EP0632121A2 - An antifoulant for petrochemical processes - Google Patents
An antifoulant for petrochemical processes Download PDFInfo
- Publication number
- EP0632121A2 EP0632121A2 EP94109954A EP94109954A EP0632121A2 EP 0632121 A2 EP0632121 A2 EP 0632121A2 EP 94109954 A EP94109954 A EP 94109954A EP 94109954 A EP94109954 A EP 94109954A EP 0632121 A2 EP0632121 A2 EP 0632121A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- antifoulant
- petrochemical
- fouling
- plant
- petrochemical processes
- 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
Classifications
-
- 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
-
- 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
-
- 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
Definitions
- the present invention relates to a novel antifoulant for petrochemical processes. More particularly, it relates to an antifoulant for petrochemical processes which can effectively prevent formation of fouling in processes in a petrochemical plant, such as the rectification process in an ethylene plant.
- distillation of a fluid containing olefins, such as ethylene and propylene, and diolefins, such as butadiene has been conducted.
- olefins such as ethylene and propylene
- diolefins such as butadiene
- the fluid is modified with heat to form sludge by heating, for example, in a preliminary heat exchanger or a reboiler and the sludge thus formed is adhered to the surface of heat transfer in the preliminary heat exchanger or the reboiler or to the surface of pipings to form fouling.
- antioxidants such as phenolic antioxidants and amine antioxidants
- polymerization inhibitors such as oxime inhibitors and nitroso inhibitors
- dispersants to prevent formation of sludge and adherence of deposit and agents in combinations of these agents
- antifoulants for the purpose of preventing fouling described above.
- an antifoulant comprising a combination of aniline and t-butylcatechol
- an antifoulant comprising nitrosophenol
- the present invention accordingly has an object to provide an antifoulant for petrochemical processes which can eliminate the drawbacks of the conventional antifoulants for petrochemical processes, can be handled easily, is inexpensive, has no adverse effect on the process, shows excellent effect to prevent the formation of fouling, and enables continuous operation of a plant for a long time with good stability.
- the present inventors conducted extensive studies to develop an antifoulant for petrochemical processes having the advantageous properties described above. As the result of the studies, it was discovered that the object can be achieved by an antifoulant comprising a hydrogen-donating hydroaromatic compound.
- the present invention is completed on the basis of the discovery.
- the present invention provides an antifoulant for petrochemical processes comprising a hydrogen-donating hydroaromatic compound.
- the present invention also provides a process for preventing formation of fouling in a petrochemical plant comprising adding the antifoulant for petrochemical processes described above to a process fluid supplied to petrochemical processes in which fouling is formed.
- the hydrogen-donating hydroaromatic compound used as the antifoulant of the present invention has the function of stopping the chain reactions by donating proton to the radical generated in the oxidation and effectively preventing the formation of fouling.
- the hydrogen-donating hydroaromatic compound include tetralin, 9,10-dihydrophenanthrene, 1,2,3,4,5,6,7,8-octahydro-phenanthrene, and hydrogenated terphenyl.
- the compound may be used singly or as a combination of two or more compounds.
- conventional antifoulants such as antioxidants like amine antioxidants and phenol antioxidants, polymerization inhibitors like oxime inhibitors and nitroso inhibitors, metal deactivating agents, and various kinds of dispersant, may be used in addition to the hydroaromatic hydrocarbon according to desire.
- the dispersant disperses organic sludge and inorganic sludge into the process fluid and prevents adherence of deposit to the surface of heat transfer or the surface of pipings. Examples of the dispersant include:
- Examples of the polyalkyl (meth)acrylate used in the dispersant (1) described above include homopolymer of an alkyl (meth)acrylate in which the alkyl group has 5 to 18 carbon atoms, copolymers obtained by copolymerization of two or more kinds of said alkyl (meth)acrylate, and copolymers obtained by copolymerization of one or more kinds of said alkyl (meth)acrylate with one or more kinds of unsaturated monomer having an ethylenically unsaturated bond, such as N-vinyl-2-pyrrolidone and diethylaminoethyl (meth)acrylate.
- Amounts of the components used according to desire in the antifoulant, such as the antioxidant, the polymerization inhibitor, the metal deactivating agent, and the dispersant, are not particularly limited but suitably selected.
- the process fluid to which the antifoulant of the present invention is applied is not particularly limited.
- the antifoulant of the present invention can be applied to any kind of oil for treatment in which fouling is formed in treatments in petrochemical processes. It is preferably applied to process oils treated in a preliminary heat exchanger or a reboiler in a distillation tower, such as a depropanizer, a de-ethanizer, a debutanizer, or a condensate stripper, in an ethylene plant.
- the hydrogen-donating hydroaromatic compound and other components, such as other antifoulants and additional components, which are used additionally according to necessity are dissolved in a suitable solvent to prepare a solution having a concentration of about 0.5 to 60 % by weight.
- the solution thus prepared is added continuously to an apparatus in which fouling is formed in the petrochemical process, such as a heat exchanger, a reboiler or pipings or added to the tank of a material oil in all the amount at one time.
- the amount of the antifoulant of the present invention added to the process fluid is selected generally in the range of 0.5 to 50000 mg/liter, preferably 30 to 200 mg/liter, based on the amount of the process fluid.
- the antifoulant of the present invention has the excellent property to prevent the formation of fouling, continuous operation for a long time, such as for two to three years, is made possible with good stability, in contrast to continuous operation generally practiced for only 3 months when a conventional antifoulant is used. As the result, energy saving and reduction of maintenance cost can be expected and, furthermore, risk accompanied with emergency stopping of the plant can be avoided.
- the antifoulant for petrochemical processes can be handled easily, is inexpensive, has no adverse effect on the process, shows excellent effect to prevent formation of fouling, enables continuous operation of a plant for a long time with good stability and brings energy saving and reduction of maintenance cost.
- Agents of the kinds and the amounts shown in Table 1 were added to a depropanizer bottom fluid taken from a plant in operation.
- the mixture was charged to a 200 milliliter autoclave made of SUS 304 and treated with heat at 100°C for 20 hours. Then, the treated fluid is distilled under a reduced pressure and dried to obtain amount of the residue of evaporation (amount of formed polymer). Rate of suppression of the formation of fouling was calculated for evaluation of the anti-fouling property as the ratio of the value obtained above to the corresponding value obtained in the absence of the agent. Results are shown in Table 1.
- the dispersant is a copolymer of styrene and a maleic acid ester having a molecular weight of 15000 and TBC indicates t-butylcatechol.
- Table 1 agent amount of formed polymer (% by wt.
- Comparative Example 4 aniline 10 0.064 80 TBC 10 dispersant 20 (Note) Amount of the formation of fouling when no agent was added was 0.320 % by weight based on the total amount of the fluid.
- Comparative Examples 1 and 2 showed good results on the rate of suppression of the formation of fouling. However, p-nitro-o-cresol cannot be used practically because of the problem on handling.
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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
Description
- The present invention relates to a novel antifoulant for petrochemical processes. More particularly, it relates to an antifoulant for petrochemical processes which can effectively prevent formation of fouling in processes in a petrochemical plant, such as the rectification process in an ethylene plant.
- In a petrochemical plant, such as an ethylene plant, distillation of a fluid containing olefins, such as ethylene and propylene, and diolefins, such as butadiene, has been conducted. In a process of distillation of such a fluid, it is inevitable that the fluid is modified with heat to form sludge by heating, for example, in a preliminary heat exchanger or a reboiler and the sludge thus formed is adhered to the surface of heat transfer in the preliminary heat exchanger or the reboiler or to the surface of pipings to form fouling.
- As the mechanism of the formation of fouling, the following phenomena are known. In petrochemical processes, organic compounds which are easily oxidized, such as unsaturated hydrocarbons like olefins and diolefins, in process fluids are led to hydroperoxides by the dissolved oxygen. The hydroperoxides are then decomposed with heat, particularly in the presence of a substance having a catalytic activity, such as a metal, to form ketones, aldehydes, carboxylic acids and the like. These compounds are polymerized to form sludge of oligomers and polymers.
- Therefore, antioxidants, such as phenolic antioxidants and amine antioxidants, polymerization inhibitors, such as oxime inhibitors and nitroso inhibitors, dispersants to prevent formation of sludge and adherence of deposit, and agents in combinations of these agents, have heretofore been used in petrochemical processes as antifoulants for the purpose of preventing fouling described above. For examples, (1) an antifoulant comprising a combination of aniline and t-butylcatechol (Japanese Patent Publication Showa 59(1984)-24138, (2) an antifoulant comprising nitrosophenol (Japanese Patent Application Laid-Open No. Heisei 3(1991)-350147, (3) an antifoulant comprising a nitroso compound (Japanese Patent Publication Heisei 4(1992)-26639, and (4) an antifoulant comprising an amine compound (Japanese Patent Application Laid-Open No. Showa 64(1989)-13041, have been disclosed.
- However, because these antifoulants are added directly to a process, they have drawbacks that coloring of the product is caused, that unfavorable by-products are formed, and, moreover, that they are not easy to handle, are expensive and have insufficient effect of preventing fouling to cause problems in a continuous operation for a long time, such as for two years or longer.
- As described above, conventional antifoulants are not always satisfactory. Thus, development of an antifoulant for petrochemical processes which can be handled easily, is inexpensive, has no adverse effect on the process, shows excellent effect to prevent the formation of fouling, and enables continuous operation for a long time with good stability, has strongly been desired.
- The present invention accordingly has an object to provide an antifoulant for petrochemical processes which can eliminate the drawbacks of the conventional antifoulants for petrochemical processes, can be handled easily, is inexpensive, has no adverse effect on the process, shows excellent effect to prevent the formation of fouling, and enables continuous operation of a plant for a long time with good stability.
- The present inventors conducted extensive studies to develop an antifoulant for petrochemical processes having the advantageous properties described above. As the result of the studies, it was discovered that the object can be achieved by an antifoulant comprising a hydrogen-donating hydroaromatic compound. The present invention is completed on the basis of the discovery.
- Thus, the present invention provides an antifoulant for petrochemical processes comprising a hydrogen-donating hydroaromatic compound.
- The present invention also provides a process for preventing formation of fouling in a petrochemical plant comprising adding the antifoulant for petrochemical processes described above to a process fluid supplied to petrochemical processes in which fouling is formed.
- Other and further objects, features and advantages of the invention will appear more fully in the following description.
- The present invention is described in detail in the following.
- As described above, the formation of fouling is caused by oxidation of unsaturated hydrocarbons, such as olefins and diolefins, in a process fluid by radical chain reactions. The hydrogen-donating hydroaromatic compound used as the antifoulant of the present invention has the function of stopping the chain reactions by donating proton to the radical generated in the oxidation and effectively preventing the formation of fouling. Examples of the hydrogen-donating hydroaromatic compound include tetralin, 9,10-dihydrophenanthrene, 1,2,3,4,5,6,7,8-octahydro-phenanthrene, and hydrogenated terphenyl. The compound may be used singly or as a combination of two or more compounds.
- In the antifoulant of the present invention, conventional antifoulants, such as antioxidants like amine antioxidants and phenol antioxidants, polymerization inhibitors like oxime inhibitors and nitroso inhibitors, metal deactivating agents, and various kinds of dispersant, may be used in addition to the hydroaromatic hydrocarbon according to desire. The dispersant disperses organic sludge and inorganic sludge into the process fluid and prevents adherence of deposit to the surface of heat transfer or the surface of pipings. Examples of the dispersant include:
- (1) a mixture of a polyalkyl (meth)acrylate having molecular weight of about 1000 to 10000 and a polyethylene polyamine naphthenic acid amide represented by the following general formula:
- (2) a derivative of succinimide represented by one of the following general formulae:
- (3) a derivative of thiophosphoric acid ester represented by the following general formula;
- (4) a copolymer of styrene and maleic acid ester having a molecular weight of 10,000 to 1,000,000 and represented by the following general formula:
- Examples of the polyalkyl (meth)acrylate used in the dispersant (1) described above include homopolymer of an alkyl (meth)acrylate in which the alkyl group has 5 to 18 carbon atoms, copolymers obtained by copolymerization of two or more kinds of said alkyl (meth)acrylate, and copolymers obtained by copolymerization of one or more kinds of said alkyl (meth)acrylate with one or more kinds of unsaturated monomer having an ethylenically unsaturated bond, such as N-vinyl-2-pyrrolidone and diethylaminoethyl (meth)acrylate.
- Amounts of the components used according to desire in the antifoulant, such as the antioxidant, the polymerization inhibitor, the metal deactivating agent, and the dispersant, are not particularly limited but suitably selected.
- The process fluid to which the antifoulant of the present invention is applied is not particularly limited. The antifoulant of the present invention can be applied to any kind of oil for treatment in which fouling is formed in treatments in petrochemical processes. It is preferably applied to process oils treated in a preliminary heat exchanger or a reboiler in a distillation tower, such as a depropanizer, a de-ethanizer, a debutanizer, or a condensate stripper, in an ethylene plant.
- An example of the preferable method of application of the antifoulant of the present invention is described in the following. The hydrogen-donating hydroaromatic compound and other components, such as other antifoulants and additional components, which are used additionally according to necessity are dissolved in a suitable solvent to prepare a solution having a concentration of about 0.5 to 60 % by weight. The solution thus prepared is added continuously to an apparatus in which fouling is formed in the petrochemical process, such as a heat exchanger, a reboiler or pipings or added to the tank of a material oil in all the amount at one time. The amount of the antifoulant of the present invention added to the process fluid is selected generally in the range of 0.5 to 50000 mg/liter, preferably 30 to 200 mg/liter, based on the amount of the process fluid.
- Because the antifoulant of the present invention has the excellent property to prevent the formation of fouling, continuous operation for a long time, such as for two to three years, is made possible with good stability, in contrast to continuous operation generally practiced for only 3 months when a conventional antifoulant is used. As the result, energy saving and reduction of maintenance cost can be expected and, furthermore, risk accompanied with emergency stopping of the plant can be avoided.
- To summarize the advantages obtained by the invention, the antifoulant for petrochemical processes can be handled easily, is inexpensive, has no adverse effect on the process, shows excellent effect to prevent formation of fouling, enables continuous operation of a plant for a long time with good stability and brings energy saving and reduction of maintenance cost.
- The invention will be understood more readily with reference to the following examples; however, these examples are intended to illustrate the invention and are not to be construed to limit the scope of the invention.
- Agents of the kinds and the amounts shown in Table 1 were added to a depropanizer bottom fluid taken from a plant in operation. The mixture was charged to a 200 milliliter autoclave made of SUS 304 and treated with heat at 100°C for 20 hours. Then, the treated fluid is distilled under a reduced pressure and dried to obtain amount of the residue of evaporation (amount of formed polymer). Rate of suppression of the formation of fouling was calculated for evaluation of the anti-fouling property as the ratio of the value obtained above to the corresponding value obtained in the absence of the agent. Results are shown in Table 1.
- In Table 1, the dispersant is a copolymer of styrene and a maleic acid ester having a molecular weight of 15000 and TBC indicates t-butylcatechol.
Table 1 agent amount of formed polymer (% by wt. of the total fluid) rate of suppression (%) kind amount used (mg/kg) Example 1 tetralin 10 0.030 90 Example 2 tetralin 20 0.026 92 Example 3 tetralin 10 0.006 98 dispersant 10 Example 4 tetralin 20 0.003 99 dispersant 20 Example 5 9,10-dihydrophenanthrene 20 0.004 99 dispersant 20 Example 6 hydrogenated terphenyl 10 0.004 99 dispersant 20 Comparative Example 1 p-nitro-o-cresol 10 0.016 95 Comparative Example 2 p-nitro-o-cresol 20 0.006 98 Comparative Example 3 aniline 5 0.096 70 TBC 5 dispersant 10 Comparative Example 4 aniline 10 0.064 80 TBC 10 dispersant 20 (Note) Amount of the formation of fouling when no agent was added was 0.320 % by weight based on the total amount of the fluid. - Comparative Examples 1 and 2 showed good results on the rate of suppression of the formation of fouling. However, p-nitro-o-cresol cannot be used practically because of the problem on handling.
Claims (11)
- An antifoulant for petrochemical processes comprising a hydrogen-donating hydroaromatic compound.
- An antifoulant for petrochemical processes as claimed in Claim 1, wherein the hydrogen-donating hydroaromatic compound is a compound selected from the group consisting of tetralin, 9, 10-dihydrophenanthrene, 1,2,3,4,5,6,7,8-octahydrophenanthrene and a hydrogenated terphenyl.
- An antifoulant for petrochemical processes as claimed in Claim 1, wherein the antifoulant contains a dispersant for sludge.
- An antifoulant for petrochemical processes as claimed in Claim 3, wherein the dispersant for sludge is at least one selected from the group consisting of a mixture of a polyalkyl (meth)acrylate and a polyethylene polyamine naphthenic acid amide, a derivative of succinimide, a derivative of a thiophosphoric acid ester or an ethylene oxide adduct thereof, and a copolymer of styrene and a maleic acid ester.
- A process for preventing formation of fouling in a petrochemical plant comprising adding the antifoulant for petrochemical processes described in Claim 1 to a process fluid supplied to petrochemical processes in which fouling is formed.
- A process for preventing formation of fouling in a petrochemical plant as claimed in Claim 5, wherein the antifoulant for petrochemical processes is added to the process fluid in an amount in the range of 0.5 to 50,000 mg/liter.
- A process for preventing formation of fouling in a petrochemical plant as claimed in Claim 5, wherein the antifoulant for petrochemical processes is added continuously to the process fluid at a position before the apparatus in a petrochemical plant in which apparatus the fouling is formed.
- A process for preventing formation of fouling in a petrochemical plant as claimed in Claim 5, wherein the antifoulant for petrochemical processes is added to a material tank of the process fluid in a petrochemical plant.
- A process for preventing formation of fouling in a petrochemical plant as claimed in Claim 5, wherein the petrochemical plant is an ethylene plant.
- A process for preventing formation of fouling in a petrochemical plant as claimed in Claim 5, wherein the antifoulant contains a dispersant for sludge.
- A process for preventing formation of fouling in a petrochemical plant as claimed in Claim 10, wherein the dispersant for sludge is at least one selected from the group consisting of a mixture of a polyalkyl (meth)acrylate and a polyethylene polyamine naphthenic acid amide, a derivative of succinimide, a derivative of a thiophosphoric acid ester or an ethylene oxide adduct thereof, and a copolymer of styrene and a maleic acid ester.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP18924993 | 1993-07-01 | ||
JP189249/93 | 1993-07-01 | ||
JP5189249A JPH0718265A (en) | 1993-07-01 | 1993-07-01 | Antifouling agent for petrochemical process |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0632121A2 true EP0632121A2 (en) | 1995-01-04 |
EP0632121A3 EP0632121A3 (en) | 1995-05-17 |
EP0632121B1 EP0632121B1 (en) | 2000-03-01 |
Family
ID=16238133
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP94109954A Expired - Lifetime EP0632121B1 (en) | 1993-07-01 | 1994-06-28 | An antifoulant for petrochemical processes |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0632121B1 (en) |
JP (1) | JPH0718265A (en) |
KR (1) | KR0140052B1 (en) |
CN (1) | CN1110534C (en) |
BR (1) | BR9402609A (en) |
DE (1) | DE69423140T2 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009120653A2 (en) * | 2008-03-24 | 2009-10-01 | Baker Hughes Incorporated | Method for reducing acids in crude or refined hydrocarbons |
US9434844B2 (en) | 2011-10-12 | 2016-09-06 | Ineos Europe Ag | Additive, composition comprising it and use thereof |
WO2018156914A1 (en) * | 2017-02-27 | 2018-08-30 | Ecolab USA, Inc. | Anti-foulant formulation for compressors |
US11015135B2 (en) | 2016-08-25 | 2021-05-25 | Bl Technologies, Inc. | Reduced fouling of hydrocarbon oil |
US12031096B2 (en) | 2021-04-06 | 2024-07-09 | Bl Technologies, Inc. | Reduced fouling of hydrocarbon oil |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
EP2498097B1 (en) | 2009-11-04 | 2016-09-28 | Hitachi High-Technologies Corporation | Cover opener and automatic analyzing device using same |
KR102374179B1 (en) * | 2017-05-09 | 2022-03-14 | 카타야마 케미칼, 인코포레이티드 | 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 |
EP4065664A1 (en) * | 2019-11-27 | 2022-10-05 | Ecolab USA Inc. | Anti-fouling compositions for use in crude oil production and processing |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0156614A2 (en) * | 1984-03-20 | 1985-10-02 | Gulf Canada Resources Limited | Coking residuum in the presence of hydrogen donor |
WO1991017230A1 (en) * | 1990-05-02 | 1991-11-14 | 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 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1291057C (en) * | 1986-12-19 | 1991-10-22 | Junichi Kubo | Method for hydrocracking heavy fraction oils |
-
1993
- 1993-07-01 JP JP5189249A patent/JPH0718265A/en active Pending
-
1994
- 1994-06-28 DE DE69423140T patent/DE69423140T2/en not_active Expired - Fee Related
- 1994-06-28 EP EP94109954A patent/EP0632121B1/en not_active Expired - Lifetime
- 1994-06-30 BR BR9402609A patent/BR9402609A/en not_active Application Discontinuation
- 1994-06-30 KR KR1019940015379A patent/KR0140052B1/en not_active IP Right Cessation
- 1994-07-01 CN CN94107845A patent/CN1110534C/en not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0156614A2 (en) * | 1984-03-20 | 1985-10-02 | Gulf Canada Resources Limited | Coking residuum in the presence of hydrogen donor |
WO1991017230A1 (en) * | 1990-05-02 | 1991-11-14 | 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 |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009120653A2 (en) * | 2008-03-24 | 2009-10-01 | Baker Hughes Incorporated | Method for reducing acids in crude or refined hydrocarbons |
WO2009120653A3 (en) * | 2008-03-24 | 2009-11-26 | Baker Hughes Incorporated | Method for reducing acids in crude or refined hydrocarbons |
US9200213B2 (en) | 2008-03-24 | 2015-12-01 | Baker Hughes Incorporated | Method for reducing acids in crude or refined hydrocarbons |
US9434844B2 (en) | 2011-10-12 | 2016-09-06 | Ineos Europe Ag | Additive, composition comprising it and use thereof |
US11015135B2 (en) | 2016-08-25 | 2021-05-25 | Bl Technologies, Inc. | Reduced fouling of hydrocarbon oil |
WO2018156914A1 (en) * | 2017-02-27 | 2018-08-30 | Ecolab USA, Inc. | Anti-foulant formulation for compressors |
US10745345B2 (en) | 2017-02-27 | 2020-08-18 | Ecolab Usa Inc. | Anti-foulant formulation for compressors |
US11186540B2 (en) | 2017-02-27 | 2021-11-30 | Ecolab Usa Inc. | Anti-foulant formulation for compressors |
US12031096B2 (en) | 2021-04-06 | 2024-07-09 | Bl Technologies, Inc. | Reduced fouling of hydrocarbon oil |
Also Published As
Publication number | Publication date |
---|---|
EP0632121A3 (en) | 1995-05-17 |
JPH0718265A (en) | 1995-01-20 |
KR950003422A (en) | 1995-02-16 |
KR0140052B1 (en) | 1998-06-15 |
DE69423140D1 (en) | 2000-04-06 |
DE69423140T2 (en) | 2000-08-24 |
BR9402609A (en) | 1995-04-04 |
EP0632121B1 (en) | 2000-03-01 |
CN1102848A (en) | 1995-05-24 |
CN1110534C (en) | 2003-06-04 |
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