DE1078120B - Verfahren zur Herstellung von 1, 2, 4-Tricarboxy-3-carboxymethyl-cyclopentan bzw. dessen Anhydrid - Google Patents
Verfahren zur Herstellung von 1, 2, 4-Tricarboxy-3-carboxymethyl-cyclopentan bzw. dessen AnhydridInfo
- Publication number
- DE1078120B DE1078120B DEP21292A DEP0021292A DE1078120B DE 1078120 B DE1078120 B DE 1078120B DE P21292 A DEP21292 A DE P21292A DE P0021292 A DEP0021292 A DE P0021292A DE 1078120 B DE1078120 B DE 1078120B
- Authority
- DE
- Germany
- Prior art keywords
- tricarboxy
- acid
- anhydride
- alcohol
- dianhydride
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000008064 anhydrides Chemical class 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 6
- RHRNYXVSZLSRRP-UHFFFAOYSA-N 3-(carboxymethyl)cyclopentane-1,2,4-tricarboxylic acid Chemical compound OC(=O)CC1C(C(O)=O)CC(C(O)=O)C1C(O)=O RHRNYXVSZLSRRP-UHFFFAOYSA-N 0.000 title 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 229910017604 nitric acid Inorganic materials 0.000 claims description 12
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 8
- -1 benzoic acid ester Chemical class 0.000 claims description 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 5
- 239000012346 acetyl chloride Substances 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 claims description 2
- 239000011133 lead Substances 0.000 claims description 2
- 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 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052715 tantalum Inorganic materials 0.000 claims description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- 239000002253 acid Substances 0.000 description 15
- HRWRJUVJOLBMST-LXWZSJDBSA-N 27137-33-3 Chemical compound C1C[C@@H]2C3C(O)C=CC3[C@H]1C2 HRWRJUVJOLBMST-LXWZSJDBSA-N 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 10
- 230000003647 oxidation Effects 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000006159 dianhydride group Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4215—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US685424A US3080418A (en) | 1957-09-23 | 1957-09-23 | Process for the preparation of trans, cis, trans-1, 2, 4-tricarboxy-cis-3-carboxymethylocylopentane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1078120B true DE1078120B (de) | 1960-03-24 |
Family
ID=24752152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP21292A Pending DE1078120B (de) | 1957-09-23 | 1958-09-02 | Verfahren zur Herstellung von 1, 2, 4-Tricarboxy-3-carboxymethyl-cyclopentan bzw. dessen Anhydrid |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3080418A (enExample) |
| DE (1) | DE1078120B (enExample) |
| FR (1) | FR1207769A (enExample) |
| GB (1) | GB823840A (enExample) |
| NL (1) | NL231511A (enExample) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1141988B (de) * | 1960-04-28 | 1963-01-03 | Grace W R & Co | Verfahren zur Herstellung von 2, 3, 5-Tricarboxycyclopentylessigsaeure |
| WO2011131649A1 (en) | 2010-04-23 | 2011-10-27 | Rolic Ag | Photoaligning material |
| WO2013017467A1 (en) | 2011-08-02 | 2013-02-07 | Rolic Ag | Photoaligning material |
| WO2013026691A1 (en) | 2011-08-25 | 2013-02-28 | Rolic Ag | Photoreactive compounds |
| WO2013050121A1 (en) | 2011-10-03 | 2013-04-11 | Rolic Ag | Photoaligning materials |
| WO2013050122A1 (en) | 2011-10-03 | 2013-04-11 | Rolic Ag | Photoaligning materials |
| WO2018069071A1 (en) | 2016-10-11 | 2018-04-19 | Rolic Technologies AG | Photoaligning copolymer materials |
| US10696795B2 (en) | 2015-11-11 | 2020-06-30 | Rolic Technologies AG | Photoaligning materials |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3194816A (en) * | 1961-12-18 | 1965-07-13 | Copolymer Rubber & Chem Corp | Purification of 1, 2, 3, 4-cyclopentanetet-racarboxylic acid and preparation of its anhydride |
| US3242206A (en) * | 1961-12-18 | 1966-03-22 | Copolymer Rubber & Chem Corp | Recycling a portion of the reaction products in an hno3 oxidation of a dicarboxy cycloalkene compound to control the oxidation rate |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1960211A (en) * | 1932-11-03 | 1934-05-22 | Dow Chemical Co | Preparation of adipic acids |
| US2615008A (en) * | 1945-09-18 | 1952-10-21 | Devoe & Raynolds Co | Epoxide resin compositions |
| US2750411A (en) * | 1951-11-14 | 1956-06-12 | Gordon S Fisher | Converting alpha-pinene to mixtures of acids |
| US2668807A (en) * | 1952-04-08 | 1954-02-09 | Devoe & Raynolds Co | Epoxide compositions |
| US2806057A (en) * | 1953-02-24 | 1957-09-10 | Shell Dev | Hydroxy-substituted tetrahydrophthalic acids, derivatives thereof, and method for producing the same |
| US2798079A (en) * | 1953-12-29 | 1957-07-02 | Universal Oil Prod Co | Condensation of aromatic hydrocarbon derivatives with carbohydrates and related materials |
| US2782233A (en) * | 1955-03-11 | 1957-02-19 | Du Pont | Boric tris-(fluorocarboxylic) anhydrides |
| US2798080A (en) * | 1956-05-10 | 1957-07-02 | Eastman Kodak Co | Process of manufacturing mixed anhydrides of carboxylic acids |
-
0
- NL NL231511D patent/NL231511A/xx unknown
-
1957
- 1957-09-23 US US685424A patent/US3080418A/en not_active Expired - Lifetime
-
1958
- 1958-05-30 GB GB17403/58A patent/GB823840A/en not_active Expired
- 1958-07-10 FR FR1207769D patent/FR1207769A/fr not_active Expired
- 1958-09-02 DE DEP21292A patent/DE1078120B/de active Pending
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1141988B (de) * | 1960-04-28 | 1963-01-03 | Grace W R & Co | Verfahren zur Herstellung von 2, 3, 5-Tricarboxycyclopentylessigsaeure |
| US9097938B2 (en) | 2010-04-23 | 2015-08-04 | Rolic Ag | Photoaligning material |
| WO2011131649A1 (en) | 2010-04-23 | 2011-10-27 | Rolic Ag | Photoaligning material |
| WO2013017467A1 (en) | 2011-08-02 | 2013-02-07 | Rolic Ag | Photoaligning material |
| US9765235B2 (en) | 2011-08-02 | 2017-09-19 | Rolic Ag | Photoaligning material |
| WO2013026691A1 (en) | 2011-08-25 | 2013-02-28 | Rolic Ag | Photoreactive compounds |
| US9366906B2 (en) | 2011-08-25 | 2016-06-14 | Rolic Ag | Photoreactive compounds |
| WO2013050122A1 (en) | 2011-10-03 | 2013-04-11 | Rolic Ag | Photoaligning materials |
| US9334366B2 (en) | 2011-10-03 | 2016-05-10 | Rolic Ag | Photoaligning materials |
| US9493394B2 (en) | 2011-10-03 | 2016-11-15 | Rolic Ag | Photoaligning materials |
| WO2013050121A1 (en) | 2011-10-03 | 2013-04-11 | Rolic Ag | Photoaligning materials |
| US10696795B2 (en) | 2015-11-11 | 2020-06-30 | Rolic Technologies AG | Photoaligning materials |
| US11098164B2 (en) | 2015-11-11 | 2021-08-24 | Rolic Technologies AG | Photoaligning materials |
| US11634544B2 (en) | 2015-11-11 | 2023-04-25 | Rolic Technologies AG | Photoaligning materials |
| WO2018069071A1 (en) | 2016-10-11 | 2018-04-19 | Rolic Technologies AG | Photoaligning copolymer materials |
Also Published As
| Publication number | Publication date |
|---|---|
| NL231511A (enExample) | |
| FR1207769A (fr) | 1960-02-18 |
| GB823840A (en) | 1959-11-18 |
| US3080418A (en) | 1963-03-05 |
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