WO2007027437A1 - Processes for preparing mtt zeolites using nitrogen-containing organic compounds - Google Patents
Processes for preparing mtt zeolites using nitrogen-containing organic compounds Download PDFInfo
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- WO2007027437A1 WO2007027437A1 PCT/US2006/032008 US2006032008W WO2007027437A1 WO 2007027437 A1 WO2007027437 A1 WO 2007027437A1 US 2006032008 W US2006032008 W US 2006032008W WO 2007027437 A1 WO2007027437 A1 WO 2007027437A1
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- WIPO (PCT)
- Prior art keywords
- sda
- zeolite
- diamine
- propane
- cation
- Prior art date
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- BXYVQNNEFZOBOZ-UHFFFAOYSA-N CN(C)CCCNCCCN(C)C Chemical compound CN(C)CCCNCCCN(C)C BXYVQNNEFZOBOZ-UHFFFAOYSA-N 0.000 description 2
- KFDIDIIKNMZLRZ-UHFFFAOYSA-N CC(C)NCCCN Chemical compound CC(C)NCCCN KFDIDIIKNMZLRZ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B39/00—Compounds having molecular sieve and base-exchange properties, e.g. crystalline zeolites; Their preparation; After-treatment, e.g. ion-exchange or dealumination
- C01B39/02—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof; Direct preparation thereof; Preparation thereof starting from a reaction mixture containing a crystalline zeolite of another type, or from preformed reactants; After-treatment thereof
- C01B39/46—Other types characterised by their X-ray diffraction pattern and their defined composition
- C01B39/48—Other types characterised by their X-ray diffraction pattern and their defined composition using at least one organic template directing agent
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B39/00—Compounds having molecular sieve and base-exchange properties, e.g. crystalline zeolites; Their preparation; After-treatment, e.g. ion-exchange or dealumination
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B39/00—Compounds having molecular sieve and base-exchange properties, e.g. crystalline zeolites; Their preparation; After-treatment, e.g. ion-exchange or dealumination
- C01B39/02—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof; Direct preparation thereof; Preparation thereof starting from a reaction mixture containing a crystalline zeolite of another type, or from preformed reactants; After-treatment thereof
- C01B39/06—Preparation of isomorphous zeolites characterised by measures to replace the aluminium or silicon atoms in the lattice framework by atoms of other elements, i.e. by direct or secondary synthesis
- C01B39/12—Preparation of isomorphous zeolites characterised by measures to replace the aluminium or silicon atoms in the lattice framework by atoms of other elements, i.e. by direct or secondary synthesis the replacing atoms being at least boron atoms
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S423/00—Chemistry of inorganic compounds
- Y10S423/36—MTT, e.g. ZSM-23, ISI-1, KZ-1, EU-1, EU-4, EU-13
Definitions
- the present invention relates to a process for preparing zeolites having the MTT framework topology defined by the connectivity of the tetrahedral atoms in the zeolite using nitrogen-containing organic compounds.
- MTT MTT
- SSZ-32 SSZ-32 and methods for making it are disclosed in U.S. Patent No. 5,053,373, issued October 1, 1991 to Zones.
- This patent discloses the preparation of zeolite SSZ-32 using anN-lower alkyl-N'- isopropylimidazolium cation as an organic structure directing agent (SDA), sometimes called a templating agent.
- SDA organic structure directing agent
- U.S. Patent No. 4,076,842 issued February 28, 1978 to Plank et al., discloses the preparation of the zeolite designated "ZSM-23", a zeolite with a structure similar to SSZ-32, using a cation derived from pyrrolidine as the SDA.
- Zeolites SSZ-32 and ZSM-23 are commonly referred to as having the MTT .framework topology. Both of the aforementioned patents are incorporated herein by reference in their entirety.
- Other MTT zeolites include EU-13, ISI-4 and KZ-I.
- U. S. Patent No. 5,707,600 issued January 13, 1998 to Nakagawa et al., discloses a process for preparing medium pore size zeolites, including SSZ-32, using small, neutral amines.
- the amines contain (a) only carbon, nitrogen and hydrogen atoms, (b) one primary, secondary or tertiary, but not quaternary, amino group, and (c) a tertiary nitrogen atom, at least one tertiary carbon atom, or a nitrogen atom bonded directly to at least one secondary carbon atom, wherein the process is conducted in the absence of a quaternary ammonium compound.
- small amines examples include isobutylamine, diisobutylamine, trimethylamine, cyclopentylamine, diisopropylamine, sec-butylamine, 2,5-dimethylpyrrolidine and 2,6-dimethylpiperidine.
- U. S. Patent No. 5,707,601 issued January 13, 1998 to Nakagawa, discloses a process for preparing MTT zeolites using small, neutral amines.
- the amines contain (a) only carbon, nitrogen and hydrogen atoms, (b) one primary, secondary or tertiary, but not quaternary, amino group, and (c) a tertiary nitrogen atom, at least one tertiary carbon atom, or a nitrogen atom bonded directly to at least one secondary carbon atom, wherein the process is conducted in the absence of a quaternary ammonium compound.
- small amines examples include isobutylamine, diisobutylamine, trimethylamine, cyclopentylamine, diisopropylamine, sec-butylamine, 2,5- dimethylpyrrolidine and 2,6-dimethylpiperidine.
- zeolites including medium pore size, unidimensional zeolites, can be prepared using a mixture of an amine component comprising (1) at least one amine containing one to eight carbon atoms, ammonium hydroxide, and mixtures thereof, and (2) an organic templating compound capable of forming the zeolite in the presence of the amine component, wherein the amine is smaller than the organic templating compound.
- an amine component comprising (1) at least one amine containing one to eight carbon atoms, ammonium hydroxide, and mixtures thereof, and (2) an organic templating compound capable of forming the zeolite in the presence of the amine component, wherein the amine is smaller than the organic templating compound.
- amines examples include isopropylamine, isobutylamine, n-butylamine, piperidine, 4-methylpiperidine, cyclohexylamine, 1,1,3,3-tetramethylbutylamine and cyclopentylamine and mixtures of such amines.
- MTT zeolites such as SSZ-32, can be prepared using certain nitrogen-containing organic compounds.
- the present invention provides said process which is performed in the absence of any nitrogen-containing organic SDA other than the nitrogen-containing organic compounds of this invention.
- the present invention also provides MTT zeolites having a composition, as- synthesized and in the anhydrous state, in terms of mole ratios, is as follows:
- Y is silicon; W is aluminum, boron, gallium, indium, iron, titanium, vanadium or mixtures thereof; c is 1 or 2; d is 2 when c is 1 (i.e., W is tetravalent) or d is 3 or 5 when c is 2 (i.e., d is 3 when W is trivalent or 5 when W is pentavalent); Q is at least one nitrogen-containing organic compound selected from the group consisting of the following:
- M is an alkali metal cation, alkaline earth metal cation or mixtures thereof; and n is the valence of M (i.e., 1 or 2).
- the present invention also provides a preferred embodiment of this composition wherein said composition does not contain any nitrogen-containing organic templating agent other than the nitrogen-containing organic compounds of this invention.
- the present invention comprises:
- the process of the present invention comprises forming a reaction mixture from sources of alkali and/or alkaline earth metal (M) cations with valences n (i.e., 1 or 2); sources of an oxide of aluminum, boron, iron, gallium, indium, titanium, vanadium or mixtures thereof (W); sources of an oxide of silicon oxide (Y); at least one nitrogen-containing organic compound of this invention (Q); and water, said reaction mixture having a composition in terms of mole ratios within the following ranges:
- H 2 OAO 2 10 - 70 25 - 50 where Y is silicon; W is aluminum, boron, gallium, indium, iron, titanium, vanadium; a is 1 or 2, b is 2 when a is 1 (i.e., W is tetravalent); b is 3 when a is 2 (i.e., W is trivalent); M is an alkali metal cation, alkaline earth metal cation or mixtures thereof; n is the valence of M (i.e., 1 or 2); and Q is at least one nitrogen-containing organic compound of this invention.
- Embodiments of the process of this invention include reaction mixtures in which the YO 2 ZW 3 O b mole ratio is from about 20 to about 80; from about 20 to less than 40; 40 or more; and from 40 to about 80.
- Typical sources of aluminum oxide for the reaction mixture include aluminates, alumina, hydrated aluminum hydroxides, and aluminum compounds such as AlCl 3 and A1 2 (SO 4 )3.
- Typical sources of silicon oxide include silica hydrogel, silicic acid, colloidal silica, tetraalkyl orthosilicates, silica hydroxides, and fumed silicas. Other metals can be added in forms corresponding to their aluminum and silicon counterparts. Trivalent elements stabilized on silica colloids are also useful reagents.
- the SDA' s useful in the process of the present invention include the following nitrogen-containing organic compounds:
- the reactants and the nitrogen-containing organic compounds of this invention can be dissolved in water and the resulting reaction mixture maintained at an elevated temperature until crystals are formed.
- the temperatures during the hydrothermal crystallization step are typically maintained from about 100°C to about 250 0 C, preferably from about 140 0 C to about 200 0 C.
- the crystallization period is typically 6- 21 days, and generally about 7-14 days.
- the hydrothermal crystallization is usually conducted under pressure and usually in an autoclave so that the reaction mixture is subject to autogenous pressure.
- the reaction mixture should be stirred during crystallization.
- the solid product is separated from the reaction mixture by standard mechanical separation techniques, such as filtration.
- the crystals are water-washed and then dried, e.g., at 90 0 C to 150 0 C for from 8 to 24 hours, to obtain the as-synthesized zeolite crystals.
- the drying step can be performed at atmospheric or subatmospheric pressures.
- the crystals can be allowed to nucleate spontaneously from the reaction mixture.
- the reaction mixture can also be seeded with crystals of the desired zeolite both to direct, and accelerate the crystallization, as well as to minimize the formation of any undesired crystalline phases.
- seed crystals typically about 0.5% to about 5.0% (based on the weight of silica used in the reaction mixture) of the seed crystals of the desired zeolite are added.
- the as-synthesized MTT zeolite product made by the process of this invention has an as-synthesized composition comprising, in terms of mole ratios in the anhydrous state, the following:
- Y is silicon
- W is aluminum, boron, gallium, indium, iron, titanium, vanadium or mixtures thereof
- c is 1 or 2
- d is 2 when c is 1 or d is 3 or 5 when c is 2
- Q is at least one nitrogen-containing organic compound of this invention
- M is an alkali metal cation, alkaline earth metal cation or mixtures thereof
- n is the valence of M.
- Y is silicon
- W is aluminum
- M is potassium
- Q is SDA A, E or O (SDA A is relatively inexpensive to synthesize, SDA O is more expensive to make than SDA E, but is still relatively easy to synthesize and SDA E crystallizes MTT in a relatively short period of time).
- the YO 2 / W 0 O d ratio be from about 20 to about 80.
- the YO 2 / W c Oa ratio is from about 20 to less than 40, and in another embodiment this ratio is greater than 40, e.g., from 40 to about 80.
- the MTT zeolites can be made with a mole ratio of YO 2 /W c O d of ⁇ , i.e., there is essentially no W 0 O d present in the MTT zeolite.
- the zeolite would be an all-silica material.
- the MTT zeolite can be made essentially aluminum free, i.e., having a silica to alumina mole ratio of ⁇ .
- a method of increasing the mole ratio of silica to alumina is by using standard acid leaching or chelating treatments.
- essentially aluminum-free MTT zeolites can be synthesized using essentially aluminum-free silicon sources as the main tetrahedral metal oxide component.
- the MTT zeolites can also be prepared directly as an aluminosilicate.
- Lower silica to alumina ratios may also be obtained by using methods which insert aluminum into the crystalline framework. For example, aluminum insertion may occur by thermal treatment of the zeolite in combination with an alumina binder or dissolved source of alumina. Such procedures are described in U.S. Patent No. 4,559,315, issued on December 17, 1985 to Chang et al.
- the zeolite is thermally treated (calcined) prior to use as a catalyst.
- the zeolite can be leached with chelating agents, e.g., EDTA or dilute acid solutions, to increase the silica/alumina mole ratio.
- chelating agents e.g., EDTA or dilute acid solutions
- the zeolite can also be steamed; steaming helps stabilize the crystalline lattice to attack from acids.
- the zeolite can be used in intimate combination with hydrogenating components, such as tungsten, vanadium molybdenum, rhenium, nickel cobalt, chromium, manganese, or a noble metal, such as palladium or platinum, for those applications in which a hydrogenation- dehydrogenation function is desired.
- Typical replacing cations can include hydrogen and hydrogen precursors, rare earth metals, and metals from Groups HA, IDA, IVA, IB, HB, IIIB, IVB, VIB, and VIII of the Periodic Table of Elements.
- hydrogen and cations of metals such as rare earth, Mn 3 Ca, Mg, Zn, Cd, Pt, Pd, Ni, Co, Ti, Al, Sn, Ga, In and Fe are particularly preferred.
- the X-ray diffraction pattern of Table I is representative of a calcined MTT zeolite (in this case SSZ-32) made in accordance with this invention. Minor variations in the diffraction pattern can result from variations in the silica-to-alumina mole ratio of the particular sample due to changes in lattice constants. In addition, sufficiently small crystals will affect the shape and intensity of peaks, leading to significant peak broadening.
- the variation in the scattering angle (two theta) measurements, due to instrument error and to differences between individual samples, is estimated at +/- 0.20 degrees.
- the X-ray powder diffraction pattern was determined by standard techniques.
- the radiation was the K-alpha/doublet of copper.
- a diffractometer with a scintillation counter detector was used.
- the peak heights I and the positions, as a function of 2Theta where Theta is the Bragg angle, were read from the relative intensities, 100 x 1/I 0 where I 0 is the intensity of the strongest line or peak, and d, the interplanar spacing in Angstroms corresponding to the recorded lines, can be calculated.
- the X-ray patterns provided are based on a relative intensity scale in which the strongest line in the X-ray pattern is assigned a value of 100: W(weak) is less than 20; M(medium) is between 20 and 40; S(strong) is between 40 and 60; VS(very strong) is greater than 60.
- Table IA shows an X-ray diffraction pattern representative of a calcined MTT zeolite (SSZ-32) made in accordance with this invention.
- the ⁇ intensity (I) of the peaks or lines is expressed as the intensity relative to the strongest peak or line in the pattern, i.e., 1/I 0 x 100 where I 0 is the intensity of the strongest peak or line.
- Table HA shows the major peaks of a typical X-ray diffraction pattern for as-synthesized MTT zeolite made in accordance with this invention, including the relative intensities of the peaks or lines.
- Calcination can also result in changes in the intensities of the peaks as well as minor shifts in the diffraction pattern.
- the zeolite produced by exchanging the metal or other cations present in the zeolite with various other cations (such as H + or NH 4 + ) yields essentially the same diffraction pattern, although again, there may be minor i shifts in the interplanar spacing and variations in the relative intensities of the peaks. Notwithstanding these minor perturbations, the basic crystal lattice remains unchanged by these treatments.
- the MTT zeolites prepared by the process of this invention are useful in hydrocarbon conversion reactions.
- Hydrocarbon conversion reactions are chemical and catalytic processes in which carbon-containing compounds are changed to different carbon-containing compounds. Examples of hydrocarbon conversion reactions include catalytic cracking, hydrocracking, dewaxing, alkylation, isomerization, olefin and aromatics formation reactions, and aromatics isomerization and disproportionation.
- the autoclave was then placed in an oven with a rotating spit (43 rpm) and heated at 160 0 C for 17 days. After the reaction was completed, the reaction mixture was removed, cooled to room temperature, and then the reactor contents were filtered under vacuum in a glass filtration funnel. The solids were then washed with 500-1500 mL deionized water and dried overnight either at room temperature or in an oven at 90-150 0 C.
- borosilicate syntheses For borosilicate syntheses, a typical example is as follows (with SDA E): 1.Og IN KOH, 0.70g N-isopropyl-l,3-propanediamine, and 10.4 g deionized H 2 O were mixed together in a 23 mL Teflon cup. Next 0.035g potassium tetraborate tetrahydrate was dissolved in the mixture. Finally 0.90 g of Cabosil M-5 was added, and the resultant gel was thoroughly mixed to create a uniform gel. The Teflon reactor was then capped and sealed inside a Parr autoclave. The autoclave was placed in an oven with a rotating spit (43 rpm) and heated at 15O 0 C for 10 days.
- reaction mixture was removed, cooled to room temperature, and then the reactor contents were filtered under vacuum in a glass filtration funnel. The solids were then washed with 500-1500 mL deionized water and either dried overnight at room temperature or in an oven at 90-150 0 C.
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Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
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EP06801642.7A EP1928786B1 (en) | 2005-08-30 | 2006-08-15 | Processes for preparing mtt zeolites using nitrogen-containing organic compounds |
AU2006285146A AU2006285146B2 (en) | 2005-08-30 | 2006-08-15 | Processes for preparing MTT zeolites using nitrogen-containing organic compounds |
KR1020087007471A KR101285526B1 (en) | 2005-08-30 | 2006-08-15 | Processes for preparing mtt zeolites using nitrogen-containing organic compounds using nitrogen-containing organic compounds |
CN2006800366971A CN101277902B (en) | 2005-08-30 | 2006-08-15 | Processes for preparing MTT zeolites using nitrogen-containing organic compounds |
ES06801642.7T ES2623864T3 (en) | 2005-08-30 | 2006-08-15 | Processes for the preparation of MTT zeolites using organic compounds containing nitrogen |
JP2008529095A JP5258568B2 (en) | 2005-08-30 | 2006-08-15 | Method for preparing MTT zeolite using nitrogen-containing organic compound |
CA 2620145 CA2620145C (en) | 2005-08-30 | 2006-08-15 | Processes for preparing mtt zeolites using nitrogen-containing organic compounds |
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US11/216,546 | 2005-08-30 | ||
US11/216,546 US7157075B1 (en) | 2005-08-30 | 2005-08-30 | Process for preparing MTT zeolites using nitrogen-containing organic compounds |
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US (3) | US7157075B1 (en) |
EP (1) | EP1928786B1 (en) |
JP (1) | JP5258568B2 (en) |
KR (1) | KR101285526B1 (en) |
CN (1) | CN101277902B (en) |
AU (1) | AU2006285146B2 (en) |
CA (1) | CA2620145C (en) |
ES (1) | ES2623864T3 (en) |
WO (1) | WO2007027437A1 (en) |
ZA (1) | ZA200802680B (en) |
Cited By (1)
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JP2020514224A (en) * | 2017-01-11 | 2020-05-21 | シェブロン ユー.エス.エー. インコーポレイテッド | Synthesis of zeolite SSZ-31 |
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US7157075B1 (en) * | 2005-08-30 | 2007-01-02 | Chevron U.S.A. Inc. | Process for preparing MTT zeolites using nitrogen-containing organic compounds |
US8500991B2 (en) * | 2008-12-16 | 2013-08-06 | Exxonmobil Research And Engineering Company | High activity MTT framework type molecular sieves |
KR101147008B1 (en) * | 2009-06-22 | 2012-05-22 | 한국과학기술원 | Regularly stacked multilamellar and randomly arranged unilamellar zeolite nanosheets, and their analogue materials whose framework thickness were corresponding to one unit cell size or less than 10 unit cell size |
US8142757B2 (en) * | 2009-11-05 | 2012-03-27 | Chevron U.S.A. Inc. | Method for making borosilicate ZSM-48 molecular sieves |
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ES2860749T3 (en) | 2014-05-21 | 2021-10-05 | Chevron Usa Inc | Molecular sieve SSZ-95 |
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US9193600B1 (en) * | 2014-06-04 | 2015-11-24 | Chevron U. S. A. Inc. | Method for making molecular sieve SSZ-99 |
US9192924B1 (en) * | 2014-06-04 | 2015-11-24 | Chevron U.S.A. Inc. | Molecular sieve SSZ-99 |
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WO2017003907A1 (en) | 2015-06-30 | 2017-01-05 | Uop Llc | Uzm-53, an mtt zeolite |
US9694353B2 (en) * | 2015-10-07 | 2017-07-04 | Chevron U.S.A. Inc. | Molecular sieve SSZ-90, its synthesis and use |
US10160657B2 (en) * | 2016-11-17 | 2018-12-25 | Chevron U.S.A. Inc. | High-silica SSZ-32x zeolite |
CN111032572B (en) * | 2018-02-20 | 2023-01-24 | 雪佛龙美国公司 | Molecular sieve SSZ-113, its synthesis and application |
CN112218826B (en) * | 2018-06-07 | 2023-05-26 | 雪佛龙美国公司 | Synthesis of molecular sieve SSZ-109 |
US20240059573A1 (en) | 2021-01-07 | 2024-02-22 | China Petroleum & Chemical Corporation | Zsm-23 zeolite and preparation process and use thereof |
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2005
- 2005-08-30 US US11/216,546 patent/US7157075B1/en active Active
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2006
- 2006-08-15 WO PCT/US2006/032008 patent/WO2007027437A1/en active Application Filing
- 2006-08-15 ES ES06801642.7T patent/ES2623864T3/en active Active
- 2006-08-15 CA CA 2620145 patent/CA2620145C/en active Active
- 2006-08-15 KR KR1020087007471A patent/KR101285526B1/en active IP Right Grant
- 2006-08-15 ZA ZA200802680A patent/ZA200802680B/en unknown
- 2006-08-15 CN CN2006800366971A patent/CN101277902B/en active Active
- 2006-08-15 AU AU2006285146A patent/AU2006285146B2/en active Active
- 2006-08-15 EP EP06801642.7A patent/EP1928786B1/en active Active
- 2006-08-15 JP JP2008529095A patent/JP5258568B2/en active Active
- 2006-12-01 US US11/565,812 patent/US7682600B2/en not_active Expired - Fee Related
- 2006-12-18 US US11/612,275 patent/US20070128106A1/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2190910A (en) * | 1986-05-22 | 1987-12-02 | British Petroleum Co Plc | Synthesis of ZSM-23 |
EP0347273A1 (en) * | 1988-06-15 | 1989-12-20 | Institut Français du Pétrole | Process for the synthesis of MTT structure-type zeolites |
US5707601A (en) * | 1995-03-17 | 1998-01-13 | Chevron U.S.A. Inc. | Process for preparing zeolites having MTT crystal structure using small, neutral amines |
US6475464B1 (en) * | 1999-09-29 | 2002-11-05 | Institut Francais Du Petrole | Process for preparing a zeolite with structure type MTT using zeolitic material seeds |
Non-Patent Citations (1)
Title |
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See also references of EP1928786A4 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2020514224A (en) * | 2017-01-11 | 2020-05-21 | シェブロン ユー.エス.エー. インコーポレイテッド | Synthesis of zeolite SSZ-31 |
Also Published As
Publication number | Publication date |
---|---|
US20070128105A1 (en) | 2007-06-07 |
KR101285526B1 (en) | 2013-07-17 |
US7682600B2 (en) | 2010-03-23 |
ZA200802680B (en) | 2009-09-30 |
ES2623864T3 (en) | 2017-07-12 |
AU2006285146B2 (en) | 2011-04-21 |
CA2620145A1 (en) | 2007-03-08 |
CN101277902A (en) | 2008-10-01 |
CN101277902B (en) | 2012-03-28 |
EP1928786B1 (en) | 2016-12-28 |
AU2006285146A1 (en) | 2007-03-08 |
KR20080040787A (en) | 2008-05-08 |
JP5258568B2 (en) | 2013-08-07 |
US7157075B1 (en) | 2007-01-02 |
JP2009505940A (en) | 2009-02-12 |
EP1928786A4 (en) | 2015-06-03 |
US20070128106A1 (en) | 2007-06-07 |
EP1928786A1 (en) | 2008-06-11 |
CA2620145C (en) | 2013-05-21 |
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