DE102004051267B3 - Verfahren zur kontinuierlichen Herstellung von Alkylenglykoldiethern - Google Patents
Verfahren zur kontinuierlichen Herstellung von Alkylenglykoldiethern Download PDFInfo
- Publication number
- DE102004051267B3 DE102004051267B3 DE102004051267A DE102004051267A DE102004051267B3 DE 102004051267 B3 DE102004051267 B3 DE 102004051267B3 DE 102004051267 A DE102004051267 A DE 102004051267A DE 102004051267 A DE102004051267 A DE 102004051267A DE 102004051267 B3 DE102004051267 B3 DE 102004051267B3
- Authority
- DE
- Germany
- Prior art keywords
- dimethyl ether
- catalyst
- glycol dimethyl
- formula
- diethylene glycol
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- -1 alkylene glycol Chemical compound 0.000 title claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 8
- 238000010924 continuous production Methods 0.000 title claims description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 239000007791 liquid phase Substances 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 21
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- 229910052702 rhenium Inorganic materials 0.000 claims description 4
- 229910052797 bismuth Inorganic materials 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 11
- 229910000564 Raney nickel Inorganic materials 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 9
- 239000007868 Raney catalyst Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000006959 Williamson synthesis reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004051267A DE102004051267B3 (de) | 2004-10-21 | 2004-10-21 | Verfahren zur kontinuierlichen Herstellung von Alkylenglykoldiethern |
| CN200510104065.1A CN100595179C (zh) | 2004-10-21 | 2005-09-15 | 亚烷基二醇二醚的连续制备方法 |
| EP05022109A EP1650181A1 (de) | 2004-10-21 | 2005-10-11 | Verfahren zur kontinuierlichen Herstellung von Alkylenglykoldiethern |
| JP2005305219A JP2006117676A (ja) | 2004-10-21 | 2005-10-20 | アルキレングリコールジエーテルの連続的製造方法 |
| US11/256,126 US20060089515A1 (en) | 2004-10-21 | 2005-10-21 | Process for continuously preparing alkylene glycol diethers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004051267A DE102004051267B3 (de) | 2004-10-21 | 2004-10-21 | Verfahren zur kontinuierlichen Herstellung von Alkylenglykoldiethern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102004051267B3 true DE102004051267B3 (de) | 2006-05-24 |
Family
ID=35447947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102004051267A Expired - Fee Related DE102004051267B3 (de) | 2004-10-21 | 2004-10-21 | Verfahren zur kontinuierlichen Herstellung von Alkylenglykoldiethern |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20060089515A1 (https=) |
| EP (1) | EP1650181A1 (https=) |
| JP (1) | JP2006117676A (https=) |
| CN (1) | CN100595179C (https=) |
| DE (1) | DE102004051267B3 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103641695A (zh) * | 2013-12-18 | 2014-03-19 | 河南能源化工集团研究院有限公司 | 乙二醇为原料联产乙二醇乙醚及乙二醇二乙醚的方法 |
| CN106554258B (zh) * | 2015-09-30 | 2019-07-26 | 中国科学院大连化学物理研究所 | 由乙二醇单甲醚直接制备乙二醇二甲醚并联产乙二醇的方法 |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3428692A (en) * | 1966-02-28 | 1969-02-18 | Continental Oil Co | Preparation of nonionic detergents |
| DE2434057A1 (de) * | 1974-07-16 | 1976-01-29 | Hoechst Ag | Verfahren zur herstellung von glykoldimethylaethern |
| DE2640505B1 (de) * | 1976-09-09 | 1977-12-22 | Hoechst Ag | Verfahren zur herstellung von aethern |
| DE2900279A1 (de) * | 1979-01-05 | 1980-07-24 | Hoechst Ag | Verfahren zur herstellung von methylethern |
| DE3025434A1 (de) * | 1979-07-04 | 1981-02-05 | Nisso Petrochemical Ind Co Ltd | Verfahren zur herstellung von alkylenglykoldiaethern |
| EP0043420A1 (de) * | 1980-07-03 | 1982-01-13 | Chemische Werke Hüls Ag | Verfahren zur Herstellung von methylblockierten Ethoxylaten |
| DE3128962A1 (de) * | 1981-07-22 | 1983-02-10 | Hoechst Ag, 6000 Frankfurt | "verfahren zur herstellung von alkylenglykoldiethern |
| JPS6028429A (ja) * | 1983-07-26 | 1985-02-13 | Nippon Shokubai Kagaku Kogyo Co Ltd | ポリエチレングリコ−ルジアルキルエ−テル製造用触媒 |
| DE3802783A1 (de) * | 1988-01-30 | 1989-08-10 | Hoechst Ag | Verfahren zur herstellung von alkylenglykoldialkylethern |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS568338A (en) * | 1979-07-04 | 1981-01-28 | Nisso Yuka Kogyo Kk | Preparation of ether |
| US4308402A (en) * | 1979-11-20 | 1981-12-29 | Shell Oil Company | Process for methyl-capped alkoxylates |
| CA1219285A (en) * | 1981-09-30 | 1987-03-17 | Union Carbide Corporation | Hydrogenolysis process for the production of monoethylene glycol monomethyl ether, monoethylene glycol and ethanol |
| JPH03197435A (ja) * | 1989-12-27 | 1991-08-28 | Mitsui Toatsu Chem Inc | エーテル化合物の製造法 |
| DE102006010940A1 (de) * | 2006-03-09 | 2007-09-13 | Clariant International Limited | Verfahren zur Herstellung von längerkettigen Polyalkylenglykoldiethern |
-
2004
- 2004-10-21 DE DE102004051267A patent/DE102004051267B3/de not_active Expired - Fee Related
-
2005
- 2005-09-15 CN CN200510104065.1A patent/CN100595179C/zh not_active Expired - Fee Related
- 2005-10-11 EP EP05022109A patent/EP1650181A1/de not_active Withdrawn
- 2005-10-20 JP JP2005305219A patent/JP2006117676A/ja not_active Ceased
- 2005-10-21 US US11/256,126 patent/US20060089515A1/en not_active Abandoned
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3428692A (en) * | 1966-02-28 | 1969-02-18 | Continental Oil Co | Preparation of nonionic detergents |
| DE2434057A1 (de) * | 1974-07-16 | 1976-01-29 | Hoechst Ag | Verfahren zur herstellung von glykoldimethylaethern |
| DE2640505B1 (de) * | 1976-09-09 | 1977-12-22 | Hoechst Ag | Verfahren zur herstellung von aethern |
| US4146736A (en) * | 1976-09-09 | 1979-03-27 | Hoechst Aktiengesellschaft | Process for the manufacture of ethers |
| DE2900279A1 (de) * | 1979-01-05 | 1980-07-24 | Hoechst Ag | Verfahren zur herstellung von methylethern |
| DE3025434A1 (de) * | 1979-07-04 | 1981-02-05 | Nisso Petrochemical Ind Co Ltd | Verfahren zur herstellung von alkylenglykoldiaethern |
| EP0043420A1 (de) * | 1980-07-03 | 1982-01-13 | Chemische Werke Hüls Ag | Verfahren zur Herstellung von methylblockierten Ethoxylaten |
| DE3128962A1 (de) * | 1981-07-22 | 1983-02-10 | Hoechst Ag, 6000 Frankfurt | "verfahren zur herstellung von alkylenglykoldiethern |
| JPS6028429A (ja) * | 1983-07-26 | 1985-02-13 | Nippon Shokubai Kagaku Kogyo Co Ltd | ポリエチレングリコ−ルジアルキルエ−テル製造用触媒 |
| DE3802783A1 (de) * | 1988-01-30 | 1989-08-10 | Hoechst Ag | Verfahren zur herstellung von alkylenglykoldialkylethern |
Non-Patent Citations (2)
| Title |
|---|
| K. Weissermel, H.-J. Arpe: Industrielle Organische Chemie, 1998, S. 179 |
| K. Weissermel, H.-J. Arpe: Industrielle OrganischeChemie, 1998, S. 179 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1650181A1 (de) | 2006-04-26 |
| CN100595179C (zh) | 2010-03-24 |
| US20060089515A1 (en) | 2006-04-27 |
| JP2006117676A (ja) | 2006-05-11 |
| CN1762947A (zh) | 2006-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8100 | Publication of patent without earlier publication of application | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: CLARIANT PRODUKTE (DEUTSCHLAND) GMBH, 65929 FRANKF |
|
| 8364 | No opposition during term of opposition | ||
| R119 | Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal fee |
Effective date: 20130501 |