DE69705162T2 - Umsetzung von hochsiedenden Rückständen der Direktsynthese in Monosilane - Google Patents
Umsetzung von hochsiedenden Rückständen der Direktsynthese in MonosilaneInfo
- Publication number
- DE69705162T2 DE69705162T2 DE69705162T DE69705162T DE69705162T2 DE 69705162 T2 DE69705162 T2 DE 69705162T2 DE 69705162 T DE69705162 T DE 69705162T DE 69705162 T DE69705162 T DE 69705162T DE 69705162 T2 DE69705162 T2 DE 69705162T2
- Authority
- DE
- Germany
- Prior art keywords
- residue
- monosilanes
- catalyst composition
- high boiling
- silicon
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000009835 boiling Methods 0.000 title claims description 52
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical class [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims description 43
- 230000015572 biosynthetic process Effects 0.000 title claims description 8
- 238000003786 synthesis reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 46
- 239000003054 catalyst Substances 0.000 claims description 32
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 24
- 229910052710 silicon Inorganic materials 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 230000003197 catalytic effect Effects 0.000 claims description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 15
- -1 silicon metalloid Chemical class 0.000 claims description 15
- 239000010703 silicon Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical group C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 claims description 12
- 239000005055 methyl trichlorosilane Substances 0.000 claims description 11
- 229910052752 metalloid Inorganic materials 0.000 claims description 10
- 150000004045 organic chlorine compounds Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 7
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 6
- 238000011065 in-situ storage Methods 0.000 claims description 6
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 claims description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical class C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 claims description 3
- 229940050176 methyl chloride Drugs 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000007038 hydrochlorination reaction Methods 0.000 description 5
- 238000003776 cleavage reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000001367 organochlorosilanes Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- PZPGRFITIJYNEJ-UHFFFAOYSA-N disilane Chemical compound [SiH3][SiH3] PZPGRFITIJYNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920000548 poly(silane) polymer Polymers 0.000 description 3
- 239000002210 silicon-based material Substances 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 229910052801 chlorine Inorganic materials 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910003910 SiCl4 Inorganic materials 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- ZXRRHFSTAFVGOC-UHFFFAOYSA-N [AlH3].[K] Chemical compound [AlH3].[K] ZXRRHFSTAFVGOC-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- FXMNVBZEWMANSQ-UHFFFAOYSA-N chloro(silyl)silane Chemical class [SiH3][SiH2]Cl FXMNVBZEWMANSQ-UHFFFAOYSA-N 0.000 description 1
- KQHIGRPLCKIXNJ-UHFFFAOYSA-N chloro-methyl-silylsilane Chemical class C[SiH]([SiH3])Cl KQHIGRPLCKIXNJ-UHFFFAOYSA-N 0.000 description 1
- AZFVLHQDIIJLJG-UHFFFAOYSA-N chloromethylsilane Chemical class [SiH3]CCl AZFVLHQDIIJLJG-UHFFFAOYSA-N 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011856 silicon-based particle Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 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
- C07F7/12—Organo silicon halides
- C07F7/16—Preparation thereof from silicon and halogenated hydrocarbons direct synthesis
-
- 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
- C07F7/128—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions covered by more than one of the groups C07F7/122 - C07F7/127 and of which the starting material is unknown or insufficiently determined
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Silicon Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/662,576 US5627298A (en) | 1996-06-13 | 1996-06-13 | One step process for converting high-boiling residue from direct process to monosilanes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69705162D1 DE69705162D1 (de) | 2001-07-19 |
| DE69705162T2 true DE69705162T2 (de) | 2002-03-07 |
Family
ID=24658281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69705162T Expired - Lifetime DE69705162T2 (de) | 1996-06-13 | 1997-05-22 | Umsetzung von hochsiedenden Rückständen der Direktsynthese in Monosilane |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5627298A (enExample) |
| EP (1) | EP0812850B1 (enExample) |
| JP (1) | JP4008533B2 (enExample) |
| KR (1) | KR100457847B1 (enExample) |
| CN (1) | CN1061659C (enExample) |
| DE (1) | DE69705162T2 (enExample) |
| MY (1) | MY117301A (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5629438A (en) * | 1996-09-11 | 1997-05-13 | Dow Corning Corporation | Hydrochlorination process for converting high-boiling residue from direct process to monosilanes |
| JP3362630B2 (ja) * | 1997-02-28 | 2003-01-07 | 信越化学工業株式会社 | 直接法メチルクロルシラン合成より副生する高沸点成分からのモノシラン類の製造方法 |
| DE19711693A1 (de) * | 1997-03-20 | 1998-09-24 | Wacker Chemie Gmbh | Verfahren zur Herstellung von Alkylchlorsilanen aus den Rückständen der Direktsynthese von Alkylchlorsilanen |
| US6013824A (en) * | 1998-12-01 | 2000-01-11 | Dow Corning Corporation | Redistributing silalkylenes in an alkyl-rich silalkylene-containing residue |
| US6013235A (en) * | 1999-07-19 | 2000-01-11 | Dow Corning Corporation | Conversion of direct process high-boiling residue to monosilanes |
| DE10039172C1 (de) * | 2000-08-10 | 2001-09-13 | Wacker Chemie Gmbh | Verfahren zum Aufarbeiten von Rückständen der Direktsynthese von Organochlorsilanen |
| KR100855672B1 (ko) * | 2001-12-18 | 2008-09-03 | 주식회사 케이씨씨 | 고비점 잔류물로부터 모노실란 제조 방법 |
| DE10336545B3 (de) * | 2003-08-05 | 2005-04-14 | Ge Bayer Silicones Gmbh & Co. Kg | Verfahren zur Herstellung von Chlorsilanen |
| CN1309725C (zh) * | 2003-09-04 | 2007-04-11 | 中国石油天然气股份有限公司 | 利用有机硅高沸物制备二甲基二氯硅烷的方法 |
| CN101786629A (zh) | 2009-01-22 | 2010-07-28 | 陶氏康宁公司 | 回收高沸点废料的方法 |
| US8697901B2 (en) | 2011-12-30 | 2014-04-15 | Momentive Performance Materials Inc. | Synthesis of organohalosilane monomers via enhanced cleavage of direct process residue |
| US8637695B2 (en) | 2011-12-30 | 2014-01-28 | Momentive Performance Materials Inc. | Synthesis of organohalosilane monomers from conventionally uncleavable Direct Process Residue |
| CN105347349B (zh) * | 2015-12-09 | 2017-04-19 | 宁夏胜蓝化工环保科技有限公司 | 气相催化转化氯代乙硅烷制备氯代单硅烷的工艺及其专用催化剂 |
| CN111377450B (zh) * | 2018-12-29 | 2025-03-14 | 江苏中能硅业科技发展有限公司 | 一种用于处理多晶硅副产高沸物的装置和方法 |
| CN114258396B (zh) | 2019-08-22 | 2024-09-20 | 美国陶氏有机硅公司 | 用于纯化硅化合物的方法 |
| CN116119672B (zh) * | 2023-03-06 | 2024-11-29 | 洛阳中硅高科技有限公司 | 四氯化硅的纯化系统和方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2380995A (en) * | 1941-09-26 | 1945-08-07 | Gen Electric | Preparation of organosilicon halides |
| US2488487A (en) * | 1946-02-07 | 1949-11-15 | Dow Chemical Co | Production of alkyl silicon halides |
| US2598435A (en) * | 1949-08-18 | 1952-05-27 | Gen Electric | Process for treating organoplysilanes |
| FR1093399A (enExample) * | 1953-02-20 | 1955-05-03 | ||
| BE536407A (enExample) * | 1954-03-12 | |||
| US4393229A (en) * | 1982-04-28 | 1983-07-12 | General Electric Company | Redistribution of polysilanes in high boiling residues |
| US5175329A (en) * | 1992-04-03 | 1992-12-29 | Dow Corning Corporation | Production of organosilanes from polysilanes |
| DE4220151A1 (de) * | 1992-06-19 | 1993-12-23 | Wacker Chemie Gmbh | Verfahren zur Gewinnung von Methylchlorsilanen aus hochsiedenden Rückständen der Methylchlorsilansynthese |
| US5292909A (en) * | 1993-07-14 | 1994-03-08 | Dow Corning Corporation | Catalytic conversion of direct process high-boiling component to chlorosilane monomers in the presence of hydrogen chloride and hydrogen |
| US5326896A (en) * | 1993-07-14 | 1994-07-05 | Dow Corning Corporation | Conversion of direct process high-boiling component to silane monomers in the presence of hydrogen gas |
| US5321147A (en) * | 1993-07-16 | 1994-06-14 | Dow Corning Corporation | Conversion of direct process high-boiling component to chlorosilane monomers in the presence of chlorine |
| US5292912A (en) * | 1993-07-19 | 1994-03-08 | Dow Corning Corporation | Catalytic conversion of direct process high-boiling component to chlorosilane monomers in the presence of hydrogen chloride |
| US5430168A (en) * | 1994-10-27 | 1995-07-04 | Dow Corning Corporation | Alumimum trichloride catalyzed hydrogenation of high-boiling residue from direct process |
-
1996
- 1996-06-13 US US08/662,576 patent/US5627298A/en not_active Expired - Lifetime
-
1997
- 1997-05-22 EP EP97303501A patent/EP0812850B1/en not_active Expired - Lifetime
- 1997-05-22 DE DE69705162T patent/DE69705162T2/de not_active Expired - Lifetime
- 1997-06-10 JP JP15201697A patent/JP4008533B2/ja not_active Expired - Fee Related
- 1997-06-11 MY MYPI97002588A patent/MY117301A/en unknown
- 1997-06-12 CN CN97113219A patent/CN1061659C/zh not_active Expired - Fee Related
- 1997-06-13 KR KR1019970024592A patent/KR100457847B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE69705162D1 (de) | 2001-07-19 |
| JPH1081506A (ja) | 1998-03-31 |
| MY117301A (en) | 2004-06-30 |
| US5627298A (en) | 1997-05-06 |
| KR100457847B1 (ko) | 2005-02-23 |
| EP0812850A3 (en) | 1998-10-28 |
| CN1061659C (zh) | 2001-02-07 |
| JP4008533B2 (ja) | 2007-11-14 |
| EP0812850B1 (en) | 2001-06-13 |
| KR980001823A (ko) | 1998-03-30 |
| CN1172114A (zh) | 1998-02-04 |
| EP0812850A2 (en) | 1997-12-17 |
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