DE860204C - Process for the preparation of ester-like condensation products - Google Patents
Process for the preparation of ester-like condensation productsInfo
- Publication number
- DE860204C DE860204C DED4320D DED0004320D DE860204C DE 860204 C DE860204 C DE 860204C DE D4320 D DED4320 D DE D4320D DE D0004320 D DED0004320 D DE D0004320D DE 860204 C DE860204 C DE 860204C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- ester
- alcohols
- molecular weight
- higher molecular
- 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
- 239000007859 condensation product Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000002148 esters Chemical class 0.000 claims description 14
- 230000032050 esterification Effects 0.000 claims description 10
- 238000005886 esterification reaction Methods 0.000 claims description 10
- 150000001735 carboxylic acids Chemical class 0.000 claims description 8
- 150000005846 sugar alcohols Polymers 0.000 claims description 7
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 150000001298 alcohols Chemical class 0.000 description 14
- 239000002253 acid Substances 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 229940055577 oleyl alcohol Drugs 0.000 description 6
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 5
- -1 etc. Substances 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940091181 aconitic acid Drugs 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 1
- JXNPEDYJTDQORS-HZJYTTRNSA-N (9Z,12Z)-octadecadien-1-ol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCO JXNPEDYJTDQORS-HZJYTTRNSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- WDYRPTWUNMHTJL-UHFFFAOYSA-N 2-(carboxymethylsulfonyl)acetic acid Chemical compound OC(=O)CS(=O)(=O)CC(O)=O WDYRPTWUNMHTJL-UHFFFAOYSA-N 0.000 description 1
- YQPCHPBGAALCRT-UHFFFAOYSA-N 2-[1-(carboxymethyl)cyclohexyl]acetic acid Chemical compound OC(=O)CC1(CC(O)=O)CCCCC1 YQPCHPBGAALCRT-UHFFFAOYSA-N 0.000 description 1
- WVDGHGISNBRCAO-UHFFFAOYSA-N 2-hydroxyisophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1O WVDGHGISNBRCAO-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- RGHNJXZEOKUKBD-MBMOQRBOSA-N D-mannonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-MBMOQRBOSA-N 0.000 description 1
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001841 cholesterols Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- JXNPEDYJTDQORS-UHFFFAOYSA-N linoleyl alcohol Natural products CCCCCC=CCC=CCCCCCCCCO JXNPEDYJTDQORS-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- 125000005608 naphthenic acid group Chemical class 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/34—Higher-molecular-weight carboxylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
Verfahren zur Herstellung von esterartigen Kondensationsprodukten Es wurde gefunden, daß man zu wertvollen esterartigen Kondensationsprodukten gelangt, wenn man auf mehrbasische Carbonsäuren höhermolekulare lipophile Reste enthaltende Oxyverbindungen in der Weise einwirken läßt, daß Ester entstehen, die noch eine freie Carboxylgruppe enthalten, und die erhaltenen Ester anschließend mit mehrwertigen Alkoholen weiterkdndensiert.Process for the preparation of ester-like condensation products It has been found that valuable ester-like condensation products are obtained if one contains higher molecular weight lipophilic residues on polybasic carboxylic acids Oxy compounds can act in such a way that esters are formed that still have a Contain free carboxyl group, and the resulting ester then with polyvalent Alcohols disseminated.
Diese Ester stellen wertvolle Wasser-in-01-Emulgatoren dar und können zur Herstellung von wäßrigen Emulsionen verwendet werden, die als emulgierbare Stoffe Mineralöle, -fette und -wachse, wie Vaseline, Paraffinöl, Ceresin usw., tierische und pflanzliche Öle und Fette, flüssige oder feste Wachse, synthetische Fettsäureester, Fettalkohole, Wachsalkohole u. dgl. enthalten.These esters are valuable water-in-oil emulsifiers and can for the production of aqueous emulsions are used as emulsifiable substances Mineral oils, fats and waxes such as petroleum jelly, paraffin oil, ceresin, etc., animal and vegetable oils and fats, liquid or solid waxes, synthetic fatty acid esters, Contain fatty alcohols, wax alcohols and the like.
Als Ausgangsstoffe für die Herstellung dieser Kondensationsprodukte kommen beispielsweise folgende mehrbasische Carbonsäuren in Betracht: Oxalsäure, Maleinsäure, Fumarsäure, Bernsteinsäure, Alkylbernsteinsäuren, GlÜtarsäure, Adipinsäure, Pimelinsäure, Korksäure, Sebazi nsäure, Cyclohexandiessigsäure, Phthalsäure, Aconitsäure, Tricarballylsäure, Trimesinsäure, Trimellithsäure, Mellithsäure ferner Diglykolsäure, Thiodiglykolsäure, Sulfondiessigsäure, Acetondicarbonsäure u. dgl. Besonders wertvolle Elnulgatoren erhält man, wenn diese Säuren durch-Oxygruppen substituiert sind, wie beispielsweise bei Tartronsäure, Apfelsäure, Weinsäure, a-Oxyglutarsäure, Trioxyglutarsäure, Mannonsäure, Citronensäure, Oxycitronensäure, Qxyisophthalsäure u, dgl. Diese Carbonsäuren können auch.noch andere Substituenten oder auch Heteroatome oder Heteroatomgruppen enthalten, wie beispielsweise Ketogruppen, Äther- und Estergruppen oder auch schwefel-und stickstoffhaltige Substituenten oder Heteroatomgruppen.As starting materials for the production of these condensation products For example, the following polybasic carboxylic acids come into consideration: oxalic acid, Maleic acid, fumaric acid, succinic acid, alkyl succinic acids, glÜtaric acid, adipic acid, Pimelic acid, suberic acid, sebacic acid, cyclohexanediacetic acid, phthalic acid, aconitic acid, Tricarballylic acid, trimesic acid, trimellitic acid, mellitic acid and diglycolic acid, Thiodiglycolic acid, sulfonediacetic acid, acetone dicarboxylic acid and the like are particularly valuable Emulsifiers is obtained when these acids are substituted by oxy groups, such as, for example with tartronic acid, malic acid, tartaric acid, a-oxyglutaric acid, trioxyglutaric acid, mannonic acid, Citric acid, oxycitric acid, hydroxyisophthalic acid and the like. These carboxylic acids can also contain other substituents or heteroatoms or heteroatom groups, such as, for example, keto groups, ether and ester groups or also those containing sulfur and nitrogen Substituents or heteroatom groups.
Erfindungsgemäß sollen diese Carbonsäuren zunächst in bekannter Weise mit höhermolekularen Oxyverbindungen verestert werden, die im Molekül wenigstens einen lipophilen Rest enthalten, Unter einem lipophilen Rest versteht man einen aliphatischen oder cycloaliphatischen Kohlenwasserstoffrest von wenigstens 6 Kohlenstoffatomen oder einen cycloaliphatischen oder aromatischen Kohlenwasserstoffrest, der eine unverzweigt aliphatische Seitenkette von wenigstens 3 Kohlenstoffatomen enthält. Als Oxygruppen enthaltende Verbindungen dieser Art, die als Kondensationskomponenten für die mehrbasischen Carbonsäuren in Betracht kommen, sind insbesondere höhermolekulare gesättigte und ungesättigte aliphatische Alkohole zu nennen, wie beispielsweise Dodecylalkohol, Hexadecylalkohol, Oktadecylalkohol, Oleylalkohol, Linoleylalkohol, Gemische höhermolekularer ungesättigter Alkohole, wie sie aus den flüssigen Wachsen der Seetieröle erhältlich sind, ferner andere höhermolekulare Wachsalkohole, wie Bienenwach#alkohole, Carnaubawachsalkohole und Montanwachsalkohole, sowie auch die aus Naphthensäuren und Harzsäuren durch katalytische Reduktion gewonnenen Naphthen- und Harzalkohole. In gleicher Weise kann man auch entsprechende, auf synthetischem Wege gewonnene Alkohole verwenden, beispielsweise höhennolekulare Paraffinalkohole, höhermolekulare perhydrierte Alkylphenole und -naphthole, .höherinolekulare Alkohole, wie sie beispielsweise aus Laurylalkohol durch Selbstkondensation in, Gegenwart alkalischer Mittel erhalten werden u, dgl. Die Kohlenwasserstoffreste dieser Alkohole können auch Substituenten enthalten oder durch Heteroatome bzw. Heteroatomgruppen unterbrochen sein. Hierfür kommen in erster Linie sauerstoffhaltige Gruppen, wie Hydroxylgruppen, Äthergruppen und vor allem Estergruppen, in Betracht. Als Beispiele für derartige Alkohole sind zu nennen die Äthylenglykolmonoester der höhermolekularen Fettsäuren, wie Laurinsäure und Ölsäure, der Diölsäureester des i, i, i-Trimethyloläthans oder der Pentaölsäurcester des Dipentaerythrits sowie entsprechende Alkyläther mit höhermolekularen aliphatischen, vorzugsweise ungesättigten Alkylresten.According to the invention, these carboxylic acids should first be esterified in a known manner with higher molecular weight oxy compounds which contain at least one lipophilic radical in the molecule. A lipophilic radical is understood to mean an aliphatic or cycloaliphatic hydrocarbon radical of at least 6 carbon atoms or a cycloaliphatic or aromatic hydrocarbon radical which has an unbranched aliphatic side chain of at least 3 carbon atoms. Compounds of this type containing oxy groups which can be used as condensation components for the polybasic carboxylic acids include, in particular, higher molecular weight saturated and unsaturated aliphatic alcohols, such as, for example, dodecyl alcohol, hexadecyl alcohol, octadecyl alcohol, oleyl alcohol, linoleyl alcohol, mixtures of higher molecular weight unsaturated alcohols such as these liquid waxes of marine animal oils are available, as well as other higher molecular weight wax alcohols such as beeswax alcohols, carnauba wax alcohols and montan wax alcohols, as well as the naphthenic and resin alcohols obtained from naphthenic acids and resin acids by catalytic reduction. In the same way it is also possible to use corresponding alcohols obtained synthetically, for example higher molecular weight paraffin alcohols, higher molecular weight perhydrogenated alkylphenols and naphthols, higher molecular weight alcohols, such as those obtained from lauryl alcohol by self-condensation in the presence of alkaline agents and the like these alcohols can also contain substituents or be interrupted by heteroatoms or heteroatom groups. For this purpose, oxygen-containing groups such as hydroxyl groups, ether groups and, above all, ester groups come into consideration. Examples of such alcohols are the ethylene glycol monoesters of higher molecular weight fatty acids, such as lauric acid and oleic acid, the dioleic acid esters of i, i, i-trimethylolethane or the pentaoleic acid esters of dipentaerythritol and corresponding alkyl ethers with higher molecular weight aliphatic, preferably unsaturated, alkyl radicals.
Die Veresterung erfolgt üi der Weise, daß das erhaltene Veresterungsprodukt noch eine freie Carboxylgruppe enthält. Es wird also auf i Mol der mehrbasischen Carbonsäuren i Mol weniger Alkohol angewendet, als der Zahl der Carboxylgruppen entspricht. Die Veresterung erfolgt nach üblichen Veresterungsverfahren, gegebenenfalls in Gegenwart von Veresterungskatalysatoren, meist durch einfaches Erhitzen ohne Lösungsmittel. Man kann die Veresterung auch in Gegenwart von Lösungs- und Verdünnungsmitteln durchführen. Ferner kann man auch an Stelle von Carbonsäuren von entsprechenden Estern mit niedermolekularen Alkoholen ausgehen und diese umestern. Die Aufarbeitung der erhaltenen sauren Ester erfolgt in üblicher Weise.The esterification takes place in such a way that the esterification product obtained still contains a free carboxyl group. So it gets to i mole of the polybasic Carboxylic acids i mole less alcohol used than the number of carboxyl groups is equivalent to. The esterification takes place by customary esterification processes, if necessary in the presence of esterification catalysts, usually by simply heating without Solvent. The esterification can also be carried out in the presence of solvents and diluents carry out. Furthermore, instead of carboxylic acids, one can also use corresponding Run out of esters with low molecular weight alcohols and transesterify them. The work-up the acidic ester obtained is carried out in the customary manner.
Nunmehr läßt man erfindungsgemäß auf diese sauren Ester mehrwertige Alkohole einwirken. ' Als solche mehrwertigen Alkohole kommen in Betracht: Äthylenglykol, i, z-Propylenglykol, I, 3-Butylenglykol, Hexandiole, Glycerin, Glycerinmonoalkyläther, Pentaerythrit, i, i, i-Trünethylolpropan, 1, 1, i-Trimethylolheptan, Dimethyldimethylolmethan, Mannit, Dulcit, Sorbit, p-Kresoldialkohol, Phenoltrialkohol u.dgl. An Stelle der mehrwertigen Alkohole kann man auch durch Äthersauerstoff oder andere Heteroatome und bzw. oder Heteroatomgruppen unterbrochene primäre mehrwertige Alkohole verwenden, wie z. B. Dipentaerythrit, Tetra-(oxäthyl)-pentaerythrit oder den Hexa-(oxäthyl)-äther des Sorbits.According to the invention, polyhydric alcohols are now allowed to act on these acidic esters. 'As such polyhydric alcohols are: ethylene glycol, i, z-propylene glycol, l, 3-butylene glycol, hexanediols, glycerol, Glycerinmonoalkyläther, pentaerythritol, i, i, i-Trünethylolpropan, 1, 1, i-trimethylolheptane, Dimethyldimethylolmethan, mannitol , Dulcitol, sorbitol, p-cresol dialcohol, phenol trial alcohol, etc. Instead of the polyhydric alcohols, primary polyhydric alcohols interrupted by ether oxygen or other heteroatoms and / or heteroatom groups can also be used, such as e.g. B. Dipentaerythritol, tetra (oxäthyl) pentaerythritol or the hexa- (oxäthyl) ether of sorbitol.
Die Einwirkung dieser mehrwertigen Alkohole auf die sauren Ester erfolgt nach den üblichen Veresterungsverfahren. Desgleichen wird auch die Aufarbeitung der erhaltenen Veresterungsprodukte in bekannter Weise durchgeführt.The action of these polyhydric alcohols on the acidic esters takes place according to the usual esterification process. The same applies to the work-up the esterification products obtained carried out in a known manner.
Mit diesen Kondensationsprodukten, also z. B. dem Mischester aus i Mol Oxalsäure, i Mol Oleylalkohol und i Mol i, i, i-Trimethylolpropan, dem Mischester aus i Mol Citronensäure, 2 Mol Oleylalkohol und i Mol Äthylenglykol, dem Mischester aus i Mol Aconitsäure, 2 Mol Oleylalkohol und i Mol Glycerin, dem Mischester aus i Mol Weinsäure, i Mol Oleylalkohol und i Mol Sorbit usw., kann man in an sich bekannter Weise Eraulsionen herstellen, insbesondere Wasser-in-01-Emulsionen, indem man die Emulgatoren der zu emulgierenden Komponente zusetzt und Wasser von gleicher Temperatur einarbeitet. Man verwendet optimal etwa 2 bis io 0/, Eraulgator auf zu emulgierenden Stoff berechnet. In die Emulsionen kann 3o bis 6o 0/, und mehrWasser eingearbeitet werden.With these condensation products, so z. B. the mixed ester of 1 mole of oxalic acid, 1 mole of oleyl alcohol and 1 mole of i, i, i-trimethylolpropane, the mixed ester of 1 mole of citric acid, 2 moles of oleyl alcohol and 1 mole of ethylene glycol, the mixed ester of 1 mole of aconitic acid, 2 moles of oleyl alcohol and i Mol glycerol, the mixed ester of one mole of tartaric acid, one mole of oleyl alcohol and one mole of sorbitol, etc., can be prepared in a manner known per se, in particular water-in-oil emulsions, by adding the emulsifiers to the component to be emulsified and water incorporated at the same temperature. Optimally, about 2 to 10% Eraulgator is used, calculated on the substance to be emulsified. 30 to 60% and more water can be incorporated into the emulsions.
Neben diesen Ernulgatoren kann man auch andere bekannte Emulgatoren, wie z. B. WoRfettalkohole und andere Cholesterinderivate, synthetische Emulgatoren usw., mit verwenden. Man kann mit Hilfe der erfindungsgemäßen Kondensationsprodukte zu Wasserin-01-Emulsionen gelangen, die leicht resorbierbare hautpflegende Substanzen enthalten, die für Pharmazie und Kosmetik von großer Bedeutung sind. Auch für technische Emulsionen sind die Emulgatoren mit Vorteil verwendbar. Beispiel 27o Gewichtsteile Oleylalkohol und io5 Gewichtsteile feinpulverisierte, kristallisierte Citronensäure werden unter Rühren und unter Durchleiten von Wasserstoff langsam ansteigend bis auf 195' erhitzt, und zwar so lange, bis etwa 27 bis 28 Gewichtsteile Wasser abdestilliert sind. Nachdem man das Gemisch hat etwas erkalten lassen, läßt man 46 Gewichtsteile Äthylenglykol zufließen und verestert in der gleichen Weise weiter, bis die Säurezahl des Reaktionsgutes unter 3 liegt und neben 9 GewichtsteiJen Wasser das im Überschuß angewandte Äthylenglykol abdestilliert ist. Man erhält 35o Gewichtsteile eines goldgelben Öls.In addition to these emulsifiers, other known emulsifiers, such as. B. WoRfettalkohole and other cholesterol derivatives, synthetic emulsifiers, etc., use with. With the aid of the condensation products according to the invention, water-in-oil emulsions can be obtained which contain easily absorbable skin-care substances which are of great importance for pharmacy and cosmetics. The emulsifiers can also be used with advantage for technical emulsions. EXAMPLE 270 parts by weight of oleyl alcohol and 10 5 parts by weight of finely powdered, crystallized citric acid are heated slowly increasing to 195 ° with stirring and while passing hydrogen through, until about 27 to 28 parts by weight of water have distilled off. After the mixture has been allowed to cool a little, 46 parts by weight of ethylene glycol are added and esterification continues in the same way until the acid number of the reaction mixture is below 3 and the excess ethylene glycol has been distilled off in addition to 9 parts by weight of water. 35o parts by weight of a golden yellow oil are obtained.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED4320D DE860204C (en) | 1941-06-22 | 1941-06-22 | Process for the preparation of ester-like condensation products |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED4320D DE860204C (en) | 1941-06-22 | 1941-06-22 | Process for the preparation of ester-like condensation products |
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| Publication Number | Publication Date |
|---|---|
| DE860204C true DE860204C (en) | 1952-12-18 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED4320D Expired DE860204C (en) | 1941-06-22 | 1941-06-22 | Process for the preparation of ester-like condensation products |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1165574B (en) * | 1960-08-08 | 1964-03-19 | Dehydag Gmbh | Process for the production of mixed esters used as emulsifiers for ointment bases |
| DE102019005969A1 (en) * | 2019-08-24 | 2021-02-25 | WeylChem Performance Products GmbH | Hydroxycarboxylic acid esters, processes for their preparation and their use |
-
1941
- 1941-06-22 DE DED4320D patent/DE860204C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1165574B (en) * | 1960-08-08 | 1964-03-19 | Dehydag Gmbh | Process for the production of mixed esters used as emulsifiers for ointment bases |
| DE102019005969A1 (en) * | 2019-08-24 | 2021-02-25 | WeylChem Performance Products GmbH | Hydroxycarboxylic acid esters, processes for their preparation and their use |
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