CA1038884A - Method of producing carboxymethyloxysuccinic acid - Google Patents
Method of producing carboxymethyloxysuccinic acidInfo
- Publication number
- CA1038884A CA1038884A CA237,114A CA237114A CA1038884A CA 1038884 A CA1038884 A CA 1038884A CA 237114 A CA237114 A CA 237114A CA 1038884 A CA1038884 A CA 1038884A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- calcium
- carboxymethyloxysuccinic
- carboxymethyloxysuccinic acid
- process according
- Prior art date
- 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
Links
- CIOXZGOUEYHNBF-UHFFFAOYSA-N (carboxymethoxy)succinic acid Chemical compound OC(=O)COC(C(O)=O)CC(O)=O CIOXZGOUEYHNBF-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims description 19
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims abstract description 27
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims abstract description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 20
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 20
- 159000000007 calcium salts Chemical class 0.000 claims abstract description 16
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000011976 maleic acid Substances 0.000 claims abstract description 10
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims abstract description 5
- 239000000920 calcium hydroxide Substances 0.000 claims abstract description 5
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims abstract description 5
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 230000020477 pH reduction Effects 0.000 claims description 7
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910001424 calcium ion Inorganic materials 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 150000004683 dihydrates Chemical class 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 15
- 239000000706 filtrate Substances 0.000 abstract description 5
- 238000001914 filtration Methods 0.000 abstract description 3
- 239000012736 aqueous medium Substances 0.000 abstract description 2
- 229910052925 anhydrite Inorganic materials 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000011575 calcium Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 229940032330 sulfuric acid Drugs 0.000 description 7
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 6
- 235000011941 Tilia x europaea Nutrition 0.000 description 6
- ZMLSBGGVJNASMM-UHFFFAOYSA-L calcium;2-(carboxymethoxy)butanedioate Chemical compound [Ca+2].OC(=O)COC(C([O-])=O)CC([O-])=O ZMLSBGGVJNASMM-UHFFFAOYSA-L 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 239000004571 lime Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 235000011087 fumaric acid Nutrition 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- RWYRUDPAALLKPX-UHFFFAOYSA-N 2,2-difluoro-n-methylethanamine;hydrochloride Chemical compound Cl.CNCC(F)F RWYRUDPAALLKPX-UHFFFAOYSA-N 0.000 description 3
- CFPOJWPDQWJEMO-UHFFFAOYSA-N 2-(1,2-dicarboxyethoxy)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)OC(C(O)=O)CC(O)=O CFPOJWPDQWJEMO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 239000001749 Calcium fumarate Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000019296 calcium fumarate Nutrition 0.000 description 3
- HDRTWMBOUSPQON-ODZAUARKSA-L calcium;(z)-but-2-enedioate Chemical compound [Ca+2].[O-]C(=O)\C=C/C([O-])=O HDRTWMBOUSPQON-ODZAUARKSA-L 0.000 description 3
- CHRHZFQUDFAQEQ-UHFFFAOYSA-L calcium;2-hydroxyacetate Chemical compound [Ca+2].OCC([O-])=O.OCC([O-])=O CHRHZFQUDFAQEQ-UHFFFAOYSA-L 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- PASHVRUKOFIRIK-UHFFFAOYSA-L calcium sulfate dihydrate Chemical compound O.O.[Ca+2].[O-]S([O-])(=O)=O PASHVRUKOFIRIK-UHFFFAOYSA-L 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002689 maleic acids Chemical class 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 241000237074 Centris Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- -1 calcium carboxy-methyloxysuccinate Chemical compound 0.000 description 1
- CYZPYTYCOLAJON-UHFFFAOYSA-N calcium;2-(carboxymethoxy)butanedioic acid Chemical compound [Ca].OC(=O)COC(C(O)=O)CC(O)=O CYZPYTYCOLAJON-UHFFFAOYSA-N 0.000 description 1
- 150000004697 chelate complex Chemical class 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002238 fumaric acids Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- MPSJHIAGGNGGEZ-UHFFFAOYSA-K trisodium;2-(carboxylatomethoxy)butanedioate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)COC(C([O-])=O)CC([O-])=O MPSJHIAGGNGGEZ-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/514,018 US3948985A (en) | 1972-11-15 | 1974-10-11 | Method of producing carboxymethyloxysuccinic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1038884A true CA1038884A (en) | 1978-09-19 |
Family
ID=24045483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA237,114A Expired CA1038884A (en) | 1974-10-11 | 1975-10-06 | Method of producing carboxymethyloxysuccinic acid |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5165716A (enExample) |
| BE (1) | BE834412A (enExample) |
| CA (1) | CA1038884A (enExample) |
| CH (1) | CH614690A5 (enExample) |
| DE (1) | DE2545577A1 (enExample) |
| FR (1) | FR2287438A1 (enExample) |
| IT (1) | IT1043291B (enExample) |
| NL (1) | NL7511851A (enExample) |
| SE (1) | SE425310B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3377107D1 (en) * | 1982-03-26 | 1988-07-28 | Leur Eric Jean Anne De | Accessory for counteracting the consequences of vesical incontinence with males |
-
1975
- 1975-10-06 CA CA237,114A patent/CA1038884A/en not_active Expired
- 1975-10-09 NL NL7511851A patent/NL7511851A/xx not_active Application Discontinuation
- 1975-10-10 BE BE160866A patent/BE834412A/xx unknown
- 1975-10-10 IT IT28179/75A patent/IT1043291B/it active
- 1975-10-10 DE DE19752545577 patent/DE2545577A1/de not_active Ceased
- 1975-10-10 FR FR7531084A patent/FR2287438A1/fr active Granted
- 1975-10-10 SE SE7511411A patent/SE425310B/xx unknown
- 1975-10-10 CH CH1316775A patent/CH614690A5/xx not_active IP Right Cessation
- 1975-10-11 JP JP50121886A patent/JPS5165716A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2287438B1 (enExample) | 1979-03-09 |
| BE834412A (fr) | 1976-04-12 |
| NL7511851A (nl) | 1976-04-13 |
| CH614690A5 (en) | 1979-12-14 |
| IT1043291B (it) | 1980-02-20 |
| DE2545577A1 (de) | 1976-04-22 |
| JPS5165716A (en) | 1976-06-07 |
| FR2287438A1 (fr) | 1976-05-07 |
| SE7511411L (sv) | 1976-04-12 |
| SE425310B (sv) | 1982-09-20 |
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