BE636259A - - Google Patents
Info
- Publication number
- BE636259A BE636259A BE636259DA BE636259A BE 636259 A BE636259 A BE 636259A BE 636259D A BE636259D A BE 636259DA BE 636259 A BE636259 A BE 636259A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- catalysts
- vinyl acetate
- salts
- auccinimide
- Prior art date
Links
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 3
- DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 229910000370 mercury sulfate Inorganic materials 0.000 claims description 2
- 238000006886 vinylation reaction Methods 0.000 claims description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
- 239000012467 final product Substances 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 238000005485 electric heating Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IGDLZDCWMRPMGL-UHFFFAOYSA-N 2-ethenylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C=C)C(=O)C2=C1 IGDLZDCWMRPMGL-UHFFFAOYSA-N 0.000 description 1
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000949473 Correa Species 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- -1 potassium bisulfate Chemical class 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<EMI ID=1.1>
<EMI ID=2.1>
<EMI ID=3.1>
procédèrent ici par analogte aux données du brevet U.S. 2.276.640,
<EMI ID=4.1>
<EMI ID=5.1> <EMI ID=6.1>
<EMI ID=7.1>
sans
étaient / aucun résultat. (Loc oit. page 262).
On a maintenant trouvé que l'on peut préparer la
<EMI ID=8.1>
à partir de la auccinimide ou des produits de substitution de ce composé, et de l'acétate de vinyle, de deux manières
1. Selon le procédé décrit par Joshida (J. Chem. Soc.
<EMI ID=9.1>
p. 10277 b, 1953) on a agité en autoclave, pendant deux heures
<EMI ID=10.1>
'. en présence de KOH (1 Mole - %) et d'un inhibiteur empêchant la polymérisation des dérivés vinyliques. Le produit de réaction a été traité de manière connue en elle-même. On a isolé ainsi en-
<EMI ID=11.1>
<EMI ID=12.1>
Le produit d'addition ainsi préparé se laisse facilement
<EMI ID=13.1>
,1- et ccide acétique. Ici, il faut faire ressortir que le produit
<EMI ID=14.1>
<EMI ID=15.1>
conforme à l'invention. Comme catalyseurs, conviennent les acides
<EMI ID=16.1>
<EMI ID=17.1>
<EMI ID=18.1>
d'aluminium, le chlorure de sine, le fluorure de bore ou d'autres sels de bases faibles et d'acides forts, comme le sulfate de mercure; dans le même sens, sont utilisables les sels acides de bases fortes et d'acides forts, comme le bisulfate de potassium.
<EMI ID=19.1>
nimide peut être effectuée de manière simple, en chauffant le produit de départ avec un des catalyseurs acides mentionnés, dans <EMI ID=20.1> <EMI ID=21.1>
<EMI ID=22.1>
d'addition. alcalins ne modifient pas le comportement du compos' d'addition mentionne, lors du chauffage.
<EMI ID=23.1>
<EMI ID=24.1>
fait que, dans le procédé appartenant au niveau industriel, on , /
<EMI ID=25.1>
<EMI ID=26.1>
<EMI ID=27.1>
<EMI ID=28.1>
<EMI ID=29.1>
<EMI ID=30.1>
<EMI ID=31.1> .h me périodique, avantageusement en présence d'un solvant ou d'un excès d'acétate de vinyle agissant comme solvant. On sépare par <EMI ID=32.1> <EMI ID=33.1>
acétate de vinyle en excès, et l'on traite le résidu par distil-
<EMI ID=34.1> <EMI ID=35.1>
<EMI ID=36.1>
<EMI ID=37.1>
La façon de procéder conformément à l'invention n'est
<EMI ID=38.1>
<EMI ID=39.1>
lise les produite de substitution de ce composé. Ici, aussi bien
<EMI ID=40.1>
<EMI ID=41.1>
des deux formes de réalisation présentées du procédé conforme à l'invention, en les composés N-vinyliques correspondants*
Les exemples suivants illustrent la réalisation d'un nouveau procédé, par lequel on peut arriver par deux moyens,
<EMI ID=42.1>
nimide et de l'acétate de vinyle aux N-vinylauccinimidea correa. ,."" <EMI ID=43.1>
-strictement à ces tomes de réalisation* Naturellement, auaai bien <EMI ID=44.1>
d'addition en question d'une part, que les catalyseurs favorisant la vinylAtion d'autre part, présentent des activités différentes,
<EMI ID=45.1>
<EMI ID=46.1>
respecter dans chaque cas, en ce qui concerne la température de réaction, le rapport des quantités des composants de réaction, 'le milieu réactionnel, les durées de réaction, etc; peuvent être
établies de manière simple en suivant la méthode mentionnée.
Les N-vinylimides préparables selon le procédé décrit,
<EMI ID=47.1>
<EMI ID=48.1>
,aussi bien être polymérisée à eux seuls que copolymérisés avec
dtautres monomères non saturés. Par exemple, les copolymères for- <EMI ID=49.1>
de 1 partie de N-vinylauccinimide sont caractérisés par un point
<EMI ID=50.1>
te de méthyle pur.
<EMI ID=51.1>
<EMI ID=52.1>
mécanique et d'un système de chauffage électrique, on chauffe
<EMI ID=53.1>
<EMI ID=54.1>
<EMI ID=55.1>
de 5 atm. Après refroidissements on sépare le catalyseur par filtration et l'on sépare par distillation à la pression normale, '
<EMI ID=56.1>
<EMI ID=57.1>
<EMI ID=58.1>
<EMI ID=59.1>
<EMI ID=60.1>
<EMI ID=61.1>
<EMI ID=62.1>
<EMI ID=63.1>
<EMI ID=64.1>
<EMI ID=65.1>
<EMI ID=66.1>
<EMI ID=67.1>
<EMI ID=68.1>
<EMI ID=69.1>
<EMI ID=70.1>
<EMI ID=71.1>
<EMI ID=72.1>
ainsi une pression de 6 atm. En traitant comme dans l'exemple 1,
<EMI ID=73.1>
<EMI ID=74.1>
On dissout le résidu de distillation dans l'alcool chaud et après addition de terre décolorante, on filtre la solution.
<EMI ID=75.1>
<EMI ID=76.1>
<EMI ID=77.1>
<EMI ID=78.1>
canique et d'un système de chauffage électrique, on chauffe
<EMI ID=79.1>
d'acétate de vinyle et 8 g de sulfate de cuivre II, avec 0,2 g
<EMI ID=80.1>
<EMI ID=81.1>
clave Le résidu de filtration est constitué du sulfate de cuivre
<EMI ID=82.1>
<EMI ID=83.1>
<EMI ID=84.1>
<EMI ID=85.1>
<EMI ID=86.1>
théorie) de N-vinylphtalimide. On peut recristalliser celle-ci
<EMI ID=87.1>
<EMI ID=88.1>
<EMI ID=89.1>
<EMI ID=90.1>
<EMI ID=91.1>
<EMI ID=92.1>
<EMI ID=93.1>
stabilisateur. Dans le vide de la trempe 1 eau, pratiquement tout le contenu du ballon distille à une température de 135 a 170*C.
<EMI ID = 1.1>
<EMI ID = 2.1>
<EMI ID = 3.1>
proceeded here by analogy to the data of U.S. Patent 2,276,640,
<EMI ID = 4.1>
<EMI ID = 5.1> <EMI ID = 6.1>
<EMI ID = 7.1>
without
were / no results. (Loc oit. Page 262).
We have now found that we can prepare the
<EMI ID = 8.1>
from auccinimide or substitutes thereof, and vinyl acetate, in two ways
1. According to the method described by Joshida (J. Chem. Soc.
<EMI ID = 9.1>
p. 10277 b, 1953) was stirred in an autoclave for two hours
<EMI ID = 10.1>
'. in the presence of KOH (1 Mole -%) and of an inhibitor preventing the polymerization of vinyl derivatives. The reaction product was processed in a manner known per se. We have thus isolated in-
<EMI ID = 11.1>
<EMI ID = 12.1>
The adduct thus prepared can easily be
<EMI ID = 13.1>
, 1- and acetic acid. Here, it must be emphasized that the product
<EMI ID = 14.1>
<EMI ID = 15.1>
according to the invention. Suitable catalysts are acids
<EMI ID = 16.1>
<EMI ID = 17.1>
<EMI ID = 18.1>
aluminum, sine chloride, boron fluoride or other salts of weak bases and strong acids, such as mercury sulfate; in the same sense, the acid salts of strong bases and strong acids, such as potassium bisulfate, can be used.
<EMI ID = 19.1>
nimide can be carried out in a simple way, by heating the starting material with one of the acid catalysts mentioned, in <EMI ID = 20.1> <EMI ID = 21.1>
<EMI ID = 22.1>
addition. alkalis do not modify the behavior of the mentioned additive on heating.
<EMI ID = 23.1>
<EMI ID = 24.1>
that, in the process belonging to the industrial level, we, /
<EMI ID = 25.1>
<EMI ID = 26.1>
<EMI ID = 27.1>
<EMI ID = 28.1>
<EMI ID = 29.1>
<EMI ID = 30.1>
<EMI ID = 31.1> .h me periodic, advantageously in the presence of a solvent or an excess of vinyl acetate acting as a solvent. We separate by <EMI ID = 32.1> <EMI ID = 33.1>
excess vinyl acetate, and the residue is treated by distilling
<EMI ID = 34.1> <EMI ID = 35.1>
<EMI ID = 36.1>
<EMI ID = 37.1>
The way of proceeding according to the invention is not
<EMI ID = 38.1>
<EMI ID = 39.1>
read the substitution products of this compound. Here as well
<EMI ID = 40.1>
<EMI ID = 41.1>
of the two embodiments presented of the process according to the invention, in the corresponding N-vinyl compounds *
The following examples illustrate the realization of a new process, by which one can arrive by two means,
<EMI ID = 42.1>
nimide and vinyl acetate to N-vinylauccinimidea correa. ,. "" <EMI ID = 43.1>
-strictly to these tomes of achievement * Naturally, auaai well <EMI ID = 44.1>
of addition in question on the one hand, that the catalysts promoting vinylAtion on the other hand, have different activities,
<EMI ID = 45.1>
<EMI ID = 46.1>
respect in each case, with regard to the reaction temperature, the ratio of the quantities of the reaction components, the reaction medium, the reaction times, etc; can be
established in a simple way by following the method mentioned.
N-vinylimides which can be prepared according to the method described,
<EMI ID = 47.1>
<EMI ID = 48.1>
, both be polymerized on their own and copolymerized with
other unsaturated monomers. For example, the copolymers for- <EMI ID = 49.1>
of 1 part of N-vinylauccinimide are characterized by a dot
<EMI ID = 50.1>
of pure methyl.
<EMI ID = 51.1>
<EMI ID = 52.1>
mechanical and an electric heating system, we heat
<EMI ID = 53.1>
<EMI ID = 54.1>
<EMI ID = 55.1>
of 5 atm. After cooling, the catalyst is filtered off and the mixture is distilled off at normal pressure, '
<EMI ID = 56.1>
<EMI ID = 57.1>
<EMI ID = 58.1>
<EMI ID = 59.1>
<EMI ID = 60.1>
<EMI ID = 61.1>
<EMI ID = 62.1>
<EMI ID = 63.1>
<EMI ID = 64.1>
<EMI ID = 65.1>
<EMI ID = 66.1>
<EMI ID = 67.1>
<EMI ID = 68.1>
<EMI ID = 69.1>
<EMI ID = 70.1>
<EMI ID = 71.1>
<EMI ID = 72.1>
thus a pressure of 6 atm. By treating as in example 1,
<EMI ID = 73.1>
<EMI ID = 74.1>
The distillation residue is dissolved in hot alcohol and after addition of bleaching earth, the solution is filtered.
<EMI ID = 75.1>
<EMI ID = 76.1>
<EMI ID = 77.1>
<EMI ID = 78.1>
canique and an electric heating system, we heat
<EMI ID = 79.1>
vinyl acetate and 8 g of copper II sulfate, with 0.2 g
<EMI ID = 80.1>
<EMI ID = 81.1>
clave The filter residue consists of copper sulphate
<EMI ID = 82.1>
<EMI ID = 83.1>
<EMI ID = 84.1>
<EMI ID = 85.1>
<EMI ID = 86.1>
theory) of N-vinylphthalimide. We can recrystallize it
<EMI ID = 87.1>
<EMI ID = 88.1>
<EMI ID = 89.1>
<EMI ID = 90.1>
<EMI ID = 91.1>
<EMI ID = 92.1>
<EMI ID = 93.1>
stabilizer. In the vacuum of the 1-water quench, virtually the entire contents of the flask distilled at a temperature of 135 to 170 ° C.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR940088A FR1361270A (en) | 1963-07-02 | 1963-07-02 | Process for preparing n-vinylimides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE636259A true BE636259A (en) |
Family
ID=8807398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE636259D BE636259A (en) | 1963-07-02 |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE636259A (en) |
| FR (1) | FR1361270A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3207031A1 (en) * | 1982-02-26 | 1983-09-08 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING CYCLIC N-VINYLACYLAMINES |
| US8884052B2 (en) | 2011-12-15 | 2014-11-11 | Celanese International Corporation | Production of diacetoxyethylene by direct acetoxylation |
-
0
- BE BE636259D patent/BE636259A/fr unknown
-
1963
- 1963-07-02 FR FR940088A patent/FR1361270A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1361270A (en) | 1964-05-15 |
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