CN1423625A - Process for the production of gasoline stocks - Google Patents
Process for the production of gasoline stocks Download PDFInfo
- Publication number
- CN1423625A CN1423625A CN01808163A CN01808163A CN1423625A CN 1423625 A CN1423625 A CN 1423625A CN 01808163 A CN01808163 A CN 01808163A CN 01808163 A CN01808163 A CN 01808163A CN 1423625 A CN1423625 A CN 1423625A
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- Prior art keywords
- hydrogen
- reactor
- distillation column
- oligopolymer
- hydrocarbon
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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
- C10G69/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process
- C10G69/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only
- C10G69/12—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one polymerisation or alkylation step
- C10G69/126—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one polymerisation or alkylation step polymerisation, e.g. oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for the production of gasoline stocks wherein lower molecular weight olefins (line 102) are first oligomerized and the oligomers (line 105) hydrogenated is disclosed. In the first instance the oligomerization is carried out in a single pass fixed bed boiling point reactor (10). The oligomers (line 105) are then hydrogenated in a distillation column reactor (20).
Description
Background of invention
Invention field
The present invention relates generally to a kind of method of producing gasoline boiling range raw material from low boiling point olefin.More specifically, the present invention relates to a kind of with C
3-C
5Alkene carries out the oligomeric C for preparing
8-C
9Alkene obtains its hydrogenation the method for desirable gasoline blending stock then.
Correlation technique
At USP3,960,978 and 4,021, disclosing conversion of olefines in 502 is gasoline and/or distillate product, wherein is converted into the olefinic gasoline blending stock by alkene is contacted with the catalyst bed of being made by ZSM-5 type zeolite being in gaseous olefin in ethene-amylene scope (separately or with the mixture of paraffin).At USP4, in 227,992, Garwood and Lee disclose and have been used for C
3+ alkene mainly is selectively converted to the operational condition of aliphatic hydrocarbon.At USP4, also disclosing conversion of olefines in 150,062 and 4,211,640 is the method for gasoline component.At USP5, in 608,133, people such as Chang disclose by with C
2-C
5Olefin oligomerization is carried out hydrogenation and is produced synthetic lubricant higher alkene subsequently.At USP5, a kind of liquid phase oligomerisation C is disclosed in 003,124
4And C
5The method of isoolefine wherein makes reaction mixture boiling removing reaction heat, and in one embodiment, also has further dimerization in reactive distillation column.
At USP5, in 510,555, people such as Brunelli disclose two kinds of isomer of diisobutylene, 2,4,4-2,4,4-Trimethyl-1-pentene and 2,4,4-trimethylammonium-2-amylene generates 2 under the situation that both all are hydrogenated, 2, the 4-trimethylpentane, it is the standard substance that is used to measure octane value, promptly, RON=100, MON=100.
Summary of the invention
In brief, the present invention includes the oligomeric of light alkene and the hydrogenation of this oligopolymer subsequently.Oligomeric preferably in boiling point reactors, under the condition that helps dimerization (opposite), carry out with the long-chain oligopolymer, wherein, reaction mixture absorbs the latent heat of vaporization and controlled temperature by being seethed with excitement.If necessary, the ejecta of boiling point reactors can be fed to the distillation column reactor to guarantee the alkene complete reaction.The catalyzer that is used for oligomerization comprises acidic cation-exchange resin or zeolite.
Then, preferably in reaction distillation with the dipolymer hydrogenation that produces in the oligomerization.Dipolymer can be lower than 70psia at least about 0.1psia-, as the available hydrogen branch that is lower than 50psia is depressed with hydrogen stream and fed reactive distillation column.The reaction distillation column type reactor comprises hydrogenation catalyst, and it is the integral part of distillation structure, selectively hydrogenation part dipolymer.In defined hydrogen dividing potential drop, the hydrogen of use needn't be more than keeping catalyzer and the necessary hydrogen of hydrogenated olefinic compound, because excessive hydrogen will be discharged from usually.Typical hydrogenation catalyst is the group VIII metal that is stated from alumina-based, comprising platinum, nickel and cobalt etc.
Term " reaction distillation " is used for being described in parallel reaction and rectifying in the post.For the purposes of the present invention, term " catalytic distillation " comprise reaction distillation and in a post parallel any reaction and fractionated other method, no matter what kind of name it uses.
Be used for catalyst bed of the present invention and can be described as fixed bed, the meaning is the bed that places this reaction column FX, comprises the expanded bed and the fluidized-bed of catalyzer.Catalyzer in the bed can be identical or different, as long as they can realize described hydride functional.The catalyzer that is prepared into the distillation member is effective especially in the present invention.
The accompanying drawing summary
Accompanying drawing is the block diagram of one embodiment of the invention.
Detailed Description Of The Invention
Can oligomeric alkene among the present invention comprise propylene, butylene and amylene, particularly isobutene, Iso-amylene and linear alpha-olefin. Typically, the C of interior straight chain4And C5Alkene than the α of same carbon number-The reactivity of alkene or isoalkene is lower.
We comprise by interested oligomerization:
(1) propylene+isobutene=＞heptene
(2) isobutene+isobutene=＞diisobutylene
(3) n-butene+iso-butylene=＞octene
(4) isopentene+propylene=＞octene
(5) isopentene+butylene=＞nonene
Then, higher alkene hydrogenation is prepared into the alkane that can be used as gasoline blending stock.The dimerization of iso-butylene itself is that we are interested especially, because during hydrogenation, the isomer of any diisobutylene all can produce pure isooctane (octane-iso).The reactive behavior of tertiary olefin is higher, and the oligopolymer of inclined form dipolymer, some copolymerization dipolymers and Geng Gao.
Oligomerization is preferably in boiling point reactors, at the acid particles catalyzer, as carrying out under the existence of acidic cation-exchange resin or zeolite, reaction pressure remains on its boiling point for being enough to reaction mixture, in the 120F-300F scope, at least a portion but not every reaction mixture is vapour phase in the case.This reactor and method be at USP5, is described in 003,124, and it is hereby incorporated by.
Given composition, reaction mixture will have different boiling points under different pressure, therefore can the temperature in the reactor be controlled in the temperature range of requirement by regulating pressure.Like this, the boiling point of reaction mixture is exactly a temperature of reaction, and the heat that reaction is emitted is consumed by evaporation reaction mixture.Any top temperature that is heated liquid composition will be the boiling point of composition under the setting pressure, and heat in addition only can make composition seethe with excitement more.Controlled temperature also uses identical principle among the present invention.But, must exist liquid so that boiling to be provided, otherwise the temperature in the reactor will rise continuously up to the infringement catalyzer.For avoiding to evaporate the heat release of all reaction mixtures, be necessary that the amount of alkene of raw material is limited in about 60% of total material in the reactor being fed into.The present invention can be used to comprise the logistics of any different alkene or its mixture.Controlled temperature is to prevent to form trimer and heavier product carefully.Boiling point reactors itself can carry out this control well.
Catalyst bed in the boiling point reactors can be described as fixedly successive bed, that is to say, catalyzer is loaded in the reactor with filling reactor or reaction zone with particle form, although one or more this successive bed can be arranged in the reactor, they can be separated by the spacing of catalyst-free and come.
Resin or zeolite catalyst are loaded in the local liquid phase boiling point reactors as the fixed bed particle.Reaction raw materials is with the described bed of liquid form feeding.Described bed can be a level, vertical or tilted-putted.Preferred described bed is vertical with the raw material that passes through by this and after reaction downwards to discharge the reactor lower end.Reactor is in high liquid hourly space velocity (5-20LHSV, preferred 10-20) operation down, to avoid the polymerization of reversed reaction and alkene.These conditions can produce the olefin conversion of about 80-90%, may need two or more reactors in series to obtain required alkene total conversion rate.
Can be by conventional distillation with oligomerization product and reactants separate, oligomer product discharged with the form of bottoms and at the unreacted raw material of recovered overhead.Perhaps, the distillation column reactor that the feeding of the ejecta of boiling point reactors can be comprised identical or similar catalyzer to be obtaining required transformation efficiency, and simultaneously product separated with unreacted raw material.
Then oligopolymer is fed hydrogenation zone, preferred package contains the distillation column reactor of hydrogenation catalyzer.The catalytic specie that is used for hydrogenation process preferably is the form that can be used as the distillation filler.A lot of places are all mentioned, and catalytic specie is the integral part of distillation function system, and it is both as catalyzer, again as the distillation filler, that is, and as not only having the distillation function but also having the filler of the distillation column of catalysis.Catalyzer is prepared to the form of catalytic distillation structure.More specifically, hydrogenation catalyst generally contains and is stated from the group VIII metal that is on extrudate or the spheric alumina carrier, extrudate or bead are placed in the porous container and suitably load in the distillation column reactor to allow steam can flow through this bed, also provide enough surface-area to be used for catalytic Contact simultaneously.
Wherein, the known metal that is used for the catalytic hydrogenation catalyzer is platinum, rhenium, cobalt, molybdenum, nickel, tungsten and palladium.Generally, the oxide compound of these metals of the commercial form working load of catalyzer.Perhaps before using, use reductive agent, perhaps in use oxide compound is reduced to activity form by the hydrogen in the raw material.The dehydrogenation under the high temperature is it should be noted that in also other the reaction of catalysis of these metals most.
Because catalyzer keeps an independently integral body, so reaction system can be known as the out-phase reaction system again.Can use any suitable hydrogenation catalyst, for example periodic table of elements group VIII metal is as main catalyst component, it uses separately or uses with promotor and properties-correcting agent, as porpezite, palladium-silver, cobalt/zirconium, preferred deposition is as aluminium sesquioxide, firebrick, float stone, carbon, silicon-dioxide, the nickel on the carriers such as resin.
For the temperature and the residence time are controlled within the required range, a kind of method and apparatus is provided, wherein distillation column reactor internal reaction liquid is boiling state.Overhead product is taken out and condensation, and some condensation products turn back in the distillation column reactor as phegma.The advantage of present method is, because continuous backflow, a part of selecteed oligopolymer is everlasting and condensation is taken place on the catalyst structure.
In the distillation column reactor, we believe that the validity of hydride process may come from the condensation of part steam in the reaction system, wherein in phlegma, be mingled with enough hydrogen in order to obtaining in the presence of the catalyzer essential close contact the between the hydrogen and selected oligopolymer, thereby cause their hydrogenation.The exothermic heat of reaction of a great deal of is removed in the evaporation of liquid material.Because liquid is in boiling temperature in the reactor, so can come controlled temperature by control pressure, pressure increases, and temperature increases, and pressure reduces, and temperature also reduces.
Several different layouts are disclosed in order to obtain desirable effect.For example, English Patent 2,096,603 and 2,096,604 disclose catalyzer have been placed on the charging tray general in the distillation column.A series of United States Patent (USP)s, comprise listed above those, USP4 particularly, 443,559 and 4,215,011, the catalyzer that uses as packed distillation column part filler is disclosed.A plurality of use also is known in the reactive distillation column, in for example USP4,950,834; 5,321,163; With 5,595, be illustrated in 634.
The catalyst structure that is fit to of the described oligopolymer of a kind of hydrogenation comprises a bundle flexibility at least, semi-rigid open tubular element, particulate state catalytic specie (catalyst component) wherein is housed, two ends all seal, with have the scroll of being coiled into, it is closely linked and be supported by it to have the wire mesh screen of the longitudinal axis, described tube element is arranged with certain angle with respect to the longitudinal axis, form a bundle thus, this element is specified in the USP5 that this paper quotes, 431, in 890, the flexibility of particulate state catalytic specie abrim wherein, semi-rigid open tubular element preferably has a snap ring to form the catalytic distillation structure of multiple connection shape along the every 1-20 inch of pipe range direction, can even or irregular spacing by the link that snap ring forms.Bundle shape catalytic distillation structure is by at least one tube element is placed wire mesh screen along the diagonal lines arrangement mode, form as demister top wiry, like this when rolling wire mesh screen, curling member will provide new and improved catalytic distillation structure.
Other embodiments comprise wire mesh screen and are rolled into many arrangements of tube element alternative of new bundle shape catalytic distillation structure.Tube element preferred arrangement on the interbedded formation is online at reciprocal wire screen, and their path will interlock like this.Each tube element is fixed in bundle and is scroll.
Catalyst component can be several forms.At it is under the situation of particulate state catalytic specie, generally with 60 millimeters-Yue below 1 millimeter up to the catalyzer of the powder porous container of packing into, in screen wires or polymkeric substance sieve.The material that is used to prepare container must be inertia for reactant and reaction system condition.Screen wires can be aluminium, steel, stainless steel etc.The polymkeric substance sieve can be nylon, special teflon etc.Be used to prepare container material mesh or threads per inch should make catalyzer remain on wherein and can be by the opening of this material.Although can use the granules of catalyst or the catalyst fines of about 0.15 millimeter size, operable particle diameter is up to about 1/4 inch in the container.
It is alkane that reaction conditions in the distillation column reactor must be enough to olefin hydrogenation.Only the pressure and temperature condition of hydrogenated diene hydrocarbon is for example 150 °F to top temperature 170-200 °F, and pressure is 10-75psig.The hydrogenation monoolefine then needs exacting terms more, and 200-350 °F, 30-150psig.
Now, with reference to the accompanying drawings, the simplification flow process of one embodiment of the invention is described.To contain one or more will carry out oligomeric olefin feedstock and be fed in the boiling point reactors 10 that comprises catalyst bed 12 described catalyzer or acidic ion exchange resin or zeolite via flowline 102.In boiling point reactors, alkene and itself are reacted or the reaction generation is than the oligopolymer (mainly being dipolymer) of long-chain each other, and it is shifted out by reactor via flowline 105 and enters into distillation column reactor 20.
Distillation column reactor 20 comprises the hydrogenation catalyst bed 22 that is suitable for as the distillation member.Oligopolymer, for example dipolymer, or at least a portion oligopolymer are hydrogenated to having more high boiling corresponding alkane, and this alkane is removed as bottoms via flowline 108.By the condition of keep-uping pressure dipolymer is remained in the catalyst zone 22, thereby with the complete hydrogenation of dipolymer.Unreacted alkene monomer, alkane and hydrogen are removed as overhead product via flowline 106 in the raw material.Overhead product condensation in condenser 114, and in separator 116, collect.Hydrogen is removed via pipeline 110, and it can be recycled in the flowline 104.The hydrocarbon of part condensation returns via flowline 108 as reflux, and a part is removed via flowline 112, and this part can be recycled in the flowline 102.On catalyst bed 22, provide and contain standard distillation member, as the rectification zone 24 of charging tray or filler.Equally, provide stripping zone 26 below 22 at catalyst bed.
Though other embodiment that does not illustrate but be contemplated as falling with among the present invention comprises the many boiling point reactors or the boiling point reactors distillation column reactor afterwards that can obtain desirable olefin conversion.
Embodiment
Under 90 °F, comprise 14.2wt% iso-butylene, 72.7wt% mainly by C
3And C
5Other C of hydrocarbon equilibrated
4Raw material, with the liquid hourly space velocity 10 Amberlyst 15 microballoon fixed beds of flowing through downwards, obtaining conversion for isobutene is more than 85%.
Total ejecta of reaction is sent into the top of catalyst zone, it is one inch post that described catalyst zone is arranged in a diameter, and this post is being adorned 10 feet, and as the hydrogenation catalyst of distillation member, this catalyzer is stated from 1/8 by the Pd of 0.5wt% " Al
2O
3Make on (aluminium sesquioxide) extrudate (Calsicat E144SDU).2 feet the stripping zone that contains Pall ring is positioned at the below of catalyst bed.Total pressure is 75psig, and temperature is 175 °F, and LHSV is 10.Heavier oligopolymer drips in the catalyst zone, and there, it contacts with the hydrogen of being sent into below by catalyst zone, depresses basically at the hydrogen branch of 10psig all oligopolymer (mainly being dipolymer) are converted into alkane, and this alkane reclaims as bottoms.Overhead product is C
3And C
4And C
5Hydrocarbon also has unreacted hydrogen.
Claims (9)
1. a method that is used to produce gasoline component may further comprise the steps: by make C under oligomeric condition
3-C
5Alkene contacts with acid catalyst in local at least liquid phase and makes C
3-C
5Olefin oligomerization, and under parallel hydrogenation and distillatory condition, the gained oligopolymer is contacted with hydrogen with hydrogenation catalyst.
2. according to the process of claim 1 wherein that the hydrogen dividing potential drop of using is 0.1-70psia.
3. according to the process of claim 1 wherein that liquid hourly space velocity is 5-20 in the oligomerization step.
4. according to the method for claim 3, wherein liquid hourly space velocity is 10-20 in the oligomerization step.
5. according to the process of claim 1 wherein that described alkene comprises iso-butylene, described oligopolymer comprises 2,4,4-2,4,4-Trimethyl-1-pentene and 2,4, and 4-trimethylammonium-2-amylene, described alkane comprises pure isooctane.
6. a method of producing gasoline component comprises the steps:
(a) will contain C
3-C
5The hydrocarbon stream feeding of alkene contains the one way down-type fixed-bed reactor of acidic oligomeric catalyst, and the boiling point of the mixture in described reactor of the temperature maintenance in the wherein said reactor makes the described C of at least a portion thus
3-C
5Alkene reacts each other or forms oligopolymer with itself reaction;
(b) ejecta and the hydrogen with described one way down-type fixed-bed reactor is fed in the distillation column reactor that contains hydrogenation catalyst in the distillation reaction district;
(c) in described distillation reaction district, carry out following processing step simultaneously:
(i) described oligopolymer is contacted in the presence of described hydrogenation catalyst with described hydrogen, being corresponding alkane with the described oligopolymer hydrogenation of part; With
(ii) by the corresponding alkane of fractionation separates; With
(d) from described distillation column reactor, shift out described alkane at the position that is lower than described distillation reaction district.
7. according to the method for claim 6, wherein said hydrogen reclaims and is recycled to the described distillation column reactor from overhead product.
8. according to the method for claim 7, wherein being different from other hydrocarbon of corresponding alkene and hydrogen shifts out from described distillation column reactor with the form of overhead product, and so that described other hydrocarbon is separated with hydrogen, described other hydrocarbon is recycled in the described distillation column reactor as reflux with described overhead product cooling.
9. a method of producing gasoline component comprises the steps:
(a) will contain C
3-C
5The hydrocarbon stream feeding of alkene contains the one way down-type fixed-bed reactor of the acid resin catalyst of positively charged ion, and the boiling point of the mixture in described reactor of the temperature maintenance in the wherein said reactor makes the described C of at least a portion thus
3-C
5Alkene reacts each other or forms oligopolymer with itself reaction;
(b) will comprise in the distillation column reactor of the hydrogenation catalyst that contains the group VIII metal in the ejecta of described one way down-type fixed-bed reactor and the hydrogen feeding distillation reaction district;
(c) in described distillation reaction district, carry out following processing step simultaneously:
(i) described oligopolymer is contacted in the presence of described hydrogenation catalyst with described hydrogen, being corresponding alkane with the described oligopolymer hydrogenation of part; With
(ii) corresponding alkane is separated with hydrogen with other hydrocarbon by fractionation; With
(d) from described distillation column reactor, shift out corresponding alkane at the position that is lower than described distillation reaction district.
(e) from described distillation column, remove described other hydrocarbon and hydrogen with the overhead product form;
(f) the described overhead product of cooling is to separate described other hydrocarbon with described hydrogen; With
(g) described other hydrocarbon of part is recycled in the described distillation column reactor as reflux.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55752300A | 2000-04-24 | 2000-04-24 | |
| US09/557,523 | 2000-04-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1423625A true CN1423625A (en) | 2003-06-11 |
| CN100445242C CN100445242C (en) | 2008-12-24 |
Family
ID=24225759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB018081630A Expired - Fee Related CN100445242C (en) | 2000-04-24 | 2001-04-03 | Process for the production of gasoline stocks |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1280745A4 (en) |
| JP (1) | JP2003531254A (en) |
| KR (1) | KR100765669B1 (en) |
| CN (1) | CN100445242C (en) |
| AU (1) | AU2001253895A1 (en) |
| CA (1) | CA2407035A1 (en) |
| MX (1) | MX258626B (en) |
| PL (1) | PL357048A1 (en) |
| WO (1) | WO2001081278A1 (en) |
| ZA (1) | ZA200208087B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114395077A (en) * | 2021-12-28 | 2022-04-26 | 恒河材料科技股份有限公司 | Preparation method of naphthenic filling oil |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1388528B1 (en) | 2002-08-06 | 2015-04-08 | Evonik Degussa GmbH | Process for the oligomerisation of isobutene contained in hydrocarbon streams containing n-butene |
| US7145049B2 (en) * | 2003-07-25 | 2006-12-05 | Catalytic Distillation Technologies | Oligomerization process |
| JP4608341B2 (en) * | 2005-03-04 | 2011-01-12 | 出光興産株式会社 | Method for producing gasoline base material |
| FR2885137B1 (en) * | 2005-04-28 | 2007-07-13 | Inst Francais Du Petrole | PROCESS FOR THE DESULFURATION OF OLEFINIC ESSENCES |
| CN105777472B (en) * | 2016-04-15 | 2018-01-23 | 河北工业大学 | It is a kind of to separate pentane, hexane, heptane and the method for octane mixture system |
| CN108218654A (en) * | 2018-02-12 | 2018-06-29 | 安徽海德化工科技有限公司 | A kind of method that isooctane is prepared using isobutanol |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4334113A (en) * | 1980-06-11 | 1982-06-08 | Gulf Research & Development Company | Synthetic hydrocarbon oligomers |
| US4720600A (en) * | 1983-06-29 | 1988-01-19 | Mobil Oil Corporation | Production of middle distillate range hydrocarbons by light olefin upgrading |
| GB8502034D0 (en) * | 1985-01-28 | 1985-02-27 | Emi Plc Thorn | Discharge lamps |
| US5792428A (en) * | 1994-07-18 | 1998-08-11 | Chemical Research & Licensing Company | Apparatus for conducting exothermic reactions |
| US5608133A (en) * | 1995-10-23 | 1997-03-04 | Mobil Oil Corporation | Catalytic oligomerization |
| FR2743079B1 (en) * | 1995-12-27 | 1998-02-06 | Inst Francais Du Petrole | PROCESS AND DEVICE FOR SELECTIVE HYDROGENATION BY CATALYTIC DISTILLATION INCLUDING A LIQUID-GAS UPWARD CO-CURRENT REACTION ZONE |
| US5877372A (en) * | 1997-11-21 | 1999-03-02 | Arco Chemical Technology, L.P. | Isobutylene oligomerization using isooctane diluent |
| KR100558972B1 (en) * | 2002-12-30 | 2006-03-10 | 주식회사 효성 | Preparation method of 1,5-dimethyltetralin |
-
2001
- 2001-04-03 KR KR1020027013927A patent/KR100765669B1/en not_active IP Right Cessation
- 2001-04-03 JP JP2001578376A patent/JP2003531254A/en active Pending
- 2001-04-03 CN CNB018081630A patent/CN100445242C/en not_active Expired - Fee Related
- 2001-04-03 EP EP01927448A patent/EP1280745A4/en not_active Withdrawn
- 2001-04-03 PL PL01357048A patent/PL357048A1/en not_active Application Discontinuation
- 2001-04-03 WO PCT/US2001/040522 patent/WO2001081278A1/en active Application Filing
- 2001-04-03 AU AU2001253895A patent/AU2001253895A1/en not_active Abandoned
- 2001-04-03 CA CA002407035A patent/CA2407035A1/en not_active Abandoned
- 2001-04-03 MX MXPA02010489 patent/MX258626B/en active IP Right Grant
-
2002
- 2002-10-08 ZA ZA200208087A patent/ZA200208087B/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114395077A (en) * | 2021-12-28 | 2022-04-26 | 恒河材料科技股份有限公司 | Preparation method of naphthenic filling oil |
| CN114395077B (en) * | 2021-12-28 | 2024-02-09 | 恒河材料科技股份有限公司 | Preparation method of cycloalkyl filling oil |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1280745A4 (en) | 2004-08-18 |
| EP1280745A1 (en) | 2003-02-05 |
| KR100765669B1 (en) | 2007-10-10 |
| MXPA02010489A (en) | 2003-03-10 |
| JP2003531254A (en) | 2003-10-21 |
| KR20020087494A (en) | 2002-11-22 |
| AU2001253895A1 (en) | 2001-11-07 |
| WO2001081278A1 (en) | 2001-11-01 |
| PL357048A1 (en) | 2004-07-12 |
| ZA200208087B (en) | 2003-07-23 |
| CA2407035A1 (en) | 2001-11-01 |
| MX258626B (en) | 2008-07-09 |
| CN100445242C (en) | 2008-12-24 |
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