DD141303A5 - Verfahren zur herstellung von aethylestern - Google Patents
Verfahren zur herstellung von aethylestern Download PDFInfo
- Publication number
- DD141303A5 DD141303A5 DD21045779A DD21045779A DD141303A5 DD 141303 A5 DD141303 A5 DD 141303A5 DD 21045779 A DD21045779 A DD 21045779A DD 21045779 A DD21045779 A DD 21045779A DD 141303 A5 DD141303 A5 DD 141303A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- item
- acid
- catalyst
- reaction
- solvent
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 239000003054 catalyst Substances 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 24
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 21
- 239000005977 Ethylene Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 15
- 125000004494 ethyl ester group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 9
- 239000007791 liquid phase Substances 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 7
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 7
- 239000003377 acid catalyst Substances 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
- MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 claims description 2
- 235000014121 butter Nutrition 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- -1 tetramethyl sulfone Chemical class 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 claims 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 239000012429 reaction media Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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
- 125000003118 aryl group Chemical group 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 1
- OJNUEXZCVLUSOI-UHFFFAOYSA-N 2,2-dichlorothiolane 1,1-dioxide Chemical compound ClC1(Cl)CCCS1(=O)=O OJNUEXZCVLUSOI-UHFFFAOYSA-N 0.000 description 1
- WKFQMDFSDQFAIC-UHFFFAOYSA-N 2,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CC(C)S(=O)(=O)C1 WKFQMDFSDQFAIC-UHFFFAOYSA-N 0.000 description 1
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7801570A FR2414491A1 (fr) | 1978-01-16 | 1978-01-16 | Procede pour la preparation d'esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD141303A5 true DD141303A5 (de) | 1980-04-23 |
Family
ID=9203668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD21045779A DD141303A5 (de) | 1978-01-16 | 1979-01-12 | Verfahren zur herstellung von aethylestern |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5822094B2 (en, 2012) |
| DD (1) | DD141303A5 (en, 2012) |
| FR (1) | FR2414491A1 (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58183640A (ja) * | 1982-04-20 | 1983-10-26 | Nippon Synthetic Chem Ind Co Ltd:The | 酢酸エステルの製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3474131A (en) * | 1966-10-31 | 1969-10-21 | Universal Oil Prod Co | Preparation of primary alkyl esters |
-
1978
- 1978-01-16 FR FR7801570A patent/FR2414491A1/fr active Granted
-
1979
- 1979-01-12 DD DD21045779A patent/DD141303A5/de unknown
- 1979-01-12 JP JP284079A patent/JPS5822094B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2414491A1 (fr) | 1979-08-10 |
| JPS5822094B2 (ja) | 1983-05-06 |
| JPS54154708A (en) | 1979-12-06 |
| FR2414491B1 (en, 2012) | 1980-08-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2005077878A1 (de) | Verfahren zur herstellung von alpha-hydroxycarbonsäuren und deren ester | |
| DE2847170C2 (de) | Verfahren zur kontinuierlichen Herstellung von Terephthalsäure | |
| DE60207490T2 (de) | Verfahren zur Herstellung von (Meth)Acrylsäureanhydrid | |
| EP0031886B1 (de) | Verfahren zur Herstellung von Isobuttersäure oder ihrer niederen Alkylester | |
| DE10106627C1 (de) | Verfahren zur Herstellung von Estern der Citronensäure | |
| EP0433420B1 (de) | Verfahren zur herstellung symmetrischer difettsäurediamide | |
| DE69109000T2 (de) | Verfahren zur Herstellung von 4-Hydroxybutyl(meth)acrylat. | |
| EP0295554B1 (de) | Verfahren zur Herstellung von Omega-Formylalkancarbonsäureestern | |
| DE102004008575A1 (de) | Spaltung oligomerer (Meth)acrylsäure in flüssiger Phase unter Druck | |
| EP1047658B1 (de) | Verfahren zur herstellung von alkoxylierten dimerfettsäuren | |
| DD141303A5 (de) | Verfahren zur herstellung von aethylestern | |
| DE3003126A1 (de) | Verfahren zur herstellung von sek.-butanol | |
| EP0765861B1 (de) | Verfahren zur Herstellung von Alkylestern der (Meth)acrylsäure | |
| DE10132526A1 (de) | Verfahren zum Herstellen eines Alkanderivats | |
| DE19727234C1 (de) | Verfahren zur Herstellung eines Alkyl(meth)acrylats | |
| DE69804792T2 (de) | Verfahren zur herstellung von carbonsäuren | |
| DD141304A5 (de) | Verfahren zur herstellung von aethyl-und isopropylestern | |
| DE4445825C2 (de) | Monoalkylphosphin und Verfahren zur Herstellung desselben | |
| DE69017864T2 (de) | Verfahren zur Herstellung von Phenol. | |
| DE1064941B (de) | Verfahren zur Herstellung von Gemischen aus gesaettigten aliphatischen oder cycloaliphatischen Monocarbonsaeurealkylestern | |
| DE69805980T2 (de) | Verfahren zur herstellung von carbonsäuren | |
| EP0128489B1 (de) | Verfahren zur Herstellung von Succinylobernsteinsäuredialkylestern | |
| EP0050870B1 (de) | Verfahren zur Herstellung von N-tert.-Alkylaminen oder Cycloalkylaminen und Estern der Ameisensäure | |
| EP0623579A1 (de) | Verfahren zur Herstellung von Ethercarbonsäuren | |
| EP0351616A2 (de) | Verfahren zur Herstellung von Pentensäurealkylestern |