NL8003152A - Werkwijze ter bereiding van trialkoxysilanolen. - Google Patents
Werkwijze ter bereiding van trialkoxysilanolen. Download PDFInfo
- Publication number
- NL8003152A NL8003152A NL8003152A NL8003152A NL8003152A NL 8003152 A NL8003152 A NL 8003152A NL 8003152 A NL8003152 A NL 8003152A NL 8003152 A NL8003152 A NL 8003152A NL 8003152 A NL8003152 A NL 8003152A
- Authority
- NL
- Netherlands
- Prior art keywords
- phase
- process according
- toluene
- pyridine
- organic
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 95
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 20
- 239000012071 phase Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000012074 organic phase Substances 0.000 claims description 16
- 239000008346 aqueous phase Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 150000007529 inorganic bases Chemical class 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000007530 organic bases Chemical group 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 229910008051 Si-OH Inorganic materials 0.000 claims description 4
- 229910006358 Si—OH Inorganic materials 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000006163 transport media Substances 0.000 claims 1
- RYFIHIMBHQWVNQ-UHFFFAOYSA-N tributoxy(chloro)silane Chemical compound CCCCO[Si](Cl)(OCCCC)OCCCC RYFIHIMBHQWVNQ-UHFFFAOYSA-N 0.000 claims 1
- 229940086542 triethylamine Drugs 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 28
- 150000004819 silanols Chemical class 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- -1 silicate ester compounds Chemical class 0.000 description 11
- 238000007792 addition Methods 0.000 description 10
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 10
- 239000007921 spray Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000005046 Chlorosilane Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229910020175 SiOH Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004337 3-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910018557 Si O Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- OBNDGIHQAIXEAO-UHFFFAOYSA-N [O].[Si] Chemical compound [O].[Si] OBNDGIHQAIXEAO-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- XWQLYVIMMBLXPY-UHFFFAOYSA-N butan-2-yloxysilane Chemical compound CCC(C)O[SiH3] XWQLYVIMMBLXPY-UHFFFAOYSA-N 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- IPFHPMNECZXQDM-UHFFFAOYSA-N tri(butan-2-yloxy)-hydroxysilane Chemical compound CCC(C)O[Si](O)(OC(C)CC)OC(C)CC IPFHPMNECZXQDM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- C07F7/04—Esters of silicic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/044,829 US4207247A (en) | 1979-06-01 | 1979-06-01 | Preparation of trialkoxysilanols |
| US4482979 | 1979-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8003152A true NL8003152A (nl) | 1980-12-03 |
Family
ID=21934556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8003152A NL8003152A (nl) | 1979-06-01 | 1980-05-30 | Werkwijze ter bereiding van trialkoxysilanolen. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4207247A (fr) |
| JP (1) | JPS5618990A (fr) |
| BE (1) | BE883580A (fr) |
| BR (1) | BR8003287A (fr) |
| CA (1) | CA1140144A (fr) |
| DE (1) | DE3020134A1 (fr) |
| ES (1) | ES8103758A1 (fr) |
| FR (1) | FR2457871A1 (fr) |
| GB (1) | GB2053254B (fr) |
| IT (1) | IT1133021B (fr) |
| NL (1) | NL8003152A (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62120390A (ja) * | 1985-11-20 | 1987-06-01 | Chisso Corp | テトラメトキシシランの製造方法 |
| DE3934100A1 (de) * | 1989-10-12 | 1991-04-18 | Bayer Ag | Verfahren zur herstellung von 0-silylierten hydroxylverbindungen und ihre verwendung zur herstellung von estergruppen aufweisenden isocyanaten |
| JP2830731B2 (ja) * | 1994-02-23 | 1998-12-02 | 信越化学工業株式会社 | シラノール基を有するオルガノシランの製造方法 |
| JPH10273490A (ja) * | 1997-03-28 | 1998-10-13 | Toray Dow Corning Silicone Co Ltd | ラジカル重合性基含有シラノール化合物の製造方法 |
| DE10148894A1 (de) * | 2001-10-04 | 2003-04-30 | Fraunhofer Ges Forschung | Photochemisch und/oder thermisch strukturierbare Harze auf Silanbasis, einstufiges Verfahren zu deren Herstellung, dabei einzetzbare Ausgangsverbindungen und Herstellungsverfahren für diese |
| CN108948061A (zh) * | 2018-06-01 | 2018-12-07 | 杭州师范大学 | 一种芳基三（三r基硅氧烷基）硅烷的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB709346A (en) * | 1950-08-28 | 1954-05-19 | California Research Corp | Alkoxysilanols and alkoxysiloxanols and processes for making the same |
| US2758127A (en) * | 1953-12-30 | 1956-08-07 | California Research Corp | Method of preparing silicon esters by reacting an alkoxysilanol with an alkoxysilamine |
| US2727054A (en) * | 1954-08-24 | 1955-12-13 | California Research Corp | Method of preparing silicate esters |
| US3965136A (en) * | 1975-09-24 | 1976-06-22 | Olin Corporation | Alkoxysilane cluster compounds and their preparation |
| US3965135A (en) * | 1975-09-24 | 1976-06-22 | Olin Corporation | Alkoxysilanol cluster compounds and their preparation |
| US4077993A (en) * | 1977-04-27 | 1978-03-07 | Olin Corporation | Method for the preparation of alkoxysilane cluster compounds |
-
1979
- 1979-06-01 US US06/044,829 patent/US4207247A/en not_active Expired - Lifetime
-
1980
- 1980-05-13 CA CA000351830A patent/CA1140144A/fr not_active Expired
- 1980-05-27 DE DE19803020134 patent/DE3020134A1/de not_active Withdrawn
- 1980-05-27 BR BR8003287A patent/BR8003287A/pt unknown
- 1980-05-27 GB GB8017254A patent/GB2053254B/en not_active Expired
- 1980-05-28 IT IT48820/80A patent/IT1133021B/it active
- 1980-05-30 FR FR8012090A patent/FR2457871A1/fr active Pending
- 1980-05-30 NL NL8003152A patent/NL8003152A/nl not_active Application Discontinuation
- 1980-05-30 BE BE0/200846A patent/BE883580A/fr unknown
- 1980-05-30 ES ES491999A patent/ES8103758A1/es not_active Expired
- 1980-05-31 JP JP7218080A patent/JPS5618990A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE3020134A1 (de) | 1980-12-18 |
| US4207247A (en) | 1980-06-10 |
| IT1133021B (it) | 1986-07-09 |
| IT8048820A0 (it) | 1980-05-28 |
| ES491999A0 (es) | 1981-03-16 |
| BE883580A (fr) | 1980-09-15 |
| GB2053254A (en) | 1981-02-04 |
| FR2457871A1 (fr) | 1980-12-26 |
| GB2053254B (en) | 1983-12-21 |
| CA1140144A (fr) | 1983-01-25 |
| BR8003287A (pt) | 1980-12-30 |
| JPS5618990A (en) | 1981-02-23 |
| ES8103758A1 (es) | 1981-03-16 |
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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 | ||
| BV | The patent application has lapsed |