CA1106532A - Methode de preparation de polycarbonates - Google Patents

Methode de preparation de polycarbonates

Info

Publication number: CA1106532A
Authority: CA; Canada
Prior art keywords: accordance; carbonate; stage; alkylene carbonate; carried out
Prior art date: 1978-10-27
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

CA314,544A

Other languages

English (en)

Inventor

Kwo-Hrong Lai

Harold N. Silvers

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.)

Beatrice Companies Inc

Original Assignee

Beatrice Foods Co

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.)

1978-10-27

Filing date

1978-10-27

Publication date

1981-08-04

1978-10-27 Application filed by Beatrice Foods Co filed Critical Beatrice Foods Co

1978-10-27 Priority to CA314,544A priority Critical patent/CA1106532A/fr

1981-08-04 Application granted granted Critical

1981-08-04 Publication of CA1106532A publication Critical patent/CA1106532A/fr

Status Expired legal-status Critical Current

Links

239000004417 polycarbonate Substances 0.000 title claims abstract description 33
229920000515 polycarbonate Polymers 0.000 title claims abstract description 32
238000004519 manufacturing process Methods 0.000 title abstract description 7
238000006243 chemical reaction Methods 0.000 claims abstract description 23
150000002148 esters Chemical class 0.000 claims abstract description 10
150000002334 glycols Chemical class 0.000 claims abstract description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
229910052799 carbon Inorganic materials 0.000 claims abstract description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 40
-1 alkylene carbonate Chemical compound 0.000 claims description 33
238000000034 method Methods 0.000 claims description 26
230000008569 process Effects 0.000 claims description 23
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 20
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical group O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 13
239000006227 byproduct Substances 0.000 claims description 11
150000002440 hydroxy compounds Chemical class 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
239000000047 product Substances 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
238000009835 boiling Methods 0.000 claims description 7
150000002009 diols Chemical class 0.000 claims description 7
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
239000000376 reactant Substances 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract description 2
125000004122 cyclic group Chemical group 0.000 abstract description 2
230000007717 exclusion Effects 0.000 abstract 1
239000003054 catalyst Substances 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000004821 distillation Methods 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 5
150000004649 carbonic acid derivatives Chemical class 0.000 description 4
239000000463 material Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
NDWWLJQHOLSEHX-UHFFFAOYSA-L calcium;octanoate Chemical compound [Ca+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O NDWWLJQHOLSEHX-UHFFFAOYSA-L 0.000 description 3
125000001033 ether group Chemical group 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
229910052684 Cerium Inorganic materials 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
229910052788 barium Inorganic materials 0.000 description 2
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 2
YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
239000011135 tin Substances 0.000 description 2
229910052718 tin Inorganic materials 0.000 description 2
229910052719 titanium Inorganic materials 0.000 description 2
239000010936 titanium Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
MFEVGQHCNVXMER-UHFFFAOYSA-L 1,3,2$l^{2}-dioxaplumbetan-4-one Chemical compound [Pb+2].[O-]C([O-])=O MFEVGQHCNVXMER-UHFFFAOYSA-L 0.000 description 1
HLSUQUJDDMLNMX-UHFFFAOYSA-N 1-(2-octadec-9-enoxyethoxy)octadec-9-ene Chemical class CCCCCCCCC=CCCCCCCCCOCCOCCCCCCCCC=CCCCCCCCC HLSUQUJDDMLNMX-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
244000043261 Hevea brasiliensis Species 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
229910000003 Lead carbonate Inorganic materials 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
229910000421 cerium(III) oxide Inorganic materials 0.000 description 1
HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
229910052732 germanium Inorganic materials 0.000 description 1
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
229940119177 germanium dioxide Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229920006158 high molecular weight polymer Polymers 0.000 description 1
229960000443 hydrochloric acid Drugs 0.000 description 1
235000011167 hydrochloric acid Nutrition 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000003999 initiator Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
UWRBYRMOUPAKLM-UHFFFAOYSA-L lead arsenate Chemical compound [Pb+2].O[As]([O-])([O-])=O UWRBYRMOUPAKLM-UHFFFAOYSA-L 0.000 description 1
HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 1
ZPPSOOVFTBGHBI-UHFFFAOYSA-N lead(2+);oxido(oxo)borane Chemical compound [Pb+2].[O-]B=O.[O-]B=O ZPPSOOVFTBGHBI-UHFFFAOYSA-N 0.000 description 1
YEXPOXQUZXUXJW-UHFFFAOYSA-N lead(II) oxide Inorganic materials [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
229940117969 neopentyl glycol Drugs 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Landscapes

Polyesters Or Polycarbonates (AREA)

CA314,544A 1978-10-27 1978-10-27 Methode de preparation de polycarbonates Expired CA1106532A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA314,544A CA1106532A (fr)	1978-10-27	1978-10-27	Methode de preparation de polycarbonates

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA314,544A CA1106532A (fr)	1978-10-27	1978-10-27	Methode de preparation de polycarbonates

Publications (1)

Publication Number	Publication Date
CA1106532A true CA1106532A (fr)	1981-08-04

Family

ID=4112729

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA314,544A Expired CA1106532A (fr)	1978-10-27	1978-10-27	Methode de preparation de polycarbonates

Country Status (1)

Country	Link
CA (1)	CA1106532A (fr)

1978
- 1978-10-27 CA CA314,544A patent/CA1106532A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-08-04	MKEX	Expiry

Publication	Publication Date	Title
US4131731A (en)	1978-12-26	Process for preparing polycarbonates
US6646100B2 (en)	2003-11-11	Aliphatic polycarbonate homo-and co-polymers produced by DMC catalysis and the process for their production
US6818784B2 (en)	2004-11-16	Process for producing aliphatic oligocarbonate diols
CA2466255C (fr)	2011-10-18	Acetylacetonate d'ytterbium(iii) utilise comme catalyseur pour la preparation de polyols d'oligocarbonates aliphatiques
JPS6312896B2 (fr)	1988-03-23
US5847069A (en)	1998-12-08	Process for the preparation of polycarbonate copolyether polyols
EP0849303A2 (fr)	1998-06-24	Procédé de préparation de polycarbonate-copolyester diols
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JP2003192783A (ja)	2003-07-09	脂肪族オリゴカーボネートの調製における触媒の使用
JPH0784515B2 (ja)	1995-09-13	ポリカーボネートの製造方法
US20040143130A1 (en)	2004-07-22	Process for producing aliphatic oligocarbonate diols
CA1106532A (fr)	1981-08-04	Methode de preparation de polycarbonates
JP2879685B2 (ja)	1999-04-05	ポリカーボネートジオール
Rokicki et al.	2000	Synthesis of six-membered cyclic carbonate monomers by disproportionation of 1, 3-bis (alkoxycarbonyloxy) propanes and their polymerization
JP7827751B2 (ja)	2026-03-10	ポリカーボネートジオールの製造方法、ポリカーボネートジオール及びエステル交換触媒
US3359242A (en)	1967-12-19	Process for producing high molecular weight (cyclo) aliphatic polyesters of carbonicacid with (cyclo) glycols
JP2884358B2 (ja)	1999-04-19	ポリウレタン
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US3506623A (en)	1970-04-14	Process for producing high molecular weight (cyclo) aliphatic polyesters of carbonic acid with (cyclo) glycols
Berti et al.	2002	New route to poly (alkylene terephthalate) s by reaction of dimethyl terephthalate with cyclic carbonates
US3432473A (en)	1969-03-11	Process for the production of aliphatic or cycloaliphatic polyesters of carbonic acid
EP0227819A4 (fr)	1988-02-08	Procede destine a augmenter le poids moleculaire des poly(carbonates d'alkylene) polyols.
CN118660923A (zh)	2024-09-17	聚碳酸酯二醇的制造方法、聚碳酸酯二醇和酯交换催化剂
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