DD292904A5 - Verfahren zur herstellung von p-alkylcalix 4 arenen - Google Patents

Verfahren zur herstellung von p-alkylcalix 4 arenen Download PDF

Info

Publication number: DD292904A5
Authority: DD; German Democratic Republic
Prior art keywords: alkylcalix; mixture; arenes; arene; preparation
Prior art date: 1990-03-22

Application number

DD90338955A

Other languages

German (de)

English (en)

Inventor

Gerhard Goermar

Klaus Seiffarth

Manfred Schulz

Original Assignee

Veb Leuna-Werke,De

Technische Hochschule Leuna-Merseburg,De

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.)

1990-03-22

Filing date

1990-03-22

Publication date

1991-08-14

1990-03-22 Application filed by Veb Leuna-Werke,De, Technische Hochschule Leuna-Merseburg,De filed Critical Veb Leuna-Werke,De

1990-03-22 Priority to DD90338955A priority Critical patent/DD292904A5/de

1991-03-15 Priority to EP91104021A priority patent/EP0447977A1/fr

1991-08-14 Publication of DD292904A5 publication Critical patent/DD292904A5/de

Links

150000004945 aromatic hydrocarbons Chemical class 0.000 title claims abstract description 23
238000000034 method Methods 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims abstract description 8
241001120493 Arene Species 0.000 claims abstract description 13
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
239000000203 mixture Substances 0.000 abstract description 23
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 11
229930195733 hydrocarbon Natural products 0.000 abstract description 8
150000002430 hydrocarbons Chemical class 0.000 abstract description 8
150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 7
229930040373 Paraformaldehyde Natural products 0.000 abstract description 6
229920002866 paraformaldehyde Polymers 0.000 abstract description 6
239000003054 catalyst Substances 0.000 abstract description 4
150000001875 compounds Chemical class 0.000 abstract description 3
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract description 3
239000012188 paraffin wax Substances 0.000 abstract description 3
239000011541 reaction mixture Substances 0.000 abstract description 3
239000003513 alkali Substances 0.000 abstract 1
-1 alkyl phenol Chemical compound 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000007787 solid Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
239000012429 reaction media Substances 0.000 description 6
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
230000007717 exclusion Effects 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
NVKLTRSBZLYZHK-UHFFFAOYSA-N 4-tert-butylcalix[4]arene Chemical compound C1C(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC2=CC(C(C)(C)C)=CC1=C2O NVKLTRSBZLYZHK-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
238000006555 catalytic reaction Methods 0.000 description 3
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
231100000331 toxic Toxicity 0.000 description 3
230000002588 toxic effect Effects 0.000 description 3
OLZFZIXORGGLLS-UHFFFAOYSA-N 4-tert-butylcalix[8]arene Chemical compound C1C(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC2=CC(C(C)(C)C)=CC1=C2O OLZFZIXORGGLLS-UHFFFAOYSA-N 0.000 description 2
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000008098 formaldehyde solution Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
GQPLZGRPYWLBPW-UHFFFAOYSA-N calix[4]arene Chemical class C1C(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC2=CC=CC1=C2 GQPLZGRPYWLBPW-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/115—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using acetals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/92—Systems containing at least three condensed rings with a condensed ring system consisting of at least two mutually uncondensed aromatic ring systems, linked by an annular structure formed by carbon chains on non-adjacent positions of the aromatic system, e.g. cyclophanes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD90338955A 1990-03-22 1990-03-22 Verfahren zur herstellung von p-alkylcalix 4 arenen DD292904A5 (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
DD90338955A DD292904A5 (de)	1990-03-22	1990-03-22	Verfahren zur herstellung von p-alkylcalix 4 arenen
EP91104021A EP0447977A1 (fr)	1990-03-22	1991-03-15	Procedé pour la fabrication de p-alcylecalix[4]arènes

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD90338955A DD292904A5 (de)	1990-03-22	1990-03-22	Verfahren zur herstellung von p-alkylcalix 4 arenen

Publications (1)

Publication Number	Publication Date
DD292904A5 true DD292904A5 (de)	1991-08-14

Family

ID=5617243

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90338955A DD292904A5 (de)	1990-03-22	1990-03-22	Verfahren zur herstellung von p-alkylcalix 4 arenen

Country Status (2)

Country	Link
EP (1)	EP0447977A1 (fr)
DD (1)	DD292904A5 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2052798C (fr) *	1990-10-06	2001-08-21	Michael Lancaster	Resines phenoliques
DE69706412T2 (de) *	1996-04-09	2002-05-29	Cal-X Investment S.A., Geneva	Verfahren zur herstellung von calixarenen
US6271337B1 (en)	1997-04-07	2001-08-07	Fillger S.A.	Process for the preparation of calixarenes and new calixarene compounds
US10781154B2 (en)	2018-02-09	2020-09-22	Si Group, Inc.	Processes for preparing calixarenes
US10843990B2 (en)	2018-02-09	2020-11-24	Si Group, Inc.	Processes for preparing calix[4]arenes from calix[8]arenes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1248354A (en) *	1969-02-27	1971-09-29	Monsanto Australia	Production of phenol/formaldehyde resins

1990
- 1990-03-22 DD DD90338955A patent/DD292904A5/de not_active IP Right Cessation
1991
- 1991-03-15 EP EP91104021A patent/EP0447977A1/fr not_active Ceased

Also Published As

Publication number	Publication date
EP0447977A1 (fr)	1991-09-25

Legal Events

Date	Code	Title
1994-03-31	NPI	Change in the person, name or address of the patentee (addendum to changes before extension act)
1994-04-14	NPI	Change in the person, name or address of the patentee (addendum to changes before extension act)
1994-06-23	RPI	Change in the person, name or address of the patentee (searches according to art. 11 and 12 extension act)
1999-07-08	ENJ	Ceased due to non-payment of renewal fee

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