DK154135B - Fremgangsmaade til fremstilling af aromatiske carbonater - Google Patents
Fremgangsmaade til fremstilling af aromatiske carbonater Download PDFInfo
- Publication number
- DK154135B DK154135B DK526875AA DK526875A DK154135B DK 154135 B DK154135 B DK 154135B DK 526875A A DK526875A A DK 526875AA DK 526875 A DK526875 A DK 526875A DK 154135 B DK154135 B DK 154135B
- Authority
- DK
- Denmark
- Prior art keywords
- carbonate
- aromatic carbonates
- phenylethyl
- formula
- carbonates
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title 1
- -1 aromatic carbonates Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 6
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims description 3
- YCNSGSUGQPDYTK-UHFFFAOYSA-N ethyl phenyl carbonate Chemical compound CCOC(=O)OC1=CC=CC=C1 YCNSGSUGQPDYTK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000001944 continuous distillation Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- ITNVWQNWHXEMNS-UHFFFAOYSA-N methanolate;titanium(4+) Chemical compound [Ti+4].[O-]C.[O-]C.[O-]C.[O-]C ITNVWQNWHXEMNS-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000002904 solvent 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
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
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)
- Catalysts (AREA)
Description
DK 154135 B
Opfindelsen angår en særlig fremgangsmåde til fremstilling af aromatiske carbonater med formlen o-co - o
Rd-5) ^ R(l-5) hvor R betegner en substituent valgt blandt alkyl-, alkoxy-, aryl-, aryloxy- og N02~grupper.
Fremgangsmåden ifølge opfindelsen er ejendommelig ved det i kravets kendetegnende del angivne.
i 2
DK 154135 B
i
Det er kendt, at diarylcarbonater fremstilles ud fra de tilsvarende phenoler og phosgen ved hjælp af en indviklet teknik, som indebærer betydelige risici, og som medfører dannelsen af saltsyre som biprodukt. De aromatiske carbonater har stor industriel betydning, da de anvendes som mellemprodukter ved fremstillingen af aromatiske polycarbonater og ved fremstillingen af visse isocyanater.
Det har nu ifølge opfindelsen vist sig, at det er muligt at opnå diarylcarbonater i høje udbytter og med høje selektiviteter ved omsætning af phenylalkylcarbonater i nærværelse af passende katalysatorer i form af en titanorganisk forbindelse. Ved omsætningen opnås der foruden diarylcarbonater også dialkylcarbonater i ækvimolære mængder.
Omsætningen udføres i flydende fase med eller uden opløsningsmidler ved temperaturer på mellem 25 og 360°C, fortrinsvis mellem 80 og 250°C, og ved tryk på mellem 0,1 og 100 ata, fortrinsvis mellem 1 og 25 ata.
Fremgangsmåden ifølge opfindelsen belyses nærmere ved hjælp af de efterfølgende eksempler.
Eksempel 1 1 mol phenylethylcarbonat og 0,023 mol titantetraphenat omsattes i 4 timer ved 180°C.
Der opnåedes 40% omdannelse af phenylethylcarbonat med en selektivitet med hensyn til diphenylcarbonat og diethylcarbonat på mere end 95%, idet der også var dannet små mængder phenylethylether.
Eksempel 2 60 g phenylmethylcarbonat og 1,5 g titantetramethanolat omsattes i 4 timer ved 180°C i 50 cm^ n-hexan under kontinuerlig destillering af en azeotrop blanding af dimethylcarbonat og hexan ved et tilbagesvalingsforhold på 20/1.
Der opnåedes 63% omdannelse af phenylmethylcarbonat med en selektivitet på mere end 95% med hensyn til diphenylcarbonat og dimethylcarbonat, idet der var små mængder anisol til stede.
Claims (1)
- 3 DK 154135 B 4 timer ved 180°C i 60 cm ethylcyclohexan under kontinuerlig destillering af en azeotrop blanding af diethylcarbonat Og carbonhydridet ved et tilbagesvalingsforhold på 20/1. Der opnåedes 70% omdannelse af phenylethylcarbonat med en selektivitet på mere end 95% med hensyn til diphenylearbonat og diethyl carbonat, idet der var små mængder phenylethylether til stede. Fremgangsmåde til fremstilling af aromatiske carbonater med formlen (Cj>- o - c - o R(l-5)^ 0 "" R (1—5) hvori R betegner en substituent valgt blandt alkyl—, alkoxy-, aryl-, aryloxy- og No2-grupper., kendetegnet ved, at man omsæt ter forbindelser med formlen / O - COOR1 ' (1—5) hvori R har den ovennævnte betydning, og R1 betegner en ikke-tertiær alkylgruppe,med et katalysatorsystem i form af en titanorganisk forbindelse ved temperaturer på mellem 25 og 360¾ og ved tryk på mellem 0,1 og 100 ata.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT7429773A IT1025961B (it) | 1974-11-25 | 1974-11-25 | Processo per la preparazione di carbonati aromatici |
| IT2977374 | 1974-11-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK526875A DK526875A (da) | 1976-05-26 |
| DK154135B true DK154135B (da) | 1988-10-17 |
| DK154135C DK154135C (da) | 1989-03-06 |
Family
ID=11228414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK526875A DK154135C (da) | 1974-11-25 | 1975-11-21 | Fremgangsmaade til fremstilling af aromatiske carbonater |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4045464A (da) |
| JP (1) | JPS5848537B2 (da) |
| AT (1) | AT347428B (da) |
| BE (1) | BE835820A (da) |
| CA (1) | CA1058203A (da) |
| CH (1) | CH617660A5 (da) |
| DD (1) | DD122373A5 (da) |
| DE (1) | DE2552907C3 (da) |
| DK (1) | DK154135C (da) |
| FR (1) | FR2291967A1 (da) |
| GB (1) | GB1481920A (da) |
| HU (1) | HU171210B (da) |
| IL (1) | IL48542A (da) |
| IT (1) | IT1025961B (da) |
| LU (1) | LU73853A1 (da) |
| NO (1) | NO143900C (da) |
| SE (1) | SE426391B (da) |
| YU (1) | YU36006B (da) |
| ZA (1) | ZA757112B (da) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4182726A (en) * | 1974-06-25 | 1980-01-08 | Snamprogetti, S.P.A. | Process for the preparation of aromatic carbonates |
| JPS52156960A (en) * | 1976-06-24 | 1977-12-27 | Sanei Kagaku Kogyo Kk | Cooked frozen meat food |
| DE2736063A1 (de) * | 1977-08-10 | 1979-02-22 | Bayer Ag | Verfahren zur herstellung aromatischer kohlensaeureester |
| DE2736062A1 (de) * | 1977-08-10 | 1979-02-22 | Bayer Ag | Verfahren zur herstellung aromatischer kohlensaeureester |
| US4533504A (en) * | 1982-01-08 | 1985-08-06 | General Electric Company | Process for the preparation of diaryl carbonates |
| US4410464A (en) * | 1982-03-15 | 1983-10-18 | General Electric Company | Diaryl carbonate process |
| US4509537A (en) * | 1983-04-04 | 1985-04-09 | Philip Morris Incorporated | Smoking compositions |
| US4609501A (en) * | 1983-12-27 | 1986-09-02 | General Electric Company | Process for the preparation of aromatic carbonates |
| US5166393A (en) * | 1987-10-05 | 1992-11-24 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing diaryl carbonate |
| US5034557A (en) * | 1988-04-16 | 1991-07-23 | Mitsui Petrochemical Industries, Ltd. | Process for production of aromatic carbonate compound |
| JP2540590B2 (ja) * | 1988-04-16 | 1996-10-02 | 三井石油化学工業株式会社 | 芳香族カ―ボネ―ト化合物を製造する方法 |
| US5167946A (en) * | 1990-12-27 | 1992-12-01 | The Dow Chemical Company | Diaryl carbonate process |
| GB2255972A (en) * | 1991-04-12 | 1992-11-25 | Davy Res & Dev Ltd | Production of diaryl carbonates. |
| WO1992018459A1 (fr) * | 1991-04-18 | 1992-10-29 | Yoshitomi Pharmaceutical Industries, Ltd. | Compose d'ester benzoique et procede de production |
| US5252771A (en) * | 1991-05-28 | 1993-10-12 | The Dow Chemical Company | Aluminum trifluoride catalyst for production of diaryl carbonates |
| US5380909A (en) * | 1991-06-24 | 1995-01-10 | The Dow Chemical Company | Captive carbonyl halide process for production of diaryl carbonates |
| US5239105A (en) * | 1992-01-30 | 1993-08-24 | The Dow Chemical Company | Catalytic formation of diarylcarbonates |
| DE4207853A1 (de) * | 1992-03-12 | 1993-09-16 | Bayer Ag | Verfahren zur herstellung von aromatischen carbonaten |
| US5380908A (en) * | 1992-10-08 | 1995-01-10 | Daicel Chemical Industries, Ltd. | Continuous production of aromatic carbonates |
| DE4301899A1 (de) * | 1993-01-25 | 1994-07-28 | Bayer Ag | Verfahren zur kontinuierlichen Herstellung von Arylcarbonaten |
| TW310322B (da) * | 1994-05-25 | 1997-07-11 | Nippon Catalytic Chem Ind | |
| IT1282363B1 (it) * | 1996-01-16 | 1998-03-20 | Enichem Spa | Procedimento continuo per la preparazione di fenil metil carbonato |
| US5980445A (en) * | 1996-11-22 | 1999-11-09 | Mitsubishi Gas Chemical Company, Inc. | Process for producing diaryl carbonate |
| US5962720A (en) * | 1997-05-29 | 1999-10-05 | Wilson Greatbatch Ltd. | Method of synthesizing unsymmetric organic carbonates and preparing nonaqueous electrolytes for alkali ion electrochemical cells |
| US7417161B2 (en) * | 2002-02-05 | 2008-08-26 | Lg Chem. Ltd. | Continuous method for preparing aromatic carbonate using a heterogeneous catalyst and a reaction apparatus for the same |
| US7919644B2 (en) | 2004-06-17 | 2011-04-05 | Asahi Kasei Chemicals Corporation | Process for producing an aromatic carbonate |
| BRPI0512524A (pt) * | 2004-06-25 | 2008-03-11 | Asahi Kasei Chemicals Corp | processo para a produção de um carbonato aromático, processo para a produção industrial do mesmo, carbonato aromático, e, coluna de destilação contìnua de múltiplos estágios |
| EP1762560A4 (en) * | 2004-06-25 | 2008-05-07 | Asahi Kasei Chemicals Corp | PROCESS FOR PRODUCING AROMATIC CARBONATE AT THE INDUSTRIAL SCALE |
| US20070219387A1 (en) | 2004-07-13 | 2007-09-20 | Asahi Kasei Chemicals Corporation | Industrial Process for Producing an Aromatic Carbonate |
| EP1775280B1 (en) | 2004-07-13 | 2013-09-11 | Asahi Kasei Chemicals Corporation | Industrial process for producing aromatic carbonate |
| JP4224104B2 (ja) | 2004-07-14 | 2009-02-12 | 旭化成ケミカルズ株式会社 | 芳香族カーボネート類を工業的に製造する方法 |
| EP1767517A4 (en) | 2004-07-14 | 2008-08-20 | Asahi Kasei Chemicals Corp | INDUSTRIAL PROCESS FOR PREPARING AN AROMATIC CARBONATE |
| EA010066B1 (ru) | 2004-08-25 | 2008-06-30 | Асахи Касеи Кемикалз Корпорейшн | Способ производства высокочистого дифенилкарбоната в промышленном масштабе |
| US20070260083A1 (en) * | 2004-09-02 | 2007-11-08 | Shinsuke Fukuoka | Industrial Process for Production of High-Purity Diphenyl Carbonate |
| JP4292211B2 (ja) * | 2004-09-03 | 2009-07-08 | 旭化成ケミカルズ株式会社 | 高純度ジアリールカーボネートの工業的製造方法 |
| EP1795522A4 (en) * | 2004-09-27 | 2008-08-06 | Asahi Kasei Chemicals Corp | PROCESS FOR THE MANUFACTURE OF AROMATIC CARBONATE IN INDUSTRIAL STANDARD |
| WO2006041075A1 (ja) * | 2004-10-14 | 2006-04-20 | Asahi Kasei Chemicals Corporation | 高純度ジアリールカーボネートの製造方法 |
| TWI321561B (en) | 2004-12-21 | 2010-03-11 | Asahi Kasei Chemicals Corp | Method for producing aromatic carbonate |
| CA2595125C (en) | 2004-12-24 | 2011-11-08 | Asahi Kasei Chemicals Corporation | Process for production of aromatic carbonate |
| US7378540B2 (en) * | 2005-10-21 | 2008-05-27 | Catalytic Distillation Technologies | Process for producing organic carbonates |
| EP2178820A1 (en) * | 2007-08-20 | 2010-04-28 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of a diaryl carbonate |
| US8110698B2 (en) | 2008-02-11 | 2012-02-07 | Shell Oil Company | Process for producing diphenyl carbonate |
| US7851645B2 (en) * | 2008-02-11 | 2010-12-14 | Catalytic Distillation Technologies | Process for continuous production of organic carbonates or organic carbamates and solid catalysts therefore |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3517029A (en) * | 1964-08-17 | 1970-06-23 | Eastman Kodak Co | Cyclic polymethylene monothiolcarbonates and their preparation |
| DE1770329A1 (de) * | 1967-05-05 | 1970-08-20 | Inst Tworzyw Sztucznych | Verfahren zur Herstellung von Polycarbonaten |
| US3655626A (en) * | 1968-10-02 | 1972-04-11 | United States Steel Corp | Interpolycarbonates from 9 10 - bis (hydroxymethyl) - s - octahydroanthracene-bis (alkyl or aryl carbonates) |
-
1974
- 1974-11-25 IT IT7429773A patent/IT1025961B/it active
-
1975
- 1975-11-12 ZA ZA00757112A patent/ZA757112B/xx unknown
- 1975-11-18 GB GB47551/75A patent/GB1481920A/en not_active Expired
- 1975-11-21 BE BE162077A patent/BE835820A/xx not_active IP Right Cessation
- 1975-11-21 DK DK526875A patent/DK154135C/da not_active IP Right Cessation
- 1975-11-24 YU YU2980/75A patent/YU36006B/xx unknown
- 1975-11-24 CH CH1520775A patent/CH617660A5/it not_active IP Right Cessation
- 1975-11-24 NO NO75753959A patent/NO143900C/no unknown
- 1975-11-24 AT AT891775A patent/AT347428B/de not_active IP Right Cessation
- 1975-11-24 LU LU73853A patent/LU73853A1/xx unknown
- 1975-11-24 CA CA240,327A patent/CA1058203A/en not_active Expired
- 1975-11-24 FR FR7535832A patent/FR2291967A1/fr active Granted
- 1975-11-24 HU HU75AI00000248A patent/HU171210B/hu unknown
- 1975-11-25 JP JP50140312A patent/JPS5848537B2/ja not_active Expired
- 1975-11-25 IL IL7548542A patent/IL48542A/xx unknown
- 1975-11-25 DE DE2552907A patent/DE2552907C3/de not_active Expired
- 1975-11-25 SE SE7513239A patent/SE426391B/xx unknown
- 1975-11-25 DD DD189676A patent/DD122373A5/xx unknown
- 1975-12-01 US US05/636,604 patent/US4045464A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2552907C3 (de) | 1978-08-17 |
| DE2552907A1 (de) | 1976-05-26 |
| IT1025961B (it) | 1978-08-30 |
| ZA757112B (en) | 1976-10-27 |
| BE835820A (fr) | 1976-05-21 |
| NO143900B (no) | 1981-01-26 |
| ATA891775A (de) | 1978-05-15 |
| HU171210B (hu) | 1977-12-28 |
| SE426391B (sv) | 1983-01-17 |
| AU8679375A (en) | 1977-05-26 |
| DK526875A (da) | 1976-05-26 |
| US4045464A (en) | 1977-08-30 |
| GB1481920A (en) | 1977-08-03 |
| NO143900C (no) | 1981-05-06 |
| IL48542A0 (en) | 1976-01-30 |
| LU73853A1 (da) | 1976-06-11 |
| JPS5848537B2 (ja) | 1983-10-28 |
| YU298075A (en) | 1981-02-28 |
| FR2291967B1 (da) | 1979-02-02 |
| DE2552907B2 (de) | 1977-12-08 |
| NO753959L (da) | 1976-05-26 |
| FR2291967A1 (fr) | 1976-06-18 |
| DK154135C (da) | 1989-03-06 |
| AT347428B (de) | 1978-12-27 |
| JPS5175044A (da) | 1976-06-29 |
| SE7513239L (sv) | 1976-05-26 |
| YU36006B (en) | 1981-11-13 |
| DD122373A5 (da) | 1976-10-05 |
| CA1058203A (en) | 1979-07-10 |
| IL48542A (en) | 1978-08-31 |
| CH617660A5 (da) | 1980-06-13 |
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