CN105964304A - Method for catalytic synthesis of gamma-propyl chloride trichlorosilane and catalyst thereof - Google Patents
Method for catalytic synthesis of gamma-propyl chloride trichlorosilane and catalyst thereof Download PDFInfo
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- CN105964304A CN105964304A CN201610565708.0A CN201610565708A CN105964304A CN 105964304 A CN105964304 A CN 105964304A CN 201610565708 A CN201610565708 A CN 201610565708A CN 105964304 A CN105964304 A CN 105964304A
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- Prior art keywords
- catalyst
- silane
- synthesizing
- catalyzing
- polyacetylene
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- 239000003054 catalyst Substances 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 15
- 239000005052 trichlorosilane Substances 0.000 title claims abstract description 13
- 238000007036 catalytic synthesis reaction Methods 0.000 title abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 68
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 58
- 229920001197 polyacetylene Polymers 0.000 claims abstract description 56
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 33
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 claims abstract description 13
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 7
- OOXSLJBUMMHDKW-UHFFFAOYSA-N trichloro(3-chloropropyl)silane Chemical compound ClCCC[Si](Cl)(Cl)Cl OOXSLJBUMMHDKW-UHFFFAOYSA-N 0.000 claims description 39
- 230000002194 synthesizing effect Effects 0.000 claims description 27
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 239000011591 potassium Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 230000004044 response Effects 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000010668 complexation reaction Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000007259 addition reaction Methods 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000003446 ligand Substances 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000001556 precipitation Methods 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- 229920002521 macromolecule Polymers 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 4
- 230000000740 bleeding effect Effects 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- -1 γ-chloropropyl Chemical group 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 description 1
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- 229910003251 Na K Inorganic materials 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ODOPKAJVFRHHGM-UHFFFAOYSA-N phenyltin Chemical compound [Sn]C1=CC=CC=C1 ODOPKAJVFRHHGM-UHFFFAOYSA-N 0.000 description 1
- 229920002627 poly(phosphazenes) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2217—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
- B01J31/182—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine comprising aliphatic or saturated rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/226—Sulfur, e.g. thiocarbamates
-
- 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
- C07F7/12—Organo silicon halides
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/122—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving the formation of Si-C linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0213—Complexes without C-metal linkages
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/828—Platinum
-
- 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
- Y02P20/584—Recycling of catalysts
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- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
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- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
The invention discloses a method for catalytic synthesis of gamma-propyl chloride trichlorosilane and a catalyst thereof. The catalyst is a platinum complex of polyacetylene loaded nitrogen heterocyclic ring as shown in formula (I); the gamma-propyl chloride trichlorosilane is prepared by implementing hydrosilylation on chloropropene and trichlorosilane in the presence of the catalyst. Compared with the prior art, the method adopts polyacetylene as a carrier, heterocyclic ring ligand and platinum coordination of lone pair electrons are adopted, the structure of the catalyst is changed due to introduction of heterocyclic rings, the reaction velocity and the yield of the synthesized gamma-propyl chloride trichlorosilane are greatly increased, and the reaction temperature is reduced; moreover, as the catalyst can be recycled and reused, the production cost of the gamma-propyl chloride trichlorosilane is lowered.
Description
Technical field
The invention belongs to organic chemical synthesis technical field, relate to the method for a kind of γ of catalyzing and synthesizing-chloropropyl trichloro-silane and urge
Agent.
Background technology
γ-chloropropyl trichloro-silane is monomer most basic in silane coupler, is the main life of synthesizing silane coupler series of products
Produce raw material, as γ-r-chloropropyl trimethoxyl silane, γ-chloropropyl triethoxysilane, gamma-aminopropyl-triethoxy-silane, double-(γ-
The silica-based propyl group of triethoxy) tetrasulfide etc., it is widely used in producing pesticide and medicine intermediate, rubber, coating, Shui Chu
Reason, textile auxiliary and auxiliary agent performance-relevant with its chemical constitution, development prospect is wide.
At present, scientific worker, with chloropropene and trichlorosilane as raw material, utilizes transient metal complex, especially platinum complex
Catalyzing addition reaction of silicon with hydrogen synthesis γ-chloropropyl trichloro-silane this respect has done a lot of research.But, reaction rate, reaction yield
Still have much room for improvement；And, reaction temperature is high, and catalyst amount is big and can not reclaim, and production cost is too high.
Summary of the invention
The technical problem to be solved is to provide one to catalyze and synthesize γ-chloropropyl three for above-mentioned the deficiencies in the prior art
The method of chlorosilane and catalyst thereof, this good catalyst activity, consumption is few, and can recycle；Reduce catalyze and synthesize γ-
Chloropropyl trichloro-silane reaction temperature, shorten the response time and reduce production cost.
The present invention solves technical problem set forth above, the technical scheme used is:
A kind of catalyst for catalyzing and synthesizing γ-chloropropyl trichloro-silane, its structure is born for the polyacetylene as shown in formula (I)
Carry nitrogenous heterocyclic platinum complex:
Wherein, n is the integer more than zero, and R-Pt is nitrogenous heterocyclic platinum complex group, and R is nitrogen heterocyclic ring group, its with
The connection site of left side alkyl chain is atom N；Hetero atom in described nitrogen heterocyclic ring group is in N, O, S atom
Kind or several, when when hetero atom number is x, x less than 6, m=6-x, x are more than or equal to 6, m is 0.Owing to relating to electric charge
Balance and the problem of coordination balance, nitrogen heterocyclic ring periphery there is also potassium ion.
Preferably, in described nitrogenous heterocyclic platinum complex group R-Pt, hetero atom number x is less than 6, is selected from such as formula
Structure shown in 1a～formula 1k, in one or more:
The preparation method of the above-mentioned catalyst for catalyzing and synthesizing γ-chloropropyl trichloro-silane is: use side chain to be connected with nitrogenous heterocyclic
Disubstituted polyacetylene carries out complexation reaction with the Pt in potassium chloroplatinite, obtains structure polyacetylene load as shown in formula (I) and contains
The platinum complex of azacyclo-, is the catalyst for catalyzing and synthesizing γ-chloropropyl trichloro-silane；
Wherein, side chain is connected with shown in nitrogenous heterocyclic disubstituted polyacetylene structure such as formula (II):
Wherein, R is nitrogen heterocyclic ring group, and it is atom N with the connection site of position, side alkyl chain；Described nitrogen heterocyclic ring group
In hetero atom be one or more in N, O, S atom.
By such scheme, described side chain is connected with nitrogen heterocyclic ring and the mol ratio of potassium chloroplatinite in nitrogenous heterocyclic disubstituted polyacetylene
For 1:2～1:1.
By such scheme, the temperature of described complexation reaction is 60～80 DEG C, and the solvent used is acetone, it is also possible to be and water
The solvent dissolved each other, if oxolane, DMF, acetonitrile, dimethyl sulfoxide etc. are miscible with water organic molten
Agent.
By such scheme, described side chain is connected with the preparation method of nitrogenous heterocyclic disubstituted polyacetylene: polyacetylene macromolecule is with nitrogenous
There is substitution reaction in heterocycle n, obtains side chain and be connected with nitrogenous heterocyclic disubstituted polyacetylene.Wherein, miscellaneous in described nitrogen heterocyclic ring
Atom is one or more in N, O, S atom, but the N position that the connection site of its substitution reaction is in nitrogen heterocyclic ring.
The present invention uses the method for above-mentioned catalyst synthesis γ-chloropropyl trichloro-silane, mainly comprises the following steps: chloropropene and catalysis
Agent mixing post-heating activates, and is subsequently adding trichlorosilane and carries out hydrosilylation, and products therefrom is γ-chloropropyl trichlorine silicon
Alkane；
By such scheme, the temperature of described heat-activated is 40～80 DEG C, and the time is 10～30min.
By such scheme, the temperature of described hydrosilylation is 40～80 DEG C, and the time of reaction is 1～1.5 hour.
By such scheme, described chloropropene is 1:(1 × 10 with catalyst, the mol ratio of trichlorosilane-6～1 × 10-5): 1.
By such scheme, the environment of described hydrosilylation is inert atmosphere, anhydrous condition.
The present invention uses above-mentioned catalyst to synthesize γ-chloropropyl trichloro-silane, after hydrosilylation terminates, by distillation point
From obtaining product, by being centrifugally separating to obtain precipitate, precipitation is filtered, wash repeatedly with methanol, 40～50 DEG C of vacuum drying
After, this catalyst the most recyclable.
Compared with prior art, the invention has the beneficial effects as follows:
1) present invention uses side chain to be connected with nitrogenous heterocyclic disubstituted polyacetylene, utilizes N or O in its nitrogen heterocyclic ring or S former
Son is coordinated with Pt, it is achieved that the load on polyphosphazene polymer acetylene of the heterocycle platinum complex, thus prepares and be used for catalyzing and synthesizing
The catalyst of γ-chloropropyl trichloro-silane.This good catalyst activity, actual amount is few, and can recycle, and reduces γ-chlorine
The preparation cost of propyltrichlorosilan.
2) catalyst in the present invention is coordinated with platinum using polyacetylene macromolecule as carrier, the heterocyclic ligand containing lone pair electrons,
The introducing of heterocycle changes the structure of catalyst, drastically increases reaction rate and the productivity of synthesis γ-chloropropyl trichloro-silane,
And reduce reaction temperature, shorten the response time.
Accompanying drawing explanation
Fig. 1 is the synthetic route chart of catalyst polyacetylene load heterocycle platinum complex P3 in embodiment 1.
Fig. 2 is the nucleus magnetic hydrogen spectrum figure of catalyst polyacetylene load heterocycle platinum complex P3 in embodiment 1.
Detailed description of the invention
In order to be more fully understood that present disclosure, below in conjunction with specific embodiment, present disclosure is described further, but
The protection content of the present invention is not limited to following example.
In the present invention, described side chain is connected with nitrogenous heterocyclic disubstituted polyacetylene, shown in structure such as formula (II), and preparation method,
I.e. by simple substitution reaction, nitrogen heterocyclic ring is incorporated on the side chain of polyacetylene, can be by preparing the monomer of polyacetylene, poly-second
Three steps of alkynes macromolecule, polyacetylene high molecular heterocycle Post functionalization are constituted.These three steps are specific as follows:
1) with anhydrous tetrahydro furan as solvent, phenylacetylene occurs with compound 3 (1-(4-bromine butoxy)-4-iodobenzene)
Sonogashira reacts, and obtains compound 4 (1-(4-bromine butoxy)-4-(phenylene-ethynylene) benzene)；
2) there is additive reaction in compound 4 under the catalytic action of tungsten hexachloride and tetraphenyltin, obtains polyacetylene macromolecule
P1；
3) gained polyacetylene macromolecule P1 and nitrogen heterocyclic ring generation substitution reaction, obtains side chain and is connected with nitrogenous heterocyclic disubstituted poly-
Acetylene.
As it is shown in figure 1, the present invention provides the monomer of a polyacetylene, polyacetylene high molecular concrete synthetic route at this, in detail
Step is as follows:
(1) synthesis of the polyacetylene monomer containing alkyl bromide
Weigh Compound 3 (2.500g), CuI (0.040g), Pd (PPh3)4(0.050g)、PPh3(0.055g) in dry
In Schlenk pipe, it is stoppered saline plug, logical nitrogen 5-6 time of bleeding, in the case of logical nitrogen, continuously add Et3N(4.2
ML), THF (30mL) and phenylacetylene (1.4mL), be stirred at room temperature under the protection of nitrogen one day, reaction terminates rear normal pressure mistake
Filter off except unnecessary salt, be spin-dried for, i.e. obtain the thick product of compound 4.
Thick product as eluent with petroleum ether/chloroform (v/v=10/1), separates through silica gel column chromatography, obtains pure compound 4
(1.800g), productivity is 76.5%.
(2) synthesis of polyacetylene macromolecule P1
1) in glove box, in the case of oxygen content is at below 30ppm, catalyst tungsten hexachloride (34mg) and four is weighed
Phenyltin (34mg), in Schlenk pipe, is stoppered saline plug, takes out, and adds the new toluene (6 steamed in this Schlenk pipe
ML), activate 1 hour at 80 DEG C；
2) simultaneously, Weigh Compound 4 (1.000g) in another Schlenk pipe, bleed logical nitrogen several times after, row
Air in Schlenk pipe to the greatest extent, injects the new toluene (6mL) steamed wherein, activates 1 hour at 80 DEG C；After activation,
The solution of compound 4 is imported in the Schlenk pipe containing catalyst, react 2 days at 75 DEG C；After gained reactant filters,
Solution is threaded to half-dried；
3) this is threaded in the conical flask containing 100mL methanol that half-dried solution is added dropwise to magneton stirring, has green precipitate
Separating out, sucking filtration goes out and wherein precipitates；Again by this precipitation with oxolane dissolve after, be further dropped into magneton stirring containing 100
In the conical flask of mL methanol, again separate out precipitation, sucking filtration；Gained filter cake methanol washs repeatedly, finally collects green solid
Being dried under vacuum to constant weight in 45 DEG C, i.e. obtain polyacetylene macromolecule P1 (810mg), productivity is 81%.
In following embodiment, reagent used is commercially available；The anhydrous THF that solvent for use THF, toluene respectively processed
And dry toluene, processing method is that the backflow of Na-K alloy steams；DMF is the dry DMF processed, processing method be with
CaH2For desiccant, stirring stands then decompression and steams.
In following embodiment, hydrosilylation must strict guarantee reaction vessel and reaction reagent be dry, and reaction is at N2
Carry out under protection.
Embodiment 1
(1) a kind of catalyst for catalyzing and synthesizing γ-chloropropyl trichloro-silane, its structure is the polyacetylene as shown in P3
Loading nitrogenous heterocyclic platinum complex, wherein, n is the integer more than zero.
The above-mentioned catalyst for catalyzing and synthesizing γ-chloropropyl trichloro-silane, i.e. polyacetylene load nitrogen heterocyclic ring as shown in formula P3
The synthetic method of platinum complex, step is as follows:
1) in Fig. 1, side chain as shown in P2 is connected with the synthesis of nitrogenous heterocyclic disubstituted polyacetylene
Weigh polyacetylene macromolecule P1 (80mg), Isosorbide-5-Nitrae, 7,10-tetraazacyclododecanands (63mg), potassium carbonate (51mg), iodine
Changing potassium (20mg) in dry Schlenk pipe, be stoppered saline plug, logical nitrogen 5-6 time of bleeding, in the situation of logical nitrogen
Under, add dry DMF (3mL) and anhydrous THF (3mL), react 3 days in 75 DEG C under nitrogen protection；
After gained product is filtered, in the conical flask of the pure water cold containing 100mL being added dropwise to magneton stirring, have
Orange Precipitation, sucking filtration goes out gained precipitation；Then, after this precipitation is dissolved with oxolane, it is further dropped into magneton stirring
In conical flask containing pure water cold for 100mL, again separating out precipitation, sucking filtration gained filter cake is many with cold pure water washing
Secondary；Finally, collect orange solids and be dried under vacuum to constant weight in 45 DEG C, obtain side chain and be connected with nitrogenous heterocyclic disubstituted polyacetylene
P2 (65mg), productivity is 61%.
2) polyacetylene loads the synthesis of nitrogenous heterocyclic platinum complex P3
Weigh side chain and be connected with disubstituted polyacetylene P2 (50mg) and the chloroplatinous acid of nitrogen heterocyclic ring Cyclen
Potassium (50mg), in dry Schlenk pipe, adds acetone, return stirring 4 days；Gained solid product is filtered out, and
Repeatedly washing with acetone and water, filtering residue is vacuum dried, and i.e. obtains light yellow polyacetylene and loads nitrogenous heterocyclic platinum complex P3,
I.e. for catalyzing and synthesizing the catalyst of γ-chloropropyl trichloro-silane.
(2) method of above-mentioned catalyst synthesis γ-chloropropyl trichloro-silane, specifically comprises the following steps that equipped with reflux condensation mode
The reaction bulb of pipe adds chloropropene (3.8g) and catalyst P3 (0.3mg), at 50 DEG C, activates 20min, be subsequently adding and
The trichlorosilane of chloropropene equimolar amounts, reacts 1 hour, and products therefrom is γ-chloropropyl trichloro-silane, and reaction yield is
81.2%.
During catalyzing and synthesizing γ-chloropropyl trichloro-silane, use gas chromatograph monitoring reaction course, with standard sample and mark
Directrix curve confirms the structure of product and calculates the productivity of Si-H addition reaction thing.
Embodiment 2
(1) a kind of catalyst for catalyzing and synthesizing γ-chloropropyl trichloro-silane, its structure is the polyacetylene as shown in P4
Loading nitrogenous heterocyclic platinum complex, wherein, n is the integer more than zero.
The above-mentioned catalyst for catalyzing and synthesizing γ-chloropropyl trichloro-silane, i.e. polyacetylene load nitrogen heterocyclic ring as shown in formula P4
The synthetic method of platinum complex, step is as follows:
1) side chain is connected with the synthesis of nitrogenous heterocyclic disubstituted polyacetylene
Weigh polyacetylene macromolecule P1 (80mg), azepine-15-crown-5 (80mg), potassium carbonate (51mg), potassium iodide (20mg)
In dry Schlenk pipe, it is stoppered saline plug, logical nitrogen 5-6 time of bleeding, in the case of logical nitrogen, add anhydrous
DMF (3mL) and anhydrous THF (3mL), reacts 3 days in 75 DEG C under nitrogen protection；
After gained product is filtered, in the conical flask of the pure water cold containing 100mL being added dropwise to magneton stirring, have
Orange Precipitation, sucking filtration goes out gained precipitation；Then, after this precipitation is dissolved with oxolane, it is further dropped into magneton stirring
In conical flask containing 100mL methanol, again separating out precipitation, sucking filtration gained filter cake methanol washs repeatedly；Finally, collect
Orange solids is dried under vacuum to constant weight in 45 DEG C, obtains side chain and is connected with nitrogenous heterocyclic disubstituted polyacetylene (82mg), and productivity is
65%.
2) polyacetylene loads the synthesis of nitrogenous heterocyclic platinum complex P4
Weigh side chain and be connected with nitrogenous heterocyclic disubstituted polyacetylene (60mg) with potassium chloroplatinite (50mg) in dry Schlenk
Guan Zhong, adds acetone, return stirring 4 days；Being filtered out by gained solid product, and repeatedly wash with acetone and water, filtering residue is true
Empty be dried, i.e. obtain the platinum complex P4 of light yellow polyacetylene load nitrogen heterocyclic ring azepine-15-crown-5, be i.e. used for catalyzing and synthesizing γ-
The catalyst of chloropropyl trichloro-silane.
(2) method of above-mentioned catalyst synthesis γ-chloropropyl trichloro-silane, specifically comprises the following steps that equipped with reflux condensation mode
The reaction bulb of pipe adds chloropropene (3.8g) and catalyst P4 (0.4mg), at 60 DEG C, activates 30min, be subsequently adding and
The trichlorosilane of chloropropene equimolar amounts, reacts 1.5 hours, and products therefrom is γ-chloropropyl trichloro-silane, and reaction yield is
83.5%.
Embodiment 3
(1) a kind of catalyst for catalyzing and synthesizing γ-chloropropyl trichloro-silane, its structure is the polyacetylene as shown in P5
Loading nitrogenous heterocyclic platinum complex, wherein, n is the integer more than zero.
The above-mentioned catalyst for catalyzing and synthesizing γ-chloropropyl trichloro-silane, i.e. polyacetylene load nitrogen heterocyclic ring as shown in formula P5
The synthetic method of platinum complex, step is as follows:
1) side chain is connected with the synthesis of nitrogenous heterocyclic disubstituted polyacetylene
Weigh polyacetylene macromolecule P1 (80mg), azepine-18-crown-6 (96mg), potassium carbonate (51mg), potassium iodide (20mg)
In dry Schlenk pipe, it is stoppered saline plug, logical nitrogen 5-6 time of bleeding, in the case of logical nitrogen, add anhydrous
DMF (3mL) and anhydrous THF (3mL), reacts 3 days in 75 DEG C under nitrogen protection；
After gained product is filtered, it is added dropwise in the conical flask containing 100mL methanol of magneton stirring, has faint yellow
Precipitation, sucking filtration goes out gained precipitation；Then, after this precipitation is dissolved with oxolane, it is further dropped into containing of magneton stirring
In the conical flask of 100mL methanol, again separating out precipitation, sucking filtration gained filter cake methanol washs repeatedly；Finally, collect orange
Solid is dried under vacuum to constant weight in 45 DEG C, obtains side chain and is connected with nitrogenous heterocyclic disubstituted polyacetylene (86mg), and productivity is
63%.
2) polyacetylene loads the synthesis of nitrogenous heterocyclic platinum complex P5
Weigh side chain and be connected with nitrogenous heterocyclic disubstituted polyacetylene (60mg) with potassium chloroplatinite (46mg) in dry Schlenk
Guan Zhong, adds acetone, return stirring 4 days；Being filtered out by gained solid product, and repeatedly wash with acetone and water, filtering residue is true
Empty dry, i.e. obtain light yellow polyacetylene and load nitrogenous heterocyclic platinum complex P5, be i.e. used for catalyzing and synthesizing γ-chloropropyl trichlorine
The catalyst of silane.
(2) method of above-mentioned catalyst synthesis γ-chloropropyl trichloro-silane, specifically comprises the following steps that equipped with reflux condensation mode
The reaction bulb of pipe adds chloropropene (3.8g) and catalyst P5 (0.5mg), at 55 DEG C, activates 30min, be subsequently adding and
The trichlorosilane of chloropropene equimolar amounts, reacts 1.2 hours, and products therefrom is γ-chloropropyl trichloro-silane, and reaction yield is
82.3%.
In sum, the mol ratio of consumption and the reaction substrate chloropropene of the nitrogenous heterocyclic platinum complex catalyst of polyacetylene load
Than being only 1 × 10-6～1 × 10-5, catalyst amount is few；And the productivity of this catalyst synthesis γ-chloropropyl trichloro-silane is all
More than 80%, productivity is high；Response time, response speed was fast both less than equal to 1.5 hours；Reaction temperature all 60 DEG C with
Under, reaction temperature is low.
The above is only the preferred embodiment of the present invention, it is noted that for the person of ordinary skill of the art,
On the premise of conceiving without departing from the invention, it is also possible to making some modifications and variations, these broadly fall into the protection model of the present invention
Enclose.
Claims (10)
1. the catalyst being used for catalyzing and synthesizing γ-chloropropyl trichloro-silane, it is characterised in that its structure is for such as formula (I) institute
The polyacetylene nitrogenous heterocyclic platinum complex of load shown:
Wherein, n is the integer more than zero, and R-Pt is nitrogenous heterocyclic platinum complex group, and R is nitrogen heterocyclic ring group, its with
The connection site of position, side alkyl chain is atom N；Hetero atom in described nitrogen heterocyclic ring group is in N, O, S atom
Kind or several, hetero atom number be x, x time m=6-x, x are more than 6 when being not more than 6 m be 0.
The most according to claim 1 for catalyzing and synthesizing the catalyst of γ-chloropropyl trichloro-silane, it is characterised in that described nitrogenous
One or more in structure as shown in formula 1a～formula 1k of the platinum complex group R-Pt of heterocycle:
3., for catalyzing and synthesizing the preparation method of the catalyst of γ-chloropropyl trichloro-silane described in claim 1 or 2, its feature exists
It is connected with nitrogenous heterocyclic disubstituted polyacetylene in side chain and carries out complexation reaction with the Pt in potassium chloroplatinite, obtain structure such as formula
(I) polyacetylene shown in loads nitrogenous heterocyclic platinum complex, is the catalysis for catalyzing and synthesizing γ-chloropropyl trichloro-silane
Agent；
Described side chain is connected with shown in nitrogenous heterocyclic disubstituted polyacetylene structure such as formula (II):
Wherein, R is nitrogen heterocyclic ring group, and it is atom N with the connection site of position, side alkyl chain；Described nitrogen heterocyclic ring group
In hetero atom be one or more in N, O, S atom.
The most according to claim 3 for catalyzing and synthesizing the preparation method of the catalyst of γ-chloropropyl trichloro-silane, its feature
Being that described side chain is connected with the mol ratio of nitrogen heterocyclic ring and potassium chloroplatinite in nitrogenous heterocyclic disubstituted polyacetylene is 1:2～1:1.
The most according to claim 3, for catalyzing and synthesizing the preparation method of the catalyst of γ-chloropropyl trichloro-silane, its feature exists
Temperature in described complexation reaction is 60～80 DEG C, and solvent is organic solvent miscible with water.
6. the method catalyzing and synthesizing γ-chloropropyl trichloro-silane, it is characterised in that mainly comprise the following steps: chloropropene and catalyst mix
Conjunction post-heating activates, and is subsequently adding trichlorosilane and carries out hydrosilylation, and products therefrom is γ-chloropropyl trichloro-silane；
Described catalyst is the structure polyacetylene nitrogenous heterocyclic platinum complex of load as shown in formula (I):
Wherein, n is the integer more than zero, and R-Pt is nitrogenous heterocyclic platinum complex group, and R is nitrogen heterocyclic ring group, its with
The connection site of position, side alkyl chain is atom N；Hetero atom in described nitrogen heterocyclic ring group is in N, O, S atom
Kind or several, hetero atom number be x, x time m=6-x, x are more than 6 when being not more than 6 m be 0.
The method catalyzing and synthesizing γ-chloropropyl trichloro-silane the most according to claim 6, it is characterised in that described heat-activated
Temperature be 40～80 DEG C, the time is 10～30min.
The method catalyzing and synthesizing γ-chloropropyl trichloro-silane the most according to claim 6, it is characterised in that described Si-H addition reaction
The temperature of reaction is 40～80 DEG C, and the response time is 1～1.5 hour.
The method catalyzing and synthesizing γ-chloropropyl trichloro-silane the most according to claim 6, it is characterised in that described chloropropene with
Catalyst, the mol ratio of trichlorosilane are 1:(1 × 10-6～1 × 10-5): 1.
The method catalyzing and synthesizing γ-chloropropyl trichloro-silane the most according to claim 6, it is characterised in that described silicon hydrogen adds
The environment becoming reaction is inert atmosphere, anhydrous condition.
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| CN108516993A (en) * | 2018-05-07 | 2018-09-11 | 广东工业大学 | A kind of sulfur poisoning-resistant platinum complex compound and its application |
| CN109999905A (en) * | 2018-12-28 | 2019-07-12 | 北京航空航天大学 | A kind of preparation and application of highly selective hydrosilylation catalyst |
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| CN109999905A (en) * | 2018-12-28 | 2019-07-12 | 北京航空航天大学 | A kind of preparation and application of highly selective hydrosilylation catalyst |
| CN109999905B (en) * | 2018-12-28 | 2021-08-20 | 北京深云智合科技有限公司 | Preparation and application of high-selectivity hydrosilylation catalyst |
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