DE1901535C - - Google Patents
Info
- Publication number
- DE1901535C DE1901535C DE19691901535 DE1901535A DE1901535C DE 1901535 C DE1901535 C DE 1901535C DE 19691901535 DE19691901535 DE 19691901535 DE 1901535 A DE1901535 A DE 1901535A DE 1901535 C DE1901535 C DE 1901535C
- Authority
- DE
- Germany
- Prior art keywords
- oxide
- catalysts
- acid
- amine oxides
- oxides
- 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
- 239000003054 catalyst Substances 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 16
- -1 alkylene glycol Chemical compound 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 150000001735 carboxylic acids Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 21
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
- 239000005639 Lauric acid Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 230000019635 sulfation Effects 0.000 description 3
- 238000005670 sulfation reaction Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 240000007313 Tilia cordata Species 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001697 butter ester Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- VFFDVELHRCMPLY-UHFFFAOYSA-N dimethyldodecyl amine Natural products CC(C)CCCCCCCCCCCN VFFDVELHRCMPLY-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- QKJNMNGEIPLDRK-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)([O-])CCCCCCCCCCCCCCCCCC QKJNMNGEIPLDRK-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691901535 DE1901535A1 (de) | 1969-01-14 | 1969-01-14 | Verfahren zur Herstellung von Alkylenglykolestern |
| NL6918932A NL6918932A (enrdf_load_stackoverflow) | 1969-01-14 | 1969-12-17 | |
| CH9970A CH542164A (de) | 1969-01-14 | 1970-01-07 | Verfahren zur Herstellung von gegebenenfalls substituierten Alkylenglykolestern |
| BE744320D BE744320A (fr) | 1969-01-14 | 1970-01-12 | Procede de preparation d'esters d'alcoylene glycols |
| FR7001032A FR2028290A1 (enrdf_load_stackoverflow) | 1969-01-14 | 1970-01-13 | |
| GB0562/70A GB1235452A (en) | 1969-01-14 | 1970-01-13 | Improvements in the production of alkylene glycol esters |
| BR215971/70A BR7015971D0 (pt) | 1969-01-14 | 1970-01-13 | Processo para a producao de esteres de alquilenoglicol |
| US00281432A US3824263A (en) | 1969-01-14 | 1972-08-17 | Process for the production of alkyleneglycol esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691901535 DE1901535A1 (de) | 1969-01-14 | 1969-01-14 | Verfahren zur Herstellung von Alkylenglykolestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1901535A1 DE1901535A1 (de) | 1970-08-13 |
| DE1901535C true DE1901535C (enrdf_load_stackoverflow) | 1973-02-15 |
Family
ID=5722304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691901535 Granted DE1901535A1 (de) | 1969-01-14 | 1969-01-14 | Verfahren zur Herstellung von Alkylenglykolestern |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3824263A (enrdf_load_stackoverflow) |
| BE (1) | BE744320A (enrdf_load_stackoverflow) |
| BR (1) | BR7015971D0 (enrdf_load_stackoverflow) |
| CH (1) | CH542164A (enrdf_load_stackoverflow) |
| DE (1) | DE1901535A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2028290A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1235452A (enrdf_load_stackoverflow) |
| NL (1) | NL6918932A (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3884946A (en) * | 1970-05-16 | 1975-05-20 | Henkel & Cie Gmbh | Process for the production of alkylene glycol monoesters |
| AU2002239282A1 (en) * | 2000-11-28 | 2002-06-11 | Transform Pharmaceuticals, Inc. | Pharmaceutical formulations comprising paclitaxel, derivatives, and pharmaceutically acceptable salts thereof |
| AU2002357012A1 (en) * | 2001-11-27 | 2003-06-10 | Transform Pharmaceuticals, Inc. | Oral pharmaceutical formulations comprising paclitaxel, derivatives and methods of administration thereof |
| US20070031370A1 (en) * | 2005-08-04 | 2007-02-08 | Carr Richard V | Amine N-oxide based surfactants |
-
1969
- 1969-01-14 DE DE19691901535 patent/DE1901535A1/de active Granted
- 1969-12-17 NL NL6918932A patent/NL6918932A/xx unknown
-
1970
- 1970-01-07 CH CH9970A patent/CH542164A/de not_active IP Right Cessation
- 1970-01-12 BE BE744320D patent/BE744320A/xx unknown
- 1970-01-13 FR FR7001032A patent/FR2028290A1/fr not_active Withdrawn
- 1970-01-13 BR BR215971/70A patent/BR7015971D0/pt unknown
- 1970-01-13 GB GB0562/70A patent/GB1235452A/en not_active Expired
-
1972
- 1972-08-17 US US00281432A patent/US3824263A/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0025961B1 (de) | Verfahren zur Herstellung von 1,2-Diolen höherer Kohlenstoffzahl | |
| DE1901535C (enrdf_load_stackoverflow) | ||
| DE1086226B (de) | Verfahren zur Herstellung von Cyclododecatrien-(1, 5, 9) | |
| DE3442579A1 (de) | Oberflaechenaktive kondensationsprodukte | |
| EP0286937B1 (de) | Verfahren zur Herstellung epoxidierter Fettalkohole | |
| EP0005471B1 (de) | Verfahren zur Herstellung von 3-Hydroxy-2,2,4-trimethylpentylisobutyrat | |
| EP0617732B1 (de) | Verfahren zur herstellung hydrophilisierter triglyceride | |
| DE1901535A1 (de) | Verfahren zur Herstellung von Alkylenglykolestern | |
| EP0513134B1 (de) | Sulfierte hydroxycarbonsäureester | |
| DE3016571A1 (de) | Verfahren zur herstellung von perfluoralkyl-alkanolen | |
| DE2418340A1 (de) | Verfahren zur herstellung von 3,5dichlorbenzoylchlorid | |
| DE1901535B (de) | Verfahren zur Herstellung von Carbonsäurealky leng lykolmonoestern | |
| DE2523402C2 (enrdf_load_stackoverflow) | ||
| DE2724189C3 (de) | Verfahren zur Herstellung von Äthylenglykol | |
| DE3032061C1 (de) | Verfahren zur Herstellung eines verpumpbaren oberflaechenaktiven Produktes auf Basis von Polyaetheressigsaeuren | |
| DE4117935A1 (de) | Verfahren zur herstellung von alkoxylaten mit enger homologenverteilung unter verwendung von antimonpentahalogenid-komplexen als katalysator | |
| DE2337158C2 (de) | Verfahren zur Herstellung von Alkancarbonsäuren | |
| DE2064306A1 (de) | Herstellung von Monothioalkylenglykolen | |
| DE4131118A1 (de) | Verfahren zur herstellung geschmacksneutraler pasten von alkylethersulfaten in glycerin | |
| DE2040503A1 (de) | Verfahren zur Herstellung von 1,2-Glykolsulfaten | |
| DE966335C (de) | Verfahren zur Herstellung von Terephthalsaeure bzw. deren Salzen und Derivaten | |
| DE895597C (de) | Verfahren zur Herstellung von Vinylestern | |
| DE892592C (de) | Verfahren zur Herstellung von Oxyalkylsulfonen bzw. Polyoxyalkylsulfonen | |
| DE1212557B (de) | Verfahren zur Herstellung von 2, 6-Dioxy-9-oxabicyclo-[3, 3, 1]-nonan | |
| DE2848197A1 (de) | Verfahren zur herstellung von perfluorcarbonsaeuren und addukte aus einer perfluorcarbonsaeure und einem carbonsaeureamid |