DE2509036C2 - Verfahren zur Herstellung von symmetrischen Diarylcarbonaten - Google Patents
Verfahren zur Herstellung von symmetrischen DiarylcarbonatenInfo
- Publication number
- DE2509036C2 DE2509036C2 DE2509036A DE2509036A DE2509036C2 DE 2509036 C2 DE2509036 C2 DE 2509036C2 DE 2509036 A DE2509036 A DE 2509036A DE 2509036 A DE2509036 A DE 2509036A DE 2509036 C2 DE2509036 C2 DE 2509036C2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- diaryl carbonates
- phosgene
- hydroxide solution
- phenol
- 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
- -1 diaryl carbonates Chemical class 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 28
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 18
- 150000002989 phenols Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- 238000007792 addition Methods 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 4
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
- 229940031826 phenolate Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 2
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229960001867 guaiacol Drugs 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- PBVUSKGIFXCUMR-UHFFFAOYSA-N 2-(2-methylpropoxy)phenol Chemical compound CC(C)COC1=CC=CC=C1O PBVUSKGIFXCUMR-UHFFFAOYSA-N 0.000 description 1
- GJHKNOGYPNYGPE-UHFFFAOYSA-N 2-(3-methylbutoxy)phenol Chemical compound CC(C)CCOC1=CC=CC=C1O GJHKNOGYPNYGPE-UHFFFAOYSA-N 0.000 description 1
- MTIDYGLTAOZOGU-UHFFFAOYSA-N 2-bromo-4-methylphenol Chemical compound CC1=CC=C(O)C(Br)=C1 MTIDYGLTAOZOGU-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- KKOWXJFINYUXEE-UHFFFAOYSA-N 2-butoxyphenol Chemical compound CCCCOC1=CC=CC=C1O KKOWXJFINYUXEE-UHFFFAOYSA-N 0.000 description 1
- MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical compound CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 description 1
- ZNCUUYCDKVNVJH-UHFFFAOYSA-N 2-isopropoxyphenol Chemical compound CC(C)OC1=CC=CC=C1O ZNCUUYCDKVNVJH-UHFFFAOYSA-N 0.000 description 1
- JFSVGKRARHIICJ-UHFFFAOYSA-N 2-propoxyphenol Chemical compound CCCOC1=CC=CC=C1O JFSVGKRARHIICJ-UHFFFAOYSA-N 0.000 description 1
- VGIJZDWQVCXVNL-UHFFFAOYSA-N 3-butoxyphenol Chemical compound CCCCOC1=CC=CC(O)=C1 VGIJZDWQVCXVNL-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXIKRTCSSLJURC-UHFFFAOYSA-N Dihydroeugenol Chemical compound CCCC1=CC=C(O)C(OC)=C1 PXIKRTCSSLJURC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical class ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- RXMRGBVLCSYIBO-UHFFFAOYSA-M tetramethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C RXMRGBVLCSYIBO-UHFFFAOYSA-M 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2509036A DE2509036C2 (de) | 1975-03-01 | 1975-03-01 | Verfahren zur Herstellung von symmetrischen Diarylcarbonaten |
| US05/661,528 US4016190A (en) | 1975-03-01 | 1976-02-26 | Process for the preparation of diarylcarbonates |
| NL7602068A NL7602068A (nl) | 1975-03-01 | 1976-02-27 | Werkwijze voor het bereiden van diarylcarbonaten. |
| GB8026/76A GB1517423A (en) | 1975-03-01 | 1976-03-01 | Process for the preparation of diaryl-carbonates |
| JP51021225A JPS59492B2 (ja) | 1975-03-01 | 1976-03-01 | ジアリ−ルカ−ボネ−トの製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2509036A DE2509036C2 (de) | 1975-03-01 | 1975-03-01 | Verfahren zur Herstellung von symmetrischen Diarylcarbonaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2509036A1 DE2509036A1 (de) | 1976-09-09 |
| DE2509036C2 true DE2509036C2 (de) | 1986-05-28 |
Family
ID=5940250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2509036A Expired DE2509036C2 (de) | 1975-03-01 | 1975-03-01 | Verfahren zur Herstellung von symmetrischen Diarylcarbonaten |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4016190A (OSRAM) |
| JP (1) | JPS59492B2 (OSRAM) |
| DE (1) | DE2509036C2 (OSRAM) |
| GB (1) | GB1517423A (OSRAM) |
| NL (1) | NL7602068A (OSRAM) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4102912A (en) * | 1977-02-14 | 1978-07-25 | General Electric Company | Process to prepare polyhalodiphenyl carbonates |
| JPS5938967B2 (ja) * | 1978-04-19 | 1984-09-20 | 三菱化学株式会社 | ポリカ−ボネ−ト有機溶剤溶液の洗浄法 |
| DE2925209A1 (de) * | 1979-06-22 | 1981-01-22 | Bayer Ag | Verfahren zur herstellung von dimethylcarbonat |
| US4697034A (en) * | 1985-11-15 | 1987-09-29 | General Electric Company | Process for making diaryl carbonates |
| ATE142195T1 (de) * | 1991-01-22 | 1996-09-15 | Sagami Chem Res | Verfahren zur herstellung von fluorbenzolderivaten und verwandter verbindungen |
| US5380909A (en) * | 1991-06-24 | 1995-01-10 | The Dow Chemical Company | Captive carbonyl halide process for production of diaryl carbonates |
| DE10063297A1 (de) * | 2000-12-19 | 2002-06-20 | Bayer Ag | Kontinuierliches Verfahren zur Herstellung von Kohlensäurediarylester |
| DE10063296A1 (de) | 2000-12-19 | 2002-06-20 | Bayer Ag | Verfahren zur Herstellung von Kohlensäurediarylester |
| DE10063869A1 (de) * | 2000-12-21 | 2002-06-27 | Bayer Ag | Kontinuierliches Verfahren zur Herstellung von Kohlensäurediarylester |
| EP1234845B1 (en) * | 2001-02-26 | 2008-11-12 | Mitsubishi Chemical Corporation | Process for producing diphenyl carbonate and process for producing aromatic polycarbonates |
| US6469192B1 (en) * | 2001-07-24 | 2002-10-22 | General Electric Company | Solventless preparation of ester-substituted diaryl carbonates |
| US6420588B1 (en) * | 2001-07-24 | 2002-07-16 | General Electric Company | Interfacial method of preparing ester-substituted diaryl carbonates |
| DE102006041465A1 (de) * | 2006-09-02 | 2008-03-06 | Bayer Materialscience Ag | Verfahren zur Herstellung von Diarylcarbonat |
| DE102007058701A1 (de) * | 2007-12-06 | 2009-06-10 | Bayer Materialscience Ag | Verfahren zur Herstellung von Diarylcarbonat |
| DE102008038031A1 (de) | 2008-08-16 | 2010-02-18 | Bayer Materialscience Ag | Verfahren zur Herstellung von Diarylcarbonaten |
| ATE516316T1 (de) * | 2008-02-13 | 2011-07-15 | Bayer Materialscience Ag | Verfahren zur herstellung von polycarbonaten |
| DE102009017862A1 (de) | 2009-04-17 | 2010-10-21 | Bayer Materialscience Ag | Verfahren zur Herstellung von Diarylcarbonat |
| DE102009032020A1 (de) | 2009-07-07 | 2011-01-13 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polycarbonat |
| CN105408249A (zh) | 2013-07-26 | 2016-03-16 | 沙特基础全球技术有限公司 | 用于生产高纯光气的方法和装置 |
| EP3024783A1 (en) | 2013-07-26 | 2016-06-01 | SABIC Global Technologies B.V. | Method and apparatus for producing high purity phosgene |
| WO2015119981A2 (en) | 2014-02-04 | 2015-08-13 | Sabic Global Technologies B.V. | Method for producing carbonates |
| KR101859209B1 (ko) | 2014-02-04 | 2018-06-27 | 사빅 글로벌 테크놀러지스 비.브이. | 카보네이트의 제조 방법 |
| EP4011861A1 (de) | 2020-12-11 | 2022-06-15 | Covestro Deutschland AG | Verfahren zur herstellung von diarylcarbonaten mit geringem phenolgehalt im abwasser |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1101386B (de) * | 1956-12-04 | 1961-03-09 | Bayer Ag | Verfahren zur Herstellung monomerer Kohlensaeureester |
| DE1056141B (de) * | 1957-04-08 | 1959-04-30 | Bayer Ag | Verfahren zur Herstellung von Diarylcarbonaten |
| US3382207A (en) * | 1965-09-30 | 1968-05-07 | Gen Electric | Flame-retardant polycarbonates |
| GB1227144A (OSRAM) * | 1967-04-05 | 1971-04-07 | ||
| GB1324763A (en) * | 1971-03-19 | 1973-07-25 | Continental Oil Co | Phase transfer catalysis of heterogeneous reactions by quaternary salts |
-
1975
- 1975-03-01 DE DE2509036A patent/DE2509036C2/de not_active Expired
-
1976
- 1976-02-26 US US05/661,528 patent/US4016190A/en not_active Expired - Lifetime
- 1976-02-27 NL NL7602068A patent/NL7602068A/xx not_active Application Discontinuation
- 1976-03-01 JP JP51021225A patent/JPS59492B2/ja not_active Expired
- 1976-03-01 GB GB8026/76A patent/GB1517423A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2509036A1 (de) | 1976-09-09 |
| GB1517423A (en) | 1978-07-12 |
| US4016190A (en) | 1977-04-05 |
| JPS51110535A (en) | 1976-09-30 |
| JPS59492B2 (ja) | 1984-01-07 |
| NL7602068A (nl) | 1976-09-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |