DE1031788B - Process for the production of pure 4, 4-dioxydiphenyl-cyclohexane - Google Patents
Process for the production of pure 4, 4-dioxydiphenyl-cyclohexaneInfo
- Publication number
- DE1031788B DE1031788B DEF22890A DEF0022890A DE1031788B DE 1031788 B DE1031788 B DE 1031788B DE F22890 A DEF22890 A DE F22890A DE F0022890 A DEF0022890 A DE F0022890A DE 1031788 B DE1031788 B DE 1031788B
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- dioxydiphenylcyclohexane
- pure
- dioxydiphenyl
- cyclohexane
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000007700 distillative separation Methods 0.000 claims description 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 239000013078 crystal Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
Gegenstand der Patentanmeldung F 19036 IVb/12q ist ein Verfahren zur Herstellung von reinen 4,4'-Dioxydiphenylalkanen aus denAddükten der 4,4'-Dioxydiphenylalkane mit Phenol, das darin besteht, daß man die 4,4'-Dioxydiphenylalkane in wasserhaltigem Phenol in der Wärme löst, die Lösung abkühlt, die sich in kristallisierter Form abgeschiedenen Addukte aus 4,4'-Dioxydiphenylalkanen und Phenol abtrennt und aus diesen die 4,4'-Dioxydiphenylalkane in an sich bekannter Weise durch extraktive oder destillative Abtrennung des gebundenen Phenols isoliert.The subject of patent application F 19036 IVb / 12q is a process for the preparation of pure 4,4'-dioxydiphenylalkanes from the adducts of 4,4'-dioxydiphenylalkanes with phenol, which consists of the 4,4'-dioxydiphenylalkanes in water-containing Phenol dissolves in the heat, the solution cools, the adducts deposited in crystallized form separates from 4,4'-dioxydiphenylalkanes and phenol and from these the 4,4'-dioxydiphenylalkanes in an isolated in a known manner by extractive or distillative separation of the bound phenol.
Es wurde nun gefunden, daß sich in gleicher Weise auch 4,4'-Dioxydiphenylcyclohexan in reiner Form gewinnen läßt. Dieses Verfahren entspricht völlig dem Verfahren zur Herstellung reiner 4,4'-Dioxydiphenylalkane gemäß Patentanmeldung F19O36IVb/12q.It has now been found that 4,4'-dioxydiphenylcyclohexane is also pure in the same way Lets gain form. This procedure corresponds completely to the procedure for the production of pure 4,4'-Dioxydiphenylalkanes according to patent application F19O36IVb / 12q.
Eine Lösung von 400 kg Phenol und 78 kg Cyclohexanon wird auf 10° C abgekühlt und anschließend mit 80 kg 38°/oiger wäßriger Salzsäure vermischt. Nach 15 bis 20 Stunden ist die Mischung unter Selbsterwärmung auf 65° C zu einem Kristallbrei erstarrt. Sie wird noch weitere 6 Tage stehengelassen. Dieses wird durch Einblasen von Wasserdampf und Zugabe von etwa 60 kg 5O°/oiger Natronlauge unter Umrühren aufgeschmolzen und neutralisiert, wonach sich eine wäßrige Kochsalzlösung unten abscheidet, welche abgetrennt wird. Die obere organische Schicht wird mit etwa 500 1 90° C heißem Wasser durchgerührt und die dann unten sich abscheidende organische Schicht filtriert und abgekühlt. Aus dem dadurch entstandenen Kristallbrei erhält man durch Abschleudern 252 kg Mischkristalle und 25O1 kg wäßriges Phenol. Aus den Mischkristallen werden durch Destillation 50,4 kg Phenol erhalten, wobei 176 kg reines 4,4/-Dioxydiphenyl-l,l-cyclohexan (Ausbeute: 82,2% der Theorie, Schmelzpunkt 186° C) im Rückstand bleiben. Aus der Phenol-Mutterlauge werden durch Destillation 175,8 kg Phenol und im Rückstand 16,4 kg harzhaltiges Bisphenol gewonnen. Aus den verschiedenen Waschwässern werden durch Extraktion 35,8 kg Phenol zurückerhalten.A solution of 400 kg of phenol and 78 kg of cyclohexanone is cooled to 10 ° C. and then mixed with 80 kg of 38% aqueous hydrochloric acid. After 15 to 20 hours, the mixture has solidified to form a crystal paste with self-heating to 65 ° C. It is left to stand for another 6 days. This is melted and neutralized by blowing in steam and adding about 60 kg of 50% sodium hydroxide solution while stirring, after which an aqueous sodium chloride solution separates out at the bottom and is separated off. The upper organic layer is stirred through with about 500-190 ° C. hot water and the organic layer which then separates out is filtered and cooled. 252 kg of mixed crystals and 250 1 kg of aqueous phenol are obtained from the resulting crystal slurry by spinning off. 50.4 kg of phenol are obtained from the mixed crystals by distillation, 176 kg of pure 4,4 / -dioxydiphenyl-1,1-cyclohexane (yield: 82.2% of theory, melting point 186 ° C.) remaining in the residue. 175.8 kg of phenol are obtained from the phenol mother liquor by distillation and 16.4 kg of resinous bisphenol in the residue. 35.8 kg of phenol are recovered from the various washing waters by extraction.
Verfahren zur Herstellung
von reinem 4,4'-Dioxydiphenyl-cyclohexanMethod of manufacture
of pure 4,4'-dioxydiphenyl-cyclohexane
Zusatz zur Patentanmeldung F 19036 IVb/12 q
(Auslegeschrift 1 027 205)Addition to patent application F 19036 IVb / 12 q
(Interpretation document 1 027 205)
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft, LeverkusenPaint factories Bayer Aktiengesellschaft, Leverkusen
Dr. Karl-Heinrich Meyer, Krefeld-Bockum,Dr. Karl-Heinrich Meyer, Krefeld-Bockum,
und Dr. Hermann Schnell, Krefeld-Uerdingen,and Dr. Hermann Schnell, Krefeld-Uerdingen,
sind als Erfinder genannt wordenhave been named as inventors
Claims (2)
USA.-Patentschrift Nr. 2 623 908.Considered publications:
U.S. Patent No. 2,623,908.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF22890A DE1031788B (en) | 1956-10-24 | 1956-10-24 | Process for the production of pure 4, 4-dioxydiphenyl-cyclohexane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF22890A DE1031788B (en) | 1956-10-24 | 1956-10-24 | Process for the production of pure 4, 4-dioxydiphenyl-cyclohexane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1031788B true DE1031788B (en) | 1958-06-12 |
Family
ID=7090638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF22890A Pending DE1031788B (en) | 1956-10-24 | 1956-10-24 | Process for the production of pure 4, 4-dioxydiphenyl-cyclohexane |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1031788B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5414150A (en) * | 1993-12-03 | 1995-05-09 | The Dow Chemical Company | Preparation of 4,4'-dihydroxy-alpha-alkylstilbenes and 4,4'-dihydroxy-alpha, alpha'-dialkylstilbenes |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2623908A (en) * | 1951-11-23 | 1952-12-30 | Dow Chemical Co | Process for making 4, 4'-isopropylidenediphenol |
-
1956
- 1956-10-24 DE DEF22890A patent/DE1031788B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2623908A (en) * | 1951-11-23 | 1952-12-30 | Dow Chemical Co | Process for making 4, 4'-isopropylidenediphenol |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5414150A (en) * | 1993-12-03 | 1995-05-09 | The Dow Chemical Company | Preparation of 4,4'-dihydroxy-alpha-alkylstilbenes and 4,4'-dihydroxy-alpha, alpha'-dialkylstilbenes |
| US5475155A (en) * | 1993-12-03 | 1995-12-12 | The Dow Chemical Company | Preparation of 4,4'-dihydroxy-alpha'-dialkylstilbenes and 4, 4'-dihydroxy-alpha'-dialkylstilbenes |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2548470C2 (en) | Process for the preparation of pure 2,2-bis (4-hydroxyphenyl) propane | |
| DE1027205B (en) | Process for the preparation of pure 4,4'-dioxydiphenylalkanes | |
| DE69101329T2 (en) | Process for the preparation of D - (-) - 4-hydroxyphenylglycine from D.L.-4-hydroxyphenylglycine. | |
| DD140041B1 (en) | METHOD FOR THE PRODUCTION OF LONG-CHAINED N-ALKYLDIMETHYLMORPHOLINES | |
| DE1031788B (en) | Process for the production of pure 4, 4-dioxydiphenyl-cyclohexane | |
| DE1102750B (en) | Process for the preparation of a salt of theophylline bases | |
| DE1279024B (en) | Process for the production of trichlorophenol | |
| DE69106538T2 (en) | Cleaning process for N, N-diethylmandelic acid amide. | |
| DE2558507C3 (en) | Process for the resolution of dJ-1-phenyl-2-amino-1-propanol | |
| DE2558399C3 (en) | Process for the preparation of 3,6-dichloropicolinic acid | |
| DE1243206B (en) | Process for the separation of racemic 1-hydroxy-2-aminobutane into its optically active antipodes | |
| DE2556040A1 (en) | ANTIPODE SEPARATION PROCEDURES AND COMPOUNDS | |
| DE1143815B (en) | Process for the optical cleavage of N-acyl-DL-trypthophanes | |
| DE2126049C (en) | Process for racemizing an optically active phenylalanine | |
| DE1518353C3 (en) | Process for the production of optically active lysine or a compound thereof | |
| AT252896B (en) | Process for the production of optically active lysine | |
| DE2329731A1 (en) | MANUFACTURE OF GAMMA CYANOBUTYRALDEHYDE | |
| AT216671B (en) | Process for the preparation of compounds of various penicillins with sulfonamides | |
| CH641174A5 (en) | PROCESS FOR THE PREPARATION OF N-(4'-CHLORO-3'-SULFAMOYL-BENZENESULFONYL)-N-METHYL-2-AMINOMETHYL-2-METHYL-TETRAHYDROFURAN. | |
| DE613402C (en) | Process for the preparation of 4-pyridylpyridinium dichloride | |
| DE1917562C3 (en) | Process for the preparation of o- (2-diethylaminoethoxy) -omega-phenylpropiophenone | |
| DE1239697B (en) | Process for the preparation of methionine methylsulfonium chloride or bromide | |
| DE736024C (en) | Process for the production of oxygen-containing anthracene fragments | |
| AT229301B (en) | Process for the chlorination of o-cresol | |
| AT222644B (en) | Process for the preparation of pure 4,4'-dihydroxydiarylalkanes |