CA2637118A1 - Method of preparing organometallic compounds - Google Patents

Method of preparing organometallic compounds Download PDF

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Publication number
CA2637118A1
CA2637118A1 CA002637118A CA2637118A CA2637118A1 CA 2637118 A1 CA2637118 A1 CA 2637118A1 CA 002637118 A CA002637118 A CA 002637118A CA 2637118 A CA2637118 A CA 2637118A CA 2637118 A1 CA2637118 A1 CA 2637118A1
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CA
Canada
Prior art keywords
compound
microchannel device
impurities
alkylating agent
purifying
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
Application number
CA002637118A
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French (fr)
Other versions
CA2637118C (en
Inventor
Francis Joseph Lipiecki
Stephen Gerald Maroldo
Deodatta Vinayak Shenai-Khatkhate
Robert Adams Ware
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Rohm and Haas Co
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Rohm and Haas Co
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Publication of CA2637118A1 publication Critical patent/CA2637118A1/en
Application granted granted Critical
Publication of CA2637118C publication Critical patent/CA2637118C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/30—Germanium compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/14—Fractional distillation or use of a fractionation or rectification column
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/06—Aluminium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/06—Aluminium compounds
    • C07F5/061—Aluminium compounds with C-aluminium linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/06—Aluminium compounds
    • C07F5/061—Aluminium compounds with C-aluminium linkage
    • C07F5/062—Al linked exclusively to C
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/06—Aluminium compounds
    • C07F5/069—Aluminium compounds without C-aluminium linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/28—Titanium compounds
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/06—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of metallic material
    • C23C16/18—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of metallic material from metallo-organic compounds
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/44—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the method of coating
    • C23C16/4401—Means for minimising impurities, e.g. dust, moisture or residual gas, in the reaction chamber
    • C23C16/4402—Reduction of impurities in the source gas
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y80/00—Products made by additive manufacturing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Abstract

A method of preparing an ultra-pure organometallic compound comprising using a microchannel device for synthesis in reacting a metal halide with an alkylating agent to produce an ultra-pure alkylmetal compound for processes such as chemical vapor deposition.

Claims (12)

1. A process for preparing organometallic compounds of ultra-high purity comprising:
reacting a metal salt and an alkylating agent in a microchannel device to yield an organometallic compound wherein the resulting compound has the minimum purity required for chemical vapor deposition processes.
2. The process of claim 1 wherein the purity of the compound ranges from is at least 99.99% pure.
3. The process of claim 1 wherein the metal salt is a metal halide.
4. The process of claim 1 further wherein the reaction is performed in the presence of a solvent.
5. The process of claim 1 further comprising purifying the alkylating agent.
6. The process of claim 5 wherein the alkylating agent is further purified using a microchannel device.
7. The process of claim 1 wherein the alkylating agent comprises a trialkylaluminum compound, an alkyl magnesium halide compound, or an alkyllithium compound and wherein the molar ratio of alkyalting agent to metal halide is greater than or equal to one.
8. The process of claim 7 wherein the alkylating agent is a trialkylaluminum compound and the trialkylaluminum is in the presence of a tertiary amine, a tertiary phosphine, or a mixture of a tertiary amine and a tertiary phosphine in a microchannel device.
9. A method of preparing an organometallic compound of ultra-high purity comprising purifying an organometallic compound comprising impurities in a microchannel device to reduce the level of impurities with relative volativity (.alpha.) between 0.8 < .alpha. < 1.5 to a level useful in electronic materials applications.
10. The method of claim 9 comprising purifying an organometallic compound comprising impurities in a microchannel device to reduce the level of impurities with relative volatility (.alpha.) between 0.8 < .alpha. <
1.5.to less than 1 ppm.
11. The method of claim 9 comprising purifying an organometallic compound comprising impurities in a microchannel device using temperature swing adsorption to reduce the level of impurities via adduct formation.
12. The method of claim 9 wherein the microchannel device further comprises a height equivalent theoretical plate (HETP) of less than 5 cm.
CA2637118A 2007-07-20 2008-07-09 Method of preparing organometallic compounds Expired - Fee Related CA2637118C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US96137007P 2007-07-20 2007-07-20
US60/961,370 2007-07-20

Publications (2)

Publication Number Publication Date
CA2637118A1 true CA2637118A1 (en) 2009-01-20
CA2637118C CA2637118C (en) 2012-08-14

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA2637118A Expired - Fee Related CA2637118C (en) 2007-07-20 2008-07-09 Method of preparing organometallic compounds

Country Status (7)

Country Link
US (4) US7659414B2 (en)
EP (4) EP2020258A2 (en)
JP (1) JP2009035539A (en)
KR (2) KR20090009733A (en)
CN (2) CN101347685A (en)
CA (1) CA2637118C (en)
TW (1) TW200914123A (en)

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US7659414B2 (en) * 2007-07-20 2010-02-09 Rohm And Haas Company Method of preparing organometallic compounds
US8101048B2 (en) * 2007-07-20 2012-01-24 Rohm And Haas Company Purification process using microchannel devices
WO2009017962A2 (en) * 2007-08-02 2009-02-05 Linde, Inc. Low-volatility compounds for use in forming deposited layers
SG178736A1 (en) * 2007-10-31 2012-03-29 Advanced Tech Materials Amorphous ge/te deposition process
JP2011162542A (en) * 2010-02-05 2011-08-25 Rohm & Haas Co Method of preparing organometallic compound
JP2011168576A (en) * 2010-02-05 2011-09-01 Rohm & Haas Co Method of preparing organometallic compound
FR2968677A1 (en) * 2010-12-09 2012-06-15 Commissariat Energie Atomique PROCESS FOR PRODUCING LITHIUM-BASED CVD LAYERS
EP2545973B1 (en) 2011-07-13 2020-03-04 Dow Global Technologies LLC Organometallic compound purification by stripping step
EP2545972A1 (en) 2011-07-13 2013-01-16 Dow Global Technologies LLC Organometallic compound purification by two steps distillation
EP2559682B1 (en) * 2011-08-15 2016-08-03 Rohm and Haas Electronic Materials LLC Organometallic compound preparation
EP2559681B1 (en) * 2011-08-15 2016-06-22 Dow Global Technologies LLC Organometallic compound preparation
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Also Published As

Publication number Publication date
US20110172452A1 (en) 2011-07-14
EP2359923A1 (en) 2011-08-24
US20100185003A1 (en) 2010-07-22
KR20090009733A (en) 2009-01-23
KR20100114864A (en) 2010-10-26
EP2020258A2 (en) 2009-02-04
CA2637118C (en) 2012-08-14
US7659414B2 (en) 2010-02-09
US7919638B2 (en) 2011-04-05
TW200914123A (en) 2009-04-01
US20100185002A1 (en) 2010-07-22
CN101348499A (en) 2009-01-21
US8101787B2 (en) 2012-01-24
EP2359922A1 (en) 2011-08-24
CN101347685A (en) 2009-01-21
US7939684B2 (en) 2011-05-10
US20090023940A1 (en) 2009-01-22
JP2009035539A (en) 2009-02-19
EP2439208A1 (en) 2012-04-11

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