WO2002070527A1 - Mass-selective purification of organometallics - Google Patents

Mass-selective purification of organometallics Download PDF

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Publication number
WO2002070527A1
WO2002070527A1 PCT/US2002/006538 US0206538W WO02070527A1 WO 2002070527 A1 WO2002070527 A1 WO 2002070527A1 US 0206538 W US0206538 W US 0206538W WO 02070527 A1 WO02070527 A1 WO 02070527A1
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organometallic compound
alkyl group
composition
organometallic
impurities
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PCT/US2002/006538
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French (fr)
Inventor
Greogry M. Smith
Barry J. Cottrell
Eric J. Majoor
Daniel Smith
Paul A. Iacobucci
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Akzo Nobel N.V.
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Publication of WO2002070527A1 publication Critical patent/WO2002070527A1/en

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    • 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
    • C07F7/22—Tin compounds
    • C07F7/2296—Purification, stabilisation, isolation
    • 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
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
    • C07F3/06—Zinc 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
    • C07F5/061—Aluminium compounds with C-aluminium linkage
    • C07F5/062—Al linked exclusively to C

Definitions

  • the present invention relates to a process for purifying an organometallic compound. More particularly, it relates to a process for removing trace amounts of non- equal-mass components contained in an organometallic compound-containing composition that is useful as a raw material for fabricating so-called compound semi- conductors .
  • a compound semiconductor two or more elements are combined to form a semiconductor.
  • Non- limiting examples of compound semiconductor materials include phases referred to in the relevant art as GaAs , AlGaAs, AlGaln ⁇ s, InP, InGaP, AlInGaP, GaN, InGaN, CdSe, ZnSe, AlSb, and the like.
  • Organometallic compounds are used as raw materials in processes which form a thin film of a compound semiconductor by a process variously referred to in the art as chemical vapor deposition (CVD) , metalorganic chemical vapor deposition and the like.
  • CVD chemical vapor deposition
  • Such a thin film is utilized in, among other things, light-emitting diodes, laser diodes, microwave elements, ultraspeed integrated circuit (IC) components and opto-electronic IC components.
  • IC ultraspeed integrated circuit
  • Japanese Patent Publication No. 03112991 distillation to remove trimethylaluminum from aluminum trichloride .
  • U.S. Patent No. 6,140,522 to CA. Mol et al . (assigned to Urenco Nederland B.V.) describes a method for altering the ratio of isotopes of the metal of a metal alkyl in that the amount of depleted or enriched metal alkyl , in preferably liquid form, is contacted with an amount of the metal of the metal alkyl or an alloy of the metal of the metal alkyl and is held in contact for some time.
  • the performance of the semiconductor devices can be improved by changing the distribution of isotopic atoms present in the semiconductor.
  • Some patents that relate to this technique include U.S. Patent Nos . 5,442,191, 6,156,601 and 5,144,409.
  • the isotope distribution can be controlled by subjecting the organometallic precursor to an isotope separation technique that enriches the organometallic in species comprising a particular isotope or set of isotopes.
  • the isotopic enrichment is based on a mass-selective partitioning process that is applied to the semiconductor precursor organometallic.
  • mass- selective partitioning processes include those that rely upon mass-derived physical properties such as differential rates of gas diffusion, or high-speed gas centrifugation. Because mass-selective processes, in addition to segregating molecular species on the basis of differences in isotopic composition, will also separate otherwise similar molecular species on the basis of differing molecular weights arising from small differences in atomic constitution, these mass-selective partitioning process can also be used to partition desirable organometallic species from undesirable impurities with different molecular weights.
  • a process that separates 28 SiMe 4 from 29 SiMe on the basis of differing molecular masses will also separate SiMe 4 species from impurity species such as AlMe 3 or MeOSiMe 3 .
  • the present invention comprises the application of such mass-selective segregation processes, heretofore applied to problems in isotope enrichment, to the problem of removing trace-level impurities from volatile organometallic compounds that are useful for the fabrication of compound semiconductors.
  • the present invention is a process for the separation of impurities from an organometallic compound-containing composition that comprises treating the composition containing the organometallic compound and impurities .
  • the impurities to be removed are of differing molecular formulae from the formula of the organometallic compound.
  • the composition that is treated, in accordance with the present invention is in the vapor phase, and the treatment to separate the impurities from the organometallic compound takes place in a gas ultracentrifuge to cause a separation of that composition into fractions of differing mass with the removal of any fraction preferentially containing such an impurity from any fraction containing the organometallic compound to thereby further purify the organometallic compound.
  • the present invention comprises a process wherein a volatile organometallic compound is subjected to a mass-selective segregation process in which heavier and lighter fractions are separated from one another and those heavier and lighter fractions are set aside in order to recover a chemically purified fraction of the desired median molecular weight species.
  • a mass-selective segregation process in which heavier and lighter fractions are separated from one another and those heavier and lighter fractions are set aside in order to recover a chemically purified fraction of the desired median molecular weight species.
  • gas centrifugation used in separating isotopes of uranium, we too are interested in the lower weight species.
  • the desire is to minimize contamination of the desired organometallic product with silicon and oxygen- containing species .
  • alkyls will also be present in the heavier weight fraction and thus leave the desired product at a higher level of purity.
  • An isotope enrichment strategy such as one to segregate a compound into light and heavy fractions , does not in and of itself accomplish a chemical purification. This is because these strategies would typically concentrate on maximizing the recovery of a light or a heavy fraction, or both. In this case, light chemical impurities would be carried along in the light fraction and heavy impurities would be carried into the heavy fraction.
  • the median weight fraction which may well not be isotopically enriched, is retained will provide a good recovery of a chemically purified material of that type .
  • an insufficiently purified sample of a volatile organometallic compound is subjected to a mass- differentiation process (such as those based differential diffusion rates in a gas-phase centrifuge process) to yield a heavy ("H") and a light (“L”) fraction.
  • a mass- differentiation process such as those based differential diffusion rates in a gas-phase centrifuge process
  • H heavy
  • L light
  • HH heavy-heavy
  • HL heavy-light
  • LH light-heavy
  • LL light-light
  • HH refers to the heavier fraction obtained from subjecting the heavier fraction of a previously divided fraction to a mass-selective differentiation process
  • HL refers to the lighter fraction of a previously divided fraction to a mass- selective differentiation process
  • Processes such as this can be cascaded, with, for instance, the consolidated HL and LH fractions of one two- stage process passed again through the process to further deplete impurities .
  • the LL and HH fractions can also be further processed to recover purer fractions that can also be passed through the process again.
  • Cascading and combining such processes to obtain an efficient multi-stage process is simply an exercise in design and separation modeling, a technique well developed for multi-pass separation processes, such as isotope enrichment, multi-stage extraction, crystallization, membrane diffusion, and the like.
  • one aspect of this invention is the purification process itself. Additional aspects of this invention are the purified products of this process , as well as semiconductor fabrication processes employing the purified products, and the resulting semiconductor phases and devices .
  • the process of the present invention in a preferred embodiment utilizes a gas or ultracentrifuge, which operates under the standard conditions of such a piece of equipment, to achieve the desired purification (separation of impurities from a desired organometallic compound) .
  • a separation means is used since more conventional means of separation cannot be used due to the similarities, for example, of the boiling points of the constituents to be separated.
  • this technology was developed originally to separate isotopes of particular compounds from each other using the principle of their inherent weight differences by spinning the mixture at a very high rate of speed.
  • Such equipment can be typically operated in the range of from about 30,000 to about 70,000 revolutions per minute (rpm) in order to achieve the desired separation.
  • Gas separation units are typically used in series and operated in a cascade mode .
  • the separation factor of the gas centrifuge depends on the difference between the molecular weights of the two constituents and not on the square root of the ratio of the molecular weights, as is the case in a diffusion processes. This factor is much more favorable for isotopic mixtures of the heavier elements than for those of the lighter elements .
  • the typical rotor has an accurately machined outside diameter of about 150 mm with a wall thickness of 8 mm and a length of 700 mm. It is typically fabricated of an aluminum alloy (BONDUR alloy) that has a high elastic limit and high tensile strength.
  • the shaft is hollow so that gas can be fed and removed through it.
  • the motor delivers 2.1 kw at 60,000 rpm, and all bearings are lubricated by a forced circulation system.
  • a gas centrifuge may also be operated with the temperature at its top and bottom being maintained at different levels by means of suitable heating or cooling devices. When this is done, the separation obtained is also dependent on this temperature gradient as well, which causes convective circulation inside of the centrifuge .
  • vacuum tubes of from about one to about two meters in length and from about 15 to about 20 cm in diameter can be used. Gas circulates axially within the cylinder with the heavier molecules collecting against the wall of the cylinder and the lighter constituents passing into the next separator for further purification.
  • a cascade mode of separation is typically employed since enrichment per stage is not too significant.
  • Feed rates to the parallel bank of separators is typically lower than in the case of gas diffusion, but the enrichment is substantially more significant. Maintenance of a thermal gradient in the separator is also important to insure good mixing. However, the gradient is not so significant as to affect the integrity of the molecules being separated. An appropriate measure of the purity for a composition of interest will be expressed in microgram of the undesirable element (s) per gram of desired metal constituent.
  • An example of a stream to be separated could be defined as follows: 99.992% (wt% ) aluminum, such as contained in trimethyl aluminum ("TMAL), and 0.005% (wt%) , or 50 ppm, oxygen contained within the organometallic species containing oxygen, and 0.003% (wt%) , or 30 ppm, silicon contained within the silicon-containing species .
  • TMAL trimethyl aluminum
  • the desired result is the improvement in purity of the TMAL with reduction of the noted contaminants.
  • other high molecular weight species other contaminants can also be removed.
  • Alkyl and aromatic solvents present at even low levels are anticipated to end up with the higher molecular weight fraction due to their molecular weight relative to that of the desired product.
  • the stream is expected to be concentrated by three to five times in the desired aluminum-containing species.
  • the undesired species would be expected to be decreased by three to five times their initial concentration. It would be anticipated that a five-fold decrease in oxygen- and silicon-containing species would yield a purified stream of the following composition: 99.998% (wt%) aluminum, as contained in TMAL; about 10 ppm oxygen contained within oxygen containing- organometallic species in the composition; and about 6 ppm silicon contained within the silicon-containing species that are in the composition.
  • organometallic compounds which are preferably the lower alkyl (e.g., Ci to C 4 alkyl group-containing) organometallic compounds containing a metal atom from any of Groups 12 (e.g. , zinc) , 13 (e.g., aluminum, gallium, or indium), 14 (e.g., germanium or tin) or 16 (e.g., selenium or tellurium) of the Periodic Table of the Elements, as described in Chemical and Engineering News 63(5) , 27 (1985) .
  • organometallic compounds which are preferably the lower alkyl (e.g., Ci to C 4 alkyl group-containing) organometallic compounds containing a metal atom from any of Groups 12 (e.g. , zinc) , 13 (e.g., aluminum, gallium, or indium), 14 (e.g., germanium or tin) or 16 (e.g., selenium or tellurium) of the Periodic Table of the Elements, as described
  • TMI trimethyl indium
  • TMG trimethyl gallium
  • DMZ triethyl aluminum
  • TAG triethyl gallium
  • DEZ diethyl zinc
  • DMSe dimethyl selenide
  • DIPSe diisopropylselenide
  • DMT dimethyltelluride
  • TMSn tetramethyltin

Abstract

Impurities can be separated from an organometallic compound by treating the composition containing the impurity-containing organometallic compound, when it is in the vapor phase, in a gas ultracentrifuge to cause a separation of the composition into fractions of differing mass with the separation of any fraction preferentially containing an impurity from any fraction containing the organometallic compound.

Description

Mass-Selective Purification of Organometallics
The present invention relates to a process for purifying an organometallic compound. More particularly, it relates to a process for removing trace amounts of non- equal-mass components contained in an organometallic compound-containing composition that is useful as a raw material for fabricating so-called compound semi- conductors . In a compound semiconductor two or more elements are combined to form a semiconductor. Non- limiting examples of compound semiconductor materials include phases referred to in the relevant art as GaAs , AlGaAs, AlGalnΛs, InP, InGaP, AlInGaP, GaN, InGaN, CdSe, ZnSe, AlSb, and the like.
Organometallic compounds are used as raw materials in processes which form a thin film of a compound semiconductor by a process variously referred to in the art as chemical vapor deposition (CVD) , metalorganic chemical vapor deposition and the like. Such a thin film is utilized in, among other things, light-emitting diodes, laser diodes, microwave elements, ultraspeed integrated circuit (IC) components and opto-electronic IC components. However, it is well known that the performance of these devices can be profoundly affected by low levels of impurities that may be present in the precursor organometallic compound.
A number of patents describe a variety of approaches that have been used to remove impurities from organometallic compounds, including the following, which appear to relate to the use of physical processes as opposed to the use of chemical additives to achieve purification: U.S. Patent No. 5,951,820 (use of sublimation) ; Japanese Patent Publication No. 08012678 (use of fractional melt crystallization) ; Japanese Patent Publication No. 06247977 (use of sublimation) ; Japanese Patent Publication No. 06145177 (use of heating and purging for solvent removal) ; Japanese Patent Publication No. 06009651 (isotropic distillation to remove ether) ; and
Japanese Patent Publication No. 03112991 (distillation to remove trimethylaluminum from aluminum trichloride .
U.S. Patent No. 6,140,522 to CA. Mol et al . (assigned to Urenco Nederland B.V.) describes a method for altering the ratio of isotopes of the metal of a metal alkyl in that the amount of depleted or enriched metal alkyl , in preferably liquid form, is contacted with an amount of the metal of the metal alkyl or an alloy of the metal of the metal alkyl and is held in contact for some time. This reference, while indicating the use of a ultracentrifugation technique to treat a dethylzinc (DEZ) feedstock to separate the various isotopic forms of zinc from one another, it does not address the removal of trace amounts of non-equal-mass components, of differing molecular formulae from that of a desired organometallic compound, that may be contained in an organometallic compound-containing composition.
It is also known that, in at least some cases, the performance of the semiconductor devices can be improved by changing the distribution of isotopic atoms present in the semiconductor. Some patents that relate to this technique include U.S. Patent Nos . 5,442,191, 6,156,601 and 5,144,409. Generally speaking, the isotope distribution can be controlled by subjecting the organometallic precursor to an isotope separation technique that enriches the organometallic in species comprising a particular isotope or set of isotopes. Generally speaking, the isotopic enrichment is based on a mass-selective partitioning process that is applied to the semiconductor precursor organometallic. Such technology has been known since the Manhattan Project and is well known for use in, for example, isotopic enrichment of uranium for nuclear reactor fuel applications . These mass- selective partitioning processes include those that rely upon mass-derived physical properties such as differential rates of gas diffusion, or high-speed gas centrifugation. Because mass-selective processes, in addition to segregating molecular species on the basis of differences in isotopic composition, will also separate otherwise similar molecular species on the basis of differing molecular weights arising from small differences in atomic constitution, these mass-selective partitioning process can also be used to partition desirable organometallic species from undesirable impurities with different molecular weights. For instance, a process that separates 28SiMe4 from 29SiMe on the basis of differing molecular masses (caused by the differing atomic weight of 29Si and 28Si) will also separate SiMe4 species from impurity species such as AlMe3 or MeOSiMe3. The present invention comprises the application of such mass-selective segregation processes, heretofore applied to problems in isotope enrichment, to the problem of removing trace-level impurities from volatile organometallic compounds that are useful for the fabrication of compound semiconductors.
The present invention is a process for the separation of impurities from an organometallic compound-containing composition that comprises treating the composition containing the organometallic compound and impurities . The impurities to be removed are of differing molecular formulae from the formula of the organometallic compound. The composition that is treated, in accordance with the present invention, is in the vapor phase, and the treatment to separate the impurities from the organometallic compound takes place in a gas ultracentrifuge to cause a separation of that composition into fractions of differing mass with the removal of any fraction preferentially containing such an impurity from any fraction containing the organometallic compound to thereby further purify the organometallic compound.
In particular, the present invention comprises a process wherein a volatile organometallic compound is subjected to a mass-selective segregation process in which heavier and lighter fractions are separated from one another and those heavier and lighter fractions are set aside in order to recover a chemically purified fraction of the desired median molecular weight species. Preferably, in this invention we are more interested in removing and concentrating species of a desired molecular weight. As in the case of gas centrifugation used in separating isotopes of uranium, we too are interested in the lower weight species. The desire is to minimize contamination of the desired organometallic product with silicon and oxygen- containing species . Other alkyls will also be present in the heavier weight fraction and thus leave the desired product at a higher level of purity. An isotope enrichment strategy, such as one to segregate a compound into light and heavy fractions , does not in and of itself accomplish a chemical purification. This is because these strategies would typically concentrate on maximizing the recovery of a light or a heavy fraction, or both. In this case, light chemical impurities would be carried along in the light fraction and heavy impurities would be carried into the heavy fraction. However, by designing a process wherein the lighter and heavier fractions are systematically culled out, and the median weight fraction, which may well not be isotopically enriched, is retained will provide a good recovery of a chemically purified material of that type . For example, in one embodiment of the present invention, an insufficiently purified sample of a volatile organometallic compound is subjected to a mass- differentiation process (such as those based differential diffusion rates in a gas-phase centrifuge process) to yield a heavy ("H") and a light ("L") fraction. After each of these fractions is again subjected to the process, the result will be a heavy-heavy ("HH") , a heavy-light ("HL") , a light-heavy ("LH") and a light-light ("LL") fraction. In this nomenclature, "HH" refers to the heavier fraction obtained from subjecting the heavier fraction of a previously divided fraction to a mass-selective differentiation process , "HL" refers to the lighter fraction of a previously divided fraction to a mass- selective differentiation process, and so forth. In the two-stage process just described, lighter impurities (such as Me3Al in Me3Ga or Me4Si in Me3In) will concentrate in the LL fraction while heavy impurities (such as Me4Si in Me3Al) will concentrate in the HH fraction, leaving both the HL and the LH fractions depleted of impurities . These can then' be combined to obtain a more chemically purified product .
Processes such as this can be cascaded, with, for instance, the consolidated HL and LH fractions of one two- stage process passed again through the process to further deplete impurities .
The LL and HH fractions can also be further processed to recover purer fractions that can also be passed through the process again. Cascading and combining such processes to obtain an efficient multi-stage process is simply an exercise in design and separation modeling, a technique well developed for multi-pass separation processes, such as isotope enrichment, multi-stage extraction, crystallization, membrane diffusion, and the like.
Thus , one aspect of this invention is the purification process itself. Additional aspects of this invention are the purified products of this process , as well as semiconductor fabrication processes employing the purified products, and the resulting semiconductor phases and devices .
The process of the present invention in a preferred embodiment utilizes a gas or ultracentrifuge, which operates under the standard conditions of such a piece of equipment, to achieve the desired purification (separation of impurities from a desired organometallic compound) . Such a separation means is used since more conventional means of separation cannot be used due to the similarities, for example, of the boiling points of the constituents to be separated. As mentioned previously, this technology was developed originally to separate isotopes of particular compounds from each other using the principle of their inherent weight differences by spinning the mixture at a very high rate of speed. Such equipment can be typically operated in the range of from about 30,000 to about 70,000 revolutions per minute (rpm) in order to achieve the desired separation. Gas separation units are typically used in series and operated in a cascade mode .
The theory behind the separation is as follows (as described in Perry' s Chemical Engineer' s Handbook) . When a vertical cylinder containing a gas mixture is rotated about its axis at high angular velocity, the contained mixture will tend to separate, with the higher molecular weight component concentrating near the walls of the cylinder and the lower molecular weight component concentrating toward the axis . If the lighter stream is made to flow upwardly near the axial region of the cylinder, and the heavier stream is made to flow downwardly near the wall of the cylinder, a longitudinal composition can be established. The longer the cylinder, the greater is the difference in gas composition, other conditions being constant.
The separation factor of the gas centrifuge depends on the difference between the molecular weights of the two constituents and not on the square root of the ratio of the molecular weights, as is the case in a diffusion processes. This factor is much more favorable for isotopic mixtures of the heavier elements than for those of the lighter elements .
The typical rotor has an accurately machined outside diameter of about 150 mm with a wall thickness of 8 mm and a length of 700 mm. It is typically fabricated of an aluminum alloy (BONDUR alloy) that has a high elastic limit and high tensile strength. The shaft is hollow so that gas can be fed and removed through it. The motor delivers 2.1 kw at 60,000 rpm, and all bearings are lubricated by a forced circulation system. A gas centrifuge may also be operated with the temperature at its top and bottom being maintained at different levels by means of suitable heating or cooling devices. When this is done, the separation obtained is also dependent on this temperature gradient as well, which causes convective circulation inside of the centrifuge . It is important that the components to be separated are thermally stable in the vapor phase since the separation is run on the gaseous constituents of the composition. Typically, vacuum tubes of from about one to about two meters in length and from about 15 to about 20 cm in diameter can be used. Gas circulates axially within the cylinder with the heavier molecules collecting against the wall of the cylinder and the lighter constituents passing into the next separator for further purification. A cascade mode of separation is typically employed since enrichment per stage is not too significant.
Feed rates to the parallel bank of separators is typically lower than in the case of gas diffusion, but the enrichment is substantially more significant. Maintenance of a thermal gradient in the separator is also important to insure good mixing. However, the gradient is not so significant as to affect the integrity of the molecules being separated. An appropriate measure of the purity for a composition of interest will be expressed in microgram of the undesirable element (s) per gram of desired metal constituent.
An example of a stream to be separated could be defined as follows: 99.992% (wt% ) aluminum, such as contained in trimethyl aluminum ("TMAL), and 0.005% (wt%) , or 50 ppm, oxygen contained within the organometallic species containing oxygen, and 0.003% (wt%) , or 30 ppm, silicon contained within the silicon-containing species . The desired result is the improvement in purity of the TMAL with reduction of the noted contaminants. However, it is contemplated that other high molecular weight species (other contaminants) can also be removed.
Alkyl and aromatic solvents present at even low levels are anticipated to end up with the higher molecular weight fraction due to their molecular weight relative to that of the desired product. After the first pass, the stream is expected to be concentrated by three to five times in the desired aluminum-containing species. Thus, the undesired species would be expected to be decreased by three to five times their initial concentration. It would be anticipated that a five-fold decrease in oxygen- and silicon-containing species would yield a purified stream of the following composition: 99.998% (wt%) aluminum, as contained in TMAL; about 10 ppm oxygen contained within oxygen containing- organometallic species in the composition; and about 6 ppm silicon contained within the silicon-containing species that are in the composition.
Because of the larger difference in molecular weights of these species relative to the separation of isotopes the use of gas centrifugation could prove to be even more efficient than the three to fivefold improvement per pass mentioned above.
A similar process with similar process steps is contemplated for purification of other organometallic compounds (which are preferably the lower alkyl (e.g., Ci to C4 alkyl group-containing) organometallic compounds containing a metal atom from any of Groups 12 (e.g. , zinc) , 13 (e.g., aluminum, gallium, or indium), 14 (e.g., germanium or tin) or 16 (e.g., selenium or tellurium) of the Periodic Table of the Elements, as described in Chemical and Engineering News 63(5) , 27 (1985) . Representative organometallic compounds that may be purified by the process of this invention include such compounds as trimethyl indium (TMI) , trimethyl gallium (TMG) , dimethyl zinc (DMZ) , triethyl aluminum (TEAL) , triethyl gallium (TEG) , diethyl zinc (DEZ) , dimethyl selenide (DMSe) , diisopropylselenide (DIPSe) , dimethyltelluride (DMT) , tetramethyltin (TMSn) , and the like.

Claims

Claims :
1. A process for the separation of impurities from an organometallic compound-containing composition which comprises treating the composition containing the organometallic compound and impurities, which impurities are of differing molecular formulae from the formula of the organometallic compound, when the composition is in the vapor phase, in a gas ultracentrifuge to cause a separation of that composition into fractions of differing mass with the removal of any fraction preferentially containing an impurity from any fraction containing the organometallic compound to thereby further purify the organometallic compound.
2. A process as claimed in Claim 1 wherein the ultracenrifuge is operated in the range of from about 30,000 to about 70,000 revolutions per minute.
3. A process as claimed in Claim 1 wherein the organometallic compound is a lower alkyl group-containing organometallic compound.
4. A process as claimed in Claim 1 wherein the ultracenrifuge is operated in the range of from about
30,000 to about 70,000 revolutions per minute and wherein the organometallic compound is a lower alkyl group- containing organometallic compound.
5. A process as claimed in Claim 1 wherein the organometallic compound is a Ci to C4 alkyl group-containing organometallic compound.
6. A process as claimed in Claim 1 wherein the organometallic compound contains a metal atom selected from the group consisting of any of Groups 12, 13, 14, or 16 of the Periodic Table of the Elements . i
7. A process as claimed in Claim 1 wherein the organometallic compound contains a metal atom selected from the group consisting of zinc, aluminum, gallium, indium, germanium, tin, selenium and tellurium.
8. A process as claimed in Claim 1 wherein the ultracenrifuge is operated in the range of from about 30,000 to about 70,000 revolutions per minute, wherein the organometallic compound is a lower alkyl group-containing organometallic compound, and wherein the organometallic compound contains a metal atom selected from the group consisting of any of Groups 12, 13, 14, or 16 of the Periodic Table of the Elements .
9. A process as claimed in Claim 1 wherein the ultracenrifuge is operated in the range of from about 30,000 to about 70,000 revolutions per minute, wherein the organometallic compound is a Ci to C4 alkyl group-containing organometallic compound, and wherein the organometallic 5 compound contains a metal atom selected from the group consisting of any of Groups 12, 13, 14, or 16 of the Periodic Table of the Elements .
10. A process as claimed in Claim 1 wherein the ultracenrifuge is operated in the range of from about
30,000 to about 70,000 revolutions per minute, wherein the organometallic compound is a Ci to C4 alkyl group-containing organometallic compound, and wherein the organometallic compound contains a metal atom selected from the group consisting of zinc, aluminum, gallium, indium, germanium, tin, selenium and tellurium.
11. A process as claimed in Claim 1 wherein the organometallic compound is a lower alkyl group-containing organometallic compound containing aluminum.
12. A process as claimed in Claim 1 wherein the ultracenrifuge is operated in the range of from about
30,000 to about 70,000 revolutions per minute and wherein the organometallic compound is a lower alkyl group- containing organometallic compound containing aluminum.
13. A process as claimed in Claim 12 wherein the organometallic compound is trimethylaluminum.
PCT/US2002/006538 2001-03-02 2002-03-01 Mass-selective purification of organometallics WO2002070527A1 (en)

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US11059828B2 (en) 2009-10-23 2021-07-13 Janssen Pharmaceutica Nv Disubstituted octahydropyrrolo[3,4-C]pyrroles as orexin receptor modulators

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US11059828B2 (en) 2009-10-23 2021-07-13 Janssen Pharmaceutica Nv Disubstituted octahydropyrrolo[3,4-C]pyrroles as orexin receptor modulators
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US10828302B2 (en) 2016-03-10 2020-11-10 Janssen Pharmaceutica Nv Methods of treating depression using orexin-2 receptor antagonists
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