DE102008002182A1 - Verfahren zur Herstellung von Alkylaminoalkylalkoxysilanen - Google Patents
Verfahren zur Herstellung von Alkylaminoalkylalkoxysilanen Download PDFInfo
- Publication number
- DE102008002182A1 DE102008002182A1 DE102008002182A DE102008002182A DE102008002182A1 DE 102008002182 A1 DE102008002182 A1 DE 102008002182A1 DE 102008002182 A DE102008002182 A DE 102008002182A DE 102008002182 A DE102008002182 A DE 102008002182A DE 102008002182 A1 DE102008002182 A1 DE 102008002182A1
- Authority
- DE
- Germany
- Prior art keywords
- product
- alkyl group
- alkylamine
- linear
- branched
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910009257 Y—Si Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 53
- 239000000047 product Substances 0.000 claims description 48
- 238000004821 distillation Methods 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 16
- XCOASYLMDUQBHW-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)butan-1-amine Chemical compound CCCCNCCC[Si](OC)(OC)OC XCOASYLMDUQBHW-UHFFFAOYSA-N 0.000 claims description 15
- 239000012071 phase Substances 0.000 claims description 14
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 claims description 12
- 239000012074 organic phase Substances 0.000 claims description 10
- -1 alkali metal alkoxide Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- JYOXVRKGEPVYEA-UHFFFAOYSA-N (2-chloro-4-methylpentan-2-yl)oxy-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)OC(C)(Cl)CC(C)C JYOXVRKGEPVYEA-UHFFFAOYSA-N 0.000 claims description 2
- ARBWSQWFKWFAIW-UHFFFAOYSA-N (3-chloro-2-methylpropyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)CC(C)CCl ARBWSQWFKWFAIW-UHFFFAOYSA-N 0.000 claims description 2
- GMRPVPAENUZIQZ-UHFFFAOYSA-N 1-chloroethoxy-dimethyl-(2-methylpropyl)silane Chemical compound CC(C)C[Si](C)(C)OC(C)Cl GMRPVPAENUZIQZ-UHFFFAOYSA-N 0.000 claims description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 2
- IKBFHCBHLOZDKH-UHFFFAOYSA-N 2-chloroethyl(triethoxy)silane Chemical compound CCO[Si](CCCl)(OCC)OCC IKBFHCBHLOZDKH-UHFFFAOYSA-N 0.000 claims description 2
- CASYTJWXPQRCFF-UHFFFAOYSA-N 2-chloroethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCl CASYTJWXPQRCFF-UHFFFAOYSA-N 0.000 claims description 2
- PZTIZDBYLCQIEI-UHFFFAOYSA-N 2-chloroethyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(CCCl)OCC PZTIZDBYLCQIEI-UHFFFAOYSA-N 0.000 claims description 2
- SGFSMOHWPOFZQW-UHFFFAOYSA-N 2-chloroethyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCl SGFSMOHWPOFZQW-UHFFFAOYSA-N 0.000 claims description 2
- MGLQRAQKKGYLPA-UHFFFAOYSA-N 2-chloroethyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)CCCl MGLQRAQKKGYLPA-UHFFFAOYSA-N 0.000 claims description 2
- JPUCXJPPHJORGK-UHFFFAOYSA-N 2-chloroethyl-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)CCCl JPUCXJPPHJORGK-UHFFFAOYSA-N 0.000 claims description 2
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 claims description 2
- KEZMLECYELSZDC-UHFFFAOYSA-N 3-chloropropyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(OCC)CCCCl KEZMLECYELSZDC-UHFFFAOYSA-N 0.000 claims description 2
- KNTKCYKJRSMRMZ-UHFFFAOYSA-N 3-chloropropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCCl KNTKCYKJRSMRMZ-UHFFFAOYSA-N 0.000 claims description 2
- IIFBEYQLKOBDQH-UHFFFAOYSA-N 3-chloropropyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)CCCCl IIFBEYQLKOBDQH-UHFFFAOYSA-N 0.000 claims description 2
- JTWDWVCNOLORBR-UHFFFAOYSA-N 3-chloropropyl-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)CCCCl JTWDWVCNOLORBR-UHFFFAOYSA-N 0.000 claims description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 2
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 claims description 2
- ZLTKTTFPYAIZCV-UHFFFAOYSA-N chloromethoxy-dimethyl-(2-methylpropyl)silane Chemical compound CC(C)C[Si](C)(C)OCCl ZLTKTTFPYAIZCV-UHFFFAOYSA-N 0.000 claims description 2
- ZMZCDKKVGLGCSJ-UHFFFAOYSA-N chloromethoxy-methoxy-methyl-(2-methylpropyl)silane Chemical compound CC(C)C[Si](C)(OC)OCCl ZMZCDKKVGLGCSJ-UHFFFAOYSA-N 0.000 claims description 2
- ZDOBWJOCPDIBRZ-UHFFFAOYSA-N chloromethyl(triethoxy)silane Chemical compound CCO[Si](CCl)(OCC)OCC ZDOBWJOCPDIBRZ-UHFFFAOYSA-N 0.000 claims description 2
- FPOSCXQHGOVVPD-UHFFFAOYSA-N chloromethyl(trimethoxy)silane Chemical compound CO[Si](CCl)(OC)OC FPOSCXQHGOVVPD-UHFFFAOYSA-N 0.000 claims description 2
- XGLLBUISUZEUMW-UHFFFAOYSA-N chloromethyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(CCl)OCC XGLLBUISUZEUMW-UHFFFAOYSA-N 0.000 claims description 2
- ZXZMFKUGAPMMCJ-UHFFFAOYSA-N chloromethyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(CCl)OC ZXZMFKUGAPMMCJ-UHFFFAOYSA-N 0.000 claims description 2
- IGMQAYXTTRYCPZ-UHFFFAOYSA-N chloromethyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)CCl IGMQAYXTTRYCPZ-UHFFFAOYSA-N 0.000 claims description 2
- ZCSLOBFDVTWIBL-UHFFFAOYSA-N chloromethyl-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)CCl ZCSLOBFDVTWIBL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- KFOZMMAXUUCIKU-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)butan-1-amine Chemical compound CCCCNCCC[Si](OCC)(OCC)OCC KFOZMMAXUUCIKU-UHFFFAOYSA-N 0.000 claims description 2
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 claims description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims description 2
- HBXNJMZWGSCKPW-UHFFFAOYSA-N octan-2-amine Chemical compound CCCCCCC(C)N HBXNJMZWGSCKPW-UHFFFAOYSA-N 0.000 claims description 2
- IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical compound CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 0.000 claims description 2
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 2
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 claims description 2
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 125000004429 atom Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- BIGOJJYDFLNSGB-UHFFFAOYSA-N 3-isocyanopropyl(trimethoxy)silane Chemical group CO[Si](OC)(OC)CCC[N+]#[C-] BIGOJJYDFLNSGB-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000003940 butylamines Chemical group 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001165 gas chromatography-thermal conductivity detection Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- LUCUIQANGOWOGY-UHFFFAOYSA-N n,n-bis(3-triethoxysilylpropyl)butan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCN(CCCC)CCC[Si](OCC)(OCC)OCC LUCUIQANGOWOGY-UHFFFAOYSA-N 0.000 description 2
- PUBDUWLUQQHMTP-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)butan-1-amine;hydrochloride Chemical compound Cl.CCCCNCCC[Si](OC)(OC)OC PUBDUWLUQQHMTP-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- BUHVIAUBTBOHAG-FOYDDCNASA-N (2r,3r,4s,5r)-2-[6-[[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound COC1=CC(OC)=CC(C(CNC=2C=3N=CN(C=3N=CN=2)[C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C=2C(=CC=CC=2)C)=C1 BUHVIAUBTBOHAG-FOYDDCNASA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NUNGAAHSDAQGSU-UHFFFAOYSA-N N-(3-silylpropyl)butan-1-amine Chemical compound CCCCNCCC[SiH3] NUNGAAHSDAQGSU-UHFFFAOYSA-N 0.000 description 1
- MWXPTZRPGFZECR-UHFFFAOYSA-N N-(3-silylpropyl)butan-1-amine hydrochloride Chemical compound Cl.CCCCNCCC[SiH3] MWXPTZRPGFZECR-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JPZAYXNLNMYCAK-UHFFFAOYSA-N n-propylbutan-1-amine;hydrochloride Chemical compound Cl.CCCCNCCC JPZAYXNLNMYCAK-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 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
-
- 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
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- 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
- C07F7/20—Purification, separation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008002182A DE102008002182A1 (de) | 2008-06-03 | 2008-06-03 | Verfahren zur Herstellung von Alkylaminoalkylalkoxysilanen |
| US12/995,852 US8426628B2 (en) | 2008-06-03 | 2009-04-17 | Process for preparing alkylaminoalkylalkoxysilanes |
| ES09757354T ES2427767T3 (es) | 2008-06-03 | 2009-04-17 | Procedimiento para la preparación de alquilaminoalquilalcoxisilanos |
| KR1020107027077A KR101589326B1 (ko) | 2008-06-03 | 2009-04-17 | 알킬아미노알킬알콕시실란의 제조 방법 |
| EP09757354.7A EP2307428B1 (de) | 2008-06-03 | 2009-04-17 | Verfahren zur herstellung von alkylaminoalkylalkoxysilanen |
| JP2011512044A JP5345682B2 (ja) | 2008-06-03 | 2009-04-17 | アルキルアミノアルキルアルコキシシランの製造法 |
| PCT/EP2009/054587 WO2009146971A1 (de) | 2008-06-03 | 2009-04-17 | Verfahren zur herstellung von alkylaminoalkylalkoxysilanen |
| CN200910141347.7A CN101597302B (zh) | 2008-06-03 | 2009-06-02 | 制备烷基氨基烷基烷氧基硅烷的方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008002182A DE102008002182A1 (de) | 2008-06-03 | 2008-06-03 | Verfahren zur Herstellung von Alkylaminoalkylalkoxysilanen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102008002182A1 true DE102008002182A1 (de) | 2009-12-10 |
Family
ID=40743892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102008002182A Withdrawn DE102008002182A1 (de) | 2008-06-03 | 2008-06-03 | Verfahren zur Herstellung von Alkylaminoalkylalkoxysilanen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8426628B2 (https=) |
| EP (1) | EP2307428B1 (https=) |
| JP (1) | JP5345682B2 (https=) |
| KR (1) | KR101589326B1 (https=) |
| CN (1) | CN101597302B (https=) |
| DE (1) | DE102008002182A1 (https=) |
| ES (1) | ES2427767T3 (https=) |
| WO (1) | WO2009146971A1 (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102015225879A1 (de) | 2015-12-18 | 2017-06-22 | Evonik Degussa Gmbh | Tris-(alkylalkoxysilyl)amin-reiche Zusammensetzungen, deren Herstellung und deren Verwendung |
| DE102015225883A1 (de) | 2015-12-18 | 2017-06-22 | Evonik Degussa Gmbh | Bis(alkylalkoxysilyl)amin-reiche Zusammensetzungen, ein Verfahren zur deren Herstellung und deren Verwendung |
| DE102016215260A1 (de) | 2016-08-16 | 2018-02-22 | Evonik Degussa Gmbh | Verwendung einer (Alkylalkoxysily)amin-, Bis-(alkylalkoxysilyl)amin und/oder Tris-(alkylalkoxysilyl)amin-enthaltenden Zusammensetzung |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008002181A1 (de) * | 2008-06-03 | 2009-12-10 | Evonik Degussa Gmbh | Verfahren zur wässrigen Aufarbeitung eines Ammoniumhalogenide und/oder organische Aminhydrohalogenide enthaltenden aminofunktionellen Organosilans |
| DE102008002183A1 (de) * | 2008-06-03 | 2009-12-10 | Evonik Degussa Gmbh | Verfahren zur Aufarbeitung salzhaltiger Rückstände aus der Herstellung von aminofunktionellen Organosilanen |
| CN102250135A (zh) * | 2011-05-19 | 2011-11-23 | 安徽硅宝翔飞有机硅新材料有限公司 | 一种仲胺基硅烷偶联剂的制备方法 |
| CN102558218B (zh) * | 2011-12-16 | 2015-04-01 | 齐鲁工业大学 | 一种叔胺基硅烷的制备方法 |
| CN102558219B (zh) * | 2011-12-16 | 2015-04-01 | 齐鲁工业大学 | 一种叔胺基硅烷的生产工艺 |
| CN102775433B (zh) * | 2012-04-08 | 2015-08-12 | 荆州市江汉精细化工有限公司 | 一种3-(苯基氨基)丙基烷氧基硅烷的制备及副产物的回收利用工艺 |
| CN103880875B (zh) * | 2012-12-19 | 2017-04-05 | 张家港市国泰华荣化工新材料有限公司 | 一种固砂偶联剂的制备方法 |
| CN104926852A (zh) * | 2014-03-19 | 2015-09-23 | 张家港市国泰华荣化工新材料有限公司 | 正丁胺基丙基三甲氧基硅烷的制备方法 |
| EP3216813A1 (de) | 2016-03-10 | 2017-09-13 | Evonik Degussa GmbH | Verwendung eines n-(n-butyl)-3-aminopropylmethydialkoxysilans in silanterminierten polyurethanen für elastische kleb- und dichtstoffe |
| KR101985821B1 (ko) * | 2016-05-03 | 2019-06-05 | 주식회사 엘지화학 | 아미노실란계 화합물의 신규 제조방법 |
| CN105837616A (zh) * | 2016-05-19 | 2016-08-10 | 南京齐正化学有限公司 | N,n-二乙基-3-氨丙基三甲氧基硅烷的制备方法 |
| DE102018210886A1 (de) | 2018-07-03 | 2020-01-09 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Alkylalkoxysilanen |
| KR102841320B1 (ko) * | 2022-09-06 | 2025-08-01 | 금호석유화학 주식회사 | 아미노알콕시실란 화합물의 제조방법 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10140563A1 (de) | 2001-08-18 | 2003-02-27 | Degussa | Verfahren zur Herstellung von aminofunktionellen Organosilanen |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5112608B2 (https=) * | 1973-05-29 | 1976-04-21 | ||
| DE2521399A1 (de) * | 1975-05-14 | 1976-11-25 | Bayer Ag | Verfahren zur herstellung von aminoalkylsilanen |
| DE2753124A1 (de) * | 1977-11-29 | 1979-06-07 | Dynamit Nobel Ag | Verfahren zur herstellung von aminoalkylsilanen |
| DE4130643A1 (de) * | 1991-09-14 | 1993-03-18 | Degussa | Verfahren zur reinigung von alkoxysilanen |
| EP0702017B1 (de) * | 1994-09-14 | 2001-11-14 | Degussa AG | Verfahren zur Herstellung von chloridarmen bzw. chloridfreien aminofunktionellen Organosilanen |
| DE19516386A1 (de) * | 1995-05-04 | 1996-11-07 | Huels Chemische Werke Ag | Verfahren zur Herstellung von an chlorfunktionellen Organosilanen armen bzw. freien aminofunktionellen Organosilanen |
| DE19849196A1 (de) | 1998-10-26 | 2000-04-27 | Degussa | Verfahren zur Neutralisation und Minderung von Resthalogengehalten in Alkoxysilanen oder Alkoxysilan-basierenden Zusammensetzungen |
| ATE284406T1 (de) | 1998-11-06 | 2004-12-15 | Degussa | Verfahren zur herstellung von chloridarmen oder chloridfreien alkoxysilanen |
| DE10058620A1 (de) * | 2000-11-25 | 2002-05-29 | Degussa | Verfahren zur Herstellung von Aminoalkylsilanen |
| DE10126669A1 (de) | 2001-06-01 | 2002-12-05 | Degussa | Verfahren zur Spaltung von cyclischen Organosilanen bei der Herstellung von aminofunktionellen Organoalkoxysilanen |
| DE10143568C2 (de) | 2001-09-05 | 2003-07-03 | Degussa | Verfahren zur Behandlung von Aminosilanverfärbungen |
| DE10353063B4 (de) * | 2003-11-13 | 2006-03-02 | Wacker-Chemie Gmbh | Verfahren zur Herstellung von (N-Organylaminoorganyl)- und (N,N-Diorganylaminoorganyl)triorganylsilanen sowie (N-Cyclohexylaminomethyl)trimethoxysilan und [N,N-Bis-(N',N'-dimethylaminopropyl)aminomethyl]triorganylsilan erhältliche mittels dieses Verfahrens |
| DE102004060627A1 (de) * | 2004-12-16 | 2006-07-06 | Wacker Chemie Ag | Verfahren zur kontinuierlichen Herstellung von Amino-Gruppen tragenden Silicium-Verbindungen |
| DE102008002181A1 (de) * | 2008-06-03 | 2009-12-10 | Evonik Degussa Gmbh | Verfahren zur wässrigen Aufarbeitung eines Ammoniumhalogenide und/oder organische Aminhydrohalogenide enthaltenden aminofunktionellen Organosilans |
-
2008
- 2008-06-03 DE DE102008002182A patent/DE102008002182A1/de not_active Withdrawn
-
2009
- 2009-04-17 JP JP2011512044A patent/JP5345682B2/ja active Active
- 2009-04-17 EP EP09757354.7A patent/EP2307428B1/de active Active
- 2009-04-17 WO PCT/EP2009/054587 patent/WO2009146971A1/de not_active Ceased
- 2009-04-17 US US12/995,852 patent/US8426628B2/en active Active
- 2009-04-17 ES ES09757354T patent/ES2427767T3/es active Active
- 2009-04-17 KR KR1020107027077A patent/KR101589326B1/ko not_active Expired - Fee Related
- 2009-06-02 CN CN200910141347.7A patent/CN101597302B/zh active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10140563A1 (de) | 2001-08-18 | 2003-02-27 | Degussa | Verfahren zur Herstellung von aminofunktionellen Organosilanen |
Non-Patent Citations (1)
| Title |
|---|
| DS 1189 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102015225879A1 (de) | 2015-12-18 | 2017-06-22 | Evonik Degussa Gmbh | Tris-(alkylalkoxysilyl)amin-reiche Zusammensetzungen, deren Herstellung und deren Verwendung |
| DE102015225883A1 (de) | 2015-12-18 | 2017-06-22 | Evonik Degussa Gmbh | Bis(alkylalkoxysilyl)amin-reiche Zusammensetzungen, ein Verfahren zur deren Herstellung und deren Verwendung |
| DE102016215260A1 (de) | 2016-08-16 | 2018-02-22 | Evonik Degussa Gmbh | Verwendung einer (Alkylalkoxysily)amin-, Bis-(alkylalkoxysilyl)amin und/oder Tris-(alkylalkoxysilyl)amin-enthaltenden Zusammensetzung |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2307428B1 (de) | 2013-07-10 |
| ES2427767T3 (es) | 2013-10-31 |
| US20110118496A1 (en) | 2011-05-19 |
| CN101597302A (zh) | 2009-12-09 |
| EP2307428A1 (de) | 2011-04-13 |
| KR101589326B1 (ko) | 2016-01-28 |
| CN101597302B (zh) | 2014-07-30 |
| JP5345682B2 (ja) | 2013-11-20 |
| US8426628B2 (en) | 2013-04-23 |
| WO2009146971A1 (de) | 2009-12-10 |
| KR20110014175A (ko) | 2011-02-10 |
| JP2011521988A (ja) | 2011-07-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE102008002182A1 (de) | Verfahren zur Herstellung von Alkylaminoalkylalkoxysilanen | |
| EP0702017B1 (de) | Verfahren zur Herstellung von chloridarmen bzw. chloridfreien aminofunktionellen Organosilanen | |
| EP2291385B1 (de) | Verfahren zur wässrigen aufarbeitung eines ammoniumhalogenide und/oder organische aminhydrohalogenide enthaltenden aminofunktionellen organosilans | |
| EP0741137B1 (de) | Verfahren zur Herstellung von chlorfunktionellen Organosilanen armen bzw. freien aminofunktionellen Organosilanen | |
| EP2285813B1 (de) | Verfahren zur aufarbeitung salzhaltiger rückstände aus der herstellung von aminofunktionellen organosilanen | |
| WO2010086254A1 (de) | Verfahren zur herstellung von bis- und tris(silylorgano)aminen | |
| EP2176273B1 (de) | Verfahren zur herstellung von aminoorganosilanen | |
| DE874311C (de) | Verfahren zur Herstellung von Organosilanen | |
| EP1541540B1 (de) | Verfahren zur Herstellung alkoxidreiner Magnesiumalkoxide | |
| DE10353063A1 (de) | Verfahren zur Herstellung von Amino-Gruppen tragenden Siliciumverbindungen | |
| DE102009026755A1 (de) | Verfahren zur Herstellung von Aminoorganosilanen | |
| EP1295889B1 (de) | Verfahren zur Herstellung von Aminoalkylsilanen | |
| EP3046925B1 (de) | Verfahren zur herstellung von carbamatoorganosilanen | |
| EP1831233B1 (de) | Verfahren zur kontinuierlichen herstellung von amino-gruppen tragenden silicium-verbindungen | |
| EP3750877A1 (de) | Verfahren zur herstellung von triacetonamin und 2,2,4,6-tetramethylpiperidin | |
| EP0845470A2 (de) | Verfahren zur kontinuierlichen Herstellung von Carbonoyloxysilanen | |
| DE2807230C3 (de) | Verfahren zur Herstellung von Alkoxymethylsilazanen | |
| DE602004002117T2 (de) | Verfahren zur Herstellung eines Alkoxysilans | |
| DE874313C (de) | Verfahren zur Herstellung von Tetrahydropyranderivaten | |
| DE69813388T2 (de) | Verfahren zur Herstellung von 2,4-Oxazolidindion | |
| DE10023003C1 (de) | Verfahren zur Herstellung von Silicium-bzw. Germanium-substituierten Aminen | |
| DE19941283A1 (de) | Verfahren zur Herstellung von chloridarmen oder chloridfreien Alkoxysilanen | |
| DE102012212050A1 (de) | Verfahren zur Herstellung von Allylsilanen | |
| WO2018033199A1 (de) | Verfahren zur herstellung von sekundären aminoorganosiliciumverbindungen | |
| DE19513976A1 (de) | Verfahren zur Herstellung von chloridarmen bzw. chloridfreien aminofunktionellen Organosilanen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |