WO2005056565A1 - Procede pour preparer des organosilanes d'isocyanate - Google Patents
Procede pour preparer des organosilanes d'isocyanate Download PDFInfo
- Publication number
- WO2005056565A1 WO2005056565A1 PCT/EP2004/013725 EP2004013725W WO2005056565A1 WO 2005056565 A1 WO2005056565 A1 WO 2005056565A1 EP 2004013725 W EP2004013725 W EP 2004013725W WO 2005056565 A1 WO2005056565 A1 WO 2005056565A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- thermolysis
- heating
- evaporation
- reactor
- carbamatoorganosilanes
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 58
- -1 isocyanate organosilanes Chemical class 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 239000012948 isocyanate Substances 0.000 title abstract description 3
- 238000001149 thermolysis Methods 0.000 claims abstract description 29
- 238000001704 evaporation Methods 0.000 claims description 32
- 230000008569 process Effects 0.000 claims description 32
- 238000010438 heat treatment Methods 0.000 claims description 31
- 230000008020 evaporation Effects 0.000 claims description 30
- 239000007789 gas Substances 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000007791 liquid phase Substances 0.000 claims description 7
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000012808 vapor phase Substances 0.000 claims description 4
- 239000007792 gaseous phase Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- 239000000395 magnesium oxide Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 239000000956 alloy Substances 0.000 description 6
- 229910045601 alloy Inorganic materials 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 238000010791 quenching Methods 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000012159 carrier gas Substances 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229910052750 molybdenum Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 229910052721 tungsten Inorganic materials 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 229910052878 cordierite Inorganic materials 0.000 description 3
- JSKIRARMQDRGJZ-UHFFFAOYSA-N dimagnesium dioxido-bis[(1-oxido-3-oxo-2,4,6,8,9-pentaoxa-1,3-disila-5,7-dialuminabicyclo[3.3.1]nonan-7-yl)oxy]silane Chemical compound [Mg++].[Mg++].[O-][Si]([O-])(O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2)O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2 JSKIRARMQDRGJZ-UHFFFAOYSA-N 0.000 description 3
- 229910052747 lanthanoid Inorganic materials 0.000 description 3
- 150000002602 lanthanoids Chemical class 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052593 corundum Inorganic materials 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical compound [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 229910052756 noble gas Inorganic materials 0.000 description 2
- 150000002835 noble gases Chemical class 0.000 description 2
- 239000011225 non-oxide ceramic Substances 0.000 description 2
- 229910052575 non-oxide ceramic Inorganic materials 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 229910052706 scandium Inorganic materials 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 229910001845 yogo sapphire Inorganic materials 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- PCWGTDULNUVNBN-UHFFFAOYSA-N 4-methylpentan-1-ol Chemical compound CC(C)CCCO PCWGTDULNUVNBN-UHFFFAOYSA-N 0.000 description 1
- QYEXBYZXHDUPRC-UHFFFAOYSA-N B#[Ti]#B Chemical compound B#[Ti]#B QYEXBYZXHDUPRC-UHFFFAOYSA-N 0.000 description 1
- 229910052580 B4C Inorganic materials 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000012494 Quartz wool Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910001069 Ti alloy Inorganic materials 0.000 description 1
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 229910001093 Zr alloy Inorganic materials 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- CAVCGVPGBKGDTG-UHFFFAOYSA-N alumanylidynemethyl(alumanylidynemethylalumanylidenemethylidene)alumane Chemical compound [Al]#C[Al]=C=[Al]C#[Al] CAVCGVPGBKGDTG-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- INAHAJYZKVIDIZ-UHFFFAOYSA-N boron carbide Chemical compound B12B3B4C32B41 INAHAJYZKVIDIZ-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011819 refractory material Substances 0.000 description 1
- 238000009419 refurbishment Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910021332 silicide Inorganic materials 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-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
- 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
Definitions
- the invention relates to a method for producing isocyanato-organosilanes by means of one or more microstructured apparatus (microstructured apparatus).
- carbamatoorganosilanes are converted into the isocyanates in inert hot media with the elimination of alcohol.
- this process can only be operated semi-continuously, since the concentration of impurities in the medium increases after a short time in such a way that the desired purity of the product can no longer be guaranteed.
- carbamatoorganosilanes are evaporated in vacuo and the isocyanatosilane formed is distilled off continuously.
- EP 649850 B1 discloses the thermal cleavage (thermolysis) of carbamatoorganosilanes in the gas phase under normal or reduced pressure. The yields obtainable by this process, in particular
- the object was achieved by a process for the preparation of isocyanato-organosilanes by thermolysis of carbamato-organosilanes in the vapor phase, the carbamato-organosilanes being previously heated and / or evaporated in one or more microstructure apparatuses arranged one behind the other. If carbamatoorganosilanes are exposed to long-term thermal stress at high concentrations in the liquid phase, as is the case when heating and evaporating in conventional apparatus such as boiler evaporators, tube bundle heat exchangers, tube bundle circulation evaporators,
- the decomposition reactions not only reduce the possible yield of the desired isocyanatosilanes, but also lead to the equipment being moved after a short time due to deposits with high maintenance and repair costs. Furthermore, the unintended decomposition reactions pose a safety risk, since the decomposition reactions can accelerate due to the release of heat to such an extent that a thermal explosion of the feed material can occur in large, conventional apparatus. Due to the shorter dwell time, less overheating, smaller hold-up volume and large surface / volume ratio, the process according to the invention can be carried out in
- the invention relates to a process for the preparation of isocyanato-organosilanes by thermolysis of
- R for a monovalent and R 3 - are a divalent C ⁇ -Cg hydrocarbon radical and
- R2, R 3 and R ⁇ are each independently selected from the group consisting of methyl, ethyl, n-propyl, i-propyl methoxy, ethoxy, n-propoxy or i-propoxy,
- the process according to the invention offers significant advantages over the processes known from the prior art.
- alcohols - in particular C 1 -C 10 alcohols - of the general formula ROH in particular methanol, ethanol, propanol, butanol, isobutanol, pentanol, are split off from the carbamato-organosilanes - in particular those of the general formula (2) - by thermolysis in general hexanol, Isohexanol, cyclohexanol and 2-ethylhexanol.
- Methanol and ethanol are preferably split off, particularly preferably methanol.
- isocyanatoorganosilanes containing short-chain spacers between the organosilyl group and the isocyanate function can generally be prepared only with difficulty and in moderate yields, in particular those isocyanatoorganosilanes of the general formula (1) in which R 1 is methylene.
- Linear or branched saturated or unsaturated C 1 -C 6 -hydrocarbon groups can generally be used as the spacer R between the organosilyl group and the carbamato group.
- Preferred spacers R 1 are alkyl radicals, in particular linear alkyl radicals, methylene, ethylene and propylene are particularly preferably used.
- R 2 , R 3 and R ⁇ are preferably selected independently from the group containing methyl, methoxy, ethoxy, n-propoxy or i-propoxy radicals, in particular from methyl, methoxy or ethoxy.
- Microstructure apparatuses for heating, evaporation and cooling of the carbamatoorganosilane or the reaction products are known to the person skilled in the art, for example from “Microreactors", W. Ehrfeld, V. Hessel, H. Löwe, VCH-Wiley, (2001).
- Preferred embodiments of microstructure apparatus for the process according to the invention have a surface / volume ratio between 500 and 50,000 m 2 / m 3 , in particular from 5,000 to 40,000 m 2 / m 3, very particularly from 10,000 to 30,000 m 2 / m 3 .
- the hydrodynamic residence time of liquid phases is typically in the process according to the invention.
- Carbamatorganosilane in the microstructure devices 0.01 to 10 seconds, in particular 0.05 to 5, very particularly 0.25 to 2.5 seconds.
- Carbamatorganosilane in the microstructure apparatus is typically 0, l * 10 A -3 to 0.1 seconds, in particular 0, ⁇ * 10 - 3 to 0.05, especially 2.5 * 10 ⁇ -3 to 0.025 seconds.
- Carbamatoorganosilanes - in particular one of the general formula (2) - is preferably carried out in a temperature range from 150 to 1000 ° C, particularly preferably between 300 to 600 ° C, in particular in a range from 400 to 500 ° C in a pressure range from 0.01 to 1000 bar, preferably from 0.1 to 100 bar, particularly preferably from 1 to 40 bar.
- the carbamatoorganosilane is heated and / or evaporated in a microstructure device or a sequence of microstructure devices.
- the hydrodynamic residence time in the microstructure apparatus is generally chosen such that a residence time of less than 10 seconds is calculated for the liquid phase and a residence time of less than 0.1 seconds is calculated for the gas phase.
- the carbamate vapor obtained is then passed into a reactor in which the conversion (thermolysis) to the isocyanato-organosilane takes place.
- the carbamatorganosilanes can be heated in a microstructure apparatus in a first step, followed by evaporation in an evaporator.
- the heating and the evaporation can take place in a single microstructure apparatus.
- the carbamatorganosilane is heated in a first microstructure apparatus and then evaporated in a downstream second microstructure apparatus.
- the evaporation and / or the thermolysis takes place at different temperatures and / or pressures than the heating. In a further possible embodiment, the thermolysis takes place at different temperatures and / or pressures than the evaporation and / or heating.
- Heating and evaporation different temperatures and pressures can be selected.
- the steps of heating, evaporation and thermolysis increase the temperature at an almost constant (normal) pressure, so that, for example, heating to 150 ° C at 1.5 bar, evaporation at 250 ° C and 1, 1 bar and the thermolysis at 500 ° C and 1 bar.
- the steps of heating, evaporation and thermolysis are used to maintain the temperature while simultaneously reducing the pressure, so that, for example, heating to 400 ° C. at 40 bar, evaporation at 400 ° C. and 10 bar and thermolysis 400 ° C and 1 bar.
- the steps of heating, evaporation and thermolysis result in a drop in pressure and in temperature, so that, for example, heating to 450 ° C at 40 bar, evaporation at 400 ° C and 10 bar and thermolysis at 350 ° C and 1 bar.
- the evaporation takes place at a minimum temperature followed by the thermolysis, so that, for example, the heating up 400 ° C at 40 bar, evaporation at 250 ° C and 1.1 bar and thermolysis at 500 ° C and 1 bar.
- the evaporation takes place at a maximum temperature followed by the thermolysis, so that, for example, the heating to 200 ° C. at 4 bar, the evaporation at 400 ° C. and 10 bar and the thermolysis at 350 ° C and 1 bar.
- the carbamatoorganosilane is heated to 150 ° C. to 600 ° C., a pressure: from 0.1 to 1000 bar being selected.
- the carbamatoorganosilane is evaporated at 150 ° C to 600 ° C, a pressure of 0.1 to 100 bar being selected.
- the conversion of the carbamatorganosilane vapor to the isocyanatoorganosilane takes place at a reactor temperature of 150 ° C. to 1000 ° C. and a pressure of 0.1 to 100 bar.
- the carbamatorganosilane vapor - in particular such carbamatorganosilanes of the general formula (2) - is passed into a gas phase reactor and thermolytically split to isocyanato-organosilanes - in particular those of the general formula (1) - and an alcohol (ROH).
- ROH an alcohol
- the reactor for converting the carbamatoorganosilane in the vapor phase can be provided with internals, inert packing or a heterogeneous catalyst or a combination of two or more of the aforementioned features. Suitable are all relevant known reactors for performing gas phase reactions. In a preferred embodiment of the method according to the invention, tube reactors or tube bundle reactors are used. The internals influence the flow, temperature and microwave distribution in the reaction space.
- thermolysis the process according to the invention can be carried out in the presence of one or more heterogeneous catalysts.
- Preferred heterogeneous catalysts are oxides, hydroxides, hydroxide oxides, mixed oxides, acetates, formates, oxalates, tartrates, citrates, nitrates, carbonates or mixtures of the abovementioned compounds one or more elements selected from the group comprising Sn (I), Sn (II) , Pb (II), Zn (II), Cu (I), Cu (II), C ⁇ (I), Co (II), Na, K, Li, Rb, Cs, Sr, Ba, Mg, Ca, Cr , Mo, Ti, V, W, Ce, Fe, Ni, Si, AI, Ge, Ga, In, Sc, Y, La, Lanthanide, Pd, Pt, Rh, Cu, Ag, Au and Cd.
- Heterogeneous catalysts containing one or more compounds selected from the group are particularly suitable containing Ti0 2 , Zr0 2 , Hf0 2 , Al 2 0 3 , BaO, CaO, MgO, Ce0 2 , La 2 0 3 ,
- Aluminosilicates especially zeolite in different pore sizes, cordierite of the composition
- heteropolyacids e.g. B. graphite, transition metal nitrides, borides, silicides and carbides.
- heterogeneous catalysts in the form of metals, alloys, compounds or mixtures of metals and / or compounds are preferably applied to support materials.
- Particularly suitable carriers are glass wool, quartz wool, oxidic materials such as SiO 2 , Al 2 O 3 , steatite, silicates or oxidic or non-oxidic ceramics such as silicon carbide, silicon nitride, boron nitride, boron carbide, carbon, titanium boride, titanium nitride, titanium carbide, aluminum carbide or metals resistant under the reaction conditions or alloys such as iron, nickel, titanium, zircon, steels in particular stainless steel with the alloy components Cr, Ni, Mo, Al, Ti, Si, V, Nb, W, Cu.
- Preferred carriers made of inert refractory materials are oxidic or non-oxide ceramics, Si0 2 , carbon, aluminosilicates, magnesium-aluminosilicates or resistant metallic materials.
- the catalyst supports can be used in the form of irregular beds of granules, spheres, rings, half rings, saddles, cylinders, trilobs, pills or structured packings or monoliths. Bodies in the form of
- small monoliths on the outside inside usual are dimensions such as 1 "5-20 cm, d «1-5 cm
- trilobs or pills can be used.
- Catalyst supports and catalysts in the form of monoliths or structured packings with straight-channel structures, mixer structures or irregular foam structures are particularly preferred.
- the invention it is advantageous to cool the vaporous reaction products leaving the reactor very quickly, in particular to temperatures between 20.degree. C. and 200.degree. C., in order to prevent back-reaction of the isocyanato-organosilane produced with the alcohol produced back to the carbamato-organosilane.
- Usual methods of rapid cooling such as cold gas injection with inert gases, direct quench cooling with liquid reactants or heat transfer media are suitable for this.
- indirect quench cooling of the reaction gas in one or more microstructured heat exchangers is considered
- the microstructured heat exchanger is connected downstream of the thermolysis reactor. Ideally, microstructured heat exchangers with a surface / volume ratio of 500 to 50,000 m 2 / m 3 are used, in particular 5,000 to 40,000 m 2 / m 3, very particularly 10,000 to 30,000 m 2 / m 3 .
- the gas phase residence times in the microstructured heat exchangers are generally selected such that they are calculated for gaseous phases under 0.1 seconds, in particular between 0.1 * 10 ⁇ -3 and 0.1 seconds, particularly preferably at 0.5 * 10 ⁇ -3 to 0.05, especially 2.5 * 10 ⁇ -3 to 0.025 seconds.
- the liquid residence times in the microstructured heat exchangers are generally selected so that they calculate for liquid phases under 10 seconds, in particular between 0.01 to 10 seconds, particularly preferably 0.05 to 5, very particularly 0.25 to 2.5 seconds lies. In this way, a very effective prevention of the back reaction of alcohol and isocyanatoorganosilane to the carbamatoorganosilane can be achieved.
- materials are selected which are resistant to the starting materials under the reaction conditions.
- Materials such as glass, quartz glass, graphite, ceramics, non-oxide ceramics or metals and alloys are particularly suitable, particularly selected from the group comprising aluminum oxide, silicon carbide, silicon nitride, boron nitride, stainless steel, nickel and nickel-based alloys, titanium and titanium alloys, zirconium and zirconium alloys and tantalum ,
- a carrier gas can optionally be used.
- Suitable carrier gases can be selected from the group containing nitrogen, hydrogen, air, noble gases, in particular helium or argon, vapors of carbon-containing substances, in particular carbon monoxide, carbon dioxide, methane, octane, toluene, decalin, tetralin or mixtures of the aforementioned gases.
- the process according to the invention can generally be carried out in batch mode (batchwise), semi-continuously or continuously, a continuous process being particularly preferred.
- the reaction mixture can be separated after cooling by customary separation processes known to those skilled in the art. In one possible embodiment of the workup, this is
- the desired product can then be obtained in pure form, for example, in a downstream column at the top.
- a high boiler / starting material mixture is obtained, from which, in particular, the starting material can be recovered and, if necessary after previous work-up, in particular by distillation, can be returned to the process, preferably to the process inlet.
- the process according to the invention has the great advantage over the processes known from the prior art that the desired products can be obtained in high purity (> 97%) in a simple distillation step.
- the formation of high thermal loads observed six-membered isocyanurates is practically completely avoided by the present process.
- FIGS. 1, 2 and 3a to 3c in combination with a possible product treatment according to FIG. 4, represent possible embodiments and devices for carrying out the method according to the invention, are intended to serve for a more detailed explanation and are in no way to be regarded as a restriction.
- Figure 1 shows a possible embodiment of the method according to the invention with heating and evaporation in one apparatus and heating / evaporation and reaction at different temperatures and pressures:
- the carbamato-organosilane (A) is pumped into the microstructured heat exchanger / evaporator (2) by means of the pump (1) and heated and evaporated there.
- a carrier gas stream (F) can optionally be added to the educt stream at one or more points (indicated by the broken lines).
- the carbamatoorganosilane vapor is expanded to the reactor pressure via the valve (3).
- the carbamatoorganosilane vapor is converted to isocyanatoorganosilane and alcohol.
- the outflow from the reactor is cooled in the microstructured quench cooler (5) and the stream (G) is fed to the product workup (according to FIG. 4).
- FIG. 2 shows a possible embodiment of the method according to the invention with heating and evaporation in separate microstructure devices and heating / evaporation and reaction (thermolysis) at different temperatures and pressures.
- the carbamatoorganosilane (A) is pumped into the microstructured heat exchanger (2) via the pump (1) and heated there.
- the liquid passes through the valve (3) Carbamatoorganosilane in the microstructured evaporator (2a).
- the carbamatoorganosilane vapor is expanded isothermally to the reactor pressure via the valve (3a) and the microstructured heat exchanger (2b).
- the carbamatoorganosilane vapor becomes isocyanatoorganosilane. and alcohol implemented.
- the outflow from the reactor is cooled in the microstructured quench cooler (5) and fed to the product workup (via (G), then according to FIG. 4).
- a carrier gas stream (F) can optionally be added to the educt stream at one or more points (indicated by the broken lines).
- educt (carbamatoorganosilane) recovered from the workup according to FIG. 4 can be fed to stream (A) via (H).
- FIGS. 3a to 3c show a possible embodiment of the method according to the invention with heating and evaporation at different temperatures and pressures and reaction (thermolysis) at different temperatures and pressures.
- the possible embodiments according to FIGS. 3a, 3b and 3c differ in the different design of the return of streams from the evaporator (8) by means of a pump (9):
- FIG. 3a the return from the evaporator (8) to the beginning of the system follows 3b, the return takes place behind the pump (1) and upstream of the evaporator (2), and in FIG. 3c the feed and return streams are combined behind the pump (1) and upstream of the pump (9) and passed together to the evaporator (2) ,
- the carbamatoorganosilane (A) in the microstructured ones is pumped (1) and optionally pumped (9)
- the liquid carbamatoorganosilane is fed into the evaporator (8) via the valve (3). relaxed with part evaporating.
- the evaporated portion is expanded to the reactor pressure via the valve (3a).
- the portion remaining in the liquid state in the evaporator (8) is pumped back to the inlet via the pump (9), mixed with fresh (A) or (H) carbamatoorganosilane obtained from the recovery according to FIG. 4 and fed again to the microstructured heater (2) ,
- the carbamatoorganosilane vapor is converted to isocyanatoorganosilane and alcohol.
- the effluent from the reactor is cooled in the microstructured quench cooler (5) and the
- FIG. 4 generally shows an embodiment and device for the product refurbishment of the method according to the invention, which can be connected to all embodiments according to FIGS. 1, 2, 3a, 3b or 3c, where (G) and (H) represent the interfaces to the other figures :
- the stream (G) containing the crude product is in a stripping column (6) overhead of low boilers and gases (B), in particular the alcohol split off during thermolysis, by feeding a
- Stripping gas (E) exempted.
- a stream freed from the low boilers is passed into a downstream column (7), the pure isocyanato-organosilane (C) being obtained overhead and a high-boiler mixture containing unconverted product via the bottom
- Carbamatoorganosilan (D) is separated. This can be partially or completely returned, optionally after a further chemical or physical treatment or workup via (10) to the start of the system (H).
- Suitable stripping gases (E) are selected from the group comprising nitrogen, noble gases, carbon dioxide and low-boiling Hydrocarbons such as methane, ethane, propane, butane, pentane etc. or mixtures with other substances which are gaseous under the stripping conditions and which contain one or more of these components in proportions above 50%.
- methylcarbamatopropyltrimethoxysilane were heated and evaporated in an electrically heated boiling flask within 2 h.
- the steam was passed into an electrically heated tubular reactor filled with catalyst and having an inner diameter of 25 mm and converted to ⁇ -isocyanatopropyltrimethoxysilane.
- the gas mixture leaving the tubular reactor was cooled in a Liebig cooler made of glass (length 200 mm).
- the temperature of the tubular reactor was 450 ° C, at a pressure of 1 * 10 A 5 Pa at the system outlet, after the cooler.
- the tubular reactor was filled with a catalyst consisting of a straight-channel cordierite monolith (2 MgO * 2 Al2O3 * 5 SiO 2) coated with magnesium oxide.
- Methyl carbamatopropyltrimethoxysilane heated and evaporated at a rate of 16 ml / min in an electrically heated microstructure.
- the vapor leaving the microstructure was in passed an electrically heated tubular reactor filled with catalyst and having an inner diameter of 25 mm and converted to ⁇ - isocyanatopropyltrimethoxysilane.
- the gas mixture leaving the tubular reactor was cooled to 25 ° C. in a further microstructure.
- the residence time for the liquid phase in the microstructure for heating and evaporation was approx. 2 seconds, in the micro structure for cooling approx. 1 second.
- the microstructures have a surface / volume ratio of 20,000 m "1.
- the temperature of the tube reactor was 450 ° C., at a pressure of 1 * 10 5 Pa at the system outlet, after the microstructure cooler.
- the tube reactor was equipped with a catalyst consisting of a filled with magnesium oxide-coated, straight-channel cordierite monoliths (2 MgO * 2 Al2O3 * 5 SiO 2) Starting from 4.2 mol of methyl carbamatopropyltrimethoxysilane, 3.35 mol of ⁇ -isocyanatopropyltrimethoxysilane and 0.8 mol of unreacted methylcarbamatopropanetrimethoxysilane were found in the condensate after the cooler corresponds to a ⁇ -isocyanatopropyltrimethoxysilane yield of 80% with respect to the methylcarbamatopropyltrimethoxysilane used.
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Abstract
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DE2003158063 DE10358063A1 (de) | 2003-12-11 | 2003-12-11 | Verfahren zur Herstellung von Isocyanatoorganosilanen |
DE10358063.8 | 2003-12-11 |
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WO2005056565A1 true WO2005056565A1 (fr) | 2005-06-23 |
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PCT/EP2004/013725 WO2005056565A1 (fr) | 2003-12-11 | 2004-12-02 | Procede pour preparer des organosilanes d'isocyanate |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102007006147A1 (de) | 2007-02-07 | 2008-08-14 | Wacker Chemie Ag | Verfahren zur Herstellung von Isocyanatoorganosilanen |
CN109503647A (zh) * | 2017-09-15 | 2019-03-22 | 张家港市国泰华荣化工新材料有限公司 | 3-异氰酸酯基丙基三甲氧基硅烷的制法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0649850A1 (fr) * | 1993-10-20 | 1995-04-26 | OSi Specialties, Inc. | Procédé de préparation d'isocyanatoorganosilanes |
EP1319890A2 (fr) * | 2001-12-11 | 2003-06-18 | P21-Power for the 21st Century GmbH | Dispositif d'évaporation et de surchauffe d'au moins un milieu et système de pile à combustible |
-
2003
- 2003-12-11 DE DE2003158063 patent/DE10358063A1/de not_active Withdrawn
-
2004
- 2004-12-02 WO PCT/EP2004/013725 patent/WO2005056565A1/fr active Application Filing
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0649850A1 (fr) * | 1993-10-20 | 1995-04-26 | OSi Specialties, Inc. | Procédé de préparation d'isocyanatoorganosilanes |
EP1319890A2 (fr) * | 2001-12-11 | 2003-06-18 | P21-Power for the 21st Century GmbH | Dispositif d'évaporation et de surchauffe d'au moins un milieu et système de pile à combustible |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102007006147A1 (de) | 2007-02-07 | 2008-08-14 | Wacker Chemie Ag | Verfahren zur Herstellung von Isocyanatoorganosilanen |
US8288578B2 (en) | 2007-02-07 | 2012-10-16 | Wacker Chemie Ag | Process for preparing isocyanatoorganosilanes |
CN109503647A (zh) * | 2017-09-15 | 2019-03-22 | 张家港市国泰华荣化工新材料有限公司 | 3-异氰酸酯基丙基三甲氧基硅烷的制法 |
CN109503647B (zh) * | 2017-09-15 | 2021-09-21 | 张家港市国泰华荣化工新材料有限公司 | 3-异氰酸酯基丙基三甲氧基硅烷的制法 |
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