DE2426964C3 - Verfahren zur Herstellung von Alkoxymethylenmalonsäuredialkylestern - Google Patents
Verfahren zur Herstellung von AlkoxymethylenmalonsäuredialkylesternInfo
- Publication number
- DE2426964C3 DE2426964C3 DE2426964A DE2426964A DE2426964C3 DE 2426964 C3 DE2426964 C3 DE 2426964C3 DE 2426964 A DE2426964 A DE 2426964A DE 2426964 A DE2426964 A DE 2426964A DE 2426964 C3 DE2426964 C3 DE 2426964C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- reaction
- malonic acid
- ester
- yield
- 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 10
- 230000008569 process Effects 0.000 title claims description 8
- 150000002148 esters Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- -1 orthoformic acid ester Chemical class 0.000 claims description 16
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 claims description 5
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 45
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 15
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 10
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 150000002905 orthoesters Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- YSEKNCXYRGKTBJ-UHFFFAOYSA-N dimethyl 2-hydroxybutanedioate Chemical compound COC(=O)CC(O)C(=O)OC YSEKNCXYRGKTBJ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- DERAACKMMNJAFU-UHFFFAOYSA-N 2-ethoxy-1,3-dioxane-4,6-dione Chemical compound CCOC1OC(=O)CC(=O)O1 DERAACKMMNJAFU-UHFFFAOYSA-N 0.000 description 1
- VHUFZXFWENGOON-UHFFFAOYSA-N 2-methoxy-1,3-dioxane-4,6-dione Chemical compound COC1OC(=O)CC(=O)O1 VHUFZXFWENGOON-UHFFFAOYSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- FBWRQBHGEWXRQD-UHFFFAOYSA-N 3-methoxy-2-methoxycarbonylprop-2-enoic acid Chemical compound COC=C(C(=O)O)C(=O)OC FBWRQBHGEWXRQD-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- MOXXPQWMYMUHHV-UHFFFAOYSA-N diethoxymethanol Chemical compound CCOC(O)OCC MOXXPQWMYMUHHV-UHFFFAOYSA-N 0.000 description 1
- ZEMAAYXNKBMRGV-UHFFFAOYSA-N diethyl 2-(ethoxymethyl)propanedioate Chemical compound CCOCC(C(=O)OCC)C(=O)OCC ZEMAAYXNKBMRGV-UHFFFAOYSA-N 0.000 description 1
- RHFZTBSULNJWEI-UHFFFAOYSA-N dimethyl 2-(methoxymethylidene)propanedioate Chemical compound COC=C(C(=O)OC)C(=O)OC RHFZTBSULNJWEI-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- NQBKFULMFQMZBE-UHFFFAOYSA-N n-bz-3-benzanthronylpyrazolanthron Chemical compound C12=CC=CC(C(=O)C=3C4=CC=CC=3)=C2C4=NN1C1=CC=C2C3=C1C1=CC=CC=C1C(=O)C3=CC=C2 NQBKFULMFQMZBE-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride 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
- C07C69/708—Ethers
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)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2426964A DE2426964C3 (de) | 1974-06-04 | 1974-06-04 | Verfahren zur Herstellung von Alkoxymethylenmalonsäuredialkylestern |
| GB2199575A GB1447351A (en) | 1974-06-04 | 1975-05-21 | Process for producing alkoxymethylene malonic acid esters |
| BE156840A BE829650A (fr) | 1974-06-04 | 1975-05-29 | Procede de preparation d'esters alcoxymethylenemaloniques |
| US05/582,474 US4058553A (en) | 1974-06-04 | 1975-05-30 | Method of preparing alkoxymethylenemalonic acid esters |
| CH703375A CH605583A5 (enExample) | 1974-06-04 | 1975-05-30 | |
| FR7517177A FR2273793A1 (fr) | 1974-06-04 | 1975-06-02 | Procede de preparation d'esters alcoxymethylenemaloniques |
| CA229,137A CA1067508A (en) | 1974-06-04 | 1975-06-02 | Process for producing alkoxymethylene malonic acid esters |
| IT49869/75A IT1035921B (it) | 1974-06-04 | 1975-06-03 | Procedimento per la produzione di esteri di acidi alcossi metilen malonici |
| ES438158A ES438158A1 (es) | 1974-06-04 | 1975-06-03 | Procedimiento para la preparacion de esteres de acidos alco-ximetilenmalonicos. |
| JP50066985A JPS514123A (en) | 1974-06-04 | 1975-06-03 | Arukokishimechirenmaronsanesuterunoseiho |
| FI751652A FI63214C (fi) | 1974-06-04 | 1975-06-04 | Foerfarande foer framstaellning av alkoximetylenmalonsyraestrar |
| NLAANVRAGE7506605,A NL187159C (nl) | 1974-06-04 | 1975-06-04 | Werkwijze voor de bereiding van alkoxymethyleenmalonzuurdialkylesters. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2426964A DE2426964C3 (de) | 1974-06-04 | 1974-06-04 | Verfahren zur Herstellung von Alkoxymethylenmalonsäuredialkylestern |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2426964A1 DE2426964A1 (de) | 1975-12-11 |
| DE2426964B2 DE2426964B2 (de) | 1978-10-12 |
| DE2426964C3 true DE2426964C3 (de) | 1979-06-07 |
Family
ID=5917297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2426964A Expired DE2426964C3 (de) | 1974-06-04 | 1974-06-04 | Verfahren zur Herstellung von Alkoxymethylenmalonsäuredialkylestern |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4058553A (enExample) |
| JP (1) | JPS514123A (enExample) |
| BE (1) | BE829650A (enExample) |
| CA (1) | CA1067508A (enExample) |
| CH (1) | CH605583A5 (enExample) |
| DE (1) | DE2426964C3 (enExample) |
| ES (1) | ES438158A1 (enExample) |
| FI (1) | FI63214C (enExample) |
| FR (1) | FR2273793A1 (enExample) |
| GB (1) | GB1447351A (enExample) |
| IT (1) | IT1035921B (enExample) |
| NL (1) | NL187159C (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4277418A (en) | 1976-08-10 | 1981-07-07 | Dynamit Nobel Aktiengesellschaft | Method of preparing alkoxymethylene compounds |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2559147B1 (fr) * | 1984-02-07 | 1986-06-13 | Rhone Poulenc Spec Chim | Procede d'obtention de composes organiques a groupe alkoxyalkylidene |
| FR2566395B1 (fr) * | 1984-06-25 | 1986-11-21 | Rhone Poulenc Spec Chim | Procede d'obtention de composes organiques a groupe alkoxyalkylidene |
| FR2589466B1 (fr) * | 1985-11-04 | 1988-10-14 | Rhone Poulenc Spec Chim | Procede de preparation de composes porteurs de motifs alkoxyalkylidenes |
| DE3927761C2 (de) * | 1989-08-23 | 1997-11-27 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Alkoxyalkylidenmalonsäureestern |
| CN104860818A (zh) * | 2015-04-20 | 2015-08-26 | 浙江新和成股份有限公司 | 一种乙氧基甲叉丙二酸二乙酯的合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3637812A (en) * | 1967-10-02 | 1972-01-25 | Merck & Co Inc | Acylation of reactive organic acid esters |
-
1974
- 1974-06-04 DE DE2426964A patent/DE2426964C3/de not_active Expired
-
1975
- 1975-05-21 GB GB2199575A patent/GB1447351A/en not_active Expired
- 1975-05-29 BE BE156840A patent/BE829650A/xx not_active IP Right Cessation
- 1975-05-30 US US05/582,474 patent/US4058553A/en not_active Expired - Lifetime
- 1975-05-30 CH CH703375A patent/CH605583A5/xx not_active IP Right Cessation
- 1975-06-02 FR FR7517177A patent/FR2273793A1/fr active Granted
- 1975-06-02 CA CA229,137A patent/CA1067508A/en not_active Expired
- 1975-06-03 IT IT49869/75A patent/IT1035921B/it active
- 1975-06-03 JP JP50066985A patent/JPS514123A/ja active Granted
- 1975-06-03 ES ES438158A patent/ES438158A1/es not_active Expired
- 1975-06-04 NL NLAANVRAGE7506605,A patent/NL187159C/xx not_active IP Right Cessation
- 1975-06-04 FI FI751652A patent/FI63214C/fi not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4277418A (en) | 1976-08-10 | 1981-07-07 | Dynamit Nobel Aktiengesellschaft | Method of preparing alkoxymethylene compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| US4058553A (en) | 1977-11-15 |
| FI63214C (fi) | 1983-05-10 |
| FI63214B (fi) | 1983-01-31 |
| BE829650A (fr) | 1975-09-15 |
| CH605583A5 (enExample) | 1978-09-29 |
| DE2426964B2 (de) | 1978-10-12 |
| CA1067508A (en) | 1979-12-04 |
| JPS5735822B2 (enExample) | 1982-07-31 |
| NL7506605A (nl) | 1975-12-08 |
| IT1035921B (it) | 1979-10-20 |
| FR2273793A1 (fr) | 1976-01-02 |
| ES438158A1 (es) | 1977-02-01 |
| NL187159C (nl) | 1991-06-17 |
| FR2273793B1 (enExample) | 1980-05-30 |
| FI751652A7 (enExample) | 1975-12-05 |
| JPS514123A (en) | 1976-01-14 |
| NL187159B (nl) | 1991-01-16 |
| DE2426964A1 (de) | 1975-12-11 |
| GB1447351A (en) | 1976-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HUELS TROISDORF AG, 5210 TROISDORF, DE |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HUELS AG, 4370 MARL, DE |