AU634740B2 - Adsorbent for purifying olefins - Google Patents

Adsorbent for purifying olefins Download PDF

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Publication number
AU634740B2
AU634740B2 AU47973/90A AU4797390A AU634740B2 AU 634740 B2 AU634740 B2 AU 634740B2 AU 47973/90 A AU47973/90 A AU 47973/90A AU 4797390 A AU4797390 A AU 4797390A AU 634740 B2 AU634740 B2 AU 634740B2
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Prior art keywords
alumina
compound
hydroxide
adsorbent
previous
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AU47973/90A
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AU4797390A (en
Inventor
Claude-Bernard Cartier
Eric Garcin
Eric Quemere
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IFP Energies Nouvelles IFPEN
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Rhone Poulenc Chimie SA
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Application filed by Rhone Poulenc Chimie SA filed Critical Rhone Poulenc Chimie SA
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Assigned to INSTITUT FRANCAIS DU PETROLE reassignment INSTITUT FRANCAIS DU PETROLE Alteration of Name(s) in Register under S187 Assignors: RHONE-POULENC CHIMIE
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/04—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising compounds of alkali metals, alkaline earth metals or magnesium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/04—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising compounds of alkali metals, alkaline earth metals or magnesium
    • B01J20/041—Oxides or hydroxides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/04—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising compounds of alkali metals, alkaline earth metals or magnesium
    • B01J20/046—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising compounds of alkali metals, alkaline earth metals or magnesium containing halogens, e.g. halides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/06—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising oxides or hydroxides of metals not provided for in group B01J20/04
    • B01J20/08—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising oxides or hydroxides of metals not provided for in group B01J20/04 comprising aluminium oxide or hydroxide; comprising bauxite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28054—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J20/28057—Surface area, e.g. B.E.T specific surface area
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/3078—Thermal treatment, e.g. calcining or pyrolizing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
    • B01J20/3204—Inorganic carriers, supports or substrates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3234—Inorganic material layers
    • B01J20/3236—Inorganic material layers containing metal, other than zeolites, e.g. oxides, hydroxides, sulphides or salts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Water Supply & Treatment (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)

Description

COMMONWEALTH OF AUSTRALIA 634740 FORM PATENTS ACT 1952 COMPLETE SPECIFICATION FOR OFFICE USE: Class Int.Class Application Number: Lodged: Complete Specification Lodged: Accepted: Published: "*Priority: *..elated Art: 0 :Name of Applicant: RHONE-POULENC CHIMIE *so: Address of Applicant: 25, Quai Paul Doumer, 92408, Courbevoie, Cedex, France *-.Actual Inventor: Eric Garcin, Claude-Bernard Cartier and Eric Quemere S***A.ddress for Service: SHELSTON WATERS, 55 Clarence Street, Sydney Complete Specification for the Invention entitled: "ADSORBENT FOR PURIFYING OLEFINS" The following statement is a full description of this invention, including the best method of performing it known to us:- 1 ADSORBENT FOR PURIFYING OLEFINS The invention pertains to an adsorbent for purifying olefins. It pertains more particularly to an adsorbent, based on alumina, for the purification of polyolefins obtained by polymerisation of olefins in the presence of a system of coordination catalysts, and more precisely the reaction medium obtained through this polymerisation process.
Olefin polymerisation is usually performed in the presence of polymerisation catalysts including elements from groups IV B, V B, VI B of the element periodic classification and more particularly vanadium, titanium and zirconium. These catalysts also include organometallic (metallic alkyl), metallic hydride or metal hydroxide compounds as reducing agents. These catalysts are usually called transition catalysts and they exhibit a high catalytic activity for the polymerisation of olefins.
However, the olefins obtained are polluted by metallic residues originating from these catalysts and it is therefore necessary to purify them prior to their use, to avoid their tinting or degradation and to decrease their toxicity.
In addition, olefin polymerisation processes usually include a unit for the recovery of the solvents or monomers contained in the polyolefins, these solvents and monomers being recycled in the polymerisation unit. The presence of metals within these compounds generates problems with respect to corrosion of the plant.
To purify these olefins, the use of various adsorbents, for instance alumina in particular, is known.
5 Among the adsorbent used, it is an advantage to use adsorbents in the form of beads which can be more easily handled than powder or lumps of various shapes. Indeed, a product in the form of beads can be conveyed by the loading as well as by the unloading of purifying columns through pneumatic systems, for example.
Among the adsorbents, alumina can easily be shaped into beads. However this alumina, while interesting for its handling facility and for its good metal adsorption properties, presents a major disadvantage in that it favors isomerization of the solvents, such as for example butene contained within the polyolefins. Consequently, the solvents recovered cannot be entirely recycled and must often be subjected to further purification to eliminate the isomerized products.
The invention especially aims at circumventing these disadvantages by proposing an alumina based adsorbent with a weak isomerizing power and capable of being easily shaped into beads, for example, and more generally into a shape permitting easy handling.
To this end, the invention proposes an alumina based adsorbent for the purification of olefins, this alumina including at least one compound of an element selected from the group of the alkali or alkaline-earths, in an amount included between 15 mmole and 100 mmole of element per 100 g of alumina.
Unless otherwise specified, the concentrations are expressed in millimoles of element per 100 g of alumina calcinated at 3000C for 3 hours.
This adsorbent exhibits a weak olefin isomerizing power.
This isomerizing power of an adsorbent is determined by the following test: The Isomerizing power of these products is determined by conducting a test of isomerization of butene -1 into cis and trans butene -2.
To do so, 500 mg of ground adsorbent (of particles included between 400 and 500 pm) are introduced into a reactor. The product is conditioned for 2 hours at 250°C in a sweep of helium with a delivery rate of 2,5 I/h.
The product is then raised to 4000C and 1 ml of butene is injected into the helium flux.
Analysis of the gas released at the outlet by chromatography permits the 15 measurement of the quantity of butene cis and trans butene -2 recovered.
S* The theoretical thermodynamic equilibrium constant Kth(T) is determined by calculation and the actual equilibrium constant K(T) by the results from the measurements.
0see [cis butene -2]e [trans butene -2]e KthCr) [butene -1 1 e [cis butene -2]e [trans butene -2] e [cis butene [trans butene -2] K(T) :25 [butene [cis butene [trans butene -2] T is the temperature of the butene released at the outlet of the reactor, the other values representing the concentrations at the outlet of the reactor or at equilibrium e for temperature T.
The isomerizing power or isomerizing rate A(T) is given by the following equation
K(T)
A(T) x 100 Kth(TCr) According to a characteristic of the invention, the compound of the element is an oxide, hydroxide or salt of the latter. Of course, a mixture of these compounds can be used without departing from the framework of the invention.
Among the compounds, in addition to the hydroxides, may be mentioned by way of example the sulphates, nitrates, halogenides, acetates, formiates, carbonates and more generally the salts of carboxylic acids, for instance.
The preferred compounds of the invention are the hydroxides and the chlorides. The latter present a considerable economic advantage while providing a remarkably low isomerizing rate.
It is also possible to use a mixture of elements however, the total content of these elements will preferably have to be included between 15 mmole and 100 mmois per 100 g of alumina.
Among the suitable elements, sodium, potassium and calcium may be mentioned as preferred elements.
However, when potassium is selected, its content is preferably included be'Lween mmole and 80 mmole.
As suitable alumina for the invention, one may mention alumina exhibiting a specific *.15 surface area that is sufficient to obtain an acceptable adsorption rate of the metals. Typically, these alumina have a specific surface area that is greater than 50 m 2 /g.
These alumina are obtained through conventional processes such as the process by precipitation or gel, and the process by rapid dehydration of an hydroxide of alumina.
The latter alumina are preferred by the invention.
The incorporation of the element(s) to the alumina may be performed by any process, such as coprecipitation of the element with the alumina or impregnation, prior to or following shaping of the alumina, with a solution of the compound(s) of the element(s).
According to a preferred characteristic of the invention, the adsorbent manufacturing process consists of impregnating some alumina, preferably in the shape of beads, with an aqueous solution of a salt or hydroxide of the element to incorporate, then of drying the alumina and eventually, of subjecting it to thermal treatment to stabilise its specific surface *area.
This thermal treatment is conducted at a temperature determined in function either of the temperature of use of the adsorbent or of the desired specific surface area.
It is also possible to proceed to a thermal treatment at a higher temperature to achieve a degradation, at least partial, of the compound, for example in the form of oxide.
However, this degradation is not mandatory and by way of example is not necessary especially when using compounds such as chlorides, nitrates, hydroxides for instance.
The adsorbent of the invention is particularly used for the purification of polyolefins obtained by polymerisation of olefins in the presence of coordination catalysts, by adsorption of the metals originating from these catalysts. Thus, the olefins still contained in (he reaction mixture are purified without undergoing isomerization, and can therefore be entirely recycled This process also permits the purification of polyolefins.
4 The invention will be illustrated by the examples given below, solely by way of indication.
The adsorbents indicated below are manufactured by treatment of an alumina agglomerated into beads of a diameter of 1,5 mm 2,5 mm, with a specific surface area, measured by the B.E.T. method, of 295 m 2 a total porous volume of 0,5 cm 3 /g and whose sodium residual content is included between 0,2 and 0,4 (by weight).
These alumina beads are commercialised by RHONE-POULENC Company under the brand name "A 1,5 These alumina beads are then reactivated for 3 hours at 300°C in air, then impregnated with a solution of a salt of the element(s) or a compound, such as an hydroxide, of this element. The volume and the concentration of this solution are determined so as to ***achieve the desired elem'ent concentration in the alumina.
0 *The impregnated products are then dried for 12 hours at 110°C in air.
Their isomerizing powers are determined by means of the test described above.
1. 5 The various results and characteristics of the adsorbents are summarised in the Table below: *0 *0 0 i l• 0 Ex Element Impregnating X concentration Isomerizing X solution in the adsorbent power mmole /100 g Al20 3
A%
1(1) 0 63% 2 Na NaOH 25 14% 3 Na NaOH 62 4(1) Na NaOH 250 54% K KOH 26 8% 6 K KOH 68 14% 7 K KOH 15 16% 8(2) Ca Ca(COOCH 3 2 44 13% 9(2) Ca Ca(OOCCH 3 2 18 21% 10(2) Na NaOOCCH 3 36 9% 11(2) Na CH 3 COONa 90 9% 12 Na NaCI 65 1% 13(1) Na NaOH 12 42% 14(1) K KOH 130 77% *eg 15(2) Li CH 3 COOLi 45 14% 16(2) Sr Sr(OOCCH 3 2 65 36% 17(2) Mg Mg(OOCH 3 2 65 36% 18 Ca CaCl 45 11% comparative examples c--!inated at 600OC for 3 hours following impregnation The results clearly show that an alumina including an element such as sodium, potassium, calcium has a markedly lower isomerizing power than that of an untreated alumina (example Furthermore, these examples also show that reduction of the isomerizing power S of the alumina is obtained for a defined concentration range.
Thus, untreated alumina which contain sodium as impurity are not suitable since the sodium concentration is too low.
The same applies to alumina containing a high sodium content (5 and above) that are in particular used for the adsorption of acid impurities.
Alumina containing an element such as lithium, strontium and magnesium also exhibit a markedly lower isomerizing power than that of an untreated alumina (example 1).

Claims (7)

1. A method for adsorptive purification of a polyolefin obtained by olefin polymerisation in the presence of a metallic co-ordination catalyst, to remove catalyst metal residues therefrom, comprising the step of using an alumina based adsorbent including at least one compound of an element selected from the group including the alkali and alkaline-earths, the said element being present in an amount included between 15 mmole and 100 mmole per 100 g of alumina.
2. A method according to Claim 1, characterised in that the compound of the element is an oxide, hydroxide or salts of the said element.
3. A method according to Claim 1 or 2, characterised in that the compound of the element is a sulphate, nitrate, halogenide, acetate, formiate, carbonate or carboxylic acid salt of the said element. S4. A method according to one of claims 1 to 3, characterised in that the compound of the element is a chloride or an hydroxide. A method according to one of Claims 1 to 4, characterised in that the element is selected from the group including sodium, potassium, calcium.
6. A method according to Claim 5, characterised in that potassium is present in an amount included between 15 and 80 mmole per 100 g of alumina.
7. A method according to one of the previous claims, characterised in that the alumina has a specific surface area greater than 50 m 2/g.
8. A method according to one of the previous claims, characterised in that it is in the form of beads.
9. A method according to one of the previous claims, characterised in that the alumina is obtained by rapid dehydration of an hydroxide of alumina. 7 A method according to Claim 1 substantially as herein described with reference to the examples. DATED this 4th day of January, 1993 RHONE-POULENC CHIMIE Attorney: IAN T. ERNST Fellow Institute of Patent Attorneys of Australia of SHELSTON WATERS CoC *o *go *o
AU47973/90A 1989-01-18 1990-01-15 Adsorbent for purifying olefins Ceased AU634740B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8900530 1989-01-18
FR8900530A FR2641711B1 (en) 1989-01-18 1989-01-18 ADSORBENT FOR THE PURIFICATION OF POLYOLEFINS AND METHOD OF MANUFACTURE THEREOF

Publications (2)

Publication Number Publication Date
AU4797390A AU4797390A (en) 1990-07-26
AU634740B2 true AU634740B2 (en) 1993-03-04

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AU47973/90A Ceased AU634740B2 (en) 1989-01-18 1990-01-15 Adsorbent for purifying olefins

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EP (1) EP0379394B1 (en)
JP (1) JPH0628725B2 (en)
KR (1) KR960000497B1 (en)
CN (1) CN1017685B (en)
AR (1) AR244574A1 (en)
AT (1) ATE104172T1 (en)
AU (1) AU634740B2 (en)
BG (1) BG60545B1 (en)
BR (1) BR9000167A (en)
CA (1) CA2007937C (en)
DE (1) DE69007989T2 (en)
DK (1) DK0379394T3 (en)
ES (1) ES2055348T3 (en)
FR (1) FR2641711B1 (en)
MX (1) MX172197B (en)
TW (1) TW203016B (en)

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EP0580736B1 (en) * 1991-04-08 1997-04-09 Exxon Chemical Patents Inc. Process for upgrading the quality of light ends
US5302771A (en) * 1991-04-08 1994-04-12 Exxon Chemical Patents, Inc. Process for upgrading the quality of light ends
CA2149724A1 (en) * 1994-05-19 1995-11-20 Yoshinao Ito Method for purification of .alpha. olefins for polymerization use and methd for production of poly-.alpha.-olefins
FR2732622B1 (en) * 1995-04-10 1997-05-09 Rhone Poulenc Chimie PROCESS FOR THE ADSORPTION OF CHELATED ORGANOMETALLIC COMPOUNDS AND ALUMINUM BALLS COMPRISING AN ORGANOMETALLIC CHELATE COMPOUND
FR2736281B1 (en) * 1995-07-07 1997-08-01 Rhone Poulenc Chimie PROCESS FOR THE ADSORPTION OF CHELATED ORGANOMETALLIC COMPOUNDS AND ALUMINUM ADSORBENTS COMPRISING A CHELATED ORGANOMETALLIC COMPOUND
US5656064A (en) * 1995-10-04 1997-08-12 Air Products And Chemicals, Inc. Base treated alumina in pressure swing adsorption
FR2758554B1 (en) * 1997-01-22 1999-04-16 Rhodia Chimie Sa PROCESS FOR THE ELIMINATION OF INHIBITORS OF POLYMERIZATION OF MIXTURES OF MONOMERS USING AN ALUMIN OF OPTIMIZED FORM
US5846295A (en) * 1997-03-07 1998-12-08 Air Products And Chemicals, Inc. Temperature swing adsorption
FR2771944B1 (en) * 1997-12-08 2000-01-14 Air Liquide AIR PURIFICATION PROCESS BY ADSORPTION ON CALCINATED ALUMINUM OF CO2 AND H2O IMPURITIES
JP4557194B2 (en) * 1999-10-29 2010-10-06 Ｊｘ日鉱日石エネルギー株式会社 Process for dehalogenation of hydrocarbons containing carbon-carbon double bonds
KR100426957B1 (en) * 2001-12-31 2004-04-14 한국에너지기술연구원 Adsorbent Preparations and Applications for C4 Olefin Separation from Mixtures
EP2041190B1 (en) * 2006-07-19 2012-10-24 ExxonMobil Chemical Patents Inc. Process to produce polyolefins using metallocene catalysts
JP5185323B2 (en) * 2010-05-28 2013-04-17 Ｊｘ日鉱日石エネルギー株式会社 Method for regenerating alumina used for dehalogenation of hydrocarbons containing carbon-carbon double bonds
CN102775529B (en) * 2011-05-11 2015-04-29 中国石油化工股份有限公司 Method for removing impurities from olefin polymers
IN2013MU02038A (en) * 2013-06-17 2015-06-05 Reliance Ind Ltd
EP3112406A1 (en) * 2015-06-30 2017-01-04 The Procter and Gamble Company Method for purifying contaminated polyolefins
US9695259B2 (en) 2015-06-30 2017-07-04 The Procter & Gamble Company Method for purifying contaminated polymers
CN114989331B (en) * 2022-04-20 2024-02-02 万华化学集团股份有限公司 Polyolefin solution chelating deashing method

Citations (3)

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Publication number Priority date Publication date Assignee Title
US4433981A (en) * 1981-02-18 1984-02-28 Shell Oil Company CO2 Removal from gaseous streams
US4493715A (en) * 1982-12-20 1985-01-15 Phillips Petroleum Company Removal of carbon dioxide from olefin containing streams
US4571445A (en) * 1984-12-24 1986-02-18 Shell Oil Company Process for removal of sulfur compounds from conjugated diolefins

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1208141A (en) * 1982-12-20 1986-07-22 John P. Hogan Removal of carbon dioxide from olefin containing streams

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4433981A (en) * 1981-02-18 1984-02-28 Shell Oil Company CO2 Removal from gaseous streams
US4493715A (en) * 1982-12-20 1985-01-15 Phillips Petroleum Company Removal of carbon dioxide from olefin containing streams
US4571445A (en) * 1984-12-24 1986-02-18 Shell Oil Company Process for removal of sulfur compounds from conjugated diolefins

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CA2007937C (en) 1998-11-03
AR244574A1 (en) 1993-11-30
ES2055348T3 (en) 1994-08-16
EP0379394A1 (en) 1990-07-25
KR900011506A (en) 1990-08-01
BR9000167A (en) 1990-10-23
JPH02233137A (en) 1990-09-14
CN1017685B (en) 1992-08-05
JPH0628725B2 (en) 1994-04-20
KR960000497B1 (en) 1996-01-08
AU4797390A (en) 1990-07-26
BG90933A (en) 1993-12-24
ATE104172T1 (en) 1994-04-15
FR2641711B1 (en) 1993-10-22
BG60545B1 (en) 1995-08-28
FR2641711A1 (en) 1990-07-20
DE69007989T2 (en) 1994-08-18
TW203016B (en) 1993-04-01
DE69007989D1 (en) 1994-05-19
EP0379394B1 (en) 1994-04-13
CN1044415A (en) 1990-08-08
DK0379394T3 (en) 1994-05-16
MX172197B (en) 1993-12-06
CA2007937A1 (en) 1990-07-18

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