GB694665A - Method of producing water-soluble products from black liquor lignin - Google Patents

Method of producing water-soluble products from black liquor lignin

Info

Publication number
GB694665A
GB694665A GB31198/50A GB3119850A GB694665A GB 694665 A GB694665 A GB 694665A GB 31198/50 A GB31198/50 A GB 31198/50A GB 3119850 A GB3119850 A GB 3119850A GB 694665 A GB694665 A GB 694665A
Authority
GB
United Kingdom
Prior art keywords
product
black liquor
lignin
reacted
sulphate
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
Application number
GB31198/50A
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.)
ERIK KARL MAURITS HAEGGLUND
Original Assignee
ERIK KARL MAURITS HAEGGLUND
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.)
Filing date
Publication date
Application filed by ERIK KARL MAURITS HAEGGLUND filed Critical ERIK KARL MAURITS HAEGGLUND
Publication of GB694665A publication Critical patent/GB694665A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08HDERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
    • C08H6/00Macromolecular compounds derived from lignin, e.g. tannins, humic acids

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)
  • Paper (AREA)

Abstract

A process for converting black liquor lignin into water-soluble products is characterized in that the black liquor lignin is sulphonated at an elevated temperature (e.g. 50 DEG to 200 DEG C.) with sulphurous acid or a salt thereof, or with a substance yielding sulphurous acid. Before, during or after sulphonation the lignin may be reacted with an aldehyde. A product containing -CH2SO3H groups is produced when the aldehyde is formaldehyde. The product may then be further sulphonated in the absence of an aldehyde. The black liquor lignin may be obtained by digesting hardwood or coniferous wood or other lignocellulose containing materials according to the soda or sulphate cellulose processes. Sulphonation may be effected under acid, neutral or alkaline conditions, e.g. with alkali metal or ammonium sulphites or bisulphites. Before or during sulphonation the lignin may be oxidized, e.g. by passing air or oxygen through its solution, if desired in the presence of iron, copper or cobalt. In the oxidation, sulphate black liquor lignin which contains combined sulphur is converted to a product containing sulphonic groups. In examples: (1) black liquor lignin is reacted in alkaline solution with sodium sulphite and sulphate and sulphite ions are removed from the product by dialysis; (2) black liquor lignin, sodium sulphite and formalin are heated together, the product is treated with a hydrogen-ion-saturated cation exchanger, and evaporated to dryness. The product which contains one sulphonic acid group to about 5 methoxyl groups is converted to its barium and calcium salts; (3) a procedure similar to (2) but with isolation of the product by salting out is followed; (4) black liquor lignin, sodium hydroxide, sodium sulphite and formalin are heated together. The product is purified by dialysis; (5) the lignin is heated with sodium sulphite and sodium hydroxide. After passing sulphur dioxide through the solution, the product is reacted with formalin; (6) the product of (2) is reacted with sodium pyrosulphite; (7) sulphite process black liquor lignin in boiling alkaline solution is oxidized by passing oxygen through. The product, containing sulphonic acid groups, is reacted with sodium sulphite and dialysed; (8) sulphate black liquor lignin, sodium hydroxide and sodium sulphite are heated in solution in two batches, through only one of which air is passed; (9) the product of (1) is reacted with sodium sulphite and formalin; (10) the product of (2) is reacted with a formalin-bisulphite addition product; (11) sulphate black liquor lignin is oxidized with air in alkaline solution and the product heated with a formaldehyde-bisulphite addition compound. The products are useful in tanning leather and as emulsifying and dispersing agents, e.g. in printing inks, and cutting and drilling oils, as levelling agents in dyeing, as fillers for caoutchouc, and as dispersing, hardening promoting, and strength-increasing additives for cement.ALSO:A process for converting black liquor lignin into water-soluble products is characterized in that the black liquor lignin is sulphonated at an elevated temperature, e.g. 50 DEG to 200 DEG C. with sulphurous acid or a salt thereof or with a substance yielding sulphurous acid. The black liquor lignin may be obtained by digesting hardwood or coniferous wood or other lignocellulose-containing materials according to the soda or sulphate cellulose processes. Sulphonation may be effected under acid, neutral or alkaline conditions, e.g. with alkali metal or ammonium sulphites or bisulphites. Before or during sulphonation the lignin may be oxidized e.g. by passing air or oxygen through its solution, if desired in the presence of catalysts such as salts of iron, copper or cobalt. Before or during sulphonation the lignin may be reacted with an aldehyde, a product containing -CH2SO3H groups then being produced when the aldehyde is formaldehyde. The product may then be further sulphonated in the absence of aldehyde. Previously sulphonated lignin may also be reacted with aldehydes. The molecular weight of the products is about 1000 to 3000, being lower when sulphate liquor lignin is employed in the reaction. Sulphate black liquor lignin contains combined sulphur mainly in the form of sulphide, thiol and disulphide groups, which in the oxidation step are converted to sulphonic acid groups. In examples: (1) black liquor lignin is reacted in alkaline solution with sodium sulphite, and sulphate and sulphite ions are removed by dialysis; (2) black liquor lignin, sodium sulphite and formalin are heated together, the product is treated with a hydrogen-ion-saturated cation exchanger, and evaporated to dryness. The product, which contains one sulphonic acid group to about 5 methoxyl groups is converted to its barium and calcium salts; (3) a procedure similar to (2) but with isolation of the product by salting out is followed; (4) black liquor lignin, sodium hydroxide, sodium sulphite and formalin are heated together. The product is purified by dialysis; (5) the lignin is heated in alkaline solution with sodium sulphite and sodium hydroxide. After cooling, SO2 is passed through and the product reacted with formalin and isolated as in (1); (6) the product of (2) is reacted with sodium pyrosulphite; (7) sulphate process black liquor lignin in boiling alkaline solution is oxidized by passing oxygen through. The product, containing sulphonic groups, is reacted with sodium sulphite and dialysed to remove sulphite ions; (8) sulphate black liquor lignin, sodium hydroxide, and sodium sulphite are heated in solution while passing air through the mixture. The product is not precipitated by acetic acid. The process is repeated in the absence of air to give a product which is precipitated by acetic acid; (9) the product of (1) is reacted with sodium sulphite and formalin; (10) the product of (2) is reacted with a formaldehyde-bisulphite addition product; (11) sulphate black liquor lignin is heated in alkaline solution while passing air through. The product is heated with formaldehyde-bisulphite addition compound. The products are useful in tanning leather and as emulsifying and dispersing agents, e.g. in printing inks and cutting and drilling oils, as levelling agents in dyeing, as fillers for caoutchouc, and as dispersing, hardening-promoting and strength-increasing additives for cement.
GB31198/50A 1949-12-22 1950-12-22 Method of producing water-soluble products from black liquor lignin Expired GB694665A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE694665X 1949-12-22

Publications (1)

Publication Number Publication Date
GB694665A true GB694665A (en) 1953-07-22

Family

ID=20315299

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31198/50A Expired GB694665A (en) 1949-12-22 1950-12-22 Method of producing water-soluble products from black liquor lignin

Country Status (1)

Country Link
GB (1) GB694665A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4088640A (en) * 1976-06-18 1978-05-09 American Can Company Ozonated lignosulfonates
EP0367389A1 (en) * 1988-10-24 1990-05-09 Westvaco Corporation Production of lignosulfonate additives
CN110092917A (en) * 2019-05-29 2019-08-06 南京工业大学 Lignin metal salt and preparation method and application thereof
CN114000369A (en) * 2021-09-28 2022-02-01 山东格瑞兰德添加剂有限公司 Method for preparing anionic surfactant from ultrafiltration sulfate pulping black liquor

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4088640A (en) * 1976-06-18 1978-05-09 American Can Company Ozonated lignosulfonates
EP0367389A1 (en) * 1988-10-24 1990-05-09 Westvaco Corporation Production of lignosulfonate additives
CN110092917A (en) * 2019-05-29 2019-08-06 南京工业大学 Lignin metal salt and preparation method and application thereof
CN110092917B (en) * 2019-05-29 2020-08-21 南京工业大学 Lignin metal salt and preparation method and application thereof
CN114000369A (en) * 2021-09-28 2022-02-01 山东格瑞兰德添加剂有限公司 Method for preparing anionic surfactant from ultrafiltration sulfate pulping black liquor

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