BE878184A - Procede de preparation de polyesters de glycols et d'acides dicarboxyliques - Google Patents

Procede de preparation de polyesters de glycols et d'acides dicarboxyliques Download PDF

Info

Publication number: BE878184A
Authority: BE; Belgium
Prior art keywords: glycol; mixture; column; separation; alcohol
Prior art date: 1979-06-26

Application number

BE0/196681A

Other languages

English (en)

French (fr)

Original Assignee

Nosovsky Jury E

Vishnyakov Mikhail V

Barshtein Rema S

Scherbakov Vladimir S

Sverdlik Vladimir L

Martynov Stanislavf

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.)

1979-06-26

Filing date

1979-08-10

Publication date

1980-02-11

1979-06-26 Priority to DD79213897A priority Critical patent/DD144553A1/de

1979-08-10 Application filed by Nosovsky Jury E, Vishnyakov Mikhail V, Barshtein Rema S, Scherbakov Vladimir S, Sverdlik Vladimir L, Martynov Stanislavf filed Critical Nosovsky Jury E

1979-08-10 Priority to BE0/196681A priority patent/BE878184A/fr

1980-02-11 Publication of BE878184A publication Critical patent/BE878184A/fr

Links

238000000034 method Methods 0.000 title claims description 44
229920000728 polyester Polymers 0.000 title description 17
150000002334 glycols Chemical class 0.000 title description 14
150000001991 dicarboxylic acids Chemical class 0.000 title description 13
238000002360 preparation method Methods 0.000 title description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 184
239000000203 mixture Substances 0.000 claims description 80
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 74
238000000926 separation method Methods 0.000 claims description 62
125000001931 aliphatic group Chemical group 0.000 claims description 28
238000009835 boiling Methods 0.000 claims description 11
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 60
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 56
238000005809 transesterification reaction Methods 0.000 description 31
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 24
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 19
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
239000004246 zinc acetate Substances 0.000 description 9
238000011049 filling Methods 0.000 description 8
238000004821 distillation Methods 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
239000000047 product Substances 0.000 description 7
XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
229940100539 dibutyl adipate Drugs 0.000 description 6
OBLMUVZPDITTKB-UHFFFAOYSA-N [Fe].[Co].[Cu] Chemical compound [Fe].[Co].[Cu] OBLMUVZPDITTKB-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 4
NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
239000000463 material Substances 0.000 description 4
238000004064 recycling Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 3
239000000919 ceramic Substances 0.000 description 3
238000004040 coloring Methods 0.000 description 3
239000012467 final product Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000009434 installation Methods 0.000 description 3
229920001451 polypropylene glycol Polymers 0.000 description 3
239000002994 raw material Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
QVYYOKWPCQYKEY-UHFFFAOYSA-N [Fe].[Co] Chemical compound [Fe].[Co] QVYYOKWPCQYKEY-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 2
229960001826 dimethylphthalate Drugs 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
-1 polyethylene terephthalate Polymers 0.000 description 2
239000003507 refrigerant Substances 0.000 description 2
239000005060 rubber Substances 0.000 description 2
229940116351 sebacate Drugs 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000012808 vapor phase Substances 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000001944 continuous distillation Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000000835 fiber Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
150000003022 phthalic acids Chemical class 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
238000004451 qualitative analysis Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000010186 staining Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

BE0/196681A 1979-06-26 1979-08-10 Procede de preparation de polyesters de glycols et d'acides dicarboxyliques BE878184A (fr)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
DD79213897A DD144553A1 (de)	1979-06-26	1979-06-26	Verfahren zur herstellung der polyester mit glykolen und dikarbonsaeuren
BE0/196681A BE878184A (fr)	1979-06-26	1979-08-10	Procede de preparation de polyesters de glycols et d'acides dicarboxyliques

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DD79213897A DD144553A1 (de)	1979-06-26	1979-06-26	Verfahren zur herstellung der polyester mit glykolen und dikarbonsaeuren
BE878184		1979-08-10
BE0/196681A BE878184A (fr)	1979-06-26	1979-08-10	Procede de preparation de polyesters de glycols et d'acides dicarboxyliques

Publications (1)

Publication Number	Publication Date
BE878184A true BE878184A (fr)	1980-02-11

Family

ID=27158680

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/196681A BE878184A (fr)	1979-06-26	1979-08-10	Procede de preparation de polyesters de glycols et d'acides dicarboxyliques

Country Status (2)

Country	Link
BE (1)	BE878184A (de)
DD (1)	DD144553A1 (de)

1979
- 1979-06-26 DD DD79213897A patent/DD144553A1/de unknown
- 1979-08-10 BE BE0/196681A patent/BE878184A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
DD144553A1 (de)	1980-10-22

Legal Events

Date

Code

Title

Description

1986-02-28

RE

Patent lapsed

Owner name: MARTYNOV STANISLAVF.

Effective date: 19850831

Owner name: SCHERBAKOV VLADIMIR S.

Effective date: 19850831

Owner name: NOSOVSKY JURY E.

Effective date: 19850831

Owner name: BARSHTEIN REMA S.

Effective date: 19850831

Owner name: SVERDLIK VLADIMIR L.

Effective date: 19850831

Owner name: VISHNYAKOV MIKHAIL V.

Effective date: 19850831

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BE878184A - Procede de preparation de polyesters de glycols et d'acides dicarboxyliques - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (2)

Applications Claiming Priority (3)

Publications (1)

Family

ID=27158680

Family Applications (1)

Country Status (2)

Also Published As

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Legal Events