NL9500553A - Werkwijze ter bereiding van dimethylamineboraan. - Google Patents
Werkwijze ter bereiding van dimethylamineboraan. Download PDFInfo
- Publication number
- NL9500553A NL9500553A NL9500553A NL9500553A NL9500553A NL 9500553 A NL9500553 A NL 9500553A NL 9500553 A NL9500553 A NL 9500553A NL 9500553 A NL9500553 A NL 9500553A NL 9500553 A NL9500553 A NL 9500553A
- Authority
- NL
- Netherlands
- Prior art keywords
- dimethylamine
- acid
- organic solvent
- reaction
- added
- Prior art date
Links
- RJTANRZEWTUVMA-UHFFFAOYSA-N boron;n-methylmethanamine Chemical compound [B].CNC RJTANRZEWTUVMA-UHFFFAOYSA-N 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title description 10
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 67
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 11
- -1 hydrogen halides Chemical class 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 239000002518 antifoaming agent Substances 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 150000008051 alkyl sulfates Chemical class 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 150000001412 amines Chemical class 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 5
- 229910000085 borane Inorganic materials 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- CWLIWRWKTAVPMN-UHFFFAOYSA-N dimethylazanium;sulfate Chemical compound C[NH2+]C.C[NH2+]C.[O-]S([O-])(=O)=O CWLIWRWKTAVPMN-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000003799 water insoluble solvent Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 229910020886 NaBH2 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005234 chemical deposition Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- QHNXEVRKFKHMRL-UHFFFAOYSA-N dimethylazanium;acetate Chemical compound CNC.CC(O)=O QHNXEVRKFKHMRL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012811 non-conductive material Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000004304 visual acuity Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4411752 | 1994-04-06 | ||
| DE4411752A DE4411752C1 (de) | 1994-04-06 | 1994-04-06 | Verfahren zur Herstellung von Dimethylaminboran |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL9500553A true NL9500553A (nl) | 1995-11-01 |
Family
ID=6514688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL9500553A NL9500553A (nl) | 1994-04-06 | 1995-03-22 | Werkwijze ter bereiding van dimethylamineboraan. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5565615A (ja) |
| JP (1) | JPH07278156A (ja) |
| CZ (1) | CZ87295A3 (ja) |
| DE (1) | DE4411752C1 (ja) |
| FI (1) | FI951598A (ja) |
| NL (1) | NL9500553A (ja) |
| RU (1) | RU2149874C1 (ja) |
| SK (1) | SK45395A3 (ja) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4441064C1 (de) * | 1994-11-18 | 1996-07-18 | Metallgesellschaft Ag | Verfahren zur Herstellung von Alkaliaminoborhydriden und Alkaliaminoborhydrid-Komplexen und deren Verwendung |
| RU2101285C1 (ru) * | 1996-11-20 | 1998-01-10 | Открытое акционерное общество "Авиабор" Дзержинский опытный завод авиационных материалов | Способ очистки диметиламинборана |
| JP2000204094A (ja) * | 1999-01-08 | 2000-07-25 | Shiroi Yakuhin Kk | アミンボランの製造方法 |
| US20040147781A1 (en) * | 2003-01-24 | 2004-07-29 | Kuo Ching Chemical Co., Ltd. | Process for producing organic amine borane compounds |
| EP2189463B1 (en) * | 2008-11-25 | 2012-07-04 | Rohm and Haas Company | Synthesis of amine boranes |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2927133A (en) * | 1957-08-13 | 1960-03-01 | Metal Hydrides Inc | Preparation of amine boranes |
| DE1618387A1 (de) * | 1967-03-15 | 1970-12-17 | Bayer Ag | Verfahren zur kontinuierlichen Herstellung von N-substituierten Borazanen |
| WO1993025544A1 (en) * | 1992-06-18 | 1993-12-23 | Boulder Scientific Company | Process for producing amine-boranes |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB826558A (en) * | 1956-02-13 | 1960-01-13 | Callery Chemical Co | Production of stable dimethylamine-borine |
| DE1178077B (de) * | 1957-09-21 | 1964-09-17 | Dieter Goerrig Dipl Chem Dr | Verfahren zur Herstellung von Bor-Stickstoff-Verbindungen |
| JPS60149593A (ja) * | 1984-01-12 | 1985-08-07 | Nippon Tokushu Kagaku Kogyo Kk | アミンボラン類の製造方法 |
| US4709083A (en) * | 1986-05-19 | 1987-11-24 | The United States Of America As Represented By The Secretary Of The Army | Method of making boron analogues |
-
1994
- 1994-04-06 DE DE4411752A patent/DE4411752C1/de not_active Expired - Fee Related
-
1995
- 1995-03-22 NL NL9500553A patent/NL9500553A/nl active Search and Examination
- 1995-03-30 US US08/413,681 patent/US5565615A/en not_active Expired - Fee Related
- 1995-03-31 JP JP7097638A patent/JPH07278156A/ja active Pending
- 1995-04-04 FI FI951598A patent/FI951598A/fi unknown
- 1995-04-05 RU RU95104897A patent/RU2149874C1/ru active
- 1995-04-05 CZ CZ95872A patent/CZ87295A3/cs unknown
- 1995-04-05 SK SK453-95A patent/SK45395A3/sk unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2927133A (en) * | 1957-08-13 | 1960-03-01 | Metal Hydrides Inc | Preparation of amine boranes |
| DE1618387A1 (de) * | 1967-03-15 | 1970-12-17 | Bayer Ag | Verfahren zur kontinuierlichen Herstellung von N-substituierten Borazanen |
| WO1993025544A1 (en) * | 1992-06-18 | 1993-12-23 | Boulder Scientific Company | Process for producing amine-boranes |
Non-Patent Citations (1)
| Title |
|---|
| NOTH, H. ET AL.: "BEITRAGE ZUR CHEMIE DES BORS, I. DARSTELLUNG UND EIGENSCHAFTEN DER ALKYLAMIN-BORANE, R3-nHnN.BH3", CHEMISCHE BERICHTE, vol. 93, 1960, pages 928 - 938 * |
Also Published As
| Publication number | Publication date |
|---|---|
| FI951598A (fi) | 1995-10-07 |
| RU2149874C1 (ru) | 2000-05-27 |
| FI951598A0 (fi) | 1995-04-04 |
| US5565615A (en) | 1996-10-15 |
| RU95104897A (ru) | 1997-01-10 |
| DE4411752C1 (de) | 1995-11-23 |
| JPH07278156A (ja) | 1995-10-24 |
| SK45395A3 (en) | 1995-10-11 |
| CZ87295A3 (en) | 1995-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1A | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BN | A decision not to publish the application has become irrevocable |