CN112778348A - Synthesis method of alkyl aluminum halide - Google Patents
Synthesis method of alkyl aluminum halide Download PDFInfo
- Publication number
- CN112778348A CN112778348A CN202110155415.6A CN202110155415A CN112778348A CN 112778348 A CN112778348 A CN 112778348A CN 202110155415 A CN202110155415 A CN 202110155415A CN 112778348 A CN112778348 A CN 112778348A
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- CN
- China
- Prior art keywords
- halide
- aluminum
- synthesis
- aluminum halide
- room temperature
- Prior art date
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- -1 alkyl aluminum halide Chemical class 0.000 title claims abstract description 48
- 238000001308 synthesis method Methods 0.000 title abstract description 5
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 238000002360 preparation method Methods 0.000 claims abstract description 19
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000004820 halides Chemical class 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 9
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 9
- 238000003786 synthesis reaction Methods 0.000 claims 9
- 239000000047 product Substances 0.000 abstract description 9
- 239000006227 byproduct Substances 0.000 abstract description 3
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 238000004448 titration Methods 0.000 description 12
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
- 238000003918 potentiometric titration Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229920005549 butyl rubber Polymers 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/064—Aluminium compounds with C-aluminium linkage compounds with an Al-Halogen linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention discloses a synthesis method of alkyl aluminum halide, which relates to the technical field of new material preparation, wherein the alkyl aluminum halide is dialkyl aluminum halide or monoalkyl aluminum dihalide; the reaction equation for dialkylaluminum halides is as follows:
the reaction equation for monoalkylaluminum dihalides is as follows:
the invention has the beneficial effects that: the invention adjusts AlX3And AlR3The preparation method is simple, no by-product is generated in the reaction, high temperature and high pressure are not needed, the reaction energy consumption of the system is reduced, the product purity is high, the dialkyl aluminum halide or the monoalkyl aluminum dihalide can be synthesized, and the industrialization of the product is easy to realize.
Description
Technical Field
The invention relates to the technical field of new material preparation, in particular to a synthetic method of alkyl aluminum halide.
Background
The silicon rubber is used as a sealant, a bonding agent and an insulating protective coating, is indispensably applied to key parts and core parts in various fields in China, and plays an irreplaceable role in civil and military production. The alkyl aluminum halides play an irreplaceable role as polymerization catalysts for butyl rubber and ethyl propyl rubber. An improved process for the preparation of butyl rubber using activated alkylaluminum halides is disclosed in patent publication No. CN 1253141A.
In the prior art, alkyl aluminum halide is prepared by introducing alkyl halohydrocarbon into Al powder at high temperature and high pressure to obtain a mixture of dialkyl aluminum halide and alkyl aluminum halide. The reaction can only obtain the mixture of dialkyl aluminum halide and alkyl aluminum dihalide, the product purification difficulty is high, the reaction needs high temperature and high pressure, and the reaction danger coefficient is high. It is also disclosed in the prior art that alkylaluminum halides are prepared by reacting a zinc halide with a trialkylaluminum, as disclosed in U.S. patent publication No. US3124604A, wherein the reaction equation is as follows: ZnCl2+2R3Al→R2Zn+2R2AlCl, the method can also obtain the mixture of dialkyl aluminum halide and dialkyl zinc with high yield, the separation difficulty of the two products is high by the rectification method, and if the method is used for obtaining the dialkyl halide with high yield, the method is not simple and economical.
Disclosure of Invention
The invention aims to solve the technical problems that in the prior art, the synthesis method of the alkyl aluminum halide needs high temperature and high pressure, and the preparation method is complex, and provides the synthesis method of the alkyl aluminum halide.
The invention solves the technical problems through the following technical means:
a method for synthesizing alkyl aluminum halide, wherein the alkyl aluminum halide is dialkyl aluminum halide or monoalkyl aluminum dihalide;
the reaction equation for the dialkylaluminum halide is as follows:
AlX3+2AlR3→3AlR2X；
the reaction equation for the monoalkylaluminum dihalide is as follows:
2AlX3+AlR3→3AlRX2；
wherein R is alkyl.
Has the advantages that: the invention adjusts AlX3And AlR3To obtain dialkyl aluminum halide or monoalkyl aluminum dihalide, the preparation method of the invention is simple, and the reaction is carried outNo by-product is generated, high temperature and high pressure are not needed, the reaction energy consumption of the system is reduced, the product purity is high, dialkyl aluminum halide or monoalkyl aluminum dihalide can be synthesized, and the industrialization of the product is easy to realize.
Preferably, said R ═ CH3、CH2CH3、CH2CH(CH3)2、C(CH3)3。
Preferably, X ═ Cl, Br, I.
Preferably, the method for preparing dialkyl aluminum halide comprises the following steps: to AlR3Adding AlX3The temperature is controlled to be 25-35 ℃, and the AlX is3With AlR3The molar ratio of the dialkyl aluminum halide to the dialkyl aluminum halide is 1: 2, and the reaction product is prepared after stirring.
Preferably, the reaction product is distilled under reduced pressure to obtain a colorless transparent liquid.
Preferably, the preparation method of the dialkyl aluminum halide specifically comprises the following steps: adding 0.5mol of trimethylaluminum, a thermometer and a stirrer into a 1L four-mouth round-bottom reaction bottle, adding 0.25mol of aluminum trichloride into the solid at the room temperature of 25 ℃, controlling the temperature to be between 25 and 35 ℃, stopping adding in batches half an hour, recovering the room temperature, stirring for 12 hours, and distilling under reduced pressure to obtain colorless transparent liquid.
Preferably, the preparation method of the dialkyl aluminum halide specifically comprises the following steps: adding 0.5mol of trimethylaluminum, a thermometer and a stirrer into a 1L four-mouth round bottom reaction bottle, adding 0.25mol of aluminum tribromide into the solid at the room temperature of 25 ℃, controlling the temperature to be between 25 and 35 ℃, stopping adding in batches in half an hour, recovering the room temperature, stirring for 12 hours, and distilling under reduced pressure to obtain colorless transparent liquid.
Preferably, the preparation process of the monoalkylaluminum dihalide comprises the following steps: to AlR3Adding AlX3The temperature is controlled to be 25-35 ℃, and the AlX is3With AlR3In a molar ratio of 2:1, and stirring to obtain a reaction product, namely monoalkylaluminum dihalide.
Preferably, the reaction product is distilled under reduced pressure to obtain a colorless transparent liquid.
Preferably, the preparation method of the monoalkylaluminum dihalide specifically comprises the following steps: adding 0.25mol of trimethylaluminum, a thermometer and a stirrer into a 1L four-mouth round-bottom reaction bottle, adding 0.5mol of aluminum trichloride into the solid at the room temperature of 25 ℃, controlling the temperature to be between 25 and 35 ℃, stopping adding in batches half an hour, recovering the room temperature, stirring for 12 hours, and distilling under reduced pressure to obtain colorless transparent liquid.
The invention has the advantages that: the invention adjusts AlX3And AlR3The preparation method is simple, no by-product is generated in the reaction, high temperature and high pressure are not needed, the reaction energy consumption of the system is reduced, the product purity is high, the dialkyl aluminum halide or the monoalkyl aluminum dihalide can be synthesized, and the industrialization of the product is easy to realize.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Test materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
The specific techniques or conditions not specified in the examples can be performed according to the techniques or conditions described in the literature in the field or according to the product specification.
Example 1
A process for the preparation of a dialkylaluminum halide comprising the steps of:
adding 36.04g of trimethylaluminum (0.5mol), a thermometer and a stirrer into a 1L four-mouth round-bottom reaction bottle, adding 33.34g of aluminum trichloride (0.25mol) into a solid at the room temperature of 25 ℃, controlling the temperature to be between 25 and 35 ℃, ending batch addition for half an hour, recovering the room temperature, stirring for 12 hours, and removing reaction residues through reduced pressure distillation to obtain 90.28g of colorless transparent liquid with the yield of 97.6%;
and (3) titration of Al content: al 29.15%, Cl content titration: and Cl is 38.30%. The method comprises the following steps of performing a test on the aluminum content and the halogen content by adopting EDTA titration and potentiometric titration, wherein the EDTA titration and the potentiometric titration are both in the prior art.
Example 2
A process for the preparation of a dialkylaluminum halide comprising the steps of:
adding 36.04g of trimethylaluminum (0.5mol), a thermometer and a stirrer into a 1L four-mouth round-bottom reaction bottle, adding 66.67g of aluminum tribromide (0.25mol) into a solid at the room temperature of 25 ℃, controlling the temperature to be between 25 and 35 ℃, ending batch addition for half an hour, recovering the room temperature, stirring for 12 hours, and removing reaction residues through reduced pressure distillation to obtain 95g of colorless transparent liquid, wherein the yield is 92.5%;
and (3) titration of Al content: al 19.71%, Cl content titration: and Cl is 58.31%. The method comprises the following steps of performing a test on the aluminum content and the halogen content by adopting EDTA titration and potentiometric titration, wherein the EDTA titration and the potentiometric titration are both in the prior art.
Example 3
A process for the preparation of a monoalkylaluminum dihalide comprising the steps of:
adding 18.02g of trimethylaluminum (0.25mol), a thermometer and a stirrer into a 1L four-mouth round-bottom reaction bottle, adding 66.67g of aluminum trichloride (0.5mol) into a solid at the room temperature of 25 ℃, controlling the temperature to be between 25 and 35 ℃, ending batch addition for half an hour, recovering the room temperature, stirring for 12 hours, and removing reaction residues through reduced pressure distillation to obtain 82g of colorless transparent liquid, wherein the yield is 96.8%;
and (3) titration of Al content: al 23.89%, Cl content titration: and Cl is 62.8%. The method comprises the following steps of performing a test on the aluminum content and the halogen content by adopting EDTA titration and potentiometric titration, wherein the EDTA titration and the potentiometric titration are both in the prior art.
The above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.
Claims (10)
1. A method for synthesizing alkyl aluminum halide is characterized in that: the alkyl aluminum halide is dialkyl aluminum halide or monoalkyl aluminum dihalide;
the reaction equation for the dialkylaluminum halide is as follows:
AlX3+2AlR3→3AlR2X；
the reaction equation for the monoalkylaluminum dihalide is as follows:
2AlX3+AlR3→3AlRX2；
wherein R is alkyl.
2. The process for the synthesis of an alkylaluminum halide according to claim 1, wherein: r is CH3、CH2CH3、CH2CH(CH3)2、C(CH3)3。
3. The process for the synthesis of an alkylaluminum halide according to claim 1, wherein: and X is Cl, Br and I.
4. The process for the synthesis of an alkylaluminum halide according to claim 1, wherein: the preparation method of the dialkyl aluminum halide comprises the following steps: to AlR3Adding AlX3The temperature is controlled to be 25-35 ℃, and the AlX is3With AlR3The molar ratio of the dialkyl aluminum halide to the dialkyl aluminum halide is 1: 2, and the reaction product is prepared after stirring.
5. The process for the synthesis of an alkylaluminum halide according to claim 4, wherein: the reaction product was distilled under reduced pressure to obtain a colorless transparent liquid.
6. The process for the synthesis of an alkylaluminum halide according to claim 4, wherein: the preparation method of the dialkyl aluminum halide specifically comprises the following steps: adding 0.5mol of trimethylaluminum, a thermometer and a stirrer into a 1L four-mouth round-bottom reaction bottle, adding 0.25mol of aluminum trichloride into the solid at the room temperature of 25 ℃, controlling the temperature to be between 25 and 35 ℃, stopping adding in batches half an hour, recovering the room temperature, stirring for 12 hours, and distilling under reduced pressure to obtain colorless transparent liquid.
7. The process for the synthesis of an alkylaluminum halide according to claim 4, wherein: the preparation method of the dialkyl aluminum halide specifically comprises the following steps: adding 0.5mol of trimethylaluminum, a thermometer and a stirrer into a 1L four-mouth round bottom reaction bottle, adding 0.25mol of aluminum tribromide into the solid at the room temperature of 25 ℃, controlling the temperature to be between 25 and 35 ℃, stopping adding in batches in half an hour, recovering the room temperature, stirring for 12 hours, and distilling under reduced pressure to obtain colorless transparent liquid.
8. The process for the synthesis of an alkylaluminum halide according to claim 1, wherein: the preparation method of the monoalkyl aluminum dihalide comprises the following steps: to AlR3Adding AlX3The temperature is controlled to be 25-35 ℃, and the AlX is3With AlR3In a molar ratio of 2:1, and stirring to obtain a reaction product, namely monoalkylaluminum dihalide.
9. The process for the synthesis of an alkylaluminum halide according to claim 8, wherein: the reaction product was distilled under reduced pressure to obtain a colorless transparent liquid.
10. The process for the synthesis of an alkylaluminum halide according to claim 8, wherein: the preparation method of the monoalkyl aluminum dihalide specifically comprises the following steps: adding 0.25mol of trimethylaluminum, a thermometer and a stirrer into a 1L four-mouth round-bottom reaction bottle, adding 0.5mol of aluminum trichloride into the solid at the room temperature of 25 ℃, controlling the temperature to be between 25 and 35 ℃, stopping adding in batches half an hour, recovering the room temperature, stirring for 12 hours, and distilling under reduced pressure to obtain colorless transparent liquid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110155415.6A CN112778348A (en) | 2021-02-04 | 2021-02-04 | Synthesis method of alkyl aluminum halide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110155415.6A CN112778348A (en) | 2021-02-04 | 2021-02-04 | Synthesis method of alkyl aluminum halide |
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| CN112778348A true CN112778348A (en) | 2021-05-11 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202110155415.6A Withdrawn CN112778348A (en) | 2021-02-04 | 2021-02-04 | Synthesis method of alkyl aluminum halide |
Country Status (1)
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024081453A1 (en) * | 2022-10-14 | 2024-04-18 | Praxair Technology, Inc. | High performance semiconductor grade dimethylaluminum chloride |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB798599A (en) * | 1956-04-10 | 1958-07-23 | Petrochemicals Ltd | Improvements in or relating to the manufacture of aluminium dialkyl monohalides |
| DE1178432B (en) * | 1962-02-21 | 1964-09-24 | Montedison Spa | Process for the preparation of alkyl aluminum halides |
| US4118409A (en) * | 1974-03-27 | 1978-10-03 | Texas Alkyls, Inc. | Process for the simultaneous production of trimethylaluminum and alkylaluminum halides |
| CN1746173A (en) * | 2004-09-02 | 2006-03-15 | 罗门哈斯电子材料有限公司 | Method |
| US20110021800A1 (en) * | 2008-11-12 | 2011-01-27 | Nippon Aluminum Alkyls, Ltd. | Method for manufacturing dialkylaluminum monohalide |
-
2021
- 2021-02-04 CN CN202110155415.6A patent/CN112778348A/en not_active Withdrawn
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB798599A (en) * | 1956-04-10 | 1958-07-23 | Petrochemicals Ltd | Improvements in or relating to the manufacture of aluminium dialkyl monohalides |
| DE1178432B (en) * | 1962-02-21 | 1964-09-24 | Montedison Spa | Process for the preparation of alkyl aluminum halides |
| AT238221B (en) * | 1962-02-21 | 1965-01-25 | Montedison Spa | Process for the preparation of alkyl aluminum halides |
| US4118409A (en) * | 1974-03-27 | 1978-10-03 | Texas Alkyls, Inc. | Process for the simultaneous production of trimethylaluminum and alkylaluminum halides |
| CN1746173A (en) * | 2004-09-02 | 2006-03-15 | 罗门哈斯电子材料有限公司 | Method |
| US20110021800A1 (en) * | 2008-11-12 | 2011-01-27 | Nippon Aluminum Alkyls, Ltd. | Method for manufacturing dialkylaluminum monohalide |
Non-Patent Citations (1)
| Title |
|---|
| 袁履冰等: "《有机铝化合物》", 30 September 1980 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024081453A1 (en) * | 2022-10-14 | 2024-04-18 | Praxair Technology, Inc. | High performance semiconductor grade dimethylaluminum chloride |
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