DE2009505A1 - Isonananole sowie deren Verwendung in Form von Bis Isononylestern der Phthal saure oder Adipinsäure - Google Patents
Isonananole sowie deren Verwendung in Form von Bis Isononylestern der Phthal saure oder AdipinsäureInfo
- Publication number
- DE2009505A1 DE2009505A1 DE19702009505 DE2009505A DE2009505A1 DE 2009505 A1 DE2009505 A1 DE 2009505A1 DE 19702009505 DE19702009505 DE 19702009505 DE 2009505 A DE2009505 A DE 2009505A DE 2009505 A1 DE2009505 A1 DE 2009505A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- acid
- adipic acid
- esters
- isononyl
- 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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 title claims description 23
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 title claims description 22
- 239000001361 adipic acid Substances 0.000 title claims description 12
- 235000011037 adipic acid Nutrition 0.000 title claims description 12
- -1 isononyl esters Chemical class 0.000 title description 6
- 150000002148 esters Chemical class 0.000 claims description 17
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical class CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 claims description 13
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 10
- 239000004800 polyvinyl chloride Substances 0.000 claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- XTVRLCUJHGUXCP-UHFFFAOYSA-N 3-methyleneheptane Chemical compound CCCCC(=C)CC XTVRLCUJHGUXCP-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 239000004014 plasticizer Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 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
- 150000002739 metals Chemical class 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 4
- AYWLCKHHUFBVGJ-UHFFFAOYSA-N bis(7-methyloctyl) hexanedioate Chemical compound CC(C)CCCCCCOC(=O)CCCCC(=O)OCCCCCCC(C)C AYWLCKHHUFBVGJ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001278 adipic acid derivatives Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical class CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical group 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 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
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- NMNZGKIKHBYUNG-UHFFFAOYSA-L cobalt(2+);hexanoate Chemical compound [Co+2].CCCCCC([O-])=O.CCCCCC([O-])=O NMNZGKIKHBYUNG-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- ZUBZATZOEPUUQF-UHFFFAOYSA-N isononane Chemical class CCCCCCC(C)C ZUBZATZOEPUUQF-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702009505 DE2009505A1 (de) | 1970-02-28 | 1970-02-28 | Isonananole sowie deren Verwendung in Form von Bis Isononylestern der Phthal saure oder Adipinsäure |
| CA105,649A CA978991A (en) | 1970-02-28 | 1971-02-17 | Isononanols and their use in the form of bis-isononyl esters of phthalic acid or adipic acid |
| FR7105919A FR2078892A5 (enExample) | 1970-02-28 | 1971-02-22 | |
| BE763494A BE763494A (fr) | 1970-02-28 | 1971-02-26 | Isononanols et leur emploi sous forme de diesters isononyliquesde l'acide phtalique ou de l'acide adipique |
| ES388691A ES388691A1 (es) | 1970-02-28 | 1971-02-27 | Procedimiento para la obtencion de esteres bis-isononili- cos. |
| GB2267371A GB1330112A (en) | 1970-02-28 | 1971-04-19 | Isononanols and their use in the form of bis-isononyl esters of phthalic acid or adipic acid as plasticizers for polyvinyl chloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702009505 DE2009505A1 (de) | 1970-02-28 | 1970-02-28 | Isonananole sowie deren Verwendung in Form von Bis Isononylestern der Phthal saure oder Adipinsäure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2009505A1 true DE2009505A1 (de) | 1971-09-09 |
Family
ID=5763685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702009505 Pending DE2009505A1 (de) | 1970-02-28 | 1970-02-28 | Isonananole sowie deren Verwendung in Form von Bis Isononylestern der Phthal saure oder Adipinsäure |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE763494A (enExample) |
| CA (1) | CA978991A (enExample) |
| DE (1) | DE2009505A1 (enExample) |
| ES (1) | ES388691A1 (enExample) |
| FR (1) | FR2078892A5 (enExample) |
| GB (1) | GB1330112A (enExample) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2855421A1 (de) * | 1977-12-23 | 1979-07-05 | Nissan Chemical Ind Ltd | Weichmacher |
| WO2000063151A1 (de) * | 1999-04-21 | 2000-10-26 | Basf Aktiengesellschaft | Gemisch von diestern der adipin- oder phthalsäure mit isomeren nonanolen |
| US7323588B2 (en) | 2002-04-18 | 2008-01-29 | Oxeno Olefinchemie Gmbh | Isononyl benzoates and their use |
| WO2010063740A1 (de) | 2008-12-05 | 2010-06-10 | Basf Se | Cyclohexanpolycarbonsäure-derivate als weichmacher für kleb- und dichtstoffe |
| WO2011054781A1 (de) | 2009-11-03 | 2011-05-12 | Basf Se | THERMOPLASTISCHE ZUSAMMENSETZUNGEN MIT VERBESSERTER FLIEßFÄHIGKEIT |
| EP2377844A2 (de) | 2004-06-21 | 2011-10-19 | Basf Se | Hilfsmittel enthaltend Cyclohexanpolycarbonsäurederivate |
| WO2011151301A1 (de) | 2010-06-01 | 2011-12-08 | Basf Se | Verfahren zur herstellung von expandierbaren styrolpolymer-zusammensetzungen |
| WO2016026838A1 (de) | 2014-08-19 | 2016-02-25 | Basf Se | Weichmacher-zusammensetzung, die polymere dicarbonsäureester enthält |
| WO2017055429A1 (de) | 2015-09-30 | 2017-04-06 | Basf Se | Weichmacher-zusammensetzung, die polymere dicarbonsäureester und 1,2-cyclohexandicarbonsäureester enthält |
| WO2017055432A1 (de) | 2015-09-30 | 2017-04-06 | Basf Se | Weichmacher-zusammensetzung, die polymere dicarbonsäureester und terephthalsäuredialkylester enthält |
| WO2017055431A1 (de) | 2015-09-30 | 2017-04-06 | Basf Se | Weichmacher-zusammensetzung, die polymere dicarbonsäureester und dicarbonsäurediester enthält |
| US10273345B2 (en) | 2014-09-04 | 2019-04-30 | Basf Se | Plasticizer composition which contains a polymer dicarboxylic acid ester |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004033410A1 (de) * | 2004-02-14 | 2005-09-01 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Olefinen mit 8 bis 12 Kohlenstoffatomen |
| CN1993309B (zh) | 2004-08-04 | 2010-11-10 | 埃克森美孚化学专利公司 | C8-c10醇的混合物以及衍生的增塑剂和表面活性剂 |
-
1970
- 1970-02-28 DE DE19702009505 patent/DE2009505A1/de active Pending
-
1971
- 1971-02-17 CA CA105,649A patent/CA978991A/en not_active Expired
- 1971-02-22 FR FR7105919A patent/FR2078892A5/fr not_active Expired
- 1971-02-26 BE BE763494A patent/BE763494A/xx unknown
- 1971-02-27 ES ES388691A patent/ES388691A1/es not_active Expired
- 1971-04-19 GB GB2267371A patent/GB1330112A/en not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2855421A1 (de) * | 1977-12-23 | 1979-07-05 | Nissan Chemical Ind Ltd | Weichmacher |
| WO2000063151A1 (de) * | 1999-04-21 | 2000-10-26 | Basf Aktiengesellschaft | Gemisch von diestern der adipin- oder phthalsäure mit isomeren nonanolen |
| US7323588B2 (en) | 2002-04-18 | 2008-01-29 | Oxeno Olefinchemie Gmbh | Isononyl benzoates and their use |
| EP2377844A2 (de) | 2004-06-21 | 2011-10-19 | Basf Se | Hilfsmittel enthaltend Cyclohexanpolycarbonsäurederivate |
| WO2010063740A1 (de) | 2008-12-05 | 2010-06-10 | Basf Se | Cyclohexanpolycarbonsäure-derivate als weichmacher für kleb- und dichtstoffe |
| WO2011054781A1 (de) | 2009-11-03 | 2011-05-12 | Basf Se | THERMOPLASTISCHE ZUSAMMENSETZUNGEN MIT VERBESSERTER FLIEßFÄHIGKEIT |
| WO2011151301A1 (de) | 2010-06-01 | 2011-12-08 | Basf Se | Verfahren zur herstellung von expandierbaren styrolpolymer-zusammensetzungen |
| WO2016026838A1 (de) | 2014-08-19 | 2016-02-25 | Basf Se | Weichmacher-zusammensetzung, die polymere dicarbonsäureester enthält |
| US10266672B2 (en) | 2014-08-19 | 2019-04-23 | Basf Se | Plasticizer composition comprising polymeric dicarboxylic esters |
| US10273345B2 (en) | 2014-09-04 | 2019-04-30 | Basf Se | Plasticizer composition which contains a polymer dicarboxylic acid ester |
| WO2017055429A1 (de) | 2015-09-30 | 2017-04-06 | Basf Se | Weichmacher-zusammensetzung, die polymere dicarbonsäureester und 1,2-cyclohexandicarbonsäureester enthält |
| WO2017055432A1 (de) | 2015-09-30 | 2017-04-06 | Basf Se | Weichmacher-zusammensetzung, die polymere dicarbonsäureester und terephthalsäuredialkylester enthält |
| WO2017055431A1 (de) | 2015-09-30 | 2017-04-06 | Basf Se | Weichmacher-zusammensetzung, die polymere dicarbonsäureester und dicarbonsäurediester enthält |
| EP4596616A2 (de) | 2015-09-30 | 2025-08-06 | Basf Se | Weichmacher-zusammensetzung, die polymere dicarbonsäureester und dicarbonsäurediester enthält |
Also Published As
| Publication number | Publication date |
|---|---|
| ES388691A1 (es) | 1973-05-16 |
| GB1330112A (en) | 1973-09-12 |
| FR2078892A5 (enExample) | 1971-11-05 |
| BE763494A (fr) | 1971-08-26 |
| CA978991A (en) | 1975-12-02 |
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