FR2317264A1 - Dihydroxy tetraalkyl diphenylmethanes prepn. - by condensing dialkylphenols with formaldehyde in the presence of acid catalyst, water and an alcohol - Google Patents
Dihydroxy tetraalkyl diphenylmethanes prepn. - by condensing dialkylphenols with formaldehyde in the presence of acid catalyst, water and an alcoholInfo
- Publication number
- FR2317264A1 FR2317264A1 FR7620509A FR7620509A FR2317264A1 FR 2317264 A1 FR2317264 A1 FR 2317264A1 FR 7620509 A FR7620509 A FR 7620509A FR 7620509 A FR7620509 A FR 7620509A FR 2317264 A1 FR2317264 A1 FR 2317264A1
- Authority
- FR
- France
- Prior art keywords
- formaldehyde
- water
- diphenylmethanes
- prepn
- tetraalkyl
- 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.)
- Withdrawn
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title abstract 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003377 acid catalyst Substances 0.000 title abstract 2
- 125000006840 diphenylmethane group Chemical class 0.000 title abstract 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 abstract 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 abstract 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000000711 cancerogenic effect Effects 0.000 abstract 1
- 231100000357 carcinogen Toxicity 0.000 abstract 1
- 239000003183 carcinogenic agent Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Prepn. of 4,4'-dihydoxy 3,3',5,5'-tetraalkyl diphenylmethanes (I) 2 in which R1 and R2 = alkyl gp.) comprises condensing a 2,6-dialkylphenol with formaldehyde in the presence of an acid catalyst water and >=1. Process gives high yiels of (I) and avoids use of HCl as catalyst, which is corrosive and may give rise to bis chloromethyl ether, a potent carcinogen. The presence of water and an alcohol lowers the vapour pressure of formaldehyde in the system, even at elevated temps., so that formaldehyde losses are reduced and the blockage of apparatus by deposits of low formaldehyde polymers is avoided. Prods. (I) are useful raw materials in the prodn. of polymeric materials. In an example 3050g 2,6-dimethylphenol, 750g 35% aq. formaldehyde soln. and 5850 g isobutanol were pumped continuously to an acid ion exchange resin bed, with an average residence time of 4 hours. Formaldehyde conversion was 82% and the yield more than 98%.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752530122 DE2530122A1 (en) | 1975-07-05 | 1975-07-05 | PROCESS FOR THE PREPARATION OF 4,4'-DIHYDROXY-3,3 ', 5,5'-TETRAALKYLDIPHENYLMETHANES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2317264A1 true FR2317264A1 (en) | 1977-02-04 |
Family
ID=5950782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7620509A Withdrawn FR2317264A1 (en) | 1975-07-05 | 1976-07-05 | Dihydroxy tetraalkyl diphenylmethanes prepn. - by condensing dialkylphenols with formaldehyde in the presence of acid catalyst, water and an alcohol |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS527944A (en) |
| DE (1) | DE2530122A1 (en) |
| FR (1) | FR2317264A1 (en) |
| NL (1) | NL7607344A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005005358A1 (en) * | 2003-07-01 | 2005-01-20 | General Electric Company | Process for the synthesis of bisphenol |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5731629A (en) * | 1980-08-01 | 1982-02-20 | Cosmo Co Ltd | Preparation of bisphenolethane |
| JP7255109B2 (en) * | 2018-09-04 | 2023-04-11 | 三菱ケミカル株式会社 | Method for producing bisphenol and method for producing polycarbonate resin |
-
1975
- 1975-07-05 DE DE19752530122 patent/DE2530122A1/en active Pending
-
1976
- 1976-06-30 JP JP7663376A patent/JPS527944A/en active Pending
- 1976-07-02 NL NL7607344A patent/NL7607344A/en unknown
- 1976-07-05 FR FR7620509A patent/FR2317264A1/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005005358A1 (en) * | 2003-07-01 | 2005-01-20 | General Electric Company | Process for the synthesis of bisphenol |
| US7132575B2 (en) | 2003-07-01 | 2006-11-07 | General Electric Company | Process for the synthesis of bisphenol |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2530122A1 (en) | 1977-01-27 |
| NL7607344A (en) | 1977-01-07 |
| JPS527944A (en) | 1977-01-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |