DD146285A1 - Verfahren zur herstellung von alkalisalzen von hydroxybenzoesaeureestern - Google Patents

Verfahren zur herstellung von alkalisalzen von hydroxybenzoesaeureestern Download PDF

Info

Publication number: DD146285A1
Authority: DD; German Democratic Republic
Prior art keywords: hydroxybenzoic acid; neutralization; alkali metal; solution; acid ester
Prior art date: 1978-09-30

Application number

DD79215892A

Other languages

German (de)

English (en)

Inventor

Peter Schnegg

Walter Rapp

Bernhard Vosteen

Original Assignee

Bayer Ag

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.)

1978-09-30

Filing date

1979-09-28

Publication date

1981-02-04

1978-09-30 Priority claimed from DE19782842807 external-priority patent/DE2842807A1/de

1979-04-27 Priority claimed from DE19792917273 external-priority patent/DE2917273A1/de

1979-09-28 Application filed by Bayer Ag filed Critical Bayer Ag

1981-02-04 Publication of DD146285A1 publication Critical patent/DD146285A1/de

Links

238000000034 method Methods 0.000 title claims abstract description 25
238000002360 preparation method Methods 0.000 title abstract description 10
150000002148 esters Chemical class 0.000 title description 9
239000002253 acid Substances 0.000 title description 2
-1 alkali metal salts Chemical class 0.000 claims abstract description 94
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 52
238000006386 neutralization reaction Methods 0.000 claims abstract description 50
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 48
239000000725 suspension Substances 0.000 claims abstract description 33
238000001035 drying Methods 0.000 claims abstract description 31
150000005165 hydroxybenzoic acids Chemical class 0.000 claims abstract description 22
150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 13
229910001854 alkali hydroxide Inorganic materials 0.000 claims abstract description 5
239000000243 solution Substances 0.000 claims description 71
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
159000000000 sodium salts Chemical class 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 6
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 4
238000003860 storage Methods 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
239000007864 aqueous solution Substances 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 claims description 2
238000007127 saponification reaction Methods 0.000 claims description 2
238000004090 dissolution Methods 0.000 claims 2
230000001419 dependent effect Effects 0.000 claims 1
150000002500 ions Chemical class 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 9
150000001447 alkali salts Chemical class 0.000 abstract description 7
150000001340 alkali metals Chemical class 0.000 abstract description 6
229910052736 halogen Inorganic materials 0.000 abstract description 6
150000002367 halogens Chemical class 0.000 abstract description 6
229910052739 hydrogen Inorganic materials 0.000 abstract description 5
239000001257 hydrogen Substances 0.000 abstract description 5
125000003342 alkenyl group Chemical group 0.000 abstract description 4
125000003282 alkyl amino group Chemical group 0.000 abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 abstract description 4
150000002431 hydrogen Chemical class 0.000 abstract description 4
101100242909 Streptococcus pneumoniae (strain ATCC BAA-255 / R6) pbpA gene Proteins 0.000 abstract 1
101100269618 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) aliA gene Proteins 0.000 abstract 1
101150109310 msrAB1 gene Proteins 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 22
235000011121 sodium hydroxide Nutrition 0.000 description 22
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 17
125000004432 carbon atom Chemical group C* 0.000 description 13
239000000047 product Substances 0.000 description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
125000003710 aryl alkyl group Chemical group 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 6
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 4
238000001694 spray drying Methods 0.000 description 4
238000004544 sputter deposition Methods 0.000 description 4
239000000375 suspending agent Substances 0.000 description 4
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 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 3
235000013305 food Nutrition 0.000 description 3
239000007789 gas Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
QGNLHMKIGMZKJX-UHFFFAOYSA-N 3-chloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(Cl)=C1 QGNLHMKIGMZKJX-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002537 cosmetic Substances 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000003641 microbiacidal effect Effects 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
230000003472 neutralizing effect Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000002245 particle Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000012209 synthetic fiber Substances 0.000 description 2
229920002994 synthetic fiber Polymers 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
MOZDKDIOPSPTBH-UHFFFAOYSA-N Benzyl parahydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 MOZDKDIOPSPTBH-UHFFFAOYSA-N 0.000 description 1
208000001840 Dandruff Diseases 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000006309 butyl amino group Chemical group 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000002036 drum drying Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000013373 food additive Nutrition 0.000 description 1
239000002778 food additive Substances 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Chemical class 0.000 description 1
239000002184 metal Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
JQNWTCWXVRAUJO-UHFFFAOYSA-N n-(diethylamino)-n-(ethylamino)propan-1-amine Chemical compound CCCN(NCC)N(CC)CC JQNWTCWXVRAUJO-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940031826 phenolate Drugs 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000007921 spray 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
235000013311 vegetables Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/64—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring the carbon skeleton being further substituted by singly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring

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

DD79215892A 1978-09-30 1979-09-28 Verfahren zur herstellung von alkalisalzen von hydroxybenzoesaeureestern DD146285A1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19782842807 DE2842807A1 (de)	1978-09-30	1978-09-30	Verfahren zur herstellung von wasserfreien alkalisalzen von hydroxybenzoesaeureestern und wasserfreie alkalisalze von hydroxybenzoesaeureestern
DE19792917273 DE2917273A1 (de)	1979-04-27	1979-04-27	Weitgehend wasserfreie und hydroxybenzoesaeure-freie alkalisalze von hydroxybenzoesaeureestern und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
DD146285A1 true DD146285A1 (de)	1981-02-04

Family

ID=25775926

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79215892A DD146285A1 (de)	1978-09-30	1979-09-28	Verfahren zur herstellung von alkalisalzen von hydroxybenzoesaeureestern

Country Status (8)

Country	Link
US (1)	US4276431A (da)
EP (1)	EP0009699B1 (da)
CA (1)	CA1140572A (da)
DD (1)	DD146285A1 (da)
DE (1)	DE2961325D1 (da)
DK (1)	DK409279A (da)
ES (1)	ES484577A1 (da)
IL (1)	IL58343A (da)

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US4499295A (en) *	1983-05-09	1985-02-12	G. D. Searle & Co.	Protease inhibitors
US4469885A (en) *	1983-05-09	1984-09-04	G. D. Searle & Co.	Halogenated protease inhibitors
DE3400342A1 (de) *	1984-01-07	1985-07-18	Henkel KGaA, 4000 Düsseldorf	Verwendung von salicylsaeureestern als riechstoffe, diese enthaltende riechstoffkompositionen, sowie neue salicylsaeureester
DE3404310A1 (de) *	1984-02-08	1985-08-08	Henkel KGaA, 4000 Düsseldorf	Verwendung von salicylsaeureestern als riechstoffe und diese enthaltende riechstoffkompositionen
US5399178A (en) *	1993-12-17	1995-03-21	Chevron Chemical Company	Mannich condensation products of polyalkylene hydroxyaromatic esters and fuel compositions containing the same
FR2740450B1 (fr) *	1995-10-27	2001-09-28	Rhone Poulenc Chimie	Procede d'obtention de compositions parfumantes et de produits parfumes et produits ainsi obtenus
US8124036B1 (en)	2005-10-27	2012-02-28	ADA-ES, Inc.	Additives for mercury oxidation in coal-fired power plants
KR100454647B1 (ko) *	2001-12-22	2004-11-05	삼성전자주식회사	금속 착화 그룹을 함유하는 디알킬하이드록시벤조산유도체 및 이의 치료적 용도
US20050032672A1 (en) *	2003-08-06	2005-02-10	Narula Anubhav P.S.	Fragrance compositions
US8524179B2 (en)	2010-10-25	2013-09-03	ADA-ES, Inc.	Hot-side method and system
US8951487B2 (en)	2010-10-25	2015-02-10	ADA-ES, Inc.	Hot-side method and system
US8496894B2 (en)	2010-02-04	2013-07-30	ADA-ES, Inc.	Method and system for controlling mercury emissions from coal-fired thermal processes
AU2011212805B2 (en)	2010-02-04	2016-03-24	ADA-ES, Inc.	Method and system for controlling mercury emissions from coal-fired thermal processes
CA2792732C (en)	2010-03-10	2018-07-31	Martin A. Dillon	Process for dilute phase injection of dry alkaline materials
US8784757B2 (en)	2010-03-10	2014-07-22	ADA-ES, Inc.	Air treatment process for dilute phase injection of dry alkaline materials
US8845986B2 (en)	2011-05-13	2014-09-30	ADA-ES, Inc.	Process to reduce emissions of nitrogen oxides and mercury from coal-fired boilers
CN102381980A (zh) *	2011-07-27	2012-03-21	江苏省江大绿康生物工程技术研究有限公司	一种羟苯酯钠喷雾干燥液的制备方法
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US2312001A (en) *	1939-04-19	1943-02-23	Heyden Chemical Corp	Production of dry alkali metal phenolates
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1979
- 1979-09-17 DE DE7979103467T patent/DE2961325D1/de not_active Expired
- 1979-09-17 EP EP79103467A patent/EP0009699B1/de not_active Expired
- 1979-09-20 US US06/077,445 patent/US4276431A/en not_active Expired - Lifetime
- 1979-09-27 IL IL58343A patent/IL58343A/xx unknown
- 1979-09-28 DK DK409279A patent/DK409279A/da not_active Application Discontinuation
- 1979-09-28 DD DD79215892A patent/DD146285A1/de unknown
- 1979-09-28 ES ES484577A patent/ES484577A1/es not_active Expired
- 1979-09-28 CA CA000336560A patent/CA1140572A/en not_active Expired

Also Published As

Publication number	Publication date
IL58343A (en)	1982-08-31
DE2961325D1 (en)	1982-01-14
CA1140572A (en)	1983-02-01
US4276431A (en)	1981-06-30
EP0009699B1 (de)	1981-11-11
EP0009699A1 (de)	1980-04-16
ES484577A1 (es)	1980-06-16
DK409279A (da)	1980-03-31

Publication	Publication Date	Title
EP0009699B1 (de)	1981-11-11	Verfahren zur Herstellung weitgehend wasserfreier und Hydroxybenzoesäure-freier Alkalisalze von Hydroxybenzoesäureestern
DE925476C (de)	1955-03-21	Verfahren zur Herstellung von farblosen, wasserloeslichen, trifluormethyl- und sulfonsaeuregruppenhaltigen, aliphatischen oder aromatischen Carbonsaeure- bzw. Sulfonsaeurearyliden
DE1196308B (de)	1965-07-08	Verfahren zur Herstellung von Anthrachinon-farbstoffen
DE2917273A1 (de)	1980-11-06	Weitgehend wasserfreie und hydroxybenzoesaeure-freie alkalisalze von hydroxybenzoesaeureestern und verfahren zu ihrer herstellung
DE2065446A1 (de)	1973-08-09	Jodierungsverfahren organischer verbindungen
DE1443325C3 (de)	1975-04-24	Verfahren zur Herstellung von 2,5-Diarylaminoterephthalsäuren oder deren Estern
DE1668990A1 (de)	1971-10-14	Halogensubstituierte p-(p-Alkoxyphenoxy)-phenoxyalkancarbonsaeuren und die entsprechenden Alkylester und Alkancarbonsaeureamide
DE3024265A1 (de)	1981-01-15	Verfahren zur herstellung von optisch aktiven aryloxylalkansaeure-verbindungen
DE2842807A1 (de)	1980-04-10	Verfahren zur herstellung von wasserfreien alkalisalzen von hydroxybenzoesaeureestern und wasserfreie alkalisalze von hydroxybenzoesaeureestern
DE1468406A1 (de)	1968-12-05	Verfahren zur Herstellung von Ascorbinsaeurediestern
DE4329286C1 (de)	1994-12-08	Verfahren zur Herstellung von aromatischen Methoxycarbonsäuremethylestern
DE830511C (de)	1952-02-04	Verfahren zur Herstellung von neuen diquartaeren Salzen von Pyrimidylaminochinolinen
EP1690855B1 (de)	2014-01-22	Mischung umfassend Phenylen-bis-benzimidazol-tetrasulfonsäure-dinatriumsalz
DE2055422A1 (de)	1971-05-19	Gegen Ultravioletthcht und Warme stabilisierte Kunststoffzusammensetzungen Ausscheidung aus 2046994
AT163640B (de)	1949-07-25	Verfahren zur Herstellung eines Salzes einer Chloraryloxyalkylcarbonsäure
CH440261A (de)	1967-07-31	Verfahren zur Herstellung von Äthionsäureestern und deren Salzen
AT163638B (de)	1949-07-25	Verfahren zur Herstellung von Methylchlorphenoxyalkylcarbonsäureverbindungen
DE1543295C3 (de)	1978-05-18	N-substituierte Anthranilsäuren, deren Salze, Verfahren zur Herstellung dieser Verbindungen und diese Verbindungen enthaltende Arzneimittel
DE686243C (de)	1940-01-05	Verfahren zur Herstellung von Abkoemmlingen der Pyridin-2, 3-dicarbonsaeure
CH618692A5 (da)	1980-08-15
AT254876B (de)	1967-06-12	Verfahren zur Herstellung des neuen Äthyl- oder Methylesters der 6,7-Diisobutoxy-4-hydroxy-3-chinolincarbonsäure
DE673174C (de)	1939-03-17	Verfahren zur Herstellung von 4-Methyl-5-ª‰-oxyaethylthiazol
AT143315B (de)	1935-11-11	Verfahren zur Darstellung von Chinolinderivaten.
DE2149709A1 (de)	1972-04-13	Neue-Triol-Verbindung,Verfahren zu deren Herstellung sowie deren Anwendung
DE825548C (de)	1951-12-20	Verfahren zur Herstellung von neuen diquartaeren Salzen von Pyrimidylaminocinnolinen