PL89720B1 - - Google Patents
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- Publication number
- PL89720B1 PL89720B1 PL1972158663A PL15866372A PL89720B1 PL 89720 B1 PL89720 B1 PL 89720B1 PL 1972158663 A PL1972158663 A PL 1972158663A PL 15866372 A PL15866372 A PL 15866372A PL 89720 B1 PL89720 B1 PL 89720B1
- Authority
- PL
- Poland
- Prior art keywords
- reactor
- reaction
- general formula
- aldehyde
- components
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 31
- 150000003254 radicals Chemical class 0.000 claims description 16
- 239000003999 initiator Substances 0.000 claims description 13
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 11
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 10
- -1 alkyl radicals Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 description 19
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
- 238000004821 distillation Methods 0.000 description 8
- 238000009835 boiling Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001451 organic peroxides Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 210000003411 telomere Anatomy 0.000 description 4
- 102000055501 telomere Human genes 0.000 description 4
- 108091035539 telomere Proteins 0.000 description 4
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 3
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- BOOBDAVNHSOIDB-UHFFFAOYSA-N (2,3-dichlorobenzoyl) 2,3-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC=CC(C(=O)OOC(=O)C=2C(=C(Cl)C=CC=2)Cl)=C1Cl BOOBDAVNHSOIDB-UHFFFAOYSA-N 0.000 description 1
- YIXSKDRXJTZCHT-UHFFFAOYSA-N 2-acetylbutanedioic acid Chemical class CC(=O)C(C(O)=O)CC(O)=O YIXSKDRXJTZCHT-UHFFFAOYSA-N 0.000 description 1
- XIBPCLQLEGQADN-UHFFFAOYSA-N 4-acetyloxy-4-oxobutanoic acid Chemical compound CC(=O)OC(=O)CCC(O)=O XIBPCLQLEGQADN-UHFFFAOYSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- CHRYLDPDKMOXCJ-UHFFFAOYSA-N dibutyl 2-acetylbutanedioate Chemical compound CCCCOC(=O)CC(C(C)=O)C(=O)OCCCC CHRYLDPDKMOXCJ-UHFFFAOYSA-N 0.000 description 1
- DVSDDICSXBCMQJ-UHFFFAOYSA-N diethyl 2-acetylbutanedioate Chemical compound CCOC(=O)CC(C(C)=O)C(=O)OCC DVSDDICSXBCMQJ-UHFFFAOYSA-N 0.000 description 1
- CZWWKAPYGDDMPF-UHFFFAOYSA-N diethyl 2-butanoylbutanedioate Chemical compound CCCC(=O)C(C(=O)OCC)CC(=O)OCC CZWWKAPYGDDMPF-UHFFFAOYSA-N 0.000 description 1
- XREKLQOUFWBSFH-UHFFFAOYSA-N dimethyl 2-acetylbutanedioate Chemical compound COC(=O)CC(C(C)=O)C(=O)OC XREKLQOUFWBSFH-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical class OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 description 1
- 150000004727 oxaloacetic acid derivatives Chemical class 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- UAKCMIIOSJFOTD-UHFFFAOYSA-M sodium;3-oxobutanoate Chemical compound [Na+].CC(=O)CC([O-])=O UAKCMIIOSJFOTD-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 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
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2155360A DE2155360C3 (de) | 1971-11-08 | 1971-11-08 | Verfahren zur Herstellung von Acylbernsteinsäuredialkylestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL89720B1 true PL89720B1 (enExample) | 1976-12-31 |
Family
ID=5824486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972158663A PL89720B1 (enExample) | 1971-11-08 | 1972-11-06 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3786083A (enExample) |
| JP (1) | JPS5742620B2 (enExample) |
| BR (1) | BR7207778D0 (enExample) |
| CH (1) | CH569687A5 (enExample) |
| CS (1) | CS163289B2 (enExample) |
| DD (1) | DD100458A5 (enExample) |
| DE (1) | DE2155360C3 (enExample) |
| FR (1) | FR2159357B1 (enExample) |
| GB (1) | GB1348589A (enExample) |
| IT (1) | IT1033066B (enExample) |
| PL (1) | PL89720B1 (enExample) |
| SU (1) | SU499800A3 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GEP20094751B (en) * | 2004-08-18 | 2009-08-10 | Pfizer | Inhibitors of hepatitis c virus rna-dependent rna polymerase, and compositions and treatments using the same |
| CN105085263B (zh) * | 2015-08-19 | 2017-01-11 | 迈克斯(如东)化工有限公司 | 一种2-烷酰基甲基-1,4-丁二酸衍生物的制备方法及其中间体 |
| CN105085270B (zh) * | 2015-08-19 | 2017-01-11 | 迈克斯(如东)化工有限公司 | 一种抗倒酯及其中间体的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2577133A (en) * | 1947-03-13 | 1951-12-04 | Us Rubber Co | Preparation of keto-carboxylic acids and their derivatives |
| US2647918A (en) * | 1950-06-23 | 1953-08-04 | Monsanto Chemicals | Saturated carbocyclic oxoesters and process for their preparation |
-
1971
- 1971-11-08 DE DE2155360A patent/DE2155360C3/de not_active Expired
-
1972
- 1972-11-03 US US00303491A patent/US3786083A/en not_active Expired - Lifetime
- 1972-11-04 SU SU1843568A patent/SU499800A3/ru active
- 1972-11-06 PL PL1972158663A patent/PL89720B1/pl unknown
- 1972-11-06 DD DD166692A patent/DD100458A5/xx unknown
- 1972-11-07 BR BR007778/72A patent/BR7207778D0/pt unknown
- 1972-11-07 CH CH1619872A patent/CH569687A5/xx not_active IP Right Cessation
- 1972-11-07 IT IT31355/72A patent/IT1033066B/it active
- 1972-11-07 JP JP47110840A patent/JPS5742620B2/ja not_active Expired
- 1972-11-08 CS CS7549A patent/CS163289B2/cs unknown
- 1972-11-08 FR FR7239477A patent/FR2159357B1/fr not_active Expired
- 1972-11-08 GB GB5155172A patent/GB1348589A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5742620B2 (enExample) | 1982-09-09 |
| JPS4861422A (enExample) | 1973-08-28 |
| BR7207778D0 (pt) | 1973-08-23 |
| SU499800A3 (ru) | 1976-01-15 |
| DE2155360C3 (de) | 1980-04-03 |
| FR2159357A1 (enExample) | 1973-06-22 |
| GB1348589A (en) | 1974-03-20 |
| FR2159357B1 (enExample) | 1977-12-23 |
| CS163289B2 (enExample) | 1975-08-29 |
| IT1033066B (it) | 1979-07-10 |
| DD100458A5 (enExample) | 1973-09-20 |
| US3786083A (en) | 1974-01-15 |
| DE2155360B2 (de) | 1979-08-02 |
| CH569687A5 (enExample) | 1975-11-28 |
| DE2155360A1 (de) | 1973-05-17 |
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