CA1062273A - Process for the preparation of poly-(-n-alkylimino-alanes) - Google Patents
Process for the preparation of poly-(-n-alkylimino-alanes)Info
- Publication number
- CA1062273A CA1062273A CA232,551A CA232551A CA1062273A CA 1062273 A CA1062273 A CA 1062273A CA 232551 A CA232551 A CA 232551A CA 1062273 A CA1062273 A CA 1062273A
- Authority
- CA
- Canada
- Prior art keywords
- aluminium
- reaction
- amine
- poly
- alkaline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 229910000086 alane Inorganic materials 0.000 title claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 38
- 239000004411 aluminium Substances 0.000 claims abstract description 37
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 34
- 150000001412 amines Chemical class 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 239000002184 metal Substances 0.000 claims abstract description 13
- 239000000047 product Substances 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052751 metal Inorganic materials 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 150000004678 hydrides Chemical class 0.000 claims abstract description 5
- 150000002739 metals Chemical class 0.000 claims abstract description 5
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- 150000003141 primary amines Chemical class 0.000 claims abstract description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 239000012298 atmosphere Substances 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 3
- 230000000737 periodic effect Effects 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 239000002904 solvent Substances 0.000 claims description 16
- 239000002798 polar solvent Substances 0.000 claims description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 13
- -1 polyethylene Polymers 0.000 abstract description 11
- 229920000642 polymer Polymers 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000004698 Polyethylene Substances 0.000 abstract description 2
- 230000006698 induction Effects 0.000 abstract description 2
- 229920000573 polyethylene Polymers 0.000 abstract description 2
- 230000000707 stereoselective effect Effects 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 239000000725 suspension Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 238000005755 formation reaction Methods 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000786363 Rhampholeon spectrum Species 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000010908 decantation Methods 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 3
- 229910000091 aluminium hydride Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000036647 reaction Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 101100058670 Aeromonas hydrophila subsp. hydrophila (strain ATCC 7966 / DSM 30187 / BCRC 13018 / CCUG 14551 / JCM 1027 / KCTC 2358 / NCIMB 9240 / NCTC 8049) bsr gene Proteins 0.000 description 1
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 description 1
- NOQGZXFMHARMLW-UHFFFAOYSA-N Daminozide Chemical compound CN(C)NC(=O)CCC(O)=O NOQGZXFMHARMLW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 229910020828 NaAlH4 Inorganic materials 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000095 alkaline earth hydride Inorganic materials 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/10—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing aluminium
-
- 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
- C07F5/069—Aluminium compounds without C-aluminium linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25941/74A IT1017876B (it) | 1974-08-02 | 1974-08-02 | Processo per la preparazione di poli n.alchil.imminualani |
| IT2470675A IT1049446B (it) | 1975-06-24 | 1975-06-24 | Processo per la preparazione di poli n alchiliminoalani |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1062273A true CA1062273A (en) | 1979-09-11 |
Family
ID=26328532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA232,551A Expired CA1062273A (en) | 1974-08-02 | 1975-07-30 | Process for the preparation of poly-(-n-alkylimino-alanes) |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4296045A (en:Method) |
| JP (1) | JPS5139630A (en:Method) |
| AR (1) | AR210086A1 (en:Method) |
| AT (1) | AT343131B (en:Method) |
| BG (1) | BG40317A3 (en:Method) |
| BR (1) | BR7504833A (en:Method) |
| CA (1) | CA1062273A (en:Method) |
| CH (1) | CH615437A5 (en:Method) |
| DD (1) | DD120458A5 (en:Method) |
| DE (1) | DE2534471A1 (en:Method) |
| DK (1) | DK351175A (en:Method) |
| ES (1) | ES440495A1 (en:Method) |
| FR (1) | FR2280671A1 (en:Method) |
| GB (1) | GB1503925A (en:Method) |
| HU (1) | HU171957B (en:Method) |
| IE (1) | IE42334B1 (en:Method) |
| IL (1) | IL47849A (en:Method) |
| IN (1) | IN144264B (en:Method) |
| LU (1) | LU73101A1 (en:Method) |
| NL (1) | NL174054C (en:Method) |
| NO (1) | NO141315C (en:Method) |
| SE (1) | SE420924B (en:Method) |
| TR (1) | TR18429A (en:Method) |
| YU (1) | YU39030B (en:Method) |
| ZM (1) | ZM11375A1 (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1095573B (it) * | 1978-04-12 | 1985-08-10 | Snam Progetti | Derivati imminici oligomerici dell'idruro di alluminio e processi per la loro preparazione |
| CA1334475C (en) * | 1986-09-04 | 1995-02-21 | E.I. Du Pont De Nemours And Company | High purity aluminum nitride of controlled morphology |
| US5164263A (en) * | 1986-09-04 | 1992-11-17 | E. I. Du Pont De Nemours & Co. | Aluminum nitride flakes and spheres |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3651064A (en) * | 1970-01-12 | 1972-03-21 | Ethyl Corp | Process for preparing tertiary amine alanes |
| CS167751B1 (en:Method) * | 1974-03-28 | 1976-05-28 |
-
1975
- 1975-07-24 IE IE1662/75A patent/IE42334B1/en unknown
- 1975-07-25 GB GB31318/75A patent/GB1503925A/en not_active Expired
- 1975-07-25 YU YU01900/75A patent/YU39030B/xx unknown
- 1975-07-29 FR FR7523704A patent/FR2280671A1/fr active Granted
- 1975-07-29 BR BR7504833*A patent/BR7504833A/pt unknown
- 1975-07-29 TR TR18429A patent/TR18429A/xx unknown
- 1975-07-30 IN IN1501/CAL/75A patent/IN144264B/en unknown
- 1975-07-30 CA CA232,551A patent/CA1062273A/en not_active Expired
- 1975-07-30 CH CH995575A patent/CH615437A5/de not_active IP Right Cessation
- 1975-07-30 LU LU73101A patent/LU73101A1/xx unknown
- 1975-07-31 IL IL47849A patent/IL47849A/xx unknown
- 1975-07-31 ES ES440495A patent/ES440495A1/es not_active Expired
- 1975-07-31 DD DD187604A patent/DD120458A5/xx unknown
- 1975-08-01 ZM ZM113/75A patent/ZM11375A1/xx unknown
- 1975-08-01 AT AT600175A patent/AT343131B/de not_active IP Right Cessation
- 1975-08-01 HU HU75SA2828A patent/HU171957B/hu unknown
- 1975-08-01 DE DE19752534471 patent/DE2534471A1/de not_active Ceased
- 1975-08-01 SE SE7508746A patent/SE420924B/xx not_active IP Right Cessation
- 1975-08-01 NL NLAANVRAGE7509237,A patent/NL174054C/xx not_active IP Right Cessation
- 1975-08-01 AR AR259881A patent/AR210086A1/es active
- 1975-08-01 JP JP50093246A patent/JPS5139630A/ja active Pending
- 1975-08-01 NO NO752710A patent/NO141315C/no unknown
- 1975-08-01 DK DK351175A patent/DK351175A/da not_active Application Discontinuation
- 1975-08-02 BG BG030718A patent/BG40317A3/xx unknown
-
1977
- 1977-02-18 US US05/770,228 patent/US4296045A/en not_active Expired - Lifetime
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