DE134980C - - Google Patents
Info
- Publication number
- DE134980C DE134980C DENDAT134980D DE134980DA DE134980C DE 134980 C DE134980 C DE 134980C DE NDAT134980 D DENDAT134980 D DE NDAT134980D DE 134980D A DE134980D A DE 134980DA DE 134980 C DE134980 C DE 134980C
- Authority
- DE
- Germany
- Prior art keywords
- dimethyl ether
- parts
- june
- alcohol
- melting
- 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.)
- Active
Links
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
- MNSGOOCAMMSKGI-UHFFFAOYSA-N N-(hydroxymethyl)phthalimide Chemical compound C1=CC=C2C(=O)N(CO)C(=O)C2=C1 MNSGOOCAMMSKGI-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- RCNVWPZXBAGJQE-UHFFFAOYSA-N 4-benzylisoindole-1,3-dione Chemical class O=C1NC(=O)C2=C1C=CC=C2CC1=CC=CC=C1 RCNVWPZXBAGJQE-UHFFFAOYSA-N 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-Nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-Nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
ΛΙ 134980 KLASSE 12 o. ΛΙ 134980 CLASS 12 o.
Zusatz zum Patente 134979 vom 2. Juni 1901.Addendum to patent 134979 of June 2, 1901.
Patentirt im Deutschen Reiche vom 23. Juni 1901 ab. Längste Dauer: 1. Juni 1916.Patented in the German Empire on June 23, 1901. Longest duration: June 1, 1916.
In der Beschreibung des Patents 134979 wurde ein Verfahren zur Darstellung von Benzylphtalimidderivaten beschrieben, darin bestehend, dafs man Oxymethylphtalimid mit aromatischen Verbindungen bei Gegenwart von Schwefelsäure condensirt.In the specification of the patent 134979 a method for the representation of Benzylphtalimidderivaten described, consisting in that one oxymethylphtalimid with aromatic compounds condensed in the presence of sulfuric acid.
Es wurde nun gefunden, dafs an Stelle des Oxymethylphtalimids der Diphtalimid-dimethyläther — welcher schon in den Berichten XXXI (1898) S. 1232 beschrieben ist, und welcher auch aus dem Oxymethyphtalimid bei Einwirkung von concentrirter Schwefelsäure entsteht — verwendet werden kann.It has now been found that instead of oxymethylphthalimide, diphtalimide dimethyl ether - which is already described in Reports XXXI (1898) p. 1232, and which also arises from the oxymethyphthalimide on the action of concentrated sulfuric acid - can be used.
Das Verfahren ist im Wesentlichen dasselbe wie dasjenige des Hauptpatents, wie folgende Beispiele näher erläutern:The procedure is essentially the same as that of the main patent as follows Explain examples in more detail:
Man löst 94 Th. Phenol in einem abgekühlten Gemisch von 650 Th. Schwefelsäure (1,84 spec. Gew.) und 130 Th. Wasser, setzt 168 Th. Diphtalimid-dimethyläther hinzu, rührt energisch, läfst dann einige Zeit stehen, bis die Masse fest geworden und trägt unter Kühlung in Wasser ein. Aus dem abfiltrirten getrockneten Condensationsprodukt gewinnt man durch Auskochen mit Alkohol und Umlösen des Rückstandes aus siedendem Nitrobenzol ein bei 2950 schmelzendes Oxyxylylendiphtalimid: 94 parts of phenol are dissolved in a cooled mixture of 650 parts of sulfuric acid (1.84 spec. Weight) and 130 parts of water, 168 parts of diphtalimide dimethyl ether are added, the mixture is stirred vigorously, and then left to stand for some time The mass has solidified and enters water with cooling. From the filtrate dried Condensationsprodukt is obtained by boiling with alcohol and redissolution of the residue from boiling nitrobenzene at 295 0 melting Oxyxylylendiphtalimid:
CO-CO-
Im Alkohol finden sich zwei Oxybenzylphtalimide There are two oxybenzylphthalimides in alcohol
eines schwerer löslich bei 2050 schmelzend und ein leichter lösliches gegen 1500 schmelzend. a less soluble melting at 205 0 melting and an easy-soluble against 150 0th
Durch Condensation des Diphtalimid - dimethyläthers mit p-Nitrophenol erhält man ein einheitliches Condensationsprodukt, das aus Alkohol und Eisessig krystallisirt bei 233 bis 2340 schmilzt.By the condensation of Diphtalimid - dimethyl ether with p-nitrophenol gives a uniform Condensationsprodukt which crystallizes from alcohol and glacial acetic acid at 233-234 0 melts.
Diphtalimid-dimethyläther mit o-Nitrotoluol condensirt liefert das schon in der Beschreibung des Hauptpatents beschriebene Nitrotolylmethylphtalimid, das bei 155 bis 1560 schmilzt.Diphtalimid dimethyl ether with orthonitrotoluene condensed delivers the Nitrotolylmethylphtalimid already described in the description of the main patent, which melts at 155-156 0th
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE134980C true DE134980C (en) |
Family
ID=403056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT134980D Active DE134980C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE134980C (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2519244A1 (en) * | 1975-04-30 | 1976-11-11 | Bayer Ag | METHOD OF MANUFACTURING ANION EXCHANGERS |
| US5566803A (en) * | 1994-05-13 | 1996-10-22 | Fichtel & Sachs Ag | Clutch assembly for a motor vehicle having a flexible clutch disc |
| US6846241B2 (en) | 2002-03-15 | 2005-01-25 | Centa-Antriebe Kirschey Gmbh | One-piece coupling disk |
| AU2014224080B2 (en) * | 2007-05-10 | 2016-02-25 | Plastipak Packaging, Inc. | Oxygen scavenging molecules, articles containing same, and methods of their use. |
| US9896554B2 (en) | 2009-09-29 | 2018-02-20 | Plastipak Packaging, Inc. | Colorant compatible oxygen scavenging polymer compositions and articles made from same |
| US10040922B2 (en) | 2009-11-13 | 2018-08-07 | Plastipak Packaging, Inc. | Oxygen scavengers, compositions comprising the scavengers, and articles made from the compositions |
| US10059666B2 (en) | 2009-11-13 | 2018-08-28 | Plastipak Packaging, Inc. | Oxygen scavengers, compositions comprising the scavengers, and articles made from the compositions |
-
0
- DE DENDAT134980D patent/DE134980C/de active Active
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2519244A1 (en) * | 1975-04-30 | 1976-11-11 | Bayer Ag | METHOD OF MANUFACTURING ANION EXCHANGERS |
| US5566803A (en) * | 1994-05-13 | 1996-10-22 | Fichtel & Sachs Ag | Clutch assembly for a motor vehicle having a flexible clutch disc |
| US6846241B2 (en) | 2002-03-15 | 2005-01-25 | Centa-Antriebe Kirschey Gmbh | One-piece coupling disk |
| AU2014224080B2 (en) * | 2007-05-10 | 2016-02-25 | Plastipak Packaging, Inc. | Oxygen scavenging molecules, articles containing same, and methods of their use. |
| EP2754690B1 (en) * | 2007-05-10 | 2017-12-13 | Plastipak Packaging, Inc. | Oxygen scavenging molecules, articles containing same, and methods of their use |
| US10125096B2 (en) | 2007-05-10 | 2018-11-13 | Plastipak Packaging, Inc. | Oxygen scavenging molecules, articles containing same, and methods of their use |
| US10906870B2 (en) | 2007-05-10 | 2021-02-02 | Plastipak Packaging, Inc. | Oxygen scavenging molecules, articles containing same, and methods of their use |
| US11739059B2 (en) | 2007-05-10 | 2023-08-29 | Plastipak Packaging, Inc. | Oxygen scavenging molecules, articles containing same, and methods of their use |
| US9896554B2 (en) | 2009-09-29 | 2018-02-20 | Plastipak Packaging, Inc. | Colorant compatible oxygen scavenging polymer compositions and articles made from same |
| US10040922B2 (en) | 2009-11-13 | 2018-08-07 | Plastipak Packaging, Inc. | Oxygen scavengers, compositions comprising the scavengers, and articles made from the compositions |
| US10059666B2 (en) | 2009-11-13 | 2018-08-28 | Plastipak Packaging, Inc. | Oxygen scavengers, compositions comprising the scavengers, and articles made from the compositions |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE134980C (en) | ||
| DE2624153A1 (en) | CONTRAST AGENTS FOR X-RAY PHOTOS | |
| DE511468C (en) | Process for the preparation of 5-chloro-2-amino-1-methoxybenzene | |
| AT144369B (en) | Process for the production of malleable and hardenable condensation products and of synthetic masses from them. | |
| DE40747C (en) | Process for the preparation of ketonic acid esters and ketoketones by the action of two acid esters on one another or of acid esters on ketones in the presence of sodium alkoxides | |
| DE1643329A1 (en) | Process for the preparation of nitroaminodiarylaethers | |
| DE282267C (en) | ||
| DE615471C (en) | Process for the preparation of basic derivatives of benzodioxane | |
| DE42276C (en) | Process for the preparation of γ-oxyquinoline derivatives by heating aromatic / 9-amidocrotonic acid esters or aromatic γ-amido / 9-phenylakrylic acid esters | |
| DE69327C (en) | Process for the preparation of β-cymidine from the oximes of camphor rats of the formula C0H16O, which are methyl ketones | |
| DE217557C (en) | ||
| AT142910B (en) | Process for the preparation of basic dioxane derivatives. | |
| DE160103C (en) | ||
| DE105199C (en) | ||
| DE613215C (en) | Process for the preparation of 3,5-dialkoxyphenylamino alcohols | |
| DE115334C (en) | ||
| DE204764C (en) | ||
| DE679279C (en) | Process for the preparation of a tetraalkylated dinitrobenzene | |
| DE97710C (en) | ||
| DE225132C (en) | ||
| DE134979C (en) | PROCESS FOR PREPARATION OF BENZYLPHTALIMIDES | |
| DE105797C (en) | ||
| DE515540C (en) | Process for the preparation of diacidyl derivatives of meta-xylene | |
| DE120864C (en) | ||
| DE89244C (en) |