DE2645477C2 - Verfahren zur Herstellung von Orthoessigsäurealkylestern - Google Patents
Verfahren zur Herstellung von OrthoessigsäurealkylesternInfo
- Publication number
- DE2645477C2 DE2645477C2 DE2645477A DE2645477A DE2645477C2 DE 2645477 C2 DE2645477 C2 DE 2645477C2 DE 2645477 A DE2645477 A DE 2645477A DE 2645477 A DE2645477 A DE 2645477A DE 2645477 C2 DE2645477 C2 DE 2645477C2
- Authority
- DE
- Germany
- Prior art keywords
- alcoholysis
- reaction
- acetonitrile
- organic solvent
- distillation
- 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
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 238000006136 alcoholysis reaction Methods 0.000 claims description 19
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- -1 imidoester hydrochloride Chemical class 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 9
- 235000019270 ammonium chloride Nutrition 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 4
- CEQFOVLGLXCDCX-WUKNDPDISA-N methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 description 4
- 229940078552 o-xylene Drugs 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 2
- 101710134784 Agnoprotein Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000002905 orthoesters Chemical class 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 201000009482 yaws Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/60—Preparation of compounds having groups or groups
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 (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2645477A DE2645477C2 (de) | 1976-10-08 | 1976-10-08 | Verfahren zur Herstellung von Orthoessigsäurealkylestern |
| IT51304/77A IT1112095B (it) | 1976-10-08 | 1977-10-06 | Procedimento per la produzione di ortoacetati alchilici |
| FR7730155A FR2367041A1 (fr) | 1976-10-08 | 1977-10-06 | Procede de fabrication d'orthoacetates d'alcoyle |
| US05/840,186 US4182910A (en) | 1976-10-08 | 1977-10-06 | Method of preparing orthoacetic acid alkyl esters |
| GB41737/77A GB1550775A (en) | 1976-10-08 | 1977-10-07 | Process for producing ortheacetic acid alkyl esters |
| DK446277A DK446277A (da) | 1976-10-08 | 1977-10-07 | Fremgangsmaade til fremstilling af orthoeddikesyrealkylestere |
| JP12080177A JPS5346911A (en) | 1976-10-08 | 1977-10-07 | Method of manufacturing alkyl orthoacetate |
| BE181536A BE859479A (fr) | 1976-10-08 | 1977-10-07 | Procede de fabrication d'orthoacetates d'alcoyle |
| CH1230977A CH630331A5 (de) | 1976-10-08 | 1977-10-07 | Verfahren zur herstellung von orthoessigsaeurealkylestern. |
| NL7711044A NL7711044A (nl) | 1976-10-08 | 1977-10-07 | Werkwijze voor het bereiden van orthoazijnzuur- alkylester. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2645477A DE2645477C2 (de) | 1976-10-08 | 1976-10-08 | Verfahren zur Herstellung von Orthoessigsäurealkylestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2645477A1 DE2645477A1 (de) | 1978-04-13 |
| DE2645477C2 true DE2645477C2 (de) | 1982-03-04 |
Family
ID=5990021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2645477A Expired DE2645477C2 (de) | 1976-10-08 | 1976-10-08 | Verfahren zur Herstellung von Orthoessigsäurealkylestern |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4182910A (en:Method) |
| JP (1) | JPS5346911A (en:Method) |
| BE (1) | BE859479A (en:Method) |
| CH (1) | CH630331A5 (en:Method) |
| DE (1) | DE2645477C2 (en:Method) |
| DK (1) | DK446277A (en:Method) |
| FR (1) | FR2367041A1 (en:Method) |
| GB (1) | GB1550775A (en:Method) |
| IT (1) | IT1112095B (en:Method) |
| NL (1) | NL7711044A (en:Method) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1209431B (it) * | 1980-11-28 | 1989-07-16 | Angeli Inst Spa | Imidazolilfenil amidine, processi per la loro preparazione e loro impiego farmaceutico, ed intermedi di preparazione. |
| US5268008A (en) * | 1982-12-27 | 1993-12-07 | Union Oil Company Of California | Hydrocarbon fuel composition |
| US4748280A (en) * | 1985-11-07 | 1988-05-31 | Pfizer Inc. | Certain chlorination process for preparing 2-chloro-1,1,1-(C1 -C6) |
| US5290325A (en) * | 1990-02-28 | 1994-03-01 | Union Oil Company Of California | Hydrocarbon fuel composition containing alpha-ketocarboxylate additive |
| US5401885A (en) * | 1993-06-01 | 1995-03-28 | Huls America, Inc. | Method of preparing ortho esters and 1.1-dialkoxycycloalkanes |
| TWI417297B (zh) * | 2007-04-11 | 2013-12-01 | Daiichi Sankyo Co Ltd | 神經胺酸衍生物及其製造方法 |
| CN102924244A (zh) * | 2012-11-02 | 2013-02-13 | 南通天泽化工有限公司 | 一种高品质原乙酸三甲酯的生产工艺 |
| CN102924245A (zh) * | 2012-11-02 | 2013-02-13 | 南通天泽化工有限公司 | 一种原乙酸三甲酯的醇解工艺 |
| CN103483165B (zh) * | 2013-09-25 | 2016-02-24 | 河北诚信有限责任公司 | 制备原甲酸酯的绿色清洁工艺 |
| CN104072346A (zh) * | 2014-06-19 | 2014-10-01 | 常州吉恩化工有限公司 | 一种原酸酯类化合物的制备方法 |
| CN114605234B (zh) * | 2020-12-09 | 2023-12-26 | 南通天泽化工有限公司 | 一种原乙酸三甲酯的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD28942A (en:Method) * | ||||
| GB637757A (en) * | 1946-12-21 | 1950-05-24 | Gen Aniline & Film Corp | Process for preparation of orthoformic esters |
| US2527494A (en) * | 1946-12-21 | 1950-10-24 | Gen Aniline & Film Corp | Process for preparation of orthoformic esters |
| SU105467A1 (ru) * | 1956-01-02 | 1956-11-30 | В.И. Зарецкий | Способ получени эфиров ортокарбоновых кислот |
| GB853405A (en) * | 1958-04-18 | 1960-11-09 | Lonza Electric & Chem Works | Improvements in or relating to the production of orthoformic acid esters |
| DE1126854B (de) * | 1958-04-18 | 1962-04-05 | Lonza Ag | Verfahren zur Herstellung von Orthoameisensaeureestern |
| AT291958B (de) * | 1968-12-03 | 1971-08-10 | Knapsack Ag | Verfahren zur Herstellung von Orthoameisensäurealkylestern |
-
1976
- 1976-10-08 DE DE2645477A patent/DE2645477C2/de not_active Expired
-
1977
- 1977-10-06 IT IT51304/77A patent/IT1112095B/it active
- 1977-10-06 US US05/840,186 patent/US4182910A/en not_active Expired - Lifetime
- 1977-10-06 FR FR7730155A patent/FR2367041A1/fr active Granted
- 1977-10-07 DK DK446277A patent/DK446277A/da not_active Application Discontinuation
- 1977-10-07 CH CH1230977A patent/CH630331A5/de not_active IP Right Cessation
- 1977-10-07 NL NL7711044A patent/NL7711044A/xx not_active Application Discontinuation
- 1977-10-07 GB GB41737/77A patent/GB1550775A/en not_active Expired
- 1977-10-07 JP JP12080177A patent/JPS5346911A/ja active Pending
- 1977-10-07 BE BE181536A patent/BE859479A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1112095B (it) | 1986-01-13 |
| DK446277A (da) | 1978-04-09 |
| US4182910A (en) | 1980-01-08 |
| JPS5346911A (en) | 1978-04-27 |
| NL7711044A (nl) | 1978-04-11 |
| FR2367041B1 (en:Method) | 1984-10-19 |
| GB1550775A (en) | 1979-08-22 |
| BE859479A (fr) | 1978-02-01 |
| FR2367041A1 (fr) | 1978-05-05 |
| DE2645477A1 (de) | 1978-04-13 |
| CH630331A5 (de) | 1982-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |