CN1045445C - 三芳基硼烷的制备 - Google Patents
三芳基硼烷的制备 Download PDFInfo
- Publication number
- CN1045445C CN1045445C CN95193748A CN95193748A CN1045445C CN 1045445 C CN1045445 C CN 1045445C CN 95193748 A CN95193748 A CN 95193748A CN 95193748 A CN95193748 A CN 95193748A CN 1045445 C CN1045445 C CN 1045445C
- Authority
- CN
- China
- Prior art keywords
- triarylborane
- bph
- phenyl
- catalyst residue
- formula
- 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 - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 238000009833 condensation Methods 0.000 claims abstract description 4
- 230000005494 condensation Effects 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052786 argon Inorganic materials 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 150000002815 nickel Chemical class 0.000 abstract description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 24
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 12
- 238000005669 hydrocyanation reaction Methods 0.000 description 11
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- -1 hexichol boron derivative Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 2
- ISBHMJZRKAFTGE-ONEGZZNKSA-N (e)-pent-2-enenitrile Chemical compound CC\C=C\C#N ISBHMJZRKAFTGE-ONEGZZNKSA-N 0.000 description 1
- GDCJAPJJFZWILF-UHFFFAOYSA-N 2-ethylbutanedinitrile Chemical compound CCC(C#N)CC#N GDCJAPJJFZWILF-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CGXMHTSTPOVZJU-UHFFFAOYSA-N P(O)(O)O.CC=1C(=C(C=CC1)C)C Chemical compound P(O)(O)O.CC=1C(=C(C=CC1)C)C CGXMHTSTPOVZJU-UHFFFAOYSA-N 0.000 description 1
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
Images
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
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/264,275 | 1994-06-23 | ||
| US08/264,275 US5382697A (en) | 1994-06-23 | 1994-06-23 | Preparation of triarylborane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1151163A CN1151163A (zh) | 1997-06-04 |
| CN1045445C true CN1045445C (zh) | 1999-10-06 |
Family
ID=23005324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95193748A Expired - Lifetime CN1045445C (zh) | 1994-06-23 | 1995-06-19 | 三芳基硼烷的制备 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5382697A (enExample) |
| EP (1) | EP0766686B1 (enExample) |
| JP (1) | JP3701677B2 (enExample) |
| KR (1) | KR100353777B1 (enExample) |
| CN (1) | CN1045445C (enExample) |
| DE (1) | DE69502395T2 (enExample) |
| MX (1) | MX9606723A (enExample) |
| TW (1) | TW320633B (enExample) |
| WO (1) | WO1996000227A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2849027B1 (fr) * | 2002-12-23 | 2005-01-21 | Rhodia Polyamide Intermediates | Procede de synthese de composes comprenant des fonctions nitriles a partir de composes a insaturations ethyleniques |
| FR2850966B1 (fr) | 2003-02-10 | 2005-03-18 | Rhodia Polyamide Intermediates | Procede de fabrication de composes dinitriles |
| FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
| FR2854892B1 (fr) * | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
| US7629484B2 (en) * | 2006-03-17 | 2009-12-08 | Invista North America S.A.R.L. | Method for the purification of triorganophosphites by treatment with a basic additive |
| US7709674B2 (en) * | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L | Hydrocyanation process with reduced yield losses |
| CN102241698B (zh) * | 2011-05-23 | 2013-12-25 | 中国科学院理化技术研究所 | 星形三芳基硼烷类化合物及其制备方法和用途 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4082811A (en) * | 1977-02-23 | 1978-04-04 | E. I. Du Pont De Nemours And Company | Recovery of metal and triarylborane catalyst components from olefin hydrocyanation residue |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3798256A (en) * | 1971-08-02 | 1974-03-19 | Du Pont | Hydrocyanation of olefins |
| US4134923A (en) * | 1977-09-02 | 1979-01-16 | E. I. Du Pont De Nemours And Company | Process for producing a metal hydroxide adduct of a triarylborane |
| US4394321A (en) * | 1981-11-12 | 1983-07-19 | E. I. Du Pont De Nemours And Company | Triarylboraneisocy ano metal compounds |
| US4416824A (en) * | 1981-12-21 | 1983-11-22 | E. I. Du Pont De Nemours & Co. | Recovery of triarylboranes by forming boron-containing metal compounds |
| US4749801A (en) * | 1986-06-04 | 1988-06-07 | E. I. Du Pont De Nemours And Company | [Hexakis(pentenenitrilo)nickel II]bis-[μ-(cyano) bis(triphenylborane) (I)], its method of preparation and its use |
| US4847399A (en) * | 1987-01-23 | 1989-07-11 | Morton Thiokol, Inc. | Process for preparing or purifying Group III-A organometallic compounds |
-
1994
- 1994-06-23 US US08/264,275 patent/US5382697A/en not_active Expired - Lifetime
-
1995
- 1995-05-31 TW TW084105504A patent/TW320633B/zh not_active IP Right Cessation
- 1995-06-19 EP EP95922972A patent/EP0766686B1/en not_active Expired - Lifetime
- 1995-06-19 CN CN95193748A patent/CN1045445C/zh not_active Expired - Lifetime
- 1995-06-19 JP JP50317896A patent/JP3701677B2/ja not_active Expired - Fee Related
- 1995-06-19 DE DE69502395T patent/DE69502395T2/de not_active Expired - Lifetime
- 1995-06-19 MX MX9606723A patent/MX9606723A/es not_active Application Discontinuation
- 1995-06-19 KR KR1019960707332A patent/KR100353777B1/ko not_active Expired - Lifetime
- 1995-06-19 WO PCT/US1995/007127 patent/WO1996000227A1/en not_active Ceased
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4082811A (en) * | 1977-02-23 | 1978-04-04 | E. I. Du Pont De Nemours And Company | Recovery of metal and triarylborane catalyst components from olefin hydrocyanation residue |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3701677B2 (ja) | 2005-10-05 |
| DE69502395T2 (de) | 1999-01-07 |
| US5382697A (en) | 1995-01-17 |
| TW320633B (enExample) | 1997-11-21 |
| WO1996000227A1 (en) | 1996-01-04 |
| JPH10502080A (ja) | 1998-02-24 |
| EP0766686B1 (en) | 1998-05-06 |
| DE69502395D1 (de) | 1998-06-10 |
| CN1151163A (zh) | 1997-06-04 |
| EP0766686A1 (en) | 1997-04-09 |
| KR100353777B1 (ko) | 2003-01-06 |
| MX9606723A (es) | 1997-03-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| ASS | Succession or assignment of patent right |
Owner name: INVISTA TECH SARL Free format text: FORMER OWNER: E. I. DU PONT DE NEMOURS AND CO. Effective date: 20051223 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20051223 Address after: Zurich Switzerland Patentee after: INVISTA TECHNOLOGIES S.A.R.L. Address before: Delaware, USA Patentee before: E. I. du Pont de Nemours and Co. |
|
| C17 | Cessation of patent right | ||
| CX01 | Expiry of patent term |
Expiration termination date: 20150619 Granted publication date: 19991006 |