CA1039740A - Synthese de carbonates aromatiques - Google Patents

Synthese de carbonates aromatiques

Info

Publication number: CA1039740A
Authority: CA; Canada
Prior art keywords: alkyl; process according; carbonate; phenol; reaction
Prior art date: 1974-06-25
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

Application number

CA229,892A

Other languages

English (en)

Other versions

CA229892S (en

Inventor

Gabriello Illuminati

Ugo Romano

Renato Tesei

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Anic SpA

Original Assignee

Anic SpA

Priority date (The priority date 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 date listed.)

1974-06-25

Filing date

1975-06-23

Publication date

1978-10-03

1974-06-25 Priority claimed from IT2439374A external-priority patent/IT1025023B/it

1975-02-12 Priority claimed from IT2019175A external-priority patent/IT1046381B/it

1975-04-18 Priority claimed from IT2247275A external-priority patent/IT1049414B/it

1975-06-23 Application filed by Anic SpA filed Critical Anic SpA

1978-10-03 Application granted granted Critical

1978-10-03 Publication of CA1039740A publication Critical patent/CA1039740A/fr

Status Expired legal-status Critical Current

Links

-1 aromatic carbonates Chemical class 0.000 title claims abstract description 10
238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 4
239000003054 catalyst Substances 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
125000003118 aryl group Chemical group 0.000 claims abstract description 10
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
150000002989 phenols Chemical class 0.000 claims abstract description 4
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
150000007860 aryl ester derivatives Chemical class 0.000 claims abstract 2
125000004122 cyclic group Chemical group 0.000 claims abstract 2
238000006243 chemical reaction Methods 0.000 claims description 28
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 14
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
125000005910 alkyl carbonate group Chemical group 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
150000002736 metal compounds Chemical class 0.000 claims description 2
239000002841 Lewis acid Substances 0.000 claims 1
150000007517 lewis acids Chemical class 0.000 claims 1
239000007791 liquid phase Substances 0.000 claims 1
150000003623 transition metal compounds Chemical class 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 3
239000000543 intermediate Substances 0.000 abstract description 2
229920000515 polycarbonate Polymers 0.000 abstract description 2
239000004417 polycarbonate Substances 0.000 abstract description 2
238000003786 synthesis reaction Methods 0.000 abstract description 2
239000012948 isocyanate Substances 0.000 abstract 1
150000002513 isocyanates Chemical class 0.000 abstract 1
238000004519 manufacturing process Methods 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 7
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 7
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 6
150000002500 ions Chemical class 0.000 description 6
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 6
239000010936 titanium Substances 0.000 description 6
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 5
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 5
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 5
IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 4
150000004649 carbonic acid derivatives Chemical class 0.000 description 4
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 4
230000000717 retained effect Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000004821 distillation Methods 0.000 description 3
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 2
229930185605 Bisphenol Natural products 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000004411 aluminium Substances 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
230000002844 continuous effect Effects 0.000 description 2
YCNSGSUGQPDYTK-UHFFFAOYSA-N ethyl phenyl carbonate Chemical compound CCOC(=O)OC1=CC=CC=C1 YCNSGSUGQPDYTK-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007788 liquid Substances 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229940049953 phenylacetate Drugs 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229910052719 titanium Inorganic materials 0.000 description 2
ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
241001527806 Iti Species 0.000 description 1
241001163743 Perlodes Species 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
229910008046 SnC14 Inorganic materials 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
229910010061 TiC13 Inorganic materials 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
ACBQROXDOHKANW-UHFFFAOYSA-N bis(4-nitrophenyl) carbonate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)OC1=CC=C([N+]([O-])=O)C=C1 ACBQROXDOHKANW-UHFFFAOYSA-N 0.000 description 1
IEJIGPNLZYLLBP-WFGJKAKNSA-N bis(trideuteriomethyl) carbonate Chemical compound [2H]C([2H])([2H])OC(=O)OC([2H])([2H])[2H] IEJIGPNLZYLLBP-WFGJKAKNSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000011521 glass 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
CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
HPICRATUQFHULE-UHFFFAOYSA-J uranium(4+);tetrachloride Chemical compound Cl[U](Cl)(Cl)Cl HPICRATUQFHULE-UHFFFAOYSA-J 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA229,892A 1974-06-25 1975-06-23 Synthese de carbonates aromatiques Expired CA1039740A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
IT2439374A IT1025023B (it)	1974-06-25	1974-06-25	Processo per la preparazione di composti edericiolici con due eteroatomi separati da un atomo di carbonio
IT2019175A IT1046381B (it)	1975-02-12	1975-02-12	Procedimento per la preparazione di carbonati aromatici
IT2247275A IT1049414B (it)	1975-04-18	1975-04-18	Procedimento per la preparazione di poli carbonati aromatici

Publications (1)

Publication Number	Publication Date
CA1039740A true CA1039740A (fr)	1978-10-03

Family

ID=27273038

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA229,892A Expired CA1039740A (fr)	1974-06-25	1975-06-23	Synthese de carbonates aromatiques

Country Status (1)

Country	Link
CA (1)	CA1039740A (fr)

1975
- 1975-06-23 CA CA229,892A patent/CA1039740A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2024-03-25	MKEX	Expiry	Effective date: 19951003

Publication	Publication Date	Title
US4182726A (en)	1980-01-08	Process for the preparation of aromatic carbonates
US4252737A (en)	1981-02-24	Process for the production of aromatic carbonic acid esters
CA1058203A (fr)	1979-07-10	Procede de preparation de carbonates aromatiques
JPS6261582B2 (fr)	1987-12-22
CA2041646C (fr)	1999-06-15	Procede de production continue d'un carbonate aromatique
JPS60169445A (ja)	1985-09-02	芳香族カ−ボネ−トの改良された製造方法
EP0338760B1 (fr)	1995-01-04	Procédé de préparation de carbonates aromatiques
NO144526B (no)	1981-06-09	Fremgangsmaate for fremstilling av aromatiske karbonater
CA1161991A (fr)	1984-02-07	Methode de preparation de polycarbonates aromatiques
CA1185986A (fr)	1985-04-23	Preparation d'esters carbonates
US5149856A (en)	1992-09-22	Process for the preparation of carbonic acid diesters containing at least one aromatic ester group
JPH0532386B2 (fr)	1993-05-14
US5252771A (en)	1993-10-12	Aluminum trifluoride catalyst for production of diaryl carbonates
CA1039740A (fr)	1978-10-03	Synthese de carbonates aromatiques
JP2569351B2 (ja)	1997-01-08	芳香族カーボネート化合物を製造する方法
KR100918189B1 (ko)	2009-09-22	ｐ-하이드록시페닐알칸올의 제조방법
US5463102A (en)	1995-10-31	Process for the continuous production of aryl carbonates
US4272441A (en)	1981-06-09	Preparation of carbamates
KR900003296B1 (ko)	1990-05-14	2,2-비스(4'-히드록시페닐)프로판류의 제조방법
EP0760359B1 (fr)	1999-10-20	Méthode de préparation de carbonate aromatique
JP2680678B2 (ja)	1997-11-19	ポリカーボネートの製造法
JPH05331108A (ja)	1993-12-14	芳香族炭酸エステルの製造方法
KR101437876B1 (ko)	2014-09-04	방향족 카보네이트 화합물 합성용 촉매 조성물 및 이를 이용하여 방향족 카보네이트 화합물을 제조하는 방법
US20180371162A1 (en)	2018-12-27	Method for preparing a melt polycarbonate
JP2774334B2 (ja)	1998-07-09	ポリカーボネートの製造法