CN105622662A - Method for preparing dialkoxydiphenylsilane through direct method - Google Patents
Method for preparing dialkoxydiphenylsilane through direct method Download PDFInfo
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- CN105622662A CN105622662A CN201610147710.6A CN201610147710A CN105622662A CN 105622662 A CN105622662 A CN 105622662A CN 201610147710 A CN201610147710 A CN 201610147710A CN 105622662 A CN105622662 A CN 105622662A
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- prepares
- sodium metal
- dialkoxy silicane
- direct method
- reaction
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Links
- 238000000034 method Methods 0.000 title claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000002245 particle Substances 0.000 claims abstract description 15
- 239000000725 suspension Substances 0.000 claims abstract description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011259 mixed solution Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 34
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 22
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 17
- 235000010290 biphenyl Nutrition 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000006185 dispersion Substances 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- 235000021314 Palmitic acid Nutrition 0.000 claims description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- 229940098695 palmitic acid Drugs 0.000 claims description 3
- 239000012188 paraffin wax Substances 0.000 claims description 3
- 229910052754 neon Inorganic materials 0.000 claims description 2
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 12
- 239000011734 sodium Substances 0.000 abstract description 12
- 229910052708 sodium Inorganic materials 0.000 abstract description 12
- 238000005580 one pot reaction Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 150000003961 organosilicon compounds Chemical class 0.000 abstract 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 6
- 230000009286 beneficial effect Effects 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000007818 Grignard reagent Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006136 alcoholysis reaction Methods 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- AUEJBKCWXPYRGZ-UHFFFAOYSA-N 1,1'-biphenyl diethoxysilane Chemical compound C(C)O[SiH2]OCC.C1(=CC=CC=C1)C1=CC=CC=C1 AUEJBKCWXPYRGZ-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- NOKUWSXLHXMAOM-UHFFFAOYSA-N hydroxy(phenyl)silicon Chemical compound O[Si]C1=CC=CC=C1 NOKUWSXLHXMAOM-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C 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 Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
The invention belongs to the technical field of organosilicon compound synthesis, and particularly relates to a method for preparing dialkoxydiphenylsilane through a direct method. The method comprises the steps that under the protection of inert gas, metallic sodium is added into a mixed solution of tetraalkoxysilane and a dispersing agent, the mixed solution is heated to the temperature of 97 DEG C-113 DEG C, and a metallic sodium particle suspension solution is prepared; under the condition of 25 DEG C-45 DEG C, halogenated-benzene is dropwise added into the metallic sodium particle suspension solution, reacting is performed for 3-5 h and then stopped, and after reacting is finished, reduced-pressure rectification is performed on a mixture to obtain the dialkoxydiphenylsilane product. According to the method, the direct method is adopted, a one-pot combination reaction of chlorobenzene, metallic sodium and tetraalkoxysilane is achieved, and then the target product is obtained; the whole reaction is low in temperature, easy to operate, mild and controllable.
Description
Technical field
The invention belongs to silicoorganic compound synthesis technical field, it is specifically related to a kind of method that direct method prepares phenylbenzene dialkoxy silicane.
Background technology
Phenylbenzene dialkoxy silicane is a kind of extremely important organosilicon functional compounds, is the important source material of manufacture phenyl silicone oil, phenyl siloxane rubber. Functional group is introduced in organosilicon material so that organosilicon material has great using value in fields such as national defence, aviation, chemical industry, medical treatment.
At present, the preparation method of dimethoxydiphenylsilane mainly contains two kinds i.e. alcoholysis method and Grignard. Chen Fade etc. adopt grignard reagent to prepare dimethoxydiphenylsilane in " Grignard synthesis dimethoxydiphenylsilane ", but the shortcoming of this kind of method is, reaction environment is required harsh by Grignard reagent, containing materials such as water, reaction impact is very big, and Grignard reagent is active high, easily occurring vigorous reaction even to explode, subsequent reactions product separation difficulty is big. Wu Guangwen etc. adopt alcoholysis method in " synthesising process research of dimethoxydiphenylsilane ". The method shortcoming is to use excessive methanol, generates a large amount of sour gas, and expensive raw material price and the reason such as the source of goods is limited, limit the all-round popularization of alcoholysis method.
Summary of the invention
It is an object of the invention to provide a kind of method that direct method prepares phenylbenzene dialkoxy silicane, whole reactive behavior height, fast, gentle controlled, be very beneficial for suitability for industrialized production.
Direct method of the present invention prepares the method for phenylbenzene dialkoxy silicane, and step is as follows:
(1) under the protection of rare gas element, sodium Metal 99.5 is added in the mixed solution of tetraalkoxysilane and dispersion agent, it is heated to 97-113 DEG C, it is preferable that 99-112 DEG C, be prepared into sodium Metal 99.5 particle suspension liquid;
(2) when 25-45 DEG C, it is preferable that 30-42 DEG C, being added drop-wise to by halogeno-benzene in sodium Metal 99.5 particle suspension liquid, reaction 3-5h, stopped reaction, reaction terminates rear mixture and carries out rectification under vacuum and obtain phenylbenzene dialkoxy silicane product.
Rare gas element described in step (1) is nitrogen or neon.
The mol ratio of the sodium Metal 99.5 described in step (1) and tetraalkoxysilane is 1:0.24-0.25.
Tetraalkoxysilane described in step (1) is tetramethoxy-silicane or tetraethoxysilane.
Dispersion agent described in step (1) is the one in Palmiticacid, paraffin or oleic acid.
The mass ratio of the dispersion agent described in step (1) and sodium Metal 99.5 is 1:100-150.
Halogeno-benzene described in step (2) is chlorobenzene or bromobenzene, it is preferable to chlorobenzene.
The mol ratio of the halogeno-benzene described in step (2) and sodium Metal 99.5 is 1.02:1.85-1.97.
Dispersion agent can play make sodium Metal 99.5 uniform particles be suspended in tetraalkoxysilane, stable existence and do not assemble, it make whole reaction high reactivity, fast, gentle controlled, be very beneficial for suitability for industrialized production.
The present invention adopts a kind of brand-new method, does not use any organic solvent, and raw material is reactant, is also reaction medium, its recovery utilization rate is extremely high, and single step reaction prepares phenylbenzene dialkoxy silicane, and reaction operates at ambient pressure, steadily controlled, simple to operate, it is beneficial to very much suitability for industrialized production. The structural formula of the product phenylbenzene dialkoxy silicane of the present invention is:
The present invention adopts direct method, it is achieved that one pot of combination reaction of chlorobenzene, sodium Metal 99.5, tetraalkoxysilane, obtains target product, and operation is simple. Under the effect of dispersion agent, the sodium Metal 99.5 that specific surface area is big is particle stabilized is present in suspension, ensure that the high reactivity of subsequent reactions, and then ensure that the high receipts rate of product. The whole reaction process of the present invention all carries out at the temperature of about 100 DEG C, simple to operate, gentle controlled, is very beneficial for industrialization. Raw material of the present invention is reactant and reaction medium, and can recycle fully, does not adopt organic solvent, and product is very easily separated. The present invention does not produce the corrosive gasess such as acid gas, safety and environmental protection. Sodium is exhausted by excessive chlorobenzene completely, eliminates the hidden danger of remaining sodium. The present invention directly adopts rectification under vacuum to achieve the high-level efficiency rectifying of raw material and product, obtains the product of high purity.
The present invention compared with prior art, has following useful effect:
1, the present invention adopts direct method, it is achieved that one pot of combination reaction of chlorobenzene, sodium Metal 99.5, tetraalkoxysilane, obtains target product.
2, the present invention adopts dispersion agent, ensure sodium particle in the solution stable existence and do not assemble, there is high reactivity simultaneously, be beneficial to very much the carrying out of reaction.
3, the whole temperature of reaction of the present invention is low, simple to operate, gentle controlled.
4, the present invention does not adopt any organic solvent, and raw material is reactant and reaction medium, and can recycle fully, and product is very easily separated.
5, the present invention does not produce the corrosive gasess such as acid gas, safety and environmental protection. Sodium is exhausted by excessive chlorobenzene completely, eliminates the hidden danger of remaining sodium.
Embodiment
Below in conjunction with embodiment, the present invention is described further.
Embodiment 1
Under nitrogen protection, 23g sodium block is shredded in the mixed solution being added to 36.53g tetramethoxy-silicane and 0.23g Palmiticacid, is heated to 99 DEG C, be prepared into sodium Metal 99.5 particle suspension liquid; When 30 DEG C, being added drop-wise in sodium Metal 99.5 particle suspension liquid by 60.81g chlorobenzene, reaction 5h, stopped reaction, reaction terminates rear mixture and carries out rectification under vacuum and obtain dimethoxydiphenylsilane product, and receipts rate is 82%.
Embodiment 2
Under nitrogen protection, 46g sodium block is shredded in the mixed solution being added to 141.28g tetraethoxysilane and 0.383g paraffin, is heated to 107 DEG C, be prepared into sodium Metal 99.5 particle suspension liquid; When 37 DEG C, being added drop-wise in sodium Metal 99.5 particle suspension liquid by 118.42g chlorobenzene, reaction 4h, stopped reaction, reaction terminates rear mixture and carries out rectification under vacuum and obtain phenylbenzene diethoxy silane product, and receipts rate is 77%.
Embodiment 3
Under nitrogen protection, 23g sodium block is shredded in the mixed solution being added to 38g tetramethoxy-silicane and 0.153g oleic acid, is heated to 112 DEG C, be prepared into sodium Metal 99.5 particle suspension liquid; When 42 DEG C, being added drop-wise in sodium Metal 99.5 particle suspension liquid by 51.7g chlorobenzene, reaction 3h, stopped reaction, reaction terminates rear mixture and carries out rectification under vacuum and obtain dimethoxydiphenylsilane product, and receipts rate is 61%.
Claims (8)
1. a direct method prepares the method for phenylbenzene dialkoxy silicane, it is characterised in that step is as follows:
(1) under the protection of rare gas element, sodium Metal 99.5 is added in the mixed solution of tetraalkoxysilane and dispersion agent, it is heated to 97-113 DEG C, be prepared into sodium Metal 99.5 particle suspension liquid;
(2) when 25-45 DEG C, being added drop-wise to by halogeno-benzene in sodium Metal 99.5 particle suspension liquid, reaction 3-5h, stopped reaction, reaction terminates rear mixture and carries out rectification under vacuum and obtain phenylbenzene dialkoxy silicane product.
2. direct method according to claim 1 prepares the method for phenylbenzene dialkoxy silicane, it is characterised in that the rare gas element described in step (1) is nitrogen or neon.
3. direct method according to claim 1 prepares the method for phenylbenzene dialkoxy silicane, it is characterised in that the mol ratio of the sodium Metal 99.5 described in step (1) and tetraalkoxysilane is 1:0.24-0.25.
4. direct method according to claim 1 prepares the method for phenylbenzene dialkoxy silicane, it is characterised in that the tetraalkoxysilane described in step (1) is tetramethoxy-silicane or tetraethoxysilane.
5. direct method according to claim 1 prepares the method for phenylbenzene dialkoxy silicane, it is characterised in that the dispersion agent described in step (1) is the one in Palmiticacid, paraffin or oleic acid.
6. direct method according to claim 1 prepares the method for phenylbenzene dialkoxy silicane, it is characterised in that the mass ratio of the dispersion agent described in step (1) and sodium Metal 99.5 is 1:100-150.
7. direct method according to claim 1 prepares the method for phenylbenzene dialkoxy silicane, it is characterised in that the halogeno-benzene described in step (2) is chlorobenzene or bromobenzene.
8. direct method according to claim 1 prepares the method for phenylbenzene dialkoxy silicane, it is characterised in that the mol ratio of the halogeno-benzene described in step (2) and sodium Metal 99.5 is 1.02:1.85-1.97.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610147710.6A CN105622662B (en) | 2016-03-16 | 2016-03-16 | The method that direct method prepares diphenyl dialkoxy silicane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610147710.6A CN105622662B (en) | 2016-03-16 | 2016-03-16 | The method that direct method prepares diphenyl dialkoxy silicane |
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| Publication Number | Publication Date |
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| CN105622662A true CN105622662A (en) | 2016-06-01 |
| CN105622662B CN105622662B (en) | 2019-01-11 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6172791A (en) * | 1984-09-17 | 1986-04-14 | Yuki Gosei Yakuhin Kogyo Kk | Production of dialkoxydiphenylsilane |
| CN101077877A (en) * | 2007-05-15 | 2007-11-28 | 盐城市华业医药化工有限公司 | Phenyl alkoxy silane prepared by sodium condensation method |
| CN104926858A (en) * | 2015-06-29 | 2015-09-23 | 山东东岳有机硅材料有限公司 | Method for preparing phenyl trialkyl alkoxy silane by nucleophilic method |
| CN105254659A (en) * | 2015-09-25 | 2016-01-20 | 山东东岳有机硅材料有限公司 | Nucleophilic method used for preparing phenylmethyldialkoxysilanes |
-
2016
- 2016-03-16 CN CN201610147710.6A patent/CN105622662B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6172791A (en) * | 1984-09-17 | 1986-04-14 | Yuki Gosei Yakuhin Kogyo Kk | Production of dialkoxydiphenylsilane |
| CN101077877A (en) * | 2007-05-15 | 2007-11-28 | 盐城市华业医药化工有限公司 | Phenyl alkoxy silane prepared by sodium condensation method |
| CN104926858A (en) * | 2015-06-29 | 2015-09-23 | 山东东岳有机硅材料有限公司 | Method for preparing phenyl trialkyl alkoxy silane by nucleophilic method |
| CN105254659A (en) * | 2015-09-25 | 2016-01-20 | 山东东岳有机硅材料有限公司 | Nucleophilic method used for preparing phenylmethyldialkoxysilanes |
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| CN105622662B (en) | 2019-01-11 |
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Address after: Tangshan Huantai County town of 256401 Shandong city of Zibo province Shandong Dongyue Group Technology Management Center Applicant after: Shandong Dongyue organosilicon material Limited by Share Ltd Address before: Tangshan Huantai County town of 256401 Shandong city of Zibo province Shandong Dongyue Group Technology Management Center Applicant before: Shandong Dongyue Silicon Material co., Ltd. |
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