ES2386347T3 - Procedimiento para el hidrogenado de ácidos bencenopolicarboxílicos o derivados de los mismos bajo empleo de un catalizador que presenta macroporos - Google Patents
Procedimiento para el hidrogenado de ácidos bencenopolicarboxílicos o derivados de los mismos bajo empleo de un catalizador que presenta macroporos Download PDFInfo
- Publication number
- ES2386347T3 ES2386347T3 ES03004347T ES03004347T ES2386347T3 ES 2386347 T3 ES2386347 T3 ES 2386347T3 ES 03004347 T ES03004347 T ES 03004347T ES 03004347 T ES03004347 T ES 03004347T ES 2386347 T3 ES2386347 T3 ES 2386347T3
- Authority
- ES
- Spain
- Prior art keywords
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- metal
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- 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
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- 239000003054 catalyst Substances 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title description 12
- 239000002253 acid Substances 0.000 title description 7
- 150000007513 acids Chemical class 0.000 title description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 57
- 239000002184 metal Substances 0.000 claims abstract description 57
- 239000011148 porous material Substances 0.000 claims abstract description 36
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims abstract description 29
- 230000000737 periodic effect Effects 0.000 claims abstract description 27
- 150000002148 esters Chemical class 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007789 gas Substances 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 11
- 239000000243 solution Substances 0.000 description 9
- -1 aromatic carboxylates Chemical class 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 6
- 229910052707 ruthenium Inorganic materials 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000009826 distribution Methods 0.000 description 5
- 125000005498 phthalate group Chemical class 0.000 description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003303 ruthenium Chemical class 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
- 230000002902 bimodal effect Effects 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 2
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical class OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 2
- MQHNKCZKNAJROC-UHFFFAOYSA-N dipropyl phthalate Chemical compound CCCOC(=O)C1=CC=CC=C1C(=O)OCCC MQHNKCZKNAJROC-UHFFFAOYSA-N 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 1
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 1
- PGIBJVOPLXHHGS-UHFFFAOYSA-N Di-n-decyl phthalate Chemical compound CCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCC PGIBJVOPLXHHGS-UHFFFAOYSA-N 0.000 description 1
- VOWAEIGWURALJQ-UHFFFAOYSA-N Dicyclohexyl phthalate Chemical compound C=1C=CC=C(C(=O)OC2CCCCC2)C=1C(=O)OC1CCCCC1 VOWAEIGWURALJQ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920001944 Plastisol Polymers 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SGWHIVHMTJJAGX-UHFFFAOYSA-N bis(10-methylundecyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCC(C)C SGWHIVHMTJJAGX-UHFFFAOYSA-N 0.000 description 1
- FCVOYRMLSZGTGN-UHFFFAOYSA-N bis(16-methylheptadecyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCCCCCC(C)C FCVOYRMLSZGTGN-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000005378 cyclohexanecarboxylic acids Chemical class 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- JVJDKGTXHBCLLJ-UHFFFAOYSA-N diicosyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCCCCCCCCCC JVJDKGTXHBCLLJ-UHFFFAOYSA-N 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 description 1
- MQKMBXOZOISLIV-UHFFFAOYSA-N dioctadecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCCCCCCCC MQKMBXOZOISLIV-UHFFFAOYSA-N 0.000 description 1
- RYCNBIYTZSGSPI-UHFFFAOYSA-N ditert-butyl benzene-1,2-dicarboxylate Chemical compound CC(C)(C)OC(=O)C1=CC=CC=C1C(=O)OC(C)(C)C RYCNBIYTZSGSPI-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- PMDKYLLIOLFQPO-UHFFFAOYSA-N monocyclohexyl phthalate Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC1CCCCC1 PMDKYLLIOLFQPO-UHFFFAOYSA-N 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000004999 plastisol Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000002459 porosimetry Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/75—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19756913A DE19756913A1 (de) | 1997-12-19 | 1997-12-19 | Verfahren zur Hydrierung von Benzendicarbonsäureestern unter Verwendung eines Makroporen aufweisenden Katalysators |
| DE19756913 | 1997-12-19 | ||
| DE19832088 | 1998-07-16 | ||
| DE1998132088 DE19832088A1 (de) | 1998-07-16 | 1998-07-16 | Verfahren zur Hydrierung von Benzolpolycarbonsäuren oder Derivaten davon unter Verwendung eines Makroporen aufweisenden Katalysators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2386347T3 true ES2386347T3 (es) | 2012-08-17 |
Family
ID=26042688
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03004347T Expired - Lifetime ES2386347T3 (es) | 1997-12-19 | 1998-12-18 | Procedimiento para el hidrogenado de ácidos bencenopolicarboxílicos o derivados de los mismos bajo empleo de un catalizador que presenta macroporos |
| ES98966901T Expired - Lifetime ES2199484T3 (es) | 1997-12-19 | 1998-12-18 | Procedimiento para la hidrogenacion de acidos bencenopolicarboxilicos o derivados de estos utilizando un catalizador con macroporos. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98966901T Expired - Lifetime ES2199484T3 (es) | 1997-12-19 | 1998-12-18 | Procedimiento para la hidrogenacion de acidos bencenopolicarboxilicos o derivados de estos utilizando un catalizador con macroporos. |
Country Status (16)
Families Citing this family (178)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9813786B1 (pt) * | 1997-12-19 | 2013-11-12 | Processo para hidrogenar di(isononil)ftalato ou di(isodecil)ftalato ou uma mistura de dois ou mais destes | |
| DE19927977A1 (de) * | 1999-06-18 | 2000-12-21 | Basf Ag | Verwendung von Cyclohexanpolycarbonsäuren als Weichmacher zur Herstellung toxikologisch günstig zu bewertender Kunststoffe |
| DE19927978A1 (de) * | 1999-06-18 | 2000-12-21 | Basf Ag | Ausgewählte Cyclohexan-1,3- und 1,4-dicarbonsäureester |
| AU2001258271A1 (en) * | 2000-03-13 | 2001-09-24 | Basf Aktiengesellschaft | Agrotechnical formulation |
| CN101024704B (zh) * | 2001-02-16 | 2010-08-18 | 巴斯福股份公司 | 烷基取代环己烷二羧酸及其衍生物的用途 |
| DE10128242A1 (de) | 2001-06-11 | 2002-12-12 | Basf Ag | Verfahren zur Hydrierung organischer Verbindungen |
| DE10146869A1 (de) * | 2001-09-24 | 2003-04-24 | Oxeno Olefinchemie Gmbh | Alicyclische Polycarbonsäureestergemische mit hohem trans-Anteil und Verfahren zu deren Herstellung |
| US8653184B2 (en) | 2001-09-25 | 2014-02-18 | Exxonmobil Chemical Patents Inc. | Plasticised polyvinyl chloride and processes for making the same |
| AU2002338836A1 (en) | 2001-09-25 | 2003-04-14 | Exxonmobil Chemical Patents Inc. | Plasticised polyvinyl chloride |
| DE10147776A1 (de) * | 2001-09-27 | 2003-07-03 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von alicyclischen Polycarbonsäureestern aus Partialestern aromatischer Polycarbonsäuren |
| DE10203386A1 (de) * | 2002-01-29 | 2003-07-31 | Basf Ag | Einteilige Verschlussvorrichtung aus PVC |
| DE10225565A1 (de) * | 2002-06-10 | 2003-12-18 | Oxeno Olefinchemie Gmbh | Katalysator und Verfahren zur Hydrierung von aromatischen Verbindungen |
| DE10232868A1 (de) * | 2002-07-19 | 2004-02-05 | Oxeno Olefinchemie Gmbh | Feinporiger Katalysator und Verfahren zur Hydrierung von aromatischen Verbindungen |
| DE10253802A1 (de) * | 2002-11-18 | 2004-06-03 | Degussa Ag | Verfahren zur Hydrierung von aromatischen Urethanen in Gegenwart eines geträgerten Rutheniumkatalysators |
| GB0227087D0 (en) * | 2002-11-20 | 2002-12-24 | Exxonmobil Chem Patents Inc | Hydrogenation of benzene polycarboxylic acids or derivatives thereof |
| GB0227086D0 (en) * | 2002-11-20 | 2002-12-24 | Exxonmobil Res & Eng Co | Hydrogenation processes |
| MXPA05009597A (es) * | 2003-03-14 | 2006-03-21 | Basf Ag | Tintas de impresion que comprenden derivados de acido ciclohexanpolicarboxilico. |
| DE10317870A1 (de) * | 2003-04-17 | 2004-11-04 | Crompton Vinyl Additives Gmbh | Neues Stabilisatorsystem zur Stabilisierung von halogenhaltigen Polymeren |
| ES2300520T3 (es) * | 2003-05-09 | 2008-06-16 | Basf Se | Composiciones cosmeticas que contienen derivados de acido ciclohexanopolicarboxilico. |
| CA2556389C (en) * | 2004-02-17 | 2012-03-20 | Exxonmobil Research And Engineering Company | Catalytic preparation of severely sterically hindered amino-ether alcohols using a metal loaded catalyst |
| CA2556770C (en) * | 2004-02-17 | 2012-03-20 | Exxonmobil Research And Engineering Company | Improved synthesis of severely sterically hindered amino-ether alcohols and diaminopolyalkenyl ethers using a high activity powder catalyst |
| DE102004029732A1 (de) | 2004-06-21 | 2006-01-19 | Basf Ag | Hilfsmittel enthaltend Cyclohexanpolycarbonsäurederivate |
| US7252865B2 (en) * | 2004-09-20 | 2007-08-07 | Eastman Kodak Company | Protective films containing compatible plasticizer compounds useful in polarizing plates for displays and their method of manufacture |
| DE102004063637A1 (de) * | 2004-12-31 | 2006-07-13 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von alicyclischen Carbonsäuren oder deren Derivaten |
| DE102004063673A1 (de) * | 2004-12-31 | 2006-07-13 | Oxeno Olefinchemie Gmbh | Verfahren zur kontinuierlichen katalytischen Hydrierung von hydrierbaren Verbindungen an festen, im Festbett angeordneten Katalysatoren mit einem wasserstoffhaltigen Gas |
| US7888438B2 (en) * | 2005-01-19 | 2011-02-15 | Mitsui Chemicals, Inc. | Catalyst for olefin polymerization and process for olefin polymerization |
| HUE025490T2 (en) * | 2005-01-19 | 2016-04-28 | Mitsui Chemicals Inc | Process for the production of olefin polymer |
| RU2279423C1 (ru) * | 2005-03-23 | 2006-07-10 | Ярославский государственный технический университет | Способ получения транс-4-алкилзамещенных циклогексанкарбоновых кислот |
| DE102005028752A1 (de) | 2005-06-22 | 2007-01-04 | Oxeno Olefinchemie Gmbh | Gemisch von Diisononylestern der 1,2-Cyclohexandicarbonsäure, Verfahren zu deren Herstellung und Verwendung dieser Gemische |
| US7632962B2 (en) * | 2006-04-26 | 2009-12-15 | Eastman Chemical Company | Hydrogenation process and catalysts |
| JP5044649B2 (ja) * | 2006-07-31 | 2012-10-10 | ビーエーエスエフ ソシエタス・ヨーロピア | フタレートを環水素化するためのルテニウム触媒を再生する方法 |
| EP2121202B1 (de) | 2006-12-19 | 2017-03-22 | Basf Se | Verwendung von cyclohexanpolycarbonsäureestern für die herstellung von beschichtungsstoffen für das coil-coating-verfahren und von beschichteten coils |
| US20080183004A1 (en) * | 2007-01-30 | 2008-07-31 | Nan Ya Plastics Corporation | Method of preparing cyclohexanepolycarboxylic acid ester without phthalatic and plasticizer prepared by the same |
| MY146637A (en) * | 2007-03-13 | 2012-09-14 | Exxonmobil Chem Patents Inc | Batch esterification |
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-
1998
- 1998-12-18 BR BRPI9813786-7B1A patent/BR9813786B1/pt not_active IP Right Cessation
- 1998-12-18 ID IDW20001182A patent/ID30388A/id unknown
- 1998-12-18 ES ES03004347T patent/ES2386347T3/es not_active Expired - Lifetime
- 1998-12-18 TW TW087121223A patent/TWI243188B/zh not_active IP Right Cessation
- 1998-12-18 DE DE29824628U patent/DE29824628U1/de not_active Expired - Lifetime
- 1998-12-18 KR KR1020007006693A patent/KR100688403B1/ko not_active Ceased
- 1998-12-18 CA CA2315223A patent/CA2315223C/en not_active Expired - Lifetime
- 1998-12-18 AU AU26133/99A patent/AU759882B2/en not_active Ceased
- 1998-12-18 MY MYPI98005744A patent/MY129474A/en unknown
- 1998-12-18 EP EP98966901A patent/EP1042273B1/de not_active Revoked
- 1998-12-18 EP EP03004347A patent/EP1314714B1/de not_active Expired - Lifetime
- 1998-12-18 DE DE59808306T patent/DE59808306D1/de not_active Revoked
- 1998-12-18 CN CNB988131390A patent/CN100406428C/zh not_active Expired - Lifetime
- 1998-12-18 WO PCT/EP1998/008346 patent/WO1999032427A1/de not_active Application Discontinuation
- 1998-12-18 US US09/581,843 patent/US6284917B1/en not_active Expired - Lifetime
- 1998-12-18 ES ES98966901T patent/ES2199484T3/es not_active Expired - Lifetime
- 1998-12-18 JP JP2000525365A patent/JP4664497B2/ja not_active Expired - Fee Related
-
2000
- 2000-06-15 MX MXPA/A/2000/005882 patent/MX218972B/es unknown
- 2000-06-16 IN IN123CH2000 patent/IN2000CH00123A/en unknown
-
2001
- 2001-06-13 US US09/879,456 patent/US6888021B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010033257A (ko) | 2001-04-25 |
| CA2315223C (en) | 2010-02-09 |
| AU2613399A (en) | 1999-07-12 |
| EP1314714A3 (de) | 2004-02-11 |
| TWI243188B (en) | 2005-11-11 |
| ID30388A (id) | 2001-11-29 |
| MX218972B (es) | 2004-02-04 |
| EP1314714B1 (de) | 2012-07-11 |
| BR9813786B1 (pt) | 2013-11-12 |
| CN100406428C (zh) | 2008-07-30 |
| CN1285815A (zh) | 2001-02-28 |
| US6888021B2 (en) | 2005-05-03 |
| WO1999032427A1 (de) | 1999-07-01 |
| EP1042273A1 (de) | 2000-10-11 |
| EP1314714A2 (de) | 2003-05-28 |
| EP1042273B1 (de) | 2003-05-07 |
| AU759882B2 (en) | 2003-05-01 |
| IN2000CH00123A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2005-07-22 |
| CA2315223A1 (en) | 1999-07-01 |
| DE29824628U1 (de) | 2001-11-29 |
| BR9813786A (pt) | 2000-10-03 |
| DE59808306D1 (de) | 2003-06-12 |
| JP4664497B2 (ja) | 2011-04-06 |
| US6284917B1 (en) | 2001-09-04 |
| US20020019559A1 (en) | 2002-02-14 |
| MY129474A (en) | 2007-04-30 |
| JP2001526252A (ja) | 2001-12-18 |
| ES2199484T3 (es) | 2004-02-16 |
| KR100688403B1 (ko) | 2007-03-09 |
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