DE3112864C2 - "Verfahren zur Stabilisierung von Glykoläthern" - Google Patents
"Verfahren zur Stabilisierung von Glykoläthern"Info
- Publication number
- DE3112864C2 DE3112864C2 DE3112864A DE3112864A DE3112864C2 DE 3112864 C2 DE3112864 C2 DE 3112864C2 DE 3112864 A DE3112864 A DE 3112864A DE 3112864 A DE3112864 A DE 3112864A DE 3112864 C2 DE3112864 C2 DE 3112864C2
- Authority
- DE
- Germany
- Prior art keywords
- ppm
- ethanol
- alcohol
- reaction
- alkoxy
- 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
Links
- -1 glycol ethers Chemical class 0.000 title claims description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 17
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 3
- 230000006641 stabilisation Effects 0.000 title description 12
- 238000011105 stabilization Methods 0.000 title description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 150000004679 hydroxides Chemical class 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- BEGTYOYMERGIDU-UHFFFAOYSA-N 5-methyloxonane Chemical class CC1CCCCOCCC1 BEGTYOYMERGIDU-UHFFFAOYSA-N 0.000 claims 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 76
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 29
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 21
- 238000003860 storage Methods 0.000 description 18
- 150000002978 peroxides Chemical class 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 239000003381 stabilizer Substances 0.000 description 12
- 229910000831 Steel Inorganic materials 0.000 description 10
- 239000010959 steel Substances 0.000 description 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- PCFUWBOSXMKGIP-UHFFFAOYSA-N 2-benzylpyridine Chemical class C=1C=CC=NC=1CC1=CC=CC=C1 PCFUWBOSXMKGIP-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- YTTFFPATQICAQN-UHFFFAOYSA-N 2-methoxypropan-1-ol Chemical compound COC(C)CO YTTFFPATQICAQN-UHFFFAOYSA-N 0.000 description 1
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 1
- FRKCZFUUIQCQPC-UHFFFAOYSA-N 2-propan-2-yloxypropan-2-ol Chemical compound CC(C)OC(C)(C)O FRKCZFUUIQCQPC-UHFFFAOYSA-N 0.000 description 1
- AODAQIOEZVDQLS-UHFFFAOYSA-N 3,4-ditert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1C(C)(C)C AODAQIOEZVDQLS-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- DPIHOWDFKXXLSJ-UHFFFAOYSA-N ethanol;piperazine Chemical class CCO.CCO.C1CNCCN1 DPIHOWDFKXXLSJ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002966 varnish 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
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/46—Use of additives, e.g. for stabilisation
-
- 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
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8007429A FR2479805A1 (fr) | 1980-04-02 | 1980-04-02 | Procede de stabilisation des ethers de glycol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3112864A1 DE3112864A1 (de) | 1982-02-18 |
| DE3112864C2 true DE3112864C2 (de) | 1983-01-05 |
Family
ID=9240457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3112864A Expired DE3112864C2 (de) | 1980-04-02 | 1981-03-31 | "Verfahren zur Stabilisierung von Glykoläthern" |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE888196A (it) |
| DE (1) | DE3112864C2 (it) |
| FR (1) | FR2479805A1 (it) |
| GB (1) | GB2073188B (it) |
| IT (1) | IT1144807B (it) |
| NL (1) | NL8101628A (it) |
| SE (1) | SE8102055L (it) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4471143A (en) * | 1980-04-21 | 1984-09-11 | The Franklin Institute | Composition for decomposing halogenated organic compounds |
| DE3125107A1 (de) * | 1981-06-26 | 1983-01-13 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung lagerstabiler (poly-)alkylenglycolmonoalkylether |
| US4737314A (en) * | 1985-02-08 | 1988-04-12 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Stabilized alkylene oxide adduct containing lactic acid or a lactate |
| BE1012770A3 (nl) * | 1999-07-02 | 2001-03-06 | Ineos Nv | Werkijze en inrichting voor het industrieel aanmaken van producten door middel van een alkoxylatiereactie. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE605973C (de) * | 1930-11-30 | 1934-11-22 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von AEthern aus hydroxylhaltigen organischen Verbindungen und AEthylenoxyd |
| NL272723A (it) * | 1951-05-31 | |||
| GB777978A (en) * | 1953-12-07 | 1957-07-03 | Dow Chemical Co | Trihydroxy polyoxyalkylene ethers of glycerine |
| DE1255653B (de) * | 1965-03-11 | 1967-12-07 | Henkel & Cie Gmbh | Verfahren zur kontinuierlichen Herstellung von Anlagerungsprodukten des AEthylenoxids |
| US3867462A (en) * | 1972-08-24 | 1975-02-18 | Dow Chemical Co | Color inhibitors in glycol ethers |
-
1980
- 1980-04-02 FR FR8007429A patent/FR2479805A1/fr active Granted
-
1981
- 1981-03-30 GB GB8109829A patent/GB2073188B/en not_active Expired
- 1981-03-31 DE DE3112864A patent/DE3112864C2/de not_active Expired
- 1981-03-31 BE BE0/204310A patent/BE888196A/fr not_active IP Right Cessation
- 1981-03-31 SE SE8102055A patent/SE8102055L/xx not_active Application Discontinuation
- 1981-04-01 NL NL8101628A patent/NL8101628A/nl not_active Application Discontinuation
- 1981-04-01 IT IT67453/81A patent/IT1144807B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| GB2073188B (en) | 1984-05-02 |
| IT8167453A0 (it) | 1981-04-01 |
| SE8102055L (sv) | 1981-10-03 |
| IT1144807B (it) | 1986-10-29 |
| NL8101628A (nl) | 1981-11-02 |
| BE888196A (fr) | 1981-09-30 |
| DE3112864A1 (de) | 1982-02-18 |
| FR2479805B1 (it) | 1982-02-26 |
| FR2479805A1 (fr) | 1981-10-09 |
| GB2073188A (en) | 1981-10-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1784375B1 (de) | Verfahren zur herstellung von ameisensäure | |
| DE69813394T2 (de) | Verfahren zur Herstellung von Methylmethacrylat | |
| EP0001083B1 (de) | Verfahren zur Herstellung von Dialkylcarbonaten | |
| DE69333037T2 (de) | Verfahren zur Herstellung von Beta-Diketonen | |
| EP0234508A2 (de) | Verfahren zur kontinuierlichen Abtrennung von Wasser aus Gemischen mit organischen Substanzen | |
| DE2937956A1 (de) | Verfahren zur herstellung von alkylenglykolen | |
| EP0413215B1 (de) | Verfahren zur Herstellung von Dialkylcarbonaten | |
| DE3641996A1 (de) | Verfahren zum abtrennen von aldehyden aus (alpha),(beta)-olefinisch ungesaettigten carbonsaeuren | |
| EP1682480A1 (de) | Verfahren zur herstellung von benzoes ureestern | |
| DE3112864C2 (de) | "Verfahren zur Stabilisierung von Glykoläthern" | |
| DE1618889B1 (de) | Verfahren zur Herstellung von 3-Methylmercaptopropionaldehyd | |
| DE10044352A1 (de) | Kontinuierliches Verfahren zur Herstellung von Acetalen | |
| DE1493971A1 (de) | Verfahren zur Herstellung von hochreinem Phenol | |
| EP1208071A2 (de) | Verfahren zur kontinuierlichen herstellung von glutaraldehyd | |
| EP1150947B1 (de) | Verfahren zur herstellung von alkansulfonsäuren | |
| DE602004012344T2 (de) | Verfahren zur Herstellung von Alkylenglykolen unter Verwendung von homogenen Katalysatoren | |
| DE1618578B1 (de) | 4 4 substituierte Dycyclohexylperoxy dikarbonate und deren Herstellung | |
| EP0193801B1 (de) | Verfahren zur kontinuierlichen Homologisierung von Methanol | |
| DE10108811B4 (de) | Reinigungsverfahren für Roh-Essigsäureanhydrid und Herstellungsverfahren für Polyoxytetramethylenglycol unter Verwendung von Essigsäureanhydrid | |
| DE1568750B2 (de) | Verfahren zur Herstellung von Äthylbenzolhydroperoxid | |
| DE10312562A1 (de) | Verfahren zur kontinuierlichen Herstellung von Acetalen von α,β-Dicarbonylverbindungen | |
| DE1173454B (de) | Verfahren zur Herstellung von N-Vinyl-carbaminsaeureestern | |
| DE2835848A1 (de) | Verfahren zur reinigung von aldehydhaltigen ketonen | |
| DE19853862A1 (de) | Verfahren zur Herstellung substituierter Cycloketone | |
| DE2428081B2 (de) | Kontinuierliches Verfahren zum Reinigen von Glyoxal |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: ATOCHEM, COURBEVOIE, HAUTS-DE-SEINE, FR |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: I.C.I. FRANCE S.A., CLAMART, FR |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: TIEDTKE, H., DIPL.-ING. BUEHLING, G., DIPL.-CHEM. KINNE, R., DIPL.-ING. GRUPE, P., DIPL.-ING. PELLMANN, H., DIPL.-ING. GRAMS, K., DIPL.-ING. STRUIF, B., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |
|
| 8331 | Complete revocation |