 3 alkyl groups, p is an integer of 1 to 10;
(3) 하기일반식(3) the following general formula
(식중, R6은 분자량500∼2,000인 폴리부텐기)로 표현되는 티오인산에스테르 유도체, 또는 그 에틸렌옥시드부가물 ; 및Thiophosphate ester derivatives represented by (wherein R 6 is a polybutene group having a molecular weight of 500 to 2,000) or an ethylene oxide adduct thereof; And
(4) 하기일반식(4) the following general formula
(식중, R7, R8은 각각 탄소수12∼18의 직쇄 혹은 분지알킬기 또는 알켄일기, q : r(몰비)=1 : 9∼9 : 1)(Wherein R 7 and R 8 each represent a straight-chain or branched alkyl group having 12 to 18 carbon atoms or an alkenyl group, q: r (molar ratio) = 1: 9-9: 1)
로 표현되는 분자량 10,000∼1,000,000인 스티렌과 말레인산에스테르의 공중합체등을 들 수 있다. 이들 분산제는 소망에 따라 2종이상으로 조합하여 사용할 수 있다.And copolymers of styrene and maleic acid ester having a molecular weight of 10,000 to 1,000,000. These dispersants can be used in combination of 2 or more types as desired.
상기 분사제(1)에 사용된 폴리알킬(메타)아크릴레이트의 예로는, 알킬기의 탄소수가 5∼18인 알킬(메타)아크릴레이트의 단독중합체, 상기 알킬(메타)아크릴레이트 2종이상을 공중합하여 얻은 공중합체 및 상기 알킬(메타)아크릴레이트 1종이상과 N-비닐-2-피롤리돈, 디에틸아미노에틸(메타)아크릴레이트 등의 에틸렌성 불포화결합을 지니는 불포화단량체 1종이상을 공중합시켜 얻은 공중합체 등을 들 수 있다.As an example of the polyalkyl (meth) acrylate used for the said propellant (1), the homopolymer of the alkyl (meth) acrylate of 5-18 carbon atoms of an alkyl group is copolymerized, and 2 or more types of said alkyl (meth) acrylates are copolymerized. A copolymer obtained by copolymerization with at least one alkyl (meth) acrylate and at least one unsaturated monomer having an ethylenically unsaturated bond such as N-vinyl-2-pyrrolidone and diethylaminoethyl (meth) acrylate. The copolymer obtained, etc. are mentioned.
산화방지제, 중합방지제, 금속불활성화제 및 분산제 등의 오염방지제에 있어서 소망에 따라 사용되는 성분의 양에 대해선 특히 제한은 없으나, 적절하게 선택하면 된다.Although there is no restriction | limiting in particular about the quantity of the component used for antifouling agents, such as antioxidant, a polymerization inhibitor, a metal deactivator, and a dispersing agent, if desired, What is necessary is just to select suitably.
본 발명의 오염방지제가 적용되는 프로세스유체에 대해서는 특히 제한은 없고, 에틸렌제조플랜트의 탈프로판탑에 있어서 처리될 때 오염이 형성되는 어떤 종류의 피처오일에도 본 발명의 오염방지제를 적용할 수 있으나, 특히, 에틸렌제조플랜트에 있어서 탈프로판탑, 탈에탄탑, 탈부탄탑 또는 응축물 스트립퍼 등의 증류탑에 있어서의 예열열교환기 혹은 리보일러에서 처리되는 프로세스오일에 적용하는 것이 바람직하다.There is no particular limitation on the process fluid to which the antifouling agent of the present invention is applied, and the antifouling agent of the present invention may be applied to any kind of feature oil in which contamination is formed when treated in a depropane tower of an ethylene manufacturing plant. In particular, it is preferable to apply to the process oil processed by the preheat heat exchanger or the reboiler in a distillation column, such as a depropane tower, a deethan tower, a debutane tower, or a condensate stripper, in an ethylene manufacturing plant.
다음, 본 발명의 오염방지제의 바람직한 사용방법의 일례에 대해서 설명한다. 먼저, 수소공여성 히드로방향족화합물 및 필요에 따라 부가적으로 사용되는 다른 오염방지제 및 보조제 등의 기타 성분을 적당한 용매에 용해하여 0.5∼60중량%의 농도에 용액을 제조하고, 이 용액을 에틸렌제조플랜트의 탈프로판탑에 있어서 오염이 형성되는 설비, 예를들면, 열교환기, 리보일러, 배관 등에 연속첨가하거나 또는 원료오일탱크에 일괄적으로 첨가한다. 이때, 프로세스유체에 대한 본 발명의 오염방지제의 첨가량은 프로세스유체에 대해 통상 0.5∼50,000㎎/ℓ, 바람직하게는 30∼200㎎/ℓ 범위로 선택한다.Next, an example of a preferable method of using the antifouling agent of the present invention will be described. First, a solution is prepared at a concentration of 0.5 to 60 wt% by dissolving other components such as a hydrogen donating hydroaromatic compound and other antifouling agents and auxiliaries additionally used as necessary, in a concentration of 0.5 to 60% by weight. In a depropane tower of a plant, it is added continuously to the installation in which the contamination is formed, for example, a heat exchanger, a reboiler, piping, etc., or it adds it to a raw material oil tank collectively. At this time, the addition amount of the antifouling agent of the present invention to the process fluid is generally selected in the range of 0.5 to 50,000 mg / L, preferably 30 to 200 mg / L, relative to the process fluid.
본 발명의 오염방지제는 오염방지효과가 우수하기 때문에, 종래의 오염방지제를 사용한 경우 단지 3개월간 연속작동시킬 수 있음에 비해, 2년 내지 3년이라고 하는 장기간 동안 안정하게 연속작동시킬 수 있어, 에너지가 절약되며 보수비용도 절약할 수 있고 또한, 플랜트의 긴급정지에 수반한 위험을 회피할 수 있다. 즉, 본 발명으로 얻은 이점을 요약하자면, 본 발명의 에틸렌제조플랜트의 탈프로판탑용 오염방지제는 다루기 쉽고, 저렴하며, 프로세스에 악영향을 주지 않고, 오염방지효과가 뛰어나며, 장기간 플랜트를 안정하게 연속작동시킬 수 있는 한편 에너지절약 및 보수비용의 절감을 도모할 수 있다.Since the antifouling agent of the present invention has excellent antifouling effect, it can be operated continuously stably for a long period of 2 to 3 years, compared to being able to operate continuously for only 3 months when using a conventional antifouling agent, Savings and maintenance costs can be saved and the risks associated with plant emergency shutdowns can be avoided. That is, to summarize the advantages obtained by the present invention, the anti-propane tower decontamination agent of the ethylene manufacturing plant of the present invention is easy to handle, inexpensive, does not adversely affect the process, excellent anti-pollution effect, stable operation for a long time plant In addition, energy saving and maintenance costs can be reduced.
이하, 본 발명을 실시예를 통해 상세히 설명하나, 본 발명은 이들 실시예에 한정된 것은 아니다.Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited to these Examples.
실시예1∼6, 비교예1∼4Examples 1-6, Comparative Examples 1-4
작동중인 플랜트로부터 꺼낸 탈프로판탑바닥부분의 유체에 표1에 나타낸 종류와 양의 약제를 첨가하고, 이것을 SUS 304제의 200밀리리터의 오토클레이브에 장입하여 100℃에서 20시간 가열처리한다. 다음, 처리된 유체를 60℃에서 24시간 진공건조를 행하여 압력을 1mmHg이하로 하여 증발잔류량(폴리머의 형성량)을 구하고, 상기 값과 약제를 첨가하지 않을 때 구한 값과의 비율을 오염형성억제율로 구하여 오염방지특성을 평가한다. 결과를 표1에 나타내었다.The chemicals of the kind and amount shown in Table 1 are added to the fluid of the bottom portion of the depropane tower taken out from the plant in operation, and this is charged into a 200 milliliter autoclave made of SUS 304 and heated at 100 ° C. for 20 hours. Next, the treated fluid was vacuum dried at 60 ° C. for 24 hours to obtain evaporation residual amount (polymer formation amount) with a pressure of 1 mmHg or less, and the ratio between the above value and the value obtained when no drug was added was determined. Evaluate the pollution prevention characteristics. The results are shown in Table 1.
표1에서 분산제는 분자량이 15,000인, 스티렌과 말레인산에스테르와의 공중합체이며, TBC는 t-부틸카테콜을 나타낸다.In Table 1, the dispersant is a copolymer of styrene and maleic acid ester having a molecular weight of 15,000, and TBC represents t-butylcatechol.
(주)약제를 첨가하지 않은 경우의 오염형성량은 전체유체량을 기준으로 할때 0.320wt%이다.Note: The amount of pollution formed when no chemical is added is 0.320wt% based on the total fluid.
비교예 1, 2는 오염형성억제효과에 대해서는 우수하나, p-니트로-o-크레졸은 취급상 문제가 있기 때문에 사용할 수 없다.Comparative Examples 1 and 2 are excellent in the pollution formation inhibitory effect, but p-nitro-o-cresol cannot be used because of handling problems.
Claims (6)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP93-189249 | 1993-07-01 | ||
| JP5189249A JPH0718265A (en) | 1993-07-01 | 1993-07-01 | Antifouling agent for petrochemical process |
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| KR950003422A KR950003422A (en) | 1995-02-16 |
| KR0140052B1 true KR0140052B1 (en) | 1998-06-15 |
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| EP (1) | EP0632121B1 (en) |
| JP (1) | JPH0718265A (en) |
| KR (1) | KR0140052B1 (en) |
| CN (1) | CN1110534C (en) |
| BR (1) | BR9402609A (en) |
| DE (1) | DE69423140T2 (en) |
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| JP2007106926A (en) * | 2005-10-14 | 2007-04-26 | Hakuto Co Ltd | Stain adhesion-preventing agent for petroleum refining and method of preventing stain of petroleum-refining plant |
| US9200213B2 (en) * | 2008-03-24 | 2015-12-01 | Baker Hughes Incorporated | Method for reducing acids in crude or refined hydrocarbons |
| JP5562348B2 (en) | 2009-11-04 | 2014-07-30 | 株式会社日立ハイテクノロジーズ | Opening device and automatic analyzer using the same |
| EP2581421A1 (en) | 2011-10-12 | 2013-04-17 | Ineos Europe AG | Additive |
| EP3504300A1 (en) | 2016-08-25 | 2019-07-03 | General Electric Company | Reduced fouling of hydrocarbon oil |
| CN110337488B (en) * | 2017-02-27 | 2021-11-16 | 埃科莱布美国股份有限公司 | Antifouling agent formulation for compressor |
| JP6485598B1 (en) * | 2017-05-09 | 2019-03-20 | 株式会社片山化学工業研究所 | Methods for preventing contamination of heat exchangers in petroleum processes. |
| CN110452786A (en) * | 2019-08-07 | 2019-11-15 | 南京汇达化工有限公司 | Add hydrogen antiscale agent prescription and its production method |
| US20210155843A1 (en) * | 2019-11-27 | 2021-05-27 | Ecolab Usa Inc. | Anti-fouling compositions for use in crude oil production and processing |
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| CA1291057C (en) * | 1986-12-19 | 1991-10-22 | Junichi Kubo | Method for hydrocracking heavy fraction oils |
| US5215649A (en) * | 1990-05-02 | 1993-06-01 | Exxon Chemical Patents Inc. | Method for upgrading steam cracker tars |
| US5139643A (en) * | 1991-03-13 | 1992-08-18 | Betz Laboratories, Inc. | Phosphorus derivatives of polyalkenylsuccinimides and methods of use thereof |
| EP0576982A1 (en) * | 1992-06-30 | 1994-01-05 | Nippon Oil Co. Ltd. | Process for converting heavy hydrocarbon oil into light hydrocarbon fuel |
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| CN1102848A (en) | 1995-05-24 |
| EP0632121B1 (en) | 2000-03-01 |
| JPH0718265A (en) | 1995-01-20 |
| CN1110534C (en) | 2003-06-04 |
| DE69423140D1 (en) | 2000-04-06 |
| BR9402609A (en) | 1995-04-04 |
| KR950003422A (en) | 1995-02-16 |
| DE69423140T2 (en) | 2000-08-24 |
| EP0632121A3 (en) | 1995-05-17 |
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